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The Classification of Sesquiterpene Compounds and Their Research Progress

The Classification of Sesquiterpene Compounds and Their Research Progress

by Xiaomichong

May 23, 2024

Terpenoids are an important part of natural organic compounds, and there are currently more than 50,000 reported terpenoid structures. Studies have found that some natural terpenoids have strong antitumor, anti-inflammatory and antibacterial activities, and these biologically active natural terpenoids include sesquiterpenes, diterpenoids, monoterpenoids, disesquiterpenoids and triterpenoids, among which sesquiterpenoids are the terpenoids with the largest number and structural skeleton types, and their structures contain one or more carbon atoms with double bonds or triple bonds carbon atoms, which can be divided into single-ring, double-ring, tripyclic and tetracyclic types according to the number of carbon rings. According to the number of carbon atoms constituting the ring, it can be divided into five-membered ring, six-membered ring and seven-membered ring sesquiterpene ring, and can also be divided into sesquiterpene alcohol, sesquiterpene ketone, sesquiterpene lactone, etc. according to different oxygen-containing groups.

Sesquiterpenes are widely found in plants, microorganisms, marine organisms and certain insects. The plants with the highest content of sesquiterpenes were birch and birch resin of the birch family, and the higher content of sesquiterpenes in traditional medicinal materials were Asteraceae in the genus Asteraceae, Atractylodes in the genus Asteraceae, and Mulchflower in the genus Asteraceae. mint in the genus Peppermint in the Lamiaceae family, Zeeland in the genus Shoots in the Lamiaceae family; Verbena in the genus Verbena in the Verbenaceae family and gentian in the gentian genus in the gentian family, etc. Modern studies have found that sesquiterpenoids have a wide range of biological activities such as antitumor, antibacterial, anti-inflammatory, antineurotoxic, antiviral, immunosuppressive activity, liver protection, and cardiotonic.

1. Sesquiterpene alcohol 

Sesquiterpene alcohol contains a structure composed of alcohol hydroxyl groups, all of which have a common group unit (-OH), and the functional group of sesquiterpene alcohol has a structure of 15 carbon atoms. Among the six most common sesquiterpene alcohols are farnesol, nerolidol, vetivol, patchouliol, sandalol, and eucalyptol. Sesquiterpene alcohol has a variety of biological activities, and studies have shown that sesquiterpene alcohol isolated from nerolidol has insecticidal activity and antitumor activity. Some sesquiterpene alcohol monomer compounds such as sesquiterpene alcohol extracted from resin-containing wood agarwood of the genus Agarwood inhibition inhibited the release of nitric oxide (NO) induced by lipopolysaccharide (LPS) in RAW264.7 macrophages, indicating that the compounds had good anti-inflammatory activity. The sesquiterpene alcohol and meadol, β-eucalyptol, γ-eucalyptol, elemenol and so on extracted from Atractylodes atractylodes have the effect of inhibiting gastric acid secretion, Helicobacter pylori and promoting the healing of peptic ulcer. 

2. Sesquiterpenone 

The ketone group is the oxygenated group that makes up the sesquiterpene ketone, the functional group of the ketone is the carbonyl group, and the two ends of the CO are connected with atomic clusters, that is, the chemical structure of all ketones has 1 common unit (C=O). Common sesquiterpenes include frangipani, damascenone, ionone, artemisinone, Atlantic ketone, and valenone, among others. Studies have shown that the α and β unsaturated ketones in the structure of sesquiterpenone have strong anti-tumor effects. The results of the study showed that the sesquiterpene ketone jimaketone in the extract of Curcuma had a time-dependent and dose-dependent inhibitory effect on hepatoma G2 cells. In addition to anti-tumor, the gemazone extracted from Curcuma can significantly reduce the degree of injury in mice with LPS-induced acute lung injury, and the mechanism of action is related to promoting M1 macrophage polarization to M2 and inhibiting the activation of  NOD-like receptor protein 3 (NLRP3) inflammasome, indicating that gemazone has a strong anti-inflammatory effect. The myrrh alkyl ketotimes obtained from the root of Angelica poly-morha Maxim., which belongs to the family Apiaceae, has good inhibition of ...

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