16α-hydroxy protobassic acid

• 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: 16α-hydroxy protobassic acid
• 英文别名: 16α-hydroxyprotobassic acid；16α-hydroxyprotobassicacid；2β,3β,6β,16α,23-pentahydroxyolean-12-en-28-oic acid；(4aR,5R,6aR,6aS,6bR,8R,8aR,9R,10R,11S,12aR,14bS)-5,8,10,11-tetrahydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• 化学式: C₃₀H₄₈O₇
• 分子量: 520.707
• InChiKey: KKWGQGDQEJNURS-BYZWDMGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  138
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-O-β-D-glucuronopyranosyl-16α-hydroxyprotobassic acid 28-O-α-L-rhamnopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-xylopyranoside 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 16α-hydroxy protobassic acid
  参考文献：
  名称：

  Cytotoxic and antioxidant triterpene saponins from Butyrospermum parkii (Sapotaceae)

  摘要：

  Three new triterpenoid saponins, elucidated as 3-O-beta-D-glucopyranosyloleanolic acid 28-O-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranoside (parkioside A. 1), 3-O-[beta-D-apifuranosyl-(1 -> 3)-beta-D-glucopyranosylloleanolic acid 28-O-[beta-D-apifuranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-[alpha-L-rhamnopyranosyl-(1 -> 3)]-alpha-L-rhamnoPyranosyl-(1 -> 2)beta-D-xyloPyranoside (parkioside B, 2) and 3-O-beta-D-glucuronopyranosyl-16 alpha-hydroxyprotobassic acid 28-O-alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranoside (parkioside B, 3), were isolated from the n-BuOH extract of the root bark of Butyrosperrnum parkii, along with the known 3-O-beta-D-glucopyranosyloleanolic acid (androseptoside A). The structures of the isolated compounds were established on the basis of chemical and spectroscopic methods, mainly 1D and 2D NMR data and mass spectrometry. The new compounds were tested for both radical scavenging and cytotoxic activities. Compound 2 showed cytotoxic activity against A375 and T98G cell lines, with IC50 values of 2.74 and 2.93 mu M, respectively. Furthermore, it showed an antioxidant activity comparable to that of Trolox or butylated hydroxytoluene (BHT), used as controls, against 2,2-dipheny1-1-picryl hydrazyl (DPPH), 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), oxygen and nitric oxide radicals. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.014

文献信息

• ACCELERATOR FOR INITIAL INSULIN SECRETION
  申请人：Use-Techno Corporation

  公开号：EP1674089A1

  公开（公告）日：2006-06-28

  The present invention provides an early insulin secretion stimulator consisting of a triterpene represented by the following general formula (1) and/or a triterpene represented by the following general formula (2). [where R1 represents COOH, etc., R11 and R12 represent CH2OH, etc., X1 represents hydrogen or OH and X11, X12, X21 and X22 represent OH, etc.]

  本发明提供了一种早期胰岛素分泌刺激剂，由以下通式（1）代表的三萜和/或以下通式（2）代表的三萜组成。 [其中 R1 代表 COOH 等，R11 和 R12 代表 CH2OH 等，X1 代表氢或 OH，X11、X12、X21 和 X22 代表 OH 等。］
• Triterpene glycosides and other polar constituents of shea (Vitellaria paradoxa) kernels and their bioactivities
  作者：Jie Zhang、Masahiro Kurita、Takuro Shinozaki、Motohiko Ukiya、Ken Yasukawa、Naoto Shimizu、Harukuni Tokuda、Eliot T. Masters、Momoko Akihisa、Toshihiro Akihisa

  DOI：10.1016/j.phytochem.2014.09.017

  日期：2014.12

  The MeOH extract of defatted shea (Vitellaria paradoxa; Sapotaceae) kernels was investigated for its constituents, and fifteen oleanane-type triterpene acids and glycosides, two steroid glucosides, two pentane-2,4-diol glucosides, seven phenolic compounds, and three sugars, were isolated. The structures of five triterpene glycosides were elucidated on the basis of spectroscopic and chemical methods. Upon evaluation of the bioactivity of the isolated compounds, it was found that some or most of the compounds have potent or moderate inhibitory activities against the following: melanogenesis in B16 melanoma cells induced by alpha-melanocyte-stimulating hormone (alpha-MSH); generation of 1,1-dipheny1-2-picrylhydrazyl (DPPH) radicals, against Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-teradecanoylphorbol 13-acetate (TPA) in Rail cells; t TPA-induced inflammation in mice, and proliferation of one or more of HL-60, A549, AZ521, and SK-BR-3 human cancer cell lines, respectively. Western blot analysis established that paradoxoside E inhibits melanogenesis by regulation of expression of microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein-1 (TRP-1) and TRP-2. In addition, tieghemelin A was demonstrated to exhibit cytotoxic activity against A549 cells (IC50 13.5 mu M) mainly due to induction of apoptosis by flow cytometry. The extract of defatted shea kernels and its constituents may be, therefore, valuable as potential antioxidant, anti-inflammatory, skin-whitening, chemopreventive, and anticancer agents. (c) 2014 Elsevier Ltd. All rights reserved.
• Insulin secretion potentiator
  申请人：Matsuyama Futoshi

  公开号：US20050143464A1

  公开（公告）日：2005-06-30

  The present invention provides early insulin secretion stimulators consisting of triterpenes represented by the following general formula (1) and/or triterpenes represented by the following general formula (2). [where R 1 represents COOH, etc., R 11 and R 12 represent CH 2 OH, etc., X 1 represents hydrogen or OH and X 11 , X 12 , X 21 and X 22 represent OH, etc.]
• [EN] GLUCONEOGENESIS INHIBITING AGENT<br/>[FR] AGENTS D'INHIBITION DE LA GLUCONEOGENESE
  申请人：USE TECHNO CORP

  公开号：WO2006054370A1

  公开（公告）日：2006-05-26

  [EN] The present invention provides a gluconeogenesis inhibiting agent containing as an active ingredient corosolic acid, an analogous compound of corosolic acid, or a pharmaceutically acceptable salt thereof.
  [FR] La présente invention concerne un agent d'inhibition de la gluconéogenèse, contenant en tant qu'ingrédient actif de l'acide corosolique, un analogue de l'acide corosolique ou l'un de leurs sels pharmaceutiquement acceptables.
• [EN] TERPENE, METHOD FOR DETERMINING ITS BLOOD CONCENTRATION, AND METHOD FOR ANALYZING ITS PHARMACOKINETICS<br/>[FR] TERPENE, PROCEDE DE DETERMINATION DE SA CONCENTRATION SANGUINE, ET PROCEDE POUR L'ANALYSE DES SA PHARMACOCINETIQUE
  申请人：USE TECHNO CORP

  公开号：WO2006064583A1

  公开（公告）日：2006-06-22

  [EN] [Problem] To provide a method for determining precisely blood concentration of a terpene present in blood at a low concentration, a method for analyzing pharmacokinetics of a terpene using the method for determining blood concentration of a terpene, and a terpene having pharmacokinetics which is analyzed using the method for analyzing pharmacokinetics of a terpene. [Solution] The method for determining blood concentration of a terpene comprises detecting the terpene in blood by a mass spectrometer to determine blood concentration of the terpene.
  [FR] La présente invention vise à fournir un procédé pour la détermination précise de la concentration sanguine d'un terpène présent dans le sang à une faible concentration, un procédé pour l'analyse de la pharmacocinétique d'un terpène mettant en oeuvre le procédé de détermination de la concentration sanguine d'un terpène, et un terpène présentant une pharmacocinétique qui est analysée par le procédé mettant en oeuvre le procédé d'analyse de la pharmacocinétique d'un terpène. La présente invention a trait à un procédé pour la détermination de la concentration sanguine d'un terpène comprenant la détection du terpène dans le sang par une spectrométrie de masse en vue de déterminer la concentration sanguine du terpène.