AS-186c

AS-186c

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Category Enzyme inhibitors
Catalog number BBF-03209
CAS
Molecular Weight 754.82
Molecular Formula C43H46O12

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Description

AS-186c is an acyl-CoA: cholesterol acyltransferase (ACAT) inhibitor produced by Penicillum asperosporum KY1635. The IC50 for inhibiting ACAT was 11.5 µmol/L.

Specification

Synonyms 1-(7-{2-[2,6-dihydroxy-3-(3-methylbut-2-en-1-yl)benzoyl]-3-hydroxy-5-methylphenyl}-8,12-dihydroxy-4-methoxy-10-methyl-5-oxo-7,8-dihydro-5H-dibenzo[b,h][1,5]dioxonin-3-yl)-3-methylbutyl acetate
IUPAC Name [1-[11-[2-[2,6-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-3-hydroxy-5-methylphenyl]-12,17-dihydroxy-7-methoxy-15-methyl-9-oxo-2,10-dioxatricyclo[11.4.0.03,8]heptadeca-1(13),3(8),4,6,14,16-hexaen-6-yl]-3-methylbutyl] acetate
Canonical SMILES CC1=CC2=C(C(=C1)O)OC3=C(C(=C(C=C3)C(CC(C)C)OC(=O)C)OC)C(=O)OC(C2O)C4=C(C(=CC(=C4)C)O)C(=O)C5=C(C=CC(=C5O)CC=C(C)C)O
InChI InChI=1S/C43H46O12/c1-20(2)9-10-25-11-13-29(45)35(37(25)48)39(50)34-27(16-22(5)18-30(34)46)42-38(49)28-17-23(6)19-31(47)40(28)54-32-14-12-26(33(15-21(3)4)53-24(7)44)41(52-8)36(32)43(51)55-42/h9,11-14,16-19,21,33,38,42,45-49H,10,15H2,1-8H3
InChI Key MQLUFEFCCDNPMA-UHFFFAOYSA-N

Properties

Appearance Yellow Powder
Boiling Point 885.5±65.0°C at 760 mmHg
Density 1.3±0.1 g/cm3

Reference Reading

1. Acetylcholinesterase inhibitors from a marine fungus Talaromyces sp. strain LF458
Bin Wu, Birgit Ohlendorf, Vanessa Oesker, Jutta Wiese, Susann Malien, Rolf Schmaljohann, Johannes F Imhoff Mar Biotechnol (NY). 2015 Feb;17(1):110-9. doi: 10.1007/s10126-014-9599-3. Epub 2014 Aug 10.
Two new oxaphenalenone dimers, talaromycesone A (1) and talaromycesone B (2), and a new isopentenyl xanthenone, talaroxanthenone (3), together with six known diphenyl ether derivatives, e.g., Δ(1',3'),-1'-dehydroxypenicillide (4), 1',2'-dehydropenicillide (5), vermixocin A (6), vermixocin B (7), 3'-methoxy-1'2'-dehydropenicillide (8), and AS-186c (9), were isolated from the culture broth and mycelia of a marine fungus Talaromyces sp. strain LF458. Compound 2 represents the first example of 1-nor oxaphenalenone dimer carbon skeleton. All isolated compounds were subjected to bioactivity assays. Compounds 1, 2, and 9 exhibited potent antibacterial activities with IC50 3.70, 17.36, and 1.34 μM, respectively, against human pathogenic Staphylococcus strains. Compounds 1, 3, and 9 displayed potent acetylcholinesterase inhibitory activities with IC50 7.49, 1.61, and 2.60 μM, respectively. Interestingly, phosphodiesterase PDE-4B2 was inhibited by compounds 3 (IC50 7.25 μM) and 9 (IC50 2.63 μM).
2. AS-186 compounds, new inhibitors of acyl-CoA: cholesterol acyltransferase from Penicillium asperosporum KY1635
K Kuroda, Y Morishita, Y Saito, Y Ikuina, K Ando, I Kawamoto, Y Matsuda J Antibiot (Tokyo). 1994 Jan;47(1):16-22. doi: 10.7164/antibiotics.47.16.
AS-186a, b, c, d, and g were isolated from the cultured broth of Penicillium asperosporum KY1635 as inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT). IC50 values for the effect of AS-186a, b, c, d, and g against ACAT activity of the microsomes from cholesterol-fed rabbit liver were calculated to be 22.9, 8.2, 11.5, 12.4, and 13.9 microM, respectively. Although AS-186a, and b were identical to penicillide and purpactin A, respectively, AS-186c, d, and g were found to be new compounds.

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