Diarylheptanoids from the rhizomes of Alpinia officinarum and their anticancer activity

Two new diarylheptanoids (1, 2), together with two known analogs (3, 4), were isolated from the rhizomes of Alpinia officinarum. The new compounds were elucidated to be (5S)-5-hydroxy-7-(3, 4-dihydroxyphenyl)-1-phenyl-3-heptanone (1) and (5R)-5-hydroxy-7-(3-methoxy-4, 5-dihydroxyphenyl)-1-phenyl-3-heptanone (2) based on their spectral analysis. Compound 4 showed moderate cytotoxicity against human tumor cell lines, HepG2, MCF-7 and SF-268, while no significant effect were found for compounds 1-3.     

Heptaketides with antiviral activity from three endolichenic fungal strains Nigrospora sp., Alternaria sp. and Phialophora sp

Two new heptaketides, (+)-(2S,3S,4aS)-altenuene (1a) and (-)-(2S,3S,4aR)-isoaltenuene (2a), together with six known compounds, (-)-(2R,3R,4aR)-altenuene (1b), (+)-(2R,3R,4aS)-isoaltenuene (2b), 5'-methoxy-6-methyl-biphenyl-3,4,3'-triol (3), alternariol (4), alternariol-9-methyl ether (5), and 4-hydroxyalternariol-9-methyl ether (6) were isolated from the EtOAc extract of an endolichenic fungal strain Nigrospora sphaerica (No.83-1-1-2). Compounds 1a and 1b were separated from enantiomers 1 by chiral HPLC, and so were 2a and 2b from enantiomers 2. Interestingly, 1-6 were also obtained from other two endolichenic fungal strains Alternaria alternata (No.58-8-4-1) and Phialophora sp. (No.96-1-8-1). The structures of 1-6 were elucidated by means of MS, HR-MS, NMR, and X-ray diffraction. Furthermore, the absolute configurations of 1a-2b were determined by CD experiments and CD calculation. Of these compounds, 4 and 5 showed antiviral activity against herpes simplex virus (HSV) in vitro, with IC(50) values of 13.5 and 21.3 μM, and with selective index (SI) values of 26.5 and 17.1, respectively.     

Amides with anti-platelet aggregation activity from Piper taiwanense

Three new amides, taiwanamides A-C (1-3), and two known amides, 1-cinnamoylpyrrolidine (4) and 1-(m-methoxycinnamoyl)pyrrolide (5), have been isolated from the stem of Piper taiwanense. The structures of the new amides were determined by spectral analyses. These five amides exhibited inhibitory activity of platelet aggregation in vitro. Taiwanamide C (3) owned the most potent inhibition activity of platelet aggregation induced by collagen showing IC(50) value as 8.9 microM. Taiwanamide B (2) and 1-(m-methoxycinnamoyl)pyrrolide (5) exhibited IC(50) values of 17.3 and 17.4 microM, respectively.     

Homoisoflavanones from Ledebouria floribunda

The bulbs of Ledebouria floribunda (Baker) Jessop have yielded two novel compounds, 7-O-[α-rhamnopyranosyl-(1→6)-β-glucopiranosyl]-5-hydroxy-3-(4-methoxybenzyl)-chroman-4-one (1) and 7-O-[α-rhamnopyranosyl-(1→6)-β-glucopiranosyl]-5-hydroxy-3-(4′-hydroxybenzyl)-chroman-4-one (2) along with five other known compounds, 5,7-dihydroxy-3-(4′-methoxybenzyl)-chroman-4-one or 3,9-dihidroeucomin (3), 5,7-dihidroxy-6-methoxy-3-(4′-methoxybenzyl)-chroman-4-one (4), 5,7-dihidroxy 3-(4′-hydroxybenzyl)-chroman-4-one or 4,4′-demethyl-3,9-dihydropuctatin (5), 5,7-dihidroxy-3-(4′-hydroxybenzyl)-6-methoxy-chroman-4-one or 3,9-dihydroeucomnalin (6) and 7-hydroxy-3-(4′-hydroxybenzyl)-5-methoxy-chroman-4-one (7). Their structures were elucidated by spectra analysis. The seven homoisoflavanones were found to be antioxidant against DPPH radical and β-carotene/linoleic acid system.     

In vivo antidepressant activity of sesquiterpenes from the roots of Valeriana fauriei Briq

Antidepressant activity-guided fractionation of the MeOH extract of Valeriana fauriei Briq. roots resulted in the isolation of two new germacrane-type sesquiterpenes (1-2) in addition to seven known ones (3-9). Their structures were elucidated as 1β,10α-dihydroxyl-8α-acetoxyl-10β,11,11-trimethyl-4-formyl-bicyclogermacren-E-4(5)-ene (1), 1β-hydroxyl-8α-acetoxyl-11,11-dimethyl-4-formyl-bicyclogermacren-E-4(5),10(14)-diene (2), bicyclo[8,1,0]5β-hydroxyl-7β-1acetoxyl-5α,11,11'-trimethyl -E-1(10)-ene-4α,15-olide (3), 8α-acetoxyl-3α,4α,10-trihydroxyl-guaia-1(2)-ene-12,6α-olide (4), 2-Ethylhexyl-4-hydroxybenzoate (5), 11αH-gemacra-1(10)E,4Z-diene-3-one-12,6α-olide (6), β-Sitoterol (7), isovaleric acid (8), isoborneol acetate (9), using a combination of UV, IR, mass spectroscopy, 1D and 2D NMR spectroscopy. The antidepressant activity of compounds 1-4 was investigated by the FST on mice. Among them, compounds 3 and 4 showed the significant antidepressant activity (*, P<0.01).     

2-aryl benzofurans and their derivatives from seeds of Styrax macranthus

Two new 2-aryl benzofuran derivatives, 3-[7-methoxy-2-(3,4-methylenedioxyphenyl) benzofuran-5-yl]propyl 3-[7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran-5-yl]propanoate (1) and demethoxy egonol gentiobioside (2), were isolated from the aqueous ethanolic extract of the seeds of Styrax macranthus, together with 7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran-5-carbaldehyde, egonol, demethoxy egonol, demethyl egonol, egonol glucoside, egonol gentiobioside, egonol gentiotrioside, stigmasterol, 2,3-dihydroxypropyl tetracosoate, and daucosterol. Their structures were elucidated on the basis of spectral and chemical evidence.     

Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: confirmation of their synonymy

A new spirostanol saponin (1), along with four known saponins, dioscin (2), protodioscin (3), methyl-protodioscin (4), and indioside D (5), and one known steroid glycoalkaloid solamargine (6) were isolated from the two synonymous species, Solanum incanum and S. heteracanthum. The structure of the new saponin was established as (23S,25R)-spirost-5-en-3β,23-diol 3-O-{β-D-xylopyranosyl-(1→2)-O-α-L-rhamnopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside}, by using a combination of 1D and 2D NMR techniques including (1)H, (13)C, COSY, TOCSY, NOESY, HSQC and HMBC experiments and by mass spectrometry. The compounds 1, 3, 4 and 5 were evaluated for cytotoxicity against five cancer cell lines and for antioxidant and cytoprotective activity.     

Cardiovascular effects of Sida cordifolia leaves extract in rats

The cardiovascular activity of the aqueous fraction of the hydroalcoholic extract of Sida cordifolia leaves (AFSC) was evaluated. In normotensive non-anaesthetized rats was observed that AFSC (5, 10, 20, 30 and 40 mg/kg, i.v.) induced hypotension (6 +/- 2%; 8 +/- 2%; 11 +/- 2%; 19 +/- 3% and 33 +/- 3%, respectively) and bradycardia (0.3 +/- 3%; 13 +/- 4%; 38 +/- 6%; 64 +/- 7% and 80 +/- 5%, respectively). Hypotensive response was completely abolished after atropine (2 mg/kg; i.v.) but potentialized after hexamethonium (20 mg/kg; i.v.) (12 +/- 2%; 21 +/- 5%; 28 +/- 3%; 32 +/- 2% and 32 +/- 3%, respectively), while bradycardic response was completely abolished after atropine (2 mg/kg; i.v.) and attenuated with hexamethonium (20 mg/kg; i.v.) (1 +/- 0.3%; 5 +/- 1%; 7 +/- 1%; 7 +/- 1% and 10 +/- 1%, respectively). In hexamethonium treated rats, L-NAME significantly attenuated the hypotensive response (9 +/- 2%; 14 +/- 1%; 16 +/- 1%; 16 +/- 2% and 22 +/- 3%, respectively). In normotensive anaesthetized and vagotomized rats, hypotensive and bradycardic responses were significantly attenuated (0.5 +/- 0.2%; 1 +/- 0.4%; 3 +/- 0.6%; 4 +/- 0.8% and 6 +/- 1%, respectively, n = 6, and 7 +/- 2%; 12 +/- 5%; 15 +/- 2%, 17 +/- 2% and 25 +/- 3%, respectively). The anaesthesia with sodium thiopental did not affect the AFSC-induced responses when compared with those induced in non-anaesthetized rats (data not showed). In conclusion, the results obtained so far show that AFSC produce hypotension and bradycardia, mainly due to a direct stimulation of the endothelial vascular muscarinic receptor and indirect cardiac muscarinic activation, respectively.     

Anthelmintic activities of three medicinal plants from Nigeria

Aqueous extracts of the leaf, stem bark and root bark from Canna bidentata, Spondias mombin and Commiphora africana were examined for anthelmintic activity against earthworm. All the extracts demonstrated a concentration-dependent activity at tested concentrations of 10-80 mg/ml. Higher activities were observed at the higher concentrations, 40-80 mg/ml for all the plant extracts. C. bidentata with a paralysis time of 3-5 min and death time of 5-18 min at these concentrations for the stem bark, and S. mombin which exhibited comparatively higher efficacy (34-44 min paralysis time and 105 min death time for the leaf) at lower concentrations of 10-20 mg/ml were adjudged the outstanding anthelmintics of plant origin accordingly.     

Anti-neuroinflammatory constituents from Polygala tricornis Gagnep

Two new compounds (S)-(+)-butyl-4-methylene-5-oxo-pyrrolidin-2-carboxylate (1) and (5-formylfuran-2-yl)methyl 4-hydroxy-2-methylenebutanoate (2), together with four known compounds (3-6) were isolated from the roots of Polygala tricornis Gagnep. Their structures were determined on the basis of 1D- and 2D-NMR experiments and by comparison with physical data of known compounds. All the isolated compounds were examined for their inhibitory effect on the nitric oxide (NO) production induced by lipopolysaccharide (LPS) in BV-2 microglial cells, and compounds 1 and 2 exhibited pronounced inhibition on the NO production with IC(50) values of 14.1 μM and 1.77 μM, respectively.     

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.     

Bioactive phenolics from the fruits of Livistona chinensis

This study investigated the antioxidant and cytotoxic activity of the phenolics isolated from the fruits of Livistona chinensis. Four new compounds, 1-{ω-isoferul[6- (4-hydroxybutyl)pentadecanoic acid]}-glycerol (1), E-[6′-(5″-hydroxypentyl)tricosyl]-4-hydroxy-3-methoxycinnamate (2), 2-(3′-hydroxy-5′-methoxyphenyl)-3-hydroxylmethyl-7-methoxy-2,3-dihydrobenzofuran-5- carboxylic acid (3), 7-hydroxy-5,4′-dimethoxy-2-arylbenzofuran (4), together with eleven known phenolics (5-15), were isolated and identified. Among these compounds, 1-4, 5-O-caffeoylshikimic acid (5), caffeic acid (7), and 3-O-caffeoylshikimic acid (8) showed potent antioxidant activity. 1-5, and 8 showed potent antiproliferative activities with IC₅₀ values among 5-150 μM against HepG2 human liver cancer, HL-60 human myeloid leukemia, K562 human myeloid leukemia, and CNE-1 human nasopharyngeal carcinoma cell lines. On the basis of these findings, it could be proposed that the fruits of L. chinensis may serve as attractive mines of powerful anticancer and antioxidant agents for various purposes.     

Three new antibacterial active diarylheptanoids from Alpinia officinarum

Three new diarylheptanoids, together with ten known ones, were isolated from the ethanol extract from the rhizomes of Alpinia officinarum Hance. The structural identification of these compounds was mainly achieved by spectroscopic methods. The new compounds were elucidated as 7-(4″, 5″-dihydroxy-3″-methoxyphenyl)-1-phenyl -4-heptene-3-one (1), 1, 7-diphenyl-5-heptene-3-one (2) and 4-phenethyl-1, 7-diphenyl -1-heptene-3, 5-dione (3), respectively. All of the compounds showed antibacterial activity against Helicobactor pylori. Especially, the three new compounds showed strong antibacterial activity against Hp-Sydney strain 1 with the MIC values of 9–12 μg/mL, and against Hp-F44 with the MIC values of 25–30 μg/mL.     

Potent and selective butyrylcholinesterase inhibitors from Ficus foveolata

Four stilbenes (1-4), one inseparable mixture of two alkyl diferulates (5a, 5b), one alkyl ferulate (6) and four flavonoids (7-10) were isolated from Ficus foveolata Wall. Except for quercetin (10), the other ten constituents were isolated from F. foveolata for the first time. In addition, one of the two components in mixture 5 is a new compound identified as (1E,22E)-1,22-docosanediol diferulate (5a). All nine isolated compounds, plus the mixture of 5a and 5b known as 5, exhibited a low or no activity against acetylcholinesterase. However, and interestingly, the stilbenes 1-4 showed a high inhibition towards butyrylcholinesterase. Gnetol (4) had the lowest IC(50) value of 1.3μM towards butyrylcholinesterase and showed a reversible and competitive inhibition in the kinetic study.     

Cytotoxic sesquiterpenes and lignans from Saussurea deltoidea

Two new sesquiterpenes deltoiden A (1) and deltoiden B (2), and two new lignans deltoignan A (9) and deltoignan B (10), together with 14 known compounds, including six sesquiterpenes 3-8 and three lignans 11-13, were isolated from the whole plant of Saussurea deltoidea. Compounds 3-8 and 11-17 were isolated for the first time from this plant. Their structures were established by spectroscopic analysis, including 2D-NMR spectroscopic techniques. Cytotoxicities of compounds 1-13 were tested against three cancer cell lines A549, Hela and SMMC-7721. Results showed that 5, 6 and 7 exhibited cytotoxicity against SMMC-7721 with the IC(50) values of 6.49, 9.53, 1.23 μg/ml, 5 and 7 against A549 with the IC(50) values of 4.99 and 5.35 μg/ml, 5, 6, 7, 13 against Hela with the IC(50) values of 1.40, 4.75, 0.93 and 5.42 μg/ml, respectively. The structure-activity relationships of sesquiterpenes 1-8 were discussed on the base of cytotoxic results.     

New cytotoxic quinolone alkaloids from fruits of Evodia rutaecarpa

Three new quinolone alkaloids, 1-methyl-2-[7-hydroxy-(E)-9-tridecenyl]-4(1H)-quinolone (1), 1-methyl-2-[(Z)-4-nonenyl]-4(1H)-quinolone (2), 1-methyl-2-[(1E,5Z)-1,5-undecadienyl]-4(1H)-quinolone (3) and one new natural product, 1-methyl-2-[(E)-1-undecenyl]-4(1H)-quinolone (4), were isolated from the dried and nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth., along with thirteen known compounds (5-17). In addition, one new artificial product, 1-methyl-2-[7-carbonyl-(E)-9-tridecenyl]-4(1H)-quinolone (1A) was also obtained. The structures of these compounds were determined by spectroscopic analyses. The cytotoxic activities of all of the compounds against the human cancer cell lines HL-60, N-87, H-460, and Hep G(2) cells were evaluated by MTT assay. The results showed that these alkaloids inhibited cell proliferation with IC(50) values between 14μM and 22μM.     

白皮松天然群体遗传多样性的EST-SSR分析

为探讨白皮松群体间遗传变异规律,使用7对EST-SSR引物对分布区内21个白皮松天然群体的遗传多样性及遗传分化水平进行了研究。结果表明:7对引物在21个白皮松天然群体的663个单株中共检测到14个多态性位点。各群体间有效等位基因数(Ne)、Shannon’s信息指数(I)、观测杂合度(Ho)、期望杂合度(He)、Nei’s期望杂合度(Nei’s)分别为1.156 5 1.601 9、0.133 5 0.492 5、0.138 4 0.397 3、0.0860 0.342 8、0.084 6 0.337 4。白皮松群体间遗传分化系数(Fst)平均为0.215 2,基因流(Nm)值平均为0.911 9,群体间基因交流总体较少,遗传分化较大。白皮松多样性水平在分布区内呈规律性变化,多样性分布的中心区域主要在西部、南部,具有从西向东,从南向北依次减少的趋势。     

Steroidal saponins from Smilacina japonica

Three new steroidal saponins, japonicoside A (1), japonicoside B (2) and japonicoside C (3) were isolated from the dried rhizomes and roots of Smilacina japonica A. Gray. Their structures were elucidated as (25S)-5α-spirostan-9(11)-en-3β-ol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1), (25S)-5α-spirostan-9(11)-en-3β,17α-diol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (2) and (25S)-5α-spirostan-9(11)-en-3β,17α,24α-triol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (3) on the basis of chemical methods and detailed spectroscopic analysis, including 1D, 2D NMR and HR-ESI-MS. The cytotoxicity of isolated compounds was evaluated in vitro for cytotoxic properties against human hepatocellular carcinoma cells (SMMC-7221) and human colorectal adenocarcinoma cells (DLD-1), respectively.     

Endothelium-independent relaxation of aorta rings by two stilbenoids from the orchids Scaphyglottis livida

Gigantol (1) and 3,7-dihydroxy-2,4-dimethoxyphenanthrene (2) from the orchid Scaphyglottis livida induced a significant concentration-dependent relaxation of the contractions evoked by noradrenaline (NA) in endothelium-intact and denuded rat aorta rings. Incubation with N(G)-nitro-L-arginine methyl ester (L-NAME, 1x10(-5) M) or methylene blue (MB, 1x10(-7) M) significantly reduced the relaxation induced by the stilbenoids 1 and 2. The results suggested that two or more mechanisms are involved in the vasorelaxant effects of both compounds.     

A new epicatechin gallate and calpain inhibitory activity from Orostachys japonicus

Calpains are calcium-dependent proteases that cleave a variety of intracellular substrates. The overactivation of mu-calpain is associated with a wide range of disease conditions. To search for calpain inhibitors from natural products, the phytochemical constituents of the ethyl acetate fraction of the whole plant of Orostachys japonicus (Crassulaceae) were studied. The various chromatographic separation of this fraction led to the isolation of a new tannin, (-)-epicatechin 5-gallate (1) along with 9 known compounds. Their structures were elucidated by spectroscopic and chemical analyses. Among them, (-)-epicatechin 5-gallate (1) and kaempferol (9) exhibited moderate inhibitory activity against mu-calpain with IC(50) values of 18.0+/-2.9 and 15.4+/-2.0 microg/ml, respectively.