(E)-(S)-3-Hydroxymethyl-1-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-ene-1,5-diol | 198885-19-7

• 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: (E)-(S)-3-Hydroxymethyl-1-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-ene-1,5-diol
• 英文别名: (E,1S)-1-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-(hydroxymethyl)pent-2-ene-1,5-diol
• CAS: 198885-19-7
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: ZJRJKCCRIRYFON-BJRBBPMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-alpha-甲氧基苯乙酸 、 (E)-(S)-3-Hydroxymethyl-1-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-ene-1,5-diol 在 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (S)-Methoxy-phenyl-acetic acid (E)-(S)-4-hydroxy-2-[2-((S)-2-methoxy-2-phenyl-acetoxy)-ethyl]-4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-but-2-enyl ester
  参考文献：
  名称：

  Bioactive Labdane Diterpenoids from Renealmia alpinia Collected in the Suriname Rainforest

  摘要：

  The preservation of tropical rainforests is an important goal both for the intrinsic value of their cultural and biological diversity as well as for the well-being of the peoples who make these forests their home. In addition, tropical forests are potential sources of new pharmaceutical products that can only be found by chemical prospecting in Nature's genetically encoded combinatorial library. As part of an effort to integrate biodiversity conservation and drug discovery with economic development, we have initiated a collaborative program to discover potential pharmaceuticals in the rainforest of Suriname. The plant Renealmia alpinia (Zingiberaceae) was selected for investigation based on its ethnomedical use as a febrifuge, but testing in the yeast Sc-7 assay gave a positive response, indicative of cytotoxic activity. Using this bioassay, the two new labdane diterpenes, 11-hydroxy-8(17),12(E)-labdadien-15,-16-dial 11,15-hemiacetal(1) and 16-oxo-8(17),12(E)-labdadien-15-oic acid (2), and the known diterpene, 8(17),12(E)-labdadien-15,16-dial (3), have been isolated. Their structures were elucidated by 1D and 2D NMR techniques (DEFT, COSY, HETCOR, HMBC, and NOESY) and IR, UV, and MS spectra, and the absolute stereochemistry of 1 was established by CD spectroscopy and by the formation and NMR analysis of alpha-methoxyphenylacetyl esters. The hemiacetal 1 was cytotoxic to M109 cells, with an IC50 value of 2.6 mu g/mL.

  DOI：

  10.1021/np970233c
• 作为产物：
  描述：

  (2R,6S)-2-Hydroxy-6-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-3,6-dihydro-2H-pyran-4-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以86.6%的产率得到(E)-(S)-3-Hydroxymethyl-1-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-ene-1,5-diol
  参考文献：
  名称：

  Bioactive Labdane Diterpenoids from Renealmia alpinia Collected in the Suriname Rainforest

  摘要：

  The preservation of tropical rainforests is an important goal both for the intrinsic value of their cultural and biological diversity as well as for the well-being of the peoples who make these forests their home. In addition, tropical forests are potential sources of new pharmaceutical products that can only be found by chemical prospecting in Nature's genetically encoded combinatorial library. As part of an effort to integrate biodiversity conservation and drug discovery with economic development, we have initiated a collaborative program to discover potential pharmaceuticals in the rainforest of Suriname. The plant Renealmia alpinia (Zingiberaceae) was selected for investigation based on its ethnomedical use as a febrifuge, but testing in the yeast Sc-7 assay gave a positive response, indicative of cytotoxic activity. Using this bioassay, the two new labdane diterpenes, 11-hydroxy-8(17),12(E)-labdadien-15,-16-dial 11,15-hemiacetal(1) and 16-oxo-8(17),12(E)-labdadien-15-oic acid (2), and the known diterpene, 8(17),12(E)-labdadien-15,16-dial (3), have been isolated. Their structures were elucidated by 1D and 2D NMR techniques (DEFT, COSY, HETCOR, HMBC, and NOESY) and IR, UV, and MS spectra, and the absolute stereochemistry of 1 was established by CD spectroscopy and by the formation and NMR analysis of alpha-methoxyphenylacetyl esters. The hemiacetal 1 was cytotoxic to M109 cells, with an IC50 value of 2.6 mu g/mL.

  DOI：

  10.1021/np970233c

文献信息

• Bioactive Labdane Diterpenoids from <i>Renealmia alpinia</i> Collected in the Suriname Rainforest
  作者：Bing-Nan Zhou、Nina J. Baj、Thomas E. Glass、Stan Malone、Marga C. M. Werkhoven、Frits van Troon、David、Jan H. Wisse、David

  DOI：10.1021/np970233c

  日期：1997.12.1

  The preservation of tropical rainforests is an important goal both for the intrinsic value of their cultural and biological diversity as well as for the well-being of the peoples who make these forests their home. In addition, tropical forests are potential sources of new pharmaceutical products that can only be found by chemical prospecting in Nature's genetically encoded combinatorial library. As part of an effort to integrate biodiversity conservation and drug discovery with economic development, we have initiated a collaborative program to discover potential pharmaceuticals in the rainforest of Suriname. The plant Renealmia alpinia (Zingiberaceae) was selected for investigation based on its ethnomedical use as a febrifuge, but testing in the yeast Sc-7 assay gave a positive response, indicative of cytotoxic activity. Using this bioassay, the two new labdane diterpenes, 11-hydroxy-8(17),12(E)-labdadien-15,-16-dial 11,15-hemiacetal(1) and 16-oxo-8(17),12(E)-labdadien-15-oic acid (2), and the known diterpene, 8(17),12(E)-labdadien-15,16-dial (3), have been isolated. Their structures were elucidated by 1D and 2D NMR techniques (DEFT, COSY, HETCOR, HMBC, and NOESY) and IR, UV, and MS spectra, and the absolute stereochemistry of 1 was established by CD spectroscopy and by the formation and NMR analysis of alpha-methoxyphenylacetyl esters. The hemiacetal 1 was cytotoxic to M109 cells, with an IC50 value of 2.6 mu g/mL.