Isoflavone diglycosides from Glycosmis pentaphylla

Six new apiosyl-(1-->6)-glucosyl isoflavones (1-6) and four known ones were isolated from the stems of Glycosmis pentaphylla. The structures of the new glycosides are 3',7-dihydroxy-4',5,6-trimethoxyisoflavone 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1), 2',7-dihydroxy-4',5',5,6-tetramethoxyisoflavone 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), 2',7-dihydroxy-4',5',5,6-tetramethoxyisoflavone 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3), 7-hydroxy-4',8-dimethoxyisoflavone 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (4), 7-hydroxy-4',6-dimethoxyisoflavone 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (5), and 4',5-dihydroxy-3',7-dimethoxyisoflavone 4'-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (6). Their structures were established primarily by NMR experiments and chemical methods.     

Phenolic glycosides from berries of Pimenta dioica

Four new phenolic glycosides, (2-hydroxy-3-methoxy-5-allyl)phenyl beta- d-(6-O-E-sinapoyl)glucopyranoside (1), (1' R,5' R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3 Z-pentenyl beta-D-(6-O-galloyl)glucopyranoside (2), (S)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (3), and (R)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (4), were isolated from the berries of Pimenta dioica together with eight known flavonoids. The structures of 1-4 were elucidated on the basis of MS and NMR data and enzymatic hydrolysis. All four glycosides showed radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals.     

Bioactive constituents from Boswellia papyrifera

Phytochemical investigation of the stem bark extract of Boswellia papyrifera afforded two new stilbene glycosides, trans-4',5-dihydroxy-3-methoxystilbene-5-O-{alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside (1), trans-4',5-dihydroxy-3-methoxystilbene-5-O-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside (2), and a new triterpene, 3alpha-acetoxy-27-hydroxylup-20(29)-en-24-oic acid (3), along with five known compounds, 11-keto-beta-boswellic acid (4), beta-elemonic acid (7), 3alpha-acetoxy-11-keto-beta-boswellic acid (8), beta-boswellic acid (9), and beta-sitosterol (10). The stilbene glycosides exhibited significant inhibition of phosphodiesterase I and xanthine oxidase. The triterpenes (3-9) exhibited prolyl endopeptidase inhibitory activities.     

Saponarioside C, the first alpha-D-galactose containing triterpenoid saponin, and five related compounds from Saponaria officinalis

Six novel triterpenoid saponins, named saponariosides C-H, were isolated from the whole plants of Saponaria officinalis. Their structures were established as saponarioside C (1), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-alpha-D-galactopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-- >6)-[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside D (2), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside E (3), 3-O-beta-D-glucopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside F (4), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside G (5), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1-->3 )]-beta-D-glucopyranoside; and saponarioside H (6), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranoside, by a combination of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC, and NOESY) studies and chemical degradation.     

卷丹化学成分研究

目的：研究卷丹Lilium lancifolium鳞茎中的化学成分。方法：用色谱法分离卷丹的化学成分,用波谱法鉴定其结构。结果：从卷丹中分离并鉴定了10个化合物,分别为王百合苷A(1),王百合苷C(2),甲基-α-D-吡喃甘露糖苷(3),甲基-α-D-吡喃葡萄糖苷(4),(25R,26R)-26-甲氧基螺甾烷-5-烯-3β-O-α-L-吡喃鼠李糖-(1→2)-［β-D-吡喃葡萄糖-(1→6)］-β-D-吡喃葡萄糖苷(5),(25R)-螺甾烷-5-烯-3β-O-α-L-吡喃鼠李糖-(1→2)-［β-D-吡喃葡萄糖-(1→6)］-β-D-吡喃葡萄糖苷(6),(25R,26R)-17α-羟基-26-甲氧基螺甾烷-5-烯-3β-O-α-L-吡喃鼠李糖-(1→2)-［β-D-吡喃葡萄糖-(1→6)］-β-D-吡喃葡萄糖苷(7),胡萝卜苷(8),腺嘌呤核苷(9),小檗碱(10)。结论：除化合物1,3外均为首次从该植物中分离得到,其中10为首次从百合属植物中发现。     

Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea

Three 20(S)-protopanaxatriol-type saponins, ginsenoside-Rg1 (1), notoginsenoside-R1 (2), and ginsenoside-Re (3), were transformed by the fungus Absidia coerulea (AS 3.3389). Compound 1 was converted into five metabolites, ginsenoside-Rh4 (4), 3beta,2beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-beta-D-glucopyranoside (5), 20(S)-ginsenoside-Rh1 (6), 20(R)-ginsenoside-Rh1 (7), and a mixture of 25-hydroxy-20(S)-ginsenoside-Rh1 and its C-20(R) epimer (8). Compound 2 was converted into 10 metabolites, 20(S)-notoginsenoside-R2 (9), 20(R)-notoginsenoside-R2 (10), 3beta,12beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (11), 3beta,12beta-dihydroxydammar-(E)-20(22),24-diene-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (12), 3beta,12beta,20,25-tetrahydroxydammaran-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (13), and compounds 4-8. Compound 3 was metabolized to 20(S)-ginsenoside-Rg2 (14), 20(R)-ginsenoside-Rg2 (15), 3beta,12beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (16), 3beta,12beta-dihydroxydammar-(E)-20(22),24-diene-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (17), 3beta,12beta,20,25-tetrahydroxydammaran-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (18), and compounds 4-8. The structures of five new metabolites, 10-13 and 16, were established by spectroscopic methods.     

Five phenolic glycosides from Alangium chinense

From the dried leaves of Alangium chinense, five novel phenolic glycosides, 6'-O-galloylsalicin (1); 4',6'-di-O-galloylsalicin (2); 4',6'-O-(S)-hexahydroxydiphenoylsalicin (3); 4', 6'-O-(R)-hexahydroxydiphenoylsalicin (4); and pyrocatechol 1-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranoside (5) were isolated. The structures of these new compounds were determined by spectroscopic methods.     

Four new isoflavone triglycosides from Sophora japonica

Four new isoflavone triglycosides, genistein 7-O-beta-D-glucopyranoside-4'-O-[(alpha-L-rhamnopyranosyl)-(1-->2)-beta-D-glucopyranoside] (1), genistein 7-O-beta-D-glucopyranoside-4'-O-[(beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside] (2), genistein 7-O-alpha-L-rhamnopyranoside-4'-O-[(alpha-L-rhamnopyranosyl)-(1-->2)-beta-D-glucopyranoside] (3), and genistein 7-O-alpha-L-rhamnopyranoside-4'-O-[(beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside] (4), together with nine known compounds, namely, genistein 7-O-beta-D-glucopyranoside-4'-O-beta-D-glucopyranoside, sophorabioside, prunetin 4'-O-beta-D-glucopyranoside, sophororicoside, genistin, rutin, kaempferol 3-O-beta-rutinoside, quercetin 3-O-beta-D-glucopyranoside, and kaempferol 3-O-beta-D-glucopyranoside, were isolated from the pericarps of Sophora japonica. The structures of 1-4 were determined by spectroscopic methods.     

轮叶棘豆的化学成分研究

目的：研究轮叶棘豆的化学成分。方法：90%乙醇冷浸提取,所得浸膏经硅胶,聚酰胺,C-18,Sephadex LH-20等多种材料进行柱色谱分离,通过波谱学方法鉴定化合物的结构。结果：分离鉴定了8个化合物,分别鉴定为azukisapogenol(1),(22E,24R)-24-甲基-5α-胆甾-7,22-二烯-3β,5α,6β-三醇(2),芹菜素(3),3′,4′-二甲氧基-槲皮素-3-O-β-D-半乳糖吡喃苷 (4),7,4′- 二甲氧基-槲皮素-3-O-α-L-鼠李糖吡喃基(1→2)-β-D-葡萄糖吡喃苷(5),(2S,3S,4R)-N-［(R)-2′-羟基二十四烷醇基］-1,3,4-三羟基-2-氨基-十八-6-烯(6),β-谷甾醇(7),胡萝卜苷(8)。结论：所有化合物均为首次从该植物中分得。     

Acetylated flavonoid glycosides potentiating NGF action from Scoparia dulcis

Three new acetylated flavonoid glycosides, 5,6,4'-trihydroxyflavone 7-O-alpha-L-2,3-di-O-acetylrhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (1), apigenin 7-O-alpha-L-3-O-acetylrhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (2), and apigenin 7-O-alpha-L-2,3-di-O-acetylrhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (3), were isolated from Scoparia dulcis together with the known compound eugenyl beta-D-glucopyranoside (4). Their structures were elucidated by spectroscopic analyses. Compounds 2 and 3 showed an enhancing activity of nerve growth factor-mediated neurite outgrowth in PC12D cells.     

Inhibitors of osteoclast differentiation from Cephalotaxus koreana

Three new flavonoid glycosides ( 1- 3), 11-hydroxyhainanolidol ( 4), and a new dibenzylbutyrolactone lignan glycoside ( 5) were isolated from the aerial parts of Cephalotaxus koreana Nakai, along with 19 known flavonoids. The structures of the new compounds were elucidated using spectroscopic evidence, primarily NMR and MS. Twenty-four compounds were isolated, and among these isoscutellarein 5-O-beta-D-glucopyranoside ( 3), apigenin ( 6), kaempferol 3-O-alpha-L-rhamnopyranosyl(1'-->6')-beta-D-glucopyranoside ( 7), tamarixetin 3-O-alpha-L-rhamnopyranosyl(1'-->6')-beta-D-glucopyranoside ( 8), quercetin 3-O-[6'-O-acetyl]-beta-D-glucopyranoside ( 9), and quercetin 3-O-alpha-L-rhamnopyranoside ( 10) showed significant inhibitory activities against osteoclast differentiation at concentrations of 0.1 and 1.0 microg/mL.     

Polyhydroxylated spirostanol saponins from the tubers of Dioscorea polygonoides

Three new polyhydroxylated spirostanol saponins (1-3) were isolated from the tubers of Dioscorea polygonoides. The structures of these new compounds were determined on the basis of extensive spectroscopic analysis and the results of acid or enzymatic hydrolysis as (23S,24R,25S)-23,24-dihydroxyspirost-5-en-3beta-yl O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (1), (23S,25R)-12alpha,17alpha,23-trihydroxyspirost-5-en-3beta-yl O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (2), and (23S,25R)-14alpha,17alpha,23-trihydroxyspirost-5-en-3beta-yl O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (3), respectively.     

Phenolic constituents and antioxidant activity of an extract of Anthuriumversicolor leaves

Fractionation of a methanolic extract of the leaves of Anthurium versicolor has resulted in the isolation of two main fractions, I and II. Both the extract and the fractions were assayed for their radical-scavenging activity by means of an in vitro test (bleaching of the stable 1,1-diphenyl-2-picrylhydrazyl radical) and showed a significant radical-scavenging effect. Subsequent chromatographic fractionation of the most active fraction, II, has led to the isolation and characterization, as major constituents, of four new flavone glycosides, acacetin 6-C-[alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranoside] (1), acacetin 6-C-[beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside] (2), acacetin 6-C-[beta-D-apiofuranosyl-(1-->3)-beta-D-glucopyranoside] (3), and acacetin 8-C-[alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranoside] (4), as well as vitexin (apigenin-8-C-beta-D-glucopyranoside) and rosmarinic acid. The structures of 1-4 were determined using spectroscopic methods.     

Cytotoxic steroidal saponins from the rhizomes of Asparagus oligoclonos

Two new steroidal saponins, aspaoligonins A (2) and B (3), were isolated from the methanolic extract of the rhizomes of Asparagus oligoclonos together with a known spirostanol saponin, asparanin A (1). Aspaoligonins A and B were characterized as (25S*)-5beta-spirostan-3beta,17alpha-diol 3-O-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranoside and (25S*)-5beta-spirostan-3beta,17alpha-diol 3-O-alpha-L-rhamnopyanosyl (1-->4)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-glucopyranoside, respectively, by spectrometric analyses including HRFABMS and 2D NMR. Compounds 1-3 were cytotoxic against five human tumor cell lines with IC50 values of 2.05-2.84 microg/mL.     

Chionaeosides A-D, triterpene saponins from Paronychia chionaea

Four new triterpenoid saponins, chionaeosides A-D (1-4) were isolated from the roots of Paronychia chionaea. On the basis of their spectroscopic data, the structures of the new saponins were established as 3-O-alpha-L-arabinopyranosylgypsogenic acid 28-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1), 3-O-alpha-L-arabinopyranosylgypsogenic acid 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (2), 3-O-alpha-L-arabinopyranosylgypsogenic acid 28-O-beta-D-glucopyranoside (3), and 3-O-alpha-L-arabinopyranosylgypsogenic acid (4).     

Naphthopyranone glycosides from Paepalanthus microphyllus

Three new naphthopyranone glycosides, paepalantine-9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1), paepalantine-9-O-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranoside (2), and paepalantine-9-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (3), along with the known paepalantine-9-O-beta-D-glucopyranoside (4) were isolated from aerial parts of Paepalanthus microphyllus. These compounds were characterized by spectrometric methods, including electrospray mass spectrometry and 1D and 2D NMR experiments. As a part of our program for screening natural compounds for anti-HIV activity, compounds 1-4 were tested in C8166 cells infected with HIV-1MN.     

藏药五脉绿绒蒿中非生物碱成分

目的:研究藏药五脉绿绒蒿Meconopsis quintuplinervia的化学成分。方法:应用色谱技术分离纯化,用波谱学方法确定化合物结构。结果:从乙醇提取物中分离得到12个化合物,分别鉴定为:槲皮素-3-O-β-D-葡萄糖苷(Ⅰ),槲皮素-3-O-[β-D-半乳糖(1→6)]-β-D-葡萄糖苷(Ⅱ),山柰素-3-O-[β-D-葡萄糖(1→2)]-β-D-葡萄糖苷(Ⅲ),异鼠李黄素-3-O-[β-D-半乳糖苷(1→6)]-β-D-葡萄糖(Ⅳ),咖啡酸(Ⅴ),原儿茶酸(Ⅵ),对羟基肉桂酸(Ⅶ),2-(3,4-二羟苯基)-乙醇β-D-吡喃葡萄糖苷(Ⅷ),对羟基苯甲酸β-D-吡喃葡萄糖酯苷(Ⅸ),肉桂酸4-O-β-D-吡喃葡萄糖苷(Ⅹ),5,7-二羟基色原酮(Ⅺ),胡萝卜苷(Ⅻ)。结论:除Ⅵ和Ⅻ外,其余10个化合物均为首次从该属植物中发现。     

Phenylethanoid glycosides from Globularia trichosantha.

Five phenylethanoid glycosides, crenatoside (= oraposide) (1), verbascoside (= acteoside) (2), trichosanthoside A (3), rossicaside A (4), and trichosanthoside B (5), were isolated from the aerial parts of Globularia trichosantha. Compounds 3 and 5 are new natural compounds, and their structures were established as 3, 4-dihydroxy-beta-phenylethoxy-O-beta-D-xylopyranosyl-(1-->4)-alpha -L- rhamnopyranosyl-(1-->3)-4-O-caffeoyl-beta-D-glucopyranoside and 3, 4-dihydroxy-beta-phenylethoxy-O-[beta-D-xylopyranosyl-(1-->4)-alph a-L -rhamnopyranosyl-(1-->3)]-[beta-D-xylopyranosyl-(1-->6)]-4-O-caffeoyl -beta-D-glucopyranoside, respectively. The structures of all compounds were established by spectral evidence. Compounds 1-5 also demonstrated scavenging properties toward the 2, 2-diphenyl-1-picrylhydrazyl radical in TLC autographic assays.     

Three new acylated triterpene saponins from Acanthophyllum squarrosum

Three new triterpenoid saponins, 1-3, were isolated from the roots of Acanthophyllum squarrosum. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-3-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-3,4-di-O-acetyl-beta-D-fucopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[5-O-acetyl-alpha-L-arabinofuranosyl-(1-->3)]-4-O-acetyl-beta-D-fucopyranoside (2), and 3-O-beta-D-glucopyranosyl-quillaic acid-28-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (3).     

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).