isopimara-7,15-dien-19-ol | 83692-05-1

• 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: isopimara-7,15-dien-19-ol
• 英文别名: 7,15-isopimaradien-19-ol；isopimaran-19-ol；isopimarinol；akhdarenol；1-Phenanthrenemethanol, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,4a,7-trimethyl-, (1S,4aR,4bS,7S,10aR)-；[(1S,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthren-1-yl]methanol
• CAS: 83692-05-1
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: DUEINKIQNGZKPL-WKWVNEEDSA-N

物化性质

• 沸点：
  382.1±11.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  isopimara-7,15-dien-19-ol 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以0.08 g的产率得到isopimara-8(9),15-dien-19-ol
  参考文献：
  名称：

  Ceccherelli, Paolo; Curini, Massimo; Marcotullio, Maria Carla, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2173 - 2176

  摘要：

  DOI：
• 作为产物：
  描述：

  3β,19-oxidoisopimara-7,15-diene 在 盐酸 、 lithium 作用下， 以 四氢呋喃 、 氨 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 isopimara-7,15-dien-19-ol
  参考文献：
  名称：

  Ceccherelli, Paolo; Curini, Massimo; Marcotullio, Maria Carla, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2173 - 2176

  摘要：

  DOI：

文献信息

• In Vitro Antimicrobial Activity of Isopimarane-Type Diterpenoids
  作者：Vera M. S. Isca、Joana Andrade、Ana Sofia Fernandes、Paulo Paixão、Clara Uriel、Ana María Gómez、Noélia Duarte、Patrícia Rijo

  DOI：10.3390/molecules25184250

  日期：——

  The antimicrobial evaluation of twelve natural and hemisynthetic isopimarane diterpenes are reported. The compounds were evaluated against a panel of Gram-positive bacteria, including two methicillin-resistant Staphylococcus aureus (MRSA) strains and one vancomycin-resistant Enterococcus (VRE) strain. Only natural compounds 7,15-isopimaradien-19-ol (1) and 19-acetoxy-7,15-isopimaradien-3β-ol (6) showed promising results. Isopimarane (1) was the most active, showing MIC values between 6.76 µM against S. aureus (ATCC 43866) and 216.62 µM against E. faecalis (FFHB 427483) and E. flavescens (ATCC 49996). Compound (6) showed moderated activity against all tested microorganisms (MIC between value 22.54 and 45.07 µM). These compounds were found to be active against the methicillin-sensitive strains of S. aureus (CIP 106760 and FFHB 29593), showing MIC values of 13.55 (1) and 22.54 (6) µM. Both compounds were also active against vancomycin-resistant E. faecalis (ATCC 51299) (MIC values of 54.14 and 45.07 µM, respectively). In addition, the cytotoxicity of nine compounds 7,15-isopimaradien-3β,19-diol (2); mixture: 15-isopimarene-8β-isobutyryloxy-19-ol and 15-isopimarene-8β-butyryloxy-19-ol (3); 3β-acetoxy-7,15-isopimaradiene-19-ol (5); 19-acetoxy-7,15-isopimaradiene-3β-ol (6); 3β,19-diacetoxy-7,15-isopimaradiene (8); 15-isopimarene-8β,19-diol (9); 19-O-β-d-glucopyranoside-7,15-isopimaradiene (10); lagascatriol-16-O-β-d-glucopyranoside (11) and lagascatriol-16-O-α-d-mannopyranoside (12) was evaluated in the human breast cancer cell line MDA-MB-231. Isopimarane (2) was the only compound showing some cytotoxicity. The IC50 value of compound (2) was 15 µM, suggesting a mild antiproliferative activity against these breast cancer cells.

  报道了十二种天然和半合成异皮马兰二萜化合物的抗微生物评价。这些化合物被评估对一系列革兰氏阳性细菌的活性，包括两株耐甲氧西林金黄色葡萄球菌(MRSA)菌株和一株耐万古霉素肠球菌(VRE)菌株。只有天然化合物7,15-异皮马烯-19-醇(1)和19-乙酰氧基-7,15-异皮马烯-3β-醇(6)显示出有希望的结果。异皮马烷(1)表现出最活性，对金黄色葡萄球菌(ATCC 43866)的最小抑菌浓度(MIC)值在6.76 µM，对嗜肠球菌(FFHB 427483)和黄色链球菌(ATCC 49996)的MIC值分别为216.62 µM。化合物(6)对所有测试微生物表现出中等活性(MIC值在22.54和45.07 µM之间)。这些化合物对甲氧西林敏感的金黄色葡萄球菌菌株(CIP 106760和FFHB 29593)表现出活性，MIC值分别为13.55(1)和22.54(6) µM。这两种化合物还对耐万古霉素的嗜肠球菌(ATCC 51299)表现出活性(MIC值分别为54.14和45.07 µM)。此外，对九种化合物7,15-异皮马烯-3β,19-二醇(2); 混合物: 15-异皮马烷-8β-异丁酰氧基-19-醇和15-异皮马烷-8β-丁酰氧基-19-醇(3); 3β-乙酰氧基-7,15-异皮马烯-19-醇(5); 19-乙酰氧基-7,15-异皮马烯-3β-醇(6); 3β,19-二乙酰氧基-7,15-异皮马烯(8); 15-异皮马烷-8β,19-二醇(9); 19-O-β-D-葡萄糖吡喃糖苷-7,15-异皮马烯(10); 拉加卡三醇-16-O-β-D-葡萄糖吡喃糖苷(11)和拉加卡三醇-16-O-α-D-甘露糖吡喃糖苷(12)在人类乳腺癌细胞系MDA-MB-231中进行了细胞毒性评估。异皮马烷(2)是唯一显示出一定细胞毒性的化合物。化合物(2)的IC50值为15 µM，表明对这些乳腺癌细胞具有轻微的抗增殖活性。
• Studies on the constituents of the crude drug "Fritillariae bulbus." III. On the diterpenoid constituents of fresh bulbs of Fritillaria thunbergii Miq.
  作者：JUNICHI KITAJIMA、TETSUYA KOMORI、TOSHIO KAWASAKI

  DOI：10.1248/cpb.30.3912

  日期：——

  In addition to trans-communol and trans-communic acid (obtained in the form of the methyl ester), seven new diterpenoids were isolated as non basic constituents from fresh bulbs of Fritillaria thunbergii MIQ. (Liliaceae). Their structures were determined to be isopimaran-19-ol (3), isopimaran-19-oic acid [obtained in the form of the methyl ester (4)], ent-kauran-16β, 17-diol (5), ent-kauran-16α, 17-diol (6), ent-16β, 17-epoxy-kaurane (7), ent-16α-methoxy-kauran-17-ol (8), and ent-kaur-15-en-17-ol (9).

  除了反式厚朴酚和反式厚朴酸（以甲基酯的形式获得）外，还从新鲜的 Fritillaria thunbergii MIQ.(百合科）的新鲜鳞茎中分离出了七种新的二萜类非碱性成分。它们的结构被确定为异马兰-19-醇（3）、异马兰-19-酸[以甲酯形式获得（4）]、ent-kauran-16β，17-二醇（5）、ent-kauran-16α，17-二醇（6）、ent-16β，17-环氧-kaurane（7）、ent-16α-甲氧基-kauran-17-醇（8）和ent-kaur-15-烯-17-醇（9）。
• LC-MS- and ¹H NMR Spectroscopy-Guided Identification of Antifungal Diterpenoids from <i>Sagittaria latifolia</i>
  作者：Ranga Rao Ravu、Melissa R. Jacob、Cynthia Jeffries、Ying Tu、Shabana I. Khan、Ameeta K. Agarwal、R. Kiplin Guy、Larry A. Walker、Alice M. Clark、Xing-Cong Li

  DOI：10.1021/acs.jnatprod.5b00470

  日期：2015.9.25

  Antifungal screening of small-molecule natural product libraries showed that a column fraction (CF) derived from the plant extract of Sagittaria latifolia was active against the fungal pathogen Cryptococcus neoformans. Dereplication analysis by liquid chromatography mass spectrometry (LC-MS) and proton nuclear magnetic resonance spectroscopy (H-1 NMR) indicated the presence of new compounds in this CF. Subsequent fractionation of the plant extract resulted in the identification of two new isopimaradiene-type diterpenoids, 1 and 2. The structures of 1 and 2 were determined by chemical methods and spectroscopic analysis as isopimara-7,15-dien-19-ol 19-O-alpha-L-arabinofuranoside and isopimara-7,15-dien-19-ol 19-O-alpha-L-(5'-acetoxy)-arabinofuranoside, respectively. Compound 1 exhibited IC50 values of 3.7 and 1.8 mu g/mL, respectively, against C. neoformans and C. gattii. Its aglycone, isopimara-7,15-dien-19-ol (3), resulting from acid hydrolysis of 1, was also active against the two fungal pathogens, with IC50 values of 9.2 and 6.8 mu g/mL, respectively. This study demonstrates that utilization of the combined LC-MS and H-1 NMR analytical tools is an improved chemical screening approach for hit prioritization in natural product drug discovery.
• Ceccherelli, Paolo; Curini, Massimo; Marcotullio, Maria Carla, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2173 - 2176
  作者：Ceccherelli, Paolo、Curini, Massimo、Marcotullio, Maria Carla

  DOI：——

  日期：——