Voluhemins, new inhibitors of sterol O-acyltransferase, produced by Volutella citrinella BF-0440

New compounds, designated voluhemins A ( 1 ) and B ( 2 ), are isolated from the culture broth of the fungal strain Volutella citrinella BF-0440 along with structurally related known NK12838 ( 3 ). Spectroscopic data, including 1D and 2D NMR, elucidated their structures. Compounds 1 – 3 have a common...

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Bibliographic Details
Published in:Journal of antibiotics 2020-11, Vol.73 (11), p.748-755
Main Authors: Ohshiro, Taichi, Morita, Haruka, Nur, Elyza Aiman Azizah, Hosoda, Kanji, Uchida, Ryuji, Tomoda, Hiroshi
Format: Article
Language:English
Subjects:
631/154/1435/2417
631/92/349
Animals
Bacteriology
Biomedical and Life Sciences
Bioorganic Chemistry
CHO Cells - drug effects
CHO Cells - enzymology
Cricetulus
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - isolation & purification
Enzyme Inhibitors - pharmacology
Hypocreales - chemistry
Hypocreales - metabolism
Life Sciences
Magnetic Resonance Spectroscopy
Medicinal Chemistry
Microbiology
Molecular Structure
Organic Chemistry
Sterol O-Acyltransferase - antagonists & inhibitors
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Summary:New compounds, designated voluhemins A ( 1 ) and B ( 2 ), are isolated from the culture broth of the fungal strain Volutella citrinella BF-0440 along with structurally related known NK12838 ( 3 ). Spectroscopic data, including 1D and 2D NMR, elucidated their structures. Compounds 1 – 3 have a common indoline-diterpene core and two additional isoprenyl moieties. Compounds 1 and 3 contain a hemiaminal unit, while 2 is O -methylated 1 . Their inhibitory activities toward sterol O -acyltransferase (SOAT) 1 and 2 isozymes in SOAT1- and SOAT2-expressing Chinese hamster ovary (CHO) cells show that 2 selectively inhibits the SOAT2 isozyme.
ISSN:0021-8820
1881-1469
DOI:10.1038/s41429-020-0327-0