Neoclerodane Diterpenoids from Scutellaria pontica

• Published in: Journal of natural products (Washington, D.C.) Vol. 60; no. 4; pp. 348 - 355
• Main Authors: Rodríguez, Benjamín, de la Torre, María C, Jimeno, María-Luisa, Bruno, Maurizio, Vassallo, Nadia, Bondì, MariaLuisa, Piozzi, Franco, Servettaz, Orietta
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.1997; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Analytical, structural and metabolic biochemistry; Biological and medical sciences; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; Chemistry, Medicinal; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; DITERPENOIDE; DITERPENOIDS; DITERPENOS; ESPECTROMETRIA; ESTRUCTURA QUIMICA; Fundamental and applied biological sciences. Psychology; LABIATAE; Life Sciences & Biomedicine; Other biological molecules; Pharmacology & Pharmacy; Plant Sciences; Science & Technology; SCUPONTINS; SCUTALKBINA A SCUTALPIN M; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; STRUCTURE CHIMIQUE; Terpenes, steroids. Hormones; JODRELLIN-A; ALPINA; GALERICULATA; INSECT ANTIFEEDANTS; Alcohol; Lactone; Oxygen heterocycle; Naphthalene derivatives; Hydroxyacid; Labiatae; Dicotyledones; Angiospermae; Absolute configuration; Epoxide; Plant origin; Bicyclic compound; Diterpene; Isolation; Above ground plant part; Spermatophyta; Acylate; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np960714g

Seven novel neoclerodane diterpenoids, scupontins A−G, have been isolated from the Me2CO extract of the aerial parts of Scutellaria pontica (1−7), together with the known neoclerodanes scutalbin A and scutalpin M. Structures 1−7 were established by exhaustive NMR spectroscopic studies and chemical transformations. Scupontins A−D (1−4, respectively) and scupontins E (5) and F (6) possess unusual [(3‘S,3‘‘S)-3‘-[(3‘‘-acetoxybutyryl)oxy]butyryloxy and [(3‘S,3‘‘S,3‘‘‘S)-3‘-[[3‘‘-[(3‘‘‘-hydroxybutyryl)oxy]butyryl]oxy]butyryl]oxy substituents, respectively, attached to the C-19 position of the neoclerodane framework. In the case of the 6α,7β-dibenzoate derivative 7 (scupontin G) its absolute configuration was established by the CD exciton chirality method.