Ajugarin I

• CAT Number: I021657
• CAS Number: 62640-05-5
• Molecular Formula: C24H34O7
• Molecular Weight: 434.53
• Purity: 98%
• Synonyms: Ajugarin I
• IUPAC Name: 2(5H)-Furanone, 4-(2-(8-(acetyloxy)-8a-((acetyloxy)methyl)octahydro-5,6-dimethylspiro(naphthalene-1(2H),2'-oxiran)-5-yl)ethyl)-, (1R-(1alpha,4abeta,5beta,6alpha,8alpha,8aalpha))-
• InChI: InChI=1S/C24H34O7/c1-15-10-20(31-17(3)26)24(14-29-16(2)25)19(6-5-8-23(24)13-30-23)22(15,4)9-7-18-11-21(27)28-12-18/h11,15,19-20H,5-10,12-14H2,1-4H3/t15-,19-,20+,22+,23+,24+/m1/s1
• InChIKey: RNYBNBANBCQZON-PGQNDPHJSA-N
• SMILES: O=C1OCC(CC[C@]2(C)[C@@]3([H])CCC[C@@]4(OC4)[C@]3(COC(C)=O)[C@@H](OC(C)=O)C[C@H]2C)=C1

Ajugarin I is a clerodane diterpene; the major component of the shrub Ajuga remota.

Reference

1: Castro A, Coll J, Pant AK, Pakrash O. neo-Clerodane Diterpenoids from Ajuga macrosperma var. breviflora. Nat Prod Commun. 2015 Jun;10(6):857-60. PubMed PMID: 26197499.
2: Cocquyt K, Cos P, Herdewijn P, Maes L, Van den Steen PE, Laekeman G. Ajuga remota Benth.: from ethnopharmacology to phytomedical perspective in the treatment of malaria. Phytomedicine. 2011 Nov 15;18(14):1229-37. doi: 10.1016/j.phymed.2011.08.063. Epub 2011 Oct 19. Review. PubMed PMID: 22015320.
3: Gautam R, Jachak SM, Saklani A. Anti-inflammatory effect of Ajuga bracteosa Wall Ex Benth. mediated through cyclooxygenase (COX) inhibition. J Ethnopharmacol. 2011 Jan 27;133(2):928-30. doi: 10.1016/j.jep.2010.11.003. Epub 2010 Nov 10. PubMed PMID: 21073945.
4: Singh N, Mahmood U, Kaul VK, Jirovetz L. A new phthalic acid ester from Ajuga bracteosa. Nat Prod Res. 2006 May 20;20(6):593-7. PubMed PMID: 16835093.
5: Manguro LO, Wagai SO, Lemmen P. Flavonol and iridoid glycosides of Ajuga remota aerial parts. Phytochemistry. 2006 Apr;67(8):830-7. Epub 2006 Mar 9. PubMed PMID: 16524603.
6: Coll J. NMR shift data of neo-clerodane diterpenes from the genus Ajuga. Phytochem Anal. 2002 Nov-Dec;13(6):372-80. PubMed PMID: 12494759.
7: Kuria KA, Chepkwony H, Govaerts C, Roets E, Busson R, De Witte P, Zupko I, Hoornaert G, Quirynen L, Maes L, Janssens L, Hoogmartens J, Laekeman G. The antiplasmodial activity of isolates from Ajuga remota. J Nat Prod. 2002 May;65(5):789-93. PubMed PMID: 12027771.
8: Carbonell P, Coll J. Ajugatansins, neo-clerodane diterpenes from Ajuga reptans. Phytochem Anal. 2001 Jan-Feb;12(1):73-8. PubMed PMID: 11704966.
9: Caballero C, Castañera P, Ortego F, Fontana G, Pierro P, Savona G, Rodríguez B. Effects of ajugarins and related neoclerodane diterpenoids on feeding behaviour of Leptinotarsa decemlineata and Spodoptera exigua larvae. Phytochemistry. 2001 Sep;58(2):249-56. PubMed PMID: 11551547.
10: Cantrell CL, Rajab MS, Franzblau SG, Fronczek FR, Fischer NH. Antimycobacterial ergosterol-5,8-endoperoxide from Ajuga remota. Planta Med. 1999 Dec;65(8):732-4. PubMed PMID: 10630115.
11: Odek-Ogunde M, Rajab MS. Antihypertensive effect of the clerodane diterpene ajugarin I on experimentally hypertensive rats. East Afr Med J. 1994 Sep;71(9):587-90. PubMed PMID: 7875092.