3-oxo-ent-13-epi-manoyl oxide | 29461-31-2

• 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-oxo-ent-13-epi-manoyl oxide
• 英文别名: ent-13-epi-manoyl oxide-3-one；ribenone；ent-3-oxo-13-epi-manoyl oxide；ent-8,13-β-Epoxy-14-labden-3-on；(3R,4aS,6aS,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-1,2,5,6,6a,9,10,10b-octahydrobenzo[f]chromen-8-one
• CAS: 29461-31-2
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: JICALWDNUXLSSY-OPTDIUSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-oxo-ent-13-epi-manoyl oxide 在 sodium tetrahydroborate 、 fungus Gibberella fujikuroi 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 145.5h， 生成 ent-3β,12α-dihydroxy-13-epi-manoyl oxide
  参考文献：
  名称：

  Formation of 2,3-seco-acids in the biotransformation of the diterpene ribenone by Gibberella fujikuroi

  摘要：

  The biotransformation of ribenone (ent-3-oxo-13-epi-manoyl oxide) (4) by the fungus Gibberella fujikuroi led to compounds hydroxylated at C-l(alpha), C-6(beta), C-11(beta) or C-12(beta), in addition to the 2,3-seco diacids 15, 17 and 19. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01190-9
• 作为产物：
  描述：

  ribenol 在 jones' reagent 作用下， 以 丙酮 为溶剂， 以77%的产率得到3-oxo-ent-13-epi-manoyl oxide
  参考文献：
  名称：

  Chemical-microbiological synthesis of ent-13-epi-manoyl oxides with biological activities

  摘要：

  The biotransformation of ent-13-epi-3-keto manoyl oxide, which possesses antileishmania activity, with Curvularia lunata produced ent-6 beta-hydroxy, ent-1 alpha-hydroxy, ent-11 beta-hydroxy and Delta(1)-derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (ent-6 beta) or C-11 tent-11 beta). The ent-6 beta-hydroxy and Delta(1)-derivatives inhibited growth of the pathogenic protozoa, Leishmania donovani. The biotransformation of ent-12 alpha-acetoxy-3 beta-hydroxy-13-epi-manoyl oxide and ent-3 beta-acetoxy-12-oxo-13-epi-manoyl oxide gave the ent-6 beta-hydroxyl derivatives. The incubation of ent-3 beta-acetoxy-12 beta-dihydroxy-13-epi-manoyl oxide gave ent-3 beta,12 beta-dihydroxy-13-epi-manoyl oxide and ent-3 beta,6 beta,12 beta-trihydroxy-13-epi-manoyl oxide (trimanoyl). Both products increased the activity of adenylatecyclase.

  DOI：

  10.1016/s0031-9422(00)90350-9

文献信息

• Biotransformation of the diterpene ribenone by Mucor plumbeus
  作者：Braulio M Fraga、Melchor G Hernández、Pedro González、Matı́as López、Sergio Suárez

  DOI：10.1016/s0040-4020(00)01052-8

  日期：2001.1

  The microbiological transformation of the diterpene ribenone (3-oxo-ent-13-epi-manoyl oxide) by the fungus Mucor plumbeus has been studied. Epoxidation of the vinyl group constitutes the main reaction and there exists a preference for hydroxylation at C-1(α), C-6(α or β) and C-12(β) and, to a lesser degree, at C-7(α) and C-11(β). Other observed reactions were the reduction of the 3-oxo group to a 3β-alcohol

  研究了真菌Mucor plumbeus对二萜核糖烯酮（3-氧代-ent-13-表-甘氨酰氧化物）的微生物转化。乙烯基的环氧化反应是主要反应，在C-1（α），C-6（α或β）和C-12（β）以及较小的C-7羟基存在羟基化（α）和C-11（β）。其他观察到的反应是将3-氧代基还原为3β-醇和形成具有1,2-双键的代谢产物。在这项工作中，已根据X射线数据修改了二萜类外毒素A，B和C在C-14处的立体化学。
• Five New Labdane-Type Diterpenes from Excoecaria agallocha. IV.
  作者：Tenji KONISHI、Yasuhiro FUJIWARA、Takao KONOSHIMA、Shiu KIYOSAWA

  DOI：10.1248/cpb.46.1393

  日期：——

  Five new labdane-type diterpenes were isolated from the resinous wood of Excoecaria agallocha. The structures of these compounds were established as ent-13-epi-8, 13-epoxy-2-hydroxylabda-1, 14-dien-3-one (1), ent-13-epi-8, 13-epoxy-14S, 15-dohydroxylabdan-3-one (2), ent-13-epi-8, 13-epoxy-2, 3-secolabd-14-ene-2, 3-dioic acid (3), ent-13-epi-8, 13-epoxy-2, 3-secolabd-14-ene-2, 3-dioic acid 3-methyl ester (4) and ent-13-epi-8, 13-epoxy-2-oxa-3-oxolabd-14-ene-1R-carboxylic acid (5).

  从印度楝树脂木中分离出五种新的腊烷型二萜。这些化合物的结构被确定为ent-13-epi-8, 13-epoxy-2-hydroxylabda-1, 14-dien-3-one (1)、ent-13-epi-8, 13-epoxy-14S, 15-dohydroxylabdan-3-one (2)、ent-13-epi-8, 13-epoxy-2, 3-secolabd-14-ene-2, 3-dioic acid (3)、ent-13-epi-8, 13-epoxy-2, 3-secolabd-14-ene-2, 3-dioic acid 3-methyl ester (4)和ent-13-epi-8, 13-epoxy-2-oxa-3-oxolabd-14-ene-1R-carboxylic acid (5)。
• Chemical Structures of Excoecarins A, B and C: Three New Labdane-Type Diterpenes from Wood, Excoecaria agallocha.
  作者：Tenji KONISHI、Shiu KIYOSAWA、Takao KONOSHIMA、Yasuhiro FUJIWARA

  DOI：10.1248/cpb.44.2100

  日期：——

  Three new diterpenes, excoecarins A (2), B (3) and C (4) have been isolated from the wood of Excoecaria agallocha LINN. The structures of excoecarins A, B and C were established as (13R, 14R)-ent-8α, 13;14, 15-diepoxy-13-epi-labda-3-one (2), (13R, 14S)-ent-8α, 13;14, 15-diepoxy-13-epi-labda-3-one (3), (13R, 14R)-ent-8α, 13;14, 15-diepoxy-13-epi-labda-3β-ol (4), respectively, on the basis of spectroscopic data and chemical evidence.

  从 Agallocha LINN Excoecaria 的木材中分离出了三种新的二萜类化合物，即十八萜 A (2)、B (3) 和 C (4)。经确定，十八烷烃 A、B 和 C 的结构分别为 (13R，14R)-ent-8α，13; 14，15-diepoxy-13-epi-labda-3-one (2)、(13R，14S)-ent-8α，13；在光谱数据和化学证据的基础上，分别得出了(13R, 14R)-ent-8α, 13; 14, 15-diepoxy-13-epi-labda-3-one(2)、(13R, 14S)-ent-8α, 13; 14, 15-diepoxy-13-epi-labda-3β-ol(4)。
• Stereostructure of Excoecarin H, a Novel seco-Labdane-Type Diterpene from Excoecaria agallocha.
  作者：Tenji KONISHI、Takao KONOSHIMA、Yasuhiro FUJIWARA、Shiu KIYOSAWA

  DOI：10.1248/cpb.46.721

  日期：——

  A novel seco-labdane-type diterpene, excoecarin H was isolated from resinous wood of Excoecaria aggallocha collected from Okinawa prefecture. Stereochemistry of the new diterpene was determined on the basis of chemical and physicochemical evidence.

  从冲绳县采集的 Excoecaria aggallocha 树脂木中分离出了一种新型仲酮-唇烷型二萜--桉叶素 H。根据化学和物理化学证据确定了这种新型二萜的立体化学结构。
• Fraga, Braulio M.; Hernandez, Melchor G.; Luis, Javier G., Anales de Quimica, 1994, vol. 90, # 7-8, p. 513 - 516
  作者：Fraga, Braulio M.、Hernandez, Melchor G.、Luis, Javier G.

  DOI：——

  日期：——