Megastigmane and phenolic components from Laurus nobilis L. leaves and their inhibitory effects on nitric oxide production.
Laurus nobilis L. leaves are widely used in cooking and in folk medicine. Five new megastigmane glucosides (2-4, 7, and 9) named laurosides A-E and a new phenolic glucoside 12 were isolated from the methanolic extract of L. nobilis L. leaves, along with 10 known components: megastigmane (5), megastigmane glucosides (1, 6, 8, 10, and 11), aromatic compounds (13 and 14), and flavonoids (15 and 16). The structures and relative stereochemistry have been elucidated by one- and two-dimensional nuclear magnetic resonance experiments ((1)H and (13)C NMR, DEPT, correlation spectroscopy, heteronuclear multiple quantum correlation, heteronuclear multiple bond correlation, and nuclear Overhauser enhancement spectroscopy) and by chemical derivatization. The effect of isolated compounds on nitric oxide production in lipopolysaccharide-activated murine macrophages were examined.
De Marino
Simona
S
Dipartimento di Chimica delle Sostanze Naturali and Dipartimento di Farmacologia Sperimentale, Università degli Studi di Napoli Federico II, Via D. Montesano 49, I-80131 Naples, Italy.
Borbone
Nicola
N
Zollo
Franco
F
Ianaro
Angela
A
Di Meglio
Paola
P
Iorizzi
Maria
M
D000818:Animals; D002460:Cell Line; D003512:Cyclohexanones / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology*; D005960:Glucosides / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology*; D027442:Laurus / Q000737:chemistry*; D008264:Macrophages / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D019001:Nitric Oxide Synthase / Q000378:metabolism; D052247:Nitric Oxide Synthase Type II; D045792:Norisoprenoids / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology*; D010636:Phenols / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry*
D003512:Cyclohexanones; D005960:Glucosides; D045792:Norisoprenoids; D010636:Phenols; D010936:Plant Extracts; C413264:megastigmane; D009569:Nitric Oxide; D019001:Nitric Oxide Synthase; D052247:Nitric Oxide Synthase Type II; C496317:Nos2 protein, mouse; D000432:Methanol