(+)-萜烯七脂酸 | 57710-57-3

• 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
• 中文名称: (+)-萜烯七脂酸
• 英文名称: koningic acid
• 英文别名: heptelidic acid；(5aS,6R,9S,9aS)-1-oxo-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid
• CAS: 57710-57-3
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: JESMSCGUTIEROV-RTWAVKEYSA-N

物化性质

• 沸点：
  501.1±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL； DMSO：30mg/mL；乙醇：30mg/mL
• LogP：
  2.034 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-萜烯七脂酸 在 溶剂黄146 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以88%的产率得到Heptelidic acid chlorohydrin
  参考文献：
  名称：

  Anticancer activity of koningic acid and semisynthetic derivatives

  摘要：

  A screening program aimed at discovering novel anticancer agents based on natural products led to the selection of koningic acid (KA), known as a potent inhibitor of glycolysis. A method was set up to produce this fungal sesquiterpene lactone in large quantities by fermentation, thus allowing (i) an extensive analysis of its anticancer potential in vitro and in vivo and (ii) the semi-synthesis of analogues to delineate structure-activity relationships. KA was characterized as a potent, but non-selective cytotoxic agent, active under both normoxic and hypoxic conditions and inactive in the A549 lung cancer xenograft model. According to our SAR, the acidic group could be replaced to keep bioactivity but an intact epoxide is essential. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.004
• 作为产物：
  描述：

  methyl (5R,6S)-6-[3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]prop-1-enyl]-5-propan-2-yl-2-(trimethylsilylmethyl)cyclohexene-1-carboxylate 在 chromium(VI) oxide 、 叔丁基过氧化氢 、 sodium hydroxide 、 sodium chlorite 、 bis(2-oxo-1,3-oxazolidin-3-yl)phosphinous chloride 、 hexacarbonyl molybdenum 、 三氯化铁 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.12h， 生成 (+)-萜烯七脂酸
  参考文献：
  名称：

  EPC synthesis of (+)-heptelidic acid

  摘要：

  An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate 4 to the auxiliary shielded enoate 5n which gives the adduct 7n as a single diastereomer. After cleavage of the acetal protecting group and of the chiral auxiliary the enantiomerically pure beta-ketoester 12 has been obtained which has been transformed to the title compound 1 (11 steps starting from 5n, 10.6% overall yield).

  DOI：

  10.1007/bf00807894

文献信息

• Biosynthesis of the fungal glyceraldehyde-3-phosphate dehydrogenase inhibitor heptelidic acid and mechanism of self-resistance
  作者：Yan Yan、Xin Zang、Cooper S. Jamieson、Hsiao-Ching Lin、K. N. Houk、Jiahai Zhou、Yi Tang

  DOI：10.1039/d0sc03805a

  日期：——

  nature evolves resistance to highly potent natural products, we examined the biosynthesis and mechanism of self-resistance of the fungal glyceraldehyde-3-phosphate dehydrogenase (GAPDH) inhibitor heptelidic acid (HA). HA is a nanomolar inhibitor of GADPH through the covalent modification of the active site cysteine thiol. The biosynthetic pathway of HA was elucidated, which uncovered the enzymatic basis

  克服对生物活性小分子的耐药性是医疗保健和农业面临的重大挑战。因此，发现耐药机制的努力对于开发新的抗生素、抗癌药物和杀虫剂至关重要。为了研究自然界如何进化出对高效天然产物的抗性，我们研究了真菌 3-磷酸甘油醛脱氢酶 (GAPDH) 抑制剂庚酸 (HA) 的生物合成和自抗机制。HA 是一种纳摩尔 GADPH 抑制剂，通过活性位点半胱氨酸硫醇的共价修饰。阐明了HA的生物合成途径，揭示了环氧化物弹头形成的酶学基础。使用生物合成中间体的构效关系研究确定了稠合内酯环系统在 HA 中的重要性。Hs -GAPDH 与 HA 共价结合。HA 簇中编码的 GAPDH 同工酶 HepG 对 HA 不太敏感，因此有助于生产宿主的自我抗性。人类 GAPDH 和 HepG 晶体结构的比较表明，活性位点内部和远处的突变都有助于抗失活，这通过诱变得到证实。由于 GAPDH 在有氧糖酵解和其他细胞功能中起着关键作用，了解 HA
• Product
  申请人：ALPHA BIOPESTICIDES LIMITED

  公开号：US11019825B2

  公开（公告）日：2021-06-01

  The invention provides an agrochemical composition comprising: (a) one or more fatty acids or derivatives thereof; and (b) a strain, culture, culture filtrate, spores or mycelia of a species of a fungus or oomycete, or a metabolite produced by a species of a fungus or oomycete, which strain, culture, culture filtrate, spores, mycelia or metabolite directly or indirectly (i) inhibits the growth or reproduction of plant pathogens or (ii) kills plant pathogens. Also provided is a method for controlling fungi or oomycetes at a locus, a method for promoting growth in a plant and a method for controlling nematodes at a locus.

  本发明提供了一种农用化学品组合物，该组合物包含：(a) 一种或多种脂肪酸或其衍生物；(b) 某种真菌或卵菌的菌株、培养物、培养物滤液、孢子或菌丝体，或由某种真菌或卵菌产生的代谢物，该菌株、培养物、培养物滤液、孢子、菌丝体或代谢物直接或间接地(i) 抑制植物病原体的生长或繁殖，或(ii) 杀死植物病原体。还提供了一种在基因座上控制真菌或卵菌的方法、一种促进植物生长的方法和一种在基因座上控制线虫的方法。
• Riehs; Ecker; Urban, Scientia Pharmaceutica, 1998, vol. 66, # 3, p. 199 - 204
  作者：Riehs、Ecker、Urban

  DOI：——

  日期：——
• NEW PRODUCT
  申请人：ALPHA BIOPESTICIDES LIMITED

  公开号：US20180146683A1

  公开（公告）日：2018-05-31

  The invention provides an agrochemical composition comprising: (a) one or more fatty acids or derivatives thereof; and (b) a strain, culture, culture filtrate, spores or mycelia of a species of a fungus or oomycete, or a metabolite produced by a species of a fungus or oomycete, which strain, culture, culture filtrate, spores, mycelia or metabolite directly or indirectly (i) inhibits the growth or reproduction of plant pathogens or (ii) kills plant pathogens. Also provided is a method for controlling fungi or oomycetes at a locus, a method for promoting growth in a plant and a method for controlling nematodes at a locus.
• EPC synthesis of (+)-heptelidic acid
  作者：G. Riehs、E. Urban

  DOI：10.1007/bf00807894

  日期：1997.3

  An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate 4 to the auxiliary shielded enoate 5n which gives the adduct 7n as a single diastereomer. After cleavage of the acetal protecting group and of the chiral auxiliary the enantiomerically pure beta-ketoester 12 has been obtained which has been transformed to the title compound 1 (11 steps starting from 5n, 10.6% overall yield).