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An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach To Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2019-07-05 , DOI: 10.1021/acs.jnatprod.9b00415
Lin Du 1 , Charissa Munteanu 2 , Jarrod B King 1 , Doug E Frantz 2 , Robert H Cichewicz 1
Affiliation  

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 SN2'-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.

中文翻译:

亲电子天然产物提供了一种安全,强大的除臭方法,以抵消臭鼬喷雾中遇到的恶臭有机硫代谢物。

臭鼬的肛门分泌物包括几种类型的恶臭有机硫化合物。臭鼬在防御性地使用刺激性代谢物,以抵制捕食者构成的威胁,在世界许多地方,这些可感知的威胁包括人类及其宠物。用于检测有机硫代谢物的极低阈值使得“脱臭”人,动物和衣物的过程充满了许多挑战。真菌衍生的代谢产物percosine A(4)是一种混杂但稳定的亲电子化合物,我们提出将其用作某些真菌的化学防御新形式。我们的研究表明,percosine A容易与臭味喷射的分泌物发生反应,从而将它们转变为无味的产品。机理和计算研究表明,在水性条件下,percosine A及其合成类似物通过SN2'型机理与硫醇和硫代乙酸酯反应生成稳定的硫醚。测试表明,percosine A不会引起皮肤或眼睛刺激,当配制包含辅助化妆品成分时,在消除臭鼬肛门腺分泌物方面非常有效。
更新日期:2019-07-05
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