Limonoids from Swietenia macrophylla and S. aubrevilleana

Mootoo, Baldwin S.; Ali, Allisha; Motilal, Ronald Kumar; Pingal, Ramish; Ramlal, Allan; Khan, Ahmad Nawaz; Reynolds, William F.; McLean, Stewart

doi:10.1021/np990199x

Cited by 56 publications

(52 citation statements)

References 13 publications

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“…Indeed, C-seco limonoids, such as azadirachtin, are the most active insecticidal compound, possessing both antifeedant and growthregulating activities. 19,20 The mexicanolide limonoids have been showed high activity against insects of Lepidoptera order, 15,21 but this is the first report of their activity on ants. The activity of oleanane triterpenes on leaf-cutting ants was already reported, showing their repellent action on Atta cephalotes workers in a feeding preferences assay.…”

Section: Resultsmentioning

confidence: 91%

Limonoids from Cipadessa fruticosa and Cedrela fissilis and their insecticidal activity

Leite¹,

Bueno²,

Oliveira³

et al. 2005

J. Braz. Chem. Soc.

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O estudo químico dos frutos de Cipadessa fruticosa (Meliaceae) permitiu o isolamento dos limonóides cipadesina B (inédito) e swietemahonolídeo. Das raízes de Cedrela fissilis (Meliaceae) foi isolado o limonóide 3β-acetoxicarapina, inédito como produto natural, juntamente com os triterpenos ácido oleanólico e ácido oleanônico. Estes compostos, e outros seis mexicanolídeos anteriormente isolados de C. fruticosa, apresentaram atividade inseticida para as formigas cortadeiras Atta sexdens rubropilosa.The chemical investigation of the fruits of Cipadessa fruticosa (Meliaceae) afforded the new limonoid cipadesin B and the known swietemahonolide. From the roots of Cedrela fissilis (Meliaceae) were isolated the limonoid 3β-acetoxycarapin, new as natural product, along with the triterpenes oleanolic and oleanonic acid. These compounds and other six mexicanolide limonoids previously isolated from C. fruticosa showed insecticidal activity against the leafcutting ants Atta sexdens rubropilosa. Keywords: Cedrela fissilis, Cipadessa fruticosa, limonoids, triterpenes, insecticidal activity IntroductionCipadessa fruticosa Blume (Meliaceae) is widely cultivated in the southwest of China. This plant has been reported to contain ent-clerodanes and labdanes diterpenoids, 1,2 limonoids, sterols, sesquiterpenoids, heneicosene derivatives and one coumarin. 3,4 We have recently reported the isolation of six mexicanolide limonoids from this plant. 5 Cedrela fissilis Vell. (Meliaceae) is a valuable tree of timber industry. In Brazil, it can be found from Amazon forest up to north of Espírito Santo State. Previous investigation of fruits and seeds from this species afforded the limonoids fissinolide, mexicanolide and 3β-hydroxyisomexicanolide. 6 In a recent investigation we have isolated several gedunin limonoids from C. fissilis. 7 Extracts and fractions from C. fruticosa and C. fissilis have been shown activity on leaf-cutting workers Atta sexdens rubropilosa. 8,9 Thus, the aim of this work was the chemical investigation of these Meliaceae species associated with biological assays against Atta sexdens rubropilosa. The study of the fruits of C. fruticosa allowed the isolation of a new mexicanolide limonoid: cipadesin B (1) and the known swietemahonolide (2). The limonoid 3β-acetoxycarapin (3) isolated from fruits of C. fissilis, is new as natural product and its spectral data are being described for the first time. The triterpenes oleanolic acid (4) and oleanonic acid (5) were also isolated from C. fissilis. The evaluation of the activity on leaf-cutting ants of these compounds, along with the following mexicanolide limonoids previously isolated from C. fruticosa: cipadesin A (6), ruageanin A (7), cipadesin (8), khayasin T (9), febrifugin (10) and mexicanolide (11) Extraction and isolation of compoundsThe powdered air-dried fruits (990 g) of C. fruticosa were subsequently extracted with hexane, CH 2 Cl 2 and MeOH. The concentrated CH 2 Cl 2 extract (10.9 g) was submitted to vacuum chromatography over silica gel using a hexane-CH 2 Cl 2 ...

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Section: Resultsmentioning

confidence: 91%

Limonoids from Cipadessa fruticosa and Cedrela fissilis and their insecticidal activity

Leite¹,

Bueno²,

Oliveira³

et al. 2005

J. Braz. Chem. Soc.

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“…For the isolation, spectroscopic characterization and absolute structure of the title compound, see : Chan et al (1976); Connolly & Labbe (1980); Connolly et al (1965); Govindachari et al (1999); Kadota, Marpaung et al (1990); Kadota, Yanagawa et al (1990); Mootoo et al (1999); Narender et al (2008); Schefer et al (2006); Taylor & Taylor (1983); Yuan et al (2010 Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).…”

Section: Related Literaturementioning

confidence: 99%

Swietenolide diacetate from the seeds ofSwietenia macrophylla

Goh

Kadir

Malek

et al. 2010

Acta Crystallogr E Struct Rep Online

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The title compound, C 31 H 38 O 10 [systematic name: (α R ,4 R ,4a R ,6a S ,7 R ,8 S ,10 R ,11 S )-methyl α,10-diacetoxy-4-(3-furyl)-4a,7,9,9-tetramethyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-7,11-methano-2 H -cycloocta[ f ][2]benzopyran-8-acetate], was isolated from the seeds of Swietenia macrophylla . The molecule contains four six-membered rings connected together in the shape of a bowl; one of the inner rings adopts a twisted chair conformation owing to the carbon–carbon double bond. The furyl substitutent is connected to an outer ring, and it points away from the bowl cavity.

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“…The barks of this plant possess anti-HIV, antimicrobial, antimalarial, and antitumor activities 14 . The barks contain triterpenoids, limonoids, flavonoids and tannins 15,16 . The objective of this research was to authenticate the antimicrobial sensitivity of the methanol extract of unripe matured fruits of Diospyros peregrina, Coccinia grandis leaves and Swietenia macrophylla bark and against some selected bacterial and fungal strains to lengthen the queue of antimicrobial herbs.…”

Section: Introductionmentioning

confidence: 99%