3,12-di-O-acetyl-20-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)dammar-24-ene-3β,12β,20(S)-triol | 39262-15-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,12-di-O-acetyl-20-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)dammar-24-ene-3β,12β,20(S)-triol
• 英文别名: 3β,12β-diacetoxy-20S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)dammar-24-ene；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2S)-2-[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-3,12-diacetyloxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 39262-15-2
• 化学式: C₄₈H₇₄O₁₄
• 分子量: 875.107
• InChiKey: WBYLBMHZDWYUTP-BKGKXQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  62
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3,12-di-O-acetyl-20-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)dammar-24-ene-3β,12β,20(S)-triol 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以100%的产率得到人参皂苷CK
  参考文献：
  名称：

  Synthesis of 20S-protopanaxadiol 20-O-β-D-glucopyranoside, a metabolite of Panax ginseng glycosides, and compounds related to it

  摘要：

  开发了一种准备性的半合成方法，以制备人参苷的代谢产物20S-原人参二醇20-O-β-D-葡萄糖苷 (1)。首次合成了20S-羟基达马烯-24-酮-3,12-二酮、3β,20S-二羟基达马烯-24-酮和3β,12α,20S-三羟基达马烯-24-烯的20-O-β-D-葡萄糖苷。

  DOI：

  10.1007/s10600-006-0179-2
• 作为产物：
  描述：

  原人参二醇 在 吡啶 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 3,12-di-O-acetyl-20-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)dammar-24-ene-3β,12β,20(S)-triol
  参考文献：
  名称：

  人参皂苷，人参糖苷的半合成类似物

  摘要：

  摘要在氧化银存在的条件下，将dammar-24-ene-3,12β，20（S）-三醇与2,3,4,6-四-O-乙酰基-α-d-吡喃葡萄糖基溴化物（A）糖基化二氯甲烷中得到乙酰化的3-，12-，20-，3,12-二-和3,20-二-O-β-d-吡喃葡萄糖基衍生物的混合物，总产率为83-84.5％ 。在相似的条件下，达玛-24-烯-3,12β，20（S）-三醇的3-O-乙酰基衍生物得到12-和20-O-β-d-吡喃葡萄糖基衍生物的混合物。在氰化汞存在的条件下，在硝化甲烷中，将异黄酮三醇[dammar-24-ene-3α，12β，20（S）-三醇]与糖基溴化物A和3,4,6-三-O-乙酰基-β缩合-在2,4存在下的d-吡喃葡萄糖1,2-（原乙酸叔丁酯）

  DOI：

  10.1016/0008-6215(88)85045-6

文献信息

• Synthesis of a Biologically Active Fluorescent Derivative of GM1, a Main Ginseng Saponin Metabolite Formed by Intestinal Bacteria.
  作者：Hideo HASEGAWA、Ryuichi SUZUKI、Chisato WAKABAYASHI、Jun MURATA、Yasuhiro TEZUKA、Ikuo SAIKI、Shigetoshi KADOTA

  DOI：10.1248/bpb.21.513

  日期：——

  A fluorescent derivative of GM1 [20-O-β-D-glucopyranosyl-20(S)-protopanaxadiol], a main Ginseng saponin metabolite formed by intestinal bacteria, was obtained from the condensation of its trisnor-aldehyde derivative with dansyl hydrazine. The dansylated GM1 fluoresced strongly and showed almost the same properties as its parent compound in lipophilicity and biological activities, so this fluorescent compound might provide an insight into the mechanism of pharmacological activities of GM1.

  一种人参皂苷代谢物GM1 [20-O-β-D-葡萄糖基-20(S)-原人参二醇]的荧光衍生物，是由其三降醛衍生物与丹磺酰肼缩合而得。这种丹磺酰化的GM1具有强荧光性，并且在亲脂性和生物活性方面与其母体化合物表现出几乎相同的性质，因此这种荧光化合物可能有助于深入了解GM1的药理活性机制。
• Studies on the saponins of ginseng. IV. On the structure and enzymatic hydrolysis of ginsenoside-Ra1.
  作者：HARUYO KOIZUMI、SHUICHI SANADA、YOSHITERU IDA、JUNZO SHOJI

  DOI：10.1248/cpb.30.2393

  日期：——

  The presence of ginsenoside-Ra in Ginseng Radix has been demonstrated by thin-layer chromatography. Recently, ginsenoside-Ra was shown to be a mixture of more than two saponins. Among them, ginsenoside-Ra1 was isolated and its structure was determined on the basis of spectral, chemical and enzymatic hydrolysis evidence as 20 (S)-protopanaxadiol 3-O-β-D-glucopyranosyl (1→2)-β-D-glucopyranosido-20-O-β-D-xylopyranosyl (1→4)-α-L-arabinopyranosyl (1→6)-β-D-glucopyranoside (1). Besides compound K (8), three prosapogenins, 20 (S)-protopanaxadiol 3-O-β-D-glucopyranosido-20-O-β-D-glucopyranoside (7), 20 (S)-protopanaxadiol 3-O-β-D-glucopyranosido-20-O-β-D-xylopyranosyl (1→4)-α-L-arabinopyranosyl (1→6)-β-D-glucopyranoside (9), and 20 (S)-protopanaxadiol 20-O-β-D-xylopyranosyl (1→4)-α-L-arabinopyranosyl (1→6)-β-D-glucopyranoside (10) were obtained in the course of enzymatic hydrolysis of ginsenoside-Ra1. Further, 20 (S)-protopanaxadiol 3-O-β-D-glucopyranosido-20-O-α-L-arabinopyranosyl (1→6)-β-D-glucopyranoside (6), 7 and 8 were obtained by enzymatic hydrolysis of ginsenoside-Rb2 (4). The course of enzymatic hydrolysis of ginsenosides with naringinase is also discussed.

  通过薄层色谱法已证实人参中存在人参皂苷-Ra。近期研究表明,人参皂苷-Ra是两种以上皂苷的混合物。其中,人参皂苷-Ra1被分离出来,并通过光谱、化学和酶解水解证据确定其结构为20(S)-原人参二醇3-O-β-D-葡萄糖基(1→2)-β-D-葡萄糖苷-20-O-β-D-木糖基(1→4)-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(1)。 除了化合物K(8)外,在人参皂苷-Ra1的酶解水解过程中还得到了三个原皂苷: - 20(S)-原人参二醇3-O-β-D-葡萄糖苷-20-O-β-D-葡萄糖苷(7) - 20(S)-原人参二醇3-O-β-D-葡萄糖苷-20-O-β-D-木糖基(1→4)-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(9) - 20(S)-原人参二醇20-O-β-D-木糖基(1→4)-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(10) 此外,通过人参皂苷-Rb2(4)的酶解水解获得了: - 20(S)-原人参二醇3-O-β-D-葡萄糖苷-20-O-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(6) - 化合物7和8 文中还讨论了人参皂苷与柚皮苷酶的酶解水解过程。
• Akao, Teruaki; Kanaoka, Matao; Kobashi, Kyoichi, Biological and pharmaceutical bulletin, 1998, vol. 21, # 3, p. 245 - 249
  作者：Akao, Teruaki、Kanaoka, Matao、Kobashi, Kyoichi

  DOI：——

  日期：——
• Synthesis of 20S-protopanaxadiol 20-O-β-D-glucopyranoside, a metabolite of Panax ginseng glycosides, and compounds related to it
  作者：L. N. Atopkina、V. A. Denisenko

  DOI：10.1007/s10600-006-0179-2

  日期：2006.7

  A preparative semi-synthetic method was developed to prepare 20S-protopanaxadiol 20-O-β-Dglucopyranoside (1), a metabolite of Panax ginseng glycosides. The 20-O-•-D-glucopyranosides of 20S-hydroxydammar-24-en-3,12-dione, 3β,20S-dihydroxydammar-24-en-12-one, and 3β,12α, 20S-trihydroxydammar-24-ene were synthesized for the first time.

  开发了一种准备性的半合成方法，以制备人参苷的代谢产物20S-原人参二醇20-O-β-D-葡萄糖苷 (1)。首次合成了20S-羟基达马烯-24-酮-3,12-二酮、3β,20S-二羟基达马烯-24-酮和3β,12α,20S-三羟基达马烯-24-烯的20-O-β-D-葡萄糖苷。
• Semisynthetic analogues of ginsenosides, glycosides from ginseng
  作者：Lyubov N. Atopkina、Vladimir A. Denisenko、Nina I. Uvarova、Georgi B. Elyakov

  DOI：10.1016/0008-6215(88)85045-6

  日期：1988.6

  Abstract Glycosylation of the dammar-24-ene-3,12β,20( S )-triols with 2,3,4,6-tetra- O -acetyl-α- d -glucopyranosyl bromide ( A ) in the presence of silver oxide in dichloro-methane gives a mixture of the acetylated 3-, 12-, 20-, 3,12-di-, and 3,20-di- O -β- d -glucopyranosyl derivatives in a total yield of 83–84.5%. Under similar conditions, the 3- O -acetyl derivatives of dammar-24-ene-3,12β,20(

  摘要在氧化银存在的条件下，将dammar-24-ene-3,12β，20（S）-三醇与2,3,4,6-四-O-乙酰基-α-d-吡喃葡萄糖基溴化物（A）糖基化二氯甲烷中得到乙酰化的3-，12-，20-，3,12-二-和3,20-二-O-β-d-吡喃葡萄糖基衍生物的混合物，总产率为83-84.5％ 。在相似的条件下，达玛-24-烯-3,12β，20（S）-三醇的3-O-乙酰基衍生物得到12-和20-O-β-d-吡喃葡萄糖基衍生物的混合物。在氰化汞存在的条件下，在硝化甲烷中，将异黄酮三醇[dammar-24-ene-3α，12β，20（S）-三醇]与糖基溴化物A和3,4,6-三-O-乙酰基-β缩合-在2,4存在下的d-吡喃葡萄糖1,2-（原乙酸叔丁酯）