Cinatrin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00337 |
| CAS | 136266-34-7 |
| Molecular Weight | 372.41 |
| Molecular Formula | C18H28O8 |
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Description
It is produced by the strain of Circinotrichum falcatisporum RF-641. Cinatrin B has the activity of inhibiting phosphoesterase A2.
Specification
| Synonyms | 8-Decyl-3,4-dihydroxy-2,6-dioxo-1,7-dioxaspiro[4.4]nonane-4-carboxylic acid |
| IUPAC Name | (3R,5R)-8-decyl-3,4-dihydroxy-2,6-dioxo-1,7-dioxaspiro[4.4]nonane-4-carboxylic acid |
| Canonical SMILES | CCCCCCCCCCC1CC2(C(=O)O1)C(C(C(=O)O2)O)(C(=O)O)O |
| InChI | InChI=1S/C18H28O8/c1-2-3-4-5-6-7-8-9-10-12-11-17(16(23)25-12)18(24,15(21)22)13(19)14(20)26-17/h12-13,19,24H,2-11H2,1H3,(H,21,22)/t12?,13-,17-,18?/m0/s1 |
| InChI Key | QUSVCUTZGWKBQJ-ZVRZEWSUSA-N |
Properties
| Appearance | Colorless Powder |
| Melting Point | 190-192°C °C |
Reference Reading
1. Cinatrins, a novel family of phospholipase A2 inhibitors. I. Taxonomy and fermentation of the producing culture; isolation and structures of cinatrins
H Itazaki, K Nagashima, Y Kawamura, K Matsumoto, H Nakai, Y Terui J Antibiot (Tokyo). 1992 Jan;45(1):38-49. doi: 10.7164/antibiotics.45.38.
Cinatrins A, B, C1, C2 and C3, a family of phospholipase A2 inhibitors were isolated from the fermentation broth of Circinotrichum falcatisporum RF-641. They were found to be novel spiro-gamma-dilactones and gamma-lactones derived from 1,2,3,5-tetra or 1,2,3(or 1,2,4)-trihydroxypentadecane-1,2,3-tricarboxylic acids. Structures were elucidated by MS and NMR studies and chemical transformations. The structure of cinatrin C3 was confirmed by X-ray crystallographic analysis, and its absolute configuration was determined by comparison of the CD spectra with related compounds.
2. Enantiospecific synthesis of the phospholipase A2 inhibitor (-)-cinatrin B
Anthony N Cuzzupe, Romina Di Florio, Mark A Rizzacasa J Org Chem. 2002 Jun 28;67(13):4392-8. doi: 10.1021/jo016221k.
The first enantiospecific synthesis of phospholipase A2 (PLA2) inhibitor (-)-cinatrin B (2) from the D-arabinose derivative 9 is described. The spirolactone system was formed by an Ireland-Claisen rearrangement of the allyl ester 8 followed by hydrolysis and stereoselective iodolactonization. The stereoselectivity of the rearrangement was controlled by the asymmetry in the allylic alcohol fragment. Ester (S)-8 gave the desired rearrangement product 7 and the epimer 13 in high yield as a 73:27 ratio, respectively. The final stereocenter at C2 was introduced via a chelation-controlled addition of the Grignard reagent derived from trimethylsilylacetylene to alpha-hydroxy ketone 6. Transformation of the terminal alkyne into the methyl ester 21 followed by acetal hydrolysis and selective lactol oxidation afforded cinatrin B methyl ester (22). Base hydrolysis and acid-induced relactonization then gave (-)-cinatrin B (2).
3. Cinatrins, a novel family of phospholipase A2 inhibitors. II. Biological activities
K Tanaka, H Itazaki, T Yoshida J Antibiot (Tokyo). 1992 Jan;45(1):50-5. doi: 10.7164/antibiotics.45.50.
Cinatrins A, B and C3 inhibited phospholipase A2 purified from rat platelets in a dose-dependent manner. Cinatrin C3, the most potent component (IC50 70 microM), was noncompetitive with a Ki value of 36 microM. Cinatrins B and C3 also inhibited both porcine pancreas and Naja naja venom phospholipase A2. Inhibition of rat platelet phospholipase A2 by cinatrin C3 was independent of Ca2+ and substrate concentration. Comparison with duramycin, another phospholipase A2 inhibitor, displayed inhibition dependent on substrate concentration when phosphatidylethanolamine was the substrate. These results indicate that the inhibition of phospholipase A2 by cinatrin C3 may result from direct interaction with the enzyme.
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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 ╳
