Phenochalasin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02389 |
| CAS | |
| Molecular Weight | 495.56 |
| Molecular Formula | C28H33NO7 |
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Description
It is produced by the strain of Phomopsis sp. FT-0211. Phenochalasin A (less than 20 μmol/L) can reduce the number and size of lipid droplets in macrophages without showing any cytotoxicity.
Specification
| IUPAC Name | (1R,5Z,11E,13S,16S,17S,18S)-7-hydroxy-18-[(4-hydroxyphenyl)methyl]-7,9,15,16-tetramethyl-2,4-dioxa-19-azatricyclo[11.7.0.01,17]icosa-5,11,14-triene-3,8,20-trione |
| Canonical SMILES | CC1CC=CC2C=C(C(C3C2(C(=O)NC3CC4=CC=C(C=C4)O)OC(=O)OC=CC(C1=O)(C)O)C)C |
| InChI | InChI=1S/C28H33NO7/c1-16-6-5-7-20-14-17(2)18(3)23-22(15-19-8-10-21(30)11-9-19)29-25(32)28(20,23)36-26(33)35-13-12-27(4,34)24(16)31/h5,7-14,16,18,20,22-23,30,34H,6,15H2,1-4H3,(H,29,32)/b7-5+,13-12-/t16?,18-,20+,22+,23+,27?,28-/m1/s1 |
| InChI Key | UWGGHVBZMJIJSU-WAJZSXDNSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 143-145°C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Effect of fungal metabolites cytochalasans on lipid droplet formation in mouse macrophages
I Namatame, H Tomoda, M Arai, S Omura J Antibiot (Tokyo). 2000 Jan;53(1):19-25. doi: 10.7164/antibiotics.53.19.
Effects of seven cytochalasans including cytochalasins B, D and E and novel phenochalasins A and B were tested on cytosolic lipid droplet formation and neutral lipid synthesis in mouse peritoneal macrophages. Phenochalasin A inhibited lipid droplet formation in a dose-dependent manner at least up to 20 microM without any morphological changes in macrophages. Cytochalasins D and E also inhibited lipid droplet formation only in a narrow range of concentrations, around 1 and 0.1 microM, respectively. At higher concentrations they gave morphological changes in macrophages. The other four cytochalasans only showed severe morphological changes in macrophages. Phenochalasin A and cytochalasins D and E inhibited cholesteryl ester (CE) synthesis specifically with IC50 values of 0.61, 2.4 and 0.20 microM, respectively, while the other cytochalasans inhibited both CE and triacylglycerol syntheses. Thus, among the cytochalasans tested, phenochalasin A showed very specific inhibition of CE synthesis and gave the lowest morphological changes in macrophages, resulting in the best inhibitor of lipid droplet formation in macrophages.
2. Binding of phenochalasin A, an inhibitor of lipid droplet formation in mouse macrophages, on G-actin
Keisuke Kobayashi, Daisuke Matsuda, Hiroshi Tomoda, Taichi Ohshiro Drug Discov Ther. 2022 Sep 17;16(4):148-153. doi: 10.5582/ddt.2022.01053. Epub 2022 Aug 25.
Phenochalasin A, a unique phenol-containing cytochalasin produced by the marine-derived fungus Phomopsis sp. FT-0211, was originally discovered in a cell morphological assay of observing the inhibition of lipid droplet formation in mouse peritoneal macrophages. To investigate the mode of action and binding proteins, phenochalasin A was radio-labeled by 125I. Iodinated phenochalasin A exhibited the same biological activity as phenochalasin A. [125I]Phenochalasin A was found to be associated with an approximately 40 kDa protein, which was identified as G-actin. Furthermore, detail analyses of F-actin formation in Chinese hamster ovary cells (CHO-K1 cells) indicated that phenochalasin A (2 µM) caused elimination of F-actin formation on the apical site of the cells, suggesting that actin-oriented specific function(s) in cytoskeletal processes are affected by phenochalasin A.
3. Structure elucidation of fungal phenochalasins, novel inhibitors of lipid droplet formation in mouse macrophages
H Tomoda, I Namatame, N Tabata, K Kawaguchi, S Si, S Omura J Antibiot (Tokyo). 1999 Oct;52(10):857-61. doi: 10.7164/antibiotics.52.857.
The structures of phenochalasins A and B were elucidated by spectroscopic studies including various NMR measurements. Phenochalasins A and B have the cytochalasan skeleton of the 21,23-dioxa, 17,22-dione moiety containing unique phenyl and O-methyl phenyl residues at the C-10 position, 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 ╳
