A new triterpenoidal saponin from Acacia auriculiformis.

A new triterpenoidal saponin has been isolated from an aqueous EtOH extract of the legumes of Acacia auriculiformis and characterized as 3-O-([beta-D-xylopyranosyl(1----3)-beta-D-xylopyranosyl(1----4)-alpha-L- rhamnopyranosyl(1----2)]-[alpha-L-rhamnopyranosyl(1----4)]-beta-D- glucopyranosyl)-3,16,21-trihydroxyolean-12-en-28-oic acid [1] by chemical studies and spectral data.     

Oleanane and taraxerane glycosides from the roots of Gomphrena macrocephala

Phytochemical screening of the roots of Gomphrena macrocephala, with particular attention to its triterpene glycoside constituents, has resulted in the isolation of two new oleanane glycosides (1 and 2) and a new taraxerane glycoside (3). The structures of 1-3 were determined as 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]olean-28,13-olide (1), 11alpha,12alpha-epoxy-3beta-[(O-beta-D-galactopyranosyl-(1-->3)-O-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl)-oxy]olean-28,13-olide (2), and 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]taraxer-14-en-28-oic acid beta-D-glucopyranosyl ester (3), respectively, on the basis of their spectroscopic data and the results of hydrolysis. The aglycones (1a and 3a) of 1-3 with an epoxy group showed cytotoxic activity against HSC-2 human oral squamous carcinoma cells.     

Oleanane saponins in "kancolla", a sweet variety of Chenopodium quinoa

Seven triterpenoid saponins were isolated from the seeds of "kancolla", a sweet variety of Chenopodium quinoa. Their structures were phytolaccagenic acid 3-O-[alpha-L-arabinopyranosyl-(1' '-->3')-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside, oleanolic acid 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside, hederagenin 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside, phytolaccagenic acid 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside, oleanolic acid 3-O-[beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside, oleanolic acid 3-O-[alpha-L-arabinopyranosyl-(1'-->3')-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside, and the new compound serjanic acid 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside (1). The structure of 1 was characterized on the basis of spectroscopic and chemical evidence.     

Triterpenoid saponins from the roots of Pulsatilla koreana

Six new saponins, five lupanes (1-5) and one oleanane (6), along with 11 known saponins, were isolated from the roots of Pulsatilla koreana. The structures of the new saponins were found to be 23-hydroxy-3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (1), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (2), 3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (3), 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (4), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->4)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (5), and hederagenin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (6). Their structures were determined on the basis of 1D and 2D NMR ((13)C NMR, (1)H NMR, (1)H-(1)H COSY, HMQC, and HMBC) methods, FABMS, and hydrolysis. All isolated compounds were evaluated for their cytotoxic activity against A-549 human lung carcinoma cells.     

Yemuoside I, a new nortriterpenoid glycoside from Stauntonia chinensis.

A new nortriterpenoid glycoside, named yemuoside [I] was isolated from Stauntonia chinensis. On the basis of chemical and spectral evidence, it structure was determined as 3-O-[alpha-L-arabinopyranosyl-(1----3)-alpha-L-rhamnopyranosyl-(1- ---2)-alpha-L-arabinopyranosyl]-30-noroleana-12,20(29)-di en-28-oic acid 28-O-[beta-D-glucopyranosyl-(1----6)-beta-D-glucopyranosyl] ester.     

Madhucosides A and B, protobassic acid glycosides from Madhuca indica with inhibitory activity on free radical release from phagocytes

The structures of madhucosides A (1) and B (2), isolated from the bark of Madhuca indica, were established as 3-O-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranosyl-28-O-[beta-D-xylopyranosyl(1-->2)-[alpha-L-rhamnopyranosyl(1-->4)]-beta-D-glucopyranosyl(1--> 3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl]protobassic acid and 3-O-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranosyl-28-O-[beta-D-xylopyranosyl(1-->2)-[alpha-L-rhamnopyranosyl(1-->4)]-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl]protobassic acid, respectively. These two compounds showed significant inhibitory effects on both superoxide release from polymorphonuclear cells in a NBT reduction assay and hypochlorous acid generation from neutrophils assessed in a luminol-enhanced chemiluminescence assay.     

紫菀正丁醇萃取液化学成分研究

目的：研究紫菀正丁醇萃取液的化学成分。方法：利用大孔树脂、硅胶柱层析以及制备液相分离化合物,并利用现代波谱技术进行结构鉴定。结果：从中药紫菀中正丁醇萃取部位分得9个化合物,其中紫菀皂苷类4个,分别为：3-O-[O-α-D-吡喃阿拉伯糖-（1→6）-β-D-吡喃葡萄糖基]-2β,3β,16α-三羟基齐墩果烷-12-烯-28-酸28-[O-β-D-吡喃木糖基-（1→3）-O-α-L-吡喃阿拉伯糖基-（1→4）-[O-β-D-呋喃芹菜糖基-（1→3）]-O-α-L-吡喃鼠李糖基-（1→2）-β-D-吡喃木糖基]酯（astersaponin A,1）、3-O-[O-α-L-吡喃阿拉伯糖基-（1→6）-β-D-吡喃葡萄糖基]-2β,3β,16α-三羟基齐墩果烷-12-烯-28酸8-[O-β-D-吡喃木糖基-（1→3）-O-α-L-吡喃阿拉伯糖基-（1→4）-[O-β-D-呋喃芹菜糖基-（1→3）-O-α-L-吡喃鼠李糖基-（1→2）-O-α-L-吡喃鼠李糖基-（1→3）]-β-D-吡喃木糖基]酯（astersaponin C,2）、3-O-[O-α-L-吡喃阿拉伯糖基-（1→6）-β-D-吡喃葡萄糖基]-2β,3β,16α-三羟基齐墩果烷-12-烯-28-酸28-[O-β-D-吡喃木糖基-（1→3）-O-α-L-吡喃阿拉伯糖基-（1→4）-O-α-L-吡喃鼠李糖基-（1→2）-β-D-吡喃木糖基]酯（astersaponin E,3）和3-O-[O-α-D-吡喃阿拉伯糖-（1→6）-β-D-吡喃葡萄糖基]-2β,3β,16α-三羟基齐墩果烷-12-烯-28-酸（4）,以及shionosides A（5）、epifriedelinol（6）、astin C（7）、二十四烷酸（8）和棕榈酸（9）。结论：化合物4为新的天然产物。     

土贝母中一个新的三萜皂苷

目的对土贝母Bolbostemma paniculatum的三萜皂苷成分进行分离和结构鉴定。方法采用反复柱色谱方法进行分离,通过理化性质和波谱分析鉴定结构。结果从土贝母中分离并鉴定了1个新的三萜皂苷脱木糖土贝母苷丙(dexylosyltubeimoside Ⅲ)。结论化合物为新化合物。     

An acetylated bidesmosidic saponin from Schefflera octophylla.

A new acetylated bidesmosidic triterpenoid saponin has been isolated from the leaves of Schefflera octophylla and structurally elucidated as 3-epi-betulinic acid 3-O-beta-D-6'-acetylglucopyranoside 28-[alpha-L-rhamnopyranosyl(1----4)-O-beta-D-glucopyranosyl(1----6)]-bet a-D-0-glucopyranoside [1].     

绞股蓝中新达玛烷型皂苷成分及其神经保护作用

采用色谱方法从绞股蓝叶分离得到1个新达玛烷型皂苷和2个已知达玛烷型皂苷,并分别通过HR-ESI-MS,1H-NMR,13C-NMR,2D-NMR,CD光谱等方法鉴定为3-O-[β-D-葡萄糖基(1→2)][β-D-葡萄糖基]-2α,3β,12β,20,24(S)-四羟基-达玛-25-烯-20-O-[β-D-木糖基(1→6)]-β-D-葡萄糖苷(1,新化合物,命名为gypenoside J5),3-O-[β-D-葡萄糖基(1→2)][β-D-葡萄糖基]-2α,3β,12β,20,24(R)-四羟基-达玛-25-烯-20-O-[β-D-木糖基(1→6)]-β-D-葡萄糖苷(2)和2α,3β,12β,20-四羟基-25-过氧氢-达玛-23-烯-3-O-[β-D-葡萄糖基(1→2)][β-D-葡萄糖基]-20-O-[β-D-木糖基(1→6)]-β-D-葡萄糖苷(3)。其中化合物1和2是24位差向异构体,通过圆二色谱(CD)确定其24位绝对构型。这3种化合物对H1299,HepG2,PC-3癌细胞显示出低细胞毒性。然而,它们对H2O2诱导的SH-SY5Y细胞氧化损伤具有剂量依赖性的保护作用,尤其是化合物1显示出最强的抗氧化作用。尽管还需进一步的体内实验来证明其活性,但目前的体外研究为绞股蓝潜在的神经保护作用提供了物质基础。     

槐花炭化学成分的研究

目的:研究中药槐花炭的化学成分。方法:用硅胶柱色谱法和光谱分析法分离和鉴定化学成分。结果:分得6个化合物,经光谱分析鉴定其结构分别为麦芽酚(1),3-羟基吡啶(2),麦芽酚-3-氧-[6′-氧-(4″-羟基-反式-桂皮酰基)]-β-D-吡喃葡萄糖苷(3),3-氧-[β-D-半乳吡喃糖基-(1→2)-p-β-葡萄吡喃醛酸糖基]槐二醇乙酯(4),3-氧-[β-D-半乳吡喃糖基.(1→2)-β-D-葡萄吡喃醛酸糖基]槐二醇甲酯(5),芦丁(6)。结论:化合物4为新化合物,化合物1,2,3,5为首次从槐花炭中获得。     

Chemical constituents of the aerial parts of Schnabelia tetradonta

A phytochemical study on the ethanol extract of the aerial parts of Schnabelia tetradonta led to the isolation of five new compounds, 1-5, together with seven known compounds. The structures of the new compounds were elucidated on the basis of spectral data interpretation as 2alpha,3alpha,23,29-tetrahydroxyolean-12-en-28-oic acid (1), 3-O-beta-d-glucuronopyranosyl-2beta,3beta,16beta-trihydroxy-28-norolean-12-en-15-on-23-oic acid (2), 21-O-beta-d-glucopyranosyl-3beta,21alpha,30-trihydroxyolean-13(18)-en-24-oic acid (3), 6-C-beta-l-arabinopyranosyl-8-C-alpha-l-arabinopyranosylapigenin (4), and 4-acetylaminoethylphenyl 1-O-[6-O-(Z)-p-methoxycinnamoyl-beta-d-glucopyranosyl(1-->2)]-[beta-d-glucopyranosyl(1-->3)]-alpha-l-rhamnopyranoside (5), respectively.     

Silenosides A-C, triterpenoid saponins from Silene vulgaris.

Three new triterpenoid saponins named silenosides A-C (1-3) were obtained from the roots of Silene vulgaris. Their structures were elucidated by spectral and chemical methods as beta-D-galactopyranosyl(1-->2)-beta-D-glucuronopyranosyl-3beta- hydrox y-23-oxoolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl(1-->3)-beta-D-xylopyranosyl(1-->4)-alpha-L- rhamnopyranosyl(1-->2)-beta-D-fucopyranoside; 3-O-beta-D-galactopyranosyl(1-->2)-beta-D-glucuronopyranosyl-3beta , 16alpha-dihydroxy-23-oxoolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl(1-->4)-[beta-D-glucopyranosyl(1-->2)]-alpha -L-rhamnopyranosyl(1-->2)-beta-D-fucopyranoside; and 3-O-alpha-L-arabinopyranosyl(1-->3)-[beta-D-galactopyranosyl(1-->2 )]- beta-D-glucuronopyranosyl-3beta, 16alpha-dihydroxy-23-oxoolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl(1-->4)-[beta-D-glucopyranosyl(1-->2)]-alpha -L-rhamnopyranosyl(1-->2)-beta-D-fucopyranoside, respectively.     

Antiproliferative triterpenes from the leaves and twigs of Juglans sinensis on HSC-T6 cells

Bioassay-guided fractionation of an 80% MeOH extract of leaves and twigs of Juglan sinensis has resulted in the isolation of four new triterpenes (1-4) and 17 known triterpenes (5-21). The new compounds were determined to be 1-oxo-3β,23-dihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside (1), 1-oxo-3β-hydroxyolean-18-ene (2), 3β,23-dihydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranoside (3), and 3β,22α-dihydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranoside (4) by spectroscopic analysis. Compounds 2, 13, 15, and 21 showed antiproliferative activities (14.2, 14.8, 15.6, and 11.0% at 100 μM, respectively) in HSC-T6 cells. Flow cytometry assays revealed that these compounds inhibited HSC-T6 proliferation by inducing apoptosis.     

翻白叶树根化学成分研究

目的:对翻白叶树根化学成分进行研究。方法:应用溶剂萃取、正相硅胶柱色谱、ODS开放柱色谱、Sephadex LH-20柱色谱以及制备高效液相进行分离和纯化,采用波谱技术进行结构鉴定。结果:分离并鉴定出10个化合物,分别为金色酰胺醇酯(asperglaucide,1),2-甲氧基-4-羟基苯酚-1-O-β-D-呋喃芹菜糖基-(1→6)-O-β-D-葡萄糖苷[2-methoxy-4-hydroxyphenol-1-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside,2],5,5’-二甲氧基-9-β-D-木糖基-(-)-异落叶松脂素[5,5’-dimethoxy-9-β-D-xylopyranosyl-(-)-isolariciresinol,3],(-)-表儿茶素[(-)-epicatechin,4],圣草酚(eriodictyol,5),花旗松素(taxifolin,6),3β-羟基-12-烯-28-乌苏酸(3β-hydroxy-12-en-28-ursolic acid,7),2β,3β-二羟基-12-烯-28-齐墩果酸(2β,3β-dihydroxy-12-en-28oleanolic acid,8),槲皮素(quercetin,9),豆甾-4-烯-3-酮(cholest-4-en-3-one,10)。结论:化合物1～10为首次从该植物中分得。     

猫儿刺叶中的三萜皂苷类成分

目的：研究猫儿刺（Ilex pernyi Franch）叶中的化学成分。方法：运用多种色谱方法进行分离纯化, 采用波谱解析并结合理化性质鉴定化合物结构。结果：分离得到 9 个化合物：2α, 23-二羟基-乌索酸-28-O-β-D-吡喃葡萄糖苷（1）,常春藤皂苷元-3-O-β-D-吡喃葡萄糖基（1→2）-α-L-吡喃阿拉伯糖苷（2）, 常春藤皂苷元-3-O-β-D-吡喃葡萄糖基（1→2）-β-D-吡喃葡萄糖苷 （3）,常春藤皂苷元-3-O-α-L-吡喃鼠李糖基 （1→2）-β-D-吡喃葡萄糖苷（4）, 23-羟基-乌索酸-3-O-β-D-吡喃葡萄糖苷（5）,竹节参苷Ⅳa （6）,23-羟基-乌索酸-3-O-β-D-吡喃葡萄糖醛酸甲酯苷（7）,铁冬青苷XXXVII （8）, 3-O-β-D-吡喃葡萄糖醛酸基-2α, 23-二羟基-乌索酸-28-O-β-D-吡喃葡萄糖苷（9）。结论：9 个化合物均为首次从该植物中分离得到。     

Abrusosides A-D, four novel sweet-tasting triterpene glycosides from the leaves of Abrus precatorius

In addition to abrusoside A [1], abrusosides B [2], C [3], and D [4], three further sweet glycosides based on the novel cycloartane-type aglycone, abrusogenin [5], were isolated from an n-BuOH-soluble extract of the leaves of Abrus precatorius. Using a combination of spectral methods, the structures of compounds 1-4 were assigned, respectively, as the 3-O-beta-D-glucopyranosyl, the 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-6-methylglucuronopyranosyl+ ++, the 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-glucopyranosyl, and the 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-glucuronopyranosyl derivatives of compound 5. After it established that compounds 1-4 were neither acutely toxic with mice nor mutagenic with Salmonella typhimurium strain TM677, they were found by a human taste panel to exhibit sweetness potencies in the range 30-100 times greater than sucrose.     

Chemical constituents from the aerial parts of Aster koraiensis with protein glycation and aldose reductase inhibitory activities

Two new eudesmane-type sesquiterpene glucosides, 9β-O-(E-p-hydroxycinnamoyl)-1β,6β-dihydroxy-trans-eudesm-3-en-6-O-β-D-glucopyranoside (1) and 9α-O-(E-p-hydroxycinnamoyl)-1α,6α-11-trihydroxy-trans-eudesm-3-en-6-O-β-D-glucopyranoside (2), were isolated by the activity-guidedfractionation of an EtOAc-soluble fraction from the aerial parts of Aster koraiensis. A new dihydrobenzofuran glucoside, (2R,3S)-6-acetyl-2-[1-O-(β-D-glucopyranosyl)-2-propenyl]-5-hydroxy-3-methoxy-2,3-dihydrobenzofuran (3), was also isolated, in addition to 15 known compounds. The structures of 1-3 were determined by spectroscopic data interpretation. All of the isolates were evaluated for in vitro inhibitory activity against the formation of advanced glycation end-products and rat lens aldose reductase.     

Kinmoonosides A-C, three new cytotoxic saponins from the fruits of Acacia concinna, a medicinal plant collected in myanmar

Three genuine saponins, named kinmoonosides A-C (1-3), have been isolated, together with a new monoterpenoid (4), from a methanolic extract of the fruits of Acacia concinna. The structures of kinmoonosides A-C were elucidated on the basis of spectral analysis as 3-O-?alpha-L-arabinopyranosyl(1-->6)-[beta-D-glucopyranosyl(1-->2) ]-b eta-D-glucopyranosyl?-21-O-?(6R, 2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2'E)-6'-hydroxyl-2'-hydroxymet hyl-6'-methyl-2',7'-octadienoyl-beta-D-quinovopyranosyl]-2, 7-octadienoyl?acacic acid 28-O-alpha-L-arabinofuranosyl(1-->4)-[beta-D-glucopyranosyl(1-->3)]-a lpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl ester (1); 3-O-?alpha-L-arabinopyranosyl(1-->6)-[beta-D-glucopyranosyl(1-->2) ]-b eta-D-glucopyranosyl?-21-O-?(6S, 2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2'E)-6'-hydroxyl-2'-hydroxymet hyl-6'-methyl-2',7'-octadienoyl-beta-D-quinobopyranosyl]-2, 7-octadienoyl?acacic acid 28-O-alpha-L-arabinofuranosyl(1-->4)-[beta-D-glucopyranosyl(1-->3)]-a lpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl ester (2); and 3-O-?alpha-L-arabinopyranosyl(1-->6)-[beta-D-glucopyranosyl(1-->2) ]-b eta-D-glucopyranosyl?-21-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl- 2,7-octadienoyl]acacic acid 28-O-alpha-L-arabinofuranosyl(1-->4)-[beta-D-glucopyranosyl(1-->3)]-a lpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl ester (3), respectively. The new monoterpenoid 4 was determined as 4-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2, 7-octadienoyl]-D-quinovopyranose. Compounds 1-3 showed significant cytotoxicity against human HT-1080 fibrosarcoma cells.