Janthitrem B

Janthitrem B

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Janthitrem B
Category Mycotoxins
Catalog number BBF-05350
CAS 73561-90-7
Molecular Weight 585.77
Molecular Formula C37H47NO5

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Description

It is a tremorgenic mycotoxin produced by the strain of Penicillium Janthinellum.

Specification

Synonyms 34-deoxy-34,35-didehydro-janthitrem E; (2R,3R,4bS,6aS,9S,9aR,15bS,15cR,17aS)-10,10,12,12,15b,15c-hexamethyl-2-(prop-1-en-2-yl)-2,3,5,6,6a,7,9,9a,10,12,15,15b,15c,16,17,17a-hexadecahydro-4bH-chromeno[5',6':6,7]indeno[1,2-b]pyrano[4',3':3,4]cyclopenta[1,2-f]indole-3,4b,9-triol; 4bH-Pyrano[2'',3'':5',6']benz[1',2':6,7]indeno[1,2-b]pyrano[4',3':3,4]cyclopent[1,2-f]indole-3,4b,9-triol,2,3,5,6,6a,7,9,9a,10,12,15,15b,15c,16,17,17a-hexadecahydro-10,10,12,12,15b,15c-hexamethyl-2-(1-methylethenyl)-, (2R,3R,4bS,6aS,9S,9aR,15bS,15cR,17aS)-
IUPAC Name (2S,3R,6S,8R,9R,12S,15S,21S,22R)-2,3,23,23,25,25-hexamethyl-8-prop-1-en-2-yl-7,24-dioxa-31-azaoctacyclo[15.14.0.02,15.03,12.06,11.018,30.020,28.022,27]hentriaconta-1(17),10,18,20(28),26,29-hexaene-9,12,21-triol
Canonical SMILES CC(=C)C1C(C=C2C(O1)CCC3(C2(CCC4C3(C5=C(C4)C6=CC7=C(C=C6N5)C8=CC(OC(C8C7O)(C)C)(C)C)C)O)C)O
InChI InChI=1S/C37H47NO5/c1-18(2)31-27(39)16-25-28(42-31)10-11-35(7)36(8)19(9-12-37(25,35)41)13-23-21-14-22-20(15-26(21)38-32(23)36)24-17-33(3,4)43-34(5,6)29(24)30(22)40/h14-17,19,27-31,38-41H,1,9-13H2,2-8H3/t19-,27+,28-,29+,30+,31+,35+,36+,37+/m0/s1
InChI Key FYYNBFCZCKFSKS-QSDHUPEDSA-N
Source Janthitrems are tremorgenic mycotoxins that have been found in the fungus Penicillium janthinellum.

Properties

Boiling Point 763.3±60.0°C at 760 mmHg
Density 1.3±0.1 g/cm3

Toxicity

Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).
Mechanism Of Toxicity Janthitrem B is a tremorgenic mycotoxin. Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse.

Reference Reading

1. Identification and Structure Elucidation of Janthitrems A and D from Penicillium janthinellum and Determination of the Tremorgenic and Anti-Insect Activity of Janthitrems A and B
Jacob V Babu, Alison J Popay, Christopher O Miles, Alistair L Wilkins, Margaret E di Menna, Sarah C Finch J Agric Food Chem. 2018 Dec 19;66(50):13116-13125. doi: 10.1021/acs.jafc.8b04964. Epub 2018 Dec 7.
New compounds, 11,12-epoxyjanthitrem B (1) and 11,12-epoxyjanthitrem C (4), were isolated from Penicillium janthinellum and given the trivial names janthitrem A and janthitrem D, respectively. The known compounds janthitrem B (2) and janthitrem C (3) were also isolated, and NMR assignments were made for all four compounds. This showed that the previously published NMR assignments for 3 needed considerable revision. 1 and 2 were used as model compounds for the more complex, and highly unstable, epoxyjanthitrems that have been isolated from perennial ryegrass infected with the AR37 endophyte and which contain an epoxide group analogous to that of 1. Both 1 and 2 induced tremors in mice and reduced weight gain and food consumption of porina ( Wiseana cervinata) larvae, although 1 showed greater potency. This shows the importance of the epoxy group and suggests that epoxyjanthitrems are likely to be involved in the observed effects of the AR37 endophyte on livestock and insects.
2. Effect of culture conditions on tremorgen production by some Penicillium species
M E di Menna, D R Lauren, P A Wyatt Appl Environ Microbiol. 1986 Apr;51(4):821-4. doi: 10.1128/aem.51.4.821-824.1986.
Four strains each of seven tremorgenic Penicillium species were grown under various conditions and tested for tremorgen production by intraperitoneal injection of mice and by chemical analysis. Half of the strains had previously been found to be tremorgenic on bioassay after growth on Czapek Dox yeast extract broth or potato-milk-sucrose broth for 3 weeks at 26 degrees C. In the tests reported here nearly all previously nontremorgenic strains were either tremorgenic to mice or produced tremorgens detectable by chemical analysis but did so after longer incubation periods than used in the original screening. Bioassay was not suitable for the estimation of absolute levels but was preferable to chemical analysis when the identity of the tremorgens was not known. Species and strains within species gave different responses to changes in culture medium, incubation temperature, light irradiation, and shaking. Overall, tremorgen production was maximal at 20 or 26 degrees C, increased with time, and was reduced in shaken culture.

Spectrum

Predicted LC-MS/MS Spectrum - 10V, Positive

Experimental Conditions

Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da

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