ACS Medicinal Chemistry Letters
Letter
Cancer Center (OSUCCC), Grant #IRG-67-003-47 from the
American Cancer Society and OSUCCC Pelotonia New Idea
Grant (all to J.Y.), and by Grant P01 CA125066 from the
National Cancer Institute, NIH (Bethesda, MD) (to A.D.K).
Other financial assistance was obtained from MetaCor
Pharmaceuticals, Inc., and the Edison Program of the State of
Ohio.
(11) Kumar, A.; Sushama, A.; Rohil, V.; Manral, S.; Gangopadhyay,
S.; Prasad, A. K.; Raj, H. G.; Parmar, V. S. Prevention of benzene-
induced genotoxicity in bone marrow and lung cells: superiority of
polyphenolic acetates to polyphenols. Arch. Toxicol. 2011, 85, 1141−
1
150.
12) Alam, A.; Takaguchi, Y.; Tsuboi, S. Synthesis of ellagic acid and
(
its 4,4′-di-O-alkyl derivatives from gallic acid. J. Fac. Environ. Sci.
Technol. Okayama Univ. 2005, 10, 111−117.
Notes
(13) Alam, A.; Tsuboi, S. Total synthesis of 3,3′,4-tri-O-methylellagic
acid from gallic acid. Tetrahedron 2007, 63, 10454−10465.
The authors declare no competing financial interest.
(14) Daniel, E. M.; Ratnayake, S.; Kinstle, T.; Stoner, G. D. The
effects of pH and rat intestinal contents on the liberation of ellagic acid
from purified and crude ellagitannins. J. Nat. Prod. 1991, 54, 946−952.
ACKNOWLEDGMENTS
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́ ́
(15) Larrosa, M.; Tomas-Barberan, F. A.; Espín, J. C. The dietary
We are grateful to Jack Fowble, College of Pharmacy, The Ohio
State University, for access to the NMR spectrometers used and
Dr. Kari Green-Church, Mass Spectrometry and Proteomics
Laboratory, Campus Chemical Instrument Center, The Ohio
State University, for the MS measurements.
hydrolysable tannin punicalagin releases ellagic acid that induces
apoptosis in human colon adenocarcinoma Caco-2 cells by using the
mitochondrial pathway. J. Nutr. Biochem. 2006, 17, 611−625.
(16) Ren, Y.; Himmeldirk, K.; Chen, X. Synthesis and structure-
activity relationship study of antidiabetic penta-O-galloyl-D-glucopyr-
anose and its analogues. J. Med. Chem. 2006, 49, 2829−2837.
(17) Da Silva, S. L.; Chaar, J.; da, S.; Yano, T. Chemotherapeutic
potential of two gallic acid derivative compounds from leaves of
Casearia sylvestris Sw. (Flacourtiaceae). Eur. J. Pharmacol. 2009, 608,
ABBREVIATIONS
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PGG, pentagalloylglucopyranose; NK, natural killer; AFB ,
1
aflatoxin B ; CYP450, cytochrome P450; MFO, mixed func-
1
7
(
6−83.
tion oxidase; DCC, dicyclohexylcarbodiimide; DMAP, 4-
dimethylamino)pyridine; WBC, white blood cell; BM, bone
marrow; LAMP-1 or CD107a, lysosomal-associated membrane
protein-1; IFN-γ, interferon-γ
18) Yu, J.; Wei, M.; Becknell, B.; Trotta, R.; Liu, S.; Boyd, Z.; Jaung,
(
M. S.; Blaser, B. W.; Sun, J.; Benson, D. M.; Mao, H.; Yokohama, A.;
Bhatt, D.; Shen, L.; Davuluri, R.; Weinstein, M.; Marcucci, G.;
Caligiuri, M. A. Pro- and antiinflammatory cytokine signaling:
Reciprocal antagonism regulates interferon-gamma production by
human natural killer cells. Immunity 2006, 24, 575−590.
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dx.doi.org/10.1021/ml300065z | ACS Med. Chem. Lett. 2012, 3, 631−636