Structure of ulososide A,a new triterpenoid glycoside from theUlosa sp. sponge

A new triterpenoid glycoside, (20S,22S,23R,24S)-3,22,23-trihydroxy-3-O-[O-(-D-glucuronopyranosyl)-(16)-(-D-glucopyranosyl)]-14-nor-24-methyllanost-8(9)-en-31-oic acid (ulososide A), has been isolated from the sponge Ulosa sp. and characterized.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1326–1329, July, 1994.     

A new triterpenoid compound from stems and leaves of American ginseng

A new dammarane-type triterpenoid compound was isolated from stems and leaves of American ginseng. The structure of the new sapogenin was elucidated by the combined analysis of NMR and HR-ESI-MS as dammar-20S, 25S-epoxy-3β, 12β, 26-triol (1). Compound 1 showed cytotoxic effect on human SM7721 and human Hela cells in vitro.     

A new dihydrochalcone glycoside from the stems of Homalium stenophyllum

A new dihydrochalcone glycoside, phloretin-4-O-β-D-glucopyranoside (1), together with seven known flavonoids (2–8), were isolated from the stems of Homalium stenophyllum. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with data reported in the literature. The known compounds (2–8) were isolated from the genus Homalium for the first time. All compounds were evaluated for their antibacterial activities against six pathogenic bacteria in vitro.     

Two new triterpenoid glycosides from the stems of Camellia oleifera Abel

Two new oleanane-type triterpenoid glycosides, 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)-[β-D-glucuronopyranosyl-(1→2)]-β-D-glucuronopyranosyl-22α-angeloyloxyolean-12-ene-15α,16α,28-triol(1) and 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)-[β-D-glucuronopyranosyl-(1→2)]-β-D-glucuronopyranosyl-21β-acetyl-22α-angeloyloxyolean-12-ene-16α,28-diol (2) were isolated from the stems of Camellia oleifera Abel. Their structures were elucidated by means of spectroscopic methods and chemical evidence. The cytotoxic activities of compounds 1–2 were evaluated against five human tumour cell lines (HCT-8, BGC-823, A5049, and A2780). Compounds 1–2 showed cytotoxic activity against five human cancer cell lines, with IC₅₀ values ranging from 3.15 to 7.32 μM.     

A immunosuppressive triterpenoid saponin from the stems of Epigynum griffithianum

Abstract

Chemical investigation of the stems of Epigunum griffithianum led to the isolation and identification of a new triterpenoid saponin (1) and two known compounds (epigynosides A (2) and B (3)). These structures were elucidated by means of spectroscopic analysis (1D and 2D NMR, MS, UV, IR) as well as comparison with the reported data. Compound 1 was evaluated in vitro for the immunosuppressive activities on proliferation of mice splenocyte and displayed significant immunosuppressive activities compared to the positive control (dexamethasone) with the concentration at 25?μM.     

Leptocarposide: a new triterpenoid glycoside from Ludwigia leptocarpa (Onagraceae)

A new triterpenoid bidesmoside (leptocarposide) possessing an acyl group in their glycosidic moiety (1), together with the known luteolin‐8‐C‐glucoside (2) and 1‐O‐β‐d ‐glucopyranosyl‐(2S,3R,8E)‐2‐[(2′R)‐2‐hydroxypalmitoylamino]‐8‐octadecen‐1,3‐diol (3) was isolated from the n‐butanol‐soluble fraction of whole plant of Ludwigia leptocarpa (Nutt) Hara (Onagraceae). Structure of compound 1 has been assigned on the basis of spectroscopic data (¹H and ¹³C NMR, ¹H‐¹H COSY, HSQC, HMBC, and ROESY), mass spectrometry, and by comparison with the literature. This compound was further screened for its potential antioxidant properties by using the radical scavenging assay model 2,2‐diphenyl‐1‐picrylhydrazyl and reveals non‐potent antioxidant activities, while compound 2 shows SC₅₀ of 0,038 mM. Copyright © 2013 John Wiley & Sons, Ltd.     

One new 19-nor cucurbitane-type triterpenoid from the stems of Momordica charantia

One new 19-nor cucurbitane-type triterpenoid (3β,9β,25-trihydroxy-7β-methoxy-19-nor-cucurbita-5,23(E)-diene) (1), together with other six known cucurbitane-type triterpenoids (2–7), were isolated from the stems of Momordica charantia L. The chemical structure of 1 was elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, COSY and ROESY), MS experiments. Using MTT assay, compound 1 exhibited weak cytotoxicity against HL-60, A-549, and SK-BR-3 cell lines with the IC₅₀ values at 27.3, 32.7 and 26.6 μM, respectively.     

A new cycloartane triterpenoid from the leaves and stems of Fritillaria hupehensis

A new triterpenoid has been isolated from the leaves and stems of Fritillaria hupehensis Hsiao et K.C.Hsia.Its structure wasestablished as(23Z)-9,19-cycloart-23-ene-3α,25-diol 1 through chemical and spectroscopic studies including 2D NMR.Anotherknown triterpenoid 9,19-cycloart-25-ene-3β,24ξ-diol 2 was also isolated.     

A new friedelane triterpenoid and saponin with moderate antimicrobial activity from the stems of Drypetes laciniata

A new friedelane-type triterpene named 3β-hydroxyfriedelane-7,12,22-trione,as well as nine known compounds were isolated from the whole stems of Drypetes laciniata Hutch.(Euphorbiaceae).Their structures were established on the basis of spectroscopic methods.The new triterpene derivative and a known saponin were tested for antimicrobial and antifungal activities and they appeared to be moderate active.     

A new phenolic glycoside from the Idesia polycarpa Maxim. leaves

Phytochemical investigation on the ethyl acetate extract of Idesia polycarpa Maxim. Leaves led to the isolation of four phenolic glycoside isomers (1–4). Compound 2 appeared to be new reported phenolic glycoside, while compound 1 was the first time isolated from the titled species. Their structures were established by IR, UV, HRESI-MS and 1D and 2D NMR spectroscopies analysis and comparison of spectral data with previously reported data. The compounds 3 and 4 showed stronger activity of scavenging the DPPH free radical than the other two compounds, while the compounds 1 and 2 showed a significant activity of scavenging the ABTS free radical. Compounds 2 and 4 exhibited stronger cytotoxicity against HepG2 cell lines compared to compounds 1 and 3. Moreover, compound 3 presented the highest cytotoxicity against MCF cell lines with IC₅₀ value of 37.17?±?0.26?μg/mL than compounds 1, 2 and 4.     

日本续断中新的双糖链三萜皂苷的结构研究

从日本续断根部的乙醇提取物中分得一个新的三萜皂苷。经过测定,它为：3-O-α-L-吡喃鼠李糖(1→3)-β-D-吡喃葡萄糖(1→3)-α-L-吡喃鼠李糖(1→2)-α-L-吡喃阿拉伯糖9常春藤苷元－28-O-β-吡喃葡萄糖酯苷)。结果表明,采用一维SEMDY,旋转坐标NOE差谱和选择性远程DEPT核磁共振新技术相结合的方法测定糖链结构不需要对化合物进行化学降解或衍生化,方法简便、快速,测定结果可靠,每个糖基的信号可以分辨和明确归属。     

New triterpenoid saponins from the leaves of Cyclocarya paliurus

Two new secodammarane triterpenoid saponins, cyclocariosides I and J (1 and 2), and a new epoxydammarane triterpenoid saponin, cyclocarioside K (3) were isolated from the ethanol extracts of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic techniques.     

A new triterpenoid saponin from the leaves and stems of Panax quinquefolium L.

One new triterpenoid saponin,quinquenoside L_(17)(1),was isolated from the leaves and stems of Panax quinquefolium L.,and its structure was elucidated as 20-O-[(β-D-xylopyranosyl-(1-6)-O-β-D-glucopyranosyl)]-6-O-β-D-glucopyranosyl-dammar-24-ene- 3,6,12,20-tetraol,by the combination analysis of one-dimensional NMR and two-dimensional NMR,mass spectrometry,CD spectrum and chemical evidences.     

A new benzophenone glycoside from the leaves of Psidium guajava L.

A new benzophenone glycoside,2,6-dihydroxy-4-O-β-D-glucopyranosylbenzophenone(1),was isolated from the leaves of guajava L.Its structure was elucidated by spectral and chemical methods.1 showed significant activities to secretion of NO in mouse peritoneal macrophages in 10μmol/L.     

A new aromatic glycoside and its anti-proliferative activities from the leaves of Bergenia purpurascens

Chemical investigation of the ethanolic extracts of the dried leaves of Bergenia purpurascens led to the isolation and identification of a new aromatic glycoside, 1-O-β-D-glucopyranosyl-2-methoxy-3-hydroxyl-phenylethene (1), along with other 19 known compounds (2–20). The structure of compound 1 was determined by a detailed analysis using various analytical techniques, including 1D and 2D NMR. In vitro anti-proliferative activities of compound 1 on five human cancer cell lines were evaluated. The results showed that compound 1 possessed the most potent effects with the IC₅₀ values of 14.36 ± 1.04 μM against T24 cells. The further bioactivity analysis showed that compound 1 induced apoptosis of T24 cells, and altered anti- and pro-apoptotic proteins, leading to mitochondrial dysfunction and activation of caspase-3 for causing cell apoptosis. The present investigation illustrated compound 1 might be used as a potential antitumour chemotherapy candidate.     

A new antibacterial benzophenone glycoside from Psidium guajava (Linn.) leaves

Bioactivity-guided fractionation of methanol extract from the leaves of Psidium guajava L. (Myrtaceae) yielded a new benzophenone glycoside, Guajaphenone A (2) together with two known compounds, Garcimangosone D (1) and Guaijaverin (3). Their structures were elucidated by analysis of spectroscopic data including 1D and 2D NMR and electrospray ionisation mass spectrometry (ESI-MS). The isolated compounds were screened against standard strains of Gram-positive and Gram-negative bacteria using broth dilution assay method, and the MIC values determined and compared with reference antibiotic ceftriaxone. They were found to have significant antibacterial activities against Escherichia coli and Staphylococcus aureus with all of them showing better activities against S. aureus, but displaying weaker activities, in comparison to ceftriaxone. However, despite reduced effect of these compounds against the organisms, this work opens the perspective to use these molecules as ‘leads’ for the design of novel and selective drug candidates for some tropical infectious diseases.     

A new triterpenoid glucoside from Leucas zeylanica

Abstract

A new triterpenoid glucoside, leuctriterpencoside (1), along with two known compounds (2–3) were isolated from Leucas zeylanica. The structure of the new compound was elucidated using comprehensive spectroscopic methods. Compound 1 showed significant inhibitory activity against α-glucosidase (IC₅₀ value of 0.85?±?0.12?μM).     

A new cucurbitane triterpenoid from Momordica charantia

One new cucurbitane-type triterpenoid saponin, 5b,19-epoxycucurbita-6,23-diene-3b,19,25-triol-3-O-b-D-allopyranoside (1), named momordicoside P was isolated from the fresh fruits of Momordica charantia. The structure of the saponin was elucidated byspectral methods, including 2D-NMR spectra.     

A new cytotoxic diterpenoid glycoside from the leaves of Blumea lacera and its effects on apoptosis and cell cycle

A new diterpenoid glycoside, 6E,10E,14Z-(3S)-17-hydroxygeranyllinalool-17-O-β-d-glucopyranosyl-(1?→?2)-[α-l-rhamnopyranosyl-(1?→?6)]-β-d-glucopyranoside (1) together with the known diterpenoid glycoside (2) and two known flavonoid glycosides (3, 4) were isolated from the methanol extract of Blumea lacera leaves. The structures were determined by the interpretation of their spectroscopic data and comparison with the literature. All compounds were isolated for the first time from B. lacera and evaluated for their cytotoxic activity. Only the new compound (1) showed strong cytotoxic activity with the lowest IC₅₀ value (8.3 μM) being displayed against MCF-7 breast cancer cells. In apoptosis and cell cycle analysis, 1 revealed strong apoptotic activity against MCF-7 cells (45.5% AV⁺/PI^?) after 24 h, but showed no arresting of any of the cell cycle phases in MCF-7.