demethylbelamcandaquinone B | 1339815-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: demethylbelamcandaquinone B
• 英文别名: labisiaquinone A；2-[2,4-dihydroxy-6-[(Z)-pentadec-10-enyl]phenyl]-5-methoxy-3-[(Z)-pentadec-10-enyl]cyclohexa-2,5-diene-1,4-dione
• CAS: 1339815-85-8
• 化学式: C₄₃H₆₆O₅
• 分子量: 662.994
• InChiKey: KNBYYMABMOPODL-MIMPSMLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15
• 重原子数：
  48
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  demethylbelamcandaquinone B 在 吡啶 、 二甲基硫 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Alkenylresorcinols and cytotoxic activity of the constituents isolated from Labisia pumila

  摘要：

  Phytochemical investigation on the leaves of Labisia pumila (Myrsinaceae), an important medicinal herb in Malaysia, has led to the isolation of 1-O-methyl-6-acetoxy-5-(pentadec-10Z-enyl)resorcinol (1), labisiaquinone A (2) and labisiaquinone B (3). Along with these, 16 known compounds including 1-O-methyl-6-acetoxy-5-pentadecylresorcinol (4), 5-(pentadec-10Z-enyl)resorcinol (5), 5-(pentadecyl)resorcinol (6), (-)-loliolide (7), stigmasterol (8), 4-hydroxyphenylethylamine (9), 3,4,5-trihydroxybenzoic acid (10), 3,4-dihydroxybenzoic acid (11), (+)-catechin (12), (-)-epicatechin (13), kaempferol-3-O-alpha-rhamnopyranosyl-7-O-beta-glycopyranoside (14), kaempferol-4'-O-beta-glycopyranoside (15), quercetin-3-O-alpha-rhamnopyranoside (16), kaempferol-3-O-alpha-rhamnopyranoside (17), (9Z,12Z)-octadeca-9,12-dienoic acid (18) and stigmasterol-3-O-beta-glycopyranoside (19) were also isolated. The structures of these compounds were established on the basis of 1D and 2D NMR spectroscopy techniques (H-1, C-13, COSY, HSQC, NOESY and HMBC experiments), mass spectrometry and chemical derivatization. Among the constituents tested 1 and 4 exhibited strongest cytotoxic activity against the PC3, HCT116 and MCF-7 cell lines (IC50 values <= 10 mu M), and they showed selectivity towards the first two-cell lines relative to the last one. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.04.008

文献信息

• Alkyl phenols and saponins from the roots of Labisia pumila (Kacip Fatimah)
  作者：Zulfiqar Ali、Ikhlas A. Khan

  DOI：10.1016/j.phytochem.2011.06.014

  日期：2011.11

  Recently, there is a remarkable boom in the sales of Labisia pumila (Kacip Fatimah) in the Malaysian market, as an extract of the plant is used to gain energy and libido as well as to treat many other ailments. A chemical analysis of its roots was undertaken and three metabolites, demethylbelamcandaquinone B (1), fatimahol (2), and dexyloprimulanin (3) together with 21 known compounds including epoxyoleanane glycosides, alkenated phenolics, cerebroside, glycerogalactolipids, and lipids were isolated and identified. Structure elucidation was achieved by spectroscopic and chemical studies. The MeOH extract of KF and compounds 12 and 13 exhibited moderate in vitro antibacterial activity. (C) 2011 Elsevier Ltd. All rights reserved.