PMID- 24689296
OWN - NLM
STAT- MEDLINE
DCOM- 20140527
LR  - 20211021
IS  - 1934-578X (Print)
IS  - 1555-9475 (Electronic)
IS  - 1555-9475 (Linking)
VI  - 9
IP  - 2
DP  - 2014 Feb
TI  - Methicillin-resistant Staphylococcus aureus, vancomycin-resistant Enterococcus 
      faecalis and Enterococcus faecium active dimeric isobutyrylphloroglucinol from 
      Ivesia gordonii.
PG  - 221-4
AB  - Bioassay-guided fractionation of the chloroform soluble fraction of stem, leaf, 
      and flower extracts of the American plant Ivesia gordonii led to the isolation of 
      a new dimeric acylphloroglucinol, 
      3,3'-diisobutyryl-2,6'-dimethoxy-4,6,2',4'-tetrahydroxy-5,5'dimethyldiphenyl 
      methane (1), to which we have assigned the trivial name ofivesinol (1), together 
      with a known monomeric acylphloroglucinol, 
      1,5-dihydroxy-2-(2'-methylpropionyl)-3-methoxy-6-methylbenzene (2). The 
      structures of the isolated compounds were characterized using 1D- and 2D- NMR 
      spectroscopy, including COSY, HMQC, HMBC, and ROESYexperiments, as well as mass 
      spectrometry. Ivesinol (1) showed potent activity against Staphylococcus aureus 
      (SA) and methicillin-resistant S. aureus (MRSA) with IC50/MIC/MBC values of 
      0.10/1.25/>20 microg/mL and 0.05/0.31/>20 microg/mL, respectively (vs. 
      IC50/MIC/MBC 0.13/0.5/1.0 microg/mL and 0.13/0.5/1.0 microg/mL of ciprofloxacin), 
      while the corresponding monomer 2 was found to be less active. Compound 1 also 
      demonstrated strong activity against vancomycin-resistant Enterococcus faecium 
      (VRE) with IC50/MlC/MBC values of 0.22/1.25/>20 microg/mL, whereas the reference 
      standard ciprofloxacin was found to be inactive against this strain. In addition, 
      compound 2 showed moderate activity against two species of Candida and 
      Cryptococcus neoformans, while 1 was inactive against these fungi. In order to 
      evaluate the influence of the acyl group(s) in phloroglucinol (3) as a ligand, 
      the mono- (4) and diacetylphloroglucinol (5) were prepared from 3, and evaluated 
      for their in vitro SA, MRSA, and VRE activities; 2,4-diacetylphloroglucinol (5) 
      showed potent activity, like 1, against SA, MRSA, and VRE (ATCC 700221) with 
      IC50/MIC values of 0.3/2.5, 0.23/2.5, and 0.86/2.5 microg/mL, respectively, while 
      4 was inactive.
FAU - Ahmed, Marwa H
AU  - Ahmed MH
FAU - Ibrahim, Mohamed Ali
AU  - Ibrahim MA
FAU - Zhang, Jin
AU  - Zhang J
FAU - Melek, Farouk R
AU  - Melek FR
FAU - El-Hawary, Seham S
AU  - El-Hawary SS
FAU - Jacob, Melissa R
AU  - Jacob MR
FAU - Muhammad, Ilias
AU  - Muhammad I
LA  - eng
GR  - R01 AI027094/AI/NIAID NIH HHS/United States
GR  - AI 27094/AI/NIAID NIH HHS/United States
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PT  - Research Support, Non-U.S. Gov't
PT  - Research Support, U.S. Gov't, Non-P.H.S.
PL  - United States
TA  - Nat Prod Commun
JT  - Natural product communications
JID - 101477873
RN  - 0 (Anti-Bacterial Agents)
RN  - 6Q205EH1VU (Vancomycin)
RN  - DHD7FFG6YS (Phloroglucinol)
SB  - IM
MH  - Anti-Bacterial Agents/*pharmacology
MH  - Enterococcus faecalis/*drug effects
MH  - Enterococcus faecium/*drug effects
MH  - Magnetic Resonance Spectroscopy
MH  - Methicillin-Resistant Staphylococcus aureus/*drug effects
MH  - Phloroglucinol/*analogs & derivatives/pharmacology
MH  - Rosaceae/*chemistry
MH  - Structure-Activity Relationship
MH  - Vancomycin/*pharmacology
PMC - PMC4130393
MID - NIHMS611196
EDAT- 2014/04/03 06:00
MHDA- 2014/05/28 06:00
PMCR- 2014/08/12
CRDT- 2014/04/03 06:00
PHST- 2014/04/03 06:00 [entrez]
PHST- 2014/04/03 06:00 [pubmed]
PHST- 2014/05/28 06:00 [medline]
PHST- 2014/08/12 00:00 [pmc-release]
PST - ppublish
SO  - Nat Prod Commun. 2014 Feb;9(2):221-4.