齐墩果-12-烯-3b,6b-二醇 | 41498-79-7

• 物质功能分类: 化学试剂 - 有机试剂 - 烯烃（环状与无环状）
• 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
• 中文名称: 齐墩果-12-烯-3b,6b-二醇
• 英文名称: 3β,6β-dihydroxyolean-12-ene
• 英文别名: daturadiol；oleanene-(12)-diol-(3β.6β)；(4aR)-8c.10c-Dihydroxy-2.2.4ar.6at.6bc.9.9.12ac-octamethyl-(8atH.12btH.14bcH)-Δ¹⁴-eicosahydro-picen；Oleanen-(12)-diol-(3β.6β)；(3S,4aR,5R,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,5-diol
• CAS: 41498-79-7
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: JYNBNJRQZZSLPN-NYVWVNPOSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  齐墩果-12-烯-3b,6b-二醇 在 吡啶 、 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-hydroxyolean-12-en-6-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以7 mg的产率得到齐墩果-12-烯-3b,6b-二醇
  参考文献：
  名称：

  5,6-环氧丙烷的酸催化主链重排及曼陀罗二醇的制备

  摘要：

  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）。

  DOI：

  10.1246/bcsj.57.2490

文献信息

• Three New Derivatives and Others Constituents from the Roots and Twigs of<i>Trilepisium madagascariense</i>DC
  作者：Yves P. Ango、Gilbert D. W. F. Kapche、Victor Kuete、Renameditswe Mapitse、Samuel O. Yeboah、Bonaventure T. Ngadjui

  DOI：10.1002/hlca.201600073

  日期：2016.8

  7‐tetrahydroxyflavanone (7), 2‐hydroxybenzoic acid (8), methyl 2,4‐dihydroxy‐6‐methylbenzoate (9), β‐amyrin (10), eurothridiol palmitate (11), and β‐sitosterol (12), were isolated from the AcOEt extract of the twigs and the roots of Trilepisium madagascariense. Acetylation of eurothridiol palmitate was carried out and a new acetylated derivative (13) was obtained. The structures of the isolated and acetylated

  三种新化合物，三乙黄酮（1），三乙二酮（2）和硬脂酸多aturadiol（3），以及九种已知化合物，2-羟基-4-[[（4-羟基-2--2-甲氧基-6-甲基苯甲酰基）氧基]- 6-甲基苯甲酸（4），六己酮（5），柚皮苷（6），3'，4'，5,7-四羟基黄酮（7），2-羟基苯甲酸（8），甲基2,4-二羟基-6-甲基苯甲酸甲酯（9），β -amyrin（10），棕榈酸eurothridiol（11），和β谷甾醇（12）是从树枝和马达加斯加t虫的根的AcOEt提取物中分离得到的。进行三乙二醇棕榈酸酯的乙酰化反应，得到新的乙酰化衍生物（13）。在光谱分析的基础上阐明了分离的和乙酰化的化合物的结构。使用Mueller - Hinton肉汤（MHB）和Mueller - Hinton琼脂（MHA）方法评估了所有这些化合物的抗菌活性。Trilepisdepsidone ， 2-羟基-4-[（4-羟基-2-甲氧基-6-甲基苯甲酰基）氧基]
• EPOXIDATION OF ALNUS-5-EN-3β-YL ACETATE AND CONVERSION OF DENDROPANOXIDE INTO DATURADIOL
  作者：Motoo Tori、Masaki Takai、Yuzo Matsumoto、Yoshihiko Moriyama、Takahiko Tsuyuki、Takeyoshi Takahashi、Akiko Itai、Yoichi Iitaka

  DOI：10.1246/cl.1983.527

  日期：1983.4.5

  Contrary to the reported literature, the main epoxide derived from alnus-5-en-3β-yl acetate (1) was shown to be a β-epoxide. Daturadiol (=olean-12-ene-3β,6β-diol) was prepared from dendropanoxide via 1 and its α-epoxide.

  与文献报道相反，从乙酸5-烯-3β-基乙酯（1）中衍生出的主要环氧化物被证明是β-环氧化物。通过1和其α-环氧化物从降冰片烷氧化物制备了莨菪二醇（=齐墩果-12-烯-3β,6β-二醇）。
• Functional Characterization of CYP716 Family P450 Enzymes in Triterpenoid Biosynthesis in Tomato
  作者：Shuhei Yasumoto、Hikaru Seki、Yuko Shimizu、Ery O. Fukushima、Toshiya Muranaka

  DOI：10.3389/fpls.2017.00021

  日期：——

  showed that CYP716A44 and CYP716A46 exhibited the ordinary C-28 oxidation activity against α-amyrin and β-amyrin to produce ursolic and oleanolic acids, respectively. Interestingly, one CYP716E subfamily enzyme, CYP716E26, exhibited the previously unreported C-6β hydroxylation activity against β-amyrin to produce a rare bioactive triterpenoid, daturadiol (olean-12-ene-3β,6β-diol). To determine the roles

  三萜类化合物是一组结构多样的专门代谢物，经常显示出有用的生物活性。这些化学物质是由植物中常见的前体2,3-氧化角鲨烯生物合成的。氧化角鲨烯环化酶（OSC）产生的碳骨架通常会被细胞色素P450单加氧酶（P450s）和UDP依赖性糖基转移酶修饰。这些生物合成酶有助于植物三萜的结构多样化。迄今为止，许多P450酶已被表征为三萜类氧化酶。其中，CYP716家族P450酶似乎已从多种植物家族中分离出来，似乎有助于三萜类化合物的结构多样化。许多CYP716家族P450酶已被表征为多功能三萜C-28氧化酶，可以将α-amyrin和β-amyrin分别氧化​​为广泛分布的三萜类乌索酸和齐墩果酸。番茄（Solanum lycopersicum）是世界上最重要的茄科作物之一。然而，关于其三萜生物合成的信息知之甚少。为了解番茄中三萜类生物合成的机理，我们集中研究了CYP716家族酶作为三萜类氧化酶的功能。我们从
• 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.
• 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）。