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Erabulenol B

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Category Enzyme inhibitors
Catalog number BBF-00864
CAS
Molecular Weight 550.55
Molecular Formula C30H30O10

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

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IUPAC Name 2-[(3-acetyl-2,6-dihydroxy-5-methylphenyl)methyl]-4,6,7a-trihydroxy-5-methoxy-1,8,8,9-tetramethyl-9H-phenaleno[1,2-b]furan-3,7-dione
Canonical SMILES CC1C(C2(C(=C3C(=C(C(=O)C4=C3C(=C(C(=C4O)OC)O)C2=O)CC5=C(C(=CC(=C5O)C(=O)C)C)O)C)O1)O)(C)C
InChI InChI=1S/C30H30O10/c1-10-8-15(12(3)31)22(33)16(21(10)32)9-14-11(2)17-18-19(23(14)34)24(35)26(39-7)25(36)20(18)27(37)30(38)28(17)40-13(4)29(30,5)6/h8,13,32-33,35-36,38H,9H2,1-7H3
InChI Key RRMVDSDCIMVCIP-UHFFFAOYSA-N
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1. 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.
2. 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.

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