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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; Pichette, André.
Afiliação
  • St-Gelais A; Laboratoire Phytochemia, 628, Boulevard du Saguenay Ouest, Saguenay, QC G7J 1H4, Canada.
  • Maldonado EM; Centro de Tecnología Agroindustrial, Universidad Mayor de San Simón, Cochabamba 992, Bolivia.
  • Saavedra G; Centro de Tecnología Agroindustrial, Universidad Mayor de San Simón, Cochabamba 992, Bolivia.
  • Siles-Alvarado S; Centro Especializado de Instrumentación Analítica, Universidad Mayor de San Simón, Cochabamba 992, Bolivia.
  • Alsarraf J; Laboratoire d'Analyse et de Séparation des Essences Végétales (LASEVE), Centre de Recherche sur la Boréalie (CREB), Département des Sciences Fondamentales, Université du Québec à Chicoutimi, Saguenay, QC G7H 2B1, Canada.
  • Collin G; Laboratoire d'Analyse et de Séparation des Essences Végétales (LASEVE), Centre de Recherche sur la Boréalie (CREB), Département des Sciences Fondamentales, Université du Québec à Chicoutimi, Saguenay, QC G7H 2B1, Canada.
  • Pichette A; Laboratoire d'Analyse et de Séparation des Essences Végétales (LASEVE), Centre de Recherche sur la Boréalie (CREB), Département des Sciences Fondamentales, Université du Québec à Chicoutimi, Saguenay, QC G7H 2B1, Canada.
Molecules ; 26(19)2021 Sep 23.
Article em En | MEDLINE | ID: mdl-34641307
ABSTRACT
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.
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Óleos Voláteis / Asteraceae / Benzodioxóis Idioma: En Ano de publicação: 2021 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Óleos Voláteis / Asteraceae / Benzodioxóis Idioma: En Ano de publicação: 2021 Tipo de documento: Article