What are Terpenoids?

Terpenoids or sometimes referred as isoprenoids are types of phytochemicals found in all classes of living things and are mainly of plant origin. Unlike terpenes, they have different chemical composition usually modified by oxidation and\or additional functional group or oxygen functionality that is responsible for different and characteristic chemical reaction. (1) Functional group is not the only thing that makes them different from one another. Some of them have different carbon skeleton. They are one of the largest groups of natural products and represent largest and most diverse class of chemicals. (2) Most of them are liquid type, with exception of few, without the colour and lighter than water. This makes them easily oxidized, insoluble in water but soluble in organic solvents. According to the Richard Firn, from the book called “Nature’s Chemicals”, they make up for about 60% of all known substances produced by living organisms. We have described and recognized more than 40,000 different terpenoids, with new types being discovered.

J.D. Connolly and R.A. Hill have written a “Dictionary of terpenoids” where they have described and arranged around 22 000 different types of terpenoids. The list is still not completely comprehensive because of the size and diversity of the group. You can find first publication here

Almost all organisms produce some of terpenoids as by-product of primary metabolism; while majority is produced with secondary one. (3) Plants utilize terpenoids for growth and development, but aside from this function they are responsible for far more specialised chemical interactions and protection than previously thought; both in abiotic and biotic environment. Terpenoids that come from plants have long history traditional usage, from food and pharmaceutics to chemical and fuel industry. Most commonly used because of their aromatic qualities they are main reason for distinctive smell of mint, flavour of garlic and strawberry as well as colours of tomato and sunflower. (4) With the development of metabolic engineering we have high-value terpenoids products created inside microbes and plants, all of this has been made possible by synthetic biology. (5)

They are most known for being main ingredient in almost all essential oils contributing to their scents; flowery, fruity, woody, balsamic. This has attracted interest of flavour and fragrance industry with most demand being in production and extraction for food industry. (6) Today, terpenoids in combination with other aromatic compounds are widely used in areas of aroma, tobacco, food, drink, flavour, fragrance and essential oils industry.

Some of the most common ones are:

Citral or Lemonal – Aroma compound most present in oils of lemon myrtle (90–98%), Litsea citrata (90%), Litsea cubeba (70–85%), lemongrass (65–85%), lemon tea-tree (70–80%), Ocimum gratissimum (66.5%), Lindera citriodora (about 65%), Calypranthes parriculata (about 62%), petitgrain (36%), lemon verbena (30–35%), lemon ironbark (26%), lemon balm (11%). Contrary to popular beliefs, lime and lemon have only 6-9% and 2-5% respectively. (7)

Menthol - Obtained from the oils of plants in the family Lamiaceae (mint family), usually field mint or peppermint. Interestingly, its biosynthesis begins with the synthesis of terpene limonene. (8)

Limonene – Named after the peel of lemon, one of the major components in oil of oranges and citrus peel, widely used as flavour and fragrance, used in chemical synthesis of another terpenoid, carvone. (9)

Carvone – Found in the seeds of caraway (cumin), spearmint and dill, used in food and flavour industry. (10)

Camphor – Transparent and solid terpenoid obtained from camphor tree, better known as cinnamon. It is also found in rosemary leaves in concentrations around 10% climbing even up to 20%. (11)

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References:

1. IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. https://doi.org/10.1351/goldbook
2. Tholl D, Biosynthesis and biological functions of terpenoids in plants, Adv Biochem Eng Biotechnol. 2015;148:63-106. doi: 10.1007/10_2014_295.
3. PPAR Research; Volume 2010, Article ID 483958, 9 pages
4. https://www.newyorker.com/magazine/2009/09/28/a-life-of-its-own
5. Tholl D, Biosynthesis and biological functions of terpenoids in plants, Adv Biochem Eng Biotechnol. 2015;148:63-106. doi: 10.1007/10_2014_295.
6. Caputi L, Aprea E; Use of terpenoids as natural flavouring compounds in food industry; Recent Pat Food Nutr Agric. 2011 Jan;3(1):9-16.
7. Fenaroli, G., Furia, T.E., Bellanca, N., Handbook of Flavor Ingredients, ISBN 0-87819-532-7;
   Lawless, J., The Illustrated Encyclopedia of Essential Oils, ISBN 1-85230-661-0
8. Croteau, R. B.; Davis, E. M.; Ringer, K. L.; Wildung, M. R. (December 2005). "(−)-Menthol biosynthesis and molecular genetics". Naturwissenschaften. 92 (12): 562–577. Bibcode:2005NW.....92..562C. doi:10.1007/s00114-005-0055-0. PMID 16292524.
9. D-Limonene". PubChem Compound Database. National Center for Biotechnology Information, US National Library of Medicine. 2017. Retrieved 22 December 2017.
10. “D-Limonene". PubChem Compound Database. National Center for Biotechnology Information, US National Library of Medicine. 2017. Retrieved 22 December 2017.
11. https://www.drugs.com/npp/rosemary.html

Read more from “Scrutiny of Knowledge Series:

➺ Introduction➺ Medicinal Cannabis in Cancer patients-➺ Antiquity of Entheogens and reasoning on superstitions regarding them➺ Biosynthesis of cannabinoids in yeast ➺What are Terpenoids

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