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Erabulenol A

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Category Enzyme inhibitors
Catalog number BBF-00863
CAS 20887-73-4
Molecular Weight 356.37
Molecular Formula C20H20O6

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Erabulenol A is a cholesteryl ester transfer protein (CETP) inhibitor produced by Penicillum sp. FO-5637.

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Synonyms Deoxyherqueinone; Atrovenetin monomethyl ether
IUPAC Name (9R)-4,6,7-trihydroxy-5-methoxy-1,8,8,9-tetramethyl-9H-phenaleno[1,2-b]furan-3-one
Canonical SMILES CC1C(C2=C(C3=C4C(=C2O1)C(=CC(=O)C4=C(C(=C3O)OC)O)C)O)(C)C
InChI InChI=1S/C20H20O6/c1-7-6-9(21)11-12-10(7)18-14(20(3,4)8(2)26-18)15(22)13(12)17(24)19(25-5)16(11)23/h6,8,22-24H,1-5H3/t8-/m1/s1
InChI Key KMPAOJFBQSXEAI-MRVPVSSYSA-N
Appearance Orange Powder
1. Erabulenols, inhibitors of cholesteryl ester transfer protein produced by Penicillium sp. FO-5637. II. Structure elucidation of erabulenols A and B
N Tabata, H Tomoda, S Omura J Antibiot (Tokyo). 1998 Jul;51(7):624-8. doi: 10.7164/antibiotics.51.624.
Structures of erabulenols A and B, novel fungal inhibitors of cholesteryl ester transfer protein were elucidated by spectroscopic studies including various NMR measurements. Erabulenols consist of a phenalenone skeleton and a 1,2,2-trimethyltetrahydrofuran moiety in common. Erabulenol B possesses an additional 2,6-dihydroxy-5-methyl-3-methylketonyl benzyl moiety. The absolute stereochemistry at the C-2' position of erabulenol A was deduced as S by comparison of the optical rotation with that of other related compounds.
2. Erabulenols, inhibitors of cholesteryl ester transfer protein produced by Penicillium sp. FO-5637. I.Production, isolation and biological properties
H Tomoda, N Tabata, R Masuma, S Y Si, S Omura J Antibiot (Tokyo). 1998 Jul;51(7):618-23. doi: 10.7164/antibiotics.51.618.
Penicillium sp. FO-5637, a soil isolate, was found to produce a series of inhibitors of cholesteryl ester transfer protein (CETP). Novel active compounds, designated erabulenols A and B, were isolated from the fermentation broth of the producing strain by solvent extraction, ODS column chromatography and HPLC. Erabulenols A and B inhibit human CETP activity with IC50 values of 47.7 and 58.2 microM in an in vitro assay system containing 200 microM BSA, respectively.

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