A new flavonol glycoside from Hydrangea macrophylla (Thunb.) Seringe

<正>A new kaempferol glycoside,named kaempferol 3-O-[6″-O-β-D-glucopyranosyl-6′′′-O-α-L-rhamnopy ranosyl-2′′′′-O-α-L-rhamnopyranosyl]-β-D-glucopyranoside,was isolated from Hydrangea macrophylla(Thunb.) Seringe.Its structure was establishedby spectroscopic techniques including MS,IR,UV,and 2D NMR.     

Cucumarioside G4 — A new triterpenglycoside from the holothurian Eupentacta fraudatrix

A minor glycoside — cucumarioside G₄ (I) — has been isolated from the total triterpeneglycosides of the holothurianEupentacta fraudatrix, and its structure has been determined by physical and chemical methods as 16β-acetoxyholosta-7,23E-diene-3β, 25-diol 3-O-(3-O-methyl-β-D-xylopyranosyl)-(1→3)-O-β-D-glucopyranosyl-(1→4)-O-β-D-quinovopyransoyl-(1→2)-(4-O-(sodium sulfato)-β-D-xylopyranoside)].     

Flavonoids of the epigeal part ofRhodiola rosea. II. Structures of new glycosides of herbacetin and of gossypetin

The structure of four new flavonol glycosides isolated from the epigeal part ofRhodiola rosea have been established: 7-O-α-L-rhamnopyranosylgossypetin (rhodiolgin), 8-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranosylgossypetin (rhodiolgidin), 8-O-β-D-glucopyranosol-7-O-α-L-rhamnopyranosylherbacetin (rhodionidin), and 3-O-β-D-glucopyranosyl-8-O-β-D-xylopyranosylherbacetin (rhodalidin). The properties of the previously undescribed incomplete methyl ethers of herbacetin and gossypetin obtained during the structural analysis of the glycosides have been studied. It has been found that diazomethane methylates the 5-OH groups in the diglycosides investigated.     

Two New Flavonol Glycosides from Knoxia corymbosa

Two new flavonol glycosides (1 and 2) together with two known flavonoides (3 and 4),were isolated from the whole plant of Knoxia corymbosa willd. The structures of I and 2 were elucidated as kaempferol-7-O-α-L-arabinosyl-3-O-β-D-6“-acetylglucopyranoside and kaempferol -7-O-α-L-arabinosyl-3-O-β-D-3″,6″-diacetylglucopyranoside respectivedly.     

九子参中三个糖链上带乙酰基的新三萜皂苷-九子参苷B,C, D

从石竹科植物九子参(Silene rubicunda)根中得到四个糖链上带乙酰基的新的三萜皂苷-九子参苷A, B, C, D(rubicunosides A~D, 1~4)。前文已详细报道了九子参苷A的结构研究, 本文报道九子参苷B, C, D的结构。通过FAB-MS和NMR,分别确定九子参苷B, C, D为糖链上带单乙酰基的三萜九糖苷、七糖苷和糖链上带双乙酰基的三萜八糖苷, 分别命名为皂树酸-3-O-β-D-吡喃半乳糖-(1→2)-[β-D-吡喃木糖-(1→3)]-β-D-吡喃葡萄糖醛酸-28-O-β-D-吡喃木糖-(1→3)-β-D-吡喃木糖-(1→4)-α-L-吡喃鼠李糖-(1→4)-[β-D-吡喃葡萄糖-(1→4')-β-D-吡喃鸡纳糖-(1→2)]-[3'-O-乙酰基]-β-D-吡喃夫糖苷(九子参苷B, 2), 皂树酸-3-O-β-D-吡喃半乳糖-(1→2)-[β-D-吡喃木糖-(1→3)]-β-D-吡喃萄淘糖醛酸-28-O-β-D-吡喃木糖-(1→4)-α-L-吡喃鼠李糖-(1→4)-[4"-O-乙酰基-β-D-吡喃葡萄糖-(1→2)]-β-D-吡喃夫糖苷(九子参苷C, 3), 皂树酸-3-O-β-D－吡喃半乳糖-(1→2)-[β-D-吡喃半乳糖-(1→2)-[β-D-吡喃木糖-(1→3)]-[6'-O-正丁基]-β-D-吡喃葡萄糖醛酸-28-O-β-D-吡喃木糖-(1→3)-β-D-吡喃木糖-(1→4)-α-L-吡喃鼠李糖-(1→4)-[2"-O-乙酰基-β-D-吡喃鸡纳糖-(3'-O-乙酰基]-β-D-吡喃夫糖苷(九子参苷D, 4)。     

Triterpene glycosides of Astragalus and their genins XLIV. Structure of cyclocarposides A and C

The structures of two new cycloartane glycosides — cyclocarposides A and C, isolated from the herbAstragalus coluteocarpus Boiss. — have been established on the basis of spectral characteristics and chemical transformations. Cyclocarposides A and C are: 204R,24S-epoxycycloartane-3β,6α,17β,25-tetraol 3-O-(2-O-acetyl-β-D-xylopyranoside)6-O-(2-O-acetyl-α-L-rhamnopyranoside) and 20R,24S-epoxycyloartane-3β,6α,16β,25-tetraol 3-O-(2-O-acetyl-β-D-xylopyranoside) 6-O-α-L-rhamnopyranoside, respectively.     

Steroids of the spirostan and furostan series from Nolina microcarpa I. Structures of nolinospiroside C and nolinofurosides A and C

In addition to the know steroid sapogenin (25S)-ruscogenin (I), three new glycosides have been isolated from the leaves ofNolina microcarpa S. Wats. (family Dracaenacea), and the following structures are suggested for them: (25S)-spirost-5-ene-1β,3β-diol 1-O-β-D-fucopyranoside (nolinospiroside C, II), (25S)-furost-5-ene-1β,3β,22α,26-tetraol 1-O-β-D-fucopyranoside (nolinofuroside A, III), and (25S)-furost-5-ene-1β, 3β, 22α, 26-tetraol 1-O-β-D-fucopyranoside 26-O-β-D-glucopyranoside (nolinofuroside C, V).     

Triterpene glycosides of alfalfa. IV. Medicoside J

A new triterpene glycoside has been isolated from the roots ofMedicago sativa L. (family Fabaceae) — medicoside J, and its structure has been established as a medicagenic acid 3-O-β-D-glucopyranoside 28-O-[O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranoside].     

Ultra-performance LC-photodiode array-eλ-ESI-MS/MS screening method for the detection of radical-scavenging natural antioxidants from radix et rhizoma Rhei

A novel ultra-performance LC-photodiode array-el-ESI-MS/MS screening method was developed for the detection and identification of natural antioxidants from radix et rhizoma Rhei. Nine compounds were found to possess a potential antioxidant activity, and their free radical-scavenging capacities were investigated in detail. The nine compounds were identified as 1-O-galloyl-2-O-cinnamoylglucose, 6-hydroxymusizin-8-O-β-D-glucopyranoside, (+)-catechin, gallic acid 3-O-β-D-glucopyranoside, trans-3,5,4'-trihydroxystilbene- 4'-O-β-D-(2"-O-galloyl)-glucopyranoside, sennoside A, 4-(4'-hydroxyphenyl)-2- butanone-4'-O-β-D-(2"-O-galloyl-6"-O-p-coumaroyl) glucopyranoside, emodin-8-O-(6'-Omalonyl) glucopyranoside, and physcion-8-O-β-D-glucopyranoside. The reactivity and SC(50) values of those compounds were investigated, respectively. 1-O-Galloyl-2-O-cinnamoylglucose showed the strongest capability for scavenging 1,1-diphenyl-2-picrylhydrazylfree radical; trans-3,5,4'-trihydroxystilbene-4'-O-β-D-(2"-O-galloyl) glucopyranoside showed the strongest capability for scavenging superoxide radical; 4-(4'-hydroxyphenyl)-2-butanone- 4'-O-2-D-(2"-O-galloyl-6"-O-p-coumaroyl) glucopyranoside exhibited the highest reactivity in the lipid peroxidation processes. The use of the analytical screening method based on ultra-performance LC-photodiode array-el-ESI-MS/MS would provide a new way for rapid detection of radical-scavenging natural compounds from radix et rhizoma Rhei or complex matrices.     

Glycosylation of vanillin and 8-nordihydrocapsaicin by cultured Eucalyptus perriniana cells

Glycosylation of vanilloids such as vanillin and 8-nordihydrocapsaicin by cultured plant cells of Eucalyptus perriniana was studied. Vanillin was converted into vanillin 4-O-β-D-glucopyranoside, vanillyl alcohol, and 4-O-β-D-glucopyranosylvanillyl alcohol by E. perriniana cells. Incubation of cultured E. perriniana cells with 8-nordihydrocapsaicin gave 8-nordihydrocapsaicin 4-O-β-D-glucopyranoside and 8-nordihydrocapsaicin 4-O-β-D-gentiobioside.     

Structural determination of two new triterpenoid saponins acylated with monoterpenic acid from Gymnocladus chinensis Baill

Two new triterpenoid saponins acylated with monoterpenic acid, 2β,23-dihydroxy-3-O-α-L-rhamnopyranosyl-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[3-O-(β-D-glucopyranosyl)-4-O-(2-methylbutanoyl)-β-L-arabinopyranosyl]-2,7-octadienoyl)-acacic acid 28-O-β-D-xylopyranosyl-(1?→?3)-β-D-xylopyranosyl-(1?→?4)-[β-D-glucopyranosyl-(1?→?3)]-α-L-rhamnopyranosyl-(1?→?2)-[α-L-rhamnopyranosyl-(1?→?6)]-β-D-glucopyranosyl ester and 2β,23-dihydroxy-3-O-α-L-rhamnopyranosyl-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[4-O-((6S)-2-trans-2,6-dimethyl-6-O-(β-L-arabinopyranosyl)-2,7-octadienoyl)]-β-L-arabinopyranosyl]-2,7-octadienoyl}-acacic acid 28-O-β-D-xylopyranosyl-(1?→?3)-β-D-xylopyranosyl-(1?→?4)-[β-D-glucopyranosyl-(1?→?3)]-α-L-rhamnopyranosyl-(1?→?2)-[α-L-rhamnopyranosyl-(1?→?6)]-β-D-glucopyranosyl ester were isolated from the fruit of Gymnocladus chinensis Baill. and the structural elucidation of both the compounds was accomplished by extensive studies of their spectroscopic (1D and 2D NMR, TOF-MS, QFT-MS) and chemical methods.     

Cardiac glycosides of Erysimum contractum. II

The structure of a new cardiac glycoside isolated from the seeds ofErysimum contractum has been established. The glycoside, which has been called nigrescigenin digilanidobioside is 3β,5,11α,14-tetrahydroxy-19-oxo-5β,14β-card-20(22)-enolide 3-O-(4-O-β-D-glucopyranosyl-β-D-digitoxopyranoside).     

A new flavonol glycoside from the seeds of Nigella glandulifera

A new flavonol glycoside, kaempferol 3-O-α-L-rhamnopyranosyl (1?→?6)-O-[β-D-glucopyranosyl (1?→?2)-O-β-D-galactopyranosyl (1→2)]-O-β-D-glucopyranoside (1), together with a known compound, kaempferol 3-O-β-D-glucopyranosyl (1?→?2)-O-β-D-galactopyranosyl (1?→?2)-O-β-D-glucopyranoside (2) was isolated from the seeds of Nigella glandulifera. Their structures were elucidated on the basis of spectral analysis, including ESI-MS, ESI-MS/MS, HR-ESI-MS, DQF-COSY, TOCSY, HSQC and HMBC techniques.     

木犀草素-7-O-β-D-葡萄糖苷在几种分子聚集体系中的增溶行为研究

木犀草素-7-O-β-D-葡萄糖苷是活性较高的一种天然黄酮化合物, 由于其本身的低水溶性使其应用受到限制. 制备了三种微乳体系, 用HPLC法研究了木犀草素-7-O-β-D-葡萄糖苷在这三种微乳体系及CTAB和吐温80胶束中的溶解能力; 并用紫外光谱法和核磁共振波谱法分析了木犀草素糖苷与十六烷基三甲基溴化铵(CTAB)和吐温80的作用机制. 研究表明: 五种分子聚集体系对木犀草素糖苷有明显的增溶效果; 木犀草素糖苷可能与CTAB、吐温80形成了缔合物, 缔合平衡常数分别为2326 L/mol和362 L/mol, 其增溶位点分别是CTAB胶束的亲水外层和吐温80胶束的栅栏层.     

Structure of pseudostichoposide A — The main triterpene glycoside from the holothurian Pseudostichopus trachus

A holostane oligoglycoside — pseudostichoposide A — has been isolated from the holothurianPseudostichopus trachus Sluiter, collected on the oceanic side of the island of Urup (Kurile Islands). Its structure has been established with the aid of¹³C and¹H NMR spectroscopy and partial acid hydrolysis with sulfuric acid in the presence of butanol as 3β-{O-(3-O-methyl-β-D-quinovopyransoyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-β-D-quinovopyranosyl-(1 → 2)-[4-O-(sodium sulfato)-β-D-xylopyranosyloxy]}-holost-7-en-22-one. Its native genin, which has been called urupogenin (3β-hydroxyholost-7-en-22-one) was obtained on partial hydrolysis in the form of an individual compound. It is a new holostane derivative.     

Triterpene glycosides of Astragalus and their genins. XXIV. Cycloorbicoside G from Astragalus orbiculatus

A bisdesmosidic glycoside — cycloorbicoside G — has been isolated from the epigeal parts of the plantAstragalus orbiculatus Ledeb. (Leguminosae), and on the basis of chemical transformations and spectral characteristics its structure has been established as (23R,24S)-16β,23;16α,24-diepoxycycloartane-3β,7β,25-triol 25-O-β-D-glucopyranoside 3-O-β-D-xylopyranoside.     

狗枣猕猴桃叶化学成分研究(Ⅱ)

从狗枣猕猴桃叶中分离出4个新的黄酮类化合物, 经1D NMR, 2D NMR及ESI-MS等波谱分析鉴定了其结构, 分别是4'-甲氧基-槲皮素-7-O-(4"-O-乙酰基-鼠李糖基)-3-O-β-D-吡喃葡萄糖苷(1), 山柰甲黄素-7-O-(3"-O-乙酰基-鼠李糖基)-3-O-芸香糖苷(2), 山柰酚-7-O-(4"-O-乙酰基-鼠李糖基)-3-O-芸香糖苷(3)和4'-甲氧基-槲皮素-7-O-(4"-O-乙酰基-鼠李糖基)-3-O-芸香糖苷(4).     

Two new triterpenoid saponins from Rhaponticum uniflorum

Two new triterpenoid saponins were isolated from the roots of Rhaponticum uniflorum.Their structures were elucidated as 3-O-[β-D-glucopyranosyl] -ilexolic acid-28-O-[β-D-glucopyranosyl]ester 1 and 3-O-[β-D-glucopyranosyl]-urs-12,19(29)-dien-oic acid-28-O-[β-D-glucopyranosyl]ester 2 mainly by 1D,2D NMR techniques and chemical methods.     

Steroid saponins and sapogenins ofAllium. XVI. Turoside C fromAllium turcomanicum

From a methanolic extract of the bulbs ofAllium turcomanicum Rgl. we have isolated a new furostanol glycoside, turoside C (I). An acid hydrolysate was found to contain the aglycone — neoagigenin (II) — and the sugars D-xylose, D-glucose, and D-galactose in a ratio of 1:4:1. The structure of the furostanol (I) has been established by methylation, enzymatic hydrolysis, and oxidative cleavage, and also by the oxidative cleavage of (II), as (25S)-5α-furostan-2α,3β,6β,22α,26-pentaol 26-O-β-D-glucopyranoside 3-O-{[O-β-D-xylopyranosyl-(1→3)]-[O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)]-O-β-D-glucopyranosyl-(1→4)-β-D-galacto-pyranoside}.     

Triterpene glycosides of Hedera taurica X. Structures of compounds F4, I,and J from the leaves of Crimean ivy

Echinocystic acid 3-sulfate and new 3-sulfates — of the 28-O-[O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl esters of oleanolic and echinocystic acids have been isolated from the leaves of Crimean ivyHedera taurica Carr. (fam. Araliaceae).