Revised structure and synthesis of piperolein acids, guineensine and wisanine from Piper guineense

Okwute, Simon Koma; Okogun, Joseph I.; Okorie, Dominic A.

doi:10.1016/s0040-4020(01)83507-9

Cited by 15 publications

(3 citation statements)

References 13 publications

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“…The insecticide activities of P. guineense has been attributed to piperine and piperic acid acting in synergism with some other compounds (Su, 1977). Miyakado (1979), also identified pipericide as being responsible for the insecticidal activity, while Okwute (1978), identified guineensine as the active ingredient.…”

Section: Resultsmentioning

confidence: 99%

Toxicity of Hexanolic Extracts of Piper guineese Schum and Thonn seed oil to larvae of Aedes aegypti (L.)

ANYAELE,

AMUSAN,

OKORIE

et al. 2002

NJE

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Hexanolic extract of Piper guineense Schum and Thonn (Piperaceae) was tested for acute toxicity on third instar larvae of Aedes aegypti reared in the Advanced Entomology Laboratory of the University of Ibadan, Nigeria. Five graded concentrations 0.9ppm, 1.7ppm, 2.5ppm, 3.3ppm and 4.1ppm, were tested on the larvae. Effects of two physical parameters namely; sunlight and ultra-violet radiation on the potency of the extract was also investigated. The extract showed a high level of toxicity on the 3rd instar larvae of A. aegypti. LC50 of P. guineense on the larvae was 1.7 ± 0.84ppm. The highest concentration of 4.1ppm killed 77% of the population within an hour and 95% in 24 hours while at the least concentration of 0.9ppm no death was recorded but killed 16% of the larvae in 24 hours. The potency of P. guineense on the larvae was drastically reduced when exposed to sunlight However, there was no significant difference between the potency of the U-V exposed extract the untreated, rather the raw data showed some level of activation by ultraviolet radiation.

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Section: Resultsmentioning

confidence: 99%

Toxicity of Hexanolic Extracts of Piper guineese Schum and Thonn seed oil to larvae of Aedes aegypti (L.)

ANYAELE,

AMUSAN,

OKORIE

et al. 2002

NJE

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“…The Wittig reaction product was purified by column chromatography on silica gel and re-crystallisation from methanol. Hydrolysis of the Wittig product with KOH in methanol gave the acid which on treatment with SOCl 2, and then isobutylamine/pyridine, gave the piper amide, guineensine (Figure 9) (Okwute, 1978;Okwute, Okogun, & Okorie, 1984). …”

Section: Total Synthesis Of Guineensinementioning

confidence: 99%

Piperine-Type Amides: Review of the Chemical and Biological Characteristics

Okwute¹,

Egharevba²

2013

IJC

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A new group of alkaloids emerged in 1819 following the isolation of piperine from the fruits of Piper nigrum. Since then, a large number of these compounds now referred to as piperine-type alkaloids or alkamides or piperamides have been isolated commonly from species belonging to the genus piper (piperaceae) which have worldwide geographical distribution. As a result of the traditional uses of piper species as spices in foods and in phytomedicines globally a number of their extractives and indeed the constituent amides have been screened for pharmacological properties. The biogenesis of the amides has been investigated and a number of synthetic pathways have been developed to make them readily available for biological studies. It has now been established that piperine and its analogues are potential pesticides and possess a number of medicinal properties. They are regarded as universal enhancers in pesticide and drug formulations. This review enhances our knowledge of these amides and paves way for further work.

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“…A review of the synthesis of 2,6-disubstituted piperidines includes a section on alkaloids of this type. A new piperidide (18) has been found in the underground parts of Achiffea figusticu,6 and has been formulated on spectroscopic evidence. An investigation into the human metabolism of pepper alkaloids has revealed that piperine is transformed into 5-(3,4-dihydroxypheny1)valeric acid piperidide (19) and its 4'hydroxy-derivative (20) by most subjects, but about 15% of the population produce 5-(3,4-dihydroxyphenyl)penta-2,4-dienoic acid piperidide (21).17 It has been established that wisanine (22) is a trans,trans-diene.I* The fruits of Piper fongum L. contain two new piperidides, ( 23) and ( 24), named piperonaline and piperundecalidine respectively.…”

Section: Piperidine Alkaloidsmentioning

confidence: 99%

Pyrrlidine, piperidine, and pyridine alkaloids

Pinder¹

1985

Nat. Prod. Rep.

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Revised structure and synthesis of piperolein acids, guineensine and wisanine from Piper guineense

Cited by 15 publications

References 13 publications

Toxicity of Hexanolic Extracts of Piper guineese Schum and Thonn seed oil to larvae of Aedes aegypti (L.)

Toxicity of Hexanolic Extracts of Piper guineese Schum and Thonn seed oil to larvae of Aedes aegypti (L.)

Piperine-Type Amides: Review of the Chemical and Biological Characteristics

Pyrrlidine, piperidine, and pyridine alkaloids

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