Stachybocin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02951 |
| CAS | 158827-61-3 |
| Molecular Weight | 899.12 |
| Molecular Formula | C52H70N2O11 |
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Description
It is a receptor antagonist produced by the strain of Stachybotrys sp. M6222. It inhibits the binding of I-ET-1 to rat ETA receptors with IC50 of 2.8 X 10-5 (mol/L). It also inhibits the binding of I-ET-1 to human ETA receptors and human ETB receptors with IC50 (mol/L) of 1.2 X 10-5 and 9.5 X 10-6, respectively.
Specification
| Synonyms | Spiro[2H-furo[2,3-e]isoindole-2,1'(2'H)-naphthalene]-7(3H)-hexanoic acid, a-[(1'R,2'R,4'aS,6'S,7'R,8'aS)-3',4',4'a,5',6,6',7',8,8',8'a-decahydro-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxospiro[2H-furo[2,3-e]isoindole-2,1'(2'H)-naphthalen]-7(3H)-yl]-3',4',4'a,5',6,6',7',8,8',8'a-decahydro-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-, (aS,1'R,2'R,4'aS,6'R,8'aS)-; Spiro[2H-furo[2,3-e]isoindole-2,1'(2'H)-naphthalene]-7(3H)-hexanoic acid, a-(3',4',4'a,5',6,6',7',8,8',8'a-decahydro-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxospiro[2H-furo[2,3-e]isoindole-2,1'(2'H)-naphthalen]-7(3H)-yl)-3',4',4'a,5',6,6',7',8,8',8'a-decahydro-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-, [1'R-[1'a[S*(1'R*,2'R*,4'aS*,6'R*,8'S*)],2'a,4'aa,6'a,7'a,8'ab]]-; AM 6222B |
| IUPAC Name | (2S)-6-[(3R,7R,8R,8aS)-3,4'-dihydroxy-4,4,7,8a-tetramethyl-6'-oxospiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,2'-3,8-dihydrofuro[2,3-e]isoindole]-7'-yl]-2-[(2R,3S,7R,8R,8aS)-2,3,4'-trihydroxy-4,4,7,8a-tetramethyl-6'-oxospiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,2'-3,8-dihydrofuro[2,3-e]isoindole]-7'-yl]hexanoic acid |
| Canonical SMILES | CC1CCC2C(C(CCC2(C13CC4=C(C=C5C(=C4O3)CN(C5=O)CCCCC(C(=O)O)N6CC7=C8C(=C(C=C7C6=O)O)CC9(O8)C(CCC1C9(CC(C(C1(C)C)O)O)C)C)O)C)O)(C)C |
| InChI | InChI=1S/C52H70N2O11/c1-26-12-14-38-47(3,4)40(58)16-17-49(38,7)51(26)21-30-35(55)19-28-32(41(30)64-51)24-53(44(28)60)18-10-9-11-34(46(62)63)54-25-33-29(45(54)61)20-36(56)31-22-52(65-42(31)33)27(2)13-15-39-48(5,6)43(59)37(57)23-50(39,52)8/h19-20,26-27,34,37-40,43,55-59H,9-18,21-25H2,1-8H3,(H,62,63)/t26-,27-,34+,37-,38?,39?,40-,43-,49+,50+,51-,52-/m1/s1 |
| InChI Key | ZRTGPZGAMCJZNA-CRDDFVEESA-N |
Properties
| Appearance | White Powder |
| Solubility | Soluble in Ethanol, Methanol, DMSO |
Reference Reading
1. Stachybocins, novel endothelin receptor antagonists, produced by Stachybotrys sp. M6222. II. Structure determination of stachybocins A, B and C
K Ogawa, M Nakamura, M Hayashi, S Yaginuma, S Yamamoto, K Furihata, K Shin-Ya, H Seta J Antibiot (Tokyo). 1995 Dec;48(12):1396-400. doi: 10.7164/antibiotics.48.1396.
The structures of stachybocins A, B and C, new endothelin receptor antagonist, were determined by NMR spectral analysis using pulse-field-gradient technique. Stachybocin A consists of two spirobenzofuran units each fused to a substituted decalin, which were connected by a lysine residue. Stachybocins B and C are derivatives of stachybocin A with an additional hydroxy group at the same position in the different decalin unit.
2. Stachybocins, novel endothelin receptor antagonists, produced by Stachybotrys sp. M6222. I. Taxonomy, fermentation, isolation and characterization
M Nakamura, Y Ito, K Ogawa, Y Michisuji, S Sato, M Takada, M Hayashi, S Yaginuma, S Yamamoto J Antibiot (Tokyo). 1995 Dec;48(12):1389-95. doi: 10.7164/antibiotics.48.1389.
Stachybocins A, B and C, novel endothelin (ET) receptor antagonists, were isolated from the culture filtrate of Stachybotrys sp. M6222. They were extracted with ethyl acetate and then purified by alumina and silica gel column chromatographies. The molecular formulae of stachybocins were determined to be C52H70N2O10 (stachybocin A) and C52H70N2O11 (stachybocins B and C). It was supposed that they consisted of spirobenzofuran and terpene units from NMR spectra. They showed the inhibitory activity of 125I-ET-1 binding to rate ETA, human ETA and human ETB receptors.
3. Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347
Bin Wu, Vanessa Oesker, Jutta Wiese, Susann Malien, Rolf Schmaljohann, Johannes F Imhoff Mar Drugs. 2014 Apr 1;12(4):1924-38. doi: 10.3390/md12041924.
A novel spirocyclic drimane coupled by two drimane fragment building blocks 2 and a new drimane 1 were identified in mycelia and culture broth of Stachybotrys sp. MF347. Their structures were established by spectroscopic means. This is the first example of spirocyclic drimane coupled by a spirodihydrobenzofuranlactam unit and a spirodihydroisobenzofuran unit; and the connecting position being N-C instead of an N and N connecting unit. Strain MF347 produced also the known spirocyclic drimanes stachybocin A (12) and stachybocin B (11) featured by two sesquiterpene-spirobenzofuran structural units connected by a lysine residue; the known spirocyclic drimanes chartarlactam O (5); chartarlactam K (6); F1839A (7); stachybotrylactam (8); stachybotramide (9); and 2α-acetoxystachybotrylactam acetate (10); as well as ilicicolin B (13), a known sesquiterpene. The relative configuration of two known spirobenzofuranlactams (3 and 4) was determined. All compounds were subjected to biological activity tests. The spirocyclic drimane 2, 11, and 12, as well as the sesquiterpene 13, exhibited antibacterial activity against the clinically relevant methicillin-resistant Staphylococcus aureus (MRSA).
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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 ╳
