asmarine A

• 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: asmarine A
• 英文别名: (10S)-10-[2-[(1S,2R,4aR,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethyl]-9-hydroxy-10-methyl-1,3,5,7,9-pentazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene
• 化学式: C₂₅H₃₇N₅O
• 分子量: 423.602
• InChiKey: YUVFIHRLMIHDBO-BBDZFPCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  asmarine A 在 sodium thiosulfate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以100%的产率得到asmarine H
  参考文献：
  名称：

  Asmarines G and H and Barekol, Three New Compounds from the Marine Sponge Raspailia sp.

  摘要：

  Four asmarines, the known A and F and two new ones G and H, four diterpenes, the known chelodane, barekoxide, and zaatirin and a new one, barekol, and methyl 3-oxo-cholan-24-oate were isolated from the Kenyan sponge Raspailia sp. The structures of all these compounds were established on the basis of MS and NMR data, and the absolute configuration of barekol was determined from the CD measurements of its keto-derivative. The N-15 chemical shifts of the N atoms of the heterocycles of the asmarines were measured from N-15 HMBC experiments, and the influence of various structural features on the delta(N) values studied.

  DOI：

  10.1021/np030261x

文献信息

• Isolation and structure of cribrostatin 6
  申请人：Pettit R. George

  公开号：US20060173032A1

  公开（公告）日：2006-08-03

  Cribrostatin 6, a dark blue cancer cell growth inhibiting constituent of the Republic of Maldives marine sponge Cribrochalina sp. has been isolated, and its structure (shown below) elucidated, based on a combination of RMS, high field (500 MHz, HMBC, and GOESY experiments) 15N, 1 H- and 13C NMR, and X-ray crystal structure analyses. Cribrostatin 6 also was found to inhibit the growth of a number of pathogenic bacteria and fungi.

  马尔代夫共和国海洋海绵 Cribrochalina sp.中的一种深蓝色癌细胞生长抑制成分 Cribrostatin 6 已被分离出来，其结构（如下图所示）也已根据 RMS、高场（500 MHz、HMBC 和 GOESY 实验）15N.N.结合分析方法阐明、 1 H- 和 13C NMR 以及 X 射线晶体结构分析。研究还发现 Cribrostatin 6 能抑制多种致病细菌和真菌的生长。
• Asmarines A−F, Novel Cytotoxic Compounds from the Marine Sponge <i>Raspailia</i> Species
  作者：Tesfamariam Yosief、Amira Rudi、Yoel Kashman

  DOI：10.1021/np9902690

  日期：2000.3.1

  Three pairs of nitrogen-containing metabolites, asmarines A-F (1-6), were isolated from the Red Sea sponge Raspailia sp., collected in the Dahlak Archipelago, Eritrea. Although the first pair could fully be separated to give compounds 1 and 2, the other two pairs could only be enriched up to about 80% of one isomer. The structures of the new compounds were established by spectroscopic means. Besides the asmarines, methyl 3-oxo-cholan-24-oate (12) was also isolated. The absolute configuration of asmarine A (1) was determined on the basis of CD measurements of its unstable 18-oxo derivative (7) and mainly the Cotton effect of the dicarbonyl derivative (9) of chelodane (8). A O,N(7')-dimethyl derivative (10) and a second, unexpected, methylated product (11) were obtained from 2.
• CYTOTOXIC ALKALOID DERIVATIVES INCLUDING ASMARINE A AND B ISOLATED FROM A SPONGE
  申请人：Instituto Biomar S.A.

  公开号：EP1070067A1

  公开（公告）日：2001-01-24
• US6420357B1
  申请人：——

  公开号：US6420357B1

  公开（公告）日：2002-07-16
• US7317020B2
  申请人：——

  公开号：US7317020B2

  公开（公告）日：2008-01-08