hydroxyhopanone | 1981-81-3

• 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: hydroxyhopanone
• 英文别名: 3-oxo-22-hydroxyhopane；22-hydroxyhopan-3-one；22-hydroxyhopanone；22-hydroxy-A'-neo-gammaceran-3-one；22-Hydroxy-A'-neo-gammaceran-3-on；22-Hydroxy-17β,21β-hopanon-(3)；(3S,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-2,3,3a,4,5,6,7,7a,10,11,11b,12,13,13a-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
• CAS: 1981-81-3
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: NVNUNRUPWXZKAL-YKHKZODKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  hydroxyhopanone 在 硫酸 、 溶剂黄146 作用下， 生成 hop-17(21)-en-3-one
  参考文献：
  名称：

  Fazakerley et al., Journal of the Chemical Society, 1959, p. 1877,1883

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-Acetoxy-22-hydroxy-hopan 在 chromium(VI) oxide 、 sodium hydroxide 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 hydroxyhopanone
  参考文献：
  名称：

  Cerny,J. et al., Chemische Berichte, 1963, vol. 96, p. 3021 - 3023

  摘要：

  DOI：

文献信息

• Partial synthesis of dihydrothysanolactone.
  作者：Norio Aimi、Kazuhiro Kawada、Yuko Nagasato、Shinichiro Sakai、Joju Haginiwa

  DOI：10.1248/cpb.30.1098

  日期：——

  Dihydrothysanolactone (2), the dihydro derivative of a novel triterpene thysanolactone (1), was synthesized from an easily available pentacyclic triterpene, hydroxyhopanone (3).

  二氢thysanolactone（2）是一种新型三萜类化合物thysanolactone（1）的二氢衍生物，由一种容易获得的五环三萜类化合物羟基藿内酯（3）合成。
• The Configuration at C–21 of Hydroxyhopanone
  作者：Kazuo Sekiguchi、Hiroaki Kanemoto、Yoji Hirao、Takahiko Tsuyuki、Takeyoshi Takahashi

  DOI：10.1246/bcsj.47.1781

  日期：1974.7

  Hydroxyhopanone (1) was converted via two alternative routes (1→9→11a→12→14→15→16 and 1→10→17→18→19→20) to A-neohop-21-ene (16) and A-neohop-3-ene (20), respectively. These unsaturated hydrocarbons (16 and 20) were found to be identical; this provided evidence to confirm the 21β-H configuration for 1.

  羟基茄酮（1）通过两种替代途径（1→9→11a→12→14→15→16 和 1→10→17→18→19→20 ）分别转化为 A-neohop-21-ene (16) 和 A-neohop-3-ene (20)。这些不饱和碳氢化合物（16 和 20）被发现是相同的；这为证实 1 的 21β-H 构型提供了证据。
• Characterization of Radical SAM Adenosylhopane Synthase, HpnH, which Catalyzes the 5 <i>′</i> ‐Deoxyadenosyl Radical Addition to Diploptene in the Biosynthesis of C ₃₅ Bacteriohopanepolyols
  作者：Shusuke Sato、Fumitaka Kudo、Michel Rohmer、Tadashi Eguchi

  DOI：10.1002/anie.201911584

  日期：2020.1.2

  Adenosylhopane is a crucial intermediate in the biosynthesis of bacteriohopanepolyols, which are widespread prokaryotic membrane lipids. Herein, it is demonstrated that reconstituted HpnH, a putative radical S-adenosyl-l-methionine (SAM) enzyme, commonly encoded in the hopanoid biosynthetic gene cluster, converts diploptene into adenosylhopane in the presence of SAM, flavodoxin, flavodoxin reductase, and NADPH

  腺苷紫杉醇是细菌紫杉醇多元醇的生物合成中的关键中间体，而细菌紫杉醇多元醇是广泛的原核生物膜脂质。在此，证明了重组的HpnH（一种公认的自由基S-腺苷-1-甲硫氨酸（SAM）酶，通常在hopanoid生物合成基因簇中编码）在SAM，黄酮毒素，黄酮毒素还原酶和NADPH的存在下将二萜烯转化为腺苷。 。酶促反应产物的NMR谱图与合成的（22R）-腺苷胆碱的谱图相同，表明HpnH催化双萜的C29和5'-脱氧腺苷的C5'之间的立体选择性CC形成。此外，在含D 2 O的缓冲液中的HpnH反应表明，在腺苷胆碱的C 22位上掺入了D原子。根据这些结果，
• Triterpenoids from ten Lithocarpus species of Hong Kong
  作者：Wai Haan Hui、Phyllis D.S. Ko、Yuk-Chun Lee、Man-Moon Li、Henry R. Arthur

  DOI：10.1016/0031-9422(75)85187-9

  日期：1975.4

  Abstract From the petrol extracts of the leaves and stems of ten Lithocarpus species ( L. attenuata , L. cornea , L. elizabethae , L. glabra , L. haipinii , L. hancei , L. harlandi , L. irwinii , L. litchioides , and L. polystachya ) of the Fagaceae family, were isolated 23 different triterpenoids, and sitosterol and stigmasterol. Of the triterpenoids, 11 belonged to the oleanane and rearranged oleanane

  摘要 来自十种石果属植物（ L. attenuata 、 L.cornea 、 L. elizabethae 、 L. glabra 、 L. haipinii 、 L. hancei 、 L. harlandi 、 L. irwinii 、 L. litchioides ）的叶和茎的石油提取物, 和 L. polystachya ), 分离出 23 种不同的三萜、谷甾醇和豆甾醇。在三萜类化合物中，有 11 种属于齐墩果烷和重排齐墩果烷组 [β-香树脂醇、弗里德林、弗里德兰-3β-醇、谷蛋白醇、蒲公英、蒲公英及其醋酸盐、树油酚​​ (28-羟基弗里德兰-3-one)、弗里德兰-2、 3-dione (3-hydroxyfriedel-3-en-2-one)、pachysandiol-A (2α,3β-dihydroxyfriedelane) 和新化合物石果酸内酯 C 30 H 50 O 2
• Method for inhibiting cancer cells and treating diseases comprising administering a formula composition of antrodia cinnamomea
  申请人：Cheng-Lin Agricultural Biotechnology Co., Ltd.

  公开号：US10167446B2

  公开（公告）日：2019-01-01

  A method for cultivating antrodia cinnamomea includes transplanting bacterial strains of antrodia cinnamomea into a petri dish receiving culture ingredients. The bacterial strains of antrodia cinnamomea are transferred into a culture container after mycelia of the bacterial strains of antrodia cinnamomea have grown to a predetermined area. The culture container receives a culture fluid. A formula composition of a culture medium for cultivating antrodia cinnamomea is added into the culture container after the mycelia of the bacterial strains of antrodia cinnamomea have grown in the culture container. The formula composition of the culture medium for cultivating antrodia cinnamomea includes growth basal ingredients and cultivating basal ingredients. The growth basal ingredients includes hydroxyhopanone. Mycelia of antrodia cinnamomea metabolize hydroxyhopanone precursors of agarwood during a growth procedure of the mycelia of antrodia cinnamomea, such that the mycelia of antrodia cinnamomea have a higher percentage of triterpenoids after fermentation.

  一种培养肉桂蝙蝠蛾的方法包括将肉桂蝙蝠蛾的细菌菌株移植到接受培养成分的培养皿中。在肉桂蝙蝠蛾菌株的菌丝生长到预定面积后，将菌株移入培养容器中。培养容器接收培养液。在肉桂蝙蝠蛾菌株的菌丝在培养容器中生长后，将用于培养肉桂蝙蝠蛾的培养基的配方组合物加入培养容器中。栽培肉桂茸蚂蚁的培养基的配方成分包括生长基础成分和栽培基础成分。生长基础成分包括羟基茄酮。在蚂蚁肉桂菌丝体的生长过程中，蚂蚁肉桂菌丝体会代谢琼脂木的羟基茄酮前体，从而使蚂蚁肉桂菌丝体在发酵后具有较高比例的三萜类化合物。