Myrmenaphthol A, Isolated from a Hawaiian Sponge of the Genus Myrmekioderma
| Autor: | Mary Kay Harper, Philip G. Williams, Ram P. Neupane, John D. Head, Stephen M. Parrish |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Circular dichroism
Stereochemistry Pharmaceutical Science Article Hawaii Analytical Chemistry Stereocenter chemistry.chemical_compound Non-competitive inhibition Genus Drug Discovery Animals Pharmacology Molecular Structure biology Myrmekioderma Circular Dichroism Spectrum Analysis Organic Chemistry Hydroxy group biology.organism_classification Porifera 3. Good health Sponge Complementary and alternative medicine chemistry Molecular Medicine |
| Zdroj: | J Nat Prod |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.9b00665 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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