Masticadienolic acid

Masticadienolic acid

Skeletal formula
Names
Preferred IUPAC name (Z,6S)-6-[(3S,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoic acid
Identifiers
CAS Number	472-30-0
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL5266227
ChemSpider	28425558
PubChem CID	102004474
InChI InChI=1S/C30H48O3/c1-19(9-8-10-20(2)26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h10-11,19,21-22,24-25,31H,8-9,12-18H2,1-7H3,(H,32,33)/b20-10-/t19-,21-,22-,24-,25-,28+,29-,30+/m0/s1 Key: UILQHUKSFUOOLH-MCGHDPRASA-N
SMILES C[C@@H](CC/C=C(/C)\C(=O)O)[C@@H]1CC[C@]2([C@]1(CC[C@H]3C2=CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C
Properties
Chemical formula	C30H48O3
Molar mass	456.71 g/mol
Appearance	White to off-white solid
Density	~1.0 g/cm3 (estimated)
Solubility in water	Practically insoluble in water; soluble in ethanol, DMSO
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Not extensively studied; handle as potentially bioactive
Flash point	Not applicable
Autoignition temperature	Not applicable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N (what is  YN ?) Infobox references

Masticadienolic acid is a naturally occurring terpenoid compound found in the resin of the mastic tree ( Pistacia lentiscus ), particularly in the variety cultivated on the Greek island of Chios. Chemically, it is a tirucallane-type tetracyclic triterpenoid based on its structural characteristics and biosynthetic origin. It is structurally related strongly to masticadienonic acid, differing by the presence of a hydroxyl group, which may influence its biological activity. ^[1]

Occurrence

Masticadienolic acid is one of the major constituents of mastic gum, a natural resin exuded from the bark of Pistacia lentiscus. This resin has been traditionally used for its medicinal properties and is known to contain various triterpenoids, including masticadienolic acid. ^[2]

Structure and biological activity

This natural substance possesses a lanostane-type skeleton with a carboxylic acid group and a hydroxyl group, classifying it as a pentacyclic triterpenoid. It is biosynthesized in the plant via the mevalonate pathway, a common route for the formation of triterpenes and steroids. ^[3]

Research indicates that masticadienolic acid exhibits several biological activities, such as:

• Anti-inflammatory properties: It may modulate pro-inflammatory pathways, contributing to its traditional use in treating inflammatory conditions. ^[4]
• Antioxidant effects: The compound has been associated with antioxidant activity, which can protect cells from oxidative stress. ^[5]
• Potential anticancer activity: Preliminary studies suggest that masticadienolic acid may have cytotoxic effects on certain cancer cell lines, although further research is needed to confirm these findings. ^[6]

Applications

Due to its natural origin and bioactive potential, masticadienolic acid is of interest in:

• Nutraceutical development: As a component of mastic gum, it may contribute to the health benefits attributed to this traditional remedy.
• Pharmaceutical research: Its anti-inflammatory and antioxidant properties make it a candidate for drug development targeting related conditions.
• Cosmetic formulations: The compound's bioactivity may be beneficial in skincare products aimed at reducing inflammation and oxidative damage.

References

1. "Masticadienolic acid". PubChem. Retrieved 2025-05-23.
2. Tabanca, N. (2020). "Chemical Characterization and Biological Activity of the Mastic Gum Essential Oils of Pistacia lentiscus var. chia from Turkey". Molecules. 25 (9): 2136. doi: 10.3390/molecules25092136 . PMC   7248992 . PMID   32370246.
3. "Masticadienolic acid". PubChem. Retrieved 2025-05-23.
4. Paraschos, S. (2007). "Chemical Composition and Antibacterial Activity of the Essential Oils from the Resin of Pistacia lentiscus". Journal of Agricultural and Food Chemistry. 55 (18): 7686–7690. doi:10.1021/jf070509f (inactive 24 May 2025).
5. Paraschos, S. (2007). "Chemical Composition and Antibacterial Activity of the Essential Oils from the Resin of Pistacia lentiscus". Journal of Agricultural and Food Chemistry. 55 (18): 7686–7690. doi:10.1021/jf070509f (inactive 24 May 2025).
6. Paraschos, S. (2007). "Chemical Composition and Antibacterial Activity of the Essential Oils from the Resin of Pistacia lentiscus". Journal of Agricultural and Food Chemistry. 55 (18): 7686–7690. doi:10.1021/jf070509f (inactive 24 May 2025).