title: Intraspecific variation in essential oil composition of the medicinal plant Lippia integrifolia (Verbenaceae). Evidence for five chemotypes.
abstract: The aerial parts of Lippia integrifolia (incayuyo) are widely used in northwestern and central Argentina for their medicinal and aromatic properties. The essential oil composition of thirty-one wild populations of L. integrifolia covering most of its natural range was analyzed by GC and GC-MS. A total of one hundred and fifty two terpenoids were identified in the essential oils. Sesquiterpenoids were the dominant components in all but one of the collections analyzed, the only exception being a sample collected in San Juan province where monoterpenoids amounted to 51%. Five clearly defined chemotypes were observed. One possessed an exquisite and delicate sweet aroma with trans-davanone as dominant component (usually above 80%). Another with an exotic floral odour was rich in oxygenated sesquiterpenoids based on the rare lippifoliane and africanane skeletons. The trans-davanone chemotype is the first report of an essential oil containing that sesquiterpene ketone as the main constituent. The absolute configuration of trans-davanone from L. integrifolia was established as 6S, 7S, 10S, the enantiomer of trans-davanone from 'davana oil' (Artemisia pallens). Wild plants belonging to trans-davanone and lippifolienone chemotypes were propagated and cultivated in the same parcel of land in Santa Maria, Catamarca. The essential oil compositions of the cultivated plants were essentially identical to the original plants in the wild, indicating that the essential oil composition is largely under genetic control. Specimens collected near the Bolivian border that initially were identified as L. boliviana Rusby yielded an essential oil practically identical to the trans-davanone chemotype of L. integrifolia supporting the recent view that L. integrifolia (Gris.) Hieron. and L. boliviana Rusby are synonymous.
authors.affiliation: INQUINOA-CONICET, Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, S. M. de Tucumán T4000INI, Argentina.
authors.forename: Guillermo
authors.initials: G
authors.lastname: Marcial
authors.affiliation: INQUINOA-CONICET, Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, S. M. de Tucumán T4000INI, Argentina.
authors.forename: Marina P
authors.initials: MP
authors.lastname: de Lampasona
authors.affiliation: INQUINOA-CONICET, Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, S. M. de Tucumán T4000INI, Argentina.
authors.forename: Marta I
authors.initials: MI
authors.lastname: Vega
authors.affiliation: INQUINOA-CONICET, Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, S. M. de Tucumán T4000INI, Argentina.
authors.forename: Emilio
authors.initials: E
authors.lastname: Lizarraga
authors.affiliation: PRONOA, Facultad de Ingeniería, Universidad Nacional de Jujuy, S. S. de Jujuy 4600, Argentina.
authors.forename: Carmen I
authors.initials: CI
authors.lastname: Viturro
authors.affiliation: Fundación Miguel Lillo, Laboratorio de Taxonomía Vegetal Fanerogámica, Miguel Lillo 251, S. M. de Tucumán 4000, Argentina.
authors.forename: Alberto
authors.initials: A
authors.lastname: Slanis
authors.affiliation: Instituto de Recursos Biológicos, CIRN, INTA, N. Repetto y Los Reseros s/n°, 1686 Hurlingham, Provincia de Buenos Aires, Argentina.
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Juárez
authors.affiliation: Instituto de Recursos Biológicos, CIRN, INTA, N. Repetto y Los Reseros s/n°, 1686 Hurlingham, Provincia de Buenos Aires, Argentina.
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Elechosa
authors.affiliation: INQUINOA-CONICET, Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, S. M. de Tucumán T4000INI, Argentina. Electronic address: ccatalan@fbqf.unt.edu.ar.
authors.forename: César A N
authors.initials: CAN
authors.lastname: Catalán
mesh_terms: D001118:Argentina; D008401:Gas Chromatography-Mass Spectrometry; D032411:Lippia / Q000737:chemistry* / Q000235:genetics*; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009822:Oils, Volatile / Q000737:chemistry*; D035261:Plant Components, Aerial / Q000737:chemistry; D010938:Plant Oils / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry* / Q000235:genetics*; D016133:Polymerase Chain Reaction; D012717:Sesquiterpenes / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D039821:Monoterpenes; D009822:Oils, Volatile; D010938:Plant Oils; D012717:Sesquiterpenes; D013729:Terpenes; C520072:davanone
keywords: Absolute configuration; Biogenesis; Chemotypes; Essential oil; Incayuyo; Lippia integrifolia; Monoterpene; Sesquiterpene; Verbenaceae; trans-Davanone