| Identification | Back Directory | [Name]
fumitremorgin B | [CAS]
12626-17-4 | [Synonyms]
Lanosulin
FUMITREMORGENB
fumitremorgin B
B Fumitremorgin B
(5aR)-1,2,3,5a,6,11,12,14aβ-Octahydro-5aβ,6β-dihydroxy-9-methoxy-11-(3-methyl-2-butenyl)-12α-(2-methyl-1-propenyl)-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione
5H,14H-Pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione, 1,2,3,5a,6,11,12,14a-octahydro-5a,6-dihydroxy-9-methoxy-11-(3-methyl-2-buten-1-yl)-12-(2-methyl-1-propen-1-yl)-, (5aR,6S,12S,14aS)- | [Molecular Formula]
C27H33N3O5 | [MOL File]
12626-17-4.mol | [Molecular Weight]
479.57 |
| Chemical Properties | Back Directory | [Melting point ]
205-207 °C | [Boiling point ]
724.3±60.0 °C(Predicted) | [density ]
1.35±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: Soluble,Methanol: Soluble | [form ]
A solid | [pka]
10.74±0.60(Predicted) |
| Hazard Information | Back Directory | [Description]
This tremorgenic alkaloid is highly toxic and is elaborated by Aspergillus
jurnigatus. The structure given above has been determined from X-ray crystallography. The crystals are orthorhombic with space group P2 1212 1, a = 14.771,
b = 24.925 and c = 7.321 A with Z = 4. The absolute configuration is based
upon that of L( - )-proline formed by acid hydrolysis of the alkaloid. | [Uses]
Fumitremorgin B is a tremorgenic mycotoxin. Fumitremorgin B exhibits significant antifungal activities, with MICs of 6.25-50 μg/mL[1][2][3]. | [Definition]
ChEBI: An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi via a tryptophan-proline diketopiperazine intermediate. | [storage]
Store at -20°C | [References]
Yamazaki et al., Tetrahedron Lett., 27 (1975) |
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