Hemolytic and cytotoxic activity of dammarane-type triterpenoids

The relationship between chemical structure and hemolytic and cytotoxic activity was studied for dammarane-type triterpenoids isolated from leaves of various Betula species. It was shown that an acyclic sidechain (betulafolienetriol and betulafolienetetraol) imparted significantly higher hemolytic and cytotoxic activity than a cyclic sidechain. The activity of epoxydammaranetriol with an 11α-OH group was slightly higher than that of epoxydammaranetriol with a 12β-OH group. The activity of C-3 epimeric epoxydammaranetriols and-tetraols with a 12β-OH group was independent of the configuration of the C-3 hydroxyl. Epoxydammaranetriols with an 11α-OH group and epoxydammaranediols with a 3α-OH group were more active than those with a 3β-OH group. The effect of the most active compounds on the microviscosity of tumor-cell membranes was determined. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 61–63, January–February, 2007.     

D:C-friedooleanane-type triterpenoids from Lagenaria siceraria and their cytotoxic activity

Four new D:C-friedooleanane-type triterpenes, 3 beta-O-(E)-feruloyl-D:C-friedooleana-7,9(11)-dien-29-ol (1), 3 beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-ol (2), 3 beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (3), and methyl 2 beta,3 beta-dihydroxy-D:C-friedoolean-8-en-29-oate (6), together with five known triterpenes with the same skeleton, 3-epikarounidiol (4), 3-oxo-D:C-friedoolena-7,9(11)-dien-29-oic acid (5), bryonolol (7), bryononic acid (8), and 20-epibryonolic acid (9), were isolated from the methanol extract of the stems of Lagenaria siceraria. The structures of those compounds were elucidated using spectroscopic methods. Compounds 3 and 9 showed significant cytotoxic activity against the SK-Hep 1 cell line with IC50 values of 4.8 and 2.1 microg/ml, respectively. Based on these initially promising results, the two D:C-friedooleanane triterpenes merit further study as potential anticancer agents.     

Two new polyhydroxylated triterpenoids from Salvia urmiensis and their cytotoxic activity

Two new polyhydroxylated triterpenoids were isolated from the acetone extract of the aerial parts of Salvia urmiensis Bunge. Their structures were elucidated by 1D and 2D NMR and HR-ESI-MS analyses as olean-12-ene-1β,3β,11α,22α-tetraol (1) and urs-12-ene-1β,3β,11β,22α-tetraol (2). The effect of these compounds on cell viability of MCF-7 cells was investigated by the MTT assay. Compounds 1 and 2 showed weak cytotoxicity with IC₅₀ values of 110.23 ± 0.12 and 88.35 ± 0.09 μM, respectively.     

Lupane triterpenoids,antioxidant potential and antimicrobial activity of Myrciaria floribunda (H. West ex Willd.) O. Berg.

Chemical composition of the methanol extract of Myrciaria floribunda leaves was investigated. The nor-lupane triterpenoids platanic acid and messagenic I acid were identified, along with other known triterpenoids (betulinic aldehyde, ursolic acid acetate and betulinic acid), a new lupane triterpenoid (2α,6α,30-trihydroxybetulinic acid) and the flavonoids catechin, quercetrin and mirycitrin. The structures were determined by spectroscopic methods (NMR, LC-MS, GC-MS). The major isolated compound was betulinic acid. The methanol extract and 2α,6α,30-trihydroxybetulinic acid were evaluated for their DPPH scavenging potential. The tested triterpenoid was one hundred times more active than betulinic acid, but less active than the extract. Screening for antimicrobial activity showed that the methanol extract was active against Staphylococcus aureus and Escherichia coli, but inactive against Candida albicans and Candida krusei, while 2α,6α,30-trihydroxybetulinic acid was inactive to all tested microorganisms.     

Daphniphyllum alkaloids with cytotoxic activity from Daphniphyllum angustifolium

A new Daphniphyllum alkaloid, daphnezomine W (1), together with four known ones, were isolated from the stems of Daphniphyllum angustifolium Hutch. Their structures were elucidated by spectroscopic methods and comparing with the literature data. Compound 1 was a new daphnezomine L-type alkaloid and exhibited moderate cytotoxic activity against Hela cell line with IC₅₀ of 16.0 μg/mL. A plausible biosynthetic pathway of 1 was also proposed.     

Antitrypanosomal activity of Brazilian propolis from Apis mellifera

Extracts from different samples of Brazilian propolis were obtained by Soxhlet extraction or maceration at room temperature using ethanol, water, and accombination of both solvents. Analysis of their composition using HPLC revealed that no major differences were seen when a propolis sample was subject to different extraction methods. The activity of the 15 extracts was assayed against bloodstream trypomastigotes of Trypanosoma cruzi, the etiologic agent of Chagas' disease. Multivariate analysis was applied to evaluate the efficiency of the different extracts and the trypanocidal activity. The extracts could be divided into two groups. In the first, in which, extracts were obtained by reflux in Soxhlet using 100% ethanol, there was a lower content of bioactive compounds and consequently lower trypanocidal activity. Extract 136-Et100 stands out in this group, since it had the highest levels of bioactive compounds together with highest activity against the parasite when compared with all other extracts. The second group comprises extracts with intermediate levels of bioactive compounds and higher activity against T. cruzi.     

New nor-oleanane triterpenoids from the fruits of Stauntonia brachyanthera with potential anti-inflammation activity

Abstract

The continuing studies on the fruits of Stauntonia brachyanthera led to the isolations of 6 normal and nor-oleanane triterpenoids, including two new compounds, brachyantheoraside B10 (1) and brachyantheraside C1 (2). Compounds 1–3 showed inhibitory activity on lipopolysaccharide (LPS)-induced nitric oxide production in RAW 264.7 macrophages with the IC₅₀ values of 27.04, 26.22, and 21.41?μM, respectively, which were all stronger than that of indomethacin. The study not only revealed a new type of nor-oleanane triterpenoids, but also confirmed the anti-inflammation abilities of three type nor-oleanane triterpenoids as the inhibitors of NO production.     

Lupane glycosides from the leaves of Acanthopanax koreanum

Three new lupane-type saponins, acankoreosides F--H (1--3) were isolated from the methanol extract of the leaves of Acanthopanax koreanum NAKAI. The structures of these three saponins were established by chemical and spectroscopic analysis as 3alpha,30-dihydroxylup-20(29)-en-23,28-dioic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (1), 3alpha,30-dihydroxylup-23-al-20(29)-en-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (2), and (20S) 3alpha-hydroxylup-23-al-28,29-dioic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (3), respectively. The effects of the isolates (1-3) on the lipopolysaccharide-induced production of nitric oxide and prostaglandin E2 were evaluated in RAW 264.7 macrophages.     

New Acylated Oleanane and Lupane Triterpenes from Gymnema sylvestre

Phytochemical investigation of the aerial parts of Gymnema sylvestre led to the isolation of two known oleanane‐type triterpenes, 1 and 3 , five new acylated derivatives, 2, 4 , and 5 – 7 , and a new lupane‐type triterpene, 8 . The structures and relative configurations of these compounds were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR spectroscopy and mass spectrometry, and by the comparison of their NMR data with those of related compounds.     

Three lanostane triterpenoids with antitrypanosomal activity from the fruiting body of Hexagonia tenuis

During the search for new antitrypanosomal drug leads, three new antitrypanosomal compounds, hexatenuins A–C (1–3), were isolated from the fruiting body of Hexagonia tenuis. 1 and 3 possessed an unusual malonate half-ester functional group at C-3 position, and 1 and 2 had a spirostructure in the side-chain. Their structures were elucidated using MS analyses, extensive 2D-heteronuclear NMR data interpretation. Compounds 1–3 showed in vitro antitrypanosomal activity against Trypanosoma brucei brucei with IC₅₀ values of 0.57, 8.60 and 5.62 μg/ml, respectively.     

A New Lupane from the Resin of Boswellia carterii

A new lupan-type triterpene was isolated from the resin of Boswellia carterii Birdw. Based on the spectral methods, its structure was elucidated as lup-20(29)-ene-3α-acetoxy-24-oic acid.     

Synthesis of azolylalkylquinolines with cytotoxic activity

The syntheses of various azolylalkylquinoline derivatives in which the nature of the linkage between the quinoline and azolylalkyl moieties of the molecule were altered are described. The compounds were tested for cytotoxic activity towards cancer cells and compound 27 was found to exhibit moderate in vivo activity in a murine sarcoma model.     

泽泻三萜类成分的提取工艺优化及活性评价

建立泽泻中三萜类成分的最佳提取工艺,并考察其对老年性耳聋小鼠血清生理学指标的影响.通过正交试验优化泽泻三萜类成分的提取工艺,并用紫外分光光度法(UV)测定含量.采用D-半乳糖建立小鼠老年性耳聋模型,灌胃给予泽泻三萜类成分提取物后,测定小鼠血清丙二醛(MDA)含量和超氧化物歧化酶(SOD)活力.结果表明:泽泻三萜类成分的...     

A new furostanol saponin from Dendrobium chrysanthum Lindl. with cytotoxic activity

A new furostanol saponin, (25R)-26-O-(α-d-glucopyranosyl)-(1→2)-α-l-rhamnopyranosyl-furost-5-ene-3β, 22α, 26-triol-3-O-α-d-glucopyranoside (1), together with four known compounds 2–5 were isolated from the ethanolic extract of the stems of Dendrobium chrysanthum Lindl. The structures of these new compounds were identified by extensive spectroscopic analysis including 1D and 2D NMR and HR-ESI-MS, as well as chemical methods. Compounds 1–3 were isolated from D. chrysanthum for the first time. Furthermore, the inhibitory effects of the compounds on tumor cells were evaluated, and compounds 1–2 exhibited significant cytotoxic activities potentially against SPC-A1, MCF-7 and HeLa human cancer cell lines. Compounds 3–5 showed inhibitory activity against the SPC-A1 and MCF-7.     

Lanostane-type triterpenoids from Diospyros discolor

Four new lanostane-type triterpenes, 24-ethyl-3beta-methoxylanost-9(11)-en-25-ol (1), 3beta-methoxy-24-methylenelanost-9(11)-en-25-ol (2), 3beta-methoxy-25-methyl-24-methylenelanost-9(11)-en-21-ol (3) and 3beta-methoxy-24-methyllanosta-9(11),25-dien-24-ol (4) together with three known triterpenes, betulinaldehyde, betulinic acid methyl ester, and ursaldehyde have been isolated from the methanol extract of the twigs of Diospyros discolor. The structures of those new compounds were elucidated by spectroscopic methods.     

New triterpenoids from Tricholoma saponaceum

Six new triterpenes, saponaceolides E (1), F (2), and G (3), and saponaceoic acids I (4), II (5), and III (6) were isolated from the fruiting body of the fungus Tricholoma saponaceum, and their structures were elucidated on the base of extensive NMR experiments. Compounds 1 and 2 exhibited inhibitor activity against B16 and L929 cells.     

New triterpenoids from Gentiana lutea

Three new triterpenoids, 2,3-seco-3-oxours-12-en-2-oic acid, 2,3-seco-3-oxoolean-12-en-2-oic acid, and betulin 3-O-palmitate, have been isolated from the rhizomes and roots of Gentiana lutea, together with five known ones. The structures of the new compounds were determined by spectral and chemical methods.     

New triterpenoids from Corchorus trilocularis

Two new tetracyclic triterpenoid trilocularol A and trilocularol A 3-glucoside and one pentacyclic triterpenoid tirlocularoside A were isolated from Corchorus trilocularis L., their structure were elucidated as 3beta,6alpha,16alpha,20(S),27-pentahydroxydammar-24(Z)-ene (1), 3beta-D-glucopyranosyloxy-6alpha,16alpha,20(S),27-tetrahydroxydammar-24(Z)-ene (2) and 2alpha,3beta,19alpha,30-tetrahydroxyurs-12-en-24,28-dioic acid 28-O-beta-D-glucopyranosyl ester (3). respectively, on the basis of detailed spectroscopic studies.