Phytotoxic Effects and Phytochemical Fingerprinting of Hydrodistilled Oil, Enriched Fractions, and Isolated Compounds Obtained from Cryptocarya massoy (Oken) Kosterm. Bark

• Published in: Chemistry & biodiversity 2016-01, Vol.13 (1), p.66-76
• Main Authors: Rolli, Enrico, Marieschi, Matteo, Maietti, Silvia, Guerrini, Alessandra, Grandini, Alessandro, Sacchetti, Gianni, Bruni, Renato
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Anti-Bacterial Agents - toxicity; Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; Antifungal Agents - toxicity; Antimicrobial activity; Bacteria - drug effects; Cryptocarya; Cryptocarya - chemistry; Cryptocarya massoy; Cucumis sativus; Cucumis sativus - drug effects; Cucumis sativus - growth & development; Cymbopogon citratus; Dose-Response Relationship, Drug; Essential oil; Fungi - drug effects; Lycopersicon esculentum; Lycopersicon esculentum - drug effects; Lycopersicon esculentum - growth & development; Massoia lactones; Microbial Sensitivity Tests; Molecular Structure; Phytotoxicity; Plant Bark - chemistry; Plant Oils - chemistry; Plant Oils - isolation & purification; Plant Oils - pharmacology; Pyrones; Seeds - drug effects; Seeds - growth & development; Structure-Activity Relationship; Syzygium aromaticum
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.201500010

The hydrodistilled oil of Cryptocarya massoy bark was characterized by GC‐FID and GC/MS analyses, allowing the identification of unusual C10 massoia lactone (3, 56.2%), C12 massoia lactone (4, 16.5%), benzyl benzoate (1, 12.7%), C8 massoia lactone (3.4%), δ‐decalactone (5, 1.5%), and benzyl salicylate (2, 1.8%) as main constituents. The phytotoxic activities of the oil, three enriched fractions (lactone‐rich, ester‐rich, and sesquiterpene‐rich), and four constituents (compounds 1, 2, 5, and δ‐dodecalactone (6)) against Lycopersicon esculentum and Cucumis sativus seeds and seedlings were screened. At a concentration of 1000 μl/l, the essential oil and the massoia lactone‐rich fraction caused a complete inhibition of the germination of both seeds, and, when applied on tomato plantlets, they induced an 85 and 100% dieback, respectively. These performances exceeded those of the well‐known phytotoxic essential oils of Syzygium aromaticum and Cymbopogon citratus, already used in commercial products for the weed and pest management. The same substances were also evaluated against four phytopathogenic bacteria and ten phytopathogenic fungi, providing EC50 values against the most susceptible strains in the 100–500 μl/l range for the essential oil and in the 10–50 μl/l range for compound 6 and the lactone‐rich fraction. The phytotoxic behavior was related mainly to massoia lactones and benzyl esters, while a greater amount of 6 may infer a good activity against some phytopathogenic fungi. Further investigations of these secondary metabolites are warranted, to evaluate their use as natural herbicides.