The lecanindoles, nonsteroidal progestins from the terrestrial fungus Verticillium lecanii 6144.
Four new indolosesquiterpenes, lecanindoles A-D (1-4), were isolated from fermentations of the terrestrial fungus Verticillium lecanii 6144. The structures of compounds 1-4 were elucidated from analysis of spectroscopic data. Compound 2 was reduced to give 4 and its isomer 5. Compound 4 was found to be a potent and selective progesterone receptor agonist with an EC50 of 1.1 +/- 0.4 nM in a cell-based luciferase reporter assay.
Roll
Deborah M
DM
Chemical Sciences, Wyeth Research, 401 N. Middletown Road, Pearl River, New York 10965, USA. rolld@wyeth.com
Barbieri
Laurel R
LR
Bigelis
Ramunas
R
McDonald
Leonard A
LA
Arias
Daniel A
DA
Chang
Li-Ping
LP
Singh
Maya P
MP
Luckman
Scott W
SW
Berrodin
Thomas J
TJ
Yudt
Matthew R
MR
D000818:Animals; D002522:Chlorocebus aethiops; D005260:Female; D006801:Humans; D006999:Hypocreales / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008156:Luciferases / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011372:Progestins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011980:Receptors, Progesterone / Q000819:agonists*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D007211:Indoles; D011372:Progestins; D011980:Receptors, Progesterone; D012717:Sesquiterpenes; D008156:Luciferases