Biphenyl glycosides from the fruit of Pyracantha fortuneana

Five new biphenyl glycosides, fortuneanosides A (1), B (2), C (3), D (4), and E (5), were isolated from the fruit of Pyracantha fortuneana. Their structures were established as 3,3'-dihydroxy-5'-methoxy-(1,1'-biphenyl)-4-O-beta-d-glucoside, 4'-hydroxy-2,3',5'-trimethoxy-(1,1'-biphenyl)-2'-O-beta-d-glucoside, 4'-hydroxy-3',5'-dimethoxy-(1,1'-biphenyl)-2-O-beta-d-glucoside, 2,4'-dihydroxy-3',5'-dimethoxy-(1,1'-biphenyl)-3-O-beta-d-glucoside, and 3,4'-dihydroxy-3',5'-dimethoxy-(1,1'-biphenyl)-4-O-beta-d-glucoside by spectroscopic analysis. All compounds were evaluated for inhibitory activity against tyrosinase. Compared with arbutin (IC(50) = 0.23 mM), fortuneanoside D possessed more potency, with an IC(50) value of 0.07 mM.     

New lanostanoids, elfvingic acids A-H, from the fruit body of Elfvingia applanata

Eight new lanostanoids, 12alpha,15beta-dihydroxy-3,7,11,23-tetraoxolanost-8,(20Z)(22)-dien-26-oic acid (1), 7beta,8beta-epoxy-15beta,20S-dihydroxy-3,12,23-trioxolanost-9(11),16-dien-26-oic acid (2), 7beta,8beta-epoxy-3beta,15beta,20S-trihydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (3), 7beta,8beta-epoxy-2alpha,3beta,15beta,20S-tetrahydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (4), 7beta,8beta-epoxy-3beta,15beta,20S,28-tetrahydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (5), 7beta,8beta-epoxy-3beta,15beta,19,20S-tetrahydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (6), 8beta,15beta,20S-trihydroxy-3,7,12,23-tetraoxolanost-9(11),16-dien-26-oic acid (7), 7alpha,8alpha-epoxy-15beta,23xi-dihydroxy-12-oxo-3,4-secolanost-4(28),9(11),(20Z)(22)-trien-3,26-dioic acid (8), and the methyl ester of 8 (8a) were isolated from the fruit bodies of Elfvingia applanata. Their structures were established primarily by NMR experiments, and their biological activity against Kato III and Ehlrich cells was investigated.     

Lanostane triterpenoids and triterpene glycosides from the fruit body of Fomitopsis pinicola and their inhibitory activity against COX-1 and COX-2

Two new lanostane triterpenoids (1, 2) and 10 new lanostane triterpene glycosides (3-12) have been isolated from the fruit bodies of Fomitopsis pinicola. Their structures were established primarily by NMR experiments and chemical methods, and their biological activity against COX-1 and COX-2 was investigated.     

New prenylhydroquinone glycosides from Phagnalon rupestre

Three new hydroquinone glycosides were isolated from the MeOH extract of the aerial parts of Phagnalon rupestre. Their structures were elucidated as 1-O-beta-glucopyranosyl-1,4-dihydroxy-2-(3',3'-dimethylallyl)benzene (1), 1-O-beta-glucopyranosyl-1,4-dihydroxy-2-(3'-hydroxymethyl-3'-methylallyl)benzene (2), and 1-O-(4' '-O-caffeoyl)-beta-glucopyranosyl-1,4-dihydroxy-2-(3',3'-dimethylallyl)benzene (3) by spectroscopic methods.     

New jujubogenin glycosides from Colubrina asiatica

Three new jujubogenin glycosides, namely, 3' '-O-acetylcolubrin (1); 3' ',2' "-O-diacetylcolubrin (2), and 3' '-O-acetyl-6' '-O-trans-crotonylcolubrin (3), were isolated from the leaves of Colubrina asiatica, in addition to the known colubrin, rutin, and kaempferol 3-O-rutinoside. Compounds 1-3 were isolated and purified via a combination of chromatographic procedures, and determined structurally using spectroscopic methods.     

New steroid glycosides from the starfish Asterias rathbuni

Two novel steroidal 24-O-xylosides, designated as rathbuniosides R(1) (1) and R(2) (2), and the known amurensoside A (3) and 3-O-sulfomarthasterone (4) have been isolated from the starfish Asterias rathbuni.The structures of all the compounds were determined from their spectroscopic data, including one- and two-dimensional NMR methods. The compounds 1 and 4 inhibit the cell division of fertilized sea urchin eggs at doses of 7.0 x 10(-5) and 2.9 x 10(-5) M, respectively.     

New triterpene glycosides from the stems of Anomospermum grandifolium

Two new dammarane saponins identified as jujubogenin 3-O-alpha-l-arabinofuranosyl(1-->2)-[beta-d-glucopyranosyl(1-->6) beta-d-glucopyranosyl(1-->3)]-alpha-l-arabinopyranoside (2) and jujubogenin 3-O-alpha-l-arabinofuranosyl(1-->2)-[6-O-[3-hydroxy-3-methylglutaryl]-beta-d-glucopyranosyl(1-->3)]-alpha-l-arabinopyranoside (3) and a new lupane saponin, 3beta-hydroxylup-20(29)-en-27,28-dioic acid 28-O-beta-d-glucopyranosyl(1-->2)-[beta-d-xylopyranosyl(1-->3)]-beta-d-xylopyranosyl(1-->2)-beta-d-glucopyranoside ester (5), along with the known jujubogenin 3-O-alpha-l-arabinofuranosyl(1-->2)-[beta-d-glucopyranosyl(1-->3)]-alpha-l-arabinopyranoside (1) and 3beta-hydroxylup-20(29)-ene-27,28-dioic acid (4), were isolated from the methanol extract of the stems of Anomospermum grandifolium. The structures of the new compounds were established by spectral analysis. Antimicrobial activity screening of compounds 1-3 revealed antifungal properties against C. albicans ATCC 3153 for compounds 2 and 3. The antibacterial and antifungal activities of the petroleum ether, chloroform, and methanol extracts of A. grandifolium stems were also evaluated.     

New steroidal glycosides from the fruits of Solanum anguivi

Four new steroidal saponins, anguiviosides III (1), XI (2), XV (3), and XVI (4), were isolated and characterized from the fruits of Solanum anguivi. Their structures were elucidated on the basis of spectroscopic analysis. The occurrence of the cholestane glycosides 3 and 4 is considered from a biogenetic point of view.     

New steroidal glycosides from the fruits of Tribulus terrestris

Three new steroidal saponins (1-3) were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic methods (IR, HRESIMS, 1D- and 2D-NMR) as 26-O-beta-D-glucopyranosyl-(25S)-5beta-furost-20(22)-en-3bet a, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl- (1-->4)]-beta-D-glucopyranoside (1), 26-O-beta-D-glucopyranosyl-(25S)-5beta-furost-20(22)-en-3bet a, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1 -->4)]-beta-D-galactopyranoside (2), and 25(S)-5beta-spirostan-3beta-ol-3-O-alpha-L-rhamnopyranosyl-( 1-->2)-[b eta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside (3). Compound 3 showed cytotoxicity against a human malignant melanoma cell line (SK-MEL).     

绒白乳菇子实体的化学成分研究

目的研究绒白乳菇Lactarius vellereus的化学成分。方法用Sephadex LH-20、LH-60,硅胶以及HPLC等色谱方法分离绒白乳菇的乙醇提取物,并根据化合物的光谱数据(UV、IR、MS、1H-NMR、13C-NMR)和X晶体衍射确定其结构。结果从绒白乳菇子实体中共分离得到11个化合物,分别为isolactarorufin(1)、3-O-ethyl-lactarolide A(2)、7α,8α,13-trihydroxy-marasm-5-oic acidγ-lactone(3)、velleratretraol(4)、leptosphaepin(5)、7α,8β,13-trihydroxy-marasm-5-oic acidγ-lactone(6)、lactarolide A(7)、D-阿洛醇(8)、bis(2-ethylhexyl)phthalate(9)、硬脂酸(10)、硬脂酸甲酯(11)。经光谱分析鉴定化合物1~4和6、7为倍半萜类化合物,化合物5为生物碱类化合物,化合物8~11为常见化合物。结论化合物1、2、4、5为首次从该菌中发现的化合物。化合物4拥有高度氧化的新型倍半萜骨架;化合物5为首次从陆生生物中分离得到的一种生物碱类化合物,对研究海洋生物和陆生生物之间的进化关系具有重要的意义。     

New pregnane glycosides from Sinomarsdenia incisa.

Five new pregnane glycosides, sinomarinosides A (1), B (2), C (3), D (4), and E (5), have been isolated from Sinomarsdenia incisa (Asclepiadaceae). The structures of these compounds were elucidated by NMR and mass spectroscopic methods and chemical evidence.     

New steroid glycosides from the deep-water starfish Mediaster murrayi

Four new 24-O-biosides of 5alpha-cholestane-3beta,6alpha,8,15beta, 24-pentaol, designated as mediasterosides M1 (1), M2 (2), M3 (3), and M4 (4), and the previously known 5alpha-cholestane-3beta,6beta,8, 15alpha,16beta,26-hexaol (5) have been isolated from the deep-water starfish Mediaster murrayi. Glycosides 1-3 contain rare carbohydrate moieties with (1-->5) bonds between the monosaccharide units. Compounds 1 and 2 showed the inhibition of cell division of fertilized sea urchin eggs and exhibited moderate hemolytic activities.     

New isoflavone and triterpene glycosides from soybeans

Chemical investigation of a soybean phytochemical concentrate resulted in the isolation and identification of two new isoflavanones, dihydrodaidzin (1) and dihydrogenistin (2), a new isoflavone, 2' ',6' '-O-diacetyloninin (3), and two new triterpenoid saponins (13 and 14). Nine known isoflavonoids (4-12) and three known saponins (15-17) were also identified. Structures of the new compounds were established by a combination of extensive NMR (DEPT, DQF-COSY, HMBC, HMQC, and ROESY) studies and chemical degradation. Cytotoxic activities (ED(50)) of various extracts and selected isoflavonoids and saponins were measured against human stomach carcinoma (Hs 740.T, Hs 756 T), breast adenocarcinoma (Hs 578 T, Hs 742.T), and prostate carcinoma (DU 145, LNCaP-FGC) cell lines. Isoflavonoids 3 and 5 were more active than 1 and 2 versus at least one of the three cell lines examined, indicating the importance of the 2,3-double bond in cytotoxicity. Saponins 13, 14, and 15 were slightly more active than saponins 16 and 17, indicating that sugar attachments at position-22 enhance cytotoxic activity.     

New dimeric macrolide glycosides from the marine sponge Myriastra clavosa

Clavosolides A-D (1-4), dimeric macrolides incorporating cyclopropyl, tetrahydropyranyl, and glycosidic ring systems, were isolated from the cytotoxic extract of a Philippines collection of the marine sponge Myriastra clavosa. The structures of the clavosolides, which occurred as only trace metabolites, were elucidated through extensive NMR spectroscopic analyses. Clavosolides A (1) and B (2) were recently reported metabolites from M. clavosa, while the unsymmetrical dimers clavosolides C (3) and D (4) had new structures.     

New xanthorin glycosides from a Dermocybe species.

A mixture of the 8-O-beta-D-glucopyranoside of omega-hydroxyxanthorin 1-O-methyl ether (3) and the 8-O-beta-D-gentiobioside of xanthorin 1-O-methyl ether (4) was isolated from the water-soluble extractives of the Australian toadstool Dermocybe sp. WAT 22963. Compounds 3 and 4 were identified by characterization of their respective peracetyl derivatives 5 and 6.     

New glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber

Four new diterpene glycosides, virescenosides R (1), S (2), T (3), and U (4), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures have been elucidated on the basis of HRFABMS, 1D and 2D NMR (1H, 13C, DEPT, COSY-45, COSY-RCT, HSQC, HMBC, and NOESY spectra), and the results of acidic hydrolysis as 19-O-[beta-D-glucopyranosyl(1-->6)-beta-d-altropyranosyl]-isopimara-7,15-diene-2alpha,3beta-diol (1), 19-O-beta-D-altropyranosyl-3-oxo-isopimara-8(14),15-diene-7alpha-ol (2), 19-O-beta-D-altropyranosyl-3,7-dioxo-isopimara-8,15-diene (3), and 19-O-beta-D-altropyranosyl-3,7-dioxo-isopimara-8(14),15-diene (4). The cytotoxic activity of the virescenosides was examined.     

New cytotoxic sterol glycosides from the octocoral Carijoa (Telesto) riisei

Two new steroidal glycosides, 3beta-O-(3'-O-acetyl-beta-D-arabinopyranosyl)-25xi-choles tan e-3beta, 5alpha,6beta,26-tetrol-26-acetate (riisein A, 2) and 3beta-O-(4'-O-acetyl-beta-D-arabinopyranosyl)-25xi-choles tan e-3beta, 5alpha,6beta,26-tetrol-26-acetate (riisein B, 3), were isolated from extracts of the Brazilian telestacean octocoral Carijoa (Telesto) riisei collected near Rio de Janeiro. The new glycosides co-occur with the polyhydroxy sterol, 25xi-cholestane-3beta,5alpha,6beta, 26-tetrol-26-acetate (1), an inseparable diastereomeric mixture previously reported from Telesto riisei collected in Micronesia. The structures of the new glycosides were assigned by spectroscopic methods and by comparison with spectral data for sterol 1. Riiseins A and B showed in vitro cytotoxicity toward HCT-116 human colon adenocarcinoma with IC(50) values of 2.0 microg/mL.     

New naphthopyranone glycosides from Paepalanthus vellozioides and Paepalanthus latipes.

Three new compounds-3, 4-dihydro-10-hydroxy-7-methoxy-3-(R)-methyl-1H-3,4-dihydronaphtho- ]2, 3c]-pyran-1-one-9-O-beta-D-glucopyranoside (1), 3, 4-dihydro-10-hydroxy-7-methoxy-3-(R)-methyl-1H-3,4-dihydronaphtho- [2, 3c]-pyran-1-one-9-O-beta-D-glucopyranosyl-(1-->6)-glucopyranoside (2), and 3,4-dihydro-10-dihydroxy-7-methoxy-3-(R)-methyl-1H-3, 4-dihydronaphtho-[2,3c]-pyran-1-one-9-O-beta-D-allopyranosyl (1-->6)glucopyranoside (3)-were isolated from the leaves of Paepalanthus vellozioides and Paepalanthus latipes and characterized by spectrometric methods, mainly electrospray mass spectrometry and 1D and 2D NMR experiments. These unusual glycosylated dihydronaphthopyranones may serve as taxonomic markers of the genus Paepalanthus, since these compounds were not detected in other genera belonging to the Eriocaulaceae family.     

New diterpene glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber

Three new diterpene glycosides, virescenosides O (1), P (2), and Q (3), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined on the basis of HRMALDIMS and NMR data as beta-D-altropyranosido-19-isopimara-8(14),15-diene-7alpha,3beta-diol (1), beta-D-altropyranosido-19-7-oxoisopimara-8(9),15-diene-3beta-ol (2), and beta-D-mannopyranosido-19-isopimara-7,15-diene-3beta-ol (3). The cytotoxic activity of the virescenosides was examined.     

New 3,4-seco-lupane-type triterpene glycosides from Acanthopanax senticosus forma inermis

Four new 3,4-seco-lupane-type triterpene glycosides (1-4) were isolated from the leaves of Acanthopanax senticosus forma inermis. The structures of 1-4 were established as 11alpha-hydroxy-3, 4-seco-lup-4(23),20(30)-dien-3-oic acid methyl ester 28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-be ta-D-glucopyranoside, designated as inermoside (1); 1-deoxychiisanoside (2); 24-hydroxychiisanoside (3); and 11-deoxyisochiisanoside (4) by (1)H-(1)H COSY and (1)H-(13)C COSY(HMBC, HMQC) methods and FABMS.