A trihomoabietane diterpenoid from Plectranthus grandidentatus and an unusual addition of acetone to the ortho-quinone system of cryptotanshinone.
A new 9alpha-(2-oxopropyl)abietane derivative (1) has been isolated from an acetone extract of Plectranthus grandidentatus. Extraction of the plant material and analytical processes carried out in the absence of acetone also revealed the presence of 1 in the plant, thus suggesting that it is a natural product rather than an artifact. Attempts at obtaining Michael adducts between acetone and para-quinone abietane diterpenoids were unsuccessful, whereas treatment of the ortho-quinone cryptotanshinone (3) with acetone under basic conditions yielded compound 2. The structures of 1 and 2 were established by 1D and 2D NMR spectroscopic studies.
Gaspar-Marques
Cristina
C
Faculdade de Farmácia da Universidade de Lisboa, Centro de Estudos de Ciências Farmacêuticas (CECF), Avenida Prof. Gama Pinto, 1649-003 Lisboa, Portugal.
Simões
M Fátima
MF
Rodríguez
Benjamín
B
D045784:Abietanes / Q000737:chemistry* / Q000302:isolation & purification*; D000096:Acetone / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010616:Phenanthrenes / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D031346:Plectranthus / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry; D013019:South Africa; D013237:Stereoisomerism
D045784:Abietanes; D010616:Phenanthrenes; D011809:Quinones; C505314:methoxyconidiol; D000096:Acetone; C037886:cryptotanshinone