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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
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posted on 2019-07-03, 20:14 authored by Lin Du, Charissa Munteanu, Jarrod B. King, Doug E. Frantz, Robert H. CichewiczThe 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.
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malodorous organosulfur compoundsdeodorizing skunk anal gland secretionsstabile electrophilic compoundRobust Odor Neutralization Approachskunk-spray secretionsanal secretionscause skinSkunk Sprayorganosulfur metabolitesthreatchemical defensetypeeye irritationnovel formElectrophilic Natural Product Providesfungal-derived metabolite pericosineodorless productsCounteract Malodorous Organosulfur Metabolites Encountered
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