Biflavonoids from caper (Capparis spinosa L.) Fruits and their effects in inhibiting NF-kappa B activation

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 7, 2011, Pages 3060-3065

  Zhou, Hai Feng ^a   Xie, Chenghui ^b   Jian, Renji ^a   Kang, Jie ^b   Li, Yan ^a   Zhuang, Chang Long ^a   Yang, Fang ^a   Zhang, Le Le ^a   Lai, Long ^a   Wu, Tong ^a   Wu, Xianli ^b  

^a SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY   (China)

^b UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE PHOSPHATASE; ANTI-INFLAMMATORY EFFECTS; CHEMICAL STRUCTURE; DOSE RESPONSE; GINKGETIN; IN-VIVO; INHIBITORY EFFECT; MEDITERRANEAN BASIN; NORTHWEST CHINA; NUCLEAR FACTOR KAPPAB; REPORTER ASSAY; SAKURANETIN;

ALKALINITY; FRUITS; PHOSPHATASES; SPECTROSCOPIC ANALYSIS; TRANSCRIPTION FACTORS;

FORESTRY;

ANTIINFLAMMATORY AGENT; BIFLAVONOID; FLAVONOID; GINKGETIN; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; ISOGINKGETIN; SAKURANETIN;

CAPPARIS; CHEMISTRY; CHINA; CONFERENCE PAPER; DOSE RESPONSE; DRUG ANTAGONISM; FRUIT; ISOLATION AND PURIFICATION;

ANTI-INFLAMMATORY AGENTS; BIFLAVONOIDS; CAPPARIS; CHINA; DOSE-RESPONSE RELATIONSHIP, DRUG; FLAVONOIDS; FRUIT; NF-KAPPA B;

CAPPARACEAE; CAPPARIS SPINOSA;

EID: 79953848184     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf105017j     Document Type: Article

References (31)

1. Tlili, N.; Elfalleh, W.; Saadaoui, E.; Khaldi, A.; Triki, S.; Nasri, N. The caper (Capparis L.): Ethnopharmacology, phytochemical and pharmacological properties Fitoterapia 2010, 82, 93-101
2. Tesoriere, L.; Butera, D.; Gentile, C.; Livrea, M. A. Bioactive components of caper (Capparis spinosa L.) from Sicily and antioxidant effects in a red meat simulated gastric digestion J. Agric. Food Chem. 2007, 55, 8465-8471 (Pubitemid 350013089)
3. Ageel, A. M.; Parmar, N. S.; Mossa, J. S.; Al-Yahya, M. A.; Al-Said, M. S.; Tariq, M. Anti-inflammatory activity of some Saudi Arabian medicinal plants Agents Actions 1986, 17, 383-384 (Pubitemid 16137160)
4. al-Said, M. S.; Abdelsattar, E. A.; Khalifa, S. I.; el-Feraly, F. S. Isolation and identification of an anti-inflammatory principle from Capparis spinosa Pharmazie 1988, 43, 640-641
5. Rimbau, V.; Risco, E.; Canigueral, S. R.; Iglesias, J. Antiinflammatory activity of some extracts from plants used in the traditional medicine of North-African countries Phytother. Res. 1996, 10, 421-423 (Pubitemid 26252792)
6. Zhou, H.; Jian, R.; Kang, J.; Huang, X.; Li, Y.; Zhuang, C.; Yang, F.; Zhang, L.; Fan, X.; Wu, T.; Wu, X. Anti-inflammatory effects of caper (Capparis spinosa L.) fruit aqueous extract and the isolation of main phytochemicals J. Agric. Food Chem. 2010, 58, 12717-12721
7. Choi, D. Y.; Lee, J. Y.; Kim, M. R.; Woo, E. R.; Kim, Y. G.; Kang, K. W. Chrysoeriol potently inhibits the induction of nitric oxide synthase by blocking AP-1 activation J. Biomed. Sci. 2005, 12, 949-959
8. Hamalainen, M.; Nieminen, R.; Vuorela, P.; Heinonen, M.; Moilanen, E. Anti-inflammatory effects of flavonoids: genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and NF-kappaB activations, whereas flavone, isorhamnetin, naringenin, and pelargonidin inhibit only NF-kappaB activation along with their inhibitory effect on iNOS expression and NO production in activated macrophages Mediators Inflammation 2007, 2007, 45673
9. Nicholas, C.; Batra, S.; Vargo, M. A.; Voss, O. H.; Gavrilin, M. A.; Wewers, M. D.; Guttridge, D. C.; Grotewold, E.; Doseff, A. I. Apigenin blocks lipopolysaccharide-induced lethality in vivo and proinflammatory cytokines expression by inactivating NF-kappaB through the suppression of p65 phosphorylation J. Immunol. 2007, 179, 7121-7127
10. Bremner, P.; Heinrich, M. Natural products as targeted modulators of the nuclear factor-kappaB pathway J. Pharm. Pharmacol. 2002, 54, 453-472 (Pubitemid 34308488)
11. Wan, F.; Lenardo, M. J. The nuclear signaling of NF-kappaB: Current knowledge, new insights, and future perspectives Cell Res. 2010, 20, 24-33
12. Van der Heiden, K.; Cuhlmann, S.; Luong le, A.; Zakkar, M.; Evans, P. C. Role of nuclear factor kappaB in cardiovascular health and disease Clin. Sci. (Lond). 2010, 118, 593-605
13. Sarkar, F. H.; Li, Y. NF-kappaB: a potential target for cancer chemoprevention and therapy Front. Biosci. 2008, 13, 2950-2959 (Pubitemid 351589211)
14. Baker, W.; Finch, A. C. M.; Ollis, W. D.; Robinson, K. W. Biflavonyls, a new class of natural product. The structures of ginkgetin, isoginkgetin, and sciadopitysin Proc. Chem. Soc. 1959, 91-92
15. Konda, Y.; Sasaki, T.; Kagawa, H.; Takayanagi, H.; Harigaya, Y.; Sun, X.-L.; Li, X.; Onda, M. Conformational analysis of C3′-C8 connected biflavones J. Heterocycl. Chem. 1995, 32, 1531-1535
16. Markham, K. R.; Sheppard, C.; Geiger, H. 13C NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids Phytochemistry 1987, 26, 3335-3337
17. Kemertelidze, E. P.; Syrov, V. N.; Alaniya, M. D.; Kavtaradze, N. S.; Khushbaktova, Z. A. Chemical composition and pharmacological activity of the leaves of Pueraria hirsuta L. grown in Georgia Pharm. Chem. J. 2008, 42, 340-343
18. Markham, K. R.; Ternai, B.; Stanley, R.; Geiger, H.; Mabry, T. J. Carbon-13 NMR studies of flavonoids-III: Naturally occurring flavonoid glycosides and their acylated derivatives Tetrahedron 1978, 34, 1389-1397
19. Oliveira, D.; Wanderley, G.; Mesquita, A. A. L.; Kubitzki, K.; Gottlieb, O. R. The chemistry of the Brazilian Guttiferae. Part 39. Xanthones from Bonnetia dinizii Phytochemistry 1990, 29, 1893-1894
20. Ibrahim, A.-R. S.; Galal, A. M.; Ahmed, M. S.; Mossa, G. S. O-Demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans Chem Pharm Bull. 2003, 51, 203-206 (Pubitemid 41701995)
21. Brasier, A. R. The NF-kappaB regulatory network Cardiovasc. Toxicol. 2006, 6, 111-130
22. Hoffmann, A.; Natoli, G.; Ghosh, G. Transcriptional regulation via the NF-kappaB signaling module Oncogene 2006, 25, 6706-6716 (Pubitemid 44657847)
23. O'Sullivan, B.; Thompson, A.; Thomas, R. NF-kappa B as a therapeutic target in autoimmune disease Expert Opin. Ther. Targets 2007, 11, 111-22 (Pubitemid 46188808)
24. Yates, L. L.; Gorecki, D. C. The nuclear factor-kappaB (NF-kappaB): from a versatile transcription factor to a ubiquitous therapeutic target Acta Biochim. Pol. 2006, 53, 651-662 (Pubitemid 46090115)
25. Singh, B.; Kaur, P.; Gopichand; Singh, R. D.; Ahuja, P. S. Biology and chemistry of Ginkgo biloba Fitoterapia. 2008, 79, 401-418
26. Kim, H. P.; Park, H.; Son, K. H.; Chang, H. W.; Kang, S. S. Biochemical pharmacology of biflavonoids: implications for anti-inflammatory action Arch. Pharmacal Res. 2008, 31, 265-273
27. Kim, H. P.; Pham, H. T.; Ziboh, V. A. Flavonoids differentially inhibit guinea pig epidermal cytosolic phospholipase A2 Prostaglandins, Leukotrienes Essent. Fatty Acids 2001, 65, 281-286 (Pubitemid 34258926)
28. Kwak, W. J.; Han, C. K.; Son, K. H.; Chang, H. W.; Kang, S. S.; Park, B. K.; Kim, H. P. Effects of ginkgetin from Ginkgo biloba leaves on cyclooxygenases and in vivo skin inflammation Planta Med. 2002, 68, 316-321
29. Park, Y. M.; Won, J. H.; Yun, K. J.; Ryu, J. H.; Han, Y. N.; Choi, S. K.; Lee, K. T. Preventive effect of Ginkgo biloba extract (GBB) on the lipopolysaccharide-induced expressions of inducible nitric oxide synthase and cyclooxygenase-2 via suppression of nuclear factor-kappaB in RAW 264.7 cells Biol. Pharm. Bull. 2006, 29, 985-990
30. Chen, J. W.; Chen, Y. H.; Lin, F. Y.; Chen, Y. L.; Lin, S. J. Ginkgo biloba extract inhibits tumor necrosis factor-alpha-induced reactive oxygen species generation, transcription factor activation, and cell adhesion molecule expression in human aortic endothelial cells Arterioscler., Thromb., Vasc. Biol. 2003, 23, 1559-1566
31. Inocencio, C.; Rivera, D.; Alcaraz, F.; Tomas-Barberan, F. A. Flavonoid content of commercial capers (Capparis spinosa, C. sicula and C. orientalis) produced in Mediterranean countries Eur. Food Res. Technol. 2000, 212, 70-74