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1. (Article ID: 6956)
Evidente A, Capasso R, Cutignano A, Taglialatela-Scafati O, Vurro M, Zonno MC, Motta A
Ascaulitoxin, a phytotoxic bis-amino acid N-glucoside from Ascochyta caulina
Phytochemistry 48 (1998)
1131-1137
A new unusual phytotoxic bis-amino acid N-glucoside, named ascaulitoxin, was isolated from the culture filtrate of Ascochyta caulina, the causal agent of leaf and stem necrosis of Chenopodium album, a promising mycoherbicide for the biological control of this common noxious weed. Ascaulitoxin, characterized by extensive use of NMR techniques and chemical methods as N-2-(2,4,7-triamino-5-hydroxy)-octanedioyl-β-D-glucopyranoside, showed phytotoxic activity against host and non-host plants.
phytotoxins, ascaulitoxin, Ascochyta caulina, Chenopodium album, Chenopodiaceae, mycoherbicide, N-glucosides, nonproteigenic amino acids
Publication DOI: 10.1016/S0031-9422(97)01072-8Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Dipartimento di Scienze Chimico-Agrarie, Universita di Napoli Federico II, via Universita 100, I-80055 Portici, Italy, Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, Via D. Montesano 49, I-80131 Napoli, Italy, Istituto Tossine e Micotossine da Parassiti Vegetali, CNR, Viale L. Einaudi 51, I-70125 Bari, Italy, Istituto per la Chimica di Molecole di Intersesse Biologico, CNR, Via Toiano 6, I-80072 Arco Felice, Italy
Methods: 13C NMR, 1H NMR, EI-MS, gel filtration, FAB-MS, GC-MS, TLC, acid hydrolysis, UV, TOCSY, methylation analysis, HMBC, HMQC, DEPT, NOESY, HR-EI-MS, optical rotation, acetylation analysis, COSY-45
The publication contains the following compound(s):
- Compound ID: 17716
|
b-D-Glcp1N-(1-2)-Subst
Subst = 2,4,7-triamino-5-hydroxy-octane-1,8-dioic acid = SMILES N{2}[C@H]({1}C(O)=O)C{4}[C@@H](N){5}[C@H](O)C{7}[C@H](N){8}C(O)=O |
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Structure type: monomer
; 398 [M+H]+
Trivial name: ascaulitoxin
Reference(s) to other database(s): PubChem: 102462860
- Compound ID: 17717
|
b-D-Glcp1NAc2Ac3Ac4Ac6Ac-(1-2)-Subst
Subst = 2,4,7-triamino-5-hydroxy-octane-1,8-dioic acid = SMILES N{2}[C@H]({1}C(O)=O)C{4}[C@@H](N){5}[C@H](O)C{7}[C@H](N){8}C(O)=O |
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Structure type: monomer
; 571.208969
C24H33N3O13
- Compound ID: 17718
|
b-D-Glcp1N2Ac3Ac4Ac6Ac-(1-2)-Subst7Ac
Subst = 2,4,7-triamino-5-hydroxy-octane-1,8-dioic acid = SMILES N{2}[C@H]({1}C(O)=O)C{4}[C@@H](N){5}[C@H](O)C{7}[C@H](N){8}C(O)=O |
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Structure type: monomer
; 571.204681
C24H33N3O13
- Compound ID: 17719
|
b-D-Glcp1NAc2Ac3Ac4Ac6Ac-(1-2)-Subst7Ac
Subst = 2,4,7-triamino-5-hydroxy-octane-1,8-dioic acid = SMILES N{2}[C@H]({1}C(O)=O)C{4}[C@@H](N){5}[C@H](O)C{7}[C@H](N){8}C(O)=O |
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Structure type: monomer
; 529.185326
C22H31N3O12
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2. (Article ID: 7458)
Fiore M, Rimando AM, Andolfi A, Evidente A
A new GC-MS method for the analysis of ascaulitoxin, its aglycone and 4-aminoproline from culture filtrates of Ascochyta caulina
Analytical Methods 2(2) (2010)
159-163
A new GC-MS method was developed for the analysis of ascaulitoxin, its aglycone, and 4-amino-d-proline, which are phytotoxins with potential herbicidal activity produced by Ascochyta caulina. The method involved directly treating the lyophilized culture filtrate with a derivatizing reagent, converting the mixture of toxins in the filtrate to their corresponding trimethylsilyl derivatives, and consequent analysis by EI-MS. The method is rapid, sensitive and highly specific for the identification and analysis of the toxins in a complex sample matrix. Analysis of culture filtrates using this method suggested that phytotoxicity correlates with the level of ascaulitoxin in the culture filtrate. A new method for the purification of 2,4,7-triamino-5-hydroxyoctandioic acid, the aglycone of ascaulitoxin, is also described.
GC-MS, ascaulitoxin, Ascochyta caulina, phytotoxin
Publication DOI: 10.1039/b9ay00162jJournal NLM ID: 101519733Publisher: Cambridge: RSC Pub.
Correspondence: evidente

unina.it
Institutions: U.S. Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, Oxford, USA, Dipartimento di Scienze del Suolo, della Pianta, dell'Ambiente e delle Produzioni Animali, Università di Napoli Federico II, Portici, Italy, Siena Biotech S.p.A., Strada del Petriccio e Belriguardo, Siena, Italy
Methods: GC-MS, TLC, ion-exchange chromatography, extraction, cell growth
The publication contains the following compound(s):
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