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Fitoterapia. 2014 Dec;99:341-6. doi: 10.1016/j.fitote.2014.08.021. Epub 2014 Aug 27.

Antifungal compounds from turmeric and nutmeg with activity against plant pathogens.

Author information

1
National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
2
United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, The University of Mississippi, University, MS 38677, USA.
3
Department of Medicinal Chemistry, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
4
National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA; Department of Medicinal Chemistry, School of Pharmacy, The University of Mississippi, University, MS 38677, USA. Electronic address: cutler@olemiss.edu.

Abstract

The antifungal activity of twenty-two common spices was evaluated against plant pathogens using direct-bioautography coupled Colletotrichum bioassays. Turmeric, nutmeg, ginger, clove, oregano, cinnamon, anise, fennel, basil, black cumin, and black pepper showed antifungal activity against the plant pathogens Colletotrichum acutatum, Colletotrichum fragariae, and Colletotrichum gloeosporioides. Among the active extracts, turmeric and nutmeg were the most active and were chosen for further investigation. The bioassay-guided fractionation led to the isolation of three compounds from turmeric (1-3) and three compounds from nutmeg (4-6). Their chemical structures were elucidated by spectroscopic analysis including HR-MS, 1D, and 2D NMR as curcumin (1), demethoxycurcumin (2) and bisdemethoxy-curcumin (3), erythro-(7R,8R)-Δ(8')-4,7-dihydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan (4), erythro-(7R,8R)-Δ8'-7-acetoxy-3,4,3',5'-tetra-methoxy-8-O-4'-neolignan (5), and 5-hydroxy-eugenol (6). The isolated compounds were subsequently evaluated using a 96-well microbioassay against plant pathogens. At 30 μM, compounds 2 and 3 possessed the most antifungal activity against Phomopsis obscurans and Phomopsis viticola, respectively.

KEYWORDS:

Antifungal; Curcuminoids; Neolignans; Nutmeg; Plant pathogens; Spices; Turmeric

PMID:
25173461
DOI:
10.1016/j.fitote.2014.08.021
[Indexed for MEDLINE]

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