Secondary metabolite

Secondary metabolites are organic compounds that are not directly involved in the normal growth, development,
or reproduction of an organism. Unlike primary metabolites, absence of secondary metabolites does not result in
immediate death, but rather in long-term impairment of the organism's survivability, fecundity, or aesthetics, or
perhaps in no significant change at all. Secondary metabolites are often restricted to a narrow set of species within a
phylogenetic group. Secondary metabolites often play an important role in plant defense against herbivory and other
interspecies defenses. Humans use secondary metabolites as medicines, flavorings, and recreational drugs.[1]

Secondary metabolites aid a plant in important functions such as protection, competition, and species interactions,
but are not necessary for survival. One important defining quality of secondary metabolites is their specificity.
Usually, secondary metabolites are specific to an individual species.[2] Research also shows that secondary metabolic
can affect different species in varying ways. In the same forest, four separate species of arboreal marsupial folivores
reacted differently to a secondary metabolite in eucalypts.[3] This shows that differing types of secondary metabolites
can be the split between two herbivore ecological niches.[3] Additionally, certain species evolve to resist plant
secondary metabolites and even use them for their own benefit. For example, monarch butterflies have evolved to be
able to eat milkweed (Asclepias) despite the toxic secondary metabolite it contains.[4] This ability additionally allows
the butterfly and caterpillar to be toxic to other predators due to the high concentration of secondary metabolites
consumed.[4]

Contents
1 Human health implications
2 Categories
2.1 Small "small molecules"
2.2 Big "small molecules", produced by large, modular, "molecular factories"
2.3 Non-"small molecules" - DNA, RNA, ribosome, or polysaccharide "classical" biopolymers
3 See also
4 References

Human health implications

Most polyphenol nutraceuticals from plant origin must undergo intestinal transformations, by microbiota and
enterocyte enzymes, in order to be absorbed at enterocyte and colonocyte levels. This gives rise to diverse beneficial
effects in the consumer, including a vast array of protective effects against viruses, bacteria, and protozoan
parasites.[5]

Secondary metabolites also have a strong impact on the food humans eat. Some researchers believe that certain
secondary metabolite volatiles are responsible for human food preferences that may be evolutionarily based in
nutritional food.[6] This area of interest has not been thoroughly researched, but has interesting implications for
human preference. Many secondary metabolites aid the plant in gaining essential nutrients, such as nitrogen. For
example, legumes use flavonoids to signal a symbiotic relationship with nitrogen fixing fungi (rhizobium) to increase
their nitrogen uptake.[4] Therefore, many plants that utilize secondary metabolites are high in nutrients and
advantageous for human consumption.

Categories
Most of the secondary metabolites of interest to humankind fit into categories which classify secondary metabolites
based on their biosynthetic origin. Since secondary metabolites are often created by modified primary metabolite
synthases, or "borrow" substrates of primary metabolite origin, these categories should not be interpreted as saying
that all molecules in the category are secondary metabolites (for example the steroid category), but rather that there
are secondary metabolites in these categories.

Small "small molecules"

Alkaloids (usually a small, heavily derivated amino acid):

Hyoscyamine, present in Datura stramonium

Atropine, present in Atropa belladonna, Deadly nightshade
Cocaine, present in Erythroxylum coca the Coca plant
Scopolamine, present in the Solanaceae (nightshade) plant family
Codeine and Morphine, present in Papaver somniferum, the opium poppy
Tetrodotoxin, a microbial product in Fugu and some salamanders
Vincristine & Vinblastine, mitotic inhibitors found in the Rosy Periwinkle
Terpenoids (come from semiterpene oligomerization):

Azadirachtin, (Neem tree)

Artemisinin, present in Artemisia annua Chinese wormwood
tetrahydrocannabinol, present in cannabis
Steroids (Terpenes with a particular ring structure)

Saponins (plant steroids, often glycosylated)

Flavonoids (or bioflavonoids) (from the Latin word flavus meaning yellow, their color in nature) are a class of
plant and fungus secondary metabolites):

isoflavanoids & neoflavanoids, flavone, flavanones

Glycosides (heavily modified sugar molecules):

Nojirimycin
Glucosinolates
Natural phenols:

Resveratrol
Phenazines:

Pyocyanin
Phenazine-1-carboxylic acid (and derivatives)
Biphenyls and dibenzofurans are phytoalexins of the Pyrinae[7]

Big "small molecules", produced by large, modular, "molecular factories"

Polyketides:

Erythromycin
 Lovastatin and other statins
Discodermolide
Aflatoxin B1
Avermectins
Nystatin
Rifamycin
Fatty acid synthase products :

FR-900848
U-106305
phloroglucinols
Nonribosomal peptides:

Vancomycin
Ramoplanin
Teicoplanin
Gramicidin
Bacitracin
Ciclosporin
Ribosomally synthesized and post-translationally modified peptides:

Thiostrepton
Hybrids of the above three:

Epothilone
Polyphenols

Non-"small molecules" - DNA, RNA, ribosome, or polysaccharide "classical"

biopolymers
Ribosomal peptides:

Microcin-J25

See also
Secondary metabolism
Hairy root culture, a strategy used in plant tissue culture to produce good quantities of valuable secondary
metabolites
Metabolite
Primary metabolite

References
1. "Secondary metabolites - Knowledge Encyclopedia" (http://www.biologyreference.com/knowledge/Secondary_me
tabolites.html). www.biologyreference.com. Retrieved 2016-05-10.
2. Pichersky, E. & Gang, D.R. (2000) Genetics and biochemistry of secondary metabolites in plants: an evolutionary
perspective. Trends in plant science, 5, 439-445.
3. Jensen, L.M., Wallis, I.R., Marsh, K.J., Moore, B.D., Wiggins, N.L., & Foley, W.J. (2014) Four species of arboreal
folivore show differential tolerance to a secondary metabolite. Oecologia, 176, 251-258.
4. Croteau, R., Kutchan, T. M., & Lewis, N. G. (2000). Natural products (secondary metabolites). Biochemistry and
molecular biology of plants, Ch. 24, 1250-1319.
 5. http://www.hindawi.com/journals/bmri/2015/905215/
6. Goff, S.A. & Klee, H.J. (2006) Plant volatile compounds: sensory cues for health and nutritional values? Science,
311, 815-819.
7. Chizzali, Cornelia & Beerhues, Ludger (2012). "Phytoalexins of the Pyrinae: Biphenyls and dibenzofurans".
Beilstein J. Org. Chem. 8: 613620. doi:10.3762/bjoc.8.68 (https://doi.org/10.3762%2Fbjoc.8.68).

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