stemod-12-en-2-one | 41703-76-8

• 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: stemod-12-en-2-one
• 英文别名: (1R,2S,7S,10S,12S)-2,6,6,13-tetramethyltetracyclo[10.3.1.01,10.02,7]hexadec-13-en-4-one
• CAS: 41703-76-8
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: BCLFWSYURRBECE-NHQOTNMQSA-N

物化性质

• 熔点：
  73-75 °C(Solvent: Acetone)
• 沸点：
  382.1±31.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  stemod-12-en-2-one 在 吡啶 、 四丁基氢氧化铵 、 溴 、 silver(I) acetate 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 48.0h， 生成 13α-hydroxystemod-11-en-2-one
  参考文献：
  名称：

  具有脂质过氧化、环氧合酶和人肿瘤细胞增殖抑制活性的 Stemodin 衍生类似物

  摘要：

  制备了一系列源自抗病毒和细胞毒性二萜类化合物的类似物，并评估了它们的脂质过氧化 (LPO)、环氧合酶-1 (COX-1) 和-2 (COX-2) 以及肿瘤细胞增殖抑制活性. 大黄素的氧化产生大黄酮，然后将其转化为大黄素-12-en-2-one。后者在 Petrow 条件（溴；醋酸银/吡啶）下的反应主要产生二溴化的 abeo-stachanes。二溴化合物的溶剂分解产生水解产物，其中一些具有重新排列的骨架。在脂质过氧化抑制试验中，三种化合物表现出显着的活性。有趣的是，所有类似物都显示出比 COX-2 更高的 COX-1 酶抑制。尽管一些二萜限制了一些人类肿瘤细胞系的生长，

  DOI：

  10.1016/j.phytochem.2011.08.024
• 作为产物：
  描述：

  stemodin 在 硫酸 作用下， 以 丙酮 为溶剂， 反应 68.0h， 生成 stemod-12-en-2-one
  参考文献：
  名称：

  Investigation of the importance of the C-2 oxygen function in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145

  摘要：

  A new stemodinoside, stemodin-a-L-arabinofuranoside (5), was isolated from the plant Stemodia maritima. Incubation of stemodin (2) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(S)-trihydroxystemodane (17) and 2alpha,3beta,13(S),16alpha-tetrahydroxystemodane (18) whilst stemodinone (8) afforded 6alpha,13(S)-dihydroxystemodan-2-one (19). The bioconversion of 2beta,13(S)-dihydroxystemodane (10) by the fungus yielded 2beta,7beta,13(S)-trihydroxystemodane (20) whereas stemod-12-en-2-one (9) provided 7beta,17-dihydroxystemod-12-en-2-one (21). The results provide useful information about the relationship between the functional groups of the substrates and their potential for bioconversion. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2004.01.011

文献信息

• The potential of Cyathus africanus for transformation of terpene substrates
  作者：Kayanne P. McCook、Avril R.M. Chen、William F. Reynolds、Paul B. Reese

  DOI：10.1016/j.phytochem.2012.06.018

  日期：2012.10

  The insecticidal sesquiterpenes cadina-4,10(15)-dien-3-one and aromadendr-1(10)-en-9-one were administered to the fungus Cyathus africanus ATCC 35853. Biotransformation of the former produced (4R)-9 alpha-hydroxycadin-10(15)-en-3-one, while the latter gave 2 beta-hydroxyaromadendr-1(10)-en-9-one, 2 alpha-hydroxyaromadendr-1(10)-en-9-one and 10 alpha-hydroxy-1 beta,2 beta-epoxyaromadendran-9-one. The bioconversion of santonin led to the production of two analogues, 11,13-dihydroxysantonin and the hitherto unreported 8 alpha,13-dihydroxysantonin, while cedrol yielded 3 beta,8 beta-dihydroxycedrane and 3 alpha,8 beta-dihydroxycedrane. Stemod-12-ene, a diterpene, was transformed to 2-oxostemar-13-ene, a hitherto unknown analogue with a rearranged carbon framework. When methyl betulonate, a triterpenoid belonging to the lupane family, was supplied to the fungus 18 alpha-ursane and 18 alpha-oleanane derivatives, namely 19 beta-hydroxy-3-oxo-18 alpha-oleanan-28-oic acid and 19 alpha-hydroxy-3-oxo-18 alpha-ursan-28-oic acids, were generated. There are no previous reports of fungal transformation of a triterpene in which a skeletal rearrangement occurred. All substrate administration experiments were done in the presence of the terpene cyclase inhibitor chlorocholine chloride (CCC), using the single phase - pulse feed method. (c) 2012 Elsevier Ltd. All rights reserved.
• Structures of stemodin and stemodinone
  作者：P. S. Manchand、J. D. White、Hal. Wright、Jon. Clardy

  DOI：10.1021/ja00789a060

  日期：1973.4
• Investigation of the importance of the C-2 oxygen function in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145
  作者：Glenroy D.A. Martin、William F. Reynolds、Paul B. Reese

  DOI：10.1016/j.phytochem.2004.01.011

  日期：2004.3

  A new stemodinoside, stemodin-a-L-arabinofuranoside (5), was isolated from the plant Stemodia maritima. Incubation of stemodin (2) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(S)-trihydroxystemodane (17) and 2alpha,3beta,13(S),16alpha-tetrahydroxystemodane (18) whilst stemodinone (8) afforded 6alpha,13(S)-dihydroxystemodan-2-one (19). The bioconversion of 2beta,13(S)-dihydroxystemodane (10) by the fungus yielded 2beta,7beta,13(S)-trihydroxystemodane (20) whereas stemod-12-en-2-one (9) provided 7beta,17-dihydroxystemod-12-en-2-one (21). The results provide useful information about the relationship between the functional groups of the substrates and their potential for bioconversion. (C) 2004 Elsevier Ltd. All rights reserved.
• Stemodin-derived analogues with lipid peroxidation, cyclooxygenase enzymes and human tumour cell proliferation inhibitory activities
  作者：Floyd A. Russell、Vanisree Mulabagal、Dwayne R. Thompson、Marvadeen A. Singh-Wilmot、William F. Reynolds、Muraleedharan G. Nair、Vratislav Langer、Paul B. Reese

  DOI：10.1016/j.phytochem.2011.08.024

  日期：2011.12

  mainly dibrominated abeo-stachanes. Solvolysis of the dibromo compounds gave products of hydrolysis, some with rearranged skeleta. In the lipid peroxidation inhibitory assay three of the compounds exhibited prominent activity. Interestingly, all the analogues showed higher COX-1 enzyme inhibition than COX-2. Although a few of the diterpenes limited the growth of some human tumour cell lines, most compounds

  制备了一系列源自抗病毒和细胞毒性二萜类化合物的类似物，并评估了它们的脂质过氧化 (LPO)、环氧合酶-1 (COX-1) 和-2 (COX-2) 以及肿瘤细胞增殖抑制活性. 大黄素的氧化产生大黄酮，然后将其转化为大黄素-12-en-2-one。后者在 Petrow 条件（溴；醋酸银/吡啶）下的反应主要产生二溴化的 abeo-stachanes。二溴化合物的溶剂分解产生水解产物，其中一些具有重新排列的骨架。在脂质过氧化抑制试验中，三种化合物表现出显着的活性。有趣的是，所有类似物都显示出比 COX-2 更高的 COX-1 酶抑制。尽管一些二萜限制了一些人类肿瘤细胞系的生长，