3-O-β-D-glucopyranosyl-(22E,24R)-ergosta-7,22-dien-5α,6β-diol | 140447-21-8

• 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: 3-O-β-D-glucopyranosyl-(22E,24R)-ergosta-7,22-dien-5α,6β-diol
• 英文别名: 3-O-β-D-glucopyranosyl-ergosta-7,22-dien-5α,6β-diol；3β-O-glucopyranosyl-5α,6β,-dihydroxyergosta-7,22-diene；3β-O-glucopyranosyl-5α,6β-dihydroxy-ergosta-7,22E-diene；tuberoside；(2R,3R,4S,5S,6R)-2-[[(3S,5R,6R,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-5,6-dihydroxy-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 140447-21-8
• 化学式: C₃₄H₅₆O₈
• 分子量: 592.814
• InChiKey: OHZYISZWOVEBCJ-ATLCLBDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-O-β-D-glucopyranosyl-(22E,24R)-ergosta-7,22-dien-5α,6β-diol 在 吡啶 作用下， 以9.3 mg的产率得到
  参考文献：
  名称：

  A novel sterol from Chinese truffles Tuber indicum

  摘要：

  From the fruiting bodies of Ascomycetes Tuber indicum, a new steroidal glucoside with polyhydroxy ergosterol nucleus, tuberoside (2), has been isolated along with additional four known ergosterol derivatives, (22E, 24R)-ergosta-7, 22-dien-3beta, 5alpha, 6beta-triol (1), 5alpha, 8alpha-epidioxy-(22E, 24R)-ergosta-6, 22-dien-3beta-ol (3), (22E, 24R)-ergosta-5, 22-dien-3beta-ol (4), and (22E, 24R)-ergosta-4, 6, 8(14), 22-tetraen-3-one (5). The structure of new compound was established as 3-O-beta-D-glucopyranosyl-(22E, 24R)-ergosta-7, 22-dien-5alpha, 6beta-diol (2) on the basis of chemical and spectroscopic means ((1)H NMR, (13)C NMR, HMQC, HMBC, MS, and IR). This is the first example of isolation of a polyhydroxylated ergosterol glucoside from higher fungi in nature.

  DOI：

  10.1016/s0039-128x(01)00105-2

文献信息

• A novel sterol from Chinese truffles Tuber indicum
  作者：G Jinming

  DOI：10.1016/s0039-128x(01)00105-2

  日期：2001.10

  From the fruiting bodies of Ascomycetes Tuber indicum, a new steroidal glucoside with polyhydroxy ergosterol nucleus, tuberoside (2), has been isolated along with additional four known ergosterol derivatives, (22E, 24R)-ergosta-7, 22-dien-3beta, 5alpha, 6beta-triol (1), 5alpha, 8alpha-epidioxy-(22E, 24R)-ergosta-6, 22-dien-3beta-ol (3), (22E, 24R)-ergosta-5, 22-dien-3beta-ol (4), and (22E, 24R)-ergosta-4, 6, 8(14), 22-tetraen-3-one (5). The structure of new compound was established as 3-O-beta-D-glucopyranosyl-(22E, 24R)-ergosta-7, 22-dien-5alpha, 6beta-diol (2) on the basis of chemical and spectroscopic means ((1)H NMR, (13)C NMR, HMQC, HMBC, MS, and IR). This is the first example of isolation of a polyhydroxylated ergosterol glucoside from higher fungi in nature.