daturadiol 3-monoacetate | 41498-81-1

• 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: daturadiol 3-monoacetate
• 英文别名: 3-O-acetyldaturadiol；acetic acid-(6β-hydroxy-oleanen-(12)-yl-(3β)-ester)；Essigsaeure-(6β-hydroxy-oleanen-(12)-yl-(3β)-ester)；3β-Acetoxy-oleanen-(12)-ol-(6β)；(4aR)-8c-Hydroxy-10c-acetoxy-2.2.4ar.6at.6bc.9.9.12ac-octamethyl-(8atH.12btH.14bcH)-Δ¹⁴-eicosahydro-picen；[(3S,4aR,5R,6aR,6bS,8aR,12aR,14aR,14bR)-5-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl] acetate
• CAS: 41498-81-1
• 化学式: C₃₂H₅₂O₃
• 分子量: 484.763
• InChiKey: KHNOTTSLMUNERG-FNTGSRHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  daturadiol 3-monoacetate 在 chromium(VI) oxide 、 溶剂黄146 、 苯 作用下， 生成 6-oxo-olean-12-en-3β-yl acetate
  参考文献：
  名称：

  Wine Antioxidant Polyphenols Inhibit the Proliferation of Human Prostate Cancer Cell Lines

  摘要：

  The effect of different wine antioxidant polyphenols (catechin, epicatechin, quercetin, and resveratrol) on the growth of three prostate cancer cell lines (LNCaP, PC3, and DU145) was investigated A dose- and time-dependent inhibition of cell growth by polyphenols was found at nanomolar concentrations. The proliferation of LNCaP and PC3 cells was preferentially inhibited by flavonoid's (catechin, epicatechin, and quercetin), whereas resveratrol was the most potent inhibitor of DU145 cell growth. Possible mechanisms of action were investigated. 1) The competition of polyphenols for androgen binding in LNCaP cells revealed significant interaction only in the case of high concentrations of quercetin, at least at five orders of magnitude higher than the concentrations needed for cell growth inhibition. All other phenols showed low interactions. 2) Oxygen species production after mitogen stimulation and H2O2 sensitivity of these cell lines did not correlate with the observed antiproliferative effects, ruling out such a mode of action. 3) NO production revealed two different patterns. LNCaP and DU145 cells produced high concentrations of NO, whereas PC3 cells produced low concentrations. Phorbol ester stimulation of cells did not reveal any additional effect in LNCaP and DU145 cells, whereas it enhanced the secretion of NO in PC3 cells. Polyphenols decreased NO secretion. This effect correlates with their antiproliferative action and the inhibition of inducible NO synthase. It is therefore proposed that the antiproliferative effect of polyphenols is mediated through the modulation of NO production. rn conclusion, our data show a direct inhibitory effect of low concentrations of antioxidant wine phenols on the proliferation of human prostate cancer cell fines mediated by the production of NO, further suggesting potential beneficial effects of wine and other phenol-containing foods or drinks for the control of prostate cancer cell growth.

  DOI：

  10.1207/s15327914nc372_16
• 作为产物：
  描述：

  3β.6β-diacetoxy-oleanen-(12)-al-(28) 在 吡啶 、 sodium ethanolate 作用下， 生成 daturadiol 3-monoacetate
  参考文献：
  名称：

  Wine Antioxidant Polyphenols Inhibit the Proliferation of Human Prostate Cancer Cell Lines

  摘要：

  The effect of different wine antioxidant polyphenols (catechin, epicatechin, quercetin, and resveratrol) on the growth of three prostate cancer cell lines (LNCaP, PC3, and DU145) was investigated A dose- and time-dependent inhibition of cell growth by polyphenols was found at nanomolar concentrations. The proliferation of LNCaP and PC3 cells was preferentially inhibited by flavonoid's (catechin, epicatechin, and quercetin), whereas resveratrol was the most potent inhibitor of DU145 cell growth. Possible mechanisms of action were investigated. 1) The competition of polyphenols for androgen binding in LNCaP cells revealed significant interaction only in the case of high concentrations of quercetin, at least at five orders of magnitude higher than the concentrations needed for cell growth inhibition. All other phenols showed low interactions. 2) Oxygen species production after mitogen stimulation and H2O2 sensitivity of these cell lines did not correlate with the observed antiproliferative effects, ruling out such a mode of action. 3) NO production revealed two different patterns. LNCaP and DU145 cells produced high concentrations of NO, whereas PC3 cells produced low concentrations. Phorbol ester stimulation of cells did not reveal any additional effect in LNCaP and DU145 cells, whereas it enhanced the secretion of NO in PC3 cells. Polyphenols decreased NO secretion. This effect correlates with their antiproliferative action and the inhibition of inducible NO synthase. It is therefore proposed that the antiproliferative effect of polyphenols is mediated through the modulation of NO production. rn conclusion, our data show a direct inhibitory effect of low concentrations of antioxidant wine phenols on the proliferation of human prostate cancer cell fines mediated by the production of NO, further suggesting potential beneficial effects of wine and other phenol-containing foods or drinks for the control of prostate cancer cell growth.

  DOI：

  10.1207/s15327914nc372_16

文献信息

• Acid-catalyzed Backbone Rearrangement of 5,6-Epoxyalnusanes and Preparation of Daturadiol
  作者：Motoo Tori、Masaki Takai、Yuzo Matsumoto、Yoshihiko Moriyama、Takahiko Tsuyuki、Takeyoshi Takahashi、Hiraku Ohnishi、Akiko Itai、Yoichi Iitaka

  DOI：10.1246/bcsj.57.2490

  日期：1984.9

  Epoxidation of alnus-5-en-3β-yl acetate with m-chloroperbenzoic acid gave a 5β,6β-epoxide as a main product together with a 5α,6α-epoxide as a minor product. Treatment of the α-epoxide with BF3·OEt2 afforded a 1(10),5-diene and a mixture of 6α-hydroxy-12- and -18-ene derivatives. The 12-ene was converted into daturadiol (=olean-12-ene-3β,6β-diol).

  用间氯过苯甲酸环氧化 alnus-5-en-3β-yl 乙酸酯得到 5β,6β-环氧化物作为主要产物和 5α,6α-环氧化物作为次要产物。用BF3·OEt2 处理α-环氧化物得到1(10),5-二烯和6α-羟基-12-和-18-烯衍生物的混合物。12-烯转化为曼陀罗二醇（=olean-12-ene-3β,6β-diol）。
• Wine Antioxidant Polyphenols Inhibit the Proliferation of Human Prostate Cancer Cell Lines
  作者：Marilenna Kampa、Anastassia Hatzoglou、George Notas、Athina Damianaki、Efstathia Bakogeorgou、Claudia Gemetzi、Elias Kouroumalis、Pierre-Marie Martin、Elias Castanas

  DOI：10.1207/s15327914nc372_16

  日期：2000.7

  The effect of different wine antioxidant polyphenols (catechin, epicatechin, quercetin, and resveratrol) on the growth of three prostate cancer cell lines (LNCaP, PC3, and DU145) was investigated A dose- and time-dependent inhibition of cell growth by polyphenols was found at nanomolar concentrations. The proliferation of LNCaP and PC3 cells was preferentially inhibited by flavonoid's (catechin, epicatechin, and quercetin), whereas resveratrol was the most potent inhibitor of DU145 cell growth. Possible mechanisms of action were investigated. 1) The competition of polyphenols for androgen binding in LNCaP cells revealed significant interaction only in the case of high concentrations of quercetin, at least at five orders of magnitude higher than the concentrations needed for cell growth inhibition. All other phenols showed low interactions. 2) Oxygen species production after mitogen stimulation and H2O2 sensitivity of these cell lines did not correlate with the observed antiproliferative effects, ruling out such a mode of action. 3) NO production revealed two different patterns. LNCaP and DU145 cells produced high concentrations of NO, whereas PC3 cells produced low concentrations. Phorbol ester stimulation of cells did not reveal any additional effect in LNCaP and DU145 cells, whereas it enhanced the secretion of NO in PC3 cells. Polyphenols decreased NO secretion. This effect correlates with their antiproliferative action and the inhibition of inducible NO synthase. It is therefore proposed that the antiproliferative effect of polyphenols is mediated through the modulation of NO production. rn conclusion, our data show a direct inhibitory effect of low concentrations of antioxidant wine phenols on the proliferation of human prostate cancer cell fines mediated by the production of NO, further suggesting potential beneficial effects of wine and other phenol-containing foods or drinks for the control of prostate cancer cell growth.