LOLITREM B
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Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 11947793
Name
LOLITREM B
IUPAC name
(3S,4aR,4bR,5aS,5bS,7aS,9aR,12aR,16bS,16cR,18aS,19aS)-5b-hydroxy-1,1,10,10,12,12,16b,16c-octamethyl-3-(2-methylprop-1-en-1-yl)-1,4a,4b,5b,6,7a,9,9a,10,12,12a,16,16b,16c,17,18,18a,19a-octadecahydro-7H-[1,3]dioxino[5'',4'':2',3']oxireno[2'',3'':4',4a']chromeno[5',6':6,7]indeno[1,2-b]isobenzofuro[5,6-e]indol-13(8H)-one
SMILES
CC(=C[C@H]1O[C@H]2[C@@H]3[C@@]4(O3)[C@H](CC[C@]5([C@]4(CC[C@@H]6[C@@]5(C7=C(C6)C8=C(N7)C=CC9=C8C[C@@H]3[C@@H](C9=O)C(OC3(C)C)(C)C)C)O)C)O[C@@H]2C(O1)(C)C)C
Molecular formula
C42H55NO7
Molecular weight
685.90 g/mol
Monoisotopic mass
685.3979 Da
Pathway:
Superclass:
Class:
Glycoside:
No
Chemical classification: NPClassifier (Kim et al., 2021)
| Plant | Plant part | Amount | Reference |
|---|---|---|---|
| Lolium perenne L. | - | - |
Gallagher, R.T., Hawkes, A.D., Steyn, P.S., Vleggaar, R. (1984). Tremorgenic neurotoxins from perennial ryegrass causing ryegrass staggers disorder of livestock: structure elucidation of Lolitrem B. Chem Commun, (9), 614-616 doi:10.1039/c39840000614
|
| Lolium perenne L. | fruit | - |
Weedon, C.M., Mantle, P.G. (1987). Paxilline biosynthesis by acremonium loliae. a step towards defining the origin of lolitrem neurotoxins. Phytochemistry, 26(4), 969-971 doi:10.1016/s0031-9422(00)82327-4
|
| Lolium perenne L. | seed | - |
Miles, C.O., Munday, S.C., Wilkins, A.L., Ede, R.M., Towers, N.R. (1994). Large-scale isolation of lolitrem b and structure determination of lolitrem E. J Agr Food Chem, 42(7), 1488-1492 doi:10.1021/jf00043a018
|