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Five undescribed meroterpenoids, baosglucidnes A − E (1 – 5), were isolated from the fruiting bodies of Ganoderma lucidum. Among them, baosglucidne B (2) as a racemic mixture was obtained. Chiral HPLC was employed to separate a pair of enantiomers (+)- 2 and (−)- 2. The structures and stereochemical features of these substances were characterized by utilizing spectroscopic data and ECD calculations. Finally, the results of anti-renal fibrosis activity evaluation showed that baosglucidne E (5) could inhibit the expression of collagen I in TGF- β 1-induced rat kidney proximal tubular cells at 20 μM. [Display omitted] [ABSTRACT FROM AUTHOR]

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]

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]

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]

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]

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]

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]

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]

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]

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]

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]

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]

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]

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]