In Vitro Antimicrobial Activity of Isopimarane-Type Diterpenoids.

Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE

Original Publication: Basel, Switzerland : MDPI, c1995-

Abietanes/*chemistry ; Anti-Infective Agents/*chemistry ; Diterpenes/*chemistry; Anti-Infective Agents/pharmacology ; Cell Line, Tumor ; Cell Proliferation/drug effects ; Cell Survival/drug effects ; Diterpenes/pharmacology ; Enterococcus faecalis/drug effects ; Gram-Positive Bacteria/drug effects ; Humans ; Methicillin-Resistant Staphylococcus aureus/drug effects ; Microbial Sensitivity Tests ; Structure-Activity Relationship ; Vancomycin Resistance/drug effects

The antimicrobial evaluation of twelve natural and hemisynthetic isopimarane diterpenes are reported. The compounds were evaluated against a panel of Gram-positive bacteria, including two methicillin-resistant Staphylococcus aureus (MRSA) strains and one vancomycin-resistant Enterococcus (VRE) strain. Only natural compounds 7,15-isopimaradien-19-ol ( 1 ) and 19-acetoxy-7,15-isopimaradien-3β-ol ( 6 ) showed promising results. Isopimarane ( 1 ) was the most active, showing MIC values between 6.76 µM against S. aureus (ATCC 43866) and 216.62 µM against E. faecalis (FFHB 427483) and E. flavescens (ATCC 49996). Compound ( 6 ) showed moderated activity against all tested microorganisms (MIC between value 22.54 and 45.07 µM). These compounds were found to be active against the methicillin-sensitive strains of S. aureus (CIP 106760 and FFHB 29593), showing MIC values of 13.55 ( 1 ) and 22.54 ( 6 ) µM. Both compounds were also active against vancomycin-resistant E. faecalis (ATCC 51299) (MIC values of 54.14 and 45.07 µM, respectively). In addition, the cytotoxicity of nine compounds 7,15-isopimaradien-3β,19-diol ( 2 ); mixture: 15-isopimarene-8β-isobutyryloxy-19-ol and 15-isopimarene-8β-butyryloxy-19-ol ( 3 ); 3β-acetoxy-7,15-isopimaradiene-19-ol ( 5 ); 19-acetoxy-7,15-isopimaradiene-3β-ol ( 6 ); 3β,19-diacetoxy-7,15-isopimaradiene ( 8 ); 15-isopimarene-8β,19-diol ( 9 ); 19- O -β-d-glucopyranoside-7,15-isopimaradiene ( 10 ); lagascatriol-16- O -β-d-glucopyranoside ( 11 ) and lagascatriol-16- O -α-d-mannopyranoside ( 12 ) was evaluated in the human breast cancer cell line MDA-MB-231. Isopimarane ( 2 ) was the only compound showing some cytotoxicity. The IC 50 value of compound ( 2 ) was 15 µM, suggesting a mild antiproliferative activity against these breast cancer cells.

Mutat Res. 2013 Oct 9;757(2):140-7. (PMID: 23958474)
J Ethnopharmacol. 2011 Oct 11;137(3):1089-94. (PMID: 21798328)
Arch Pharm Res. 2013 Aug;36(8):957-65. (PMID: 23604820)
Fitoterapia. 2009 Oct;80(7):432-6. (PMID: 19524643)
Trends Pharmacol Sci. 2016 Aug;37(8):689-701. (PMID: 27267698)
Inflamm Allergy Drug Targets. 2009 Mar;8(1):28-39. (PMID: 19275691)
Phytochemistry. 2009 Jun;70(9):1161-1165. (PMID: 19631355)
Molecules. 2011 Jan 13;16(1):543-51. (PMID: 21233793)
Biochim Biophys Acta. 2013 Jun;1830(6):3670-95. (PMID: 23428572)
Phytother Res. 2013 Oct;27(10):1502-7. (PMID: 23193079)
Pharmazie. 2014 Feb;69(2):148-53. (PMID: 24640606)
Phytochemistry. 2013 May;89:125-30. (PMID: 23465717)
Molecules. 2009 Jan 04;14(1):191-9. (PMID: 19127247)
Molecules. 2013 Jul 15;18(7):8298-318. (PMID: 23860277)
Chem Rev. 2012 Nov 14;112(11):5967-6026. (PMID: 22967178)
Free Radic Res. 2010 Apr;44(4):430-40. (PMID: 20102317)
J Nat Prod. 2003 Feb;66(2):242-6. (PMID: 12608857)
Chem Pharm Bull (Tokyo). 2003 May;51(5):605-7. (PMID: 12736467)
Infect Dis (Auckl). 2017 May 22;10:1179916117703999. (PMID: 28579798)

Keywords: MDA-MB-231 cells; antimicrobial; isopimaranes

0 (Abietanes)
0 (Anti-Infective Agents)
0 (Diterpenes)

Date Created: 20200919 Date Completed: 20210310 Latest Revision: 20210310

20231215

PMC7570906

10.3390/molecules25184250

32947912