Diversolide

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

History

Today there are at least 120 distinct chemical substances derived from plants which are considered important drugs currently in use in one or more countries. Isolating new chemical compounds from plants and developing them into new drugs is an important strategy in pharmacy and pharmacognosy research. [ [http://www.rain-tree.com/plantdrugs.htm Plant Based Drugs and Medicines] , Leslie Taylor, ND]

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 structures of these compounds were elucidated by extensive spectroscopic methods including 1D-(1H and 13C) and 2D-NMR experiments (DQF-COSY, HSQC, HMBC, and NOESY) as well as high-resolution EIMS (mass spectroscopy).

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 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 micro g/ml. However, "Staphylococcus aureus", "Escherichia coli", "Aspergillus niger" had different susceptibility to the compounds at concentrations lower than 160 micro g/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 (The higher test concentrations of 160 micro g/ml were considered inactive).

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

[ [http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TH7-4TGC3C2-3&_user=10&_coverDate=09/18/2008&_alid=799695546&_rdoc=1&_fmt=high&_orig=search&_cdi=5275&_sort=d&_docanchor=&view=c&_ct=1&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=559a3d941ec77672b5e66bc36655e4fa Diversolides A–G, guaianolides from the roots of Ferula diversivittata ] ]

References

External links

* [http://www.ars-grin.gov/cgi-bin/npgs/html/taxon.pl?16607 Ferula diversivittata]
* [http://www.tums.ac.ir/english/faculties/?facultyID=930 Dr.Ahmad Reza Shahverdi]
* [http://www.mums.ac.ir/pharmacy/en/iranshahicv Dr.Mehrdad Iranshahi]