3,30-dioxo-lup-20(29)en-28-oic 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: 3,30-dioxo-lup-20(29)en-28-oic acid
• 英文别名: betulonic acid acrylaldehyde；30-oxobetulonic acid；(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(3-oxoprop-1-en-2-yl)-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
• 化学式: C₃₀H₄₄O₄
• 分子量: 468.677
• InChiKey: NPPZUHIGLUMVOX-SVAFSPIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  白桦脂酸 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 pyridinium chlorochromate 作用下， 以 氯仿 为溶剂， 反应 3.17h， 生成 3,30-dioxo-lup-20(29)en-28-oic acid
  参考文献：
  名称：

  Bioactive polar triterpenoids from Melilotus messanensis

  摘要：

  In addition to the known 3-oxoplatanic acid, melilotigenin and soyasapogenol E, two new lupane (messagenic acids F, G), two nor-lupane triterpenic acids (messagenic acids H, I), and three new oleanane triterpenes (melilotigenins B-D) were isolated and characterized from the polar bioactive fractions of Melilotus messanensis. The synthesis of messagenic acids D, F, G, betulonic acid and 3,29-dioxolup-20(30)-en-28-oic acid has been carried out from betulinic acid. These compounds exhibited clear selectivity (parameters and species) over germination and growth of monocotyledon species with average of inhibition of - 50% on the germination of Hordeum vulgare, and average of stimulation of 30% on the germination of Allium cepa. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00167-8

文献信息

• Lupane derivatives: Design, isolation, synthesis and evaluation of antiplasmodial activity against Plasmodium falciparum 3D7 strain
  作者：Pierre Yemback、Kenneth O. Eyong、Noella M. Efange、Michael HK. Kamdem、Derek T. Ndinteh、Patricia O. Odumosu、Gabriel N. Folefoc、Lawrence Ayong、Thomas Werner

  DOI：10.1016/j.phytol.2023.06.009

  日期：2023.10

  (Pierre); olean-12-en-3β-decanoate (3), 3-β-trans cinnamoyloxylup-20(29)-ene (4), 3β-amyrin acetate (5), taraxerol (6), betulonic acid (7), β-sitosterol (8), betulinic acid (9), 3β-(trans-p-Coumaroyl)oxylup-20(29)-en-28-oïc acid (10) and screened alongside Betuline (11) and oleanolic acid (12). The favorable compounds 7 and 10 with 100 % growth inhibition on P. falciparum 3D7 strain together with compounds

  为了寻找对抗疟疾的先导化合物，通过针对恶性疟原虫的酶标靶甘油醛-3-磷酸脱氢酶 (P f GAPDH) 的分子对接研究，筛选了来自喀麦隆天然产物库 (CANAPL)的化合物。对接命中包括羽扇豆醇肉桂酸酯 ( 1 ) 和齐墩果烷肉桂酸酯 ( 2 )。从Baillonella toxisperma (Pierre)中分离出与( 1 )和( 2 )结构相似的三萜类化合物；齐墩果-12-en-3β-癸酸酯 ( 3 )、3-β-反式肉桂酰氧基lup-20(29)-烯 ( 4 ) 、 3β-香树脂醇乙酸酯 ( 5)、蒲公英醇 ( 6 )、桦木酮酸 ( 7 )、β-谷甾醇 ( 8 )、桦木酸 ( 9 )、3β-(反式对香豆酰基)oxylup-20(29)-en-28-oïc 酸 ( 10 ）并与桦木碱（11 ）和齐墩果酸（12）一起筛选。对恶性疟原虫3D7 菌株具有 100% 生长抑制作用的有利化合物7和10与化合物
• Microbial transformations of betulinic and betulonic acids
  作者：Animesh Goswami、Zhiwei Guo、Thomas P. Tully、Frank A. Rinaldi、Xiaohua Stella Huang、Jacob J. Swidorski、Alicia Regueiro-Ren

  DOI：10.1016/j.molcatb.2015.04.012

  日期：2015.7

  Enzymatic transformation of betulinic acid by growing cells of microorganisms provided several hydroxylated and oxidized products. Bacillus megaterium SC16644 gave 7 beta,15 alpha-dihydroxybetulinic acid, 7 beta,15 alpha-dihydroxybetulonic acid, and a new compound 7 beta,15 alpha,23-trihydroxybetulinic acid [3 beta,7 beta,15 alpha,23-tetrahydroxy-lup-20(29)en-28-oic acid]. Another strain of B. megaterium SC6394 produced 30-oxobetulonic acid, and a mixture of 30-hydroxybetulonic acid and a new compound 7 beta-hydroxy-30-oxobetulonic acid [7 beta-hydroxy-3,30-dioxo-lup-20(29)en-28-oic acid]. Three products were obtained from the biotransformation of betulinic acid by Streptomyces frag-ilis SC16401: 7 beta-hydroxybetulonic acid, and two new compounds 2 alpha,7 beta-dihydroxybetulinic acid [2 alpha,3 beta,7 beta-trihydroxy-lup-20(29)en-28-oic acid] and 2-oxo-7 beta-hydroxy-betulinic acid [2-oxo-3 beta,7 beta-dihydroxy-lup-20(29)en-28-oic acid]. Cunninghamella elegans SC16025 gave 25-hydroxybetulinic acid from betulinic acid. Oxidation of betulinic acid by Aspergillus terreus SC16513 led to two A-ring fission products: 4-hydroxy-3,4-seco-lup-20(29)-en-3,2b-dioic acid and 3,4-seco-lup-20(29), 4(23)-dien-3,28-dioic acid. B. megaterium SC16644 catalyzed transformation of betulonic acid provided 7 beta-hydroxybetulonic acid, 7 beta,15 alpha-dihydroxybetulonic acid, and a new compound 7 beta,15 alpha,30-trihydroxybetulonic acid [3-oxo-7 beta,15 alpha,30-trihydroxy-lup-20(29)en-28-oic acid]. (C) 2015 Elsevier B.V. All rights reserved.
• Bioactive polar triterpenoids from Melilotus messanensis
  作者：Francisco A. Macías、Ana M. Simonet、Juan Carlos G. Galindo、Pedro C. Pacheco、Jose A. Sánchez

  DOI：10.1016/s0031-9422(98)00167-8

  日期：1998.10

  In addition to the known 3-oxoplatanic acid, melilotigenin and soyasapogenol E, two new lupane (messagenic acids F, G), two nor-lupane triterpenic acids (messagenic acids H, I), and three new oleanane triterpenes (melilotigenins B-D) were isolated and characterized from the polar bioactive fractions of Melilotus messanensis. The synthesis of messagenic acids D, F, G, betulonic acid and 3,29-dioxolup-20(30)-en-28-oic acid has been carried out from betulinic acid. These compounds exhibited clear selectivity (parameters and species) over germination and growth of monocotyledon species with average of inhibition of - 50% on the germination of Hordeum vulgare, and average of stimulation of 30% on the germination of Allium cepa. (C) 1998 Elsevier Science Ltd. All rights reserved.