{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:57:12Z","timestamp":1787029032486,"version":"build-2736575974"},"reference-count":23,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2017,1,21]],"date-time":"2017-01-21T00:00:00Z","timestamp":1484956800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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 \u03bcM) 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.<\/jats:p>","DOI":"10.3390\/molecules22010175","type":"journal-article","created":{"date-parts":[[2017,1,23]],"date-time":"2017-01-23T10:40:33Z","timestamp":1485168033000},"page":"175","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["New Pesticidal Diterpenoids from Vellozia gigantea (Velloziaceae), an Endemic Neotropical Plant Living in the Endangered Brazilian Biome Rupestrian Grasslands"],"prefix":"10.3390","volume":"22","author":[{"given":"Mariana","family":"Ferreira","sequence":"first","affiliation":[{"name":"Department of Microbiology, Federal University of Minas Gerais, Belo Horizonte, MG 31270-901, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Charles","family":"Cantrell","sequence":"additional","affiliation":[{"name":"United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research University, MS 38677, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen","family":"Duke","sequence":"additional","affiliation":[{"name":"United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research University, MS 38677, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abbas","family":"Ali","sequence":"additional","affiliation":[{"name":"National Center for Natural Products Research, University of Mississippi, MS 38677, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luiz","family":"Rosa","sequence":"additional","affiliation":[{"name":"Department of Microbiology, Federal University of Minas Gerais, Belo Horizonte, MG 31270-901, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2017,1,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1007\/s10709-011-9561-5","article-title":"Genetic structure and variability of the endemic and vulnerable Vellozia gigantea (Velloziaceae) associated with the landscape in the Espinha\u00e7o Range, in southeastern Brazil: implications for conservation","volume":"139","author":"Lousada","year":"2011","journal-title":"Genetica"},{"key":"ref_2","unstructured":"Vanzolini, P.E., and Heyer, W.R. Patterns of geographic distribution of some plant species from the Espinhaco Range, Minas Gerais and Bahia, Brazil. Proceedings of a Workshop on Neotropical Distribution Patterns."},{"key":"ref_3","unstructured":"Joly, A.B. (1970). Conhe\u00e7a a Vegeta\u00e7\u00e3o Brasileira, University of S\u00e3o Paulo (USP)."},{"key":"ref_4","unstructured":"United Nations Educational, Scientific and Cultural Organization (UNESCO) MAB Biosphere Reserves Directory. Available online: http:\/\/www.brasilia.unesco.org\/noticias\/releases\/2005\/biosferaespinhaco."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1007\/s11104-015-2637-8","article-title":"Ecology and evolution of plant diversity in the endangered campo rupestre: A neglected conservation priority","volume":"403","author":"Silveira","year":"2016","journal-title":"Plant Soil"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"536","DOI":"10.2307\/3392159","article-title":"Two new Brazilian Velloziaceae, Vellozia auriculata and Vellozia gigantea, and a key to the related dracenoid species of Vellozia","volume":"9","author":"Menezes","year":"1999","journal-title":"Novon"},{"key":"ref_7","unstructured":"Biodiversitas (2005). Lista da Flora Brasileira Amea\u00e7ada de Extin\u00e7\u00e3o, Funda\u00e7\u00e3o Biodiversitas."},{"key":"ref_8","first-page":"31","article-title":"The growing need for biochemical bioherbicides","volume":"1172","author":"Duke","year":"2014","journal-title":"Am. Chem. Soc. Symp. Ser."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3913","DOI":"10.1016\/0031-9422(88)83043-7","article-title":"Norditerpenoids from Vellozia pusilla","volume":"27","author":"Pinto","year":"1988","journal-title":"Phytochemistry"},{"key":"ref_10","first-page":"7","article-title":"RMN 13C de diterpenoids com esqueleto cleistantano","volume":"8","author":"Pinto","year":"1985","journal-title":"Quim. Nova"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2262","DOI":"10.1016\/j.tetlet.2016.04.034","article-title":"Diterpenoids and Phenanthrenones from the Leaves and Stems of Strophioblachia Fimbricalyx","volume":"21","author":"Cheng","year":"2016","journal-title":"Tetrahedron Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1074","DOI":"10.1897\/03-256","article-title":"Dose-response relationships between herbicides with different modes of action and growth of Lemna paucicostata: An improved exotoxicological method","volume":"232","author":"Michel","year":"2004","journal-title":"Environ. Toxicol. Chem."},{"key":"ref_13","unstructured":"Herbarium of Institute of Biological Science (BHCB) of the Federal University of Minas Gerais, Brazil. Available online: http:\/\/sciweb.nybg.org\/science2\/IndexHerbariorum.asp."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2079","DOI":"10.1023\/A:1005512331061","article-title":"Investigating the mode of action of natural phytotoxins","volume":"26","author":"Dayan","year":"2000","journal-title":"J. Chem. Ecol."},{"key":"ref_15","unstructured":"R-Development-Core-Team (2015). R: A Language and Environment for Statistical Computing, R Foundation for Statistical Computing. 3.2.4 Version."},{"key":"ref_16","first-page":"257","article-title":"Composition, mosquito larvicidal, biting deterrent and antifungal activity of essential oils of different plant parts of Cupressus arizonica var. glabra (Sudw.) Little (\u2018Carolina Sapphire\u2019)","volume":"8","author":"Ali","year":"2013","journal-title":"Nat. Prod. Commun."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1016\/S0261-2194(00)00076-4","article-title":"Natural products as sources for new mechanisms of herbicidal action","volume":"19","author":"Duke","year":"2000","journal-title":"Crop Protect."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Kuo, T.M., and Gardner, H.W. (2002). Lipid Biotechnology, Marcel Dekker.","DOI":"10.1201\/9780203908198"},{"key":"ref_19","unstructured":"Mac\u00edas, F.A., Galindo, J.C.G., and Molinillo, J.M.G. (2004). Allelopathy: Chemistry and Mode of Action of Allelochemicals, CRC Press."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"25","DOI":"10.5935\/0103-5053.19910006","article-title":"Diterpenes from Vellozia bicolor","volume":"2","author":"Pinto","year":"1991","journal-title":"J. Brm. Chem. Soc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"767","DOI":"10.1016\/0031-9422(95)00906-X","article-title":"Three isomeric diterpenes from Vellozia flavicans","volume":"42","author":"Pinto","year":"1996","journal-title":"Phytochemistry"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2011","DOI":"10.1016\/0031-9422(83)80034-X","article-title":"Six diterpenes from Vellozia compacta","volume":"22","author":"Pinto","year":"1983","journal-title":"Phytochemistry"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"437","DOI":"10.1007\/s00425-014-2104-4","article-title":"Tocotrienols in Vellozia gigantea leaves: Occurrence and modulation by seasonal and plant size effects","volume":"240","author":"Morales","year":"2014","journal-title":"Planta"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/1\/175\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:26:41Z","timestamp":1760207201000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/1\/175"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,1,21]]},"references-count":23,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2017,1]]}},"alternative-id":["molecules22010175"],"URL":"https:\/\/doi.org\/10.3390\/molecules22010175","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,1,21]]}}}