3α-methoxyserrat-14-en-21β-ol

• 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: 3α-methoxyserrat-14-en-21β-ol
• 英文别名: PJ-1；(1S,6R,8R,11R,12S,15S,16R,19R,21R)-19-methoxy-1,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.03,12.06,11.016,21]tricos-3-en-8-ol
• 化学式: C₃₁H₅₂O₂
• 分子量: 456.753
• InChiKey: HADVFQOSVABMHT-ZSMMNZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3α-methoxyserrat-14-en-21β-ol 在 吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 4-O-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl] 1-O-[(1S,6R,8R,11R,12S,15S,16R,19R,21R)-19-methoxy-1,7,7,11,16,20,20-heptamethyl-8-pentacyclo[13.8.0.03,12.06,11.016,21]tricos-3-enyl] butanedioate
  参考文献：
  名称：

  Conjugates of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) as cancer chemopreventive agents

  摘要：

  3 alpha-Methoxyserrat-14-en-21 beta-ol (PJ-1) and 3 beta-methoxyserrat-14-en-21 beta-ol (PJ-2) were conjugated with well-known phenolic compounds, narigenin, hesperetin, genistein, and daidzein (1-8). Other conjugates of PJ-2-3,5-dihydroxy-4-methoxybenzoic acid (9), PJ-2 pyrogallol (10), and derivatives of PJ-1, PJ-2-3,3-dimethyl-succinates (11, 12), PJ-1, PJ-2 succinates (13, 14), PJ-2 glycine (15), PJ-2 piperidine acetic acid (16), and PJ-1 epoxy-3,3-dimethyl-succinate (17) were tested for their inhibitory effects on Epstein Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The inhibitory effects of 11 (IC50 = 251),12 (IC50 = 248), and 17 (IC50= 230 mol ratio/32 pmol/TPA), were 2-fold stronger than those of the other compounds such as oleanolic acid (IC50 = 449). Compounds 10, 11, and 17 inhibited mouse skin tumor promotion in an in vivo two-stage carcinogenesis model. The in vivo two-stage mouse-skin carcinogenesis test employed 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.062

文献信息

• The neutral triterpenes of the bark of Picea sitchensis (Sitka spruce)
  作者：J.P. Kutney、I.H. Rogers、J.W. Rowe

  DOI：10.1016/s0040-4020(01)82906-9

  日期：——

  Eight neutral triterpenes have been isolated from Sitka spruce bark. These compouds were shown to belong to the unique serratenediol family in which ring C is 7-membered. The two major components have the structure 3β-methoxy-21β-hydroxy-Δ14-serratene (VIII) and the corresponding 3α isomer (IX). A third compound was found to be 3α-methoxy-21β-hydroxy-Δ13-serratene (XXIII) which is the first reported

  从锡特卡云杉树皮中分离出八种中性三萜。这些化合物显示属于环C为7元的独特的锯齿二醇家族。两个主要成分具有下述结构3β甲氧基21β羟基Δ 14 -serratene（VIII）和相应的异构体3α（IX）。第三个化合物被发现是3α甲氧基21β羟基Δ 13 -serratene（XXIII），这是首次报道在这个系列具有Δ的化合物的天然发生13双键。还分离了21-episerratenediol（VII）和3β-甲氧基-21-酮- Δ 14 -serratene（V）。
• Novel 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2)-curcumin, kojic acid, quercetin, and baicalein conjugates as HIV agents
  作者：Reiko Tanaka、Hiroko Tsujii、Takeshi Yamada、Tetsuya Kajimoto、Fumio Amano、Junya Hasegawa、Yoshio Hamashima、Manabu Node、Kayoko Katoh、Yutaka Takebe

  DOI：10.1016/j.bmc.2009.05.049

  日期：2009.7

  Sixteen novel compounds; 3 alpha-methoxyserrat-14-en-21 beta-ol (1) and 3 beta-methoxyserrat-14-en-21 beta-ol (2) and their curcumin, kojic acid, quercetin, and baicalein conjugates (3)-(18) were designed, synthesized, and evaluated for in vitro anti-HIV-1 reverse transcriptase (RT) activity in infected C8166-CCR5 cells, a human CD4(+) T-lymphocyte cell line. Among them, kojic acid derivatives, 9-12 showed significant biological activity. In particular, the compound 13, the conjugate of two molecules of 3 alpha-methoxyserrat-14-en-21 beta-ol (1) and one molecule of kojic acid, exerted significant anti-HIV activity with an EC50 value of 0.12 mu g/mL. (C) 2009 Elsevier Ltd. All rights reserved.
• Two serratane triterpenes from the stem bark of Picea jezoensis var. hondoensis
  作者：Reiko Tanaka、Kazuhiro Tsujimoto、Shunyo Matsunaga

  DOI：10.1016/s0031-9422(99)00318-0

  日期：1999.12

  Two serratane triterpenoids were isolated from the stem bark of Picea jezoenis var. hondoensis, together with two known compounds, 3 beta-methoxyserrat-14-en-21-one and 3 beta-methoxyserrat-14-en-21 alpha-ol. The serratane triterpenoids were characterized as 14 beta,15 beta-epoxy-3 alpha-methoxyserratan-21 beta-ol and 3 alpha-methoxy-21 beta-hydroxyserrat-14-en-16-one, on the basis of chemical and spectroscopic evidence; (C) 1999 Elsevier Science Ltd. All rights reserved.
• Bioactive Triterpenoids from the Stem Bark of<i>Picea glehni</i>
  作者：Reiko Tanaka、Yoshitaka Kinouchi、Harukuni Tokuda、Hoyoku Nishino、Shunyo Matsunaga

  DOI：10.1055/s-2000-8886

  日期：2000.10

  Two new triterpenoids, 3α-methoxyserrat-14-en-21β-yl formate (1), and 24-methylcycloartenone (2), were isolated from the stem bark of Picea glehni (Fr. Schm.) Masters together with three known triterpenoids, 3α-methoxyserrat-14-en-21β-ol, 3β-methoxyserrat-14-en-21β-ol, and piceanonol A. Compounds 1, 2, and a synthetic sample, 3α-methoxyserrat-13-en-21β-yl formate showed potent inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA).
• Conjugates of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) as cancer chemopreventive agents
  作者：Reiko Tanaka、Hiroko Tsujii、Takeshi Yamada、Tetsuya Kajimoto、Harukuni Tokuda、Takanari Arai、Nobutaka Suzuki、Junya Hasegawa、Yoshio Hamashima、Manabu Node

  DOI：10.1016/j.ejmech.2011.04.062

  日期：2011.8

  3 alpha-Methoxyserrat-14-en-21 beta-ol (PJ-1) and 3 beta-methoxyserrat-14-en-21 beta-ol (PJ-2) were conjugated with well-known phenolic compounds, narigenin, hesperetin, genistein, and daidzein (1-8). Other conjugates of PJ-2-3,5-dihydroxy-4-methoxybenzoic acid (9), PJ-2 pyrogallol (10), and derivatives of PJ-1, PJ-2-3,3-dimethyl-succinates (11, 12), PJ-1, PJ-2 succinates (13, 14), PJ-2 glycine (15), PJ-2 piperidine acetic acid (16), and PJ-1 epoxy-3,3-dimethyl-succinate (17) were tested for their inhibitory effects on Epstein Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The inhibitory effects of 11 (IC50 = 251),12 (IC50 = 248), and 17 (IC50= 230 mol ratio/32 pmol/TPA), were 2-fold stronger than those of the other compounds such as oleanolic acid (IC50 = 449). Compounds 10, 11, and 17 inhibited mouse skin tumor promotion in an in vivo two-stage carcinogenesis model. The in vivo two-stage mouse-skin carcinogenesis test employed 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. (C) 2011 Elsevier Masson SAS. All rights reserved.