hedychilactone A | 361483-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: hedychilactone A
• 英文别名: (3E)-3-[2-[(1R,3S,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]oxolan-2-one
• CAS: 361483-29-6
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: NTDYMFJJFRUEDG-LAABLSLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  hedychilactone A 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 2-[2-((1R,3S,4aS,8aS)-3-Hydroxy-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-eth-(E)-ylidene]-butane-1,4-diol
  参考文献：
  名称：

  Antiinflammatory Principles and Three New Labdane-Type Diterpenes, Hedychilactones A, B, and C, from the Rhizome of Hedychium coronarium Koeng

  摘要：

  DOI：

  10.3987/com-01-s(k)10
• 作为产物：
  描述：

  龙涎酮 在 叔丁基过氧化氢 、 sodium tetrahydroborate 、 selenium(IV) oxide 、 草酰氯 、 sodium hydride 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 hedychilactone A
  参考文献：
  名称：

  （+）-七氢内酯A及其类似物（+）-香紫苏内酯的合成及生物活性。

  摘要：

  已通过有效途径由（+）-香紫苏内酯合成了天然产物Hechichilactone A（3）。两种合成中间体10和12对五种癌细胞系，人脐静脉内皮细胞（HUVEC）和一氧化氮（NO）产生了强大的生长抑制作用。特别地，化合物15显示出对HUVEC生长的选择性抑制活性，而在测试的癌细胞系中没有任何细胞毒性。

  DOI：

  10.1016/j.bmcl.2005.12.009

文献信息

• Concise Syntheses of Coronarin A, Coronarin E, Austrochaparol and Pacovatinin A
  作者：Takahiro Miyake、Keisuke Uda、Masako Kinoshita、Mikio Fujii、Hiroyuki Akita

  DOI：10.1248/cpb.56.398

  日期：——

  Total syntheses of (+)-coronarin A (1), (+)-coronarin E (2), (+)-austrochaparol (3) and (+)-pacovatinin A (4) were achieved from the synthetic (+)-albicanyl acetate (6). Dess–Martin oxidation of (+)-albicanol (5) derived from the chemoenzymatic product (6) gave an aldehyde (7), which was subjected to Julia one-pot olefination using β-furylmethyl-heteroaromatic sulfones (8 or 9 ) gave (+)-trans coronarin E (2) and (+)-cis coronarin E (12) with high cis-selectivity. The synthesis of (+)-coronarin A (1) from (+)-trans coronarin E (2) was achiev-ed, while (+)-cis coronarin E (12) was converted to the natural products (+)-(5S,9S,10S)-15,16-epoxy-8(17),13(16),14-labdatriene (13) and (+)-austrochaparol (3). By the asymmetric synthesis of (+)-3, the absolute structure of (+)-3 was determined to be 5S, 7R, 9R, 10S configurations. Homologation of (+)-albicanol (5) followed by allylic oxidation gave (7α)-hydroxy nitrile (17), which was finally converted to the natural (+)-pacovatinin A (4) in 8 steps from (+)-albicanol (5).

  从合成产物(+)-albicanyl acetate (6)中获得了(+)-coronarin A (1)、(+)-coronarin E (2)、(+)-austrochaparol (3)和(+)-pacovatinin A (4)的完全合成。(+)-albicanol (5)的Dess-Martin氧化反应来自化学酶产物(6)，生成醛(7)，后者与β-呋喃甲基杂芳砜(8或9)进行Julia一锅法烯化反应，得到具有高顺式选择性的(+)-反式coronarin E (2)和(+)-顺式coronarin E (12)。从(+)-反式coronarin E (2)中获得了(+)-coronarin A (1)的合成，而(+)-顺式coronarin E (12)则转化为天然产物(+)-(5S,9S,10S)-15,16-epoxy-8(17),13(16),14-labdatriene (13)和(+)-austrochaparol (3)。通过(+)-3的不对称合成，确定(+)-3的绝对结构为5S,7R,9R,10S构型。(+)-albicanol (5)的同分异构化反应后，发生烯丙基氧化反应，生成(7α)-
• Pacovatinins A−C, New Labdane Diterpenoids from the Seeds of <i>Renealmia </i><i>e</i><i>xaltata</i>
  作者：Mitsuhiro Sekiguchi、Hideyuki Shigemori、Ayumi Ohsaki、Jun'ichi Kobayashi

  DOI：10.1021/np010097i

  日期：2001.8.1

  Three new labdane diterpenoids, pacovatinins A-C (1-3), were isolated from seeds of the Brazilian medicinal plant Renealmia exaltata ("Pacová-catinga"), and their structures including absolute configurations were elucidated by spectroscopic data and a modified Mosher method.

  从巴西药用植物雷尼阿米氏菌（“Pacová-catinga”）的种子中分离出三种新的拉丹烷二萜类化合物，即pacovatinins AC（1-3），并通过光谱数据和改良的Mosher方法阐明了它们的结构，包括绝对构型。
• Antiinflammatory Principles and Three New Labdane-Type Diterpenes, Hedychilactones A, B, and C, from the Rhizome of Hedychium coronarium Koeng
  作者：Masayuki Yoshikawa、Hisashi Matsuda、Toshio Morikawa、Yasuko Sakamoto、Iwao Toguchida

  DOI：10.3987/com-01-s(k)10

  日期：——
• Synthesis and biological activity of (+)-hedychilactone A and its analogs from (+)-sclareolide
  作者：Sangtae Oh、In Howa Jeong、Woon-Seob Shin、Qian Wang、Seokjoon Lee

  DOI：10.1016/j.bmcl.2005.12.009

  日期：2006.3

  has been synthesized from (+)-sclareolide by an efficient route. Two of the synthetic intermediates, 10 and 12, have shown strong growth inhibition effects against five cancer cell lines, human umbilical vein endothelial cell (HUVEC) and nitric oxide (NO) production. In particular, compound 15 showed selective inhibition activity against HUVEC growth without any cytotoxicity among tested cancer cell

  已通过有效途径由（+）-香紫苏内酯合成了天然产物Hechichilactone A（3）。两种合成中间体10和12对五种癌细胞系，人脐静脉内皮细胞（HUVEC）和一氧化氮（NO）产生了强大的生长抑制作用。特别地，化合物15显示出对HUVEC生长的选择性抑制活性，而在测试的癌细胞系中没有任何细胞毒性。
• Labdane-type Diterpenes with Inhibitory Effects on Increase in Vascular Permeability and Nitric Oxide Production from Hedychium coronarium
  作者：Hisashi Matsuda、Toshio Morikawa、Yasuko Sakamoto、Iwao Toguchida、Masayuki Yoshikawa

  DOI：10.1016/s0968-0896(02)00121-9

  日期：2002.8

  The methanolic extract front the rhizome of Hedychium coronarium Was found to inhibit the increase in vascular permeability induced by acetic acid in mice and nitric oxide production in lipopolysaccharide-activated Mouse peritoneal macrophages. Front the methanolic extract, three new labdane-type diterpenes, hedychilactones A, 13, and C, were isolated together with six known diterpenes. The structures of hedychilactones were elucidated on the basis of chemical and physicochemical evidence. The diterpene constituents showed inhibitory effects on the increase in vascular permeability, nitric oxide production, and inducible nitric oxide synthase induction. (C) 2002 Published by Elsevier Science Ltd.