• Terpenoids
    Extraction
    And Analysis

Background

Terpenoids, also known as isoprenoids, are a large and diverse class of naturally occurring organic chemicals derived from five-carbon isoprene units assembled in a variety of ways. Most are multicyclic structures with oxygen-containing functional groups. They constitute one of the largest families of plant metabolites and are found in all classes of living things.

Terpenoids play several crucial roles in plants. They are involved in growth and development, and are important for plants' interactions with their environment, such as attracting pollinators, deterring herbivores, and protecting against pathogens.

From a structural perspective, terpenoids are grouped according to the number of isoprene units in the molecule. The different groups are listed below:

  • Monoterpenoids (C10, 2 isoprene units)
  • Sesquiterpenoids (C15, 3 isoprene units)
  • Diterpenoids (C20, 4 isoprene units)
  • Sesterterpenoids (C25, 5 isoprene units)
  • Triterpenoids (C30, 6 isoprene units)
  • Tetraterpenoids (C40, 8 isoprene units)
  • Polyterpenoids (larger structures, many isoprene units)



Many terpenoids have significant bioactive properties, making them of interest in medicine, nutrition, and other fields of research. Some terpenoids have been used for centuries in traditional medicine, while others are important ingredients in perfumes and cosmetics due to their aromatic properties. Some examples are provided below:
  • Monoterpenoids like menthol (from peppermint) and limonene (from citrus fruits) are often used in cosmetics and food products for their fragrant properties.
  • Sesquiterpenes like artemisinin (from the sweet wormwood plant) are used as antimalarial drugs.
  • Diterpenes include compounds like taxol (from the Pacific yew tree), which is used in cancer therapy.
  • Triterpenoids include saponins, which have a range of bioactive properties and are often found in traditional medicines, and steroids, which have roles in many biological processes in animals.
  • Carotenoids are tetraterpenoids that have key roles in plant pigmentation and contribute to the health benefits of many fruits and vegetables.


Terpenoids in Different Types of Biomass

Bark

Examples of some common terpenoids found in bark are provided below:
  • Pinene - A monoterpene commonly found in the bark of pine trees that has a distinctive pine-like aroma. There are two structural isomers of pinene found in nature: alpha-pinene and beta-pinene, with alpha-pinene being more prevalent.
  • Cedrol - A sesquiterpene alcohol found in the bark of cedar trees. It has a distinctive woody, cedar-like aroma and is used in the perfume industry.
  • Camphor - A bicyclic monoterpene found in the bark of the camphor tree. It has a strong, minty aroma and a cooling sensation. Camphor is used in medicinal products such as ointments and inhalants.
  • Taxol - A diterpene found in the bark of the Pacific Yew tree. It has been found to inhibit the growth of cancer cells and is used as a chemotherapy drug.
  • Limonene - This is a monoterpene that is found in the bark of citrus trees. Limonene has a strong, citrusy aroma and is used in a wide range of products from cleaning agents to cosmetics.
  • Betulin and Betulinic Acid - These are triterpenoids found in the bark of the white birch tree. Both compounds have been studied for their potential anti-inflammatory and anti-cancer properties. Click here to read about Celignis's work with the extraction and purification of betulin.

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Roots

Examples of some common terpenoids found in roots are provided below:
  • Artemisinin - This sesquiterpenoid is found in the roots and leaves of the sweet wormwood plant (Artemisia annua). It is a powerful antimalarial compound and is used in the production of some of the most effective antimalarial drugs currently available.
  • Ginsenosides - These are a class of steroid glycosides, and triterpenoid saponins, found in the roots of the ginseng plant. They have been studied for a wide range of potential health benefits, including anti-inflammatory, anticancer, and immune-modulating effects.
  • Astragalosides - These triterpenoid saponins are found in the roots of the Astragalus plant. They have been studied for their potential immune-boosting and heart-protective effects.
  • Withanolides - These are a group of steroidal lactones which constitute a major part of the ashwagandha root (Withania somnifera). They are known for their adaptogenic properties, helping the body resist physical and chemical stresses.
  • Furanocoumarins - Found in the roots of many citrus plants, these terpenoid derivatives have been studied for their potential antiviral and anticancer properties.
  • Paclitaxel (Taxol) - This complex diterpenoid is originally derived from the bark, but it is now more commonly synthesized from the precursors found in the roots of the yew tree. It is a powerful anti-cancer drug used in the treatment of a variety of cancers.

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Fruit and Vegetables

Examples of some terpenoids, other than carotenoids, found in fruits and vegetables are listed below:
  • Limonene - This monoterpene is abundant in the peel of citrus fruits (e.g. oranges, lemons, limes, and grapefruits) and is responsible for their characteristic citrusy aroma.
  • Thymol - Thyme contains thymol, a monoterpene with antimicrobial properties.
  • Capsaicin - This terpenoid is the compound responsible for the spiciness of chili peppers.
  • Mangiferin - This potent antioxidant is found in the peel, and leaves of mango.
  • Alpha-farnesene - One of the many terpenoids found in apples that contribute to their aroma.
  • Humulene and Myrcene - These are two terpenoids, among others, that are found in hops that contribute to the flavour of beer.
  • Allicin - This is one of the sulphur-containing terpenoids in garlic that contributes to its strong aroma and flavour.
  • Linalool - A terpenoid found in pineapple that contributes to its unique aroma, with pinene being another example.

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Seeds

Examples of some terpenoids found in seeds are provided:
  • Carotenoids - This terpenoid provides the yellow, orange, and red colors found in many plants. Carotenoids are found in the seeds of many plants, including corn and tomatoes.
  • Ginkgolides - Found in the seeds of Ginkgo biloba and have been studied for their potential medicinal properties, including as anti-asthmatic and anti-allergic agents.
  • Artemisinin - This is a sesquiterpene lactone (a type of terpenoid) found in the seeds and leaves of Artemisia annua (sweet wormwood). It is used as an anti-malarial drug.
  • Sesquiterpene lactones - Found in many plant seeds, sesquiterpene lactones are known to have anti-inflammatory and anti-microbial effects. Some seeds of the Asteraceae family, such as sunflower seeds, contain these terpenoids.
  • Monoterpenes - Certain seeds, such as fennel and dill, contain monoterpenes like limonene and carvone, which give these seeds their characteristic aromas.
  • Saponins - Saponins, which are glycosylated terpenoids, are found in a variety of seeds including quinoa and fenugreek.


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Extraction of Terpenoids from Biomass


The extraction process, including the solvents and methods used, can influence the concentration and types of terpenoids present in the final extract. It is often the case that a balance needs to be found between fully-extracting all terpenoids while also ensuring that the compounds that are obtained are of a high quality and not degraded.

At Celignis we have extensive experience in the design and optimisation of extraction protocols for a wide variety of chemical constituents from many different biomass types. If needed we can also work on processes to separate and purify the target compounds.

Click here to read more about Celignis's Bioprocess Development Services for the extraction of chemicals from biomass.

Get more info...Biomass Extractions




Analysis of Terpenoids at Celignis

We have the necessary equipment and expertise to determine the amount and distribution of terpenoids in a wide variety of biomass samples.

Feel free to get in touch with us to request further information and a quotation.

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