Triterpenoids are a class of chemical compounds found in many plants and fungi, known for their biological and therapeutic properties. These compounds belong to the terpene family and are characterized by a base structure of 30 carbon atoms.

Chemical Composition and Structure:

Triterpenoids are derived from squalene and have a chemical structure that can vary widely, including:

• 30-Carbon Base Structure: Common to all triterpenoids.
• Various Functional Groups: May include hydroxyl, carbonyl, and other chemical modifications that influence their properties.
• Classification: Can be divided into several groups, including saponins, steroids, and others, based on their structure and function.

Physical Properties:

• Appearance: Varies from crystalline solids to viscous liquids, depending on the specific chemical structure.
• Odor: Generally odorless or with weak odors, depending on origin and purity.
• Solubility: Typically soluble in organic solvents like alcohol and oils, but generally insoluble in water.

Production Process:

The production of triterpenoids can involve:

1. Extraction: Derived from natural sources like plants and fungi using appropriate solvents.
2. Purification: Raw extracts are purified through techniques such as chromatography to obtain pure triterpenoids.
3. Synthesis (optional): Some triterpenoids can be synthesized in the laboratory for specific purposes.

Applications:

• Medical: Triterpenoids are studied for their anti-inflammatory, antitumor, and immunomodulatory properties. They are used in dietary supplements and therapeutic preparations.
• Cosmetics: In skincare, they are valued for their anti-aging, moisturizing, and regenerating properties. They can be found in creams, serums, and skin treatments.
• Others: Also used in natural products and phytotherapy for their beneficial effects.

Environmental and Safety Considerations:

Triterpenoids are generally considered safe and biodegradable, but safety depends on the source and purity. It is important to ensure they are produced using sustainable practices and are free from contaminants. Some triterpenoids may cause allergic reactions or side effects in sensitive individuals, so sensitivity testing is recommended when used in cosmetic products.

References__________________________________________________________________________

Petronelli A, Pannitteri G, Testa U. Triterpenoids as new promising anticancer drugs. Anticancer Drugs. 2009 Nov;20(10):880-92. doi: 10.1097/CAD.0b013e328330fd90. PMID: 19745720.

Abstract. Triterpenoids are structurally diverse organic compounds, characterized by a basic backbone modified in multiple ways, allowing the formation of more than 20 000 naturally occurring triterpenoid varieties. Several triterpenoids, including ursolic and oleanolic acid, betulinic acid, celastrol, pristimerin, lupeol, and avicins possess antitumor and anti-inflammatory properties. To improve antitumor activity, some synthetic triterpenoid derivatives have been synthesized, including cyano-3,12-dioxooleana-1,9 (11)-dien-28-oic (CDDO), its methyl ester (CDDO-Me), and imidazolide (CDDO-Im) derivatives. Of these, CDDO, CDDO-Me, and betulinic acid have shown promising antitumor activities and are presently under evaluation in phase I studies. Triterpenoids are highly multifunctional and the antitumor activity of these compounds is measured by their ability to block nuclear factor-kappaB activation, induce apoptosis, inhibit signal transducer, and activate transcription and angiogenesis.

Mahato SB, Nandy AK, Roy G. Triterpenoids. Phytochemistry. 1992 Jul;31(7):2199-49. doi: 10.1016/0031-9422(92)83257-y. PMID: 1368386.

Abstract. Triterpenoids isolated and characterized from various sources are reviewed. The newer techniques used in their isolation and structure elucidation, the newer skeleton triterpenoids characterized, chemical modifications and synthetic studies reported are discussed. A compilation of the triterpenoids isolated during the period 1982-1989 along with their occurrence, available physical data, spectroscopy and X-ray analysis used for their characterization, is included. The biological activities of the triterpenoids are also described.

Connolly JD, Hill RA. Triterpenoids. Nat Prod Rep. 2008 Aug;25(4):794-830. doi: 10.1039/b718038c. Epub 2008 Jun 20. PMID: 18663395.

Abstract. This review covers the isolation and structure determination of triterpenoids including squalene derivatives, protostanes, lanostanes, holostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, isomalabaricanes and saponins. The literature from January 2005 to December 2006 is reviewed and 478 references are cited.

Wimmerová M, Bildziukevich U, Wimmer Z. Selected Plant Triterpenoids and Their Derivatives as Antiviral Agents. Molecules. 2023 Nov 22;28(23):7718. doi: 10.3390/molecules28237718. 

Abstract. The results of the most recent investigation of triterpenoid-based antiviral agents namely in the HIV-1 and HSV-1 treatment were reviewed and summarized. Several key historical achievements are included to stress consequences and continuity in this research. Most of the agents studied belong to a series of compounds derived from betulin or betulinic acid, and their synthetic derivative is called bevirimat. A termination of clinical trials of bevirimat in Phase IIb initiated a search for more successful compounds partly derived from bevirimat or designed independently of bevirimat structure. Surprisingly, a majority of bevirimat mimics are derivatives of betulinic acid, while other plant triterpenoids, such as ursolic acid, oleanolic acid, glycyrrhetinic acid, or other miscellaneous triterpenoids, are relatively rarely involved in a search for a novel antiviral agent. Therefore, this review article is divided into three parts based on the leading triterpenoid core structure.

Zhu JJ, Yang HX, Li ZH, Wang GK, Feng T, Liu JK. Anti-inflammatory lupane triterpenoids from Menyanthes trifoliata. J Asian Nat Prod Res. 2019 Jul;21(7):597-602. doi: 10.1080/10286020.2018.1460363. Epub 2018 Apr 16. PMID: 29658298.

Abstract. A new lupane triterpenoid, 23-O-trans-feruloylcylicodiscic acid (1), as well as four known analogues (2‒5), was isolated from the EtOAc fraction of Menyanthes trefoliata. The structure of compound 1 was elucidated on the basis of extensive spectroscopic analysis, including 2D NMR data. The structures of the known compounds were established by comparison of their spectroscopic data with that in the literature. Compounds 1, 2, and 4 exhibited certain anti-NO production activities.