Here is a list of the different capcaisinoids and some info from Wikipedia. I am a PhD biochemist with 6 years of post-doctoral training and spent 15 years in Academia, so ask me questions and I`ll try to find it out and explain it as best I can. One thing I can`t find is how each different member of the vanilloid (capsaicin) family acts to give different sensations when you eat them.
Capsaicin is the main capsaicinoid in chili peppers, followed by
dihydrocapsaicin. These two compounds are also about twice as potent to the taste and nerves as the minor capsaicinoids
nordihydrocapsaicin,
homodihydrocapsaicin, and
homocapsaicin. Dilute solutions of pure capsaicinoids produced different types of pungency; however, these differences were not noted using more concentrated solutions.
Capsaicin is believed to be synthesized in the
interlocular septum of chili peppers by addition of a branched-chain
fatty acid to
vanillylamine; specifically, capsaicin is made from vanillylamine and 8-methyl-6-nonenoyl CoA.[sup]
[16][/sup][sup]
[17][/sup] Biosynthesis depends on the gene
AT3, which resides at the
pun1 locus, and which encodes a putative
acyltransferase.[sup]
[18][/sup]
Besides the six natural capsaicinoids, one synthetic member of the capsaicinoid family exists.
Vanillylamide of n-nonanoic acid (VNA, also PAVA) is used as a reference substance for determining the relative pungency of capsaicinoids.
I`ve put the 3 references indicated as 16, 17 and 18 below the table.
Capsaicinoid name Abbrev. Typical
relative
amount
Scoville
heat units Chemical structure Capsaicin C 69% 16,000,000
Dihydrocapsaicin DHC 22% 15,000,000
Nordihydrocapsaicin NDHC 7% 9,100,000
Homodihydrocapsaicin HDHC 1% 8,600,000
Homocapsaicin HC 1% 8,600,000
Nonivamide PAVA 9,200,000
The burning and painful sensations associated with capsaicin result from its chemical interaction with sensory
neurons. Capsaicin, as a member of the
vanilloid family, binds to a
receptorcalled the
vanilloid receptor subtype 1 (VR1).[sup]
[46][/sup] First cloned in 1997, VR1 is an
ion channel-type receptor. VR1, which can also be stimulated with heat and physical abrasion, permits
cationsto pass through the
cell membrane and into the cell when activated. The resulting
depolarization of the neuron stimulates it to
signal the brain. By binding to the VR1 receptor, the capsaicin molecule produces similar sensations to those of excessive heat or abrasive damage, explaining why the spiciness of capsaicin is described as a burning sensation.
Early research showed capsaicin to evoke a strikingly long-onset current in comparison to other chemical agonists, suggesting the involvement of a significant rate-limiting factor.[sup]
[47][/sup]Subsequently, the VR1
ion channel has been shown to be a member of the superfamily of
TRP ion channels, and as such is now referred to as
TRPV1. There are a number of different
TRP ion channels that have been shown to be sensitive to different ranges of temperature and probably are responsible for our range of temperature sensation. Thus, capsaicin does not actually cause a
chemical burn, or indeed any direct tissue damage at all, when chili peppers are the source of exposure. The inflammation resulting from exposure to capsaicin is believed to be the result of the body's reaction to nerve excitement. For example, the mode of action of capsaicin in inducing bronchoconstriction is thought to involve stimulation of C fibres [sup]
[48][/sup]culminating in the release of neuropeptides. Essentially, the body inflames tissues as if it has undergone a burn or abrasion and the resulting inflammation can cause tissue damage in cases of extreme exposure, as is the case for many substances that cause the body to trigger an inflammatory response.
- 16.^ Fujiwake H., Suzuki T., Oka S., Iwai K. (1980). "Enzymatic formation of capsaicinoid from vanillylamine and iso-type fatty acids by cell-free extracts of Capsicum annuum var. annuum cv. Karayatsubusa". Agricultural and Biological Chemistry 44: 2907–2912.
- 17.^ I. Guzman, P.W. Bosland, and M.A. O'Connell, "Chapter 8: Heat, Color, and Flavor Compounds in Capsicum Fruit" in David R. Gang, ed., Recent Advances in Phytochemistry 41: The Biological Activity of Phytochemicals (New York, New York: Springer, 2011), pages 117-118.
- 18.^ Stewart C, Kang BC, Liu K, et al. (June 2005). "The Pun1 gene for pungency in pepper encodes a putative acyltransferase". Plant J. 42 (5): 675–88. doi:10.1111/j.1365-313X.2005.02410.x. PMID 15918882.
- 46.^ Story GM, Crus-Orengo L (July–August 2007). "Feel the burn". American Scientist 95 (4): 326–333. doi:10.1511/2007.66.326.
- 47.^ Geppetti, Pierangelo & Holzer, Peter (1996). Neurogenic Inflammation. CRC Press, 1996.
- 48.^ Fuller, R. W., Dixon, C. M. S. & Barnes, P. J. (1985). Bronchoconstrictor response to inhaled capsaicin in humans. J. Appl. Physiol., 58, 1080–1084. PubMed, CAS, Web of Science® Times Cited: 174