hebevinoside III | 89203-39-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: hebevinoside III
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3S,7S,8R,9S,10S,13R,14S,16S,17R)-7-hydroxy-4,4,9,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-16-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 89203-39-4
• 化学式: C₄₃H₇₀O₁₃
• 分子量: 795.021
• InChiKey: ZSGIZQTTWRMUOQ-ZSFDVCMRSA-N

物化性质

• 沸点：
  850.8±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  56
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  hebevinoside III 、 碘甲烷 在 sodium hydride 作用下， 生成
  参考文献：
  名称：

  蘑菇中的新的有毒代谢物，酒豆。I. hebevinosides I，II，III，IV和V的结构。

  摘要：

  新发现的毒蘑菇 Hebeloma vinosophyllum 中的代谢物 hebevinosides I, II, III, IV 和 V 的结构被推测为：3β, 16β-二羟基-7β-甲氧基-南瓜烯-5, 24-烯-3-O-β-D-木糖吡喃糖苷-16-O-(6-O-乙酰)-β-D-葡萄糖吡喃糖苷 (1)，3β, 7β, 16β-三羟基-南瓜烯-5, 24-烯-3-O-(4-O-乙酰)-β-D-木糖吡喃糖苷-16-O-(6-O-乙酰)-β-D-葡萄糖吡喃糖苷 (22)，3β, 7β, 16β-三羟基-南瓜烯-5, 24-烯-3-O-β-D-木糖吡喃糖苷-16-O-(6-O-乙酰)-β-D-葡萄糖吡喃糖苷 (24)，3β, 16β-二羟基-7β-甲氧基-南瓜烯-5, 24-烯-3-O-β-D-木糖吡喃糖苷 (16)，以及3β, 16β-二羟基-7β-甲氧基-南瓜烯-5, 24-烯-3-O-(4-O-乙酰)-β-D-木糖吡喃糖苷-16-O-(6-O-乙酰)-β-D-葡萄糖吡喃糖苷 (27)。这些推测基于化学和光谱证据，以及通过酶解得到的乙氧基 hebevinogenin (20) 的 X 射线晶体结构分析。研究证明，hebevinosides I, II, III 和 V 是这种蘑菇的毒性成分。

  DOI：

  10.1248/cpb.34.88

文献信息

• New toxic metabolites from a mushroom, Hebeloma vinosophyllum. II. Isolation and structures of hebevinosides VI, VII, VIII, IX, X, and XI.
  作者：HARUHIRO FUJIMOTO、HIDEMI HAGIWARA、KUMIKO SUZUKI、MIKIO YAMAZAKI

  DOI：10.1248/cpb.35.2254

  日期：——

  Four new triterpene glycosides, hebevinosides VI, VII, VIII, and IX, whose common aglycone is 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene (hydroxyhebevinogenin), have been isolated from the acetone extract of a poisonous mushroom, Hebeloma vinosophyllum, and deduced to have the structures of 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-Ο-β-D-xylopyranoside-16-O-β-D-glucopyranoside, 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-Ο-β-D-xylopyranoside-16-Ο- (4, 6-di-Ο-acetyl) -β-D-glucopyranoside, 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-Ο- (4-Ο-acetyl) -β-D-xylopyranoside-16-Ο- (4, 6-di-Ο-acetyl) -β-D-glucopyranoside, and 3β, 7β, 16β-trihydroxycucurbita-3-Ο-β-D-xylopyranoside, respectively. Two new glycosides, hebevinosides X and XI, whose common aglycone is 3β, 16, β-dihydroxy-7β-methoxycucurbita-5, 24-diene (methoxyhebevinogenin), have also been isolated from the aqueous methanolic extract of the mushroom in addition to hebevinosides I, II, III, IV, and V previously reported, and deduced to be 3β, 16β-dihydroxy-7β-methoxycucurbita-5, 24-diene-3-Ο-β-D-xylopyranoside-16-Ο-β-D-glucopyranoside and 3β, 16β-dihydroxy-7β-methoxycucurbita-5, 24-diene-3-Ο-β-D-xylopyranoside-16-Ο- (4, 6-di-Ο-acetyl) -β-D-glucopyranoside, respectively. Among these eleven hebevinosides, I, IV, V, X, and XI, whose common aglycone is methoxyhebevinogenin, have been proved to be artifacts formed from the genuine metabolites III, IX, II, VI, and VII, whose common aglycone is hydroxyhebevinogenin, during extraction of the mushroom with aqueous methanol, respectively, and VIII, whose aglycone is hydroxyhebevinogenin, has also been proved to be a genuine metabolite of this mushroom. The relationship between the structure and toxicity of hebevinosides was also investigated.

  四种新三萜苷，hebevinosides VI、VII、VIII 和 IX，其共同的甾体核心为 3β, 7β, 16β-三羟基南瓜烯-5, 24-二烯（羟基hebevinogenin），已从一种有毒蘑菇 Hebeloma vinosophyllum 的丙酮提取物中分离出来，推测其结构为 3β, 7β, 16β-三羟基南瓜烯-5, 24-二烯-3-Ο-β-D-木糖吡喃糖苷-16-O-β-D-葡萄糖吡喃糖苷、3β, 7β, 16β-三羟基南瓜烯-5, 24-二烯-3-Ο-β-D-木糖吡喃糖苷-16-O-(4, 6-二-O-乙酰)-β-D-葡萄糖吡喃糖苷、3β, 7β, 16β-三羟基南瓜烯-5, 24-二烯-3-Ο-(4-O-乙酰)-β-D-木糖吡喃糖苷-16-O-(4, 6-二-O-乙酰)-β-D-葡萄糖吡喃糖苷，以及 3β, 7β, 16β-三羟基南瓜烯-3-Ο-β-D-木糖吡喃糖苷，各自为。另有两种新苷类，hebevinosides X 和 XI，其共同的甾体核心为 3β, 16β-二羟基-7β-甲氧基南瓜烯-5, 24-二烯（甲氧基hebevinogenin），也已从该蘑菇的水甲醇提取物中分离出来，此外还有之前报道的 hebevinosides I、II、III、IV 和 V，推测分别为 3β, 16β-二羟基-7β-甲氧基南瓜烯-5, 24-二烯-3-Ο-β-D-木糖吡喃糖苷-16-O-β-D-葡萄糖吡喃糖苷和 3β, 16β-二羟基-7β-甲氧基南瓜烯-5, 24-二烯-3-Ο-β-D-木糖吡喃糖苷-16-O-(4, 6-二-O-乙酰)-β-D-葡萄糖吡喃糖苷。在这十一种 hebevinosides 中，I、IV、V、X 和 XI，其共同甾体核心为甲氧基hebevinogenin，已被证明是从真正代谢物 III、IX、II、VI 和 VII（其共同甾体核心为羟基hebevinogenin）在用水甲醇提取该蘑菇的过程中形成的人工代谢物，而 VIII（其甾体核心为羟基hebevinogenin）也已被证明是真正的代谢物。还研究了 hebevinosides 的结构与毒性之间的关系。
• New toxic metabolites from a mushroom, Hebeloma vinosophyllum. I. Structures of Hebevinosides I, II, III, IV, and V.
  作者：HARUHIRO FUJIMOTO、KUMIKO SUZUKI、HIDEMI HAGIWARA、MIKIO YAMAZAKI

  DOI：10.1248/cpb.34.88

  日期：——

  The structures of hebevinosides I, II, III, IV, and V, new metabolites from a poisonous mushroom, Hebeloma vinosophyllum, were deduced to be 3β, 16β-dihydroxy-7β-methoxycucurbita-5, 24-diene-3-O-β-D-xylopyranoside-16-O-(6-O-acetyl)-β-D-glucopyranoside (1), 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-O-(4-O-acetyl)-β-D-xylopyranoside-16-O-(6-O-acetyl)-β-D-glucopyranoside (22), 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-O-β-D-xylopyranoside-16-O-(6-O-acetyl)-β-D-glucopyranoside (24), 3β, 16β-dihydroxy-7βmethoxycucurbita-5, 24-diene-3-O-β-D-xylopyranoside (16), and 3β, 16β-dihydroxy-7β-methoxycucurbita-5, 24-diene-3-O-(4-O-acetyl)-β-D-xylopyranoside-16-O-(6-O-acetyl)-β-D-glucopyranoside (27), respectively, on the basis of chemical and spectral evidence, as well as the structure determination by X-ray crystallographic analysis of ethoxyhebevinogenin (20), obtained by enzymatic hydrolysis of 16. Hebevinosides I, II, III, and V were proved to be toxic principles of this mushroom.

  新发现的毒蘑菇 Hebeloma vinosophyllum 中的代谢物 hebevinosides I, II, III, IV 和 V 的结构被推测为：3β, 16β-二羟基-7β-甲氧基-南瓜烯-5, 24-烯-3-O-β-D-木糖吡喃糖苷-16-O-(6-O-乙酰)-β-D-葡萄糖吡喃糖苷 (1)，3β, 7β, 16β-三羟基-南瓜烯-5, 24-烯-3-O-(4-O-乙酰)-β-D-木糖吡喃糖苷-16-O-(6-O-乙酰)-β-D-葡萄糖吡喃糖苷 (22)，3β, 7β, 16β-三羟基-南瓜烯-5, 24-烯-3-O-β-D-木糖吡喃糖苷-16-O-(6-O-乙酰)-β-D-葡萄糖吡喃糖苷 (24)，3β, 16β-二羟基-7β-甲氧基-南瓜烯-5, 24-烯-3-O-β-D-木糖吡喃糖苷 (16)，以及3β, 16β-二羟基-7β-甲氧基-南瓜烯-5, 24-烯-3-O-(4-O-乙酰)-β-D-木糖吡喃糖苷-16-O-(6-O-乙酰)-β-D-葡萄糖吡喃糖苷 (27)。这些推测基于化学和光谱证据，以及通过酶解得到的乙氧基 hebevinogenin (20) 的 X 射线晶体结构分析。研究证明，hebevinosides I, II, III 和 V 是这种蘑菇的毒性成分。