4224 J. Agric. Food Chem., Vol. 56, No. 11, 2008
Thiele et al.
ACKNOWLEDGMENT
(16) Kirschbaum-Titze, P.; Mueller-Seitz, E.; Petz, M. Pungency in
paprika (Capsicum annuum). 2. Heterogeneity of capsaicinoid
content in individual fruits from one plant. J. Agric. Food Chem.
2002, 50, 1264–1266.
We thank H. Guth for valuable advice during interpretation
of the mass spectral results.
(17) Ben-Chaim, A.; Borovsky, Y.; Falise, M.; Mazourek, M.; Kang,
B. C.; Paran, I.; Jahn, M. QTL analysis for capsaicinoid content
in Capsicum. Theor. Appl. Genet. 2006, 113, 1481–1490.
(18) Stewart, C.; Mazourek, M.; Stellari, G. M.; O’Connell, M.; Jahn,
M. Genetic control of pungency in C. chinense via the Pun1 locus.
J. Exp. Bot. 2007, 58, 979–991.
(19) Sukrasno, N.; Yeoman, M. M. Phenylpropanoid metabolism during
growth and development of Capsicum frutescens fruits. Phy-
tochemistry 1993, 32, 839–844.
(20) Prasad, N. B. C.; Gururaj, H. B.; Kumar, V.; Giridhar, P.;
Parimalan, R.; Sharma, A.; Ravishankar, G. A. Influence of
8-methyl-nonenoic acid on capsaicin biosynthesis in in ViVo and
in Vitro cell cultures of Capsicum spp. J. Agric. Food Chem. 2006,
54, 1854–1859.
(21) Yao, J.; Nair, M. G.; Chandra, A. Supercritical carbon dioxide
extraction of Scotch Bonnet (Capsicum annuum) and quantifica-
tion of capsaicin and dihydrocapsaicin. J. Agric. Food Chem. 1994,
42, 1303–1305.
(22) Peusch, M.; Mueller-Seitz, E.; Petz, M.; Mueller, A.; Anklam, E.
Extraction of capsaicinoids from chillies (Capsicum frutescens
L.) and paprika (Capsicum annuum L.) using supercritical fluids
and organic solvents. Z. Lebensm. Unters. Forsch. A 1997, 204,
351–355.
(23) Prasad, N.B. C.; Gururaj, H. B.; Kumar, V.; Giridhar, P.;
Ravishankar, G. A. Valine pathway is more crucial than phenyl
propanoid pathway in regulating capsaicin biosynthesis in Cap-
sicum frutescens Mill. J. Agric. Food Chem. 2006, 54, 6660–
6666.
(24) Post-Beittenmiller, D.; Jaworski, J. G.; Ohlrogge, J. B. In ViVo
pools of free and acylated acyl carrier proteins in spinach.
Evidence for sites of regulation of fatty acid biosynthesis. J. Biol.
Chem. 1991, 266, 1858–1865.
(25) Kopka, J.; Ohlrogge, J. B.; Jaworski, J. G. Analysis of in ViVo
levels of acyl-thioesters with gas chromatography/mass spectrom-
etry of the butylamide derivative. Anal. Biochem. 1995, 224, 51–
60.
LITERATURE CITED
(1) Perry, L.; Dickau, R.; Zarrillo, S.; Holst, I.; Pearsall, D. M.;
Piperno, D. R.; Berman, M. J.; Cooke, R. G.; Rademaker, K.;
Ranere, A. J.; Raymond, J. S.; Sandweiss, D. H.; Scaramelli, F.;
Tarble, K.; Zeidler, J. A. Starch fossils and the domestication and
dispersal of chili peppers (Capsicum spp. L.) in the Americas.
Science 2007, 315, 986–988.
(2) Suzuki, T.; Iwai, K. Constituents of red pepper species: chemistry,
biochemistry, pharmacology, and food science of the pungent
principle of Capsicum species. In The Alkaloids: Chemistry and
Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL,
1984; Vol. 23, pp 227-299.
(3) Kroumova, A. B.; Wagner, G. J. Different elongation pathways
in the biosynthesis of acyl groups of trichome exudate sugar esters
from various solanaceous plants. Planta 2003, 216, 1013–1021.
(4) Tominaga, M. Molecular mechanisms of trigeminal nociception
and sensation of pungency. Chem. Senses 2005, 30 (Suppl. 1),
i191–i192.
(5) Jordt, S. E.; McKemy, D. D.; Julius, D. Lessons from peppers
and peppermint: the molecular logic of thermosensation. Curr.
Opin. Neurobiol. 2003, 13, 487–492.
(6) Cortright, D. N.; Szallasi, A. Biochemical pharmacology of the
vanilloid receptor TRPV1. An update. Eur. J. Biochem. 2004, 271,
1814–1819.
(7) Markai, S.; Marchand, P. A.; Mabon, F.; Baguet, E.; Billault, I.;
Robins, R. J. Natural deuterium distribution in branched-chain
medium-length fatty acids is nonstatistical: a site-specific study
by quantitative 2H NMR spectroscopy of the fatty acids of
capsaicinoids. ChemBioChem 2002, 3, 212–218.
(8) Curry, J.; Aluru, M.; Mendoza, M.; Nevarez, J.; Melendrez, M.;
O’Connell, M. A. Transcripts for possible capsaicinoid biosyn-
thetic genes are differentially accumulated in pungent and non-
pungent Capsicum spp. Plant Sci. 1999, 148, 47–57.
(9) Aluru, M. R.; Mazourek, M.; Landry, L. G.; Curry, J.; Jahn, M.;
O’Connell, M. A. Differential expression of fatty acid synthase
genes, Acl, Fat and Kas, in Capsicum fruit. J. Exp. Bot. 2003,
54, 1655–1664.
(26) Kirschbaum-Titze, P.; Hiepler, C.; Mueller-Seitz, E.; Petz, M.
Pungency in paprika (Capsicum annuum). 1. Decrease of capsai-
cinoid content following cellular disruption. J. Agric. Food Chem.
2002, 50, 1260–1263.
(27) Deutsches Institut fuer Normung, Chemical analysis; decision
limit; detection limit and determination limit; estimation in case
of repeatability; terms, methods, evaluation. In DIN 32645; Beuth:
Berlin, Germany, 1994.
(10) Fujiwake, H.; Suzuki, T.; Oka, S.; Iwai, K. Enzymatic formation
of capsaicinoid from vanillylamine and iso-type fatty acids by
cell-free extracts of Capsicum annuum var. annuum cv. Karayat-
subusa. Agric. Biol. Chem. 1980, 44, 2907–2912.
(11) Prasad, N. B. C.; Kumar, V.; Gururaj, H. B.; Parimalan, R.;
Giridhar, P.; Ravishankar, G. A. Characterization of capsaicin
synthase and identification of its gene (csy1) for pungency factor
capsaicin in pepper (Capsicum sp.). Proc. Natl. Acad. Sci. U.S.A.
2006, 103, 13315–13320.
(12) Schuett, B. S.; Brummel, M.; Schuch, R.; Spener, F. The role of
acyl carrier protein isoforms from Cuphea lanceolata seeds in
the de-novo biosynthesis of medium-chain fatty acids. Planta
1998, 205, 263–268.
(13) Kopp, B.; Jurenitsch, J. Biosynthesis of Capsicum annuum L. var
annuum. III Problem of the formation of capsaicin and dihydro-
capsaicin. Sci. Pharm. 1982, 50, 150–157.
(14) Zewdie, Y.; Bosland, P. W. Evaluation of genotype, environment,
and genotype-by-environment interaction for capsaicinoids in
Capsicum annuum L. Euphytica 2000, 111, 185–190.
(15) Garcés-Claver, A.; Gil-Ortega, R.; Álvarez-Fernández, A.; Arnedo-
Andrés, M. S. Inheritance of capsaicin and dihydrocapsaicin,
determined by HPLC-ESI/MS, in an intraspecific cross of Cap-
sicum annuum L. J. Agric. Food Chem. 2007, 55, 6951–6957.
(28) Shanklin, J.; Cahoon, E. B. Desaturation and related modifications
of fatty acids. Annu. ReV. Plant Physiol. Plant Mol. Biol. 1998,
49, 611–641.
(29) Larson, T. R.; Graham, I. A. A novel technique for the sensitive
quantification of acyl CoA esters from plant tissues. Plant J. 2001,
25, 115–125.
(30) Villas-Bôas, S. G.; Mas, S.; Åkesson, M.; Smedsgaard, J.; Nielsen,
J. Mass spectrometry in metabolome analysis. Mass Spectrom.
ReV. 2005, 24, 613–646.
(31) Gao, L.; Chiou, W.; Tang, H.; Cheng, X.; Camp, H. S.; Burns,
D. J. Simultaneous quantification of malonyl-CoA and several
other short-chain acyl-CoAs in animal tissues by ion-pairing
reversed-phase HPLC/MS. J. Chromatogr., B 2007, 853, 303–
313.
Received for review November 22, 2007. Revised manuscript received
February 28, 2008. Accepted March 13, 2008.
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