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Journal ArticleDOI

Structural and synthetic studies on the retrofractamides—amide constituents of Piper retrofractum

05 Feb 1985-Phytochemistry (Pergamon)-Vol. 24, Iss: 2, pp 279-284

Abstract: Two new unsaturated amides, retrofractamides A and C, were isolated from the total above-ground parts of Piper retrofractum . Retrofractamide A was shown to be N -isobutyl-9(3′,4′-methylenedioxyphenyl)2 E ,4 E ,8 E -nonatrienamide from spectroscopic and chemical investigations. The structure 6 for retrofractamide C was suggested from spectroscopic and chemical studies and was confirmed by a total stereoselective synthesis. The presence of sesamin and 3,4,5-trimethoxydihydrocinnamic acid as well as two higher homologues of retrofractamide A, viz. pipericide (retrofractamide B) and retrofractamide D was demonstrated. The synthesis of pipericide was also achieved.
Topics: Piper retrofractum (60%)
Citations
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Journal ArticleDOI
Abstract: The secondary metabolites isolated from Piper species for the period 1907 to June 1996 have been reviewed. Nearly six hundred chemical constituents belonging to different classes of bioactive compounds are listed together with their source(s) and references. © 1997 Elsevier Science Ltd

802 citations


Journal ArticleDOI
Il-Kwon Park1, Sang-Gil Lee1, Sang-Chul Shin1, Ji-Doo Park1  +1 moreInstitutions (1)
TL;DR: Structural-activity relationships indicate that the N-isobutylamine moiety might play a crucial role in the larvicidal activity, but the methylenedioxyphenyl moiety does not appear essential for toxicity.
Abstract: The insecticidal activity of materials derived from the fruits of Piper nigrum against third instar larvae of Culex pipiens pallens, Aedes aegypti, and A. togoi was examined and compared with that of commercially available piperine, a known insecticidal compound from Piper species. The biologically active constituents of P. nigrum fruits were characterized as the isobutylamide alkaloids pellitorine, guineensine, pipercide, and retrofractamide A by spectroscopic analysis. Retrofractamide A was isolated from P. nigrum fruits as a new insecticidal principle. On the basis of 48-h LC(50) values, the compound most toxic to C. pipiens pallens larvae was pipercide (0.004 ppm) followed by retrofractamide A (0.028 ppm), guineensine (0.17 ppm), and pellitorine (0.86 ppm). Piperine (3.21 ppm) was least toxic. Against A. aegypti larvae, larvicidal activity was more pronounced in retrofractamide A (0.039 ppm) than in pipercide (0.1 ppm), guineensine (0.89 ppm), and pellitorine (0.92 ppm). Piperine (5.1 ppm) was relatively ineffective. Against A. togoi larvae, retrofractamide A (0.01 ppm) was much more effective, compared with pipercide (0.26 ppm), pellitorine (0.71 ppm), and guineensine (0.75 ppm). Again, very low activity was observed with piperine (4.6 ppm). Structure-activity relationships indicate that the N-isobutylamine moiety might play a crucial role in the larvicidal activity, but the methylenedioxyphenyl moiety does not appear essential for toxicity. Naturally occurring Piper fruit-derived compounds merit further study as potential mosquito larval control agents or as lead compounds.

196 citations


Journal ArticleDOI
TL;DR: Piper crassinervium, P. aduncum,P.
Abstract: Piper crassinervium, P aduncum, P hostmannianum, and P gaudichaudianum contain the new benzoic acid derivatives crassinervic acid (1), aduncumene (8), hostmaniane (18), and gaudichaudianic acid (20), respectively, as major secondary metabolites Additionally, 19 known compounds such as benzoic acids, chromenes, and flavonoids were isolated and identified The antifungal activity of these compounds was evaluated by bioautographic TLC assay against Cladosporium cladosporioides and C sphaerospermum

169 citations


Journal ArticleDOI
TL;DR: The n-hexane extracts of 19 Piper species, predominantly from China, were screened for their 5-lipoxygenase (5-LOX) and cyclo oxygengenase-1 (COX-1) inhibitory potential and showed considerable inhibitory activity against at least one of these two key enzymes of the arachidonic acid metabolism.
Abstract: The n-hexane extracts of 19 Piper species, predominantly from China, were screened for their 5-lipoxygenase (5-LOX) and cyclooxygenase-1 (COX-1) inhibitory potential. Many of them showed considerable inhibitory activity against at least one of these two key enzymes of the arachidonic acid metabolism, especially against COX-1. The best results in inhibiting the formation of leukotrienes were obtained with the extract of Piper kadsura. In the terms of prostaglandin synthesis inhibition, the extract of Piper boehmeriifolium var. tonkinense was found to have the strongest activity. Furthermore, an analytical investigation by means of TLC, HPLC-DAD and GC-MS resulted in the identification of 20 constituents. Most of them were amides with an interesting variety of amine moieties. Among them were pellitorine, and four higher homologues, piperlonguminine, dihydropiperlonguminine, futoamide, chingchengenamide, the retrofractamides A, B and D, guineensine, brachystamide B, piperanine, piperine, piperdardine, sarmentine, pipataline and benzylbenzoate. In 96 cases, these constituents were new for the particular plant.

147 citations


Journal ArticleDOI
Virinder S. Parmar1, Subhash C. Jain1, Sangita Gupta1, S. Talwar1  +13 moreInstitutions (3)
Abstract: Thirty eight compounds of different types have been isolated from twelve Piper species. The ether extract of the leaves of P. aduncum yielded eleven compounds, out of which 2,6-dimethoxy-4-(2-propenyl)phenol was isolated for the first time from the genus Piper and 2-acetoxy-1,3-dimethoxy-5-(2-propenyl)benzene is a new compound. The petrol extract of the stems and leaves of P. attenuatum furnished a novel long chain alcohol, 14-benzo 1 , 3 dioxol-5-yl-tetradecan-2-ol. From P. betle, β-sitosteryl palmitate was isolated for the first time from the genus Piper. A novel amide, 3-(3,4-dimethoxyphenyl)propanoyl pyrrole has been obtained from P. brachystachyum. Nerolidol was isolated for the first time from P. falconeri. From the methanol extract of the stems and leaves of P. khasiana, piperlonguminine, piperine, apigenin dimethyl ether and β-sitosterol were obtained. Retrofractamide A was obtained for the first time from P. longum; the structure of (+)-asarinin, isolated from P. longum, was confirmed by X-ray crystallographic studies. Retrofractamide A, apigenin dimethyl ether, tetratriacontanol and tectochrysin were isolated from P. manii. P. pedicellosum furnished β-sitosterol, pellitorine, piperlonguminine, cepharadione A and furacridone, the last compound being isolated for the first time from the genus Piper.

126 citations


References
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Journal ArticleDOI
Asima Chatterjee1, C.P. Dutta1Institutions (1)
TL;DR: Piperlongumine and piperlonguminine are shown to be N-(3,4,5-trimethoxycinnamoyl)-Δ5-piperidin-2-one and isobutylamide of piperic acid respectively.
Abstract: From the root of Piper longum L two new alkaloids, piperlongumine and piperlonguminine have been isolated Piperlongumine and piperlonguminine are shown to be N-(3,4,5-trimethoxycinnamoyl)-Δ 5 -piperidin-2-one and isobutylamide of piperic acid respectively

95 citations


Journal ArticleDOI
Amerandra Patra1, Arundhati Ghosh1Institutions (1)

25 citations