Search

The Hippophae rhamnoides L. pomace was generated in the production process for juice, wine of food industry. To expand the application of pomace, the extraction process optimization, enrichment and identification of triterpene acids were performed in this study. The extraction yield was 14.87% under optimal ultrasound-assisted extraction techniques performed via response surface methodology. The extract was subsequently purified to obtain the triterpenoid acid enrichment fraction (TPF) with the content of 75.23% ± 1.45%. 13 triterpenoid acids were identified via UPLC-Triple-TOF MS/MS and further semi-quantified through comparison with triterpenoid acid standards. TPF exhibited a strong inhibitory effect on α-glucosidase with IC 50 value of 5.027 ± 0.375 μg/mL, as determined via enzyme inhibition experiment and molecular docking. Additionally, the TPF significantly reduced postprandial glucose levels, as revealed via carbohydrate tolerance tests, as well as ameliorate serum lipid profiles. Therefore, pomace may be a promising resource of functional food components with therapeutic and commercial values. [Display omitted] • The triterpene acid extraction process of sea buckthorn pomace was optimized by RSM. • A total of 13 triterpene acids of TPF were identified. • The effect of inhibiting α-glucosidase was conducted. • The hypoglycemic activity was confirmed by PBG and serum lipid profiles. [ABSTRACT FROM AUTHOR]

Mesonaprocumbens Hemsley is a plant conventionally processed to provide popular food materials and herbal medicines in Asia. In this study, six triterpene acids, including five new ones (mesonaic acids D-H, 1–5), and one proximadiol-type sesquiterpene (7) were isolated from the methanolic extract of the air-dried M. procumbens. Chemical structures of 1‒7 were established by spectroscopic methods, especially 2D NMR techniques (1H–1H COSY, HSQC, HMBC, and NOESY) and HRESIMS. Concerning their biological activities, compounds 1, 2, 6, and 7 were examined manifesting high inhibition toward the pro-inflammatory NO production with EC50 values ranging from 12.88 to 21.21 µM, outrunning the positive control quercetin (24.12 µM). The mesoeudesmol B (7) identified from M. procumbens is the very first example, which exhibited high anti-inflammatory activity diminishing the level of the lipopolysaccharide-induced NO in RAW264.7 macrophage cells, thereby suppressing the secretion of pro-inflammatory cytokines TNF-α and IL-6 and the level of two critical downstream inflammatory mediators iNOS and COX-2.

A number of iridoids and triterpene acids, such as pulchelloside, sesamoside, shanshiside methyl ester, barlerin, gypsogenin acid and acetate of gypsogenic acid were isolated from the aerial part of Phlomis linearifolia and their structures were confirmed by NMR, mass and IR spectroscopy. In addition, the hepatoprotective potential of iridoid fraction from P. linearifolia aerial parts was tested against CCl4 induced fibrosis in rats. The iridoid fraction not only prevented the manifestation of the hepatotoxic effect of CCl4, but rather quickly eliminated the effects of developing intoxication. The hepatoprotective activity of the SI was confirmed to be effective and exceeds knows drug carsil. Supplemental data for this article can be accessed at . [ABSTRACT FROM AUTHOR]

A total of seven compounds, including four triterpene acids and three triterpene lactones, were isolated from the ethanolic extract of the roots of Astilbe grandis Stapf ex Wils. Two of the triterpene lactones (1-2) were never reported before and compounds 3-5 were isolated for the first time from the plant. The structures of these compounds were all identified by spectroscopic analysis. Compounds 1-2 were analyzed by 2D NMR and their absolute configurations were determined using experimental CD in comparison with calculated ECD values. The structure of compound 1 was also further confirmed by single crystal X-ray diffraction analysis. The cytotoxicity of compounds 1-7 on A549, Caco-2, H460 and Skov-3 tumor cells were all evaluated using CCK-8. They all exhibited positive inhibitory effects on Caco-2 tumor cells with IC 50 less than10 μM, while the inhibitory effects on H460 tumor cells were more moderate. Unfortunately, they displayed little apparent cytotoxicity to the other two types of cells., (© 2024 Wiley‐VHCA AG, Zurich, Switzerland.)

Age-related diseases, such as osteoarthritis, Alzheimer’s disease, diabetes, and cardiovascular disease, are often associated with chronic unresolved inflammation. Neutrophils play central roles in this process by releasing tissue-degenerative proteases, such as cathepsin G, as well as pro-inflammatory leukotrienes produced by the 5-lipoxygenase (5-LO) pathway. Boswellic acids (BAs) are pentacyclic triterpene acids contained in the gum resin of the anti-inflammatory remedy frankincense that target cathepsin G and 5-LO in neutrophils, and might thus represent suitable leads for intervention with age-associated diseases that have a chronic inflammatory component. Here, we investigated whether, in addition to BAs, other triterpene acids from frankincense interfere with 5-LO and cathepsin G. We provide a comprehensive analysis of 17 natural tetra- or pentacyclic triterpene acids for suppression of 5-LO product synthesis in human neutrophils. These triterpene acids were also investigated for their direct interference with 5-LO and cathepsin G in cell-free assays. Furthermore, our studies were expanded to 10 semi-synthetic BA derivatives. Our data reveal that besides BAs, several tetra- and pentacyclic triterpene acids are effective or even superior inhibitors of 5-LO product formation in human neutrophils, and in parallel, inhibit cathepsin G. Their beneficial target profile may qualify triterpene acids as anti-inflammatory natural products and pharmacological leads for intervention with diseases related to aging. [ABSTRACT FROM AUTHOR]

In the current investigation, new monomers of myrrhanone B and lupeolic acid were prepared via reaction of triterpenic acids with linkers in the presence of K 2 CO 3 . In addition, new bis-myrrhanone B homodimers, myrrhanone B-myrrhanol B heterodimers, and bis-myrrhanone β-boswellic acids heterodimer were prepared. Evaluation of these compounds on the proliferation of four different human cancer cell lines, viz., FaDu (pharynx carcinoma), A2780 (ovarian carcinoma), HT29 (colon adenocarcinoma) and A375 (malignant melanoma) has been performed. It is worth mentioning that compounds 4 , 7 , 8 , 10 , and 11 possess potent antiproliferative effect towards HT29 cancer cells with IC 50 values of 8.1 μM, 5.4 μM, 8.8 μM, 6.8 μM, and 8.2 μM, respectively. In addition, these compounds display good to moderate antiproliferative activities towards A2780 and A375 with IC 50 values ranging from 10.4 to 24.2 μM. Moreover, the molecular docking studies of most active compounds ( 4, 7, 8, 10 and 11 ) with six anti-cancer drug targets DHFR, VEGFR2, HER-2/neu, CDK6, hCA-IX and LOX also carried, in order to know the mode of binding interaction and energy of this class of compounds. [ABSTRACT FROM AUTHOR]

Age-related diseases, such as osteoarthritis, Alzheimer’s disease, diabetes, and cardiovascular disease, are often associated with chronic unresolved inflammation. Neutrophils play central roles in this process by releasing tissue-degenerative proteases, such as cathepsin G, as well as pro-inflammatory leukotrienes produced by the 5-lipoxygenase (5-LO) pathway. Boswellic acids (BAs) are pentacyclic triterpene acids contained in the gum resin of the anti-inflammatory remedy frankincense that target cathepsin G and 5-LO in neutrophils, and might thus represent suitable leads for intervention with age-associated diseases that have a chronic inflammatory component. Here, we investigated whether, in addition to BAs, other triterpene acids from frankincense interfere with 5-LO and cathepsin G. We provide a comprehensive analysis of 17 natural tetra- or pentacyclic triterpene acids for suppression of 5-LO product synthesis in human neutrophils. These triterpene acids were also investigated for their direct interference with 5-LO and cathepsin G in cell-free assays. Furthermore, our studies were expanded to 10 semi-synthetic BA derivatives. Our data reveal that besides BAs, several tetra- and pentacyclic triterpene acids are effective or even superior inhibitors of 5-LO product formation in human neutrophils, and in parallel, inhibit cathepsin G. Their beneficial target profile may qualify triterpene acids as anti-inflammatory natural products and pharmacological leads for intervention with diseases related to aging.

A new taraxerene-type hexacyclic triterpene acid named (12R,13S)-3-methoxy-12,13-cyclo-taraxerene-2,14-diene-1-one-28-oic acid ( 1) , together with a known compound 3,7-dihydroxy-5-octanolide ( 2 ), was isolated from the roots of Euscaphis japonica . The structure of new compound 1 was elucidated on the basis of NMR, HR-ESIMS and X-ray diffraction analysis. It showed promising inhibitory activity on oleic acid induced triglyceride accumulation on HepG2 cells. [ABSTRACT FROM AUTHOR]

Recent studies have found that triterpene acid type compounds has many effects including antiinflammatory, regulating blood sugar level, antiviral and antitumor activity. More importantly, triterpene acid type compounds has become one of the most popular topics recently because its selective toxic effects on cancer cells and harmless to normal cells at the same time. This review summarized the antitumor activity and the mechanism of triterpene acid type compounds, providing guideline for further research and development of new antitumor natural products. [ABSTRACT FROM AUTHOR]

Mesona procumbens Hemsley is a plant conventionally processed to provide popular food materials and herbal medicines in Asia. In this study, six triterpene acids, including five new ones (mesonaic acids D-H, 1 - 5 ), and one proximadiol-type sesquiterpene ( 7 ) were isolated from the methanolic extract of the air-dried M. procumbens . Chemical structures of 1 ‒ 7 were established by spectroscopic methods, especially 2D NMR techniques ( 1 H- 1 H COSY, HSQC, HMBC, and NOESY) and HRESIMS. Concerning their biological activities, compounds 1 , 2 , 6 , and 7 were examined manifesting high inhibition toward the pro-inflammatory NO production with EC 50 values ranging from 12.88 to 21.21 µM, outrunning the positive control quercetin (24.12 µM). The mesoeudesmol B ( 7 ) identified from M. procumbens is the very first example, which exhibited high anti-inflammatory activity diminishing the level of the lipopolysaccharide-induced NO in RAW264.7 macrophage cells, thereby suppressing the secretion of pro-inflammatory cytokines TNF-α and IL-6 and the level of two critical downstream inflammatory mediators iNOS and COX-2., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2022 Huang, Lo, Liao, Lin, Shen, Huang, Li, Lee, Kuo and Liaw.)

[Objective] To understand the morphological characteristics and germination rate of Fritillaria cirrhosa D. Don seeds and provide the basis for seed quality standard. [Method] The purity, 1 000-grain weight, water content, water absorption rale and germination rate of Fritiliaria cirrhosa D. Don seed were determined, to establish quality classification standard of Fritillaria cirrlutsa D. Don seed. [Results] The purity was 92.48%. and the germination power was 60.45%. and ihe germination rate was 94. 80%. and the water content was 13. 81%. and the maximum water absorption rate was 160. 18%. and the life force was 90.40%. and the 1 000-grain weight was 1.724 g. disease was 3.748 0%. dead insects and eggs was 0.030 8%. [Conclusion] The quality classification standard of Fritillaria cirrhosa D. Don seed was established to the basis for the artificial cultivation of Fritillaria cirrhosa D. Don. [ABSTRACT FROM AUTHOR]

Abstract: For seeking the good natural material to develop new agent to treat diabetes, the total triterpene acid (TTA) fraction extracted from Folium Eriobotryae [leaves of Eriobotrya japonica (Thunb.) Lindl.] was evaluated for its hypoglycemic and hypolipidemic potential through normal, alloxan and streptozotocin-induced diabetic mice administered with graded oral doses (100, 200, 300mg/(kgday)) for 7 or 14 days. The results showed that a dose of 300mg/kg of TTA is the most effective dose to cause significant (p <0.01) hypoglycemic and/or hypolipidemic effects on normal, alloxan and streptozotocin-induced diabetic mice. This dose also significantly (p <0.01) lowered the glycosylated serum protein (GSP), total cholesterol (TC) and triglyceride (TG) level in severely diabetic mice. Furthermore, TTA increased the superoxide dismutase activity (SOD) and the serum insulin level of diabetic mice. These evidences indicated that the total triperpene acid fraction from Folium Eriobotryae has a high anti-diabetic potential along with a good hypolipidemic profile. [Copyright &y& Elsevier]

Abstract: Boswellic acids are the main well-known active components of the resin of Boswellia carteri (Burseraceae) and these are still dealing with the ethnomedicinal use for the treatment of rheumatoid arthritis and other inflammatory diseases. Although several studies have already been reported on the pharmacological properties, especially on the anti-inflammatory activity, of Boswellia carteri resin and boswellic acids, the ethnomedicinal importance of Boswellia carteri and its components, boswellic acids, prompted us to undertake detailed investigation on the constituents of the resin and their anti-inflammatory activity. Fifteen triterpene acids, viz., seven of the β-boswellic acids (ursane-type) (1–7), two of the α-boswellic acids (oleanane-type) (8, 9), two of the lupeolic acids (lupane-type) (10, 11), and four of the tirucallane-type (12–14, 16), along with two cembrane-type diterpenes (17, 18), were isolated and identified from the methanol extract of the resin of Boswellia carteri. Upon evaluation of 17 compounds, 1–14 and 16–18, and compound 15, semi-synthesized from 14 by acetylation, for their inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1μg/ear) in mice, all of the compounds, except for 18, exhibited marked anti-inflammatory activity with a 50% inhibitory dose (ID50) of 0.05–0.49mg/ear. [Copyright &y& Elsevier]

Reports on the isolation and identification of nine triterpene carboxylic acids from the ethanol (EtOH) extracts of red and green perilla leaves. Inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammations in mice, and on the Epstein-Barr virus early antigen activation by TPA.

The triterpene acid isolated from Polyporus ailanthus (Aphyllophorales) is identified as eburicoic acid on the basis of1H and13C NMR, electron-impact mass, and IR spectra. [ABSTRACT FROM AUTHOR]

A chemical study on the epidermis of cultivated edible mushroom Wolfiporia cocos resulted in the isolation and identification of 46 lanostane triterpenoids, containing 17 new compounds ( 1 - 17 ). An experimental determination of their anti-inflammatory activity showed that poricoic acid GM ( 39 ) most strongly inhibited NO production in LPS-induced RAW264.7 murine macrophages with an IC 50 value at 9.73 μM. Furthermore, poricoic acid GM induced HO-1 protein expression and inhibited iNOS and COX2 protein expression as well as the release of PGE 2 , IL-1β, IL-6, TNF-α, and reactive oxygen species (ROS) in LPS-induced RAW264.7 cells. Mechanistically, poricoic acid GM suppressed the phosphorylation of the IκBα protein, which prevented NF-κB from entering the nucleus to lose transcriptional activity and inhibited the dissociation of Keap1 from Nrf2, thereby activating Nrf2 into the nucleus to regulate antioxidant genes. Furthermore, the MAPK signaling pathway may play a significant role in poricoic acid GM-induced elimination of inflammation. This work further confirms that lanostane triterpenoids are key ingredients responsible for the anti-inflammatory properties of the edible medicinal mushroom W. cocos .

We investigated the effects of triterpene acids (TAs), ursolic acid (UA) and oleanolic acid (OA), on the induction of proliferation and differentiation of normal rat mammary epithelial cells (RMEC) or organoids cultured in Matrigel or primary culture system. To elucidate the effects, we tested their differentiation inducing activities with intercellular communication ability, cell cycle patterns, induction of apoptosis, and morphological differentiation in the three dimensional extracellular culture system. To study the changes of RMEC subpopulation in culture, the cultured cells were isolated, immunostained with peanut lectin (PNA) and anti-Thy-1.1 antibody and then analyzed with flow cytometry. Four different subpopulations, such as PNA and Thy-1.1 negative cells (B-), PNA positive cells (PNA+), Thy-1.1 positive cells (Thy-1.1+), PNA and Thy-1.1 positive cells (B+), were obtained and the size of each subpopulation was changed in culture with time in the presence of TAs. Intercellular communication was observed in culture for 7 days in TAs-treated cells, but not in culture for 4 days with scrape-loading dye transfer technique. G2/M phase cells and the number of apoptotic population were increased in TAs-treated groups in cell cycle analyses. S phase fractions were reduced and the change of G1 phase cells was not observed. The colonies with distinct multicellular structures, such as stellate, ductal, webbed, squamous, lobulo-ductal colonies, were observed in Matrigel culture and the frequencies of each colony were changed in the presence of TAs. These results suggest that UA and OA have differentiation inducing effects on rat mammary epithelial cells in primary or in Matrigel culture. [ABSTRACT FROM AUTHOR]

Three triterpene acids, ursolic acid ( 1), corosolic acid ( 2), and oleanolic acid ( 7), were isolated from the ethanol extract of leaves of Perilla frutescens (L.) Britton var. japonica Hara (Labiatae; Japanese name: Egoma). These acids are the active principles responsible for the cytotoxicity against three cultured human tumor cell lines, HL-60 (leukemia carcinoma), MCF-7 (breast carcinoma), and Hep-G2 (hepatic carcinoma), with half maximal inhibitory concentration (IC50) values of 12–48 μ M. [ABSTRACT FROM AUTHOR]

Mistletoe (Viscum album L.) from Santalaceae family is a hemiparasitic plant containing triterpene acids which widely was used as complementary remedy in cancer therapy for decades. Mistletoe is growing on various tree species as well as some endemic and native species of Hyrcanian forests of Iran such as Parrotia persica (Persian ironwood) and Carpinus betulus (Hornbeam). The aim of this work was to compare the amount of triterpene acids including oleanolic acid (OA), betulinic acid (BA) and ursolic acid (UA) in foliage (leaves and stems) and fruit of mistletoes settled on P. persica and C. betulus as hosts in autumn. In this study, mistletoe plant parts were collected from three bases of each host species in Daeiz forest of Hyrcanian forests of Iran. The samples were extracted with ethyl acetate and analyzed by HPLC. The results indicated that the host species had no significant effect on the amount of triterpene acids in the mistletoes. But the organ type (foliage and fruit), had significant effect on the BA content meanwhile it didn't show any significant effect on the OA. The highest level of BA was significantly detected in foliage of mistletoes on P. persica and C. betulus (1.23 and 0.97 mg/g dry weight) respectively. Independence of statistical analysis, the highest content of OA (8.52 mg/g dry weight) was observed in the foliage of V. album on P. persica. On the other hand, BA was not detected in mistletoe fruits on both host species. UA was not detected in any samples. • The highest amount of betulinic acid with significant difference was found in the foliage of Viscum album. • The highest amount of oleanolic acid was detected in the foliage of Viscum album on Parrotia persica and Carpinus betulus. • Oleanolic acid was the dominant triterpene acid in the foliage and fruit of this plant on both studied host species. [ABSTRACT FROM AUTHOR]

In the current investigation, new monomers of myrrhanone B and lupeolic acid were prepared via reaction of triterpenic acids with linkers in the presence of K 2 CO 3 . In addition, new bis-myrrhanone B homodimers, myrrhanone B-myrrhanol B heterodimers, and bis-myrrhanone β-boswellic acids heterodimer were prepared. Evaluation of these compounds on the proliferation of four different human cancer cell lines, viz., FaDu (pharynx carcinoma), A2780 (ovarian carcinoma), HT29 (colon adenocarcinoma) and A375 (malignant melanoma) has been performed. It is worth mentioning that compounds 4, 7, 8, 10, and 11 possess potent antiproliferative effect towards HT29 cancer cells with IC 50 values of 8.1 μM, 5.4 μM, 8.8 μM, 6.8 μM, and 8.2 μM, respectively. In addition, these compounds display good to moderate antiproliferative activities towards A2780 and A375 with IC 50 values ranging from 10.4 to 24.2 μM. Moreover, the molecular docking studies of most active compounds (4, 7, 8, 10 and 11) with six anti-cancer drug targets DHFR, VEGFR2, HER-2/neu, CDK6, hCA-IX and LOX also carried, in order to know the mode of binding interaction and energy of this class of compounds., (Copyright © 2017 Elsevier Masson SAS. All rights reserved.)

In the context of ethno botanical importance with no phytochemical investigations, Mussaenda roxburghii have been investigated to explore it's phytoconstituents and studies of their antibiofilm activity. Four compounds have been isolated from the aerial parts of this plant and were characterized as 2α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid (1), β-sitosterol glucoside (4), lupeol palmitate (5), and myoinositol (6). All these compounds were tested for antibacterial and antibiofilm activity against Pseudomonas aeruginosa. Compound 1 exhibited three times more antibiofilm activity with minimum inhibitory concentration (MIC) at 0.74 mm compared to that of streptomycin. Molecular docking studies exhibited a very high binding affinity of 1 with P. aeruginosa quorum sensing proteins and motility associated proteins viz. LasR and PilB, PilY1, PilT, respectively. Compound 1 was also found to be non-cytotoxic against sheep RBC and murine peritoneal macrophages at selected sub-MIC doses., (© 2017 Wiley-VHCA AG, Zurich, Switzerland.)