黄花远志的新齐墩果烷型三萜皂甙

从云南产远志科药用植物黄花远志(PolygalaarillataBuchHamexDDon)茎皮的乙醇提取物中分离得到4个新的齐墩果烷型三萜皂甙,命名为黄花远志皂甙(arillatanoside)A～D。同时还分离得到1个已知的三萜皂甙远志甙(polygalasaponin)XXXV。它们的结构通过波谱方法推定。     

金铁锁的新三萜皂甙

从金铁锁（Psammosilene tunicoides W.C.Wu et C.Y.Wu)根部分离得到5个齐墩果烷型五环三萜皂苷,它们的结构通过波谱和化学方法分别鉴定为：3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl-gypsogenin(1),3-O-β-D-galactopyranosyl-(1→2)-[β-D-galactopyranosyl-(1→3)-β-D-glucuronopyranosyl-gypsogenin(2),3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyra-nosyl-gypsogenin-28-O-β-D-xylopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl(1→2)-β-D-fucopyranoside(LobatosideI,3),3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)-β-D-glucuronopyranosylgypsogenin-28-O-β-D-xylopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl(1→2)-β-D-fucopyranoside(4),3-O-β-D-galactopyranosyl-(1→）-β-D-glucuro-nopyranosyl-grpsogenin-28-O-β-D-xylopyranosyl-(1→4)-[β-D-6-O-acetylglucopyranosyl-(1→3)-β-D-glucuro-nopyranosyl-gypsogenin-28-O-β-D-xylopyranosyl-(1→4)-[β-D-6-O-acetylglucopyranosyl-(1→3)]-α-L-rh-amnopyranosyl(1→2)-β-D-fucopyranoside(5),其中5为新化合物,1和2为首次从自然界中分离得到。     

古蔺雪胆中的新三萜皂苷

从采自四川汉源县的古蔺雪胆(Hemsleya penxianensis var.gulinensiks)中分到9个三萜皂苷化合物,通过化学反应和光谱方法鉴定了它们的结构。其中7个为已知化合物,分别为齐墩果酸-28-O-β-D-比喃葡萄糖苷(1),3-O-β-D-吡喃葡萄糖醛基齐墩果酸苷(3),3-O-β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-α-L-吡喃阿拉伯糖苷(4),3-O-β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-β-D-吡喃葡萄糖苷(5),3-O-α-L-阿拉伯糖基—(1→3)—β—D-吡喃葡萄糖醛基—齐墩果酸—28—O—β—D—吡喃葡萄糖苷(6),3—O—(6′—丁酯)—β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-α-L-阿拉伯糖苷(7),3-O-(6′-丁酯)—β—D吡喃葡萄糖醛基—齐墩果酸—28-O-β-D-吡喃葡萄糖苷(8)。两个新化合物,即雪胆皂苷A(2)和雪胆皂苷B(9)。     

Glucuronide triterpene saponins from Bersama engleriana

Five 3-O-glucuronide triterpene saponins (1-5) were isolated from the stem bark of Bersama engleriana Gurke along with two known saponins, polyscias saponin C and aralia saponin 15, and one major C-glycoside xanthone, mangiferin. The structures of the saponins were established mainly by means of spectroscopic methods (one- and two-dimensional NMR spectroscopy as well as FAB-, HRESI-mass spectrometry) as 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-betulinic acid (1), 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl]-oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-xylopyranosyl-(1-->6)-beta-d-glucopyranosyl]-oleanolic acid (3), 3-O-[beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl]-oleanolic acid (4), and 3-O-[beta-d-glucopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-d-xylopyranosyl-(1-->6)-beta-D-glucopyranosyl]-oleanolic acid (5).     

大叶吊兰中一个新的甾体皂甙

从百合科植物大叶吊兰（Ｃｈｌｏｍｐｈｙｔｕｍ ｍａｌａｙｅｎｓｅ）根茎中分离得到１个新的呋甾烷型甾体皂甙,命名为大叶吊兰甙Ｅ（ｃｈｌｏｒｏｍａｌｏｓｉｄｅ Ｅ）。经波谱和化学方法证明明其结构为：２６－０－β－Ｄ－ｇｌｕｃｏｐｙｒａｎｏｓｙｌ－２２－ｈｙｄｒｏｘｙ－２５（Ｓ）－５ａ－ｆｕｒｏｓｔａｎ－１２－ｏｘｏ－３β,２６－ｄｉｏｌ－３－β－Ｄ－ｘｙｌｏｐｙｒａｎｏｓｙｌ（１→３）〖α－Ｌ－ａｒａ     

In vivo anti-inflammatory activity of saponins from Bupleurum rotundifolium

Seven oleanane-type triterpene saponins were isolated from the methanolic extract of the aerial parts of Bupleurum rotundifolium. They were identified on the basis of their spectral data as 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl] echinocystic acid (saponin 1), 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-fucopyranosyl] 11-methoxy-primulagenin A (saponin 2), rotundioside E (saponin 3), rotundioside F (saponin 4), 3beta-sulfate, 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl] ester of primulagenin A (saponin 5), rotundioside C (saponin 6) and 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-fucopyranosyl] 11-methoxy-16beta,21alpha,28-trihydroxyolean-12-ene (saponin 7). All these saponins proved to be effective against TPA-induced ear edema in mice. Their ID50 were determined to be 248, 288, 128, 99 and 297 nmol/ear for saponin 1, 2, 3, 4 and 6, respectively. Saponins 3 and 6 were also active on a TPA multiple-dose model of skin chronic inflammation.     

New Triterpenoid Glycosides from Hemsleya penxianensis var. gulinensis

Two new triterpenoid saponins were isolated from the rools of Hemsleya penxianensis var. gulinensis together with seven known saponins oleanolic acid 28-O-β-D-glucopyranoside (1), oleanolic acid 3-O-β-D-glucuropyranoside(3), 3-O-β-D-glucuropyranosyl-oleanolic acid-28-O-α-L-arabinopyranoside(4).     

马槟榔甜味蛋白的研究Ⅱ．甜蛋白Ⅱ和甜蛋白Ⅰ的比较

从马槟榔（Capparis masaikai Levl．）种子分离鉴定了二种甜蛋白：甜蛋白I（mabinlinⅠ或MaⅠ）分子量MWll600,等电点PⅠll.8;甜蛋白Ⅱ（mabinlinⅡ或MaⅡ）MW 10400,PⅠll.3。另一组分mabinlinⅡ MW10200,pl 11.8,可能是提取过程产物。MaⅡ有84个氨基酸残基,比MaⅠ少15个。它们有80个氨基酸残基是共同的,都是缺丝氨酸和蛋氨酸的单一多肽链。MaⅠ还缺赖氨酸和酪氨酸。测不出有自由SH基。在8 M尿素中用巯基乙醇还原处理,两种甜蛋白分子都可转变为二聚体而失去甜味。     

Studies on the Structures of Two New Triterpene Saponins C and D from Polygala japoni-ca Houtt

Two new triterpene saponins C and D have been isolated from the aerial parts of Polygala japonica Houtt. Their molecular formulas: C42H68O15 were structural isomers of each other. Acid hydrolysis of the two saponins all produced a sapogenin (2a, 3a, 24-trihydroxyo-lean-12-ene-28-oic acid) and D-glucoses. But only the saponin D could be hydrolyzed in the alkaline solution, the products were identical with those from acid hydrolysis. Their structures have been established by means of 1HNMR,13CNMR and MS as 3-O-[β-D-glucopyranosyl(l→2)β-D-glucopyranosyl] 2α, 3α, 24-trihydroxyolean-12-ene-28-oic acid, 28-O-[β-D-glucopy-ranosyl (1→2)-β-D-glucopyranosyl] 2α, 3α, 24-trihydroxyolean-12-ene-28-oic acid.     

Two new triterpene saponins from the anti-inflammatory saponin fraction of Ilex pubescens root

The saponin fraction from the ethanolic extracts of the root of Ilex pubescens Hook. et Arn. (Ilexaceae) was found to exhibit potent anti-inflammatory effects on carrageenan-induced paw edema in rats. Two novel triterpene saponins, pubescenosides C and D (1 and 2, resp.), together with five known saponins were isolated from this saponin fraction. The structures of 1 and 2 were elucidated as (20beta)-3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]ursa-12,18-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester, and (20beta)-3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]ursa- 12,18-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester, respectively, on the basis of chemical and spectroscopic data. Five known saponins isolated from the saponin fraction were identified as ilexsaponin B(1), B(2), B(3), A(1), and chikusetsusaponin IV(a).     

Triterpenoid Saponins from Pulsatilla cernua (Thunb.)

To investigate saponins from the roots of Pulsatilla cernua (Thunb.) Bercht. et Opiz., two new compounds together with five known triterpenoid saponins were isolated. The structures of the two new triterpenoid saponins, named cernuasides A and B, were elucidated as 3-O-[β-D-xylopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→4)]-α-Larabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 1) and 3-O-[α-L-arabinopyranosyl(1→3)]-[α-L-rhamnopyranosyl (1→2)]-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 2) by 1D, 2D-NMR techniques, ESIMS analysis, as well as chemical methods.     

Triterpenoid Saponins from Pulsatilla cernua (Thunb.)Bercht. et Opiz.

To investigate saponins from the roots of Pulsatilla cernua (Thunb.) Bercht. et Opiz., two new compounds together with five known triterpenoid saponins were isolated. The structures of the two new triterpenoid saponins, named cernuasides A and B, were elucidated as 3-O-[β-D-xylopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→4)]-α-Larabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 1) and 3-O-[α-L-arabinopyranosyl(1→3)]-[α-L-rhamnopyranosyl (1→2)]-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 2) by 1D, 2D-NMR techniques, ESIMS analysis, as well as chemical methods.     

Saponins from the roots of Chiococca alba and their in vitro anti-inflammatory activity

Five triterpenoidal saponins were isolated from the roots of Chiococca alba (L.) Hitchc. (Rubiaceae). Two of the saponins, chiococcasaponin III (3-O-β-d-glucopyranurosyl-3β-hydroxyolean-12,15-dien-28-oic acid 28-O-β-d-xylopyranosyl (1 → 4)-α-l-rhamnopyranosyl (1 → 2)-α-l-arabinopyranosyl ester) and chiococcasaponin IV (3-O-β-d-glucopyranurosyl-3β-hydroxyolean-12,15-dien-28-oic acid 28-O-α-l-rhamnopyranosyl (1 → 2)-α-l-arabinopyranosyl ester) were new and their structures were elucidated on the basis of extensive application of NMR techniques and high resolution electrospray mass spectrometry together with acid hydrolysis product analysis. As part of our investigations on the chemical profile and pharmacological activity of the roots of C. alba, we report the results of the evaluation of the activity of the saponin fractions against in vitro lipopolysaccharide-induced inflammation. The results found, strongly support the fractions I, III and IV as having anti-inflammatory properties.     

Acetylated glucuronide triterpene bidesmosidic saponins from Symplocos glomerata

Nine new bidesmosidic 3-O-glucuronide oleanane triterpenoid saponins were isolated from the stem bark of Symplocos glomerata King along with two known saponins, salsoloside C and copteroside E, and two major lignans, (-)-pinoresinol and (-)-pinoresinol-4'-O-beta-D-glucopyranoside. The structures of the new saponins were established using one- and two-dimensional NMR spectroscopy and mass spectrometry as, 3-O-[beta-D-xylopyranosyl(1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[beta-D-xylopyranosyl(1-->4)-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[beta-D-xylopyranosyl (1-->4)-[2,3-O-diacetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[alpha-L-arabinopyranosyl(1-->4)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[alpha-L-arabinopyranosyl (1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-xylopyranosyl (1-->2)]-[beta-D-xylopyranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-glucopyranosyl (1-->2)]-[beta-D-xylopyranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-glucopyranosyl (1-->2)]-[alpha-L-arabinofuranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, and 3beta-O-[beta-D-xylopyranosyl(1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-morolic acid. The EtOH and EtOAc extracts of the stem bark showed no cytotoxic activity. At a concentration of 370 microg/ml, the saponin mixture showed haemolytic activity and caused 50% haemolysis of a 10% suspension of sheep erythrocytes.     

龙舌兰发酵叶汁中的一个新甾体皂苷

从龙舌兰（Agave americana)的发酵叶汁中分离到一个新甾体皂苷。结合波谱和化学方法,新化合物的结构鉴定为替告皂苷元3－O－α－L－鼠李吡喃糖基－（1→3)－β-D-葡萄吡喃糖基－（1→2）-[β-D-葡萄吡喃糖基－（1→3)-β－D－葡萄吡喃糖基－（1→4）－β－D－半乳吡喃糖苷。     

Saponins of the Rhizome of Panax japonicus C. A. Meyer var. major (Burk.)Wu et Feng Collected in Qinling Mountain (Shaanxi)

From the rhizome of Panax japonicus C. A. Meyer var major (Burk.) Wu et Feng, collected in Qinling Mountain (Shaanxi), seven saponins were isolated. By means of 13C NMR, FAB-MS and comparison with authentic samples, six of them were identified with chikusetsusaponin Ⅴ (=ginsenoside Ro), Ⅳa, oleanolic acid 28-O-β-D-glucoside, ginsenoside Re, Rg2 and notoginsenoside R2. Another saponin was proved to be chikusetsusaponin Ⅳa methylester, and its structure was elucidated to be oleanolic acid (3-O-β-D-glucorunopyranosyl-methylate)-28-O-β-D-glucopyranoside. A comparison of sapoinin constituents of this variety collected in Qinling Mountain (Shaanxi) and Hengduan Mountains (Yunnan) was provided. As a common characteristic of both rhizome, it has been proved that the saponins of oleanane type were main constituents and the saponins of dammarane type were minor constituents. But some differences also has been found in both materials (Tab. 1). From the relationship between the biosynthesis pathway of triterpenoids and plant phytogenetics, this is a phenomenon of chemical polymorphism in a variety, which followed in the train of geographical distribution, ledto appearance of a che- mical evolution in the process of evolution and of spread of this variety.     

Triterpene saponins from Cyclamen hederifolium

Five triterpene saponins never reported before, hederifoliosides A-E, and four known triterpene saponins were isolated from the tubers of Cyclamen hederifolium. The structures of hederifoliosides A-E were determined as 3β,16α-dihydroxy-13β,28-epoxyolean-30-oic acid 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 3β,16α-dihydroxy-13β,28-epoxyolean-30-oic acid 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 3β,16α-dihydroxy-13β,28-epoxyolean-30-al 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-[β-D-glucopyranosyl-(1 → 6)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 30-O-β-D-glucopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-3β,16α,30-trihydroxyolean-12-en-28-al 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 30-O-β-D-glucopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-3β,16α,28,30-tetrahydroxyolean-12-en 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated against a small panel of cancer cell lines including Hela, H-446, HT-29, and U937. None of the tested compounds, in a range of concentrations between 1 and 50 μM, caused a significant reduction of the cell number.     

New Cytotoxic Saponins from Lysimachia davurica Ledeb.

To investigate the saponins from whole plants of Lysimachia davurica Ledeb., two new saponins named davuricoside I （compound 1） and E （compound 2） were isolated. Their chemical structures were elucidated as 3β, 16α, 28, 29-tetrihydroxy-olean-12-en-3-O-β-D-glucopyranosyl-（1→2）-β-D-glucuronopyranoside （compound 1） and 3β, 16α, 29-trihydroxy-13, 28-epoxy-oleanane-3-O-β-D-glucopyranosyl-（1→2）-β-D-glucuronopyranoside （compound 2） on the basis of their one- and two-dimensional nuclear magnetic resonance and mass spectrometry data, and chemical methods. Compound 1 showed significant cytotoxic activity against human A2780 cells.     

金铁锁的两个新三萜皂苷

从石竹科植物金铁锁(Psammosilene tunicoides W．C．Wu et C．Y．Wu)根部分离得到4个齐墩果酸型五环三萜皂苷。它们的结构通过波谱和化学方法分别鉴定为：3-O-β-D-galac-topyranosyl-(1→2 )-β-D-6-O-methylgtucuronopymnosyl-quillaic acid (1),3-O-β-D-galactopymnosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-gtucuronopyranosyl-quillaic acid (2),3-O-β-D-galactopyrano-syl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-6-O-methylgtucuronopyranosyl-quillaic acid(3),3-O-β-D-galactopymnosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-6-O-ethylgtucuronopyranosyl-quillaic acid(4)。其中1为木鳖子中发现的次甙,3和4为新化合物。     

广东冬青中的三萜及三萜皂甙成分

从广东冬青（Ｉｌｅｘ ｋｗａｎｇｔｕｎｇｅｎｓｉｓ）的叶中分离得到四个三萜皂甙和三个三萜成分,通过光谱解析及化学方法,三个三萜成分分别鉴定为齐墩果酸（１）、熊果酸（２）和常春藤皂甙元（３）;四个三萜皂甙成分分别鉴定为齐墩果酸３－Ｏ－β－Ｄ－吡喃葡萄糖基－（１→３）－α－Ｌ－吡喃阿拉伯糖甙（４）、齐墩果酸３－Ｏ－β－Ｄ－吡喃葡萄糖基－（１→２）－α－Ｌ－吡喃阿拉伯糖甙（５）、齐墩果酸３－Ｏ－β－Ｄ－