11-羟基柳杉酚 | 88664-08-8

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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: 11-羟基柳杉酚
• 英文名称: (4aS,10aS)-2,3,4,4a,10,10a-hexahydro-5,6-dihydroxy-1,1,4a-trimethyl-7-(1-methylethyl)phenanthren-9(1H)-one
• 英文别名: 12-O-demethylcryptojaponol；demethylcryptojaponol；11-hydroxyosugiol；11-hydroxysugiol；11,12-dihydroxyabieta-8,11,13-trien-7-one；12-O-demethylcryptojapanol；(4aS,10aS)-5,6-dihydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
• CAS: 88664-08-8
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: GDLRDIDXYBIPFY-YWZLYKJASA-N

物化性质

• 熔点：
  192-194℃
• 沸点：
  482.2±45.0 °C(Predicted)
• 密度：
  1.110±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-羟基柳杉酚 在 palladium on activated charcoal 、 18-冠醚-6 、 rhodium on alumina chromium(VI) oxide 、 盐酸 、 lithium aluminium tetrahydride 、 氯化亚砜 、 thallium(I) nitrate 、 alkaline hydrogen peroxide 、 硫酸 、 苯亚硒酸酐 、 氢气 、 溴 、 sodium methylate 、 silica gel 、 lithium carbonate 、 sodium hydride 、 potassium carbonate 、 calcium carbonate 、 lithium bromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 四氯化碳 、 氢氧化钾 、 乙醚 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 紫珠酮素
  参考文献：
  名称：

  Synthesis of Callicarpone, a Fish-killing Diterpene

  摘要：

  Callicarpone 是一种杀鱼二萜，由 (+)-11-acetoxy-12-benzoyloxy-8,11,13-abietatrien-7-one 通过中间体 11,11-ethylenedioxy-9βH-abieta-13(15)-en-12-one 合成。

  DOI：

  10.1246/cl.1988.1399
• 作为产物：
  描述：

  12-benzoyloxy-11-hydroxyabieta-8,11,13-triene 在 chromium(VI) oxide 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 14.5h， 生成 11-羟基柳杉酚
  参考文献：
  名称：

  Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE

  摘要：

  Variously oxidized 12 natural abietanes, 6,7-dehydroferruginol methyl ether (3), ferruginol (5), 11-hydroxy-12-oxo-7,9(11),13-abietatriene (7), royleanone (9), demethyl cryptojaponol (12), salvinolone (14), sugiol methyl ether (16), sugiol (17), 5,6-dehydrosugiol methyl ether (19), 5,6-dehydrosugiol (20), 6 beta -hydroxyferruginol (23), and taxodione (25) were synthesized. Antimicrobial activities of synthesized phenolic diterpenes and their related compounds against MRSA and VRE were evaluated. Phenols (12-hydroxyabieta-8,11,13-trien-6-one 22 and 23), catechols (12 and 14) and taxodione 25 showed potent activity with 4-10 mug/mL of MIC against MRSA and 4-16 mug/mL of MIC against VRE. (-)-Ferruginol showed more potent activity than natural type (+)-ferruginol. Quinone methide 7 showed the most potent activity with 0.5-1 mug/mL of MIC against both MRSA and VRE. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00253-4

文献信息

• Abietane diterpenoids from the root of Salvia phlomoides
  作者：J HUESORODRIGUEZ、M JIMENO、B RODRIGUEZ、G SAVONA、M BRUNO

  DOI：10.1016/0031-9422(83)80033-8

  日期：——

  Abstract From the root of Salvia phlomoides three new abietane diterpenoids, demethylcryptojaponol, 14-deoxycoleon U and salviphlomone, have been isolated, besides the previously known diterpenes 8,13-abietadiene, 8,11,13-abietatriene, royleanone, 7α-acetoxyroyleanone, taxodione, taxodone, cryptojaponol and sugiol. The structures of demethylcryptojaponol (11,12-dihydroxy-8,11,13-abietatrien-7-one)

  摘要 从丹参的根中分离出三种新的松香烷二萜类化合物，脱甲基隐花楸醇、14-脱氧Coleon U 和丹参，除已知的二萜类8,13-松香二烯、8,11,13-松香三烯、苯丙酮-α-丙酮、紫杉酮、紫杉酮、隐花酚和杉醇。demethylcryptojaponol (11,12-dihydroxy-8,11,13-abietatrien-7-one), 14-deoxycoleon U (6,11,12-trihydroxy-5,8,11,13-abietatetraen-7-one)的结构) 和 Salviphlomone (6α,7β-dihydroxy-8,13-abietadiene-11,12-dione) 是通过化学和光谱方法建立的。
• MATSUMOTO, TAKASHI;IMAI, SACHIHIKO;MIMURA, KAZUYOSHI;AIBA, KEIZO, CHEM. LETT.,(1988) N 8, C. 1399-1402
  作者：MATSUMOTO, TAKASHI、IMAI, SACHIHIKO、MIMURA, KAZUYOSHI、AIBA, KEIZO

  DOI：——

  日期：——
• Cytochrome P450 promiscuity leads to a bifurcating biosynthetic pathway for tanshinones
  作者：Juan Guo、Xiaohui Ma、Yuan Cai、Ying Ma、Zhilai Zhan、Yongjin J. Zhou、Wujun Liu、Mengxin Guan、Jian Yang、Guanghong Cui、Liping Kang、Lei Yang、Ye Shen、Jinfu Tang、Huixin Lin、Xiaojing Ma、Baolong Jin、Zhenming Liu、Reuben J. Peters、Zongbao K. Zhao、Luqi Huang

  DOI：10.1111/nph.13790

  日期：2016.4

  Summary Cytochromes P450 (CYPs) play a key role in generating the structural diversity of terpenoids, the largest group of plant natural products. However, functional characterization of CYPs has been challenging because of the expansive families found in plant genomes, diverse reactivity and inaccessibility of their substrates and products. Here we present the characterization of two CYPs, CYP76AH3 and CYP76AK1, which act sequentially to form a bifurcating pathway for the biosynthesis of tanshinones, the oxygenated diterpenoids from the Chinese medicinal plant Danshen (Salvia miltiorrhiza). These CYPs had similar transcription profiles to that of the known gene responsible for tanshinone production in elicited Danshen hairy roots. Biochemical and RNA interference studies demonstrated that both CYPs are promiscuous. CYP76AH3 oxidizes ferruginol at two different carbon centers, and CYP76AK1 hydroxylates C‐20 of two of the resulting intermediates. Together, these convert ferruginol into 11,20‐dihydroxy ferruginol and 11,20‐dihydroxy sugiol en route to tanshinones. Moreover, we demonstrated the utility of these CYPs by engineering yeast for heterologous production of six oxygenated diterpenoids, which in turn enabled structural characterization of three novel compounds produced by CYP‐mediated oxidation. Our results highlight the incorporation of multiple CYPs into diterpenoid metabolic engineering, and a continuing trend of CYP promiscuity generating complex networks in terpenoid biosynthesis.
• USE CERTAIN DITERPENE COMPOUNDS IN THE TREATMENT OF ANDROGEN RECEPTOR-ASSOCIATED DISEASES
  申请人：HSIAO Pei-Wen

  公开号：US20100022632A1

  公开（公告）日：2010-01-28

  The present invention discloses certain diterpenes that can be used to inhibit androgen receptor activity, induce apoptosis and block cell cycle progression of androgen receptor-dependent cells. Androgen receptor has been associated with various diseases such as prostate cancer, androgeneic alopecia, breast cancer, acne etc. Accordingly, the present invention further discloses methods of treating androgen receptor-associated diseases by administering the disclosed diterpenes.
• US8519007B2
  申请人：——

  公开号：US8519007B2

  公开（公告）日：2013-08-27