Madecassic acid

Madecassic acid

Names
IUPAC name (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Other names Brahmic acid
Identifiers
CAS Number	18449-41-7  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:73058  Y
ChEMBL	ChEMBL481854
ChemSpider	66126
DrugBank	DB14037
ECHA InfoCard	100.113.087
EC Number	606-031-1
PubChem CID	73412
UNII	M7O1N24J82  Y
CompTox Dashboard (EPA)	DTXSID70939838
InChI InChI=1S/C30H48O6/c1-16-9-10-30(25(35)36)12-11-28(5)18(22(30)17(16)2)7-8-21-26(3)13-20(33)24(34)27(4,15-31)23(26)19(32)14-29(21,28)6/h7,16-17,19-24,31-34H,8-15H2,1-6H3,(H,35,36)/t16-,17+,19-,20-,21-,22+,23-,24+,26-,27+,28-,29-,30+/m1/s1 N Key: PRAUVHZJPXOEIF-AOLYGAPISA-N Y
SMILES C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(C[C@H]([C@@H]5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)O)C)[C@@H]2[C@H]1C)C)C(=O)O
Properties
Chemical formula	C30H48O6
Molar mass	504.708 g·mol−1
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

Madecassic acid is a pentacyclic triterpenoid compound that occurs naturally in several plant species. ^{[1] [2]} Madecassic acid is a member of the ursane-type triterpenoids and is structurally similar to asiatic acid, differing by the presence of a hydroxyl group at the C-2 position. ^[3]

Natural occurence

The acid is found in Centella asiatica (Gotu Kola). ^[4] Other sources include Centella cordifolia and Hydrocotyle umbellata . The compound is closely related to asiatic acid and is known for its various pharmacological properties, including anti-inflammatory, wound-healing, anti-oxidant, and neuroprotective effects. ^[5] It is often studied alongside other bioactive compounds from Centella asiatica. ^{[6] [7] [8] [9]}

Uses

Madecassic acid is used in both traditional and modern medicine, particularly in dermatology and wound care. ^[10] As a triterpene, madecassic acid also exhibits notable antioxidant benefits, assisting in protecting skin from the pro-aging damage that environmental aggressors, like UV rays and pollution, can cause.

See also

• Madecassoside

References

1. Bajaj, Y. P. S. (6 December 2012). Medicinal and Aromatic Plants X. Springer Science & Business Media. p. 82. ISBN   978-3-642-58833-4 . Retrieved 21 July 2025.
2. "Madecassic acid". Sigma Aldrich . Retrieved 21 July 2025.
3. Swamy, Mallappa Kumara; Patra, Jayanta Kumar; Rudramurthy, Gudepalya Renukaiah (10 May 2019). Medicinal Plants: Chemistry, Pharmacology, and Therapeutic Applications. CRC Press. ISBN   978-0-429-53560-4 . Retrieved 21 July 2025.
4. Khare, C. P. (27 June 2011). Indian Herbal Remedies: Rational Western Therapy, Ayurvedic and Other Traditional Usage, Botany. Springer Science & Business Media. p. 139. ISBN   978-3-642-18659-2 . Retrieved 21 July 2025.
5. Banik, Bimal Krishna; Sahoo, Biswa Mohan; Tiwari, Abhishek (23 December 2022). Terpenoids: Chemistry, Biochemistry, Medicinal Effects, Ethno-pharmacology. CRC Press. p. 318. ISBN   978-1-000-82349-3 . Retrieved 21 July 2025.
6. Kasote, Deepak; Ahmad, Aijaz; Viljoen, Alvaro (2015). "Proangiogenic Potential of Medicinal Plants in Wound Healing". Evidence-Based Validation of Herbal Medicine. pp. 149–164. doi:10.1016/B978-0-12-800874-4.00006-4. ISBN   978-0-12-800874-4.
7. Kepekçi, Remziye Aysun; Yener i̇Lçe, Burcu; Demir Kanmazalp, Sibel (2021). "Plant-derived biomaterials for wound healing". Bioactive Natural Products. Studies in Natural Products Chemistry. Vol. 70. pp. 227–264. doi:10.1016/B978-0-12-819489-8.00001-6. ISBN   978-0-12-819489-8.
8. Nabi, Bushra; Rehman, Saleha; Baboota, Sanjula; Ali, Javed (2019). "Natural antileprotic agents: A boon for the management of leprosy". Discovery and Development of Therapeutics from Natural Products Against Neglected Tropical Diseases. pp. 351–372. doi:10.1016/B978-0-12-815723-7.00009-2. ISBN   978-0-12-815723-7.
9. Awathale, Sanjay N.; Dhoble, Leena R.; Itankar, Prakash R.; Raut, Nishikant A.; Kokare, Dadasaheb M. (2021). "Neuroactive herbal agents for cognitive dysfunction". Bioactive Natural Products. Studies in Natural Products Chemistry. Vol. 70. pp. 195–226. doi:10.1016/B978-0-12-819489-8.00002-8. ISBN   978-0-12-819489-8.
10. Tang, Weici; Eisenbrand, Gerhard (29 June 2013). Chinese Drugs of Plant Origin: Chemistry, Pharmacology, and Use in Traditional and Modern Medicine. Springer Science & Business Media. p. 275. ISBN   978-3-642-73739-8 . Retrieved 21 July 2025.