Hirseins A and B, daphnane diterpenoids from Thymelaea hirsuta that inhibit melanogenesis in B16 melanoma cells.
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.
Miyamae
Yusaku
Y
Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba 305-8572, Japan.
Villareal
Myra Orlina
MO
Abdrabbah
Manef Ben
MB
Isoda
Hiroko
H
Shigemori
Hideyuki
H
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008543:Melanins / Q000378:metabolism; D008546:Melanoma, Experimental / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D029645:Thymelaeaceae / Q000737:chemistry*; D014416:Tunisia
D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D008543:Melanins; C550879:hirsein A; C550880:hirsein B