Heliotropium huascoense resin exudate: chemical constituents and defensive properties.
From the resinous exudate of Heliotropium huascoense a new compound, rel-(8R,9R)-carrizaloic acid, (1) (3-[rel-(8R,9R-9-hydroxy-9,13,13-trimethyl-12-oxo-10-cyclohexenyl)methyl]-4-methoxybenzoic acid), and three known flavonoids, [3-methylgalangin, 3,7-dimethylgalangin, and (-)-alpinone] have been isolated. The structure of 1 was determined by spectral and chemical methods. Several plant defensive properties of 1 (insecticidal and antifungal) have been evaluated.
Villarroel
L
L
Facultad de Química y Biología, Universidad de Santiago de Chile, Casilla 40, Correo-33, Santiago, Chile. lvillarr@lauca.usach.cl
Torres
R
R
Urzúa
A
A
Reina
M
M
Cabrera
R
R
González-Coloma
A
A
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001042:Aphids / Q000187:drug effects; D001230:Aspergillus / Q000187:drug effects; D001565:Benzoates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D028082:Boraginaceae / Q000737:chemistry*; D002677:Chile; D002855:Chromatography, Thin Layer; D001517:Coleoptera / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005670:Fusarium / Q000187:drug effects; D006458:Hemolymph / Q000187:drug effects; D062425:Hydroxybenzoate Ethers; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007814:Larva / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D012116:Resins, Plant / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D018411:Spodoptera / Q000187:drug effects; D013237:Stereoisomerism
C438065:3,7-dimethylgalangin; D000935:Antifungal Agents; D001565:Benzoates; D005419:Flavonoids; D062425:Hydroxybenzoate Ethers; D007306:Insecticides; D012116:Resins, Plant; C438066:alpinone; C438063:rel-carrizaloic acid; C438064:3-methylgalangin