3β-acetoxy-30-nor-lupan-20-one | 55870-41-2

• 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: 3β-acetoxy-30-nor-lupan-20-one
• 英文别名: [(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-acetyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
• CAS: 55870-41-2
• 化学式: C₃₁H₅₀O₃
• 分子量: 470.736
• InChiKey: CACUJZIALZRTTC-VOAUEXJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-30-nor-lupan-20-one 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 Acetic acid (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-ethoxycarbonyloxycarbonyl-3a,5a,5b,8,8,11a-hexamethyl-icosahydro-cyclopenta[a]chrysen-9-yl ester
  参考文献：
  名称：

  Preparation of 29-acetoxy-30-norlupan-20-one derivatives with the substituted ring C

  摘要：

  DOI：

  10.1135/cccc19782190
• 作为产物：
  描述：

  19α-Chlor-18β-oleanan-3β-ol 在 chromium(VI) oxide 、 乙醇 、 溶剂黄146 作用下， 生成 3β-acetoxy-30-nor-lupan-20-one
  参考文献：
  名称：

  Duerden et al., Journal of the Chemical Society, 1939, p. 322,324

  摘要：

  DOI：

文献信息

• Design and synthesis of new lupeol derivatives and their <i>α</i>-glucosidase inhibitory and cytotoxic activities
  作者：Hoang-Vinh-Truong Phan、Thuc-Huy Duong、Duc-Dung Pham、Hoang-Anh Pham、Van-Kieu Nguyen、Thi-Phuong Nguyen、Huu-Hung Nguyen、Ngoc-Hong Nguyen、Pornpat Sam-ang、Kiettipum Phontree、Jirapast Sichaem

  DOI：10.1080/14786419.2020.1758095

  日期：2022.1.2

  were designed, synthesised and evaluated for their α-glucosidase inhibitory and cytotoxic activities. Among synthetic derivatives, lupeol analogues 2b and 2e containing a benzylidene chain exhibited the best activity against α-glucosidase and superior to the positive agent with the IC50 values of 29.4 ± 1.33 and 20.1 ± 0.91 μM, respectively. Lupeol analogues 2d and 3a showed weak cytotoxicity against

  摘要 一系列羽扇豆醇衍生物的2，图2A-2F，图2a-2H，3A-3E和4A-4B设计，合成并评价了它们的α葡萄糖苷酶抑制和细胞毒活性。在合成衍生物中，含有亚苄基链的羽扇豆醇类似物2b和2e对α-葡萄糖苷酶的活性最好，并且优于阳性试剂，IC 50值分别为 29.4 ± 1.33 和 20.1 ± 0.91 μM。Lupeol 类似物2d和3a对 K562 细胞系显示出弱的细胞毒性，IC 50 值分别为 76.6 ± 2.40 和 94.4 ± 1.51 μM。
• Koelpinin-A, B and C — three triterpenoids from Koelpinia linearis
  作者：Summon Koul、T.K. Razdan、C.S. Andotra、A.K. Kalla、S. Koul、S.C. Taneja、K.L. Dhar

  DOI：10.1016/s0031-9422(99)00490-2

  日期：2000.1

  beta-acetoxy-28-nor-lup-12,17-dien-16 alpha-ol and 28-nor-lup-12,17-dien-3 beta-ol-16-one, respectively, together with 30-nor-lup-3 beta-ol-20-one, taraxeryl acetate and germanicol, were isolated, from the aerial parts of Koelpinia linearis. 13C-NMR shifts were assigned after performing APT and DEPT experiments.

  三种新的三萜类化合物，命名为 koelpinin-A、B 和 C，特征为 28-nor-lup-12,17-dien-3 beta,16 alpha-diol,3 beta-acetoxy-28-nor-lup-12,17 -dien-16 alpha-ol 和 28-nor-lup-12,17-dien-3 beta-ol-16-one 分别与 30-nor-lup-3 beta-ol-20-one 一起，醋酸蒲公英和germanicol，是从Koelpinia linearis 的地上部分分离出来的。在进行 APT 和 DEPT 实验后指定了 13C-NMR 位移。
• Oxyfunctionalization Products of Terpenoids with Dimethyldioxirane and Their Biological Activity
  作者：Shoujiro Ogawa、Keiji Hosoi、Noriaki Ikeda、Mitsuko Makino、Yasuo Fujimoto、Takashi Iida

  DOI：10.1248/cpb.55.247

  日期：——

  Oxyfunctionalization of the bioactive terpenoids, ursolic acid acetate (1), oleanolic acid acetate (5), lupeol acetate (12), and kaurenic acid (17), with dimethyldioxirane (DMDO) was investigated. Treatment of the terpenoids with DMDO under mild conditions afforded a variety of oxidation and oxydegradation products to yield naturally occurring and/or novel compounds in one step. After chromatographic separation, the structures of the individual isolated products were determined using spectroscopic methods including several homonuclear (1H–1H) and heteronuclear (1H–13C) shift-correlated 2D-NMR techniques. The inhibitory activity of the terpenoid derivatives against α-glucosidase was investigated and compounds 1, 3, 7, and 9 were found to exhibit potent activity.

  研究人员用二甲基二氧环己烷（DMDO）对具有生物活性的萜类化合物熊果酸乙酸酯（1）、齐墩果酸乙酸酯（5）、羽扇豆醇乙酸酯（12）和高瑞香酸（17）进行了氧化官能化处理。在温和的条件下，用二甲基二氧环己烷处理萜类化合物，可产生多种氧化和氧降解产物，从而一步生成天然和/或新型化合物。色谱分离后，利用光谱方法（包括几种同核（1H-1H）和异核（1H-13C）位移相关的二维核磁共振技术）确定了各个分离产物的结构。研究了萜类衍生物对 α-葡萄糖苷酶的抑制活性，发现化合物 1、3、7 和 9 具有很强的活性。
• Synthesis and structure of an acetylene derivative of lupeol
  作者：O. B. Kazakova、N. I. Medvedeva、K. Yu. Suponitskii

  DOI：10.1007/s10600-011-9945-x

  日期：2011.7

  The synthesis and x-ray crystal structure of 3-acetoxy-29-norlup-20(30)-yne were carried out.

  进行了3-乙酰氧基-29-norlup-20(30)-yne的合成和X射线晶体结构。
• Isolation of 19 α‐H‐Lupeol from Maclura pomifera
  作者：J.E. Gearien、Michael Klein

  DOI：10.1002/jps.2600640121

  日期：1975.1

  A reinvestigation of the constituents of the Osage orange (maclura pomifera) yielded, in addition to the previously reported triterpenses (lupeol, butyrospermol, and lupan-3beta,20-diol), the pigments osajin and pomiferin, and a previously unreported constituent. The structure of this new compound was investigated. On the basis of spectroscopic and chemical data, it appeared to be an epimer of lupeol

  除先前报道的三萜类化合物（三萜醇，丁草酚和卢潘3β，20-二醇），颜料osajin和pomiferin以及先前未报道的成分外，对欧塞奇橙（maclura pomifera）的成分进行了重新研究。研究了这种新化合物的结构。根据光谱和化学数据，它似乎是羽扇豆酚的差向异构体，被称为19α-H-羽扇豆酚。