Maria Chiara Zonno

National Research Council

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Maurizio Vurro

Institute of Sciences of Food Production

Antonio Evidente

National Research Council

Anna Andolfi

University of Naples Federico II

Alessio Cimmino

University of Naples Federico II

Angela Boari

Institute of Sciences of Food Production

Marco Masi

University of Naples Federico II

Andréa Motta

National Research Council

Angela Tuzi

University of Naples Federico II

Gennaro Pescitelli

University of Pisa

Renato Capasso

University of Naples Federico II

Cooperative Institutions

University of Naples Federico II

National Research Council

Istituto Nazionale di Fisica Nucleare, Sezione di Napoli

University of Bari Aldo Moro

Université Libre de Bruxelles

Institute of Sciences of Food Production

Federico II University Hospital

Centro di Ricerca per la Patologia Vegetale

University of Pisa

National Academies of Sciences, Engineering, and Medicine

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ChemInform Abstract: trans‐4‐Aminoproline, a Phytotoxic Metabolite with Herbicidal Activity Produced by Ascochyta caulina.

ChemInform (2000)

Antonio Evidente Anna Andolfi Maurizio Vurro Maria Chiara Zonno Andréa Motta

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Ascochyta

10.1002/chin.200019182

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Phomentrioloxin, a Fungal Phytotoxin with Potential Herbicidal Activity, and its Derivatives: A Structure–Activity Relationship Study

Journal of Agricultural and Food Chemistry (2013)

Alessio Cimmino Anna Andolfi Maria Chiara Zonno Angela Boari Ciro Troise

Phomentrioloxin is a phytotoxic geranylcyclohexenetriol produced in liquid culture by Phomopsis sp. (teleomorph: Diaporthe gulyae), a potential mycoherbicide proposed for the control of the annual weed Carthamus lanatus. In this study, seven derivatives obtained by chemical modifications of the toxin were assayed for phytotoxic, antimicrobial, and zootoxic activities, and the structure-activity relationships were examined. Each compound was tested on nonhost weedy and agrarian plants, fungi, Gram+ and Gram- bacteria, and on brine shrimp larvae. The results provide insights into an investigation of the structural requirements for activity. The hydroxy groups at C-2 and C-4 appeared to be important features for the phytotoxicity, as well as an unchanged cyclohexentriol ring. A role seemed also to be played by the unsaturations of the geranyl side chain. These findings could be useful for understanding the mechanisms of action of new natural products, for identifying the active sites, and possibly in devising new herbicides of natural origin.

Phytotoxin

Phytotoxicity

Brine shrimp

Achene

10.1021/jf4030618

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Citations (22)

Lathyroxins A and B, Phytotoxic Monosubstituted Phenols Isolated from Ascochyta lentis var. lathyri, a Fungal Pathogen of Grass Pea (Lathyrus sativus)

Journal of Natural Products (2018)

Marco Masi Paola Nocera Angela Boari Alessio Cimmino Maria Chiara Zonno

Ascochyta lentis var. lathyri has recently been reported to be the causal agent of Ascochyta blight of grass pea (Lathyrus sativus), a disease characterized by the appearance of necrotic lesions of leaves and stems. Considering the novelty of the pathogen and the possible involvement of secondary metabolites in symptom appearance, a study was carried out to ascertain the capability of this fungus to produce bioactive metabolites. Some phytotoxic phenols were isolated from the culture filtrates of the fungus. In particular, two new phytotoxic metabolites, named lathyroxins A and B, were characterized by spectroscopic methods as 4-(2-hydroxy-3,3-dimethoxypropyl)phenol and 3-(4-hydroxyphenyl)propane-1,2-diol, respectively, and the R absolute configuration of C-2 of their 2-dimethoxy- and 2,3-diol-propyl side chain was assigned. Moreover, other well-known fungal metabolites, namely, p-hydroxybenzaldehyde, p-methoxyphenol, and tyrosol, were also identified. Lathyroxins A and B showed interesting phytotoxic properties, being able to cause necrosis on leaves and to inhibit seed germination and rootlet elongation. Moreover, both of the new metabolites had no effect against bacteria, arthropods, and nematodes.

Ascochyta

Lathyrus

Phytotoxicity

Phytotoxin

Botrytis

10.1021/acs.jnatprod.7b01034

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Citations (14)

Colletochlorins E and F, New Phytotoxic Tetrasubstituted Pyran-2-one and Dihydrobenzofuran, Isolated from Colletotrichum higginsianum with Potential Herbicidal Activity

Journal of Agricultural and Food Chemistry (2017)

Marco Masi Alessio Cimmino Angela Boari Angela Tuzi Maria Chiara Zonno

A new tetrasubstituted pyran-2-one and a new dihydrobenzofuran, named colletochlorins E and F (1 and 2, respectively), were isolated from the culture filtrates of the fungus Colletotrichum higginsianum together with the already known colletochlorin A, 4-chloroorcinol, and colletopyrone. Colletochlorin E, the main metabolite, and colletochlorin F were characterized by spectroscopic (NMR, HRESIMS) and chemical methods as 3-[7-chloro-4-hydroxy-2-(1-hydroxy-1-methylethyl)-6-methyl-2,3-dihydrobenzofuran-5-ylmethyl]-4-hydroxy-5,6-dimethylpyran-2-one and 7-chloro-2-(1-hydroxy-1-methylethyl)-6-methyl-2,3-dihydrobenzofuran-4-ol, respectively. The absolute configuration 2′S of 1 was deduced by X-ray diffractometric analysis, whereas 2S of 2 was deduced by comparison of its NMR and CD data with those of 1. When assayed by leaf puncture on Sonchus arvensis and tomato leaves, 2 caused quite large necrosis (>1 cm), whereas 4-chloroorcinol proved to be the most active compound. These results were confirmed by those obtained in assays on Lemna minor and Phelipanche ramosa seed germination. Furthermore 1, colletochlorin A and colletopyrone were less or modestly active in the latter assay, respectively. Interestingly, the phytotoxicity was not associated with an antibiotic activity, whereas only 4-chloroorcinol and colletochlorin F exhibited zootoxic activity.

Pyran

Colletotrichum

10.1021/acs.jafc.6b05193

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Citations (43)

Optimization of the production of herbicidal toxins by the fungus Ascochyta caulina

Biological Control (2011)

Maurizio Vurro Anna Andolfi Angela Boari Maria Chiara Zonno Sofia Caretto

Ascochyta

10.1016/j.biocontrol.2011.10.005

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Citations (14)

CCDC 1832451: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Marco Masi Paola Nocera Maria Chiara Zonno Angela Tuzi Gennaro Pescitelli

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1zhtbm

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CCDC 1832452: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Marco Masi Paola Nocera Maria Chiara Zonno Angela Tuzi Gennaro Pescitelli

10.5517/ccdc.csd.cc1zhtcn

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ChemInform Abstract: Putaminoxins D and E from Phoma putaminum.

ChemInform (1998)

Antonio Evidente Raffaele Capasso Anna Andolfi Maurizio Vurro Maria Chiara Zonno

Phoma

10.1002/chin.199842236

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Higginsianins A and B, Two Diterpenoid α-Pyrones Produced by Colletotrichum higginsianum, with in Vitro Cytostatic Activity

Journal of Natural Products (2015)

Alessio Cimmino Véronique Mathieu Marco Masi Riccardo Baroncelli Angela Boari

Two new diterpenoid α-pyrones, named higginsianins A (1) and B (2), were isolated from the mycelium of the fungus Colletotrichum higginsianum grown in liquid culture. They were characterized as 3-[5a,9b-dimethyl-7-methylene-2-(2-methylpropenyl)dodecahydronaphtho[2,1-b]furan-6-ylmethyl]-4-hydroxy-5,6-dimethylpyran-2-one and 4-hydroxy-3-[6-hydroxy-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)decahydronaphthalen-1-ylmethyl]-5,6-dimethylpyran-2-one, respectively, by using NMR, HRESIMS, and chemical methods. The structure and relative configuration of higginsianin A (1) were confirmed by X-ray diffractometric analysis, while its absolute configuration was assigned by electronic circular dichroism (ECD) experiments and calculations using a solid-state ECD/TDDFT method. The relative and absolute configuration of higginsianin B (2), which did not afford crystals suitable for X-ray analysis, were determined by NMR analysis and by ECD in comparison with higginsianin A. 1 and 2 were the C-8 epimers of subglutinol A and diterpenoid BR-050, respectively. The evaluation of 1 and 2 for antiproliferative activity against a panel of six cancer cell lines revealed that the IC50 values, obtained with cells reported to be sensitive to pro-apoptotic stimuli, are by more than 1 order of magnitude lower than their apoptosis-resistant counterparts (1 vs >80 μM). Finally, three hemisynthetic derivatives of 1 were prepared and evaluated for antiproliferative activity. Two of these possessed IC50 values and differential sensitivity profiles similar to those of 1.

Absolute Configuration

Epimer

Furan

Methylene

10.1021/acs.jnatprod.5b00779

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Citations (43)

Agropyrenol, a Phytotoxic Fungal Metabolite, and Its Derivatives: A Structure–Activity Relationship Study

Journal of Agricultural and Food Chemistry (2013)

Alessio Cimmino Maria Chiara Zonno Anna Andolfi Ciro Troise Andréa Motta

Agropyrenol is a phytotoxic substituted salicylic aldehyde produced in liquid culture by Ascochyta agropyrina var. nana , a potential mycoherbicide proposed for the control of the perennial weed Elytrigia repens. In this study, six derivatives obtained by chemical modifications of the toxin were assayed for phytotoxic, antimicrobial, and zootoxic activities, and the structure-activity relationships were examined. Each compound was tested on non-host weedy and agrarian plants, fungi, Gram-positive and Gram-negative bacteria, and brine shrimp larvae. The results provide insights into the structure-activity relationships of agropyrenol. Both the double bond and the diol system of the 3,4-dihydroxypentenyl side chain as well as the aldehyde group at C-1 of the phenolic ring of agropyrenol proved to be important for the phytotoxicity. The lesser polar 3',4'-O,O'-isopropylidene of agropyrenol also showed significant zootoxic and slight antimicrobial activities. This finding could be useful in devising new natural herbicides for practical application in agriculture.

Phytotoxicity

Brine shrimp

Chemical structure

Repens

10.1021/jf304933z

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Citations (35)