Diversolide

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The Diversolides are a group of chemical compounds in the family of sesquiterpene lactones isolated from the roots of Ferula diversivittata.

History

In 2008, Mehrdad Iranshahi from Mashhad University of Medical Sciences in Mashhad, Iran and his research group found seven sesquiterpene lactone derivatives which were isolated from the roots of Ferula diversivittata. They named them diversolides A–G (1–7).

The group members were Mehrdad Iranshahi and Seyyed Tahmineh Hosseini(Mashhad University of Medical Sciences,Mashhad,Iran), Ahmad Reza Shahverdi and Kamyar Mollazadeh Moghaddam (from Tehran University of Medical Sciences, Tehran, Iran) and Saleha Suleman Khan and Viqar Uddin Ahmad (from International Center for Chemical and Biological Sciences, Karachi, Pakistan).

Biological activities

Compounds 1, 4, and 6–8^{[clarification needed]} were tested for their in vitro antifungal and antibacterial activities against Staphylococcus aureus, Escherichia coli, Aspergillus niger and Candida albicans using gentamycin and fluconazole as positive controls. The compounds did not show any antifungal activity against Candida albicans at a range of 1.25–160 micrograms per mililiter. A lack of activity at a level of 160 μg/mL was considered "inactive". However, Staphylococcus aureus, Escherichia coli, Aspergillus niger had different^{[clarification needed]} susceptibility^{[clarification needed]} to the compounds at concentrations lower than 160 μg/mL. The best antimicrobial activity was observed against the filamentous fungus Aspergillus niger. This fungus was susceptible to all tested compounds, except to compound 1.

Chemical structure

Diversolide A (1); 2-methyl-but-2-enoic 3,6,9-trimethyl-3-(2-methyl-but-2-enoyloxy)-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydro-azuleno[4,5-b]furan-4-yl ester

Diversolide B (2); 2-methyl-but-2-enoic 3,6,9-trimethyl-3-(3-methyl-but-2-enoyloxy)-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydro-azuleno[4,5-b]furan-4-yl ester

Diversolide C (3) ; benzoic acid 3,6,9-trimethyl-3-(3-methyl-but-2-enoyloxy)-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydro-azuleno[4,5-b]furan-4-yl ester

Diversolide D (4); benzoic acid 3-acetoxy-3,6,9-trimethyl-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydro-azuleno[4,5-b]furan-4-yl ester

Diversolide E (5); 3,4-dimethoxy-benzoic acid 3,6,9-trimethyl-3-(2-methyl-but-2-enoyloxy)-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydro-azuleno[4,5-b]furan-4-yl ester

Diversolide F (6); 3,4-dimethoxy-benzoic acid 3,6,9-trimethyl-3-(3-methyl-but-2-enoyloxy)-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydro-azuleno[4,5-b]furan-4-yl ester

Diversolide G (7); 3,4-dimethoxy-benzoic acid 3-acetoxy-3,6,9-trimethyl-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydro-azuleno[4,5-b]furan-4-yl ester

^[1]

References

1. ^ Diversolides A–G, guaianolides from the roots of Ferula diversivittata

• Iranshahi M, Hosseini ST, Shahverdi AR, Molazade K, Khan SS, Ahmad VU (November 2008). "Diversolides A–G, guaianolides from the roots of Ferula diversivittata". Phytochemistry 69 (15): 2753–2757. doi:10.1016/j.phytochem.2008.08.009. PMID 18804823. 
• Iranshahi M, Hosseini ST, Shahverdi AR, Molazade K, Khan SS, Ahmad VU (2009). "Corrigenum to diversolides A–G guaianolides from the roots of Ferula diversivittata". Phytochemistry 70 (6): 822. 
• Alimirzaee P, Gohari AR, Hajiaghaee R, Mirzaee S, Jamalifar H Monsef-Esfahani HR, Amin Gh , Saeidnia S, Shahverdi AR (June 2009). "1-Methyl malate from Berberis integerrima fruits enhances the antibacterial activity of ampicillin against Staphylococcus aureus". Phytotherapy Research 23 (6): 797–800. doi:10.1002/ptr.2641.