New antimicrobial pregnane glycosides from the stem of Ecdysanthera rosea

Phytochemical investigation on the stem of Ecdysanthera rosea led to the isolation of eight new C-21 pregnane glycoside ecdysosides A–H (1–8), together with one known pregnane glycoside ecdysantheroside A (9). Their structures were elucidated based on extensive spectroscopic data (MS, IR, 1D and 2D NMR) analysis, as well as comparison with the reported literature data. Antimicrobial activities of all the compounds were evaluated against bacteria and yeasts. Compounds 1, 9, 3 and 5 exhibited moderate antibacterial activities against respective Enterococcus faecalis and Providensia smartii, with MIC value of 12.5 μg/mL. Compound 8 showed significant anti-yeast activity against Cryptococcus neoformans with MIC value of 12.5 μg/mL.     

New hydroquinone diglycoside acyl esters and sesquiterpene and apocarotenoid from Ecdysanthera rosea

Phytochemical studies on the ethanol extract of the aerial parts of Ecdysanthera rosea led to the isolation of three new compounds, hydroquinone diglycoside acyl esters, ecdysanrosin A (1) and sesquiterpene, 5β-hydroperoxycostic acid (2) and apocarotenoid, 2, 4, 7-trimethyl-2, 4, 6, 8-tetraene-dialdehyde (3). Their structures were elucidated on the basis of extensive spectroscopic analysis.     

New furostanol saponins from Smilax aspera L. and their in vitro cytotoxicity

The occurrence of the two new cis-fused A/B rings furostanol saponins (25S)-26-O-β-d-glucopyranosyl-5β-furostan-1β,3β,22α,26-tetraol-1-O-β-d-glucopyranoside and (25S)-26-O-β-d-glucopyranosyl-5β-furostan-1β,2β,3β,5β,22α,26-hexaol and the known compounds (25S)-26-O-β-d-glucopyranosyl-5β-furostan-3β,22α,26-triol-3-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranoside and (25S)-26-O-β-d-glucopyranosyl-5β-furostan-3β,22α,26-triol-3-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranoside, trans-resveratrol, (+) catechin and (−) epicatechin in the rhizomes of Smilax aspera is reported. All saponins have been isolated as their 22-OMe derivatives, which were further subjected to extensive spectroscopic analysis. The isolated furostanol saponins were evaluated for cytotoxic activity against human normal amniotic and human lung carcinoma cell lines using neutral red and MTT assays. In vitro experiments showed significant cytotoxicity in a dose dependent manner with IC₅₀ values in the range of 32.98-94.53 µM.     

Two new cytotoxic triterpenoid saponins from the roots of Clematis argentilucida

Bioassay-guided fractionation of the n-BuOH extract of the roots of Clematis argentilucida led to the isolation of two new triterpenoid saponins along with a known one, cussonside B (3). By extensive spectral analysis and chemical evidences, the structures of the two new saponins were determined to be 3β-O-[β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl] hederagenin-11,13-dien-28-oic acid (1) and 3β-O-{β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl} oleanolic acid (2), respectively. Saponin 1 is the first example of triterpenoid saponins with two double bonds located at C-11 and C-13 in the aglycone from the genus Clematis. The two new saponins exhibited significant cytotoxicity against human leukemia HL-60 cell lines, human hepatocellular carcinoma Hep-G2 cell lines and human glioblastoma U251MG cell lines with a range of IC(50) values from 2.74 to 25.40μM, while 3 showed inactivity against all of the three cancer cell lines.     

Five new furostanol saponins from the rhizomes of Tupistra chinensis

Five new furostanol saponins (1-5), together with three known compounds (6-8) were obtained from the n-butanol soluble fraction of ethanol extract from Tupistra chinensis. Their structures were determined on the basis of chemical methods and spectral data. The isolated compounds were tested in vitro for their cytotoxic activities against the A549, HepG 2 and Caski cancer cell lines. Among them, compounds 6, 7, and 8 showed cytotoxicity against A549 cancer cell lines with IC(50) values of 6.6, 6.7 and 29.1 μM, respectively.     

New triterpenoid saponins from Leontice smirnowii

Three new triterpene saponins, leonticins I (1), J (2) and L (3) were isolated from the tubers of Leontice smirnowii. On the basis of spectroscopic methods, including 2D NMR experiments (DEPT, gs-COSY, gs-HMQC, gs-HMBC and gs-HSQC-TOCSY), mass spectrometry (HR-ESI-MS) and chemical degradation, the structures of the new compounds were elucidated as 3-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-1 → 2)]-α-L-arabinopyranosyl-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (1), 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-galactopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (2) and 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-galactopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)]-[β-D-xylopyranosyl-(1 → 2)]-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (3), respectively. The aglycone 3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid was observed for the first time in Leontice species.     

Antimicrobial activity and cytotoxicity of Trapa bispinosa

The extracts of Trapa bispinosa showed interesting antimicrobial activity against Gram-positive and Gram-negative test organisms and significant cytotoxic activity.     

Two pregnane derivatives and a quinolone alkaloid from Helicteres angustifolia

Phytochemical investigation of the ethanol extract from roots of Helicteres angustifolia led to the isolation of two new pregnane derivatives, heligenin A–B (1–2), and a new quinolone alkaloid, helicterone A (3), along with thirteen known compounds (4–16). The structures of new compounds were established by analysis of extensive spectroscopic data. The absolute configuration of 1 was determined by application of the modified Mosher's method. All of the isolates were evaluated for their anti-proliferative activities against HT-29 human colon cancer cells and OVCA 429 ovarian cancer cells by MTT assay.     

Two new triterpene saponins from the aerial parts of Paraquilegia microphylla

Two new triterpene saponins, paraquinosides A (1) and B (2) were isolated from the aerial parts of Paraquilegia microphylla (Royle) Dromm. et Hutch, a Tibetan ethnic medicine distributed in the Qinghai–Tibet Plateau. On the basis of 1D and 2D NMR evidence, their structure was elucidated as 3-O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl-15-dehydroxyl-16-O-methyl-24, 25-deoxy-26-hydroxylshengmanol-26-O-β-D-glucopyranoside (1) and 3-O-α-L-Rhamnopyranosyl (1→2)-[β-D-glucopyranosyl(1→3)]-β-D-glucopyranosyl-15-dehydroxyl-16-O-methyl-24, 25-deoxy-26-hydroxylshengmanol-26-O-β-D- glucopyranoside (2), respectively.     

New antioxidant and antiglycation active triterpenoid saponins from the root bark of Aralia taibaiensis

Four new oleanane type triterpenoid saponins (1-4) and a known saponin (5) were isolated from the root bark of Aralia taibaiensis Z.Z. Wang et H.C. Zheng. The structures of the four new compounds were elucidated as 3-O-{β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucurono-pyranosyl}-olean-11,13(18)-diene-28-oic acid 28-O-β-d-glucopyranosyl ester (1), 3-O-{β-d-gluco-pyranosyl-(1 → 3)-[α-l-arabinofuranosyl-(1 → 4)]-β-d-glucuronopyranosyl}-olean-11,13(18)-diene-28-oic acid 28-O-β-D-glucopyranosyl ester (2), 3-O-{β-d-glucopyranosyl-(1 → 2)-[α-l-arabinofuranosyl-(1 → 4)]-β-d-glucuronopyranosyl}-oleanolic acid 28-O-β-D-glucopyranosyl ester (3) and 3-O-{β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucuronopyranosyl}-oleanolic acid 28-O-β-d-glucopyranosyl ester (4), on the basis of extensive spectral analysis and chemical evidence. Compounds 1-5 exhibited moderate effects on antioxidant and antiglycation activities, which correlated with treatment of diabetes mellitus.     

Antimicrobial activities and cytotoxicity of the brown alga Cystoseira tamariscifolia

The hexane, ethyl ether and dichloromethane fractions of the brown alga Cystoseira tamariscifolia extract showed interesting antimicrobial activities and cytotoxicity.     

Oleanane-type triterpenoid saponins from Xanthoceras sorbifolia Bunge

Phytochemical analysis of the extract from the seed oil leavings of Xanthoceras sorbifolia Bunge led to the isolation of five new oleanane-type triterpeniod saponins, sorbifoliasides G–K (1–5). Their structures were elucidated on the basis of spectroscopic analysis and chemical derivatization. To our knowledge, compound 5 is the first example of a naturally occurring 3,28-O-bisdesmosic triterpenoid saponin with olefinic linkages at C12 and C15. The cytotoxicity of all compounds against ten selected human cancer cell lines was assayed.     

Constituents and cytotoxicity of Zanthoxylum rhesta stem bark

3,5-Dimethoxy-4-geranyloxycinnamyl alcohol (1), 8-methoxy-N-methylflindersine (2), xanthyletin and sesamin have been isolated from petroleum ether extract of the stem bark of Zanthoxylum rhesta. The petroleum ether extract and 8-methoxy-N-methylflindersine showed cytotoxicity on brine shrimp nauplii.     

New sphingolipids from the root of Isatis indigotica and their cytotoxic activity

Two new sphingolipids were isolated from the 95% EtOH extract of traditional Chinese medicinal plant Isatis indigotica. Their structures were elucidated as (2S,3R)-3-hydroxymethyl-N-(2'-hydroxynonacosanoyl)-trideca-9E-sphingenine(1) and 1-O-beta-D-glucopyranosyl-(2S,3R)-3-hydroxymethyl-N-(2'-hydroxynonacosanoyl)-trideca-9E-sphingenine(2) on the basis of spectroscopic data. Their cytotoxic effects were evaluated by using MTT method.     

Two new nortriterpenoid saponins from Salicornia bigelovii Torr. and their cytotoxic activity

Investigation of characteristic constituents of Salicornia bigelovii Torr. led to isolation of two new 30-nortriterpenoid glycosides, Bigelovii A (1), Bigelovii B (2), together with two known 30-nortriterpenoid glycosides 3-4 and three known oleanane-type triterpenoid glycosides 5-7. The structures of new compounds were elucidated by extensive 1D and 2D NMR, and MS spectroscopic analysis, and chemical evidences. All compounds were isolated for the first time from Chenopodiaceae. Thus compounds 1-4 were evaluated for their cytotoxicity and compouds 1, 3 showed moderate activity against four cell lines, HL-60 (promyelocytic leukemia), MCF-7 (breast carcinoma), HepG2 (liver carcinoma) and A549 (lung carcinoma), with IC(50) values of 6.18, 78.08, 13.64 and >100μM for 1; 31.87, >100, ~100, >100μM for 3, respectively.     

Two new diterpenoids and other constituents from Isodon rubescens

Two new ent-kaurene diterpenoids, 15α-acetoxyl-6,11α-epoxy-6α-hydroxy-20-oxo-6,7-seco-ent-kaur-16-en-1,7-olide (1), 15α-hydroxy-20-oxo-6,7-seco-ent-kaur-16-en-1,7α(6,11α)-diolide (2), together with ten known compounds (5-14) were isolated from the leaves of Isodon rubescens. Their structures were elucidated mainly by various spectroscopic techniques and finally confirmed by single-crystal X-ray diffraction. Compounds 1, 2, 8 and 12 were evaluated for their cytotoxicities against EC-1, U87, A549, MCF-7 and Hela cell lines.     

Asterosaponins from the starfish Culcita novaeguineae and their bioactivities

Bioassay-guided fractionation of the n-BuOH extract of the starfish Culcita novaeguineae resulted in the isolation of one new sulfated steroidal glycoside (asterosaponin) (1), along with three known asterosaponins, thornasteroside A (2), marthasteroside A(1) (3) and regularoside A (4), as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. Their structures were elucidated by extensive spectral studies and chemical evidences. All the saponins showed moderate cytotoxicity against cancer cell lines K-562 and BEL-7402.     

Antiplasmodial activity and cytotoxicity of Albertisia delagoensis

Leaves and rhizome methanol extracts of Albertisia delagoensis tested positive against Plasmodium falciparum, with a very low cytotoxic activity in leaves against the Graham cell line.     

Cytotoxic sesquiterpenoids from the fruits of Lindera communis

A new sesquiterpenoid, namely Linerenone (1), together with three known sesquiterpenoids (2–4), were isolated from the fruits of Lindera communis. Their structures were determined by extensive spectroscopic analysis including 1D, 2D-NMR and HR-MS spectra. Compound 1 showed significant cytotoxic activity against H460, ES2 and DU145 cancer cells with IC₅₀ of 2.1 μg/mL, 2.8 μg/mL and 3.0 μg/mL, respectively.     

Two new biphenanthrenes with cytotoxic activity from Bulbophyllum odoratissimum

Two new dimeric phenanthrenes, bulbophythrins A (1) and B (2), were isolated from Bulbophyllum odoratissimum. Their structures were elucidated by HR-ESI-MS, 1D and 2DNMR spectroscopy. They were evaluated in vitro for their inhibitory ability against the growth of human leukemia cell lines K562 and HL-60, human lung adenocarcinoma A549, human hepatoma BEL-7402 and human stomach cancer SGC-7901. Both compounds showed significant cytotoxicity against the tested cell lines. Compound 1 exhibited some selectivity against HL-60 and BEL-7402 with IC₅₀ values of 1.27 × 10^− 3 and 1.22 × 10^− 3 µmol/ml respectively, whereas 2 was most active against A549 with IC₅₀ value of 1.18 × 10^− 3 µmol/ml.