Pregnane-10,2-carbolactones from a Hawaiian Marine Sponge in the Genus Myrmekioderma.
Four new pregnanes, 3β,4β-dihydroxy-17-methyl-17α-pregna-5,13-diene-10,2-carbolactone (1), 6β-chloro-3β-hydroxy-17-methyl-17α-pregna-4,13-diene-10,2-carbolactone (2), 3β-hydroxy-6β-methoxy-17-methyl-17α-pregna-4,13-diene-10,2-carbolactone (3), and 3β,6β-dihydroxy-17-methyl-17α-pregna-4,13-diene-10,2-carbolactone (4), were isolated from an undescribed species of Myrmekioderma Ehlers along with the known pregnane carbolactone (5). The structures of the new compounds were determined by spectroscopic methods and comparison with previously described compounds. Compound 5 showed almost 4-fold activation of pregnane X receptor, while 2 inhibited BACE1 with an IC50 value of 82 μM.
Department of Chemistry, University of Hawaii at Manoa , Honolulu, Hawaii 96822, United States.
Jingqiu
J
Dai
Department of Chemistry, University of Hawaii at Manoa , Honolulu, Hawaii 96822, United States.
Wesley Y
WY
Yoshida
National Coasts and Oceans Centre, National Institute of Water and Atmospheric Research , Auckland, New Zealand , 1149.
Michelle
M
Kelly
Department of Chemistry, University of Hawaii at Manoa , Honolulu, Hawaii 96822, United States.|University of Hawaii Cancer Center, University of Hawaii at Manoa , 701 Ilalo Street, Honolulu, Hawaii 96813, United States.
Philip
P
Williams
D000818:Animals; D006254:Hawaii; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry* / Q000235:genetics; D011278:Pregnanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D007783:Lactones; D011278:Pregnanes