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Hirseins A and B, Daphnane Diterpenoids from Thymelaea hirsuta That Inhibit Melanogenesis in B16 Melanoma Cells

2009; American Chemical Society; Volume: 72; Issue: 5 Linguagem: Inglês

10.1021/np800808h

1520-6025

Yusaku Miyamae, Myra O. Villareal, Manef Ben Abdrabbah, Hiroko Isoda, Hideyuki Shigemori,

Natural product bioactivities and synthesis

Two new daphnane diterpenoids, hirseins A (1) and B (2), were isolated from the aerial parts of Thymelaea hirsuta, and their structures were elucidated on the basis of spectroscopic data interpretation. Hirsein B (2) is an unusual daphnane in possessing a coumaroyl moiety. NOESY correlations of 2 implied that isomerization of the coumaroyl group in 2 was caused by equilibrium between the E (2e) and Z (2z) forms. Compounds 1 and 2 were found to inhibit melanogenesis in B16 murine melanoma cells.