WS-7528
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| Category | Bioactive by-products |
| Catalog number | BBF-01650 |
| CAS | 132147-69-4 |
| Molecular Weight | 286.28 |
| Molecular Formula | C16H14O5 |
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Description
WS-7528 is produced by Streptomyces sp. No. 7528. It inhibited estrogen binding to its receptor protein in rat uterine cytosol.
Specification
| Synonyms | WS 7528; WS7528; BE-14348B |
| IUPAC Name | (2S,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methyl-2,3-dihydrochromen-4-one |
| Canonical SMILES | CC1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O |
| InChI | InChI=1S/C16H14O5/c1-8-15(20)14-12(19)6-11(18)7-13(14)21-16(8)9-2-4-10(17)5-3-9/h2-8,16-19H,1H3/t8-,16+/m1/s1 |
| InChI Key | GRHSSRUEUOYZIV-BCTVWOGZSA-N |
Properties
| Appearance | Pale Yellow Powder |
| Melting Point | 95-98°C |
Reference Reading
1. WS-7528, a new isoflavanone with estrogen activity isolated from Streptomyces sp. No. 7528. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities
O Nakayama, M Yagi, M Tanaka, S Kiyoto, I Uchida, M Hashimoto, M Okuhara, M Kohsaka J Antibiot (Tokyo). 1990 Nov;43(11):1394-402. doi: 10.7164/antibiotics.43.1394.
WS-7528, produced by Streptomyces sp. No. 7528, was extracted from cultured broth, purified by solvent extraction followed by chromatography on silica gel and then isolated as pale yellow powder (C16H14O5, mp 95-98 degrees C). WS-7528 inhibited estrogen binding to its receptor protein in rat uterine cytosol. The IC50 value of WS-7528 for partially purified rat uterine cytosol receptor was 5.7 x 10(-8) M. This compound was found to induce the growth of the estrogen dependent cell line MCF-7. WS-7528 was tested orally and subcutaneously in immature rats to confirm its effect on the growth of the uterus. WS-7528 has also weak anti-inflammatory activity on the carrageenin paw edema of the rat model.
2. BE-14348 substances, new specific estrogen-receptor binding inhibitors. Production, isolation, structure determination and biological properties
H Kondo, S Nakajima, N Yamamoto, A Okura, F Satoh, H Suda, M Okanishi, N Tanaka J Antibiot (Tokyo). 1990 Dec;43(12):1533-42. doi: 10.7164/antibiotics.43.1533.
Streptomyces graminofaciens BA14348, isolated from a soil sample, was found to produce new specific inhibitors of estrogen binding to its receptor. Five related substances, BE-14348A approximately E, were isolated, and their structures were determined by analyses of spectral properties. Of these substances, A was identical with the known flavanone, naringenin. On the other hand, B, C, D and E were all new compounds; the structure of B was determined to be 2(S): 3(S)-3-methyl-4',5,7-trihydroxyflavanone, C was a racemic mixture of 2(S): 3 (R) and 2(R): 3(S)-3-methyl-4',5,7-trihydroxyflavanone; D and E were 8-chloro derivatives of B and C, 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
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
