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).     

黄花倒水莲降血脂活性成分研究

从黄花倒水莲Polygala fallaxHem sl.根的降血脂有效部位中分离得到四个皂苷类化合物,分别鉴定为3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl presenegen in 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)--βD-fucopyransoyl ester(Ⅰ)、3-O--βD-glucopyranosyl-(1→2)--βD-glucopyranosyl presenegen in 28-O-β-D-xy-lopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-(3-O-acetyl)-β-D-fucopyranosyl ester(Ⅱ)、3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl presenegen in 28-O-β-D-xylopyranosyl-(1→4)--αL-rhamnopyranosyl-(1→2)-(4-O-acetyl)-β-D-fucopyranosyl ester(Ⅲ)和3-O-β-D-glucopyranosyl-(1→2)--βD-glucopyranosyl presenegen in 28-O-β-D-xylopyrano-syl-(1→4)-α-L-rhamnopyranosyl-(1→2)-(3,4-d iacetyl)--βD-fucopyranosyl ester(Ⅳ)。     

Three new triterpene saponins from two species of Carpolobia

Three new acetylated triterpene saponins 1-3 were isolated from the roots of Carpolobia alba and C. lutea. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, and 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, respectively.     

Gleditsiosides N-Q, new triterpenoid saponins from Gleditsia sinensis.

The structures of gleditsiosides N, O, P, and Q (1-4), isolated from anomalous fruits of Gleditsia sinensis, were characterized as novel complex bisdesmosidic triterpenoid glycosides acylated with monoterpenoid units, by means of extensive 1D and 2D NMR studies. The four compounds shared a common structural feature with a trisaccharide [(beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-be ta- D-glucopyranoside)] affixed to C-3 and a tetrasaccharide [(beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-r hamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester)] attached to C-28. Gleditsioside P (3) is the first saponin of this type found to date bearing three monoterpenoid units.     

Four new triterpenoid saponins from Conyza blinii

Three new bisdesmosidic saponins named conyzasaponins A, B, and C (1-3) and one new monodesmosidic saponin, conyzasaponin G (4), were isolated from the aerial parts of Conyza blinii. Their structures were elucidated on the basis of extensive NMR (DEPT, DQF-COSY, HOHAHA, HMQC, HMBC, and NOESY) and MS studies. Compounds 1-3 share a common prosapogenin, bayogenin 3-O-beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside, which is identical with conyzasaponin G (4), and differ in the structures of the ester-linked sugar moieties at C-28. Conyzasaponin A (1) is the 28-O-beta-D-apiofuranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester, conyzasaponin B (2), the 28-O-beta-D-apiofurano- syl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester, and conyzasaponin C (3), the 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester of the prosapogenin, respectively.     

合欢皂甙J6的结构鉴定

目的 :从合欢皮中分离皂甙。方法 :用色谱法分离 ,波谱法鉴定其结构。结果和结论 :从合欢皮的 95%乙醇提取物中分得 1个三糖链八糖皂甙 ,结构为 3-O [β-D 吡喃木糖基 ( 1→ 2 )-α-L 吡喃阿拉伯糖基 ( 1→ 6)-β-D 2 去氧 2 乙酰胺基 吡喃葡萄糖基 ] 21O {6S2 反式2羟甲基6甲基6-o[4-O ( 6S-2 反式-2 羟甲基 6-甲基 6-羟基 2 ,7 辛二烯酰基 ) β D 吡喃鸡纳糖基 ] 2 ,7 辛二烯酰基 } 金合欢酸-28-O-β-D 吡喃葡萄糖基 (1→ 3)[α- L 呋喃阿拉伯糖基 (1→ 4) ] α L 吡喃鼠李糖基 (1→ 2)-β-D 吡喃葡萄糖酯 ,为新化合物 ,命名为合欢皂甙J6 。     

Junceosides A-C, new triterpene saponins from Arenaria juncea.

Three novel triterpenoid saponins, junceosides A (1), B (2), and C (3), together with two known saponins have been isolated from the roots of Arenaria juncea. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-glucopyranosyl(1-->3)-[beta-D-xylopyranosyl-(1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (1), 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (2), and 3-O-beta-D-xylopyranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (3).     

Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum

Four novel triterpenoid saponins, glandulosides A (1), B (2), C (3), and D (4), together with two known saponins (5 and 6) have been isolated from the roots of Acanthophyllum glandulosum. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-d-galactopyranosyl-(1-->6)]-beta-D-galactopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-3-O-acetyl-beta-D-fucopyranoside (2), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-3,4-di-O-acetyl-beta-D-fucopyranoside (3), and 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-[3-O-acetyl-beta-D-quinovopyranosyl-(1-->4)]-beta-D-fucopyranoside (4).     

Acylated preatroxigenin glycosides from Atroxima congolana

Six new acylated bisdesmosidic preatroxigenin saponins named atroximasaponins E1, E2 (1, 2), F1, F2 (3, 4), and G1, G2 (5, 6) were isolated as three inseparable mixtures of the trans- and cis-p-methoxycinnamoyl derivatives, from the roots of Atroxima congolana. Their structures were established through extensive NMR spectroscopic analysis as 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin E1, 1), and its cis-isomer, atroximasaponin E2 (2), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin F1, 3), and its cis-isomer, atroximasaponin F2 (4), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-apiofuranosyl-(1-->3)-[alpha-l-rhamnopyranosyl-(1-->2)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin G1, 5), and its cis-isomer, atroximasaponin G2 (6), respectively.     

Two new biologically active triterpene saponins from Acanthophyllum squarrosum

Two novel triterpenoid saponins (1 and 2) have been isolated from the roots of Acanthophyllum squarrosum. The structures were established mainly by a combination of 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-be ta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3 )-b eta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L- rhamnopyranosyl-(1-->3)]-beta-D-fucopyranoside (1) and 3-O-beta-D-glucopyranosylgypsogenin-28-O-alpha-L-rhamnopyranosyl-( 1-- >2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6 )]- beta-D-glucopyranoside (2). Compound 1 showed a moderate concentration-dependent immunomodulatory effect in an in vitro lymphocyte proliferation assay.     

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.     

Biologically active triterpenoid saponins from Acanthopanax senticosus

Three new triterpenoid saponins, acanthopanaxosides A (1), B (7), and C (13), were isolated from the leaves of Acanthopanax senticosus, together with 12 known saponins. The structures of these new saponins were established as 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-30-nor-olean-12,20(29)-dien-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-6-O-acetyl-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (1), 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-6-O-acetyl-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (7), and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-3beta-hydroxyolean-12-ene-28,29-dioic acid (13), on the basis of spectroscopic analysis and chemical degradation. Among the known compounds, sessiloside and tauroside H1 are reported for the first time from A. senticosus. The biological activity of compounds 1-15 was examined against pancreatic lipase. Ciwujianoside C1 (6), tauroside H1 (11), 3-O-alpha-rhamnopyranosyl-(1-->2)-alpha-arabinopyranosyl mesembryanthemoidigenic acid (12), acanthopanaxoside C (13), sessiloside (14), and chiisanoside (15) inhibited pancreatic lipase activity in vitro. In turn, ciwujianosides C2 (3), D2 (5), C4 (8), and C3 (10) and hederasaponin B (9) enhanced this enzyme.     

素馨花三萜皂苷类化学成分研究

目的:研究木犀科茉莉属植物素馨花干燥花蕾的化学成分。方法:通过硅胶柱色谱、Sephadex LH-20柱色谱和重结晶等方法进行分离纯化,根据化合物的理化性质和波谱数据鉴定结构。结果:从素馨花干燥花蕾70%乙醇提取物中分离得到6个三萜皂苷类化合物,分别鉴定为3-O-α-L-吡喃鼠李糖基(1→2)-β-D-吡喃木糖基常春藤皂苷元-28-O-β-D-吡喃半乳糖基(1→6)-β-D-吡喃半乳糖酯苷(1)、常春藤皂苷元3-O-β-D-吡喃葡萄糖基(1→3)-α-L-吡喃阿拉伯糖苷(2)、2α,3β,23-trihydroxyolean-12-en-28-oic-O-β-D-glucopyranosyl ester(3)、常春藤皂昔元-3-O-β-D-吡喃木糖基(1→3)-α-L-吡喃鼠李糖基(1→2)-α-L-吡喃阿拉伯糖苷(4)、2α,3β,23-trihydroxyolean-12-en-28-oic-O-α-L-rhamnopyranosyl(1→4)-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester(5)、常春藤皂苷元-3-O-α-L-吡喃鼠李糖基(1→)2-α-L-吡喃阿拉伯糖苷(6)。结论:化合物1为新化合物,化合物26为首次从茉莉属植物中分离得到。     

Five new triterpene saponins from Pulsatilla patens var. multifida

Five new oleanane-type glycosides (1-5), along with two known triterpene saponins, were isolated from the roots of Pulsatilla patens var. multifida (Ranunculaceae). The structures of the new triterpene saponins were elucidated as 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-galactopyranosyl hederagenin 28-O-beta-D-glucopyranosyl ester (1), hederagenin 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->6)]-beta -D-galactopyranoside (2), 3-O-beta-D-glucopyranosyl bayogenin 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester (3), 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-galactopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester (4), and 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->6)]-beta -D-galactopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester (5). Structure elucidation was accomplished by 1D and 2D NMR (HMQC, HMBC, and ROESY) methods, FABMS, and hydrolysis.     

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.     

Biologically active triterpene saponins from callus tissue of Polygala amarella.

A new bioactive saponin (1), together with a known saponin (polygalasaponin XXVIII) has been isolated from the callus tissue culture of Polygala amarella. Based on spectroscopic data, especially direct and long-range heteronuclear 2D NMR analysis and on chemical transformations, the structure of 1 was elucidated as 3-O-beta-D-glucopyranosyl presenegenin-28-O-beta-D-galactopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-fucopyranoside. Both saponins showed significant immunological properties based on the enhancement of granulocyte phagocytosis in vitro.     

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.     

New lignan glycosides with potent antiinflammatory effect, isolated from Justicia ciliata

Two new lignan glycosides, 4-O-[alpha-L-arabinopyranosyl-(1' "-->2' ')-beta-D-xylopyranosyl-(1' " '-->5' ')-beta-D-apiofuranosyl]diphyllin (1), named ciliatoside A (1), and 4-O-?[beta-D-apiofuranosyl-(1' " "-->3' ")-alpha-L-arabinopyranosyl-(1' "-->2' ')][beta-D-xylopyranosyl-(1' " '-->5' ')]-beta-D-apiofuranosyl?diphyllin (2), named ciliatoside B (2), were isolated from the whole plant of Justicia ciliata. The structures of 1 and 2 were determined by spectral and chemical methods. Compounds 1 and 2 strongly inhibited the accumulation of NO(2)(-) in lipopolysaccharide-stimulated RAW 264.7 cells in a concentration-dependent manner with IC(50) values of 27.1 +/- 1.6 and 29.4 +/- 1.4 microM, respectively.     

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.