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Essential oils from Bolivia. XV. herzogole, an original monoterpene benzodioxole from an essential oil from Pentacalia herzogii (Cabrera) Cuatrec

St-Gelais Alexis, Maldonado Eliana M., Saavedra Gloria, Siles-Alvarado Samuel, Alsarraf Jérôme, Collin Guy et Pichette André. (2021). Essential oils from Bolivia. XV. herzogole, an original monoterpene benzodioxole from an essential oil from Pentacalia herzogii (Cabrera) Cuatrec. Molecules, 26, (19), e5766.

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Over 15 years, with the support of a Canadian funding agency, the Universidad Mayor de San Simón, in Bolivia, undertook a large survey of aromatic plants of the South American country. More than a hundred species were studied under various aspects, including the production and characterization of essential oils. As part of this survey, the chemical composition of an essential oil sample obtained from Pentacalia herzogii (Asteraceae) growing wild in the High Valley region of the department of Cochabamba was determined by a combination of GC and GC-MS measurements. α-Pinene was the main constituent of this essential oil (34%), accompanied by limonene (22%) and germacrene D (7.5%) as well as an important fraction of methoxylated monoterpenoids. They were mainly isomers of thymol methyl ether, accounting for 13% of the chromatogram. A new quantitatively important compound (9%) was identified through NMR and chemical synthesis as 4-isopropyl-6-methylbenzo[d][1,3]dioxole, and designated herzogole, alongside the minor related compound 1-isopropyl-2,3-dimethoxy-5-methylbenzene. The monoterpene benzodioxole featured a distinctive green-phenolic aroma which could raise interest for fragrance use. Since these compounds were not known naturally, a biosynthetic mechanism of their formation was proposed and put in perspective to illustrate the metabolic originality of P. herzogii.

Type de document:Article publié dans une revue avec comité d'évaluation
Version évaluée par les pairs:Oui
Identifiant unique:10.3390/molecules26195766
Sujets:Sciences naturelles et génie > Sciences naturelles > Biologie et autres sciences connexes
Département, module, service et unité de recherche:Unités de recherche > Centre de recherche sur la Boréalie (CREB)
Départements et modules > Département des sciences fondamentales
Mots-clés:Pentacalia herzogii, Senecio sp., essential oil composition, isothymol methyl ether, thymol methyl ether, α-pinene, herzogole, nuclear magnetic resonance (NMR)
Déposé le:04 juill. 2023 15:36
Dernière modification:04 juill. 2023 15:36
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