Phenochalasin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02390 |
| CAS | 207679-46-7 |
| Molecular Weight | 525.59 |
| Molecular Formula | C29H35NO8 |
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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
| Synonyms | Antibiotic Mer-WF 1726; 4'-Methoxycytochalasin |
| IUPAC Name | (1S,5E,7R,9S,11E,13S,14S,16R,17S,18S,19S)-7-hydroxy-19-[(4-methoxyphenyl)methyl]-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.01,18.014,16]henicosa-5,11-diene-3,8,21-trione |
| Canonical SMILES | CC1CC=CC2C3C(O3)(C(C4C2(C(=O)NC4CC5=CC=C(C=C5)OC)OC(=O)OC=CC(C1=O)(C)O)C)C |
| InChI | InChI=1S/C29H35NO8/c1-16-7-6-8-20-24-28(4,37-24)17(2)22-21(15-18-9-11-19(35-5)12-10-18)30-25(32)29(20,22)38-26(33)36-14-13-27(3,34)23(16)31/h6,8-14,16-17,20-22,24,34H,7,15H2,1-5H3,(H,30,32)/b8-6+,14-13+/t16-,17-,20-,21-,22-,24-,27+,28+,29+/m0/s1 |
| InChI Key | LVWIBRGJAUUGDB-PZOHNQLKSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 130-132°C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Phenochalasins, inhibitors of lipid droplet formation in mouse macrophages, produced by Phomopsis sp. FT-0211
H Tomoda, I Namatame, S Si, K Kawaguchi, R Masuma, M Namikoshi, S Omura J Antibiot (Tokyo). 1999 Oct;52(10):851-6. doi: 10.7164/antibiotics.52.851.
Phomopsis sp. FT-0211, a soil isolate, was found to produce inhibitors of lipid droplet formation in mouse peritoneal macrophages. Structurally related new compounds designated phenochalasins A and B were isolated from the fermentation broth of the producing strain by solvent extraction, ODS column chromatography and preparative HPLC. Phenochalasin A caused a dose-dependent reduction in the number and size of lipid droplets in macrophages without any cytotoxic effect at least up to 20 microm. On the other hand, phenochalasin B showed inhibition of lipid droplet formation with a severe cytotoxic effect on macrophages.
2. 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.
3. Chemical constituents of the ascomycete Daldinia concentrica
Dang Ngoc Quang, Toshihiro Hashimoto, Masami Tanaka, Manuela Baumgartner, Marc Stadler, Yoshinori Asakawa J Nat Prod. 2002 Dec;65(12):1869-74. doi: 10.1021/np020301h.
Four compounds, daldinone A (1), daldinone B (2), daldiniapyrone (4-methoxy-5-carbomethoxy-6-pentyl-2H-pyran-2-one, 3), and daldinialanone (22R-hydroxylanosta-7,9(11),24-trien-3-one, 4), were isolated from an ethyl acetate extract of fruit bodies of Daldinia concentrica collected in Europe. In addition, 11 known compounds, 4:5:4':5'-tetrahydroxy-1:1'-binaphthyl (5), 3,4,5-trihydroxy-1-tetralone (6), (+)-orthosporin (7), curuilignan D (8), (22E)-cholesta-4,6,8(14),22-tetraen-3-one (9), 3beta,22-dihydroxylanosta-7,9(11),24-triene (10), concentricol (11), concentricol B (12), concentricol C (13), concentricol D (14), and phenochalasin B (15), were obtained. The structures of the new compounds were elucidated by 2D NMR, MS, IR, and UV spectra and by X-ray crystallographic analysis. The absolute configurations of 1 and 4 were determined by CD spectroscopy and the modified Mosher's method, respectively. The chemotaxonomic relevance of the compounds obtained in this investigation is discussed.
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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 ╳
