bryonolol | 39765-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bryonolol
• 英文别名: (3S,4aR,6aS,6bS,8aS,11R,12aR,14bS)-11-(hydroxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,13,14-tetradecahydropicen-3-ol
• CAS: 39765-50-9
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: ZTFHGNGMNAIRAI-QWNCWLTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  乙酸酐 、 bryonolol 在 吡啶 作用下， 生成 bryonolol diacetate
  参考文献：
  名称：

  7-Oxodihydrokarounidiol (7-Oxo-D:C-friedo-olean-8-ene-3.ALPHA.,29-diol), a Novel Triterpene from Trichosanthes kirilowii.

  摘要：

  从葫芦科植物 Trichosanthes kirilowii 的种子中分离出的 7-oxodihydrokarounidiol [7-oxo-D : C-friedo-olean-8-ene-3α, 29-diol] 与来自同一来源的 karounidiol [D : C-friedo-oleana-7, 9(11)-diene-3α, 29-diol] 通过化学关联确定了结构。另外两种天然产物，即香叶醇酸（3β-羟基-D : C 炸过油桐-8-烯-29-酸）和香叶酮酸（3-氧代-D : C 炸过油桐-8-烯-29-酸）也与卡鲁尼二醇相关。

  DOI：

  10.1248/cpb.40.1199
• 作为产物：
  描述：

  (2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 bryonolol
  参考文献：
  名称：

  Sandoricum indicum 中的三萜类化合物和其他成分

  摘要：

  摘要 在白参果实中鉴定出苔藓酸和苔藓酸、内肌醇和粘酸。

  DOI：

  10.1016/s0031-9422(00)86404-3

文献信息

• Triterpenoid and other constituents from Sandoricum indicum
  作者：K.Y. Sim、H.T. Lee

  DOI：10.1016/s0031-9422(00)86404-3

  日期：1972.11

  Abstract Bryononic and bryonolic acids, mesoinositol and mucic acid were identified in the fruits of Sandoricum indicum .

  摘要 在白参果实中鉴定出苔藓酸和苔藓酸、内肌醇和粘酸。
• Conformations of bryonolic acid and its derivatives in CDCl3 solution by1H and13C NMR spectroscopy
  作者：Wasuke Kamisako、Kiyoko Suwa、Chie Honda、Koichiro Isoi、Hiroshi Nakai、Motoo Shiro、Katsunosuke Machida

  DOI：10.1002/mrc.1260251004

  日期：1987.10

  Comparison of the 1H and 13C chemical shift data of bryonolic acid (D : C‐friedoolean‐8‐en‐3β‐ol‐29‐oic acid) and its derivatives (13 species) revealed that the conformational features of these compounds in CDCl3 solution depend on whether the functional groups at C‐29 are trigonal, such as COOCH3, or tetrahedral, such as CH2OH. In order to study the conformational features of these two groups of compounds

  溴酚酸（D：C-friedoolean-8-en-3β-ol-29-oic酸）及其衍生物（13种）的1H和13C化学位移数据的比较揭示了这些化合物在CDCl3溶液中的构象特征取决于 C-29 处的官能团是三方的，如 COOCH3，还是四面体的，如 CH2OH。为了研究这两组化合物的构象特征，D : C-friedoolean-8-en-29-oic acid, D : C-friedoolean-的甲酯的 E 环上的质子之间的邻位耦合常数测量了 8-en-29-oic 及其醋酸盐。结果与 S 型（D-E 环：船-船型）和 F 型（D-E 环：
• Five D: C-Friedo-Oleanane Triterpenes from the Seeds of Trichosanthes kirilowii MAXIM. and Their Anti-inflammatory Effects.
  作者：Toshihiro AKIHISA、Ken YASUKAWA、Yumiko KIMURA、Michio TAKIDO、Wilhelmus C. M. C. KOKKE、Toshitake TAMURA

  DOI：10.1248/cpb.42.1101

  日期：——

  Five triterpenes with a D : C-friedo-oleanane skeleton, D : C-friedo-oleana-7, 9(11)-diene-3β, 29-diol (3-epikarounidiol), 7-oxo-D : C-friedo-olean-8-en-3β-ol (7-oxoisomultiflorenol), 7-oxo-8β-D : C-friedo-olean-9(11)-ene-3α, 29-diol, D : C-friedo-olean-8-ene-3α, 29-diol (3-epibryonolol), and D : C-friedo-olean-8-ene-3β, 29-diol (bryonolol), the first four of which are new naturally occurring compounds, were isolated from the seeds of Trichosanthes kirilowii MAXIM. The structures were determined by spectral and chemical methods. 3-Epikarounidiol, 7-oxoisomultiflorenol, and 3-epibryonolol showed marked inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear inflammation in mice. The 50% inhibitory dose of these triterpenes for TPA-induced inflammation (1 μg) was 0.2-0.6 mg/ear.

  从Trichosanthes kirilowii MAXIM的种子中分离出五种具有D：C-friedo-oleanane骨架的三萜类化合物，即D：C-friedo-oleana-7,9(11)-diene-3β,29-diol（3-epikarounidiol）、7-oxo-D：C-friedo-olean-8-en-3β-ol（7-oxoisomultiflorenol）、7-oxo-8β-D：C-friedo-olean-9(11)-ene-3α,29-diol、D：C-friedo-olean-8-ene-3α,29-diol（3-epibryonolol）和D：C-friedo-olean-8-ene-3β,29-diol（bryonolol），其中前四种是新发现的天然化合物。通过光谱和化学方法确定了这些化合物的结构。3-Epikarounidiol、7-oxoisomultiflorenol和3-epibryonolol对小鼠12-O-tetradecanoylphorbol-13-acetate（TPA）诱导的耳部炎症具有显著的抑制活性。这些三萜类化合物对TPA诱导的炎症的5
• 7-Oxodihydrokarounidiol (7-Oxo-D:C-friedo-olean-8-ene-3.ALPHA.,29-diol), a Novel Triterpene from Trichosanthes kirilowii.
  作者：Toshihiro AKIHISA、Wilhelmus C. M. C. KOKKE、Toshitake TAMURA、Toshio NAMBARA

  DOI：10.1248/cpb.40.1199

  日期：——

  The structure of 7-oxodihydrokarounidiol [7-oxo-D : C-friedo-olean-8-ene-3α, 29-diol], isolated from the seeds of Trichosanthes kirilowii (Cucurbitaceae), was determined by chemical correlation with karounidiol [D : C-friedo-oleana-7, 9(11)-diene-3α, 29-diol] from the same source. Two other natural products, viz. bryonolic acid (3β-hydroxy-D : C-friedo-olean-8-en-29-oic acid) and bryononic acid (3-oxo-D : C-friedo-olean-8-en-29-oic acid), were also correlated with karounidiol.

  从葫芦科植物 Trichosanthes kirilowii 的种子中分离出的 7-oxodihydrokarounidiol [7-oxo-D : C-friedo-olean-8-ene-3α, 29-diol] 与来自同一来源的 karounidiol [D : C-friedo-oleana-7, 9(11)-diene-3α, 29-diol] 通过化学关联确定了结构。另外两种天然产物，即香叶醇酸（3β-羟基-D : C 炸过油桐-8-烯-29-酸）和香叶酮酸（3-氧代-D : C 炸过油桐-8-烯-29-酸）也与卡鲁尼二醇相关。
• Biosynthesis of bryonolic acid in cultured cells of watermelon
  作者：Hi Jae Cho、Michiho Ito、Shigeo Tanaka、Wasuke Kamisako、Mamoru Tabata

  DOI：10.1016/0031-9422(93)85100-6

  日期：1993.8

  Bryonolic acid, a pentacyclic triterpene having an anti-allergic activity, was biosynthesized from R-[2-14C]mevalonate or [2-14C]acetate administered to cell cultures of watermelon (Citrullus lanatus). The radioactivity of the labelled mevalonate added to cell-free extracts in the presence of ATP, Mg2+ and NADPH was also incorporated into bryonolic acid as well as into the possible intermediates, isomultiflorenol

  Bryonolic acid 是一种具有抗过敏活性的五环三萜，由 R-[2-14C] 甲羟戊酸或 [2-14C] 乙酸盐生物合成，施用于西瓜 (Citrullus lanatus) 细胞培养物。在存在 ATP、Mg2+ 和 NADPH 的情况下，添加到无细胞提取物中的标记甲羟戊酸的放射性也被并入了bryonolic acid 以及可能的中间体，isomultiflorenol、bryonolol 和bryonolal。此外，将 [14C]2,3-氧化角鲨烯添加到相同无细胞提取物的微粒体溶液中，通过酶促转化为异山竹醇，这被认为是苔藓酸生物合成中的第一个环化产物。这些结果表明，bryonolic acid 是由 2,3-氧化角鲨烯通过异多花烯醇生物合成的，随后在 C-29 处氧化甲基。