53 results on '"Spectrum analysis"'
Search Results
2. Nivalones C[sbnd]F, four new meroterpenoids from Rhododendron nivale.
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Wang, Lan, Zeng, Xi, Yuan, Tao, and Yao, Houzong
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INFLAMMATION prevention , *NONIONIZING radiation , *NUCLEAR magnetic resonance spectroscopy , *NITRIC oxide , *TERPENES , *PLANT stems , *ULTRAVIOLET radiation , *PLANT extracts , *NEUROLOGICAL disorders , *MEDICINAL plants , *MOLECULAR structure , *SPECTRUM analysis , *ELECTROSPRAY ionization mass spectrometry , *LIPOPOLYSACCHARIDES , *LEAVES - Abstract
Four new meroterpenoids, namely nivalones C F (1 – 4), along with a known meroterpenoid, cannabiorcicyclolic acid (5), were isolated from the branches and leaves of Rhododendron nivale. The chemical structures of compounds 1 – 4 were elucidated through comprehensive spectroscopic analyses, including NMR, UV–Vis, IR, ECD spectroscopy, as well as HR-ESI-MS. The isolated compounds were evaluated for their anti-inflammatory and neuroprotective properties. The inhibitory activity of compound 5 against lipopolysaccharide (LPS)-induced nitric oxide (NO) production was initially demonstrated, showcasing an IC 50 value of 21.1 μM. Additionally, both compounds 2 and 5 displayed a notable effect on the viability of H 2 O 2 -damaged SH-SY5Y cells, indicating their significant neuroprotection effects. Four new meroterpenoids 1 – 4 (nivalones C F) and a known meroterpenoid 5 with good anti-inflammatory and neuroprotective effects were isolated from Rhododendron nivale. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2024
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3. New 19(10 → 9)abeo-euphane-type triterpenoids from Trichilia dregeana leaves and NO production inhibitory activities.
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Mba Nguekeu, Yves M., Kodama, Takeshi, Tsepeupon Matchide, Marie G., Do, Kiep Minh, Nghokeng, Josker, Tabakam, Gaétan T., Tsuge, Kiyoshi, Ngouela, Silvère A., Mathieu, Tene, Awouafack, Maurice Ducret, and Morita, Hiroyuki
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TRITERPENES , *STEROIDS , *NITRIC oxide , *TERPENES , *PHYTOCHEMICALS , *PLANT extracts , *SPECTRUM analysis , *X-rays , *LIPOPOLYSACCHARIDES , *LEAVES , *ETHERS - Abstract
Phytochemical investigation of the EtOAc soluble fraction from leaves of Trichilia dregeana Sond. (Meliaceae) afforded naturally rare four new pentacyclic triterpenoids (1 – 4), together with five known pentacyclic analogs (5 – 8 , and 11) and two steroids (9 and 10). Their structures were elucidated by extensive spectroscopic techniques such as 1D and 2D NMR and HRESIMS data analyses. The absolute configuration of 1 was determined by using the single-crystal X-ray diffraction analysis. The nitric oxide (NO) production inhibitory assay indicated that the EtOAc fraction as well as 4 and 7 inhibited the NO production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with the IC 50 values of 83.53 μg/mL and 81.31 and 85.71 μM, respectively. Compounds 1 – 4 are rare 19(10 → 9) abeo -euphane-type triterpenoids bearing a 3,10-ether bridge. To the best of our knowledge, this study is the first isolation of triterpenoids with the 3,10-ether bridge in their skeleton from the genus Trichilia , providing new insights into the chemodiversity of the terpenoids in T. dregeana. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2024
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4. Anti-inflammatory naphthoquinone-monoterpene adducts and neolignans from Eugenia caryophyllata.
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Li, Xue-Yi, Jiang, Jun, Shu, Beiyi, Huang, Rui-Li, Yang, Hai-Xia, Chen, Ya-Li, Tang, Wei, Ye, Wen-Cai, Wang, Ying, Huang, Xiao-Jun, and Song, Jian-Guo
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PHYTOTHERAPY , *ANTI-inflammatory agents , *IN vitro studies , *QUINONE , *TERPENES , *PHYTOCHEMICALS , *RESPIRATORY syncytial virus infections , *EDIBLE plants , *ANTIVIRAL agents , *CARBOCYCLIC acids , *LIGNANS , *SPECTRUM analysis , *X-rays , *CRYSTALLOGRAPHY - Abstract
A phytochemical investigation on the buds of edible medicinal plant, Eugenia carvophyllata , led to the discovery of seven new compounds, caryophones A–G (1 – 7), along with two biogenetically-related known ones, 2-methoxy-7-methyl-1,4-naphthalenedione (8) and eugenol (9). Compounds 1 – 3 represent the first examples of C-5–C-1′ connected naphthoquinone-monoterpene adducts with a new carbon skeleton. Compounds 4 – 7 are a class of novel neolignans with unusual linkage patterns, in which the C-9 position of one phenylpropene unit coupled with the aromatic core of another phenylpropene unit. The chemical structures of the new compounds were determined based on extensive spectroscopic analysis, X-ray diffraction crystallography, and quantum-chemical calculation. Among the isolates, compounds (−)- 2 , 3 , 6 , and 9 showed significant in vitro inhibitory activities against respiratory syncytial virus (RSV)-induced nitric oxide (NO) production in RAW264.7 cells. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2024
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5. New eremophilane-type sesquiterpenes from Synotis solidaginea.
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Wei, Xin-Yi, Sun, Hong-Bing, Xi, Rui-Ying, Wu, Fan, Liu, Yi-Lin, Jin, Zhuo-Lin, Guo, Da-Le, Xia, Bing, Wang, Fei, and Zhou, Yan
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THERAPEUTIC use of antineoplastic agents , *MACROPHAGES , *HYDROCARBONS , *TERPENES , *COMPUTED tomography , *PHYTOCHEMICALS , *PLANT extracts , *MICE , *MEDICINAL plants , *ANIMAL experimentation , *MOLECULAR structure , *SPECTRUM analysis , *MYELOID leukemia , *CRYSTALLOGRAPHY - Abstract
Eleven new highly oxygenated eremophilane-type sesquiterpenoids were isolated from the whole plant of Synotis solidaginea , including two pairs of C-8 S / R epimers. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis and the absolute configurations of 1 and 9 were confirmed by single-crystal X-ray crystallography using Cu K α radiation. All the isolates were tested for the inhibition of LPS-stimulated NO production in macrophage-like mouse monocytic leukemia RAW264.7 cells. Compound 1 exhibited weak inhibitory effects with an IC 50 of 71.2 μM. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2024
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6. Five new eremophilane-type sesquiterpenes from the fresh roots of Rehmannia glutinosa.
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Li, Xiang-Da, Cao, Yan-Gang, Zhang, Yu-Han, Ren, Ying-Jie, Zeng, Meng-Nan, Liu, Yan-Ling, Chen, Xu, Ma, Xin-Yi, Zhao, Bing-Xian, Zheng, Xiao-Ke, and Feng, Wei-Sheng
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HYDROCARBON analysis , *IN vitro studies , *TERPENES , *APOPTOSIS , *PLANT roots , *PLANT extracts , *REACTIVE oxygen species , *MOLECULAR structure , *SPECTRUM analysis , *PULMONARY fibrosis - Abstract
Five undescribed eremophilane-type sesquiterpenes, remophilanetriols E -I (1 – 5), along with seven known compounds (6 – 12) were isolated from the fresh roots of Rehmannia glutinosa. Their structures were characterized by extensive spectroscopic data analysis and their absolute configurations were determined by comparing their calculated electronic circular dichroism (ECD) spectra and experimental ECD spectra. The anti-pulmonary fibrosis activities of all compounds were evaluated in vitro by MTT methods, and compounds 2 , 8 , 10 , and 12 exhibited excellent anti-pulmonary fibrosis activities. In addition, compound 2 can reduce the levels of ROS and apoptosis in TGF-β1-induced BEAS-2B cells. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2024
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7. Diterpenoid glucosides with anti-inflammatory activity from Sigesbeckia glabrescens.
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Tang, Lian-Yu, Zhang, Ya-Zhao, Gao, Yun, Tsering, Tashi, Jia, Jingming, and Wang, Anhua
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PLANT anatomy , *MACROPHAGES , *NITRIC oxide , *TERPENES , *PLANT extracts , *ANTI-infective agents , *MEDICINAL plants , *GLYCOSIDES , *LIPOPOLYSACCHARIDES , *SPECTRUM analysis , *INFLAMMATION , *PHARMACODYNAMICS - Abstract
Six previously undescribed diterpenoid glucosides, along with four known compounds, were isolated from the aerial parts of Sigesbeckia glabrescens. The structures and absolute configurations of undescribed compounds were elucidated using extensive spectroscopic techniques, ECD calculations and chemical methods. Compounds 1 and 8 exhibited anti-inflammatory activity against LPS-induced NO production in RAW 264.7 macrophages, with compound 8 demonstrating significant inhibitory activity compared to positive control minocycline, boasting an IC 50 value at 14.20 μM. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2024
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8. Isoprenoid flavonoids isolated from Sophora davidii and their activities induces apoptosis and autophagy in HT29 cells.
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Yuan, Jing-Jing, Meng, Yu-Fan, Zhang, Mao-Sheng, Guo, Da-Le, Yang, Jian-Wen, Dong, Min-Jian, Sun, Cheng-Xin, and Xiao, Shi-Ji
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EPITHELIAL cells , *MITOGEN-activated protein kinases , *AUTOPHAGY , *PHOSPHORYLATION , *ANTINEOPLASTIC agents , *FLAVONOIDS , *APOPTOSIS , *TERPENES , *PHYTOCHEMICALS , *COLON tumors , *CELL lines , *MEDICINAL plants , *MOLECULAR structure , *SPECTRUM analysis , *MATHEMATICAL models , *THEORY , *PHARMACODYNAMICS - Abstract
Four previously undescribed isoprenoid flavonoids (2 – 5) were isolated from Sophora davidii , along with five known analogues. The structures of the compounds were established through comprehensive analysis of spectroscopic data, including HRESIMS, 1D and 2D NMR, and absolute configurations determined by theoretical calculations, including ECD and NMR calculation. The cytotoxic effects of the isolated compounds on human HT29 colon cancer cells were evaluated using the MTT assay, compound 1 exhibited cytotoxicity against human HT29 colon cancer cells with an IC 50 value of 8.39 ± 0.09 μM. Studies conducted with compound 1 in HT29 cells demonstrated that it may induce apoptosis and autophagy in HT29 by promoting the phosphorylation of P38 MAPK and inhibiting the phosphorylation of Erk MAPK. Four previously undescribed isoprenoid flavonoids were isolated from Sophora davidii. Compound 1 showed significant inhibitory activity against human HT29 colon cancer cells. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2024
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9. Monoterpenoid indole alkaloids from Melodinus axillaris W.T.Wang exhibit anti-inflammatory activities by inhibiting the NF-κB signaling pathways.
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Du, Kaicheng, Liang, Yanan, Song, Zihao, Zheng, Changwei, Lai, Lantao, Zong, Kunqi, Wang, Yumeng, and Meng, Dali
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BIOLOGICAL models , *IN vitro studies , *CYCLOOXYGENASE 2 , *MEDICINAL plants , *HERBAL medicine , *TERPENES , *ALKALOIDS , *ANTI-inflammatory agents , *INFLAMMATION , *WESTERN immunoblotting , *NONSTEROIDAL anti-inflammatory agents , *NF-kappa B , *NUCLEAR magnetic resonance spectroscopy , *CELLULAR signal transduction , *PHYTOCHEMICALS , *MASS spectrometry , *CELL lines , *NITRIC oxide , *CHINESE medicine , *SPECTRUM analysis , *PHARMACODYNAMICS - Abstract
Melodinus axillaris W.T.Wang has been widely used as an important medicine in China. In the folk of China, its whole plant has been used for fractures, rheumatic heart disease, testitis, hernia, abdominal pain, and dyspepsia, etc. Despite its extensive use, there is a shortage of literature investigating the specific bioactive compounds and underlying mechanisms responsible for their anti-inflammatory effects. This knowledge gap serves as the primary impetus for conducting this study, which aims to shed light on the previously unexplored therapeutic potential of M. axillaris. This study aims to investigate the material basis and potential mechanism of anti-inflammatory activity of M. axillaris. Compounds were isolated from the 95% ethanol extract of M. axillaris using a systematic phytochemical method. The structures were established by extensive spectroscopic analysis, including 1D and 2D NMR, HR-ESI-MS, ECD calculation, and DP4+ analysis. The anti-inflammatory activities of ethanol extract and compounds from M. axillaris were tested by an inflammation model of LPS-stimulated RAW264.7 cells in vitro. Western blot analysis was employed to evaluate the expressions of COX-2, iNOS, and NF-κB signaling pathways, aiming to elucidate the underlying mechanisms. Eleven undescribed monoterpenoid indole alkaloids (MIAs), axillines A−K (1 – 11), along with thirteen known analogs were isolated from M. axillaris. Compound 1 was the first representative of vincadine alkaloid with unprecedented 6/5/9/6/6 skeletons. Compounds 1 – 11 and ethanol extract showed significant anti-inflammatory effects in vitro. Among them, compound 2 had the best activity of inhibiting NO release (IC 50 = 3.7 ± 0.9 μM). Additionally, subsequent Western blot analysis revealed that 2 could significantly inhibit the up-regulation of NF-κB signaling pathways, iNOS, and COX-2 in LPS-stimulated RAW264.7 cells, thereby demonstrating its anti-inflammatory activity. This study provides support for the traditional use of M. axillaris in terms of its anti-inflammatory properties and highlights the potential of MIAs as promising candidates for further development as anti-inflammatory drugs. [Display omitted] • Eleven undescribed monoterpenoid indole alkaloids (MIAs) were isolated from M. axillaris. • Compound 1 was the first representative of vincadine alkaloid with 6/5/9/6/6 skeletons. • These MIAs were isolated exhibited significant anti-inflammation activity. • Compound 2 inhibited inflammation by NF-κB signaling pathway. [ABSTRACT FROM AUTHOR]
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- 2024
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10. Secondary metabolites isolated from Trichoderma hamatum b-3 and their fungicidal activity.
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Huang, Li, Liu, Meng-Dan, Hu, Yi-Wen, Chen, Li-Juan, Deng, Yun, Gu, Yu-Cheng, Bian, Qiang, Guo, Da-Le, and Wang, Guang-Zhi
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FUNGAL metabolism , *ANTIFUNGAL agents , *HETEROCYCLIC compounds , *TERPENES , *METABOLITES , *MOLECULAR structure , *SPECTRUM analysis , *PHARMACODYNAMICS - Abstract
An undescribed trichodenone derivative (1), two new diketopiperazines (3 and 4) along with a bisabolane analog (2) were isolated from Trichoderma hamatum b-3. The structures of the new findings were established through comprehensive analyses of spectral evidences in HRESIMS, 1D and 2D NMR, Marfey's analysis as well as comparisons of ECD. The absolute configuration of 2 was unambiguously confirmed by NMR, ECD calculation and Mo 2 (AcO) 4 induced circular dichroism. Compounds 1 – 4 were tested for their fungicidal effects against eight crop pathogenic fungi, among which 1 showed 51% inhibition against Sclerotinia sclerotiorum at a concentration of 50 μg/mL. [Display omitted] • Three previously undescribed compounds were isolated form Trichoderma hamatum b-3. • The absolute configurations of all the isolated compounds were elucidated. • 1 showed 51% inhibition against Sclerotinia sclerotiorum at a concentration of 50 μg/mL. [ABSTRACT FROM AUTHOR]
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- 2024
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11. Chemodiverse monoterpene indole alkaloids from Kopsia teoi, inhibitory potential against α-amylase, and their molecular docking studies.
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Muhammad, Muhammad Tahir, Beniddir, Mehdi A., Phongphane, Lacksany, Abu Bakar, Mohamad Hafizi, Hussin, Mohd Hazwan, Awang, Khalijah, Litaudon, Marc, Supratman, Unang, and Azmi, Mohamad Nurul
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COMPUTER-assisted molecular modeling , *IN vitro studies , *ALKALOIDS , *TERPENES , *HYDROCARBONS , *PHYTOCHEMICALS , *TREATMENT effectiveness , *DESCRIPTIVE statistics , *INSULIN , *HYPOGLYCEMIC agents , *PLANT extracts , *BARK , *BLOOD sugar , *SECRETION , *SPECTRUM analysis , *MOLECULAR structure , *COMPARATIVE studies , *DIABETES , *AMYLASES , *ACARBOSE - Abstract
Diabetes mellitus stands as a metabolic ailment marked by heightened blood glucose levels due to inadequate insulin secretion. The primary aims of this investigative inquiry encompassed the isolation of phytochemical components from the bark of Kopsia teoi , followed by the assessment of their α-amylase inhibition. The phytochemical composition of the K. teoi culminated in the discovery of a pair of new indole alkaloids; which are 16- epi -deacetylakuammiline N (4)-methylene chloride (akuammiline) (1), and N (1)-methoxycarbonyl-11-methoxy-12-hydroxy-Δ14–17-kopsinine (aspidofractinine) (2), together with five known compounds i.e. kopsiloscine G (aspidofractinine) (3), akuammidine (sarpagine) (4), leuconolam (aspidosperma) (5), N -methoxycarbonyl-12-methoxy-Δ16, 17-kopsinine (aspidofractinine) (6), and kopsininate (aspidofractinine) (7). All compounds were determined via spectroscopic analyses. The in vitro evaluation against α-amylase showed good inhibitory activities for compounds 5 – 7 with the inhibitory concentration (IC 50) values of 21.7 ± 1.2, 34.1 ± 0.1, and 30.0 ± 0.8 μM, respectively compared with the reference acarbose (IC 50 = 34.4 ± 0.1 μM). The molecular docking outputs underscored the binding interactions of compounds 5 – 7 ranging from −8.1 to −8.8 kcal/mol with the binding sites of α-amylase. Consequently, the outcomes highlighted the anti-hyperglycemic attributes of isolates from K. teoi. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2024
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12. Five new sesquiterpenoids isolated from Dictamnus dasycarpus Turcz.
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Sun, Ye, Liu, Yan, Wang, Si-Yi, Yang, Xu, Wu, Jia-Tong, Pan, Juan, Hao, Zhi-Chao, Guan, Wei, Algradi, Adnan-Mohammed, Xu, Zhen-Peng, Zhou, Yuan-Yuan, Lv, Shao-Wa, Kuang, Hai-Xue, and Yang, Bing-You
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IN vitro studies , *NUCLEAR magnetic resonance spectroscopy , *COLORIMETRY , *TERPENES , *CELL proliferation , *ANTINEOPLASTIC agents , *PHYTOCHEMICALS , *CELL lines , *INFRARED spectroscopy , *MEDICINAL plants , *MOLECULAR structure , *SPECTRUM analysis , *MASS spectrometry , *BIOLOGICAL assay , *PHARMACODYNAMICS - Abstract
Five new sesquiterpenoids, dictamtrinorguaianols E and F (1–2), and dictameudesmnosides F, G, and H (3–5), along with seven known sesquiterpenoids (6–12) were isolated from Dictamnus dasycarpus Turcz. The structures of all new compounds were characterized by spectroscopic methods, including UV, IR, HR-ESI-MS, and 1D and 2D NMR. The In-vitro anti-proliferative activities of all the compounds against two human cancer cell lines (SW982 and A549) were evaluated by CCK-8 assay. Compounds 1 and 4 showed medium anti-proliferative activity against SW982 cells, with IC 50 values of 3.49 ± 0.10 and 6.42 ± 1.23 μM, respectively. Additionally, compounds 2 , 7 , and 8 exhibited medium anti-proliferative activity against A549 cells, with IC50 values ranging from 0.80 ± 0.05 to 6.60 ± 0.46 μM. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2024
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13. The intramolecular SN2 reaction tautomeric ent-Kauranoids isolated from the aerial parts of Isodon amethystoides.
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Wu, Lan, Zhang, Ming, Liu, Wen-Hu, Chen, Yan-fang, Yin, Xiu-wen, Han, Zhengbin, Ren, Fu-cai, Pu, Xiang-dong, Liu, Xin-hua, Shi, Jing-bo, and Shen, Chuan-pu
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MEDICINAL plants , *TERPENES , *HIGH performance liquid chromatography , *PLANT anatomy , *NUCLEAR magnetic resonance spectroscopy , *PHYTOCHEMICALS , *MASS spectrometry , *PLANT extracts , *SPECTRUM analysis - Abstract
As our ongoing searching for the bioactive natural terpenoids, nine ent -kauranoids (1 – 9), including three previously undescribed ones (1 , 2 , and 9), were isolated from the aerial parts of Isodon amethystoides. Their structures were elucidated on the basis of spectroscopic data analysis, including NMR, MS, and ECD. Compounds 1 and 2 were a pair of tautomeric compounds, which was confirmed by the HPLC analysis and low temperature NMR testing. The underlying mechanism of the tautomer was proposed as an intramolecular S N 2 reaction, which was explained by quantum chemical calculation. The HOMO-LUMO gap and the free energy revealed the spontaneous of the tautomeric of the 1 and 2. Additionally, the similar phenomena were also found in the two groups of known compounds 3 and 4 and 6 and 7 , respectively. Apart from the tautomer, compounds 3 and 4 can be hydrolyzed into 5 through ester hydrolysis in CDCl 3 , while compounds 6 , 7 can be hydrolyzed into 8 through ester hydrolysis. These phenomena were also confirmed through HPLC analysis and low temperature nuclear magnetic resonance tests and the mechanism was studied using quantum chemical calculation. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2024
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14. LC-MS identification, isolation, and structural elucidation of anti-HIV macrocyclic daphnane orthoesters from Edgeworthia chrysantha.
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Otsuki, Kouharu, Kobayashi, Tsubasa, Nakamura, Kazuki, Kikuchi, Takashi, Huang, Li, Chen, Chin-Ho, Koike, Kazuo, and Li, Wei
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FOLIAR diagnosis , *ORGANIC compound analysis , *ANTI-HIV agents , *BIOCHEMISTRY , *TERPENES , *LIQUID chromatography-mass spectrometry , *PHENOMENOLOGICAL biology , *ELECTRON microscopy , *PHYTOCHEMICALS , *FLOWERS , *PLANT stems , *ORGANIC chemistry , *MASS spectrometry , *PLANT extracts , *MOLECULAR structure , *SPECTRUM analysis , *AMIDES - Abstract
The occurrence of macrocyclic daphnane orthoesters (MDOs) with a 1-alkyl group originating from a C 14 aliphatic chain is extremely limited in the plant kingdom and has only been isolated from Edgeworthia chrysantha. In the present study, LC-ESI-MS/MS analysis was performed on different parts of E. chrysantha , including flower buds, flowers, leaves, and stems, and resulted in the identification of seven MDOs in all the four plant parts, including two previously unreported compounds 1 and 7. Further LC-MS guided isolation was carried out to afford compounds 1 and 7 , and their structures were determined by various spectroscopic analyses. These compounds were also evaluated for anti-HIV activity, thus expanding insights into the structure-activity relationships for MDOs. [Display omitted] • Seven macrocyclic daphnane orthoesters were identified from Edgeworthia chrysantha by LC-ESI-MS/MS analysis. • ESI-MS/MS fragmentation of macrocyclic daphnane orthoesters was elucidated. • Two unreported compounds were isolated by LC-MS guided isolation. • Structures of isolated compounds were determined by various spectroscopic analyses. • Isolated compounds were evaluated for anti-HIV activity. [ABSTRACT FROM AUTHOR]
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- 2024
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15. Chemical constituents from Eupatorium fortunei and their anti-inflammatory evaluation by in silico and experimental approaches.
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Miao, Lei, Wei, Quan-Hao, Wang, Shu-Ting, Sun, Ping, and Zhang, Hua
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MEDICINAL plants , *LIGNANS , *TERPENES , *ESSENTIAL oils , *PLANT anatomy , *ANTI-inflammatory agents , *NF-kappa B , *CELLULAR signal transduction , *PLANT extracts , *ANALYTICAL chemistry techniques , *PHARMACEUTICAL chemistry , *FATTY acids , *SPECTRUM analysis - Abstract
The well-known aromatic and medicinal plant Eupatorium fortunei Turcz. is widely cultivated in China, and previous studies on its bioactive constituents mainly focus on the essential oil ingredients especially thymol derivatives. However, reports on other type of constituents and the potential application are lacking. In the present project, an intensive chemical fractionation on the aerial part extract of E. fortunei led to the isolation and identification of a series of fatty acid derivatives (lipids, 1a / 1b - 19) including seven pairs of previously undescribed enantiomers (1a / 1b - 7a / 7b), as well as a lignan (brachangobinan A (BBA), 20) and two monoterpenes (8 S /8 R -9-hydroxythymol, 21a / 21b). A preliminary biological evaluation of these compounds in a NO production inhibitory assay model demonstrated compound BBA as the most active one. Network pharmacology analysis was used to predict and explore the possible anti-inflammatory targets and mechanism of BBA, which revealed some potential inflammation-related proteins and signaling pathways. Further experimental investigations validated that the anti-inflammatory effect of BBA could be achieved by suppressing pro-inflammatory factors and blocking the activation of NF-κB signaling pathway. Taken together, our work shows that E. fortunei can serve as a potential resource of lipids and anti-inflammatory agents. [Display omitted] • Twenty-nine constituents including 26 fatty acids were isolated from Eupatorium fortunei. • The structures of the isolates were elucidated by analyses of spectroscopic data. • The lignan brachangobinan A showed the best inhibitory activity against NO production. • Network pharmacology was employed to predict the potential anti-inflammatory mechanism. • The biological effect and mechanism of brachangobinan A was validated by experimental work. [ABSTRACT FROM AUTHOR]
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- 2023
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16. New ophiobolin sesterterpenoid and drimane sesquiterpenoids from a marine-alga-derived fungus Aspergillus sp.
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Fang, Sheng-Tao, Shi, Zhen-Zhen, Song, Yin-Ping, Yin, Xiu-Li, and Ji, Nai-Yun
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TERPENES , *FUNGI , *HYDROCARBONS , *ELECTRON microscopy , *COMPARATIVE studies , *CHALONES , *ALGAE , *ASPERGILLUS , *SPECTRUM analysis - Abstract
Further investigation of secondary metabolites of a marine-alga-derived fungus Aspergillus sp. RR-YLW-12 led to isolate one new ophiobolin-type sesterterpenoid (1), four new drimane-type sesquiterpenoids (2 – 5) and one natural occurring compound (6), together with seven known compounds (7 – 13). Their structures and stereochemistry were elucidated by extensive spectroscopic analysis of NMR and HRMS experiments, and by comparison with the literature data. All isolates were evaluated for growth inhibition of five marine harmful microalgae. The new compounds exhibited significant to moderate inhibitory effects towards all tested microalgae species with IC 50 values ranging from 5.8 to 54.5 μg/mL. [Display omitted] • Five new terpenoids were isolated from a marine-alga-derived fungus Aspergillus sp. RR-YLW-12. • Their structures were elucidated by NMR, HR-MS and ECD analysis. • The isolates displayed significant to moderate inhibitory effects against five marine harmful microalgae species. [ABSTRACT FROM AUTHOR]
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- 2023
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17. Unusual 5/5 fused bicyclosesquiterpenoids from Eupatorium adenophorum.
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Geng, Hao, Luo, Jia-Hui, Gu, Wen-Jie, Zhang, Jun-Jie, Yang, Yong-Xun, and Yu, Yang
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IN vitro studies , *MEDICINAL plants , *TERPENES , *PLANT anatomy , *ANTI-inflammatory agents , *ANTINEOPLASTIC agents , *CHROMATOGRAPHIC analysis , *MOLECULAR structure , *SPECTRUM analysis , *ANTIBIOTICS - Abstract
The chemical analysis on the aerial sections of Eupatorium adenophorum Spreng. resulted in the identification of four unprecedented 5/5 fused bicyclosesquiterpenoids, eupatorid A (1), and its analogues named eupatorester A-C (2 – 4) using various chromatographic techniques. Their structures were unambiguously confirmed by detailed spectroscopic investigations (including 1D, 2D-NMR and HRMS), and single crystal X-ray diffraction. The anti-inflammatory activities, in vitro tumor growth inhibitory activities and antibacterial activities of these compounds were evaluated. Four sesquiterpenoids possessing an unprecedented skeleton were isolated and characterized from the aerial parts of Eupatorium adenophorum Spreng. (Compositae) and their anti-inflammatory activities, in vitro tumor growth inhibitory activities and antibacterial activities of these compounds were evaluated. [Display omitted] • Four sesquiterpenoids possessing an unprecedented skeleton were found from Eupatorium adenophorum. • Their chemical structures were well elucidated. • Their anti-inflammatory, antibacterial and cytotoxic activities were evaluated. [ABSTRACT FROM AUTHOR]
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- 2023
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18. Four new eudesmane-type and one new eremophilane-type sesquiterpenes from the whole plant of Carpesium abrotanoides L.
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Fan, Yu-Wen, Zhang, Wei-Jie, Ao, Zhuo-Yi, Chen, Jia-Yan, Lian, Xin, Pan, Yong-Chen, Chen, Li-Ping, Jiang, Dong-Xu, and Wu, Jie-Wei
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HYDROCARBON analysis , *COVID-19 , *TERPENES , *NUCLEAR magnetic resonance spectroscopy , *PLANT extracts , *SPECTRUM analysis - Abstract
The extract of the whole plant of Carpesium abrotanoides L. yielded five new sesquiterpenes including four eudesmanes (1 – 4) and one eremophilane (5). The new compounds were characterized by spectroscopic analysis especially 1D and 2D NMR spectroscopy and HRESIMS data. Structurally, both compounds 1 and 2 were sesquiterpene epoxides and 2 owned an epoxy group at C-4/C-15 position to form a spiro skeleton. Compounds 4 and 5 were two sesquiterpenes without lactones and 5 possessed a carboxy group in the molecule. Additionally, all the isolated compounds were preliminarily evaluated for the inhibitory activity against SARS-CoV-2 main protease. As a result, compound 2 showed moderate activity with an IC 50 value of 18.79 μM, while other compounds were devoid of noticeable activity (IC 50 > 50 μM). [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2023
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19. Meroterpenoids from Ganoderma petchii inhibiting migration of triple negative breast cancer cells.
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Zhang, Jiao-Jiao, Guo, Ping-Xia, Yang, Zhong-Hui, Cai, Dan, Dai, Wei-Feng, Lu, Qing, and Cheng, Yong-Xian
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X-rays , *TERPENES , *MAGNETIC resonance imaging , *NUCLEAR magnetic resonance spectroscopy , *CELL motility , *PLANT extracts , *CELL lines , *BREAST tumors , *SPECTRUM analysis - Abstract
Ganoderpetchoids A−E and (−)-dayaolingzhiol H, six undescribed meroterpenoids, were isolated from Ganoderma petchii. Their structures including the relative configurations were identified by means of spectroscopic methods and 13C NMR calculations. Chiral separation of the new racemics was performed to afford their respective enantiomers. The absolute configurations of the new isolates were clarified by computational approaches, CD comparisons and X-ray diffraction analysis. Biological studies toward triple negative breast cancer indicated that (+)- 6 and (−)- 6 significantly inhibit the migration of MDA-MB-231 cell line. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2023
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20. New aphidicolane diterpenoids with glucose consumption promoting and cell viability enhancing activities from Scoparia dulcis.
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Dong, Lin, Chen, Mimi, Huang, Zibao, Cao, Mingyu, Zhang, Yong, Sun, Wanying, Liu, Chenpeng, Zhang, Caiyun, Zhang, Shouwen, and Zhang, Xiaopo
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TERPENES , *MEDICINAL plants , *ANIMAL experimentation , *AMP-activated protein kinases , *ELECTROSPRAY ionization mass spectrometry , *CELL survival , *GLUCOSE , *MOLECULAR structure , *CELL lines , *SPECTRUM analysis , *FATTY acids - Abstract
Two new aphidicolane diterpenoids, termed Scopadulinol A (1) and B (2), were obtained from whole plants of Scoparia dulcis. Their structures were elucidated by applying various spectroscopic techniques, including 1D- and 2D-NMR and HR-ESI-MS. The absolute configurations of 1 and 2 were determined by applying the calculated electronic circular dichroism (ECD). In addition, both compounds were tested for their effects on glucose consumption in HL-7702 cells and on palmitic acid (PA) induced viability in MIN6 cells at different concentrations. The results showed that they significantly promoted glucose consumption and attenuated the PA-induced decrease of cell viability. Additionally, 2 was tested to determine whether it could activate AMP-activated protein kinase (AMPK), but it showed no such effect at the tested dosage. These results indicated that the new compounds might promote glucose consumption through other pathways but not by activating AMPK. Collectively, we highlighted the isolation of two new aphidicolane diterpenoids from S. dulcis and found that they could promote glucose consumption and attenuate PA-induced decrease of cell viability. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2023
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21. Monoterpenoid derivatives from Hyssopus cuspidatus Boriss. and their bioactivities.
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Aihaiti, Kariyemu, Li, Jun, Xu, Nan-nan, Tang, Dan, and Aisa, Haji Akber
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INTERLEUKINS , *LIPOPOLYSACCHARIDES , *ESCHERICHIA coli , *MEDICINAL plants , *TERPENES , *ANTI-inflammatory agents , *STEROIDS , *ANTINEOPLASTIC agents , *PLANTS , *CRYSTALLOGRAPHY , *TUMOR necrosis factors , *STAPHYLOCOCCUS aureus , *DESCRIPTIVE statistics , *PLANT extracts , *MOLECULAR structure , *CELL lines , *CANDIDA albicans , *ANTIBIOTICS , *SPECTRUM analysis , *PHARMACODYNAMICS - Abstract
Six undescribed monoterpenoids, together with twelve known compounds were isolated and identified from Hyssopus cuspidatus Boriss. Their structures were established by spectroscopic analysis, and the absolute configurations were established by ECD calculations and single-crystal X-ray diffraction crystallography. The isolated compounds were tested for their anti-inflammatory, antibacterial and antitumor activities. Most of the compounds showed potent anti-inflammatory activities. Among them, 3 β -hydroxy-7,8-dihydro- β -ionone (8), oleanolic acid (17) and acetylpleamolic acid (18) showed strong anti-inflammatory activity against IL-6 and TNF- α in lipopolysaccharide (LPS) stimulated RAW 264.7 cells. Several compounds showed moderate inhibitory activities against Staphylococcus aureus , Candida albicans , and Escherichia coli. And (4 S)- p -menth-l-ene-7,8-diol 8- O - β -D-glucopyranoside (16) showed antitumor activities against MCF-8 and HT-29 cell lines with IC 50 values of 93.39 ± 3.69 and 71.89 ± 2.94 μ M, respectively. Oleanolic acid (17) showed moderate antitumor activity against HT-29 cell lines with an IC 50 value of 52.62 ± 1.63 μ M. In this study, the discovery of anti-inflammatory, antibacterial and antitumor components from H. cuspidatus could benefit further development and utilization of this plant. [Display omitted] • Eighteen terpenoids including six new ones were isolated from Hyssopus cuspidatus. • Most of the compounds showed potent anti-inflammatory activities. • Compound 8 showed strong anti-inflammatory activity against IL-6 and TNF-α. • Several compounds showed good activities against MCF-8, HT-29 and HT-29 cell lines. • Several compounds showed moderate antimicrobial activities. [ABSTRACT FROM AUTHOR]
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- 2023
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22. Seven new meroterpenoids from the fungus Penicillium sclerotiorum GZU-XW03–2.
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Liu, Xia, Zhao, Min, Chen, Jie, Pan, Wen-Cong, Tan, Shao-Li, Cui, Hui, and Zhao, Zhong-Xiang
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TERPENES , *FUNGI , *PLANT extracts , *SPECTRUM analysis - Abstract
Seven previously undescribed meroterpenoids, peniscmeroterpenoids H − N (1 – 7), were isolated from the marine-derived fungus Penicillium sclerotiorum GZU-XW03–2. Their structures were established by the spectroscopic methods and the electronic circular dichroism (ECD) calculations. Peniscmeroterpenoid H was a 6/6/6/5/6 rearranged pentacyclic meroterpenoid, featuring a unique 2-oxaspiro[5.5] undeca-4,7-dien-3-one motif. Peniscmeroterpenoids I and J (2 and 3) owned rare 6(D)/5(E) fused rings were not common in natural products, and compound 2 was the second example of a berkeleyone analogue stripped of the methyl ester fragment. Peniscmeroterpenoid K (4) was the first case where the C-24 was oxidized. In bioassay, compound 5 showed moderate anti-inflammatory activity. [Display omitted] • Peniscmeroterpenoid H possesses a unique 2-oxaspiro[5.5] undeca-4,7-dien-3-one motif with 6/6/6/5/6 pentacyclic skeleton. • Peniscmeroterpenoids I − J owned rare 6(D)/5(E) fused rings were not common in natural. • Peniscmeroterpenoid I was the second example of a berkeleyone analogue stripped of the methyl ester fragment. • Peniscmeroterpenoid K was the first case of berkeleyone where the C-24 was oxidized. [ABSTRACT FROM AUTHOR]
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- 2023
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23. Dimeric 2-(2-phenethyl)chromones from agarwood of Aquilaria filaria.
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Yang, Hong-run, Wang, Pei, Liu, Fang-Zheng, Yuan, Jing-Zhe, Cai, Cai-Hong, Wu, Fei, Jiang, Bei, Mei, Wen-Li, and Dai, Hao-Fu
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TERPENES , *COMPARATIVE studies , *DESCRIPTIVE statistics , *CHROMONES , *PLANT extracts , *NITRIC oxide , *SPECTRUM analysis - Abstract
Four new 2-(2-phenethyl)chromone dimers (1–4) were isolated from EtOAc extract of agarwood originating from Aquilaria filaria from Philippines. Their structures were elucidated by spectroscopic analysis (1D and 2D NMR, and HRESIMS) and comparison of the experimental and computed ECD curves. Compounds 1–4 exhibited inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with IC 50 values in the range from 33.94 to 57.53 μM. [Display omitted] • Four new 2-(2-phenethyl)chromone dimers were isolated from agarwood of Aquilaria filaria from Philippines. • Compound 4 , whose unites A and B were linked via C5-O-C7″-ether bond, was a relative unusual 2-(2-phenethyl)chromone dimer. • Compounds 1–4 exhibited inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells. [ABSTRACT FROM AUTHOR]
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- 2023
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24. COX-2 and iNOS inhibitory abietane diterpenoids from Pinus yunnanensis exudates.
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Liu, Jing, Li, Ji-Jun, Yan, Yong-Ming, Bai, Ming, and Cheng, Yong-Xian
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MEDICINAL plants , *TERPENES , *GUMS & resins , *BIOINFORMATICS , *PLANT extracts , *SPECTRUM analysis - Abstract
Pinuskesiols A–F (1 – 6), six new structurally diverse abietane diterpenoids were isolated from Pinus yunnanensis resins. Their structures including absolute configurations were characterized by using spectroscopic and computational methods. All the compounds bear a carbonyl functionality at C-4 with 1 and 2 behaving as a lactone thereof. The isopropyl group is attached to C-13 via O -atom in 3. In addition, the presence of a Δ 5(6) double bond and a ketone at C-7 makes 2 a large conjugated system. Biological evaluation revealed that 1 , 2 , and 4 could concentration-dependently inhibit iNOS and COX-2 expression in lipopolysaccharide-induced RAW 264.7 cells with 2 to be the most active toward COX-2 inhibition. Pinuskesiols A–F (1 – 6), six new structurally diverse abietane diterpenoids were isolated from Pinus yunnanensis resins. Their structures including absolute configurations were characterized by using spectroscopic and computational methods. All the compounds bear a carbonyl functionality at C-4 with 1 and 2 behaving as a lactone thereof. The isopropyl group is attached to C-13 via O -atom in 3. In addition, the presence of a Δ 5(6) double bond and a ketone at C-7 makes 2 a large conjugated system. Biological evaluation revealed that 1 , 2 , and 4 could concentration-dependently inhibit iNOS and COX-2 expression in lipopolysaccharide-induced RAW 264.7 cells with 2 to be the most active toward COX-2 inhibition. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2023
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25. Spirocyclic polyketides from the marine fungus Talaromyces sp. CX11.
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Cao, Xun, Ge, Yichao, Lan, Donghe, Wu, Xiaodan, and Wu, Bin
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TERPENES , *FUNGI , *POLYKETIDES , *PHYTOCHEMICALS , *SPECTRUM analysis - Abstract
Three new spirocyclic polyketides, talaromyacins A – C, were identified from the endophytic fungus Talaromyces sp. CX11. Their structures including absolute configurations were determined by extensive spectroscopic analysis, Snatzke's method and quantum chemical calculations. Talaromyacin A is identical to the known sequoiamonascin A, for which a structural revision is required. [Display omitted] • Three new spirocyclic polyketides were characterized from Talaromyces sp. CX11. • Snatzke's method and quantum chemical calculations were used for structure determination. • Known compound sequoiamonascin A is structural revised as talaromyacin A. [ABSTRACT FROM AUTHOR]
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- 2023
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26. Solanoids F − I: Terpenoids from Solanum lyratum with neuroprotective effects against H2O2-induced SH-SY5Y cell injuries.
- Author
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Chang, Ye, Lou, Li-Li, Zhang, Xin, Hou, Jiao-Yang, Yao, Guo-Dong, Huang, Xiao-Xiao, Song, Shao-Jiang, Lin, Bin, and Bai, Ming
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TERPENES , *MEDICINAL plants , *OXIDATIVE stress , *GENE expression , *CELLULAR signal transduction , *NEUROPROTECTIVE agents , *GENOMES , *CELL lines , *ONTOLOGIES (Information retrieval) , *HYDROGEN peroxide , *SPECTRUM analysis - Abstract
Four new terpenoids, solanoids F − I (1 – 4), together with eleven known compounds (5 – 15), were isolated from the whole herb of Solanum lyratum. The chemical structures were characterized by spectroscopic techniques, and electronic circular dichroism (ECD) data analysis was adopted to confirm the absolute configurations of 1 – 4. Compounds 1 – 6 , 8 and 12 – 15 exhibited neuroprotective effects against H 2 O 2 -induced oxidative damage of human SH-SY5Y cells. Additionally, this study also combined Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) enrichment analyses to explore the potential targets and signaling pathways of active terpenoids components in intervening Alzheimer's disease (AD). [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2022
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27. Cassaine diterpenoid glycosides from the seeds of Erythrophleum fordii Oliv. and their antiviral and anti-inflammatory activities.
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Zhong, Hao, Wang, Li, Xiong, Si, Wang, Zhen, Chen, Zeping, Huang, Weihuan, Li, Manmei, and Tian, Haiyan
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IN vitro studies , *RESPIRATORY syncytial virus , *TERPENES , *MEDICINAL plants , *VIRUSES , *INFLAMMATION , *GLYCOSIDES , *GENE expression , *SEEDS , *MOLECULAR structure , *SPECTRUM analysis - Abstract
Seven new cassaine diterpenoids (1 – 7) along with four known ones (8 – 11) were isolated from the seeds of Erythrophleum fordii Oliv. (Leguminosae). Their chemical structures were elucidated by extensive spectroscopic data interpretation and chemical methods. Compound 1 is a rare unsymmetrical dimer, which is formed by the linking of another cassaine diterpenoid acid glycoside to the 6-hydroxyl group of the sugar unit in a cassaine amide glycoside through an ester bond. Compound 2 is a cassaine diterpenoid acid derivative featuring an unusual Z double bond at C-13 and C-15. The in vitro antiviral and anti-inflammatory activities of 1 – 11 were evaluated. The results showed that compounds 1 , 2 and 3 showed significant antiviral activities against human respiratory syncytial virus (RSV) with IC 50 s of 6.3, 7.8, and 9.4 μM, respectively. Compound 9 significantly suppressed the expression of nuclear factor-kappa B (NF-κB) with an IC 50 value of 2.6 μM. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2022
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28. Multi-target mechanisms against coronaviruses of constituents from Chinese Dagang Tea revealed by experimental and docking studies.
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Zhao, Liyun, Qin, Xubing, Lin, Tingting, Xie, Fuda, Yao, Liyuan, Li, Yulin, Xiong, Binhong, Xu, Zhifang, Ye, Yongchang, Chen, Hongfeng, and Qiu, Sheng-Xiang
- Subjects
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EXPERIMENTAL design , *COVID-19 , *HERBAL medicine , *MEDICINAL plants , *TERPENES , *FLAVONOIDS , *ANTIVIRAL agents , *PHYTOCHEMICALS , *ELECTRON microscopy , *LEAVES , *FLUORESCENT antibody technique , *TEA , *PLANT extracts , *COMPUTER-assisted molecular modeling , *CHINESE medicine , *SPECTRUM analysis , *PHARMACODYNAMICS - Abstract
The leaves of Eurya chinensis (Chinese Dagang Tea)have been consumed as herbal tea for centuries in Guangdong, China, and have also been used to prevent influenza and treat colds and fevers in traditional Chinese medicine. However, there are no reports on the chemical profile and efficacy of its leaves for the treatment of fever and viral infections. The chemical constituents of Eurya chinensis leaves were isolated and identified by phytochemical study and spectroscopic data, E. chinensis extracts and compounds were evaluated for their antiviral activities by cytopathic effect (CPE) reduction and antibody-based EC 50 assay. The antiviral effect of the main component was confirmed by immunofluorescence and transmission electron microscopy. Virtual screening and docking enzyme inhibition experiments were performed to analyze the anti-coronavirus mechanisms of the compounds from E. chinensis leaves. In this study, we found for the first time that E. chinensis leaf extract exhibited inhibitory effects against coronaviruses HCoV-OC43 in vitro. Among 23 monomer compounds isolated from E. chinensis leaf extract, the triterpenoids (betulinic acid, α-amyrin) and the flavonoids (naringenin, eriodictyol and quercetin) showed marked antiviral activity. Microscopic optical analyses further demonstrated that betulinic acid can remove virus particles from HCoV-OC43 infected cells. Virtual screening and docking analysis towards the coronavirus in vogue revealed that betulinic acid was able to bind well to PLpro and Nsp14N7-MTase, and that the flavonoids prefer to bind with PLpro, Nsp3MES, NspP14N7-MTase, Nsp16GTA, and Nsp16SAM. The enzyme inhibition experiments demonstrated that betulinic acid (1) exhibited significant inhibition of PLpro and N7-MTase activity of SARS-CoV-2. This study proposes E. chinensis and its triterpenoids and flavonoids as promising potential treatments for coronaviruses. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2022
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29. Polyoxygenated cembranoids from the South China Sea soft coral Sarcophyton boettgeri and their stereochemistry.
- Author
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Liu, Jiao, Xu, Ting, Yao, Li-Gong, Li, Song-Wei, and Guo, Yue-Wei
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X-rays , *INVERTEBRATES , *TERPENES , *ORGANIC compounds , *CRYSTALLOGRAPHY , *MOLECULAR structure , *SPECTRUM analysis - Abstract
Four new polyoxygenated cembranoids, namely sarcoboettgerol A (1), 12- epi -humilisin D (2), sarcoboettgerol B (3), and sarcoboettgerol C (4), together with one known related analogue, humilisin D (5), were isolated and characterized from the soft coral Sarcophyton boettgeri collected off Ximao island, Hainan Province, China. The structures and absolute configurations of the new compounds were determined by extensive spectroscopic data analyses, Cu k α single crystal X-ray diffraction analysis, and TDDFT-ECD calculations. A plausible biogenetic relationship of 3 and 4 was proposed. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2022
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30. Structures and antiosteoclastogenic activity of compounds isolated from edible lotus (Nelumbo nucifera Gaertn.) leaves and stems.
- Author
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Vu, Ngoc Khanh, Ha, Manh Tuan, Ha, Young Jun, Kim, Chung Sub, Gal, Minju, Ngo, Quynh-Mai Thi, Kim, Jeong Ah, Woo, Mi Hee, Lee, Jeong-Hyung, and Min, Byung Sun
- Subjects
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MEDICINAL plants , *OSTEOCLASTS , *BONE growth , *TERPENES , *GLYCOSIDES , *NUCLEAR magnetic resonance spectroscopy , *EDIBLE plants , *PHYTOCHEMICALS , *PLANTS , *LEAVES , *PLANT stems , *DESCRIPTIVE statistics , *PLANT extracts , *MOLECULAR structure , *CELL lines , *SPECTRUM analysis - Abstract
One new 1,4-bis-phenyl-1,4-butanedione glycoside (14), one new eudesmane-type sesquiterpenoid (16), and 16 known compounds were isolated from the leaves and stems of Nelumbo nucifera Gaertn. The structures of the isolated compounds were elucidated by interpretation of their 1D and 2D NMR spectroscopic and HRESIMS data. Time-dependent density functional theory calculations and Electronic Circular Dichroism (ECD) spectroscopy was used to determine absolute configurations of the new eudesmane-type sesquiterpenoid (16). All the isolated compounds were examined for their antiosteoclastogenic activity. Preliminarily results of the TRAP staining on RAW 264.7 cells indicated that compounds 1 and 11 possess potential inhibitory effects on RANKL-induced osteoclast formation. Further bioassay investigation was carried out to reveal that compounds 1 and 11 suppressed RANKL-induced osteoclast formation in a concentration-dependent manner with the inhibition up to 55% and 78% at the concentration of 10 μM, respectively. In addition, the structure-activity relationship analysis showed that the 1,3-dioxole substitute and the double bond at C-6a/C-7 in the aporphine skeleton may be responsible for the antiosteoclastogenic activity. The findings provided valuable insights for the discovery and structural modification of aporphine alkaloids as the antiosteoclastogenic lead compounds. [Display omitted] • A phytochemical investigation of Nelumbo nucifera leaves and stems was conducted. • One new 1,4-bis-phenyl-1,4-butanedione glycoside and one new eudesmane-type sesquiterpenoid were identified. • The absolute configurations were determined by experimental ECD and ECD calculations. • Two compounds showed a strong, dose-dependent antiosteoclastogenic activity. [ABSTRACT FROM AUTHOR]
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- 2022
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31. Further sesquiterpenoids from Pittosporum qinlingense and their anti-inflammatory activity.
- Author
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Deng, Ji-Li, Huang, Rong, Zhang, Qiang-Guo, Sha, Bai-Tong, Wang, Min-Chang, Deng, Shang-Yong, Gao, Jin-Ming, and Zhang, Xiu-Yun
- Subjects
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FOLIAR diagnosis , *CARBOXYLIC acids analysis , *IN vitro studies , *MEDICINAL plants , *TERPENES , *NITRIC-oxide synthases , *ANTI-inflammatory agents , *GLYCOSIDES , *NUCLEAR magnetic resonance spectroscopy , *PLANT stems , *FRUIT , *MASS spectrometry , *PLANT extracts , *INFRARED spectroscopy , *NITRIC oxide , *NEUROGLIA , *METABOLITES , *SPECTRUM analysis , *PHARMACODYNAMICS - Abstract
Four new sesquiterpenoid glycoside esters, Pitqinlingoside N - Q (1 – 4), together with eleven known metabolites (5 – 15), were isolated from 95% EtOH extract of the twigs, fruits and leaves of P. qinlingense. The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses, including IR, UV, HRMS, NMR and electronic circular dichroism spectra. Unusal glycoside esters are characterized by the presence of polyacylated β -D-fucopyranosyl and β - d -glucopyranosyl units. Pitqinlingoside N (1), O (2), P (3), boscialin (5) and arvoside C (6) showed significant nitric oxide production inhibition in lipopolysaccharide (LPS)-induced BV-2 microglial cells with IC 50 values ranging from 1.58 to 28.74 μM. Structure-activity relationships of the isolated compounds are discussed. [Display omitted] • P. qinlingense is a new species of Pittosporum , native from Qinling mountains, Shaanxi Province, China. • Four new sesquiterpenoid glycoside esters were isolated from P. qinlingense twigs and leaves. • Pitqinlingoside P (3) showed significant nitric oxide production inhibition in LPS-induced BV-2 microglial cells with IC 50 value 1.58 μM. [ABSTRACT FROM AUTHOR]
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- 2022
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32. Novel geranylhydroquinone derived meroterpenoids from the fungus Clitocybe clavipes and their cytotoxic activity.
- Author
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Hou, Yong, Li, Qinglong, Chen, Meiying, Wu, Haifeng, Yang, Junshan, Sun, Zhaocui, Xu, Xudong, and Ma, Guoxu
- Subjects
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TERPENES , *CELL surface antigens , *PLANT extracts , *CELL lines , *IMMUNODIAGNOSIS , *SPECTRUM analysis - Abstract
Three novel geranylhydroquinone derived meroterpenoids, named clavilactones J and K (1 – 2) and clavipol C (3), were isolated from the basidiomycete Clitocybe clavipes. Their structures were unambiguously identified by extensive spectroscopic data analysis, and the electronic circular dichroism (ECD) calculation, Gauge-Including Atomic Orbitals (GIAO) NMR calculations and Mo 2 (OAc) 4 -induced electronic circular dichroism experiments were used to establish their absolute configurations. Compound 1 , with two epoxy groups located at the 10-membered carbocycle, is uncommon in the reported meroterpenoids from C. clavipes. All the obtained compounds (1–3) were tested for their cytotoxic activity against human tumor cell line HGC-27 by using the MTT assay. All the compounds exhibited moderate cytotoxic activities against HGC-27 cell with IC 50 values ranging from 33.5 to 56.6 μM. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2022
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33. Meroterpenoids with a large conjugated system from Ganoderma lucidum and their inhibitory activities against renal fibrosis.
- Author
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Wang, Yong-Xiang, Peng, Yun-Li, Qiu, Bin, Lv, Qing, Huang, Li-Shu-Xin, and Cheng, Yong-Xian
- Subjects
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FIBRONECTINS , *TERPENES , *MEDICINAL plants , *HIGH performance liquid chromatography , *ANIMAL experimentation , *GROWTH factors , *RATS , *PLANT extracts , *SPECTRUM analysis , *PHOSPHORYLATION - Abstract
Baoslingzhines A – E (1–5), five new meroterpenoids were isolated from the fruiting bodies of Ganoderma lucidum. The structures including their absolute configurations were characterized by using spectroscopic and computational methods. Compound 1 is a novel trinormeroterpenoid featuring the presence of an unusual dihydronaphthalene representing an unprecedented meroterpenoid skeleton. Compounds 2–4 are mononormeroterpenoids characteristic of a large conjugated system. Among them, racemic 3 and 4 were separated by HPLC on chiral phase. Biological evaluation toward kidney fibrosis found that compounds 2 and (+) -3 could inhibit the expression of fibronectin and collagen I dose dependently in TGF- β 1-induced rat kidney proximal tubular cells (NRK-52e). Additionally, (+) -3 could also down regulate ɑ -SMA in a concentration dependent manner. Further investigation showed that 2 could inhibit Smad2 phosphorylation. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2022
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34. Anti-inflammatory sesquiterpenoid dimers from Artemisia atrovirens.
- Author
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Shao, Zhengguang, Li, Lizhi, Zheng, Yongzhe, Gong, Qi, Ke, Chang-Qiang, Yao, Sheng, Zhang, Haiyan, Tang, Chunping, and Ye, Yang
- Subjects
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TERPENES , *ANTI-inflammatory agents , *GAS chromatography , *MASS spectrometry , *PLANT extracts , *MOLECULAR structure , *SPECTRUM analysis , *PHARMACODYNAMICS - Abstract
Eight new sesquiterpenoid dimers, artatrovirenolides A-H (1–8), along with three known analogues (9–11), were isolated from Artemisia atrovirens by using the LC-MS guided isolation. Compound 1 was a compound dimerized from a guaianolide and a 1,10- seco -guaianolide unit while others were from two guaianolide units. Their structures were established by comprehensive analysis of spectroscopic data, and their absolute configurations were determined by the aid of time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculation. Compound 8 showed anti-inflammatory effect in LPS-stimulated BV-2 microglial cells at 1 μM, while compounds 1 , 2 , 5 , and 6 inhibited microglial inflammation at 10 μM. [Display omitted] • Eight new sesquiterpenoid dimers were characterized from Artemisia atrovirens. • All compounds were Diels-Alder adducts, but possessing different linkage patterns such as 1,4-, or 2,5-linkage. • The absolute configurations of new compounds were determined by TDDFT ECD calculations. • Some compounds showed anti-inflammatory effect in LPS-stimulated murine microglial BV-2 cells at 1 or 10 μM. [ABSTRACT FROM AUTHOR]
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- 2022
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35. Monoterpene indole N-oxide alkaloids from Tabernaemontana corymbosa and their antimicrobial activity.
- Author
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Fan, Kun, Ding, Cai-Feng, Deng, Shi-Yu, Gao, Wen, Tan, Bang-Yin, Wu, Hao, Guo, Ying, Song, Jing-Feng, Zhang, Lan-Chun, Zhang, Rong-Ping, and Yu, Hao-Fei
- Subjects
- *
PHYTOTHERAPY , *TERPENES , *INDOLE compounds , *ANTI-infective agents , *TRADITIONAL medicine , *STAPHYLOCOCCAL diseases , *BARK , *PLANT stems , *STAPHYLOCOCCUS aureus , *MOLECULAR structure , *SPECTRUM analysis ,THERAPEUTIC use of alkaloids - Abstract
Tabernaemontana corymbosa is a traditional folk medicine. In our research, six monoterpene indole N -oxide alkaloids and their parent alkaloids were obtained from the stem bark of T. corymbosa , including seven new alkaloids (1 – 7) and five known alkaloids (8 – 12). Their structures and absolute configurations were elucidated by extensive spectroscopy, quantum chemical calculations, and DP4+ probability analyses. The antimicrobial activity of the obtained compounds was evaluated, among which alkaloids 4 , 8 , 12 showed significant antimicrobial activity against Staphylococcus aureus with an MIC value of 6.25 μ g/mL, while alkaloids 11 , 12 showed moderate antimicrobial activity against Bacillus subtilis with an MIC value of 25 μ g/mL. [Display omitted] • Six N -oxide MIAs and their parent alkaloids were isolated from T. corymbosa. • Compounds 1 – 7 were identified to be new MIAs. • Alkaloid 1 was determined by quantum chemical calculations, and DP4+ analysis. • The antimicrobial activity of all MIAs was evaluated and discussed their differences. [ABSTRACT FROM AUTHOR]
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- 2022
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36. Discovery of ent-kaurane diterpenoids, characteristic metabolites of Isodon species, from an endophytic fungal strain Geopyxis sp. XY93 inhabiting Isodon parvifolia.
- Author
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Xia, Jiang-Nan, Hu, Kun, Su, Xiao-Zheng, Tang, Jian-Wei, Li, Xiao-Nian, Sun, Han-Dong, and Puno, Pema-Tenzin
- Subjects
- *
TERPENES , *MEDICINAL plants , *FUNGI , *PHYTOCHEMICALS , *PLANT extracts , *CELL lines , *SPECTRUM analysis , *CYTOTOXINS - Abstract
Isogeopyxins A–C (1 – 3), three new diterpenoids with ent -kaurane, ent -pimarane, and ent -abietane scaffolds, respectively, along with six known ent -kauranoids, were isolated from the fermentation culture of Geopyxis sp. XY93 inhabiting the leaves of Isodon parvifolia. Their structures were elucidated by interpretation of spectroscopic data, and single crystal X-ray diffraction. It marks the first time that ent -kauranoids, characteristic metabolites of Isodon species, have been isolated from an associated endophytic fungus. [Display omitted] • Chemical investigation on endophytic Geopyxis sp. XY93 of Isodon parvifolia led to the discovery of 9 diterpenoids. • Characteristic metabolites of Isodon species were isolated from an associated endophytic fungus for the first time. • ent -Kauranoids from Geopyxis sp. XY93 exhibited good cytotoxic effects against liver cancer cells. [ABSTRACT FROM AUTHOR]
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- 2022
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37. New phenylpropanoids and monoterpene alkaloids with vasorelaxant activities from the branches of Alstonia scholaris.
- Author
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Zhang, Fuxin, Liu, Huanhuan, Yang, Kailing, Yang, Tao, Zhou, Ruixi, Miao, Rongkun, Zhan, Guanqun, and Guo, Zengjun
- Subjects
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BIOLOGICAL models , *MEDICINAL plants , *TERPENES , *ANIMAL experimentation , *RATS , *VASODILATORS , *DESCRIPTIVE statistics , *SPECTRUM analysis ,THERAPEUTIC use of alkaloids ,THERAPEUTIC use of plant extracts - Abstract
Two new phenylpropanoids (1 – 2), one new nor-monoterpenoid alkaloid (3), one new monoterpene alkaloid (4), together with nine known compounds (5 – 13) were obtained from the branches of Alstonia scholaris. The structures of the undescribed compounds were determined by extensive spectroscopic analysis. Alkaloid 3 represented the first example of C-4 methylated nor-monoterpenoid alkaloids. A possible biosynthetic pathway for this new type of monoterpene alkaloids was proposed. All the isolates were evaluated for vasorelaxant activity against phenylephrine-induced contraction of rat mesenteric arteries. Compounds 1 , 4 , 9 , 12, and 13 showed significant vasorelaxant activity with relaxation rates above 90% at 200 μM and exhibited moderate vasorelaxant activity with IC 50 values ranging from 41.87 to 93.30 μM by further studies. It was the first report on the potential vasorelaxant activity of monoterpene alkaloids. Monoterpene alkaloids 3 and 4 may be served as the potential lead compounds for the discovery of vasodilators, due to their simple and optimizable structures. [Display omitted] • Four new compounds were isolated from Alstonia scholaris. • Alkaloid 3 was the first C-4 methylated nor-monoterpenoid alkaloid. • 1 , 4 , and 9 showed significant vasorelaxant activity with relaxation rates above 90% at 200 μM. • It is the first reported potential vasorelaxant activity of monoterpene alkaloids. [ABSTRACT FROM AUTHOR]
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- 2022
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38. Anti-inflammatory and analgesic monoterpenoid indole alkaloids of Kopsia officinalis.
- Author
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Jin, Qiong, Zhao, Yun-Li, Liu, Ya-Ping, Zhang, Ruo-Song, Zhu, Pei-Feng, Zhao, Lan-Qin, Qin, Xu-Jie, and Luo, Xiao-Dong
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LIPOPOLYSACCHARIDES , *INTERLEUKINS , *CYCLOOXYGENASE 2 , *MEDICINAL plants , *TERPENES , *ALKALOIDS , *ANTI-inflammatory agents , *ANALGESICS , *ANIMAL experimentation , *NONSTEROIDAL anti-inflammatory agents , *ORGANIC compounds , *PHYTOCHEMICALS , *BARK , *LEAVES , *TUMOR necrosis factors , *PLANT extracts , *CHROMATOGRAPHIC analysis , *MICE , *SPECTRUM analysis - Abstract
"Ya gai", an important part of Dai medical theory, is traditionally recognized as an antidote. Kopsia officinalis Tsiang et P. T. Li is a "Ya gai" related medicine and has been widely used by Dai people for the treatment of pain and inflammation. Previous literature on title species suggested that monoterpenoid indole alkaloids (MIAs) could be its main bioactive components. However, the specific bioactive ingredients for inflammation-related treatment are still unrevealed, which inspired us to conduct a phytochemical and pharmacological investigation related to its traditional use. To support the traditional use of K. officinalis by assessing the anti-inflammatory and analgesic effects of its purified MIAs. Compounds were isolated and purified from the barks and leaves of K. officinalis using diverse chromatographic methods. The structures were established by means of extensive spectroscopic analyses and quantum computational technique. The anti-inflammatory activities of the purified MIAs were evaluated in vitro based on the suppression of lipopolysaccharide-activated inflammatory mediators (COX-2, IL-1 β , and TNF- α) in RAW 264.7 macrophage cells. Anti-inflammatory and analgesic activities in vivo were assessed with carrageenan-induced paw edema and acetic acid-stimulated writhing in mice models. 23 MIAs including four new compounds were obtained and structurally established. Most of isolates showed significant anti-inflammatory effects in vitro by inhibiting inflammatory mediators (COX-2, IL-1 β , and TNF- α). Further pharmacological evaluation in vivo revealed that 12-hydroxy-19(R)-hydroxy-ibophyllidine (1) and 11,12-methylenedioxykopsinaline N 4-oxide (5) remarkably decreased the number of writhing, while kopsinic acid (8), (−)-kopsinilam (12), and normavacurine-21-one (20) significantly relieved paw edema, respectively, even better than the positive control aspirin. The in vitro and in vivo findings supported the traditional use of K. officinalis with respect to its anti-inflammatory and analgesic effect, as well as provided potent bioactive MIAs for further chemical modification and pharmacological investigation. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2022
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39. New ent-Kaurane and cleistanthane diterpenoids with potential cytotoxicity from Phyllanthus acidus (L.) Skeels.
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Xin, Ying, Xu, Jia, Lv, Jun-Jiang, Zhu, Hong-Tao, Wang, Dong, Yang, Chong-Ren, and Zhang, Ying-Jun
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MEDICINAL plants , *TERPENES , *ANTI-inflammatory agents , *PLANT roots , *PLANT stems , *PLANT extracts , *CYTOTOXINS , *SPECTRUM analysis - Abstract
Six diterpenoids including three ent -kauranes (1 – 2 , 4) and three cleistanthanes (3 , 5 – 6) were isolated from the roots and stems of Phyllanthus acidus (L.) Skeels. Of them, (16 S)- ent -16,17,18-tri-hydroxy-19-nor-kaur-4-en-3-one (1), phyllanthone A (2), and 6-hydroxycleistanthol (3) are new compounds, while the ent -kaurane diterpenoids were reported from the titled plant for the first time. Their structures were elucidated on the basis of the extensive spectroscopic analyses. Compounds 2 and 4 – 6 displayed cytotoxic potential with IC 50 values ranging from 1.96 to 29.15 μM. They also showed moderate anti-inflammatory activities (IC 50 = 6.30–12.05 μM). Particularly, the new ent -kaurane 2 displayed cytotoxic potential against HL-60 (IC 50 = 2.00 μM) and MCF-7 (IC 50 = 3.55 μM) cells, and anti-inflammatory activity (IC 50 = 6.47 μM). [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2022
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40. Eurobusones A-D, four antibacterial formyl phloroglucinol meoterpenoids from Eucalyptus robusta.
- Author
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Liu, Rui, Liu, Xiang-Yue, Li, Min, Liu, Juan, Yang, Ming-Hua, and Kong, Ling-Yi
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TERPENES , *EUCALYPTUS , *BACILLUS (Bacteria) , *STAPHYLOCOCCUS aureus , *DOSE-effect relationship in pharmacology , *PLANT extracts , *MOLECULAR structure , *PSEUDOMONAS , *ANTIBIOTICS , *SPECTRUM analysis , *PHARMACODYNAMICS - Abstract
Four antibacterial formyl phloroglucinol meroterpenoids (FPMs), eurobusones A-D (1–4), as well as six known analogues (5–10), were isolated from the leaves of Eucalyptus robusta. Their structures were determined by the analysis of spectroscopic data and electron circular dichroism (ECD) calculation, along with the application of Snatzke helicity rules. Among them, compounds 2 and 8 – 10 showed good activity against Staphylococcus aureus , Pseudomonas aeruginosa and Bacillus subtilis with MIC 50 values less than 1.00 μg/mL. [Display omitted] • Four formyl phloroglucinol meroterpenoids (1 – 4) were isolated from Eucalyptus robusta. • Their absolute configurations were determined by the electron circular dichroism calculation and the Snatzke helicity rules. • All isolates showed activity against Staphylococcus aureus , Pseudomonas aeruginosa and Bacillus subtilis. [ABSTRACT FROM AUTHOR]
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- 2022
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41. Monoterpene indole alkaloids from Melodinus cochinchinensis (Lour.) Merr.
- Author
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Wang, Xiao-Feng, Wei, Ren-Jie, Fang, Qiang-Qiang, He, Wan-Ying, Jiang, Kun, Qu, Shi-Jin, Tan, Jun-Jie, and Tan, Chang-Heng
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TERPENES , *INDOLE compounds , *MEDICINAL plants , *ALKALOIDS , *PLANT anatomy , *PLANT extracts , *SPECTRUM analysis - Abstract
Melodicochinines A – D (1 – 4), four new monoterpene indole alkaloids (MIAs), along with 21 known ones, were isolated from the stems and twigs of Melodinus cochinchinensis. Their structures were elucidated on the basis of extensive spectroscopic analysis. A ubiquitin-rhodamine 110 assay showed that 11-methyloxytabersonine had potential inhibitory effect against ubiquitin-specific protease 7 (USP7). [Display omitted] • 25 MIAs were isolated from the stems and twigs of Melodinus cochinchinensis. • Melodicochinines A – D were identified to be new MIAs. • Three proposed 16β-hydroxylated vindolinine-type MIAs were revised to 16α-hydroxylated ones. • 11-methyloxytabersonine showed 59% inhibitory effect on USP7 at the concentration of 5 μM. [ABSTRACT FROM AUTHOR]
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- 2022
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42. 21,24-Cyclolanostanes revisited: Structural revision and biological evaluation.
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Wang, Chao, Wang, Lirong, Wang, Jilong, Li, Yu-Peng, Zhang, Jun-Sheng, Shan, Peipei, and Zhang, Hua
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IN vitro studies , *TERPENES , *FUNGI , *NUCLEAR magnetic resonance spectroscopy , *CRYSTALLOGRAPHY , *TOXICITY testing , *CELL proliferation , *MOLECULAR structure , *CELL lines , *BIOLOGICAL assay , *SPECTRUM analysis - Abstract
Chemical fractionation of the EtOH extract of a medicinal macro fungus, Inonotus obliquus , afforded an array of lanostane-type triterpenoids (1 − 11) including two new ones (1 and 8). The structures of these compounds were determined on the basis of spectroscopic analyses, single crystal X-ray crystallography of 3 – 6 and biosynthetic considerations. With the confirmatory structural information provided by X-ray diffraction analysis in hand, several previously reported 21,24-cyclolanostanes, such as inonotsutriols A–C and (20 R ,21 S ,24 S)-21,24-cyclopenta-3 β ,21,25-trihydroxylanosta-8-ene, were structurally corrected. In addition, the NMR data of other types of 21,24-cyclo triterpenoids were also re-examined and structural revisions were thus suggested. Compounds 2 , 6 and 8 showed significant cytostatic effects against a panel of tumor cell lines with IC 50 values ranging from 7.80 to 18.5 μM. Further assays established that compound 2 exerted promising in vitro anti-breast cancer potential by inhibiting the proliferation and migration of 4T1 cells. [Display omitted] • Two new lanostane-type triterpenoids were isolated from fungus Inonotus obliquus. • The absolute configurations were characterized by single-crystal X-ray diffraction. • The structures of several previously reported 21,24-cyclolanostanes were corrected. • Selective compounds showed cytotoxicity against lung, breast & gastric tumor cells. • Compound 2 dose-dependently inhibited the proliferation and migration of 4 T1 cells. [ABSTRACT FROM AUTHOR]
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- 2022
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43. Ten undescribed cadinane-type sesquiterpenoids from Eupatorium chinense.
- Author
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Chen, Ziang, Ke, Chang-Qiang, Zhou, Shuaizhen, Feng, Lu, Tang, Chunping, and Ye, Yang
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TERPENES , *HERBAL medicine , *MAGNETIC resonance imaging , *PLANT extracts , *CHINESE medicine , *SPECTRUM analysis - Abstract
Ten undescribed cadinane-type sesquiterpenes (1 − 10) were isolated from the whole plant of Eupatorium chinense. Their planar structures were mainly elucidated by extensive analysis of spectroscopic data and DFT NMR calculations. The absolute configurations of 1 , 2 , and 3 were determined by TDDFT ECD calculations while those of compounds 4 – 7 and 9 were confirmed by single crystal X-ray diffraction experiments. Compounds 2 and 3 are a pair of C-10 epimers, compounds 4 and 5 a pair of C-1 epimers, and compounds 9 and 10 a pair of compounds isomerized at both C-1 and C-10. A possible biosynthetic pathway for these new sesquiterpenes was proposed. [Display omitted] [ABSTRACT FROM AUTHOR]
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- 2022
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44. Further terpenoids from the Chloranthaceae plant Chloranthus multistachys and their anti-neuroinflammatory activities.
- Author
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Wang, Xue-Jiao, Yu, Sheng-Zhou, Xin, Jun-Li, Pan, Li-Long, Xiong, Juan, and Hu, Jin-Feng
- Subjects
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LIPOPOLYSACCHARIDES , *TERPENES , *MEDICINAL plants , *ANTI-inflammatory agents , *ANIMAL experimentation , *PHYTOCHEMICALS , *PLANT extracts , *NITRIC oxide , *MICE , *SPECTRUM analysis , *PHARMACODYNAMICS - Abstract
Three labdane-type [multisins A–C (1 – 3)], two guaiane-type [multisins D (4) and E (5)], and one eudesmane-type [multisin F (6)] previously undescribed terpenoids, together with 14 mono- (7 – 20) and seven dimeric- (21 – 27) known terpenoids, were isolated from the 90% MeOH extract of the whole plant of Chloranthus multistachys. Their structures and absolute configurations were determined by extensive spectroscopic methods and electronic circular dichroism (ECD) calculations. Compounds 4 and 5 are rare trinor-sesquiterpenes with a de-isopropyl guaiane skeleton, whereas compound 6 is a rearranged dinor-eudesmene featuring an uncommon octahydro-1 H -indene ring system. Among the isolates, the dimeric lindenane sesquiterpenoid shizukaol C (25) exhibited the most potent (IC 50 = 8.04 μM) anti-neuroinflammatory activity by inhibiting the nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine BV-2 microglial cells. [Display omitted] • A phytochemical reinvestigation on the herb Chloranthus multistachys was reported. • Six previously undescribed di−/sesqui-terpenoids (multisins A–F) were identified. • Multisins D/E are rare trinor-sesquiterpenes with a de-isopropyl guaiane skeleton. • Multisin F is an unusual dinor-eudesmane featuring a rearranged ring system. • Shizukaol C exhibited relatively the most potent anti-neuroinflammatory activity. [ABSTRACT FROM AUTHOR]
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- 2022
- Full Text
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45. Anti-inflammatory and hepatoprotective cembranoid alcohols from the Gum Resin of Boswellia carterii.
- Author
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Yu, Jinqian, Zhao, Lei, Zhang, Kewei, and Wang, Xiao
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IN vitro studies , *TERPENES , *LIVER tumors , *LIVER , *ANTI-inflammatory agents , *GUMS & resins , *ANTINEOPLASTIC agents , *MACROPHAGES , *DESCRIPTIVE statistics , *PLANT extracts , *MOLECULAR structure , *CELL lines , *SPECTRUM analysis , *PHARMACODYNAMICS - Abstract
Five undescribed cembranoid alcohols, boscartinols A-E (1–5) were discovered from the gum resin of Boswellia carterii. Their structures were elucidated by analyzing the spectroscopic data. Notably, all these five compounds preserved an isopropyl type cembranoid skeleton, featured the same groups of one epoxy ring at C 1 -C 12 and one hydroxy group at C-11, as well as two double bonds migrating from C 3 to C 9 and one hydroxy group from C 3 to C 8 within the cembranoid structure. These cembranoids were evaluated for the hepatoprotective and anti-inflammatory activities using two cell models of APAP-induced HepG2 and LPS-induced RAW 264.7. For hepatoprotective activity, compounds 1 and 5 showed remarkable hepatoprotective activity (inhibition rate of 51.6% and 39.8%, respectively) at 10 μM, with the other three compounds of 2 – 4 showing less potently hepatoprotective. For anti-inflammatory activity, compounds 2 – 4 showed significant inhibitory effects on NO produced by LPS-induced RAW 264.7 cell (IC 50 values of 13.40 μM, 7.08 μM and 14.26 μM), with the other two compounds of 1 and 5 showing less potently anti-inflammatory activities. [Display omitted] [ABSTRACT FROM AUTHOR]
- Published
- 2021
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46. Two new scopadulane diterpenoids from Scoparia dulcis attenuated palmitate-induced viability in MIN6 cells.
- Author
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Dong, Lin, Sun, Wanying, Huang, Zibao, Zhang, Caiyun, Liu, Chenpeng, Zhang, Xiaopo, and Zhang, Shouwen
- Subjects
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MEDICINAL plants , *TERPENES , *ACIDS , *CELL survival , *TOMOGRAPHY , *CRYSTALLOGRAPHY , *PLANT extracts , *CELL lines , *MOLECULAR structure , *FATTY acids , *SPECTRUM analysis - Abstract
Two new scopadulane diterpenoids, termed Scopadulcic acids D (1, SDD) and E (2, SDE), together with two known analogues (3 and 4) were isolated from Scoparia dulcis. Their structures were elucidated by comprehensive spectroscopic analysis. The absolute configurations of 1 and 2 were determined by calculated electronic circular dichroism (ECD). Meanwhile, X-ray crystallographic analysis was applied to determine the absolute configuration of 1. All compounds were tested for their effect on attenuating palmitate-induced viability at the concentrations of 25 and 50 μM. The results showed that they significantly attenuated the palmitate-induced viability in MIN6 cells. [Display omitted] [ABSTRACT FROM AUTHOR]
- Published
- 2021
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47. Sesquiterpenes from Artemisia Sieversiana and their anti-inflammatory activities.
- Author
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Nuermaimaiti, Muaitaer, Turak, Ablajan, Yang, Qing, Tang, Bixi, Zang, Yi, Li, Jia, and Aisa, Haji Akber
- Subjects
- *
INTERLEUKINS , *LIPOPOLYSACCHARIDES , *TERPENES , *ANTI-inflammatory agents , *PLANT anatomy , *NUCLEAR magnetic resonance spectroscopy , *WORMWOOD , *TUMOR necrosis factors , *MASS spectrometry , *CELL lines , *SPECTRUM analysis - Abstract
Eight undescribed sesquiterpenes, including three dimeric guaianolides and five sesquiterpens, together with ten known ones, were isolated from the aerial parts of Artemisia sieversiana. Their structures were elucidated by extensive spectroscopic techniques and ECD calculation. The isolated compounds were tested for their anti-inflammatory effects against IL-1β, IL-6 and TNF-α in LPS-induced RAW 264.7 cells. Compounds 4 , 9 , 12 , 15 , 16 and 17 showed potent anti-inflammatory activities. [Display omitted] • Eight undescribed sesquiterpenes, including three dimeric guaianolides and five sesquiterpens, together with ten known compounds were isolated and characterized. • The structures were established based on the 1D, 2D-NMR, HR-ESI-MS and ECD spectroscopic analysis. • The anti-inflammatory activities of the isolates were evaluated. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
48. Ten new nortriterpenes from Euphorbia resinifera and their anti-tomato yellow leaf curl virus activities.
- Author
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Zhao, Ning-Dong, Li, Yu-Lin, Song, Yu, Yang, Bao-Jia, Ding, Xiao, Gao, Fang, Ye, Jian, Hao, Xiao-Jiang, Zhang, Yu, and Li, Shun-Lin
- Subjects
- *
MEDICINAL plants , *TERPENES , *ANTIVIRAL agents , *LEAVES , *TOMATOES , *SPECTRUM analysis - Abstract
Ten new nortriterpenes, euphorbiumrins A-J (1 − 10), together with three known analogues (11 − 13) were isolated from the latex of Euphorbia resinifera. Their structures were established on the basis of extensive spectroscopic analyses (IR, UV, HRESIMS, 1D and 2D NMR). Their inhibitions on tomato yellow leaf curl virus (TYLCV) were evaluated and compound 5 exhibited significant anti-TYLCV activity with an inhibition rate of 71.7% at concentration of 40 μg/mL. [Display omitted] [ABSTRACT FROM AUTHOR]
- Published
- 2021
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49. Polyprenylated acylphloroglucinol meroterpenoids with PTP1B inhibition from Hypericum forrestii.
- Author
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Zong, Jian-Fa, Zhang, Meng-Meng, Zhou, Yu-Bo, Li, Jia, Hou, Ai-Jun, and Lei, Chun
- Subjects
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MEDICINAL plants , *TERPENES , *CELLULAR signal transduction , *GENE expression , *PROTEIN-tyrosine kinases , *PLANT extracts , *TYROSINE , *SPECTRUM analysis , *CHEMICAL inhibitors - Abstract
Three new polyprenylated acylphloroglucinol meroterpenoids, hyperiforins A–C (1 – 3), were isolated from Hypericum forrestii (Chittenden) N. Robson, together with twelve known analogues (4 – 15). Their structures were established by extensive physical and spectroscopic data analysis. Compounds 1 , 2 , 5 , 7 , and 13 – 15 showed potent inhibitory effects on protein tyrosine phosphatase 1B with IC 50 values from 6.63 ± 2.40 to 14.21 ± 3.51 μ M. [Display omitted] • Three new polyprenylated acylphloroglucinol meroterpenoids, hyperiforins A–C (1 – 3), together with twelve known congeners (4 – 15) were isolated from Hypericum forrestii (Chittenden) N. Robson. • The putative biosynthetic pathways for the tertiary hydroperoxyl group in 2, 3, 5, 9, 11, and 12 have been proposed for the first time. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
50. Chemical constituents from Tinospora sagittata and their biological activities.
- Author
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Xu, De-Feng, Miao, Lei, Wang, Yin-Yin, Zhang, Jun-Sheng, and Zhang, Hua
- Subjects
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IN vitro studies , *MEDICINAL plants , *TERPENES , *STEROIDS , *GLYCOSIDES , *PLANT extracts , *MOLECULAR structure , *SPECTRUM analysis - Abstract
Six undescribed low-polarity compounds including three rare 14-methylergostane steroids (1 – 3), one euphane triterpenoid (4) and two octadecanoic acid ethyl esters (5 and 6), along with ten previously reported terpenyl cometabolites (7 – 16), were isolated from the stems of Tinospora sagittata. Their structures were determined by detailed spectroscopic analyses and comparison with structurally related known compounds, and all of them have been reported from T. sagittata for the first time. Compounds 4 – 6 and 16 showed potent in vitro inhibitory activity against the diabetes target α -glucosidase, while compounds 10 and 14 displayed promising antibacterial effect toward Staphylococcus aureus ATCC 25923. [Display omitted] • New 14-methylergostane steroids, euphane triterpenoid and octadecanoid derivatives were separated from Tinospora sagittata. • All the compounds have been reported from Tinospora sagittata for the first time. • Compounds 4 – 6 and 16 showed potent α-glucosidase inhibitory activity. • Compounds 10 and 14 exerted promising antibacterial effect toward Staphylococcus aureus. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
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