刺五加叶中 | 36284-77-2

• 物质功能分类: 生物化工 - 提取物
• 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
• 中文名称: 刺五加叶中
• 中文别名: 常春藤皂甙B
• 英文名称: hederasaponin B
• 英文别名: hederacoside B；eleutheroside M；[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 36284-77-2
• 化学式: C₅₉H₉₆O₂₅
• 分子量: 1205.4
• InChiKey: NVSLBOBPSCMMSO-BVLVEXITSA-N

物化性质

• 熔点：
  223-226℃
• 密度：
  1.46
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  84
• 可旋转键数：
  13
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  393
• 氢给体数：
  14
• 氢受体数：
  25

制备方法与用途

刺五加是多年生落叶植物，属于五加科，与人参同属。刺五加叶皂苷（ASS）是从刺五加叶片中提取的一种含有16种皂苷成分的总皂苷，其含量为18.59%，其中13种属于三萜皂苷。此外，刺五加叶片中的黄酮类化合物含量较高，可达37.25%。刺五加多糖在9月份含量较高。

刺五加叶中富含活性成分，具有以下作用：

• 抗炎、抗菌
• 抗癌
• 抗应激

Hederasaponin B 是从常春藤（Hedera helix）中分离出的化合物，对肠道病毒71 (EV71) 的多种亚型表现出广谱抗病毒活性。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	ciwujianoside C4	114906-75-1	C61H98O26	1247.43

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  beta-常春藤素	β-hederin	35790-95-5	C41H66O11	734.968

反应信息

• 作为反应物：
  描述：

  刺五加叶中 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 2.0h， 以12 mg的产率得到beta-常春藤素
  参考文献：
  名称：

  Antiproliferative Triterpene Saponins from Trevesia palmata

  摘要：

  During the course of a study of plants of the family Araliaceae, antiproliferative activity was demonstrated by the crude saponin fraction of Trevesia palmata, After chromatographic purification, six near bisdesmosidic saponins (1-6), along with two known triterpenoid saponins, (7 and 8), were isolated. The structures of 1-6 were determined by H-1-H-1 correlation spectroscopy (COSY-DQF, 1D, TOCSY, 2D HOHAHA, 1D ROESY) and H-1-C-13 (HSQC, HMBC) spectroscopy. The antiproliferative activity of compounds 1-8 and of their prosapogenins (2a-7a) prepared by alkaline hydrolysis, was evaluated using three continuous culture cell lines.

  DOI：

  10.1021/np990231n
• 作为产物：
  描述：

  ciwujianoside C₄ 在 氢氧化钾 作用下， 反应 24.0h， 以26 mg的产率得到刺五加叶中
  参考文献：
  名称：

  Shao, Chun-Jie; Kasai, Ryoji; Xu, Jing-Da, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 2, p. 601 - 608

  摘要：

  DOI：

文献信息

• Synthesis, biological evaluation and structure-activity relationship studies of hederacolchiside E and its derivatives as potential anti-Alzheimer agents
  作者：Hui-ning Li、Yang Liu、Zuo-peng Zhang、Zhi-peng Wang、Jing-zheng Hao、Feng-ran Li、Zhan-fang Fan、Li-bo Zou、Mao-sheng Cheng

  DOI：10.1016/j.ejmech.2017.11.040

  日期：2018.1

  Inspired by the previously reported neuroprotective activity of hederacolchiside E (1), we synthesized hederacolchiside E for the first time along with eleven of its derivatives. The neuroprotective effects of these compounds were further evaluated against H2O2- and A beta(1-42)-induced injury using cell-based assays. The derivatives showed obvious differences in activity due to structural variations, and two of them exhibited better neuroprotective effects than 1 in the A beta(1-42)-induced injury model. Compound 7 was the most active derivative and had a relatively simple chemical structure. Moreover, 1 and 7 can significantly reduce the release of lactate dehydrogenase (LDH), level of intracellular reactive oxygen species (ROS) and extent of malondialdehyde (MDA) increase resulting from A beta(1-42) treatment, which demonstrated that these kinds of compounds show neuroprotective effects in Alzheimer's disease (AD) models via modulating oxidative stress. Compound 7 could be used as promising lead for the development of a new type of neuroprotective agent against AD. (C) 2017 Elsevier Masson SAS. All rights reserved.
• OLEANANE TRITERPENE SAPONIN COMPOUNDS WHICH ARE EFFECTIVE ON TREATMENT OF DEMENTIA AND MILD COGNITIVE IMPAIRMENT(MCI), AND IMPROVEMENT OF COGNITIVE FUNCTION
  申请人：SK CHEMICALS CO., LTD.

  公开号：EP2077827A1

  公开（公告）日：2009-07-15
• OLEANANE TRITERPENE SAPONIN COMPOUNDS WHICH ARE EFFECTIVE ON TREATMENT OF DEMENTIA AND MILD COGNITIVE IMPAIRMENT (MCI) AND IMPROVEMENT OF COGNITIVE FUNCTION
  申请人：Kim Bong Cheol

  公开号：US20100190968A1

  公开（公告）日：2010-07-29

  The present invention relates to the use of oleanane-type triterpene saponin compounds, which are effective for improving memory and learning ability, as an effective ingredient of drugs for the treatment and prevention of dementia and mild cognitive impairment and health foods for the improvement of brain functions including cognitive function.
• US6967194B1
  申请人：——

  公开号：US6967194B1

  公开（公告）日：2005-11-22
• US7354608B1
  申请人：——

  公开号：US7354608B1

  公开（公告）日：2008-04-08