Terpenoids

Terpenoids List

Introduction

Terpenoids, also known as isoprenoids, are a large class of natural compounds with medicinal potencies, mainly derived from plants, marine phytoplankton, mushrooms, algae and some fungi. Terpenoids share a simple unifying feature known as the isoprene rule (Fig. 1). Many terpenoids have significant pharmacological and biological activities, such as anticancer, antioxidant, anti-inflammatory, antimicrobial, and antiviral activities, making them valuable for research and application in various fields.

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Fig. 1 Structure of isoprene, the basic unit of a terpenoid.

Classification of Terpenoids

Terpenoids are diverse and can be classified in two ways, including by the type and number of rings contained in molecules, and the number of isoprene units in their backbone, mainly focus on the latter classification method.

• According to the type and number of cyclic structures they contain, terpenoids can be classified as linear, acyclic, monocyclic, bicyclic, tricyclic, tetracyclic, pentacyclic, and macrocyclic.
• According to the number of isoprene units in their skeleton, terpenoids can be divided into hemiterpenes, monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, and tetraterpenes/carotenoids. The number of isoprene units, number of carbon atoms and molecular formula of different types of terpenoids are listed in the table below.

Table. 1. Terpenoids and their number of isoprene units, number of carbon atoms, and general formula.

Applications

Terpenoids, with their diverse chemical structures and potent biological activities, find applications across numerous industries. Here are some applications of terpenoids in different industries.

• In the pharmaceutical industry, with their demonstrated anticancer, antimicrobial, anti-inflammatory, and antiviral properties, terpenoids are increasingly becoming focal points in modern pharmaceutical research. For instance, artemisinin, sourced from the Artemisia annua plant, stands as a prime example, finding extensive use in the treatment of malaria. Similarly, paclitaxel (Taxol), a renowned diterpenoid alkaloid extracted from the Pacific yew tree, holds significant promise in cancer chemotherapy.
• In the fragrance and flavor industry, terpenoids serve as important components in perfumes, and cosmetics. Their volatile nature and wide array of scents, ranging from floral to citrusy, make them indispensable ingredients in fragrance formulations. For example, limonene, a cyclic monoterpene abundant in citrus fruits, finds application in household cleaners and cosmetics for its refreshing fragrance. Similarly, linalool, present in lavender and various flowers, stands out as a quintessential terpenoid fragrance, enriching perfumes, soaps, and lotions with its floral notes.
• In the agriculture industry, terpenoids also find significant traction owing to their insecticidal and repellent properties. For example, pyrethrins, derived from chrysanthemum flowers, are extensively utilized in organic farming for their effectiveness against pests. Additionally, neem oil, enriched with terpenoids like azadirachtin, emerges as a natural and sustainable insecticide, derived from the neem tree.

Biosynthesis of Terpenoids

All terpenoids are formed from repeating units of 5-carbon building blocks called isoprene. Its biosynthetic pathway starts with the primary metabolite acetyl-CoA and undergoes a series of reactions to form mevalonate. Then mevalonate synthesizes the basic 5-carbon building blocks, isopentenyl diphosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), and then through a series of reactions, it can synthesize monoterpenes, sesquiterpenes, and diterpenes, triterpenes and tetraterpenes (Fig. 2).

• Formation of Monoterpenes: DMAPP and IPP combine in a head-to-tail manner to yield geranyl diphosphate (GPP), a 10-carbon skeleton and the immediate precursor of monoterpenes.
• Formation of Sesquiterpenes: GPP serves as the substrate for the addition of an extra 5-carbon unit, resulting in the formation of farnesyl pyrophosphate (FPP), the precursor of sesquiterpenes with a 15-carbon structure.
• Formation of Diterpenes: FPP is further elongated through the addition of another 5-carbon unit, generating geranylgeranyl diphosphate (GGPP), which acts as the precursor for diterpenes comprising 20 carbons.
• Formation of Triterpenes and Tetraterpenes: Dimerization of FPP and GGPP leads to the synthesis of triterpenes (30 carbons) and tetraterpenes (40 carbons), respectively, via head-to-head addition.

Fig. 2. An overview of terpenoids biosynthesis ^[1].

Alfa Chemistry offers a wide range of terpenes, encompassing monoterpenes, sesquiterpenes, diterpenes, and more. For a comprehensive view of our product catalog, kindly access the link provided at the top of this page. If you do not find the product you need, please do not hesitate to contact us. We can also customize the synthesis according to customers' requirements.

Reference:

1. Habtemariam, S. Chapter 6-Introduction to plant secondary metabolites—From biosynthesis to chemistry and antidiabetic action. Medicinal Foods as Potential Therapies for Type-2 Diabetes and Associated Diseases. 2019, 109–132