The Chemistry of the Limonoids from Meliaceae
01 Jan 1984-pp 1-102
TL;DR: The chemistry of the limonoids was reviewed in this series by Dreyer (84); a more recent review is by Connolly, Overton and Polonsky (73), and taxonomic aspects have been reviewed recently by the present author.
Abstract: The purpose of this article is to review the chemistry of the limonoids isolated from plants of the natural order Meliaceae; limonoids from the Rutaceae and Cneoraceae are not included. The chemistry of the limonoids was last reviewed in this series by Dreyer (84); a more recent review is by Connolly, Overton and Polonsky (73). Taxonomic aspects have been reviewed recently by the present author (199), and chemistry and phyto-chemistry have been discussed at a recent meeting (81). The present article sets out to review advances in limonoid chemistry since the last review in this series (84); the tables however are intended to be comprehensive.
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TL;DR: Six phragmalin limonoids, named tabulalin and tabulalides A-E, were isolated from the root bark of Chukrasia tabularis by spectroscopic methods and their antifeedant properties evaluated.
91 citations
Cites background from "The Chemistry of the Limonoids from..."
..., 1997), all of the phragmalin compounds so far isolated have been reported to be present as the 1,8,9- or 8,9,14-orthoacetate derivatives (Taylor, 1984)....
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TL;DR: The in vitro efficacy on Rhipicephalus (Boophilus) microplus of extracts from Carapa guianensis seed oil, Cymbopogon martinii and Cymboogon schoenanthus leaf essential oil, and Piper tuberculatum leaf crude extract and similar synthesized substances was evaluated.
Abstract: Herbal drugs have been widely evaluated as an alternative method of parasite control, aiming to slow development of resistance and obtain low-cost biodegradable parasiticides. This study evaluated the in vitro efficacy on Rhipicephalus (Boophilus) microplus of extracts from Carapa guianensis seed oil, Cymbopogon martinii and Cymbopogon schoenanthus leaf essential oil, and Piper tuberculatum leaf crude extract and similar synthesized substances. In the immersion test, engorged females were evaluated in five dilutions ranging from 10% to 0.030625% concentration. In the larval test on impregnated filter paper, the concentration ranged from 10% to 0.02%. The treatments and controls were done in three replicates. Chemical analysis of the oils was performed by gas chromatography. The main compounds were oleic acid (46.8%) for C. guianensis and geraniol for C. martinii (81.4%), and C. schoenanthus (62.5%). The isolated and synthesized substances showed no significant effect on larvae and adult. C. martinii and P. tuberculatum showed the best efficacy on the engorged females. The LC50 and LC90 were 2.93% and 6.66% and 3.76% and 25.03%, respectively. In the larval test, the LC50 and LC90 obtained for C. martinii, P. tuberculatum, and C. schoenanthus were 0.47% and 0.63%, 0.41% and 0.79%, 0.57% and 0.96%, respectively. The fact that geraniol is present in greater quantities in C. martinii explains its higher activity in relation to C. shoenanthus. It is necessary to validate the in vivo use of safe and effective phytoparasiticidal substances. Efforts should be focused on developing formulations that enhance the efficacy in vivo and lengthen the residual period.
86 citations
TL;DR: Limonoids are highly oxidized triterpenes present in Rutaceae and Maliaceae families and potential exists for the use of limonoids against human cancer in either natural fruits, in citrus fortified with Limonoids, or in purified forms of specific limonoid.
Abstract: Nutritional research on the health benefits of substances in plant foods has recently advanced to a new stage. The research frontier has moved from study of classical vitamin deficiency diseases to study of the thousands of phytochemicals that may have important physiological effects. Recent research suggests that citrus fruit consumers may be getting another health benefit from orange juice and other citrus products called limonoids, which appear to possess substantial anticancer activity. Limonoids are highly oxidized triterpenes present in Rutaceae and Maliaceae families. Several citrus limonoids have recently been subjected to anticancer screening utilizing laboratory animals and human breast cancer cells. The experimental results described that citrus limonoids may provide substantial anticancer actions. The compounds have been shown to be free of toxic effects in animal models, so potential exists for the use of limonoids against human cancer in either natural fruits, in citrus fortified with limonoids, or in purified forms of specific limonoids. Although the initial studies are very promising they have been conducted primarily with in vitro cell culture and animal models. Thus, research is needed to determine whether the limonoids may be useful in preventing or treating cancer in humans. Copyright © 2005 Society of Chemical Industry
72 citations
TL;DR: Feeding inhibition and mortality produced by some of these extracts were comparable to and, in certain cases, slightly greater than the effects produced by comparable neem seed preparations.
Abstract: Hexane and ethanol extracts of seeds from 22 species of plants of the family Meliaceae from a number of countries were prepared. The extracts were submitted to antifeedant and toxicity bioassays utilizing fall armyworm [Spodoptera frugiperda (J.E. Smith)] (Lepidoptera: Noctuidae) larvae and striped cucumber beetle [Acalymma vittatum (F.)] (Coleoptera: Chrysomelidae) adults. Toxicity tests were also performed with brine shrimp,Anemia salina Leach. Feeding inhibition and mortality produced by some of these extracts were comparable to and, in certain cases, slightly greater than the effects produced by comparable neem (Azadiracta indica A. Juss.) seed preparations. Brine shrimp toxicity data do not extrapolate to insect activity, and vice versa.
64 citations
TL;DR: Rodriquez et al. as discussed by the authors used tropical plants as sources of antiprotozoal agents and used them in traditional medicine in Costa Rican tropical forests, where they were used in traditional medicines.
Abstract: Tropical Plants as Sources of Antiprotozoal Agents J.D. Phillipson, et al. Chemical Studies and Biological Aspects of Some Mexican Plants Used in Traditional Medicine R. Mata. Chemical and Biological Extractives of Lauraceae Species in Costa Rican Tropical Forests O.C. Castro. Zoopharmocognosy E. Rodriquez, R. Wrangham. Insectisides in Tropical Plants with NonNeurotoxic Modes of Action J.T. Arnason, et al. Insect Control Agents from Tropical Plants I. Kubo. Phytochemistry and Biological Activity of Metabolites from Tropical Meliaceae H. Rembold, I. Puhlmann. Recent Advances in the Acetogenins of Annonaceae A. Cave, et al. Phytochemical Diversity in the Order Rutales P.G. Waterman. Plant Cell Cultures and Synthetic Chemistry J.P. Kutney. Utility of the Phytochemeco Database S.M. Beckstrom-Sternberg. Index.
60 citations
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85 citations
TL;DR: In this paper, the structure elucidation of three new limonoids of the meliacin type, azadirone (I), azadiadione (II), epoxyazadiradione(III), as well as the isolation from the same plant Melia azadiirachta L. of gedunin (IVa), having a ring D lactone, are described.
76 citations
TL;DR: The six species of the genus Khaya have been examined, and tables are given showing the limonoids isolated, and the results are discussed in relation to the taxonomy of the species.
62 citations