Analysis of Piperaceae Germplasm by HPLC and LCMS:  A Method for Isolating and Identifying Unsaturated Amides from Piper spp Extracts

A method for extraction and high performance liquid chromatography−mass spectrometer (HPLC-MS) analysis of the medicinally important genus Piper (Piperaceae) was developed. This allows for a rapid and accurate measure of unsaturated amides, or piperamides, in black pepper, Piper nigrum L., and in wi...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2005-03, Vol.53 (6), p.1907-1913
Main Authors: Scott, Ian M, Puniani, Evaloni, Jensen, Helen, Livesey, John F, Poveda, Luis, Sánchez-Vindas, Pablo, Durst, Tony, Arnason, John T
Format: Article
Language:English
Subjects:
Aedes
Aedes atropalpus
Agronomy. Soil science and plant productions
Alkaloids - analysis
Alkaloids - isolation & purification
amides
Amides - analysis
Amides - isolation & purification
Animals
Benzodioxoles
bioassays
Biological and medical sciences
black pepper
botanical insecticides
Chemical constitution
Chromatography, High Pressure Liquid - methods
Culicidae
Economic plant physiology
Fundamental and applied biological sciences. Psychology
germplasm
high performance liquid chromatography
insecticidal properties
Insecticides
Larva
larvae
liquid chromatography
mass spectrometry
Mass Spectrometry - methods
pesticidal plants
Piper
Piper nigrum
Piperaceae - chemistry
Piperidines - analysis
Piperidines - isolation & purification
plant extracts
Plant Extracts - chemistry
plant genetic resources
Polyunsaturated Alkamides
wild relatives
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Summary:A method for extraction and high performance liquid chromatography−mass spectrometer (HPLC-MS) analysis of the medicinally important genus Piper (Piperaceae) was developed. This allows for a rapid and accurate measure of unsaturated amides, or piperamides, in black pepper, Piper nigrum L., and in wild species from Central America. Reflux extraction provided the highest recovery of piperine (>80%) from leaf and peppercorn material. HPLC analysis using a binary gradient of acetonitrile and water separated the major amide peaks between 5 and 12 min. Atmospheric pressure chemical ionization (APCI)-MS improved the detection limit to 0.2 ng, 10-fold below the 2 ng limit of the HPLC-diode array detector (DAD) based on linear standard curves between 0.1 and 250 μg/mL (R 2 = 0.999). The HPLC-MS method identified pellitorine, piperylin, 4,5-dihydropiperlonguminine, piperlonguminine, 4,5-dihydropiperine, piperine, and pipercide. The biological activity of six Costa Rican Piper species assessed by mosquito larval bioassays correlated well with piperamide content. Keywords: Piperaceae; Piper nigrum; piperamides; HPLC/MS
ISSN:0021-8561
1520-5118
DOI:10.1021/jf048305a