Two new compounds and anti-HIV active constituents from Illicium verum

Two new compounds named illiverin A (1) and tashironin A (8) were isolated from the roots of Illicium verum, together with seven known compounds: 4-allyl-2-(3-methylbut-2-enyl)-1,6-methylenedioxybenzene-3-ol (2), illicinole (3), 3-hydroxy-4,5-methylenedioxyallyl-benzene (4), (-)-illicinone-A (5), 4-allyl-4-(3-methylbut-2-enyl)-1,2-methylenedioxycyclohexa-2,6-dien-5-one (6), 3,4-seco-(24 Z)- cycloart-4(28),24-diene-3,26-dioic acid, 26-methyl ester (7) and tashironin (9). Based on 1D- and 2D-NMR data (COSY, HMQC, HMBC), the structures of the new compounds were deduced to be (E)-1-[(3-methylbut-2-enyl)oxy]-2-methoxy-4-(prop-1-enyl)benzene (1) and 11-O-debenzoyl-11alpha-O-2-methylcyclopent-1-enecarboxyltashironin (8). Compounds 1-9 were screened for anti-HIV activity in vitro whereby compounds 5 and 7 possessed moderate anti-HIV activity with EC50 values of 16.0 and 5.1 microM with SI values of 18.2 and 15.6, respectively.     

Phenolic compounds from the aqueous extract of Acacia catechu

Two new phenolic compounds, 5-hydroxy-2-[2-(4-hydroxyphenyl) acetyl]-3-methoxylbenzoic acid (1) and (2S,3S)-3,7,8,3',4'-pentahydroxyflavane (2), were obtained from the aqueous extract of Acacia catechu, along with four known compounds identified as rhamnetin (3), 4-hydroxyphenyl ethanol (4), 3,3',5,5',7-pentahydroxyflavane (5), and fisetinidol (6). Their structures were determined on the basis of spectroscopic analysis. Free radical-scavenging activities of the new compounds were evaluated.     

Five new compounds from Dendrobium longicornu

A novel bibenzyl, a new bibenzyl, two new phenanthrenes, and a new lignin glycoside, namely longicornuol A (1), 4-[2-(3-hdroxyphenol)-1-methoxyethyl]-2,6-dimethoxyphenol (2), 5-hydroxy-7-methoxy-9,10-dihydrophenanthrene-1,4-dione (3), 7-methoxy-9,10-dihydrophenanthrene-2,4,5-triol (4) and erythro-1-(4-O-beta-D-glucopyranosyl-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]-1,3-propanediol ( 5), together with 14 known compounds, were isolated from the stems of Dendrobium longicornu. All structures were elucidated by spectroscopic methods (NMR, MS, UV and IR). Anti-platelet aggregation activities of compounds 1 - 5 were also tested.     

New alpha-pyrrolidinonoids and glycosides from Euphorbia humifusa

A phytochemical investigation on the constituents from Euphorbia humifusa Willd. has resulted in the isolation of three new alpha-pyrrolidinonoidal compounds, 5beta-methoxy-4beta-hydroxy-3-methylene-alpha-pyrrolidinone (1), 5beta-methoxy-4alpha-hydroxy-3-methylene-alpha-pyrrolidinone (2), and 5beta-butoxy-4alpha-hydroxy-3-methylene-alpha-pyrrolidinone (3), and three new glycosides including an indole glycoside, 3-(2-hydroxyethyl)-5-(1-O-beta-glucopyranosyloxy)-indole (4), an ionone glycoside, 3-oxo-7,8-dihydro-alpha-ionone-11-O-beta-glucoside (5), and a hemiterpene glycoside, 1-(4-hydroxy-2-methyl-2-buten-1-yl)-6- (3,4,5-trihydroxybenzoyl)-beta-d-glucose (6), along with 10 known compounds. Their structures were elucidated by analysis of 1D and 2D NMR spectral data. The structure of 1 was further confirmed by a single-crystal X-ray diffraction analysis.     

Chromone glycosides from Knoxia corymbosa

Four new chromone glycosides, corymbosins K1-K4 (3-6), together with two known compounds, noreugenin (1) and undulatoside A (2), were isolated from the whole plant of Knoxiacorymbosa (Rubiaceae). The structures of the new compounds were established through extensive NMR or X-ray spectroscopic analysis as 7-O-beta-D-allopyranosyl-5-hydroxy-2-methylchromone (corymbosin K1, 3), 7-O-beta-D-6-acetylglucopyranosyl-5-hydroxy-2-methylchromone (corymbosin K2, 4), 7-O-[6-O-(4-O-trans-caffeoyl-beta-D-allopyranosyl)]-beta-D-glucopyranosyl-5-hydroxy-2-methylchromone (corymbosin K3, 5) and 7-O-[6-O-(4-O-trans-feruloyl-beta-D-allopyranosyl)]-beta-D-glucopyranosyl-5-hydroxy-2- methylchromone (corymbosin K4, 6). Compounds 2-5 were subjected to test their immunomodulatory activity invitro.     

Two new derivatives of griseofulvin from the mangrove endophytic fungus Nigrospora sp. (strain No. 1403) from Kandelia candel (L.) Druce

Two new compounds, methyl 3-chloro-6-hydroxy-2-(4-hydroxy-2-methoxy-6-methylphenoxy)-4-methoxybenzoate (1) and (2 S,5' R,E)-7-hydroxy-4,6-dimethoxy-2-(1-methoxy-3-oxo-5-methylhex-1-enyl)-benzofuran-3(2H)-one (2), together with four known compounds, griseofulvin (3), dechlorogriseofulvin (4), bostrycin (5), and deoxybostrycin (6), were isolated from the marine endophytic fungus NIGROSPORA sp. (No.?1403) collected from the South China Sea. The structures were elucidated by spectroscopic methods, 1D, 2D NMR, and HREIMS. Compounds 5 and 6 showed moderate antitumor and moderate antimicrobial activity.     

Novel cadinane and norcadinane sesquiterpenes and a new propanoate from Goldfussia psilostachys

Three new compounds, goldfussins A (1) and B (2) and goldfussinol (3), and sixteen known compounds were isolated from the ethanolic extract of the whole plants of Goldfussia psilostachys. The structures of the new compounds were elucidated as a novel cadinane sesquiterpene, 1,8-dimethyl-5-hydroxymethyl-9-oxo-6,7,8,9-tetrahydronaphtho[2,1- b]furan (1), a novel norcadinane sesquiterpene, 4-acetyl-3-hydroxy-1-hydroxymethyl-6-methyl-5-oxo-5,6,7,8-tetrahydronaphthalene (2) and methyl 3-hydroxy-2-(3,5-dimethoxy-4-hydroxyphenyl)-propanoate (3) on the basis of spectral data.     

Anti-complement activity of norlignans and terpenes from the stem bark of Styrax japonica

A new norlignan, styraxlignolide A (1), and two new terpenes, styraxosides A (2) and B (3), were isolated from the MeOH-soluble fraction of Styrax japonica Sieb. et Zucc. (Styracaceae) stem bark, together with two known compounds, egonol (4) and masutakeside I (5). The new compounds were determined as 5-(3'-hydroxypropyl)-7-methoxy-2-(3',4'-dimethoxyphenyl)-benzofuran 3'- O-[beta-D-xylopyranoside-(1-->6)-beta- D-glucopyranoside] (1), 3beta,7beta-dihydroxy-4alpha,4beta,8beta,10beta,14alpha-pentamethyl-5alpha-gon-16-en-2-one 3-O-[beta-D-glucopyranoside-(1-->2)-beta-D-glucopyranoside] (2), and 3beta,17beta-dihydroxy-28-norolean-12-en-16-one 3-O-[alpha-L-rhamopyranoside-(1-->2)-beta-D-glucuronopyranoside] (3) by spectroscopic means including 2D-NMR. The five compounds were tested in vitro for anti-complement activity against the complement system. Compounds 1, 3, 4, and 5 displayed inhibitory activity in the anti-complement assay, with IC50 values of 123, 65, 33, and 166 microM, respectively. Compound 1a and camellenodiol (3a), obtained from acid hydrolysis of 1 and 3, respectively, did not affect the hemolytic activity of human serum against sensitized erythrocytes. This shows that a sugar seems to play a role of enhancing significantly anti-complement activity.     

Cytotoxic terpene hydroperoxides from the aerial parts ofAster spathulifolius

Three new sesquiterpene hydroperoxides, 1-[3-(2-hydroperoxy-3-methylbut-3-en)-4-hydroxyphenyl]ethanone (2), 7beta-hydroperoxy-eudesma-11-en-4-ol (3), and 7alpha-hydroperoxymanool (4), together with three known compounds, germacrone (1), ent-germacra-4(15),5,10(14)-trien-1alpha-ol (5) and teucdiol A (6) were isolated from the aerial parts of Aster spathulifolius (Compositae). Their structures were characterized using chemical and spectroscopic methods. The isolated compounds were tested for their cytotoxicity against five human tumor cell lines in vitro using a SRB method. The two new compounds, 3 and 4, showed moderate cytotoxicity against human cancer cells with ED50 values ranging from 0.24 to 13.27 microg/mL.     

Jacaranone and related compounds from the fresh fruits ofTernstroemia japonica and their antioxidative activity

Jacaranone and related compounds (1-3) were isolated, along with three triterpenes (4-6), from the fresh fruits of Ternstroemia japonica. The compounds were identified as jacaranone (1), 3-hydroxy-2,3-dihydrojacaranone (2), 3-methoxy-2,3-dihydrojacaranone (3), 3-O-acetyloleanolic acid (4), 3-O-acetylursolic acid (5), and ursolic acid (6). Jacaranone and its derivatives were isolated for the first time from Theaceae. Of the isolated compounds, compound 3 is a new compound. Jacaranone (1) exhibited weak antioxidative effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical.     

黄丝郁金中的生物碱和倍半萜类成分

姜科植物姜黄(Curcuma longa)的块根称为黄丝郁金，是常用中药郁金的来源之一。为了研究黄丝郁金的利胆活性成分，采用柱色谱法对姜黄干燥块根的化学成分进行了研究。本文主要报道从中分离得到的1个喹啉类生物碱2-(2′-methyl-1′-propenyl)-4,6-dimethyl-7-hydroxyquinoline (1)，7个没药烷型倍半萜2,5-dihydroxybisabola-3,10-diene (2), 4,5-dihydroxybisabola-2,10-diene (3), turmeronol A (4), bisacurone (5), bisacurone A (6), bisacurone B (7)和bisacurone C (8)，以及dehydrozingerone (9)和zingerone (10)的分离和鉴定。化合物1为一个新的生物碱类化合物，化合物6～8为首次从姜黄中分得，化合物9～10为首次从姜黄属植物中分离得到。     

Sesquiterpenoids and other constituents from the flower buds of Tussilago farfara

One new norsesquiterpenoid, namely tussfarfarin A (1), and four new artifacts resulting from extraction procedure, namely tussfarfarin B (2), 6-(1-ethoxyethyl)-2,2-dimethylchroman-4-ol (3), 5-ethoxymethyl-1H-pyrrole-2-carbaldehyde (4), and 3β-hydroxy-7α-ethoxy-24β-ethylcholest-5-ene (5), along with 18 known compounds, were isolated from the flower buds of Tussilago farfara. Their structures were elucidated by extensive spectroscopic analysis.     

Two new aromatic compounds from the resin of Styrax tonkinensis (Pier.) Craib

Two new aromatic compounds, trans-(tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-5-oxofuran-3-yl)methyl benzoate (1), 3-(4-hydroxy-3-methoxyphenyl)-2-oxopropyl benzoate (2) and one new natural product, 4-((E)-3-ethoxyprop-1-enyl)-2-methoxyphenol (3) together with five known aromatic compounds have been isolated from the resin of Styrax tonkinensis (Pier.) Craib. Their structures were determined by physical and spectroscopic methods.     

Minor compounds from the stem bark of Chinese mangrove associate Catunaregam spinosa

A new dihydroisocoumarin 3-(2-hydroxypropyl)-8-hydroxyl-3,4-dihydroisocoumarin (1) and a new iridoid 3-deoxyartselaenin C (5), together with six known compounds scopoletin (2), scoparone (3), morindolide (4), pinoresinol (6), medioresinol (7), and secoisolariciresinol (8) were isolated from the stem bark of Chinese mangrove associate Catunaregam spinosa Tirveng. The structures of 1 and 5 were determined by extensive spectroscopic analysis, including 1D and 2D NMR data. All compounds except 2 were obtained from C. spinosa for the first time. And it was also the first time lignans were obtained from Catunaregam sp.     

北沙参中一个新香豆素苷

为了研究北沙参的化学成分，本文通过大孔树脂吸附柱色谱、Sephadex LH-20及开放反相ODS柱色谱进行化合物的分离，利用多种波谱技术鉴定化合物结构。分离得到9个化合物，鉴定为：bergaptol 5-O-β-D-gentiobioside (1)、(7R，8S)-dehydrodiconiferylalcohol-4，9-di-O-β-D-glucoside (2)、橙皮素A(3)、(-)-seco-isolariciresinol 4-O-β-D-glucopyranoside (4)、白花前胡苷(5)、花椒毒酚8-O-β-D-吡喃葡糖苷(6)、5′-硫甲基腺苷(7)、腺苷(8)、色氨酸(9)。化合物1为新化合物；化合物2和7为首次从该属植物中分离得到。     

Flavonoids from<Emphasis Type="Italic">Iris spuria</Emphasis> (Zeal) cultivated in Egypt

A new 12a-dehydrorotenoid 1, 11-dihydroxy-9, 10-methylenedioxy-12a-dehydrorotenoid (1), together with a new isoflavonoid glycoside tectorigenin-7-O-beta-glucosyl-4'-O-beta-glucoside (3), were isolated and identified from the rhizomes of I. spuria (Zeal). In addition, 4 known compounds, tectorigenin (2) tectorigenin-7-O-beta-glucosyl (1 --> 6) glucoside (4), tectoridin (a tectorigenin-7-O-beta-glucoside) (5) and tectorigenin-4'-O-beta-glucoside (6) were isolated and identified for the first time from this plant. The structures of the isolated compounds were determined by spectroscopic methods (UV, IR, 1H, 13C-NMR, DEPT, HMQC, NOESY, and HMBC experiments and MS spectrometry) and by comparison with literature data of known compounds. Compounds 2, 4, 5, and 6 are reported for the first time from this plant through the present study.     

Bioactive terpenes from the roots of Chloranthus henryi

12,15-Epoxy-5alpha H,9beta H-labda-8(17),13-dien-19-oic acid (1) and 14-methoxy-15,16-dinor-5alpha H,9alpha H-labda-13(E),8(17)-dien-12-one (2), two new labdane-type diterpenes, and 1alpha-hydroxy-8,12-epoxyeudesma-4,7,11-triene-6,9-dione (3), one new eudesmane-type sesquiterpene, were isolated from Chloranthus henryi Hemsl, along with two known compounds, 8beta H-eudesma-4(14),7(11)-dien-12,8-olide (4) and 8beta-hydroxyeudesma-4(14),7(11)-dien-12,8-olide (5). Their structures were established by a combination of 1D- and 2D-NMR spectroscopic techniques. The new compounds 2, 3 and the known compound 4 exhibited antitumor activities against Hela and K562 human tumor cell lines.     

Three new polymeric isopropenyl benzofurans from Ligularia stenocephala

Three new polymeric isopropenyl benzofurans, 4-methyl-2,4-bis(5,6-dimethoxy-2-benzofuranyl)-1-pentene, stenocephalin A (1), 4,6-dimethyl-2,4,6-tri(5,6-dimethoxy-2-benzofuranyl)-1-heptene, stenocephalin B (2) and 4,6,8-trimethyl-2,4,6,8-tetra(5,6-dimethoxy-2-benzofuranyl)-1-nonene, stenocephalin C (3), together with seven known compounds (4-10) were isolated from the roots of Ligularia stenocephala. The structures of the new compounds were elucidated on the basis of spectral evidence, especially on 2D NMR. In addition, the cytotoxic activity and the anti-bacterial activity of compounds 2, 3, 5 and 6 were tested.     

A new pregnane glycoside and oligosaccharide from Parabarium huaitingii

Two new compounds, along with two known compounds, were isolated from the barks of Parabarium huaitingii, and their structures were determined as 5α-pregn-6-ene-3β,17α,20(S)-triol-20-O-β-d-digitoxopyranoside (1), cymaropyranurolactone 4-O-β-d-digitalopyranosyl-(1?→?4)-O-β-d-cymaropyranosyl-(1?→?4)-O-β-d-oleandropyranosyl-(1?→?4)-O-β-d-cymaropyranoside (2), 3β,17α,20(S)-trihydroxy-5α-pregn-6-ene (3), and 5α-pregn-6-ene-3β,17α,20(S)-triol-3-O-β-d-digitalopyranoside (4) by spectroscopic methods.     

Sesquiterpene lactone glycosides,eudesmanolides, and other constituents from Carpesium macrocephalum

Two new sesquiterpene lactone glycosides and two new eudesmanolides, along with twelve known compounds were isolated from seeds of Carpesium macrocephalum. The structures of these new compounds were elucidated as 2alpha- O-beta- D-glucopyranosyl-5alpha, 11alpha H-eudesma-4(15)-en-12,8beta-olide ( 1), 2alpha- O-beta- D-glucopyranosyl-5alpha H-eudesma-4(15),11(13)-dien-12,8beta-olide ( 2), 2alpha-acetoxy-5alpha-hydroxy-11alpha H-eudesma-4(15)-en-12,8beta-olide ( 3) and 2alpha,5alpha-dihydroxy-11alphaH-eudesma-4(15)-en-12,8beta-olide ( 4) by spectroscopic methods including 2D NMR techniques ( (1)H- (1)H COSY, (1)H- (1)H NOESY, HMQC, HMBC) and chemical transformations. Compounds 1, 6, 8, 9 and 10 exhibited moderate antibacterial activity, while compound 4 showed appreciable cytotoxic activity against cultured SMMC-7721 (human hepatoma cell).