Feigrisolide A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00905 |
| CAS | 313949-16-5 |
| Molecular Weight | 202.25 |
| Molecular Formula | C10H18O4 |
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Description
Feigrisolide A is a lactone produced by Streptomyces griseus. It has moderate inhibitory activity of 3α-hydroxysterol dehydrogenase.
Specification
| IUPAC Name | (3R,4S,7S)-4-hydroxy-7-[(2S)-2-hydroxypropyl]-3-methyloxepan-2-one |
| Canonical SMILES | CC1C(CCC(OC1=O)CC(C)O)O |
| InChI | InChI=1S/C10H18O4/c1-6(11)5-8-3-4-9(12)7(2)10(13)14-8/h6-9,11-12H,3-5H2,1-2H3/t6-,7+,8-,9-/m0/s1 |
| InChI Key | FZPDDULMNZBINH-KZVJFYERSA-N |
Properties
| Appearance | Oil |
Reference Reading
1. Feigrisolides A, B, C and D, new lactones with antibacterial activities from Streptomyces griseus
Y Q Tang, I Sattler, R Thiericke, S Grabley, X Z Feng J Antibiot (Tokyo). 2000 Sep;53(9):934-43. doi: 10.7164/antibiotics.53.934.
Four new lactone compounds, named feigrisolides A to D (1 to 4), have been isolated from Streptomyces griseus. The chemical structures were determined by detail analysis of their spectroscopic data and chemical transformations. Structurally, the feigrisolides A (1) and B (2) are hepta-lactones, feigrisolide C (3) and D (4) are 16-membered macrodiolides. Biological studies showed that feigrisolide B (2) exhibited strong antibacterial, as well as medium cyctotoxic, and antiviral activities. Feigrisolides A (1), C (3) and D (4) are medium inhibitors of 3alpha-hydroxysteroid-dehydrogenase (3alpha-HSD) inhibiting activity.
2. Feigrisolide C: structural revision and synthesis
Woo Han Kim, Jae Hoon Jung, Eun Lee J Org Chem. 2005 Sep 30;70(20):8190-2. doi: 10.1021/jo051107d.
[Carbohydrate structure: see text] The original macrodiolide structure proposed for feigrisolide C was incorrect. The true structure of feigrisolide C was identified as (2'S,3'S,6'R,8'R)-homononactoyl (2R,3R,6S,8S)-nonactic acid, which was confirmed by total synthesis.
3. Stereoselective synthesis of the published structure of feigrisolide A. Structural revision of feigrisolides A and B
Paula Alvarez-Bercedo, Juan Murga, Miguel Carda, J Alberto Marco J Org Chem. 2006 Jul 21;71(15):5766-9. doi: 10.1021/jo060314q.
The total synthesis of the proposed structure of feigrisolide A is reported. Ethyl (S)-3-hydroxybutyrate was the chiral starting material. A Brown asymmetric allylation and an Evans aldol reaction were key steps of the synthesis. The NMR data of the synthetic product are different from those of the natural product. The published structure of feigrisolide A is therefore erroneous. A subsequent comparison of spectral data strongly suggests that feigrisolides A and B are identical with (-)-nonactic acid and (+)-homononactic acid, respectively.
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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 ╳
