(E)-labda-8(17),12-diene-15,16-diol | 114388-88-4

• 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)-labda-8(17),12-diene-15,16-diol
• 英文别名: (2E)-2-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]butane-1,4-diol
• CAS: 114388-88-4
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: DDVAZDCKVCUKBI-OQONWLFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-labda-8(17),12-diene-15,16-diol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以81%的产率得到(E)-labda-8(20),12-diene-15,16-dial
  参考文献：
  名称：

  Conversion of sclareol into (+)-galanolactone and (+)-labdienedial

  摘要：

  A short, regiospecific and first synthesis of (+)-galanolactone 5 and (+)labdienedial 1 1 was achieved from sclareol, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00485-1
• 作为产物：
  描述：

  香紫苏醇 在 喹啉 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 、 叔丁醇 为溶剂， 反应 14.5h， 生成 (E)-labda-8(17),12-diene-15,16-diol
  参考文献：
  名称：

  Conversion of sclareol into (+)-galanolactone and (+)-labdienedial

  摘要：

  A short, regiospecific and first synthesis of (+)-galanolactone 5 and (+)labdienedial 1 1 was achieved from sclareol, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00485-1

文献信息

• GLUCAGON-LIKE PEPTIDE 1 (GLP-1) RECEPTOR MODULATORS AND USES THEREOF IN REGULATING BLOOD GLUCOSE LEVELS
  申请人：Liang Chi-Ming

  公开号：US20140350100A1

  公开（公告）日：2014-11-27

  The present disclosure provides novel glucagon-like peptide-1 (GLP-1) receptor modulators such as compounds of Formula (I) or (II), and pharmaceutically acceptable salts thereof. The present disclosure also provides pharmaceutical compositions, kits, and uses that involve the GLP-1 receptor modulators for regulating blood glucose levels and/or treating diabetes via, e.g., modulating the endogenous signaling pathways mediated by the GLP-1 receptor.

  本公开提供了新型胰高血糖素样肽-1（GLP-1）受体调节剂，例如式（I）或（II）的化合物，以及其药学上可接受的盐。本公开还提供了涉及GLP-1受体调节剂用于调节血糖水平和/或治疗糖尿病的药物组合物、试剂盒和用途。例如，通过调节由GLP-1受体介导的内源性信号通路。
• Diterpenes from the rhizomes of Alpinia formosana
  作者：Hideji Itokawa、Shinji Yoshimoto、Hiroshi Morita

  DOI：10.1016/0031-9422(88)83115-7

  日期：1988.1

  Abstract A new labdane-type diterpene, (E)-labda-8(17),12-diene-15-ol-16-al was isolated from the rhizomes of Alpinia formosana together with a bisnorlabdane-type diterpene, (E)-15,16-bisnorlabda-8(17),11-diene-13-one, two known sesquiterpenes and three known phenolic compounds. The chemotaxonomic significance of these findings is discussed briefly.

  摘要 从台湾山姜根茎中分离得到一种新的劳丹脂型二萜(E)-labda-8(17),12-diene-15-ol-16-al和一种双去甲劳丹烷型二萜(E)- 15,16-bisnorlabda-8(17),11-diene-13-one、两种已知的倍半萜烯和三种已知的酚类化合物。简要讨论了这些发现的化学分类学意义。
• Conversion of sclareol into (+)-galanolactone and (+)-labdienedial
  作者：Mankil Jung、Seokjoon Lee、Byunghee Yoon

  DOI：10.1016/s0040-4039(97)00485-1

  日期：1997.4

  A short, regiospecific and first synthesis of (+)-galanolactone 5 and (+)labdienedial 1 1 was achieved from sclareol, respectively. (C) 1997 Elsevier Science Ltd.
• Synthesis and biological evaluation of (+)-labdadienedial, derivatives and precursors from (+)-sclareolide
  作者：Miguel A. González、Juan Mancebo-Aracil、Veronica Tangarife-Castaño、Lee Agudelo-Goméz、Bibiana Zapata、Ana Mesa-Arango、Liliana Betancur-Galvis

  DOI：10.1016/j.ejmech.2010.06.029

  日期：2010.9

  Labdadienedial and a series of C15,C16-functionalized derivatives were synthesized from commercial (+)-sclareolide and evaluated for their cytotoxic, antimycotic, and antiviral activities. Their precursors were similarly evaluated. (C) 2010 Elsevier Masson SAS. All rights reserved.
• 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.