Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: A mechanistic and 3-D structure-activity study

Phytomedicine

Volumn 20, Issue 8-9, 2013, Pages 734-742

  Gasmi, Jihane ^a   Thomas Sanderson, J ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

3 D conformation; Apoptosis; Death receptor; Extrinsic; Geoisomers; Intrinsic; Jacaric acid; Prostate cancer; PubChem Compound Database; Punicic acid; Structure activity

Indexed keywords

ALPHA CALENDIC ACID; ANTINEOPLASTIC AGENT; BETA CALENDIC ACID; CASPASE 3; CASPASE 8; CASPASE 9; CATALPIC ACID; JACARIC ACID; OCTADECATRIENOIC ACID; PUNICIC ACID; UNCLASSIFIED DRUG; VACCENIC ACID;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CYTOTOXICITY; HUMAN; HUMAN CELL; JACARANDA; MALE; POMEGRANATE; PRIORITY JOURNAL; PROSTATE CANCER; STRUCTURE ACTIVITY RELATION;

APOPTOSIS; APOPTOSIS REGULATORY PROTEINS; BIGNONIACEAE; CELL LINE, TUMOR; CELL SURVIVAL; DATABASES, CHEMICAL; DOSE-RESPONSE RELATIONSHIP, DRUG; FATTY ACIDS; HUMANS; LINOLENIC ACIDS; MALE; MODELS, STRUCTURAL; OLEIC ACIDS; PLANT OILS; PROSTATIC NEOPLASMS; PUNICACEAE; SEEDS; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS;

JACARANDA; LYTHRACEAE;

EID: 84878109067     PISSN: 09447113     EISSN: 1618095X     Source Type: Journal    
DOI: 10.1016/j.phymed.2013.01.012     Document Type: Article

References (39)

1. E.E. Bolton, J. Chen, S. Kim, L. Han, S. He, W. Shi, V. Simonyan, Y. Sun, P.A. Thiessen, J. Wang, B. Yu, J. Zhang, and S.H. Bryant PubChem3D: a new resource for scientists Journal of Cheminformatics 3 2011 32
2. E.E. Bolton, S. Kim, and S.H. Bryant PubChem3D: conformer generation Journal of Cheminformatics 3 2011 4
3. E.E. Bolton, S. Kim, and S.H. Bryant PubChem3D: diversity of shape Journal of Cheminformatics 3 2011 9
4. E.E. Bolton, S. Kim, and S.H. Bryant PubChem3D: similar conformers Journal of Cheminformatics 3 2011 13
5. X. Chen, H. Thakkar, F. Tyan, S. Gim, H. Robinson, C. Lee, S.K. Pandey, C. Nwokorie, N. Onwudiwe, and R.K. Srivastava Constitutively active Akt is an important regulator of TRAIL sensitivity in prostate cancer Oncogene 20 2001 6073 6083
6. M.J. Chisholm, and C.Y. Hopkins Conjugated fatty acids in some curcubitaceae seed oils Can Journal of Biochemistry 45 1967 1081 1086
7. P.A. Christian, J.A. Thorpe, and S.R. Schwarze Velcade sensitizes prostate cancer cells to TRAIL induced apoptosis and suppresses tumor growth in vivo Cancer Biology and Therapy 8 2009 73 80
8. M. Colombel, F. Symmans, S. Gil, K.M. O'Toole, D. Chopin, M. Benson, C.A. Olsson, S. Korsmeyer, and R. Buttyan Detection of the apoptosis-suppressing oncoprotein bc1-2 in hormone-refractory human prostate cancers The American Journal of Pathology 143 1993 390 400
9. F. Destaillats, E. Buyukpamukcu, P.A. Golay, F. Dionisi, and F. Giuffrida Vaccenic and rumenic acids, a distinct feature of ruminant fats Journal of Dairy Science 88 2005 449
10. M.I. El-Shaarawy, and A. Nahapetian Studies of pomegranate seed oil Fette Seifen Austrichmittel 85 1983 123 126
11. A.L. Gartel p21(WAF1/CIP1) and cancer: a shifting paradigm? Biofactors 35 2009 161 164
12. J. Gasmi, and J.T. Sanderson Growth inhibitory, antiandrogenic, and pro-apoptotic effects of punicic acid in LNCaP human prostate cancer cells Journal of Agricultural and Food Chemistry 58 2010 12149 12156
13. M. Gorospe, C. Cirielli, X. Wang, P. Seth, M.C. Capogrossi, and N.J. Holbrook p21(Waf1/Cip1) protects against p53-mediated apoptosis of human melanoma cells Oncogene 14 1997 929 935
14. A. Hague, G.D. Diaz, D.J. Hicks, S. Krajewski, J.C. Reed, and C. Paraskeva bcl-2 and bak may play a pivotal role in sodium butyrate-induced apoptosis in colonic epithelial cells; however overexpression of bcl-2 does not protect against bak-mediated apoptosis International Journal of Cancer 72 1997 898 905
15. P.C. Hawkins, A.G. Skillman, G.L. Warren, B.A. Ellingson, and M.T. Stahl Conformer generation with OMEGA: algorithm and validation using high quality structures from the Protein Databank and Cambridge Structural Database Journal of Chemical Information and Modeling 50 2010 572 584
16. D. Hockenbery, G. Nunez, C. Milliman, R.D. Schreiber, and S.J. Korsmeyer Bcl-2 is an inner mitochondrial membrane protein that blocks programmed cell death Nature 348 1990 334 336
17. Y. Kadowaki, N.S. Chari, A.E. Teo, A. Hashi, K.B. Spurgers, and T.J. McDonnell PI3 Kinase inhibition on TRAIL-induced apoptosis correlates with androgen-sensitivity and p21 expression in prostate cancer cells Apoptosis: An International Journal on Programmed Cell Death 16 2011 627 635
18. Y. Li, A.J. Raffo, L. Drew, Y. Mao, A. Tran, D.P. Petrylak, and R.L. Fine Fas-mediated apoptosis is dependent on wild-type p53 status in human cancer cells expressing a temperature-sensitive p53 mutant alanine-143 Cancer Research 63 2003 1527 1533
19. L. Liu, E.G. Hammond, and B.J. Nikolau In vivo studies of the biosynthesis of [alpha]-eleostearic acid in the seed of Momordica charantia L. Plant Physiology 113 1997 1343 1349
20. S. Ozgul-Yucel Determination of conjugated linolenic acid content of selected oil seeds grown in Turkey Journal of the American Oil Chemists Society 82 2005 893 897
21. C. Pourzand, G. Rossier, O. Reelfs, C. Borner, and R.M. Tyrrell Overxpression of Bcl-2 inhibits UVA-mediated immediate apoptosis in rat 6 fibroblasts: evidence for the involvement of Bcl-2 as an antioxidant Cancer Research 57 1997 1405 1411
22. J.C. Reed Bcl-2 and the regulation of programmed cell death Journal of Cell Biology 124 1994 1 6
23. S.L. Scott, J.D. Earle, and P.H. Gumerlock Functional p53 increases prostate cancer cell survival after exposure to fractionated doses of ionizing radiation Cancer Research 63 2003 7190 7196
24. S. Shankar, Q. Chen, I. Siddiqui, K. Sarva, and R.K. Srivastava Sensitization of TRAIL-resistant LNCaP cells by resveratrol (3,4′,5 tri-hydroxystilbene): molecular mechanisms and therapeutic potential Journal of Molecular Signaling 2 2007 7
25. N. Shinohara, T. Tsuduki, J. Ito, T. Honma, R. Kijima, S. Sugawara, T. Arai, M. Yamasaki, A. Ikezaki, M. Yokoyama, K. Nishiyama, K. Nakagawa, T. Miyazawa, and I. Ikeda Jacaric acid, a linolenic acid isomer with a conjugated triene system, has a strong antitumor effect in vitro and in vivo Biochimica et Biophysica Acta 1821 2012 980 988
26. R. Siegel, D. Naishadham, and A. Jemal Cancer statistics, 2012 CA: A Cancer Journal for Clinicians 62 2012 10 29
27. I.H. Skjoth, and O.G. Issinger Profiling of signaling molecules in four different human prostate carcinoma cell lines before and after induction of apoptosis International Journal of Oncology 28 2006 217 229
28. R. Suzuki, R. Noguchi, T. Ota, M. Abe, K. Miyashita, and T. Kawada Cytotoxic effect of conjugated trienoic fatty acids on mouse tumor and human monocytic leukemia cells Lipids 36 2001 477 482
29. R. Suzuki, Y. Yasui, H. Kohno, S. Miyamoto, M. Hosokawa, K. Miyashita, and T. Tanaka Catalpa seed oil rich in 9t,11t,13c-conjugated linolenic acid suppresses the development of colonic aberrant crypt foci induced by azoxymethane in rats Oncology Reports 16 2006 989 996
30. T. Takagi, and Y. Itabashi Occurence of mixture of geometrical isomers of conjugated octadecatrienoic acids in some seed oils: analysis by open-tubular gas liquid chromatography and high performance liquid chromatography Lipids 16 1981 546 551
31. T. Tsuzuki, Y. Kawakami, R. Abe, K. Nakagawa, K. Koba, J. Imamura, T. Iwata, I. Ikeda, and T. Miyazawa Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid Journal of Nutrition 136 2006 2153 2159
32. T. Tsuzuki, Y. Tokuyama, M. Igarashi, K. Nakagawa, Y. Ohsaki, M. Komai, and T. Miyazawa Alpha-eleostearic acid (9Z,11E,13E-18:3) is quickly converted to conjugated linoleic acid (9Z,11E-18:2) in rats Journal of Nutrition 134 2004 2634 2639
33. C. Voelkel-Johnson, D.L. King, and J.S. Norris Resistance of prostate cancer cells to soluble TNF-related apoptosis-inducing ligand (TRAIL/Apo2L) can be overcome by doxorubicin or adenoviral delivery of full-length TRAIL Cancer Gene Therapy 9 2002 164 172
34. B. Yang, and H. Kallio Analysis of triacylglycerols of seeds and berries of sea buckthorn (Hippophae rhamnoides) of different origins by mass spectrometry and tandem mass spectrometry Lipids 41 2006 381 392
35. Y. Yasui, M. Hosokawa, H. Kohno, T. Tanaka, and K. Miyashita Growth inhibition and apoptosis induction by all-trans-conjugated linolenic acids on human colon cancer cells Anticancer Research 26 2006 1855 1860
36. Y. Yasui, M. Hosokawa, H. Kohno, T. Tanaka, and K. Miyashita Troglitazone and 9-cis, 11-trans, 13-trans-conjugated linolenic acid: comparison of their antiproliferative and apoptosis-inducing effects on different colon cancer cell lines Chemotherapy 52 2006 220 225
37. Y. Yasui, M. Hosokawa, T. Sahara, R. Suzuki, S. Ohgiya, H. Kohno, T. Tanaka, and K. Miyashita Bitter gourd seed fatty acid rich in 9c,11t,13t-conjugated linolenic acid induces apoptosis and up-regulates the GADD45, p53 and PPARγ in human colon cancer Caco-2 cells Prostaglandins, Leukotrienes and Essential Fatty Acids 73 2005 113 119
38. G.F. Yuan, J.Q. Yuan, and D. Li Punicic acid from Trichosanthes kirilowii seed oil is rapidly metabolized to conjugated linoleic acid in rats Journal of Medicinal Food 12 2009 416 422
39. J.H. Zar Biostatistical Analysis 4th ed. 1999 Prentice-Hall NJ