Title
Myrmenaphthol A, Isolated from a Hawaiian Sponge of the Genus Myrmekioderma
Author
Stephen M. Parrish, Ram P. Neupane, Mary Kay Harper, John Head, Philip G. Williams
Year
2019
Journal
Journal of Natural Products
Abstract
Four compounds (1–4) were isolated from a Hawaiian sponge of the genus Myrmekioderma. Myrmenaphthol A (1) incorporates two unusual elements into an oxidized steroidal core: a naphthyl AB-ring system and a hydroxy group at C-2. A comparison of the experimental and predicted electronic circular dichroism (ECD) spectra of 1 assigned an S configuration to the lone stereocenter (ΔESI = 0.75; similarity factor 0.8137). Known compounds, cinanthrenol A (2), 3,4-dihydroxypregna-5,17-diene-10,2-carbolactone (3), and 3,4-dihydroxypregna-5,20-diene-10,2-carbolactone (4), were also isolated. Despite literature reports of competitive inhibition at nanomolar levels for 2, neither 2 nor the structurally related 1 showed any activity against estrogen receptors at the concentrations tested.
Instrument
J-815
Keywords
Circular dichroism, Absolute configuration, Natural products, Biochemistry, Medicinal