mokkolactone | 4955-03-7

• 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: mokkolactone
• 英文别名: (3S,3aS,6aR,9aR,9bS)-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• CAS: 4955-03-7
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: UJADCNYXDHHISU-PEDHHIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  mokkolactone 在 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 溶剂黄146 为溶剂， 生成 去氢木香内酯
  参考文献：
  名称：

  TOTAL SYNTHESES OF MOKKO LACTONE, DEHYDROCOSTUS LACTONE, AND EREMANTHIN

  摘要：

  以1-oxoeudesm-2-eno-13,6α-内酯为原料，经过7步合成了一系列在A环上具有共同结构单元的愈创木酚内酯，如木香内酯、脱氢木香内酯和eremanthin。关键步骤涉及 1β-mesyloxyeudesm-4(14)-eno-13,6α-内酯的溶剂分解重排。

  DOI：

  10.1246/cl.1984.493
• 作为产物：
  描述：

  (11S)-1-oxoeudesm-2-eno-12,6α-lactone 在 吡啶 、 potassium acetate 、 lithium tri-t-butoxyaluminum hydride 、 间氯过氧苯甲酸 、 汞 、 锌 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 31.5h， 生成 mokkolactone
  参考文献：
  名称：

  Guaianolides as Immunomodulators. Synthesis and Biological Activities of Dehydrocostus Lactone, Mokko Lactone, Eremanthin, and Their Derivatives

  摘要：

  The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from I-a-santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an alpha-methylene gamma-lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.

  DOI：

  10.1021/np980092u

文献信息

• Alcohol absorption inhibitors from bay leaf ( Laurus nobilis ): structure-requirements of sesquiterpenes for the activity
  作者：Masayuki Yoshikawa、Hiroshi Shimoda、Toshiaki Uemura、Toshio Morikawa、Yuzo Kawahara、Hisashi Matsuda

  DOI：10.1016/s0968-0896(00)00127-9

  日期：2000.8

  ethanol-loaded rat, various sesquiterpenes having an alpha-methylene-gamma-butyrolactone moiety, costunolide (1), dehydrocostus lactone (2), zaluzanin D (3), reynosin (4), santamarine (5), 3alpha-acetoxyeudesma-1,4(15),11(13)-trien-12,6alpha-+ ++olide (6) and 3-oxoeudesma-1,4,11(13)-trien-12,6alpha-olide (7), were isolated as the active principle from the leaves of Laurus nobilis (bay leaf, laurel). In

  通过在抑制口服乙醇的大鼠血液乙醇升高方面具有抑制活性的生物测定指导分离，各种倍半萜具有α-亚甲基-γ-丁内酯部分，木香酚内酯（1），脱氢古斯内酯（2），扎鲁赞宁D（3），肌球蛋白（4），三mar（5），3alpha-acetoxyeudesma-1,4（15），11（13）-trien-12,6alpha- + ++ olide（6）和3-oxoeudesma-1,4,11（从月桂叶（月桂叶，月桂树）的叶子中分离出作为活性成分的13）-trien-12,6α-内酯（7）。为了表征活性的结构要求，由2合成了几种还原产物（2a-2d）和α-亚甲基-γ-丁内酯部分的氨基酸加合物（2e，2f），并且这些倍半萜烯具有抑制活性，连同α-亚甲基-γ-丁内酯（12）及其相关化合物（13-16），被检查。这些结果表明，具有α-亚甲基或α-甲基的γ-丁内酯或γ-丁内酯部分对于抑制乙醇吸收是必不可少的。由于1、
• Microbial Transformation of Sesquiterpene Lactones by the Fungi <i>Cunninghamella echinulata</i> and <i>Rhizopus oryzae</i>
  作者：Alejandro F. Barrero、J. Enrique Oltra、Délio S. Raslan、Dênia A. Saúde

  DOI：10.1021/np980520w

  日期：1999.5.1

  13-dihydrodehydrocostuslactone (12), a new natural product. R. oryzae converted 4 into both Delta11(13)-dihydrogenation and Delta10(14)-epoxidation products (16 and 17). Both fungi transformed 5 into (-)-16-(1-methyl-1-propenyl)eremantholanolide (13), providing experimental evidence for the biosynthesis of the eremantholide hemiketal unit. Compounds 3 and 6 were not metabolized by either fungus under the test conditions

  用倍半萜内酯（+）-木香内酯（1），（+）-菜青素（2），（+）-沙柳土内酯（3），（-）-脱氢木糖内酯（4），（进行了-）-lychnopholide（5）和（-）-eremantholide C（6）的制备。将1与棘孢梭菌一起孵育可得到Delta11（13）-二氢化和Delta1（10）-环氧化产物（7-10）。C. echinulata还水解2的侧链，并将4转化为新的天然产物（+）-11alpha，13-dihydrodehydrocostuslactone（12）。米曲霉将4转化为Delta11（13）-二氢和Delta10（14）-环氧化产物（16和17）。两种真菌都将5转化为（-）-16-（1-甲基-1-丙烯基）季戊四醇（13），为艾曼菊酯半缩酮单元的生物合成提供了实验证据。
• Developing new herbicide models from allelochemicals
  作者：Francisco A Macías、Juan C G Galindo、José M G Molinillo、Diego Castellano、Raúl F Velasco、David Chinchilla

  DOI：10.1002/(sici)1096-9063(199906)55:6<662::aid-ps3>3.0.co;2-q

  日期：1999.6
• Guaianolides as Immunomodulators. Synthesis and Biological Activities of Dehydrocostus Lactone, Mokko Lactone, Eremanthin, and Their Derivatives
  作者：Saori Yuuya、Hisahiro Hagiwara、Toshio Suzuki、Masayoshi Ando、Atsushi Yamada、Kouji Suda、Takao Kataoka、Kazuo Nagai

  DOI：10.1021/np980092u

  日期：1999.1.1

  The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from I-a-santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an alpha-methylene gamma-lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.
• TOTAL SYNTHESES OF MOKKO LACTONE, DEHYDROCOSTUS LACTONE, AND EREMANTHIN
  作者：Masayoshi Ando、Akio ONO、Kahei Takase

  DOI：10.1246/cl.1984.493

  日期：1984.4.5

  A series of guaianolides such as mokko lactone, dehydrocostus lactone, and eremanthin which posses a common structural unit in A ring have been synthesized from 1-oxoeudesm-2-eno-13,6α-lactone in 7 steps. The key step involves solvolytic rearrangement of 1β-mesyloxyeudesm-4(14)-eno-13,6α-lactone.

  以1-oxoeudesm-2-eno-13,6α-内酯为原料，经过7步合成了一系列在A环上具有共同结构单元的愈创木酚内酯，如木香内酯、脱氢木香内酯和eremanthin。关键步骤涉及 1β-mesyloxyeudesm-4(14)-eno-13,6α-内酯的溶剂分解重排。