Three triterpenoid saponins acylated with monoterpenic acid from Gymnocladus chinensis

A new triterpenoid saponin acylated with monoterpenic acid, together with two known triterpenoid saponins, has been isolated from the fruit of Gymnocladus chinensis Baill. Their structures were elucidated as 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-((6S)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoyl)-β-L-arabinopyranosyl]-2,7-octadienoyl}-acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranosyl ester (1), gymnocladus saponin E (2), and gymnocladus saponin F₂ (3).     

A new triterpenoid saponin from Albizia julibrissin Durazz

A new triterpenoid, saponin hehuanoside A, was isolated together with the known triterpenoid saponins 2, 3, and 4 from the stem bark of Albizia julibrissin. With the help of chemical and spectral analyzes (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new triterpenoid saponin was elucidated as 21-O-[(6S)-2-trans-2,6-dimethyl-6-O-beta-d-quinovopyranosyl-2,7-octadienoyl]-3-O-beta-d-xylopyranosyl-(1 --> 2)-beta-d-fucopyranosyl-(1 --> 6)-beta-d-2-deoxy-2-acetamidoglucopyrasyl acacic acid 28-O-alpha-l-arabinofuranosyl-(1 --> 4)-[-beta-d-glucopyranosyl-(1 --> 3)]-alpha-l-rhamnopyranosyl-(1 --> 2)-beta-d-glucopyranosyl ester (1). Three known triterpenoid saponins 2-4 were identified on the basis of spectroscopic data.     

A new triterpenoid saponin from Albizia julibrissin Durazz

A new triterpenoid, saponin hehuanoside A, was isolated together with the known triterpenoid saponins 2, 3, and 4 from the stem bark of Albizia julibrissin. With the help of chemical and spectral analyzes (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new triterpenoid saponin was elucidated as 21-O-[(6S)-2-trans-2,6-dimethyl-6-O-beta-d-quinovopyranosyl-2,7-octadienoyl]-3-O-beta-d-xylopyranosyl-(1 --> 2)-beta-d-fucopyranosyl-(1 --> 6)-beta-d-2-deoxy-2-acetamidoglucopyrasyl acacic acid 28-O-alpha-l-arabinofuranosyl-(1 --> 4)-[-beta-d-glucopyranosyl-(1 --> 3)]-alpha-l-rhamnopyranosyl-(1 --> 2)-beta-d-glucopyranosyl ester (1). Three known triterpenoid saponins 2-4 were identified on the basis of spectroscopic data.     

九子参中一个新三萜皂苷

运用硅胶、SephadexLH-20、0DD以及高效液相色谱法,从九子参的根中分离得到一个新三萜皂苷和一个已知三萜皂苷。通过质谱以及一维二维核磁确定了化合物的结构。化合物1和2均为首次从该属植物中分离得到。     

Three New Triterpenoid Saponins from the Seeds of Vaccaria segetalis

Abstract

Three new triterpenoid saponins, named segetoside G (1), H (2) and I (3), have been isolated from the seeds of Vaccaria segetails. On the basis of chemical reaction and spectral data, their structures have been established as: 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl (1 → 3)]-β-D-(4-O-acetyl)-fucopyranosyl-gypsogenin-3-O-β-D-gal-actopyranosyl-(1 → 2)-β-D-(6-O-butyl ester)-glucuronopyranoside (1), 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-(5-O-acetyl)-arabinofuranosyl-(1 → 3)]-β-D-(4-O-acetyl)-fucopyranosyl-gypsogenin-3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranoside (2) and 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-(5-O-acetyl)-arabinofuranosyl-(1 → 3)]-β-D-(4-O-acetyl)-fucopyranosyl-quillaic acid-3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranoside (3).     

瘤果黑种草子的化学成分

目的研究中药瘤果黑种草子的化学成分。方法运用多种色谱方法分离化学成分;依据这些化学成分的理化性质和波谱(NMR、EI-MS)数据分析鉴定化合物的结构。结果从瘤果黑种草子中初步分离得到5个化合物,分别鉴定为胡萝卜苷(1)、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(2)、常春藤皂苷元-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(3)、3-O-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖常春藤皂苷元-28-O-β-D-吡喃葡萄糖酯苷(4)、山奈酚-3-O-β-D-吡喃葡萄糖基-(1→2)-β-D-吡喃半乳糖基-(1→2)-β-D-吡喃葡萄糖苷(5)。结论化合物4为首次从黑种草属植物中分离得到,化合物5为首次从该种植物中分离得到。     

New triterpenoid saponins from Patrinia scabiosifolia

Phytochemical investigation of methanol extract from the whole plants of Patrinia scabiosifolia Fisch. resulted in the isolation of three new triterpenoid saponins (1-3) along with twelve known triterpenoids (4-15). The structures of the new compounds were established as 11α, 12α-epoxy-3-O-β-D-xylopyranosyl-olean-28, 13β-olide (1), 11α, 12α-epoxy-3-O-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl-olean-28, 13β-olide (2), and 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl oleanolic acid 28-O-β-D-glucopyranoside (3) on the basis of various spectroscopic analyses (including different 1D and 2D NMR spectroscopies and high-resolution electrospray ionization mass spectrometry) and chemical evidences.     

东北铁线莲三萜皂苷对照品的制备

目的:制备一种用于东北铁线莲含量测定的三萜皂苷对照品。方法:采用大孔吸附树脂柱色谱和制备液相色谱进行分离,质谱和核磁共振波谱数据鉴定结构,高效液相色谱-蒸发光散射检测法测定纯度。结果:制备了符合含量测定用要求的三萜皂苷对照品3-O-α-L-吡喃鼠李糖基-(1→6)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃核糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖基齐墩果酸28-O-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖苷。结论:本试验结果可为东北铁线莲质量评价提供物质基础。     

Clematomandshurica saponin E, a new triterpenoid saponin from Clematis mandshurica

A new triterpenoid saponin, clematomandshurica saponin E, together with four known saponins were isolated and characterized from the roots and rhizomes of Clematis mandshurica (Ranunculaceae), a commonly used traditional Chinese medicine with anti-inflammatory and antirheumatoid activities. On the basis of spectroscopic analysis, including HR-ESI-MS, IR, 1D, and 2D NMR spectral data and hydrolysis followed by chromatographic analysis, the structure of the new triterpenoid saponin was elucidated as 3-O-α-L-rhamnopyranosyl-(1 → 6)-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 4)-β-D-ribopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside.     

Two new oleanane-type pentacyclic triterpenoid saponins from the husks of Xanthoceras sorbifolia Bunge

Two new triterpenoid saponins (1, 2) and a known saponin (3) were isolated from the husks of Xanthoceras sorbifolia Bunge., and their structures were elucidated as 3-O-β-D-glucopyranosyl(1 → 6)-[angeloyl(1 → 2)]-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl(1 → 2)-[β-D-glucopyranosyl(1 → 6)]-β-D-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (1), 3-O-β-D-glucopyranosyl-28-O-[β-D-glucopyranosyl(1 → 2)]-β-D-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (2), and 3-O-β-D-glucopyranosyl-28-O-[α-L-rhamnopyranosyl(1 → 2)]-β-D-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (3), on the basis of the spectral analysis of NMR and chemical methods. Cytotoxic assay indicated that none of them showed obvious inhibitory effect on the proliferation of two human tumor cell lines.     

维药斯亚旦化学成分研究

目的研究维药斯亚旦的化学成分。方法采用正相硅胶、ODS、Sephadex LH-20等柱色谱以及高效制备液相等手段进行分离纯化,并用化学方法和光谱方法鉴定了化合物的结构。结果从斯亚旦中分离鉴定了10个化合物,分别为:五加苷K(1)、常春藤皂苷元-3-O-α-L-鼠李糖基(1→2)-α-L-吡喃阿拉伯糖苷(2)、常春藤皂苷元-3-O-β-D-吡喃木糖基(1→3)-α-L-鼠李糖基(1→2)-α-L-吡喃阿拉伯糖苷(3)、quercetin-3-[6-ferulyl-β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucopyrano-side](4)、quercetin-3-sophorotriosides(5)、quercetin-3-glucosyl(1→2)-galactosyl(1→2)-glucoside(6)、quercetin-3-(6-feruloylglu-cosyl)(1→2)-galactosyl(1→2)-glucoside(7)、3-O-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖常春藤皂苷元-28-O-α-L-吡喃鼠李糖基(1→4)-β-D-吡喃葡萄糖基(1→6)-β-D-吡喃葡萄糖(8)、3-O-β-D-吡喃葡萄糖基(1→6)-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖常春藤皂苷元-28-O-α-L-吡喃鼠李糖基(1→4)-β-D-吡喃葡萄糖基(1→6)-β-D-吡喃葡萄糖苷(9)和芦丁(10)。结论化合物1,4,5为首次从黑种草属中分离得到,化合物6为首次从该种中分离得到。     

A pair of isomeric saponins with cytotoxicity from Albizzia julibrissin

Two new saponins have been isolated from the stem barks of Albizzia julibrissin Durazz, and their structures identified as 3-O-[beta-D-xylopyranosyl-(1 --> 2)-beta-D-fucopyranosyl-(1 --> 6)-beta-D-2-deoxy-2-acetoamidoglucopyranosyl]-21-O-{(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-[4-O-((6S)-2-trans-2-hydroxymethyl-6-hydroxy-6-methyl-2,7-octadienoyl)-beta-D-quinovopyranosyl]-2,7-octadienoyl}-acacic acid-28-O-beta-D-glucopyranosyl-(1 --> 3)-[alpha-L-arabinofuranosyl-(1 --> 4)]-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl ester (1) and 3-O-[beta-D-xylopyranosyl-(1 --> 2)-beta-D-fucopyranosyl-(1 --> 6)-beta-D-2-deoxy-2-acetoamidoglucopyranosyl]-21-O-{(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-[3-O-((6S)-2-trans-2-hydroxymethyl-6-hydroxy-6-methyl-2,7-octadienoyl)-beta-D-quinovopyranosyl]-2,7-octadienoyl}acacic acid 28-O-beta-D-glucopyranosyl-(1 --> 3)-[alpha-L-arabinofuranosyl-(1 --> 4)]-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl ester (2), based on chemical and spectral evidences, named as julibroside J19 and julibroside J18, respectively. Both compounds show significant inhibition action against HeLa, Bel-7402 and MDA-MB-435 cancer cell lines in vitro.     

Saponins from the roots ofPulsatilla koreana

From the roots ofPulsatilla koreana, three monodesmosides(pulsatilla saponins A, B and D) and two bisdesmosides(pulsatilla saponins F and H) were isolated. The structure of these saponins have been determined as hederagenin 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranoside(A), hederagenin 3-O-β-D-glucopyranosyl(1→4)-α-L-arabinopyranoside(B), hederagenin 3-O-α-L-rhamnopyranosyl (1→2)-[β-D-glucopyranosyl(1→4)]-α-L-arabinopyranoside(D), 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester (F) and 3-O-α-L-rhamnopyranosyl(1→2)-[β-D-glucopyranosyl(1→4)]-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester(H) on the basis of chemical and spectral studies. Pulsatilla saponin B is the first report of its presence in plants but saponins A, D, F, and H have recently been isolated from the same genusP. cernua.     

A triterpenoid saponin from Albizia julibrissin

A triterpenoid saponin (1) was obtained from the stem barks of Albizia julibrissin Durazz. Its structure was elucidated as 3-O-[beta-D-xylopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-beta-D-glucopyranosyl]-21-O-[(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-beta-D-quinovopyranosyl-2, 7-octadienoyl]-16-deoxy-acacic acid 28-O-beta-D-glucopyranosyl-(1 --> 3)-[alpha-L-arabinofuranosyl-(1 --> 4)]-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl ester (1), named as Julibroside J26, based on the chemical and spectral methods.     

玄参根中的一个新三萜四糖苷(英文)

在中药玄参提取分离的过程中,分离得到1个新三萜四糖苷3β-O-(β-D-xylopyranosyl-(1→2)-[β-D-glucopyranosyl(1→4)-β-D-glucopyranosyl-(1→3)]-β-D-fucopyranosyl-11,13(18)diene-olean-23α,28 dio1(1)和3个已知的苯乙醇苷(2～4),化合物2、3均为首次从该属植物中分离得到。通过1D,2D NMR和HR-ESI-MS等光谱数据阐明了化合物1的结构。     

Saponins from the stem bark ofKalopanax pictum var.magnificum (I)

Three triterpenoid saponins were isolated from the methanol extract of the stem bark ofKalopanax pictum Nakai var.magnificum (Araliaceae). The structures of these saponins were identified as hederagenin 3-O-α-L-arabinopyranoside, hederagenin-3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranoside and 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester.     

Gleditsia saponins

The chemical structure of gleditsia saponin C (GS-C), a major triterpenoid saponin of the fruit capsule of Gleditsia japonica Miq. (Leguminosae), comprised echinocystic acid, eight sugar units and two monoterpenyl groups ((+)2,6-dimethyl- and (+) 2-hydroxymethyl-6-methyl-6-(S)hydroxy-2- trans-2,7-octadienoyl groups). Methylation analysis of GS-C followed by determination with gas-liquid chromatography and mass spectrometry showed that the monoterpenyl moieties attach to the 2 and 3-positions of terminal L-rhamnose of the C-28 oligoside portion.     

Gleditsia saponins.

The chemical structure of gleditsia saponin C (GS-C), a major triterpenoid saponin of the fruit capsule of GLEDITSIA JAPONICA M IQ. (Leguminosae), comprised echinocystic acid, eight sugar units and two monoterpenyl groups ((+)2,6-dimethyl- and (+) 2-hydroxymethyl-6-methyl-6-(S)hydroxy-2- TRANS-2,7-octadienoyl groups). Methylation analysis of GS-C followed by determination with gas-liquid chromatography and mass spectrometry showed that the monoterpenyl moieties attach to the 2 and 3-positions of terminal L-rhamnose of the C-28 oligoside portion.     

A novel spinosin derivative from Semen Ziziphi Spinosae

A novel spinosin derivative, 6?-(4?'-O-β-D-glucopyranosyl)-vanilloyl spinosin (1) was isolated from the methanol extract of Semen Ziziphi Spinosae, together with five known flavonoids, swertish, spinosin, 6?-feruloylspinosin, isospinosin and kaempferol 3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranoside, and two alkanoids, zizyphusine and 6-(2',3'-dihydroxyl-4'-hydroxymethyl-tetrahydro-furan-1'-yl)-cyclopentene[c]pyrrole-1,3-diol. The structure of compound 1 was elucidated by spectroscopic methods including UV, IR, ESI-TOF-MS, 1D, and 2D NMR techniques.     

一种天然三萜皂苷的化学合成和抗肿瘤活性研究

目的 合成具有抗炎活性的天然三萜皂苷oleanolic acid 3-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranoside(1)。方法 以齐墩果酸为起始原料,采用逐步糖苷化策略,应用苄基、异丙亚甲基、乙酰氧基、过原酸酯等保护基方法,合成目标产物。以三萜皂苷β-hederin为阳性对照,采用MTT法测试目标物对肿瘤细胞的抑制活性。结果与结论 经13步反应,合成目标化合物,总收率23.7%,目标化合物结构经MS和1H-NMR确证。初步的体外药理实验结果表明,合成的皂苷产物仍然具有较强的肿瘤细胞毒活性。