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Roselipin 1A

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Category Enzyme inhibitors
Catalog number BBF-02204
CAS 232258-17-2
Molecular Weight 776.99
Molecular Formula C40H72O14

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Fermentation Lab

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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

Roselipin 1A is produced by the strain of Gliocladium roseum KF-1040. It inhibited the DGAT of rat hepatic microcosm with IC50 of 15~22 μmol/L.

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IUPAC Name [(2S,3R,4S)-2,3,4,5-tetrahydroxypentyl] (2E,6E,10E)-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethyl-13-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyicosa-2,6,10-trienoate
Canonical SMILES CCC(C)CC(C)CC(C)C(C(C)C=C(C)C(C(C)C=C(C)C(C(C)C=C(C)C(=O)OCC(C(C(CO)O)O)O)O)O)OC1C(C(C(C(O1)CO)O)O)O
InChI InChI=1S/C40H72O14/c1-11-20(2)12-21(3)13-26(8)38(54-40-37(50)36(49)35(48)31(18-42)53-40)27(9)15-24(6)32(45)22(4)14-23(5)33(46)25(7)16-28(10)39(51)52-19-30(44)34(47)29(43)17-41/h14-16,20-22,25-27,29-38,40-50H,11-13,17-19H2,1-10H3/b23-14+,24-15+,28-16+/t20?,21?,22?,25?,26?,27?,29-,30-,31+,32?,33?,34+,35+,36-,37-,38?,40-/m0/s1
InChI Key PQKVMUDGLBZIJJ-GEXIMXJRSA-N
Appearance White Powder
Solubility Soluble in Methanol, Ethanol, Acetone, and Ethyl acetate
1. Structure elucidation of roselipins, inhibitors of diacylglycerol acyltransferase produced by Gliocladium roseum KF-1040
N Tabata, Y Ohyama, H Tomoda, T Abe, M Namikoshi, S Omura J Antibiot (Tokyo). 1999 Sep;52(9):815-26. doi: 10.7164/antibiotics.52.815.
The structures of roselipins 1A, 1B, 2A and 2B were elucidated by spectroscopic studies including 1H-1H COSY, 13C-1H COSY, 13C-1H HMQC and 13C-1H HMBC NMR experiments, and degradation experiments. They have the common skeleton of 2,4,6,8,10,12,14,16,18-nonamethyl-5,9,13-trihydroxy-2E,6E, 10E-icosenoic acid modified with a D-mannose and a D-arabinitol. Roselipin A and B groups were stereoisomers at the arabinitol moiety, which esterified the fatty acid from the different terminal hydroxy residue. Roselipin 2 group was 6"-O-acetyl roselipin 1 group.
2. Core structure in roselipins essential for eliciting inhibitory activity against diacylglycerol acyltransferase
Hiroshi Tomoda, Noriko Tabata, Yukako Ohyama, Satoshi Omura J Antibiot (Tokyo). 2003 Jan;56(1):24-9. doi: 10.7164/antibiotics.56.24.
Fungal roselipins, discovered as inhibitors of diacylglycerol acyltransferase (DGAT), consist of three parts; highly methylated C20 fatty acid, mannose and arabinitol. Demannosyl and/or dearabinitoyl roselipins were prepared chemically or enzymatically. Demannnosyl roselipins conserved the DGAT inhibitory activity, but the others lost the activity, indicating that the arabinitoyl fatty acid core is essential for eliciting the activity.
3. Roselipins, inhibitors of diacylglycerol acyltransferase, produced by Gliocladium roseum KF-1040
H Tomoda, Y Ohyama, T Abe, N Tabata, M Namikoshi, Y Yamaguchi, R Masuma, S Omura J Antibiot (Tokyo). 1999 Aug;52(8):689-94. doi: 10.7164/antibiotics.52.689.
Gliocladium roseum KF-1040, a marine isolate, was found to produce a series of new inhibitors of diacylglycerol acyltransferase (DGAT). Four active compounds, designated roselipins 1A, 1B, 2A and 2B, were isolated from the fermentation broth of the producing strain by solvent extraction, ODS column chromatography and preparative HPLC. The highest production of roselipins was observed when cultured in the medium containing natural sea water. Roselipins inhibit DGAT activity with IC50 values of 15 approximately 22 microM in an enzyme assay system using rat liver microsomes.

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