Roselipin 2A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02206 |
| CAS | 232258-26-3 |
| Molecular Weight | 819.03 |
| Molecular Formula | C42H74O15 |
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Description
Roselipin 2A 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.
Specification
| Synonyms | Roselipin-2A |
| IUPAC Name | [(2S,3R,4S)-2,3,4,5-tetrahydroxypentyl] (2E,6E,10E)-13-[(2R,3S,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-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)COC(=O)C)O)O)O |
| InChI | InChI=1S/C42H74O15/c1-12-21(2)13-22(3)14-27(8)40(57-42-39(52)38(51)37(50)33(56-42)20-54-30(11)44)28(9)16-25(6)34(47)23(4)15-24(5)35(48)26(7)17-29(10)41(53)55-19-32(46)36(49)31(45)18-43/h15-17,21-23,26-28,31-40,42-43,45-52H,12-14,18-20H2,1-11H3/b24-15+,25-16+,29-17+/t21?,22?,23?,26?,27?,28?,31-,32-,33+,34?,35?,36+,37+,38-,39-,40?,42-/m0/s1 |
| InChI Key | NCIXLNTUPVOTSJ-FQNZKPCJSA-N |
Properties
| Appearance | Colorless Oily Matter |
Reference Reading
1. Isolation, structure, and HIV-1-integrase inhibitory activity of structurally diverse fungal metabolites
Sheo B Singh, Hiranthi Jayasuriya, Raymond Dewey, Jon D Polishook, Anne W Dombrowski, Deborah L Zink, Ziqiang Guan, Javier Collado, Gonzalo Platas, Fernando Pelaez, Peter J Felock, Daria J Hazuda J Ind Microbiol Biotechnol. 2003 Dec;30(12):721-31. doi: 10.1007/s10295-003-0101-x. Epub 2004 Jan 9.
HIV-1 integrase is a critical enzyme for replication of HIV, and its inhibition is one of the most promising new drug strategies for anti-retroviral therapy, with potentially significant advantages over existing therapies. In this report, a series of HIV-1 inhibitors isolated from the organic extract of fermentations from terrestrial fungi is described. These fungal species, belonging to a variety of genera, were collected from throughout the world following the strict guidelines of Rio Convention on Biodiversity. The polyketide- and terpenoid-derived inhibitors are represented by two naphthoquinones, a biphenyl and two triphenyls, a benzophenone, four aromatics with or without catechol units, a linear aliphatic terpenoid, a diterpenoid, and a sesterterpenoid. These compounds inhibited the coupled and strand-transfer reaction of HIV-1 integrase with an IC(50) value of 0.5-120 micro M. The bioassay-directed isolation, structure elucidation, and HIV-1 inhibitory activity of these compounds are described.
2. 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.
3. 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.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
