WF11605
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| Category | Bioactive by-products |
| Catalog number | BBF-01627 |
| CAS | 127475-47-2 |
| Molecular Weight | 692.9 |
| Molecular Formula | C38H60O11 |
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Description
WF11605 is an antagonist of leukotriene B4 (LTB4) isolated from the fungal strain F11605. It inhibited LTB4-induced chemotaxis of rabbit polymorphonuclear leukocytes (PMNLs) with an IC50 value of 1.7 x 10(-7) M and blocked 3H-LTB4 binding to PMNL membranes at 5.6 x 10(-6) M (IC50). It also inhibited LTB4-induced degranulation of rabbit PMNLs at 3.0 x 10(-6) M (IC50).
Specification
| Synonyms | WF 11605; WF-11605 |
| IUPAC Name | (1R,2R,4aS,6aR,8R,9R,10aS,12aS)-9-acetyloxy-2,4a,7,7,10a,12a-hexamethyl-2-(3-methylbutan-2-yl)-3-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4,5,6,6a,8,9,10,11,12-decahydrochrysene-1-carboxylic acid |
| Canonical SMILES | CC(C)C(C)C1(C(C2(CCC3=C(C2(CC1=O)C)CCC4C3(CC(C(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)OC(=O)C)C)C)C(=O)O)C |
| InChI | InChI=1S/C38H60O11/c1-18(2)19(3)38(10)26(41)16-37(9)22-11-12-25-34(5,6)31(49-33-29(44)28(43)27(42)24(17-39)48-33)23(47-20(4)40)15-35(25,7)21(22)13-14-36(37,8)30(38)32(45)46/h18-19,23-25,27-31,33,39,42-44H,11-17H2,1-10H3,(H,45,46)/t19?,23-,24-,25+,27-,28+,29-,30-,31+,33+,35-,36+,37-,38+/m1/s1 |
| InChI Key | FBAPXRMZLULGNA-LEAUMUBASA-N |
Properties
| Melting Point | 291°C |
Reference Reading
1. WF11605, an antagonist of leukotriene B4 produced by a fungus. II. Structure determination
N Shigematsu, E Tsujii, N Kayakiri, S Takase, H Tanaka, T Tada J Antibiot (Tokyo). 1992 May;45(5):704-8. doi: 10.7164/antibiotics.45.704.
The structure of WF11605, a novel tetracyclic triterpene glucoside, was determined to be 1. The plane structure of deacetyl-WF11605 aglycone was elucidated as 2 through the concerted application of a series of 2D NMR techniques. The relative configurations were established by X-ray crystallographic analysis of bis(p-bromobenzoyl) derivative 3 and absolute stereochemistry by CD exciton chirality method.
2. WF11605, an antagonist of leukotriene B4 produced by a fungus. I. Producing strain, fermentation, isolation and biological activity
E Tsujii, Y Tsurumi, S Miyata, K Fujie, A Kawakami, M Okamoto, M Okuhara J Antibiot (Tokyo). 1992 May;45(5):698-703. doi: 10.7164/antibiotics.45.698.
WF11605, a new antagonist of leukotriene B4 (LTB4) was isolated as a product of fungal strain F11605. The molecular formula of WF11605 was determined to be C38H60O11. WF11605 inhibited LTB4-induced chemotaxis of rabbit polymorphonuclear leukocytes (PMNLs) with an IC50 value of 1.7 x 10(-7) M and blocked 3H-LTB4 binding to PMNL membranes at 5.6 x 10(-6) M (IC50). WF11605 also inhibited LTB4-induced degranulation of rabbit PMNLs at 3.0 x 10(-6) M (IC50). However, WF11605 did not show any inhibitory effect on platelet activating factor (PAF)- and N-formyl-L-methionyl-L-leucyl-L-phenylalanine (FMLP)-induced degranulation at concentrations up to 10(-4) M. These results suggest that WF11605 is a specific antagonist of LTB4.
3. FR207944, an antifungal antibiotic from Chaetomium sp. No. 217 II. Isolation and structure elucidation
Motoo Kobayashi, Seiji Yoshimura, Takayoshi Kinoshita, Michizane Hashimoto, Seiji Hashimoto, Shigehiro Takase, Akihiko Fujie, Motohiro Hino, Yasuhiro Hori Biosci Biotechnol Biochem. 2005 May;69(5):1029-32. doi: 10.1271/bbb.69.1029.
We discovered FR207944 produced by Chaetomium sp. No. 217 in the course of screening for antifungal antibiotics from natural products. FR207944 is identical with fuscoatroside, described in the preceding paper as an anti-Aspergillus flavus agent. Determination of the relative stereochemistry of fuscoatroside was made formally by comparison with WF11605 (16-Oxo-FR207944). We confirmed the stereochemistry on the basis of single crystal X-ray analysis.
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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 ╳
