(+)-pericosine A | 200335-68-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-pericosine A
• 英文别名: Pericosine A；methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxycyclohexene-1-carboxylate
• CAS: 200335-68-8
• 化学式: C₈H₁₁ClO₅
• 分子量: 222.625
• InChiKey: AEDMWQPFIPNFCS-ZTYPAOSTSA-N

物化性质

• 沸点：
  367.0±42.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)
• 溶解度：
  二氯甲烷：可溶，DMSO：可溶，乙醇：可溶，甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-pericosine A 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (1R,2R,3R,6R)-5-(methoxycarbonyl)-6-(phenethylthio)cyclohex-4-ene-1,2,3-triyl triacetate
  参考文献：
  名称：

  An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach To Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray

  摘要：

  The anal secretions of skunks comprise several types of malodorous organosulfur compounds. The pungent metabolites are used defensively by skunks to repel threats posed by predators, and in many parts of the world, those perceived threats include humans and their pets. The extremely low thresholds for detection of the organosulfur metabolites make efforts to "de-skunk" people, animals, and clothing a process fraught with many challenges. The fungal-derived metabolite pericosine A (4) is a promiscuous yet stabile electrophilic compound that we propose is used by some fungi as a novel form of chemical defense. Our investigations have indicated that pericosine A readily reacts with skunk-spray secretions to transform them into odorless products. Mechanistic and computational studies suggested that pericosine A and its synthetic analogues react via S_N2'-type mechanisms with thiols and thioacetates under aqueous conditions to generate stable thioethers. Testing revealed that pericosine A did not cause skin or eye irritation and was highly effective at deodorizing skunk anal gland secretions when formulated to include adjunctive cosmetic ingredients.

  DOI：

  10.1021/acs.jnatprod.9b00415
• 作为产物：
  描述：

  methyl (3R,4R,5S,6R)-6-O-acetyl-4,5-O-cyclohexylidene-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carboxylate 在 咪唑 、 氯化亚砜 、 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (+)-pericosine A
  参考文献：
  名称：

  抗肿瘤天然产物（+）-和（-）-Pericosine A的第一个全合成：绝对立体结构的测定†

  摘要：

  已完成（+）-和（-）-pericosine A的第一个全合成，从而能够修订和确定该抗肿瘤天然产物的绝对构型，即甲基（3 S，4 S，5 S，6 S）- 6-氯-3,4,5-三羟基-1-环己烯-1-羧酸酯。该全合成的每一步都以优异的立体选择性进行得很好。关键步骤中的中间体结构通过详细的2D NMR分析得到确认。

  DOI：

  10.1021/jo070715l

文献信息

• Facile and Efficient Synthesis of Naturally Occurring Carbasugars (+)-Pericosines A and C
  作者：Yoshihide Usami、Marie Ohsugi、Koji Mizuki、Hayato Ichikawa、Masao Arimoto

  DOI：10.1021/ol9008188

  日期：2009.6.18

  efficient synthesis of antitumor marine natural product (+)-pericosine A was achieved from (−)-quinic acid in 11.7% overall yield, which is 20 times better than our previously reported synthesis. The crucial steps of this synthesis include the regio- and stereoselective bromohydrination of an unstable diene and the ring opening of an epoxide. This synthetic route was applicable to a synthesis of (+)-pericosine

  从（-）-奎宁酸可高效合成抗肿瘤海洋天然产物（+）-pericosine A，总产率为11.7％，比我们先前报道的合成方法高20倍。该合成的关键步骤包括不稳定的二烯的区域和立体选择性溴化水合和环氧化物的开环。该合成路线适用于（+）-pericosine C的合成，也适用于（-）-pericosine C的合成。
• [EN] SHIKIMATE ANALOGUES AND METHODS OF USE<br/>[FR] ANALOGUES DE SHIKIMATE ET MÉTHODES D'UTILISATION
  申请人：UNIV OKLAHOMA

  公开号：WO2017142866A1

  公开（公告）日：2017-08-24

  The present disclosure, in at least certain embodiments, is directed to shikimate (shikimic acid) analogues and compositions thereof, kits which contain the shikimate analogues or compositions thereof, and methods of use of the compounds and compositions for treating epithelial surfaces before or following exposure to irritants, allergens, and toxic agents (for example, urushiol).

  本公开至少在某些实施例中涉及植酸（香草酸）类似物及其组成物，包含植酸类似物或其组成物的工具包，以及用于处理上皮表面在暴露于刺激物、过敏原和毒性剂（例如漆油）之前或之后的化合物和组成物的使用方法。
• Pericosines, antitumour metabolites from the sea hare-derived fungus Periconia byssoides. Structures and biological activities
  作者：Takeshi Yamada、Masashi Iritani、Hirohumi Ohishi、Kayo Tanaka、Katsuhiko Minoura、Mitsunobu Doi、Atsushi Numata

  DOI：10.1039/b713060k

  日期：——

  of spectroscopic analyses, including 1D and 2D NMR techniques, and X-ray analysis. In addition, conformation for all the compounds has been discussed. Compounds 1-3 exhibited significant growth inhibition against tumour cell lines. Pericosine A 1 also showed significant in vivo tumour inhibitory activity. In addition, compound inhibited the protein kinase EGFR and topoisomerase II.

  已经从最初从海兔Aplysia kurodai分离的Periconia byssoides菌株中分离出Pericosines AE 1-5。在它们之中，周二肌氨酸C 3和E 5被分离为对映异构体混合物。除化合物1外，它们的立体结构已根据光谱分析（包括1D和2D NMR技术以及X射线分析）进行了阐明或鉴定。另外，已经讨论了所有化合物的构象。化合物1-3显示出对肿瘤细胞系的显着生长抑制。Pericosine A 1还显示出显着的体内肿瘤抑制活性。另外，化合物抑制蛋白激酶EGFR和拓扑异构酶II。
• Facile carbohydrate-based stereocontrolled divergent synthesis of (+)-pericosines A and B
  作者：Subhankar Tripathi、Ajam Chand Shaikh、Chinpiao Chen

  DOI：10.1039/c1ob06383a

  日期：——

  An isomer-divergent synthesis of naturally occurring pericosines A and B is described starting from a known D-ribose derived ene-diol in 35% and 41% overall yields respectively of which the latter is the best synthetic method reported for pericosine B. The key features of this synthesis include the stereoselective NHK vinylation of the terminal aldehyde to the versatile diolefinic chiral intermediate and elegant conversions of the same to the corresponding final products via RCM (Ring Closing Metathesis).

  该合成方法的主要特点包括通过 NHK 乙烯基化将末端醛转化为多用途二烯烃手性中间体，并通过 RCM（闭环合成）将二烯烃手性中间体优雅地转化为相应的最终产物。
• Enantiomeric composition of natural pericosine A derived from <i>Periconia byssoides</i> and α‐glycosidase inhibitory activity of (−)‐enantiomer
  作者：Yoshihide Usami、Kimika Nakamura、Yoshino Mizobuchi、Koji Mizuki、Shinya Harusawa、Hiroki Yoneyama、Takeshi Yamada

  DOI：10.1002/chir.23491

  日期：2022.10

  chromatography (HPLC) analysis of natural pericosine A, which appeared in literature first in 1977, from Periconia byssoides was conducted using a column CHIRALPAK® AD-H to determine the enantiomeric composition of the original mixture which was found to be 68: 32 mixtures of (+)- and (−)-enantiomer, respectively. Furthermore, two independently isolated samples of pericosine A from the same fungus were also

  使用柱 CHIRALPAK® AD-H 对 1977 年首次出现在文献中的来自Periconia byssoides的天然 pericosine A 进行手性高效液相色谱 (HPLC) 分析，以确定原始混合物的对映体组成，该混合物被发现是68：分别为(+)-和(-)-对映异构体的32种混合物。此外，还分析了来自同一真菌的两个独立分离的 pericosine A 样品，以在 HPLC 图表中以大约 1:1 的比例显示两个峰。这些结果得出结论，源自 Periconia byssoides 的 pericosine A确实是一种对映体混合物。合成的对映异构体对三种肿瘤细胞（p388、L1210、HL-60）的抗肿瘤活性进行了评估，表明对所有三种肿瘤细胞系都有中等的细胞毒性，但未观察到对映异构体之间的效力差异显着。相比之下，当针对五种糖苷酶s抑制活性（α-和 β-葡萄糖苷酶、α-和 β-半乳糖苷酶以及