Tirucallol
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| Names | |
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| Preferred IUPAC name
(3β)-Dammara-7,24-dien-3-ol | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C30H50O | |
| Molar mass | 426.72 g/mol |
| Appearance | White to off-white solid |
| Density | ~1.0 g/cm3 (estimated) |
| Practically insoluble in water; soluble in ethanol, DMSO | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Not extensively studied; handle as potentially bioactive |
| Flash point | Not applicable |
| Not applicable | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tirucallol is a naturally occurring tetracyclic triterpenoid alcohol found in various plant species, notably in the latex of Euphorbia lactea and the resin of Pistacia lentiscus (mastic tree). It is structurally related to other triterpenes and has been studied for its potential anti-inflammatory and antioxidant properties.[1]
Occurrence
[edit]Tirucallol has been isolated from the latex of Euphorbia lactea and from the resin of Pistacia lentiscus, commonly known as mastic gum. These natural sources have been traditionally used for their medicinal properties, and the presence of tirucallol contributes to their bioactivity.[2][3]
Structure and biological activity
[edit]Tirucallol possesses a dammarane-type skeleton with a hydroxyl group at the 3β-position, classifying it as a tetracyclic triterpenoid alcohol. It is biosynthesized in plants via the mevalonate pathway, which leads to the formation of squalene and subsequent cyclization to various triterpenes.[1]
Research indicates that tirucallol exhibits several biological activities:
- Anti-inflammatory properties: Topical application of tirucallol has been shown to suppress ear edema in mouse models and inhibit nitrite production in lipopolysaccharide-stimulated macrophages, suggesting its potential as an anti-inflammatory agent.[2]
- Cardioprotective effects: Tirucallol has been found to inhibit the expression of adhesion molecules (VCAM-1 and ICAM-1) in tumor necrosis factor-alpha (TNF-α) stimulated human aortic endothelial cells, indicating a role in preventing endothelial dysfunction and atherosclerosis.[3]
Potential applications
[edit]Due to its natural origin and bioactive potential, tirucallol is particularly of interest in:
- Pharmaceutical research: Its anti-inflammatory and cardioprotective properties make it a candidate for drug development targeting related conditions.
- Nutraceutical development: As a component of mastic gum, it may contribute to the health benefits attributed to this traditional remedy.
- Cosmetic formulations: The compound's bioactivity may be beneficial in skincare products aimed at reducing inflammation and oxidative damage.
References
[edit]- ^ a b "Tirucallol". PubChem. Retrieved 2025-05-23.
- ^ a b Fernandez-Arche, A. (2010). "Topical anti-inflammatory effect of tirucallol, a triterpene isolated from Euphorbia lactea latex". Phytomedicine. 17 (2): 146–148. doi:10.1016/j.phymed.2009.05.009. PMID 19577446.
- ^ a b Loizou, S. (2009). "Chios Mastic Gum Extract and Isolated Phytosterol Tirucallol Exhibit Anti-Inflammatory Activity in Human Aortic Endothelial Cells". Experimental Biology and Medicine. 234 (5): 553–561. doi:10.3181/0811-RM-338. PMID 19234052.