New Pesticidal Diterpenoids from Vellozia gigantea (Velloziaceae), an Endemic Neotropical Plant Living in the Endangered Brazilian Biome Rupestrian Grasslands
1
Department of Microbiology, Federal University of Minas Gerais, Belo Horizonte, MG 31270-901, Brazil
2
United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research University, MS 38677, USA
3
National Center for Natural Products Research, University of Mississippi, MS 38677, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Molecules 2017, 22(1), 175; https://doi.org/10.3390/molecules22010175
Received: 7 December 2016 / Revised: 13 January 2017 / Accepted: 17 January 2017 / Published: 21 January 2017
(This article belongs to the Special Issue Special Issue in Honor of Professor Nikolaus (Klaus) Fischer on the Occasion of His 80th Birthday)
Vellozia gigantea is a rare, ancient, and endemic neotropical plant present in the Brazilian Rupestrian grasslands. The dichloromethane extract of V. gigantea adventitious roots was phytotoxic against Lactuca sativa, Agrostis stolonifera, and Lemna paucicostata, and showed larvicidal activity against Aedes aegypti. Phytotoxicity bioassay-directed fractionation of the extract revealed one new isopimaradiene, 8(9),15-isopimaradien-1,3,7,11-tetraone, and three new cleistanthane diterpenoids, 7-oxo-8,11,13-cleistanthatrien-3-ol, 3,20-epoxy-7-oxo-8,11,13-cleistanthatrien-3-ol, and 20-nor-3,7-dioxo-1,8,11,13-cleistanthatetraen-10-ol. These new structures are proposed based on interpretation of 1H, 13C, COSY, NOESY, HSQC, and HMBC NMR data. 8(9),15-isopimaradien-1,3,7,11-tetraone was especially phytotoxic with an IC50 value (30 μM) comparable to those of commercial herbicides clomazone, EPTC, and naptalam. In addition, 7-oxo-8,11,13-cleistanthatrien-3-ol provided 100% mortality at a concentration of 125 ppm against one-day-old Ae. aegypti larvae. Our results show that ancient and unique plants, like the endangered narrowly endemic neotropical species V. gigantea present in the Rupestrian grasslands, should also be protected because they can be sources of new bioactive compounds.
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Keywords:
diterpene; herbicide; natural products; Velloziacea
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MDPI and ACS Style
Ferreira, M.C.; Cantrell, C.L.; Duke, S.O.; Ali, A.; Rosa, L.H. New Pesticidal Diterpenoids from Vellozia gigantea (Velloziaceae), an Endemic Neotropical Plant Living in the Endangered Brazilian Biome Rupestrian Grasslands. Molecules 2017, 22, 175.
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