Δ^7,8-virescenoside B aglycon | 22343-47-1

• 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: Δ^7,8-virescenoside B aglycon
• 英文别名: 7,15-isopimaradien-3β,19-diol；virescenol B；(1S,2S,4aR,4bS,7S,10aR)-7-ethenyl-1-(hydroxymethyl)-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthren-2-ol
• CAS: 22343-47-1
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: NFUDIHFRVVFXHZ-GNVSMLMZSA-N

物化性质

• 熔点：
  125 °C
• 沸点：
  420.1±45.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Δ^7,8-virescenoside B aglycon 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 72.0h， 生成 Isovirescenol B
  参考文献：
  名称：

  Polonsky,J. et al., Bulletin de la Societe Chimique de France, 1970, p. 1912 - 1918

  摘要：

  DOI：
• 作为产物：
  描述：

  甲瓦龙酸内酯 在 Oospora virescens 作用下， 反应 22.0h， 生成 Δ^7,8-virescenoside B aglycon
  参考文献：
  名称：

  2 H nmr测定紫杉醇B生物合成中烯丙基置换的立体化学

  摘要：

  将（5 R）-[5- 2 H]甲羟戊酸酯进料到豌豆孢菌中，并且对所得豌豆酚B的衍生物进行2 H nmr分析，确定生成环c的焦磷酸的烯丙基取代发生在总体抗立体化学上。

  DOI：

  10.1039/c39810000280

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。
• New Diterpenic Altrosides of the Fungus <i>Acremonium striatisporum</i> Isolated from a Sea Cucumber
  作者：Shamil Sh. Afiyatullov、Tatyana A. Kuznetsova、Vladimir V. Isakov、Mikhail V. Pivkin、Nina G. Prokof'ev、George B. Elyakov

  DOI：10.1021/np9904004

  日期：2000.6.1

  Two new diterpenic glycosides, virescenosides M (1) and N (2), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined on the basis of MS and NMR data as beta-D-altropyranosido-19-7-oxo-isopimara-8,15-diene-2alp ha, 3beta-diol (1) and beta-D-altropyranosido-19-isopimara-7, 15-diene-2alpha,3beta

  两种新的二萜糖苷，即virescenosides M（1）和N（2），已从海洋菌丝孢霉KMM 4401的海洋菌株中分离得到，该菌株与全人类Eupentacta欺诈相联系。它们的结构根据MS和NMR数据确定为β-D-altropyranosido-19-7-oxo-isopimara-8,15-diene-2alpha，3beta-diol（1）和beta-D-altropyranosido-19 -isopimara-7，15-diene-2alpha，3beta，6beta-triol（2）。还分离出了来自陆生菌株Acremonium luzulae的其他三种白藜芦醇甙（3-5），分别被鉴定为杀鼠灵A，B和C。检查了紫杉甙的细胞毒活性。
• Carbon-carbon bond formation by the reduction of dienic esters
  作者：Massimo Curini、Rita Coccia、Paolo Ceccherelli、Timothy D. J. Halls、Barry Porter、Ernest Wenkert

  DOI：10.1021/jo00185a057

  日期：1984.6
• Isopimarane diterpenoids from Aeollanthus rydingianus and their antimicrobial activity
  作者：Patricia Rijo、Maria Fátima Simões、Aida Duarte、Benjamín Rodríguez

  DOI：10.1016/j.phytochem.2009.06.008

  日期：2009.6

  Four acyloxy-isopimarane derivatives along with two known isopimarane diterpenoids, the flavone cirsimaritin and the sterols P-sitosterol and stigmasterol were isolated from the aerial parts of Aeollanthus rydingianus. The structures of the compounds were established on the basis of spectroscopic analysis and chemical evidence. The isolated substances were screened for antimicrobial activity against Gram-positive and Gram-negative bacteria and a yeast strain. 19-Acetoxy-7,15-isopimaradien-3 beta-ol and 7,15-isopimaradien-19-ol showed minimum inhibitory concentration (MIC) values of 3.90-15.62 mu g/ml for Staphylococcus aureus and of 7.81 mu g/ml for Enterococcus hirae. (C) 2009 Elsevier Ltd. All rights reserved.
• Isopimarane diterpene glycosides, isolated from endophytic fungus Paraconiothyrium sp. MY-42
  作者：Yoshihito Shiono、Miwako Kikuchi、Takuya Koseki、Tetsuya Murayama、Eunsang Kwon、Nobuhiro Aburai、Ken-ichi Kimura

  DOI：10.1016/j.phytochem.2011.04.016

  日期：2011.8

  Six isopimarane diterpenes, compounds 1-6, were isolated from the endophytic fungus Paraconiothyrium sp. MY-42. Compound 1 possesses a 19-glucopyranosyloxy group. Its structure was first elucidated by spectroscopic data analysis and finally confirmed by X-ray crystallography, whereas structures 2-6 were mainly elucidated based on the analysis of spectroscopic evidence. Compounds 2 and 3 showed moderate cytotoxicities against the human promyelocytic leukemia cell line HL60 (IC50 6.7 mu M value for 2 and 9.8 mu M for 3). (C) 2011 Elsevier Ltd. All rights reserved.