agosterol A | 213549-32-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: agosterol A
• 英文别名: [(3S,4R,5S,6S,9R,10R,11R,13R,14R,17R)-4,6-diacetyloxy-11-hydroxy-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 213549-32-7
• 化学式: C₃₃H₅₂O₈
• 分子量: 576.771
• InChiKey: SUIRSZOPEPPNGJ-JGEDILIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

制备方法与用途

agostol A是从海绵中分离得到的。

反应信息

• 作为反应物：
  描述：

  agosterol A 在 2,6-二甲基吡啶 、 四溴化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以2.6 mg的产率得到Acetic acid (3S,4R,5S,6S,9R,10R,11R,13R,14R,17R)-3,4-diacetoxy-17-((S)-2-bromo-1,5-dimethyl-hexyl)-11-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl ester
  参考文献：
  名称：

  Reversal of multidrug resistance in human carcinoma cell line by agosterols, marine spongean sterols

  摘要：

  We have isolated agosterol A (1) from a marine sponge of Spongia sp. as a reversing substance to multidrug resistance (MDR) in human carcinoma cell lines, KB-CZ and KB-CV60, overexpressing P-glycoprotein and MRP, respectively. Further investigation led us to isolate analogous sterols, agosterols B (2), C (5), A(4) (7), D-2 (10), A(5) (13) and C-6 (14) from the same sponge and determine their structures. From the structure-activity relationship study, each of the 3,4,6-acetoxyl groups and 11,22-hydroxyl groups was elucidated to be crucial for reversing MDR in tumor cells. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00870-4
• 作为产物：
  描述：

  O-methoxymethyl-ergosterol 在 吡啶 、 2,6-二甲基吡啶 、 lead(IV) acetate 、 lithium aluminium tetrahydride 、 dimethyl sulfide borane 、 diamide 、 mercury(II) diacetate 、 四丁基氟化铵 、 氟化氢吡啶 、 臭氧 、 magnesium 、 溶剂黄146 、 间氯过氧苯甲酸 、 三甲基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 129.5h， 生成 agosterol A
  参考文献：
  名称：

  Total Synthesis of Agosterol A: an MDR-Modulator from a Marine Sponge

  摘要：

  The first total synthesis of agosterol A, a modulator of multidrug resistance (MDR) mediated by P-gp and MRP1, and isolated from a marine sponge, was achieved from ergosterol by utilizing a regioselective epoxy-cleavage reaction and regioselective dehydroxylation as the key reactions.

  DOI：

  10.1002/1521-3765(20010618)7:12<2663::aid-chem26630>3.0.co;2-u

文献信息

• Agosterol A, a novel polyhydroxylated sterol acetate reversing multidrug resistance from a marine sponge of Spongia sp.
  作者：Shunji Aoki、Yasuhiro Yoshioka、Yasuhisa Miyamoto、Kouichi Higuchi、Andi Setiawan、Nobutoshi Murakami、Zhe-Sheng Chen、Tomoyuki Sumizawa、Shin-ichi Akiyama、Motomasa Kobayashi

  DOI：10.1016/s0040-4039(98)01336-7

  日期：1998.8

  Agosterol A (1) has been isolated from a marine sponge of Spongia sp. and the absolute stereo-structure elucidated. Agosterol A (1) is a novel polyhydroxylated sterol acetate, which completely reverses multidrug resistance in human carcinoma cells caused by overexpression of two kinds of membrane glycoprotein.

  Agosterol A（1）已从的海绵中分离海绵Spongia藻。并阐明了绝对立体结构。Agosterol A（1）是一种新型的多羟基乙酸甾醇酯，可完全逆转由两种膜糖蛋白过表达引起的人类癌细胞的多药耐药性。
• Total Synthesis of Agosterol A: an MDR-Modulator from a Marine Sponge
  作者：Nobutoshi Murakami、Masanori Sugimoto、Mari Morita、Motomasa Kobayashi

  DOI：10.1002/1521-3765(20010618)7:12<2663::aid-chem26630>3.0.co;2-u

  日期：2001.6.18

  The first total synthesis of agosterol A, a modulator of multidrug resistance (MDR) mediated by P-gp and MRP1, and isolated from a marine sponge, was achieved from ergosterol by utilizing a regioselective epoxy-cleavage reaction and regioselective dehydroxylation as the key reactions.
• Reversal of multidrug resistance in human carcinoma cell line by agosterols, marine spongean sterols
  作者：Shunji Aoki、Andi Setiawan、Yasuhiro Yoshioka、Kouichi Higuchi、Ritsuko Fudetani、Zhe-Sheng Chen、Tomoyuki Sumizawa、Shin-ichi Akiyama、Motomasa Kobayashi

  DOI：10.1016/s0040-4020(99)00870-4

  日期：1999.12

  We have isolated agosterol A (1) from a marine sponge of Spongia sp. as a reversing substance to multidrug resistance (MDR) in human carcinoma cell lines, KB-CZ and KB-CV60, overexpressing P-glycoprotein and MRP, respectively. Further investigation led us to isolate analogous sterols, agosterols B (2), C (5), A(4) (7), D-2 (10), A(5) (13) and C-6 (14) from the same sponge and determine their structures. From the structure-activity relationship study, each of the 3,4,6-acetoxyl groups and 11,22-hydroxyl groups was elucidated to be crucial for reversing MDR in tumor cells. (C) 1999 Elsevier Science Ltd. All rights reserved.