title: N,beta-D-Glucopyranosyl vincosamide, a light regulated indole alkaloid from the shoots of Psychotria leiocarpa.
abstract: From leaves of Psychotria leiocarpa, an indole alkaloid was isolated to which the structure N,beta-D-glucopyranosyl vincosamide (1) was assigned. This represents the first report of an N-glycosylated monoterpenoid indole alkaloid. In field-grown plants highest amounts of 1 were found in the leaves (2.5% of dry wt) and fruit pulp (1.5% dry wt). Lower amounts were found in the stems (0.2% dry wt) and the seeds (0.1% of dry wt), whereas the alkaloid was not detected in the roots. The accumulation of 1 in aseptic seedlings was also restricted to the shoots and increased with plant age and light exposure, independent of the supply of sucrose in the culture medium.
authors.affiliation: Faculdade Farmácia, Universidade Federal do Rio Grande do Sul, Avenida Ipiranga 2752, 90610-000 Porto Alegre, RS, Brazil.
authors.forename: Amélia T
authors.initials: AT
authors.lastname: Henriques
authors.forename: Sílvia O
authors.initials: SO
authors.lastname: Lopes
authors.forename: Juçara T
authors.initials: JT
authors.lastname: Paranhos
authors.forename: Tatiana S
authors.initials: TS
authors.lastname: Gregianini
authors.forename: Gilsane Lino
authors.initials: GL
authors.lastname: Von Poser
authors.forename: Arthur G
authors.initials: AG
authors.lastname: Fett-Neto
authors.forename: Jan
authors.initials: J
authors.lastname: Schripsema
mesh_terms: D003624:Darkness; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry* / Q000302:isolation & purification; D006031:Glycosylation; D026121:Indole Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D008027:Light; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry* / Q000302:isolation & purification; D019906:Nuclear Magnetic Resonance, Biomolecular; D018520:Plant Shoots / Q000737:chemistry* / Q000528:radiation effects; D018514:Plant Structures / Q000737:chemistry / Q000254:growth & development / Q000528:radiation effects; D032069:Psychotria / Q000737:chemistry* / Q000254:growth & development / Q000528:radiation effects; D014018:Tissue Distribution
chemical_list: D026121:Indole Alkaloids; D039821:Monoterpenes; C483219:N,beta-D-Glucopyranosyl vincosamide; D005947:Glucose