Stachybocin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02950 |
| CAS | 158827-60-2 |
| Molecular Weight | 883.12 |
| Molecular Formula | C52H70N2O10 |
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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 2.3 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 1.3 X 10-5 and 7.9 X 10-6, respectively.
Specification
| Synonyms | Spirodihydrobenzofuranlactam Ⅵ; Spiro[2H-furo[2,3-e]isoindole-2,1'(2'H)-naphthalene]-7(3H)-hexanoic acid, a-[(1'R,2'R,4'aS,6'R,8'aS)-3',4',4'a,5',6,6',7',8,8',8'a-decahydro-4,6'-dihydroxy-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'-dihydroxy-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,8'ab]]-; AM 6222A |
| IUPAC Name | (2S)-2,6-bis[(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]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(CCC(C1(C)C)O)C)C)O)C)O)(C)C |
| InChI | InChI=1S/C52H70N2O10/c1-27-12-14-38-47(3,4)40(57)16-18-49(38,7)51(27)23-31-36(55)21-29-33(42(31)63-51)25-53(44(29)59)20-10-9-11-35(46(61)62)54-26-34-30(45(54)60)22-37(56)32-24-52(64-43(32)34)28(2)13-15-39-48(5,6)41(58)17-19-50(39,52)8/h21-22,27-28,35,38-41,55-58H,9-20,23-26H2,1-8H3,(H,61,62)/t27-,28-,35+,38?,39?,40-,41-,49+,50+,51-,52-/m1/s1 |
| InChI Key | OWEVPGFDPBONOA-JGNXWTFTSA-N |
Properties
| Appearance | White Powder |
| Solubility | Soluble in Ethanol, Methanol, DMSO |
Reference Reading
1. 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).
2. Symplastic continuity between companion cells and the translocation stream: long-distance transport is controlled by retention and retrieval mechanisms in the phloem
Brian G Ayre, Felix Keller, Robert Turgeon Plant Physiol. 2003 Apr;131(4):1518-28. doi: 10.1104/pp.012054.
Substantial symplastic continuity appears to exist between companion cells (CCs) and sieve elements of the phloem, which suggests that small solutes within the CC are subject to indiscriminate long-distance transport via the translocation stream. To test this hypothesis, the distributions of exotic and endogenous solutes synthesized in the CCs of minor veins were studied. Octopine, a charged molecule derived from arginine and pyruvate, was efficiently transported through the phloem but was also transferred in substantial amounts to the apoplast, and presumably other non-phloem compartments. The disaccharide galactinol also accumulated in non-phloem compartments, but long-distance transport was limited. Conversely, sucrose, raffinose, and especially stachyose demonstrated reduced accumulation and efficient transport out of the leaf. We conclude that small metabolites in the cytosol of CCs do enter the translocation stream indiscriminately but are also subject to distributive forces, such as nonselective and carrier-mediated membrane transport and symplastic dispersal, that may effectively clear a compound from the phloem or retain it for long-distance transport. A model is proposed in which the transport of oligosaccharides is an adaptive strategy to improve photoassimilate retention, and consequently translocation efficiency, in the phloem.
3. 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.
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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 ╳
