16α,17-dihydroxykauran-19-oic acid | 3301-61-9

• 物质功能分类: 天然产物 - 萜类
• 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: 16α,17-dihydroxykauran-19-oic acid
• 英文别名: 16α,17-dihydroxy-ent-kauran-19-oic acid；16α,17-dihydroxy-ent-kaurane-19-oic acid；ent-16β,17-dihydroxy-kauran-19-oic acid；Diterpenoid SP-II；(1S,4S,5R,9S,10R,13R,14R)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 3301-61-9
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: MRBLTWPEPGRXQN-INIPNLRTSA-N

物化性质

• 熔点：
  260-262 °C
• 沸点：
  505.6±35.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)
• 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)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  16α,17-dihydroxykauran-19-oic acid 在 lithium aluminium tetrahydride 作用下， 生成 ent-16β,17,19-kaurenetriol
  参考文献：
  名称：

  Jefferies,P.R.; Payne,T.G., Australian Journal of Chemistry, 1965, vol. 18, p. 1441 - 1450

  摘要：

  DOI：
• 作为产物：
  描述：

  grandiflorenic acid 在 platinum(IV) oxide 氢气 作用下， 生成 16α,17-dihydroxykauran-19-oic acid
  参考文献：
  名称：

  Obermann,H.; Spiteller,G., Chemische Berichte, 1975, vol. 108, p. 1093 - 1100

  摘要：

  DOI：

文献信息

• Oxyfunctionalization Products of Terpenoids with Dimethyldioxirane and Their Biological Activity
  作者：Shoujiro Ogawa、Keiji Hosoi、Noriaki Ikeda、Mitsuko Makino、Yasuo Fujimoto、Takashi Iida

  DOI：10.1248/cpb.55.247

  日期：——

  Oxyfunctionalization of the bioactive terpenoids, ursolic acid acetate (1), oleanolic acid acetate (5), lupeol acetate (12), and kaurenic acid (17), with dimethyldioxirane (DMDO) was investigated. Treatment of the terpenoids with DMDO under mild conditions afforded a variety of oxidation and oxydegradation products to yield naturally occurring and/or novel compounds in one step. After chromatographic separation, the structures of the individual isolated products were determined using spectroscopic methods including several homonuclear (1H–1H) and heteronuclear (1H–13C) shift-correlated 2D-NMR techniques. The inhibitory activity of the terpenoid derivatives against α-glucosidase was investigated and compounds 1, 3, 7, and 9 were found to exhibit potent activity.

  研究人员用二甲基二氧环己烷（DMDO）对具有生物活性的萜类化合物熊果酸乙酸酯（1）、齐墩果酸乙酸酯（5）、羽扇豆醇乙酸酯（12）和高瑞香酸（17）进行了氧化官能化处理。在温和的条件下，用二甲基二氧环己烷处理萜类化合物，可产生多种氧化和氧降解产物，从而一步生成天然和/或新型化合物。色谱分离后，利用光谱方法（包括几种同核（1H-1H）和异核（1H-13C）位移相关的二维核磁共振技术）确定了各个分离产物的结构。研究了萜类衍生物对 α-葡萄糖苷酶的抑制活性，发现化合物 1、3、7 和 9 具有很强的活性。
• A straightforward synthesis of natural oxygenated <i>ent</i>-kaurenoic acid derivatives
  作者：Olga Morarescu、Marina Grinco、Veaceslav Kulciţki、Alic Barba、Olga Garbuz、Valentin Gudumac、Aurelian Gulea、Nicon Ungur

  DOI：10.1080/00397911.2020.1821225

  日期：2021.1.2

  The paper presents the synthesis of some natural diterpenoids of ent-kauranic structure, starting from ent-kaur-16-en-19-oic acid, a natural diterpenoid readily available from the dried wastes of s...

  本文介绍了从 ent-kaur-16-en-19-oic 酸开始合成一些具有 ent-kauranic 结构的天然二萜，这是一种易于从 s 的干燥废物中获得的天然二萜。
• A new <i>ent</i>-kaurane diterpene derivative from the stems of <i>Eurya chinensis</i> R.Br
  作者：Jia-Ling Song、Yao Yuan、Ling-Hui Nie、Bai-Lin Li、Xu-Bing Qin、Yan Li、Jie-Wei Wu、Sheng-Xiang Qiu

  DOI：10.1080/14786419.2017.1343327

  日期：2018.1.17

  Br. The structure of the new compound was established by extensive analysis of mass spectrometric and 1D and 2D NMR spectroscopic data. Compound 1 showed moderate anti-inflammatory activities with IC50 value of 8.12 μM. This is the first example of diterpenoids with 4-hydroxy-4-(2-hydroxyethyl)-1-hydroxyl-cyclohexanoyl substituent.

  一个新的ENT -kaurane双萜衍生物（1）中，用四个已知二萜沿，分离从所述茎拎羊草R.Br. 新化合物的结构是通过对质谱以及1D和2D NMR光谱数据进行广泛分析而建立的。化合物1显示出中等的抗炎活性，IC 50值为8.12μM。这是具有4-羟基-4-（2-羟基乙基）-1-羟基-环己酰基取代基的二萜的第一个实例。
• A New ent-Kaurane Diterpenoid Glycoside from the Leaves of Cussonia bojeri, a Malagasy Endemic Plant.
  作者：Liva Harinantenaina、Ryoji Kasai、Kazuo Yamasaki

  DOI：10.1248/cpb.50.1122

  日期：——

  A new ent-kaurane diterpene glycoside, β-D-glucopyranosyl 17-hydroxy-ent-kauran-19-oate-16-O-β-D-glucopyranoside (4) was isolated from the dried leaves of Cussonia bojeri SEEM., together with four known compounds identified as 16β,17-dihydroxy-kauran-19-oic acid (1), β-D-glucopyranosyl 16β,17-dihydroxy-(−)-kauran-19-oate (2), paniculoside IV (3), and rutin (5). The structure of 4 was deduced on the basis of chemical and spectroscopic evidence.

  从Cussonia bojeri SEEM的干燥叶片中分离出一种新的ent-kaurane二萜糖苷，β-D-吡喃葡萄糖基17-羟基-ent-贝壳杉-19-酸-16-O-β-D-吡喃葡萄糖苷（4），以及四种已知的化合物，分别为16β,17-二羟基-贝壳杉-19-酸（1）、β-D-吡喃葡萄糖基16β,17-二羟基-(−)-贝壳杉-19-酸酯（2）、paniculoside IV（3）和芦丁（5）。4的结构是根据化学和光谱证据推断的。
• The microbiological transformation of two ent-16β,17-epoxykaurane derivatives by Gibberella fujikuroi
  作者：Braulio M. Fraga、Pedro González、Ricardo Guillermo、James R. Hanson、Melchor G. Hernández、Jacqueline A. Takahashi

  DOI：10.1016/s0031-9422(00)90345-5

  日期：1994.11

  The biotransformation of ent-16 beta,17-epoxy-7 alpha-hydroxykaurane by Gibberella fujikuroi affords ent-7 alpha,11 alpha,16 beta,17-tetrahydroxykaurane and ent-7 alpha,9 alpha,16 beta,17-tetrahydroxykaurane. These results indicated that the presence of the 16 alpha,17-diol group, into which the 16 alpha,17-epoxy is transformed in the medium, inhibits oxidation at C-19 and favours hydroxylation at C-11(beta). Incubation of ent-16 beta,17-epoxykauran-19-oic acid, via the 16 alpha,17-diol, gave the 7-aldehyde of 16 alpha,17-dihydroxy-GA(12).