Insecticidal constituents from rhizomes of Zingiber cassumunar and Kaempferia rotunda

Nugroho, Bambang W.; Schwarz, Birgit; Wray, Victor; Proksch, Peter

doi:10.1016/0031-9422(95)00454-8

Cited by 42 publications

(20 citation statements)

References 8 publications

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“…From the result, it can be seen that all the solvent extracts were exhibited toxic effect to the beetle, T. castaneum, (Table IV) The present results supported the finding of Nugroho and Co-workers (Nugroho et al, 1996) who reported that extracts from rhizomes of Kaempferia rotunda and Zingiber cassumunar displayed significant insecticidal activity in chronic feeding bioassays against neonate larvae of Spodoptera littoralis. They also reported the presence of two phenylbutanoids compounds in Z. cassumunar rhizome, which had LD 50 values 121 and 127ppm respectively against neonate larvae of S. littoralis.…”

Section: Resultssupporting

confidence: 89%

Insecticidal activity of different fractions of petroleum ether extract of Zingiber cassumunar rhizome against Tribolium castaneum

Talukder

Haque

Zaman

et al. 2015

Bangladesh J. Sci. Ind. Res.

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An experiment was carried out to investigate the efficacy of contact toxicity of different fractions of petroleum ether extract of Zinziber cassumunar Roxb. rhizome against Tribolium castaneum. Seventy-eight different fractions of petroleum ether extract were obtained from column chromatography. Elutes having the similar TLC behavior were combined in eight fractions and were named as: MN-1, MN-2, MN-3, MN-4, MN-5, MN-6, MN-7 and MN-8. Four separate fractions were collected from the MN-1 fraction by preparative thin layer chromatography. These four parts were washed with petroleum ether, chloroform, ethyl acetate and methanol. Thereafter, these were separated by small column and designated as: M1N1, M1N2, M1N3, M1N4, M2N1, M2N2, M2N3, M2N4, M3N1, M3N2, M3N3, M3N4, M4N1 and M4N2. Fractions of M1N2, M2N2, M3N2 and M4N2 were found to be the most effective against the beetle T. castaneum after 24, 48 and 72 hours. However, some fractions exhibited the moderate effect and other fractions did not work against the beetle.Bangladesh J. Sci. Ind. Res. 50(2), 143-152, 2015

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Section: Resultssupporting

confidence: 89%

Insecticidal activity of different fractions of petroleum ether extract of Zingiber cassumunar rhizome against Tribolium castaneum

Talukder

Haque

Zaman

et al. 2015

Bangladesh J. Sci. Ind. Res.

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“…Moreover, these phenylbutanoids are also employed as simple starting materials for synthesis of various organic compounds, including natural products [4]. E-4-(2′,4′,5′-trimethoxyphenyl)buta-1,3-diene (1a) and (E)-4-(3′,4′-dimethoxyphenyl)but-1-ene (1b), metabolites of Zingiber cassumunar [5], are two such important phenylbutenes, which are known to possess numerous pharmacological activities such as antiinflammatory [6], antioxidant [7], insecticidal [8], and, most importantly, hypolipidemic [9] activities. However, both 1a and 1b are isolated together in minute amounts and their separation from each other is reported to be difficult even by preparative TLC [5].…”

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confidence: 99%

Microwave-Assisted Minutes Synthesis of Bioactive Phenylbutanoids Occurring in Zingiber cassumunar

et al. 2005

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Microwave-assisted condensation of benzaldehyde (3a,b) with acetone in aqueous sodium hydroxide adsorbed on basic alumina provides phenylbutenone (4a-4b) in 68-71% yield within 4 min, which upon further reduction with sodium borohydride and basic alumina gives phenylbutenol (5a,b) in 91-94% yield within 2 min. Dehydration of 5 with anhydrous copper (II) sulfate gives phenylbutadiene (1a,b), a metabolite of Zingiber cassumunar, within 3 min in 42-48% yield, respectively. All the steps involve environmental friendly solvents and reagents, mild reaction conditions, and overall formation of product 1a,b from 3a,b in 34-38% yield within 9 min under microwave irradiation.A large number of methoxylated phenylbutanoids have been isolated form plants sources [1] that exhibit promising biological activities [2], including modifiers in flavor and perfumery formulations [3]. Moreover, these phenylbutanoids are also employed as simple starting materials for synthesis of various organic compounds, including natural products [4]. E-4-(2′,4′,5′-trimethoxyphenyl)buta-1,3-diene (1a) and (E)-4-(3′,4′-dimethoxyphenyl)but-1-ene (1b), metabolites of Zingiber cassumunar [5], are two such important phenylbutenes, which are known to possess numerous pharmacological activities such as antiinflammatory [6], antioxidant [7], insecticidal [8], and, most importantly, hypolipidemic [9] activities. However, both 1a and 1b are isolated together in minute amounts and their separation from each other is reported to be difficult even by preparative TLC [5]. There are a few methods reported for the synthesis of these all important 1a and 1b which include multistep synthesis employing the Grignard [4] reaction, Friedel-Crafts [10] reaction, Wittig [5] reaction, and aldol condensation [11] etc. However, maintenance of anhydrous conditions, use of expensive and highly acidic catalyst, and prolonged reaction times affects the viability of all these methods. Furthermore, use of a large amount of solvents in conventional methods is neither economically nor environmentally benign. Microwave induced Organic Reaction Enhancement [12] (MORE chemistry) has created a lot of interest in the organic chemistry due to less solvent consumption, higher yields, more selectivity, mild reaction conditions, easier work-up, and rapid synthesis as compared to conventional heating. Furthermore, "dry media" synthesis using inorganic solid supports coupled with microwave irradiation have attracted significant interest worldwide, and many such microwave-assisted synthesis with solid mineral supports [13] such as alumina, silica gel, and clays have been reported with higher selectivity, yield, and purity as compared to the traditional methods. We, in this regard, report a microwave-mediated simple and efficient protocol for the synthesis of natural bioactive phenylbutanoids 1a and 1b in three steps as outlined in Scheme 1.As an endeavor towards synthesis of rare bioactive molecules [14] employing microwave irradiation, we initially decided to synthesize 1a, taking 2,4,5-trim...

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“…[3][4][5][6][7][8][9][10][11][12][13] Some of these compounds were found to have diverse biological activities such as cytotoxic, 3,4) antioxidant, [10][11][12] anti-insecticidal, 14) anti-inflammatory, [15][16][17] and uterine relaxant activity. 18) In our previous study, two phenylbutenoid dimers, (Ϯ)- (2), and four phenylbutenoids, 4-(2,4,5-trimethoxyphenyl)-but-1,3-diene (3), 4-(3,4-dimethoxyphenyl)but-1,3-diene (4), 3) (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-ol (5), and (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl acetate (6) 4) were isolated from the CHCl 3 extract of the rhizomes of Z. cassumunar.…”

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confidence: 99%

Cyclooxygenase-2 Inhibitory Phenylbutenoids from the Rhizomes of Zingiber cassumunar

Han

Kim

Jeong

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Insecticidal constituents from rhizomes of Zingiber cassumunar and Kaempferia rotunda

Cited by 42 publications

References 8 publications

Insecticidal activity of different fractions of petroleum ether extract of Zingiber cassumunar rhizome against Tribolium castaneum

Insecticidal activity of different fractions of petroleum ether extract of Zingiber cassumunar rhizome against Tribolium castaneum

Microwave-Assisted Minutes Synthesis of Bioactive Phenylbutanoids Occurring in Zingiber cassumunar

Cyclooxygenase-2 Inhibitory Phenylbutenoids from the Rhizomes of Zingiber cassumunar

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