Sesquiterpenes and diterpenes from Ambrosia arborescens

Marinella De Leo; Mariela Beatriz Vera Saltos; Blanca Fabiola Naranjo Puente; Nunziatina De Tommasi; Alessandra Braca

doi:10.1016/j.phytochem.2010.02.002

Sesquiterpenes and diterpenes from Ambrosia arborescens

Phytochemistry. 2010 May;71(7):804-9. doi: 10.1016/j.phytochem.2010.02.002. Epub 2010 Feb 22.

Authors

Marinella De Leo¹, Mariela Beatriz Vera Saltos, Blanca Fabiola Naranjo Puente, Nunziatina De Tommasi, Alessandra Braca

Affiliation

¹ Dipartimento di Scienze Farmaceutiche, Università di Pisa, Pisa, Italy.

PMID: 20181366
DOI: 10.1016/j.phytochem.2010.02.002

Abstract

Six compounds, eudesm-11(13)-en-4beta,9beta-diol, 15R,16-dihydroxy-3-oxoisopimar-9(11)-ene, 15S,16-dihydroxy-3-oxoisopimar-9(11)-ene, 1alpha-hydroxy-7-oxo-iso-anhydrooplopanone, 10alpha-hydroxy-11,13-dihydro-5-epi-psilostachyin, and 4beta-hydroxypseudoguaian-12,6-olide 4-O-beta-d-glucopyranoside, together with 12 known sesquiterpenes, were isolated from the leaves of Ambrosia arborescens. Structures were elucidated by 1D and 2D NMR spectroscopy including 1D-TOCSY, DQF-COSY, 2D-ROESY, HSQC, and HMBC experiments, as well as by ESI mass spectrometry. The absolute configuration of the 15,16-diol moiety in 15R,16-dihydroxy-3-oxoisopimar-9(11)-ene and 15S,16-dihydroxy-3-oxoisopimar-9(11)-ene was determined using Snatzke's method. All compounds were evaluated for antiproliferative activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Ambrosia / chemistry*
Circular Dichroism
Diterpenes / chemistry
Diterpenes / isolation & purification*
Magnetic Resonance Spectroscopy
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*
Spectrometry, Mass, Electrospray Ionization

Substances

Diterpenes
Sesquiterpenes