Bio‐guided isolation of aromatic abietane diterpenoids from <scp><i>Salvia canariensis</i></scp> as biopesticides in the control of phytopathogenic fungi

López‐Cabeza, Rocío; Rodríguez‐Sabina, Samuel; Reyes, Carolina P; Expósito, Daniela G; Giménez, Cristina; Jiménez, Ignacio A; Cabrera, Raimundo; Bazzocchi, Isabel L

doi:10.1002/ps.7958

Cited by 4 publications

(1 citation statement)

References 43 publications

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“…Crop diseases caused by phytopathogenic fungi are a dominant cause of failed crop harvests in view of both quality and yield. Substantial losses of up to 16% potential yield were reported for wheat, rice, maize, cotton, soybean, and potato productions. , Application of fungicides is an indispensable and cost-effective means to the integrated solutions in modern agriculture. The exploration and discovery of novel antifungal chemotypes are eminent to address the challenging issues of variable resistance and pollution caused by traditional fungicides …”

Section: Introductionmentioning

confidence: 99%

Eudistomins Y-Inspired Design and Divergent Optimization of Heteroaryl Ketones for New Antifungal Leads

He,

Sun,

Kong

et al. 2024

J. Agric. Food Chem.

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The discovery of structurally distinct leads is imperative in modern agrochemical science. Inspired by eudistomins Y and the framework-related pharmaceuticals, aryl heteroaryl ketone was drawn as a common model intriguing the design and divergent synthesis of 14 kinds of heteroaryl ketones aligned with their oxime derivatives. Antifungal function-oriented phenotypical screen protruded benzothiazolyl-phenyl oxime 5a as a promising model, and the concomitant modification led to benzothiazolyl oxime 5am (EC 50 = 5.17 μM) as a superior lead than fluoxastrobin (EC 50 = 7.54 μM) against Sclerotinia sclerotiorum. Scaffold hopping of the phenyl subunit identified benzothiazolyl-pyridyl oxime as a novel antifungal scaffold accompanied by acquiring oxime 5bm with remarkable activity (EC 50 = 3.57 μM) against Pyricularia oryzae. Molecular docking showed that candidate 5am could form more hydrogen bonds with the amino acid residues of actin than metrafenone. This compound also demonstrated better curative efficacy than that of fluoxastrobin and metrafenone in controlling the plant disease caused by S. sclerotiorum. These results rationalize the discovery of antifungal candidates based on aryl heteroaryl ketone.

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Section: Introductionmentioning

confidence: 99%

Eudistomins Y-Inspired Design and Divergent Optimization of Heteroaryl Ketones for New Antifungal Leads

He,

Sun,

Kong

et al. 2024

J. Agric. Food Chem.

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Antifungal Potential of Carnosic Acid from Salvia somalensis against Phytopathogenic Fungi

Iobbi,

Lo Vetere,

Lanteri

et al. 2024

Agronomy

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The aims of the present study were (i) to characterize the dichloromethane extract of the fresh aerial parts of S. somalensis, cultivated in Liguria (Italy), (ii) to quantify carnosic acid production and (iii) to find an eco-friendly alternative approach to control diseases caused by phytopathogenic fungi. The phytochemical investigation yielded several known terpenoids, as well as a diterpene, 4α,9α-epoxy-2H-dibenzo[a,d]cyclohepten-7(5H)-one, not previously described as a plant metabolite before. The results showed a noteworthy quantity of carnosic acid (113.90 µg/mg of dried extract). The potential antifungal activity of the plant surface extract and carnosic acid against five phytopathogenic fungi (Colletotrichum coccodes, Fusarium oxysporum, Sclerotinia sclerotiorum, Botrytis cinerea and Rhizoctonia solani) was considered. A complete inhibition of C. coccodes, S. sclerotiorum and R. solani mycelium growth was observed by carnosic acid at 500 µg/mL. High inhibition values were observed against B. cinerea and F. oxysporum compared to reference active ingredients. Four different B. cinerea strains exhibited a pronounced sensitivity to carnosic acid, as well as those originating from agricultural crop scenarios where a high load of active ingredient for gray mold control was historically adopted. Additionally, the formation and development of the germinative tube in B. cinerea were greatly slowed down.

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Bioassay-Guided Fractionation Networking for Discovery of Biofungicides from Cultivated Salvia canariensis

Hernández-Álvarez,

Rodríguez-Sabina,

González-Delgado

et al. 2024

IJMS

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Considering the detrimental impacts of the current pesticides on the biotic components of the biosphere, the development of novel pesticides is vital. Plant-derived biopesticides have emerged as popular alternatives to create a safer and more sustainable agriculture model. This study aims to validate the previous bioguided fractionation of endemic Canary Islands sage, Salvia canariensis, as a potential source of botanical pesticides using a cultivation process. Accordingly, the bioassay-guided fractionation of the ethanolic extract of the leaves of cultivated S. canariensis on the phytopathogenic fungal mycelia of Botrytis cinerea, Fusarium oxysporum, and Alternaria alternata yielded six known terpenoids. Their abietane diterpenoid-type (1–5) and sesquiterpenoid (6) structures were established based on spectroscopic and spectrometric analysis. This strategy identified one abietane diterpenoid, salviol (5), as a potential candidate for the future development of biofungicides with similar potency towards the assayed phytopathogenic fungi to commercial fungicides. Salviol worked in a concentration-dependent manner. Overall, this study reinforces the potential of abietane-type diterpenoids as promising agrochemical lead compounds against infectious diseases caused by phytopathogenic fungi and validates the cultivation of S. canariensis as a potential source of plant-derived biopesticides.

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Bio‐guided isolation of aromatic abietane diterpenoids from Salvia canariensis as biopesticides in the control of phytopathogenic fungi

Cited by 4 publications

References 43 publications

Eudistomins Y-Inspired Design and Divergent Optimization of Heteroaryl Ketones for New Antifungal Leads

Eudistomins Y-Inspired Design and Divergent Optimization of Heteroaryl Ketones for New Antifungal Leads

Antifungal Potential of Carnosic Acid from Salvia somalensis against Phytopathogenic Fungi

Bioassay-Guided Fractionation Networking for Discovery of Biofungicides from Cultivated Salvia canariensis

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