astin M

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: astin M
• 英文别名: (3S,7R,10S,13S,16S,18S)-18-chloro-3,13-diethyl-10-(hydroxymethyl)-7-phenyl-1,4,8,11,14-pentazabicyclo[14.3.0]nonadecane-2,5,9,12,15-pentone
• 化学式: C₂₅H₃₄ClN₅O₆
• 分子量: 536.028
• InChiKey: WHXRVUJVKSXTNA-OROIIQQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  astin M 在 盐酸 、 水 作用下， 反应 24.0h， 生成 L-丝氨酸
  参考文献：
  名称：

  Astins K–P, six new chlorinated cyclopentapeptides from Aster tataricus

  摘要：

  During further investigation on the methanol extract of roots and rhizomes of Aster tataricus, six new chlorinated cyclopentapeptides, designated as astins K-P (9-14), together with eight known derivatives, astins A-H (1-8), were isolated. Structures of the new cyclopeptides were established using extensive spectroscopic methods, and the absolute configurations were determined by the advanced Marfey's method. Astin P (14) represents a unique cyclopentapeptide linking as cyclo-(L-Pro (Cl-2)(1)-L-allo-Thr(2)-L-Ser(3)-L-beta-Phe(4)-L-Ava(5)). Astin B(2) showed cytotoxicity against BGC-823 cell with IC50 value of 19.2 mu g/ml. Astin C (3) exhibited cytotoxicity on HCT-116 and BGC-823 cells with IC50 values of 13.4 and 3.3 mu g/ml, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.006
• 作为产物：
  描述：

  astin C 在 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以39%的产率得到(5S,9R,12S,15S,17aS)-5,15-Diethyl-12-hydroxymethyl-9-phenyl-3,5,6,9,10,12,13,15,16,17a-decahydro-8H-3a,6,10,13,16-pentaaza-cyclopentacyclohexadecene-4,7,11,14,17-pentaone
  参考文献：
  名称：

  Cyclic Peptides from Higher Plants. XXVIII. Antitumor Activity and Hepatic Microsomal Biotransformation of Cyclic Pentapeptides, Astins, from Aster tataricus.

  摘要：

  对从紫菀根中分离出的环状五肽类化合物阿司汀对肉瘤180A的抗肿瘤活性进行了研究。对通过化学转化制备的二氯脯氨酸残基的各种同系物以及大鼠肝脏微粒体生物转化进行的活性研究表明，阿司汀A、B和C的1,2-顺式二氯脯氨酸残基在阿司汀的抗肿瘤活性中起着重要作用。

  DOI：

  10.1248/cpb.44.1026

文献信息

• Astins K–P, six new chlorinated cyclopentapeptides from Aster tataricus
  作者：Hui-Min Xu、Guang-Zhi Zeng、Wen-Bing Zhou、Wen-Jun He、Ning-Hua Tan

  DOI：10.1016/j.tet.2013.07.006

  日期：2013.9

  During further investigation on the methanol extract of roots and rhizomes of Aster tataricus, six new chlorinated cyclopentapeptides, designated as astins K-P (9-14), together with eight known derivatives, astins A-H (1-8), were isolated. Structures of the new cyclopeptides were established using extensive spectroscopic methods, and the absolute configurations were determined by the advanced Marfey's method. Astin P (14) represents a unique cyclopentapeptide linking as cyclo-(L-Pro (Cl-2)(1)-L-allo-Thr(2)-L-Ser(3)-L-beta-Phe(4)-L-Ava(5)). Astin B(2) showed cytotoxicity against BGC-823 cell with IC50 value of 19.2 mu g/ml. Astin C (3) exhibited cytotoxicity on HCT-116 and BGC-823 cells with IC50 values of 13.4 and 3.3 mu g/ml, respectively. (C) 2013 Elsevier Ltd. All rights reserved.
• Cyclic Peptides from Higher Plants. XXVIII. Antitumor Activity and Hepatic Microsomal Biotransformation of Cyclic Pentapeptides, Astins, from Aster tataricus.
  作者：Hiroshi MORITA、Shinji NAGASHIMA、Yuki UCHIUMI、Osamu KUROKI、Koichi TAKEDA、Hideji ITOKAWA

  DOI：10.1248/cpb.44.1026

  日期：——

  Antitumor activities on Sarcoma 180A of a series of cyclic pentapeptides, astins, isolated from the roots of Aster tataricus, were examined. The activities on various congeners of the dichlorinated proline residues prepared by chemical conversion and a hepatic microsomal biotransformation in rats suggested that 1, 2-cis dichlorinated proline residues of astins A, B and C play an important role in the antitumor activity of astins.

  对从紫菀根中分离出的环状五肽类化合物阿司汀对肉瘤180A的抗肿瘤活性进行了研究。对通过化学转化制备的二氯脯氨酸残基的各种同系物以及大鼠肝脏微粒体生物转化进行的活性研究表明，阿司汀A、B和C的1,2-顺式二氯脯氨酸残基在阿司汀的抗肿瘤活性中起着重要作用。