Cycloartanes from Krameria pauciflora and their in vitro PLA COX-1, and COX-2 enzyme inhibitory activities

Planta Medica

Volumn 78, Issue 18, 2012, Pages 1942-1948

  Ramírez Cisneros, M Ángeles ^a   Rios, María Yolanda ^a   Ríos Gómez, Ramiro ^b   Aguilar Guadarrama, A Berenice ^a  

^a CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

COX 2; cycloartanes; cyclomargenol; Krameria pauciflora; Krameriaceae; PLACOX 1

Indexed keywords

CYCLOMARGENOL; CYCLOMARGENONE; CYCLOMARGENYL 3 O BETA CAFFEOYL ESTER; CYCLOMARGENYL 3 O BETA COUMAROYL ESTER; CYCLOMARGENYL 3 O BETA FERULOYL ESTER; CYCLOOXYGENASE 1; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; DICHLOROMETHANE; INDOMETACIN; KRAMERIA PAUCIFLORA EXTRACT; PHOSPHOLIPASE A2; PHOSPHOLIPASE A2 INHIBITOR; PLANT EXTRACT; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHEMOPROPHYLAXIS; ELECTROSPRAY MASS SPECTROMETRY; ENZYME INHIBITION; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; IN VITRO STUDY; KRAMERIA PAUCIFLORA; KRAMERIACEAE; NONHUMAN; PLANT ROOT; PROSTAGLANDIN SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

CAFFEIC ACIDS; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; KRAMERIACEAE; MEDICINE, TRADITIONAL; MEXICO; MOLECULAR STRUCTURE; PHOSPHOLIPASES A2; PLANT EXTRACTS; PLANT ROOTS; TRITERPENES;

KRAMERIA; KRAMERIA LAPPACEA; KRAMERIA PAUCIFLORA; KRAMERIACEAE;

EID: 84871610081     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0032-1327882     Document Type: Article

References (33)

1. Bombardelli E., Morazzoni P., Cristoni A., Seghizzi R. Pharmaceutical and cosmetic formulations with antimicrobial activity. US Patent 6475536; 2002.
2. Silva S. A., De Castro J. C., Da Silva T. G., Da-Cunha E. V., Barbosa-Filho J. M., Da Silva M. S. Kramentosan, a new trinorlignan from the roots of Krameria tomentosa. Nat Prod Lett: 2001; 15 323 329 (Pubitemid 34071170)
3. Achenbach H., Utz W., Domínguez X. A. Neolignans and nor -neolignans from Krameria paucifolia. Phytochemistry: 1993; 34 835 837 (Pubitemid 2006019)
4. Achenbach H., Utz W., Sanchez H., Guajardo T. EM, Verde J., Domínguez X. A. Neolignans, nor -neolignans and other compounds from roots of Krameria grayi. Phytochemistry: 1995; 39 413 415
5. Achenbach H., Utz W., Lozano B., Guajardo T. EM, Moreno S. Lignans and neolignans from Krameria parvifolia. Phytochemistry: 1996; 43 1093 1095 (Pubitemid 27091476)
6. Rios M. Y., Aguilar-Guadarrama A. B. Nitrogen-containing phorbol esters from Croton ciliatoglandulifer and their effects on cyclooxygenases-1 and 2. J Nat Prod: 2006; 69 887 890 (Pubitemid 44166260)
7. Aguilar-Guadarrama A. B., Rios M. Y. Tree new sesquiterpenes from Croton arboreus. J Nat Prod: 2004; 67 914 917 (Pubitemid 38702760)
8. Maldonado E., Díaz-Arumir H., Toscano R. A., Martínez M. Lupane triterpenes with a δ -lactone at ring E, from Lippia mexicana. J Nat Prod: 2010; 73 1969 1972
9. Kikuchi T., Akihisa T., Tokuda H., Ukiya M., Watanabe K., Nishino H. Cancer chemopreventive effects of cycloartane-type and related triterpenoids in in vitro and in vivo models. J Nat Prod: 2007; 70 918 922 (Pubitemid 47056102)
10. Ageta H., Arai Y. Fern constituents: New cycloartane triterpenoids, (24 R)-cyclolaudenyl acetate and (24 R)-cyclomargenyl acetate, and their corresponding alcohols and ketones, isolated from Polypodium formosanum. Chem Lett: 1982; 11 881 884
11. Ageta H., Arai Y. Fern constituents: Cycloartane triterpenoids and allied compounds from Polypodium formosanum and P. niponicum. Phytochemistry: 1984; 23 2875 2884
12. Arai Y., Yamaide M., Yamazaky S., Ageta H. Fern constituents: Triterpenoids isolated from Polypodium vulgare, P. fauriei and P. virginianum. Phytochemistry: 1991; 30 3369 3377
13. 25-double bond from Polypodium formosanum. Phytochemistry: 1992; 31 1353 1357
14. Akihisa T., Kimura Y., Roy K., Ghosh P., Thakur S., Tamura T. Triterpene alcohols and 3-oxo steroids of nine leguminosae seeds. Phytochemistry: 1994; 35 1309 1313 (Pubitemid 2065958)
15. Banskota A. H., Tezuka Y., Tran K. Q., Tanaka K., Saiki I., Kadota S. Thirteen novel cycloartane-type triterpenes from Combretum quadrangulare. J Nat Prod: 2000; 63 57 64 (Pubitemid 30078771)
16. Chen Y. H., Chang F. R., Lu M. C., Hsieh P. W., Wu M. J., Du Y. C., Wu Y. C. New benzoyl glucosides and cytotoxic pterosin sesquiterpenes from Pteris ensiformis Burm. Molecules: 2008; 13 255 266
17. Luo H. F., Li Q., Yu S., Badger T. M., Fang N. Cytotoxic hydroxylated triterpene alcohol ferulates from rice bran. J Nat Prod: 2005; 68 94 97 (Pubitemid 40175938)
18. Shen T., Yuan H. Q., Wan W. Z., Wang X. L., Wang X. N., Ji M., Lou H. X. Cycloartane triterpenoids from the resinous exudates of Comniphora opobalsamum. J Nat Prod: 2008; 71 81 86 (Pubitemid 351236401)
19. Zhang H. J., Tan T. G., Hoang D. V., Hung N. V., Cuong N. M., Soejarto D. D., Petuzzo J. M., Fong H. HS. Natural anti-HIV agents. Part IV. Anti-HIV constiuents from Vatica cinerea. J Nat Prod: 2003; 66 263 268 (Pubitemid 36278242)
20. Ju J. H., Liu D., Lin G., Zhang Y. M., Yang J. S., Lu Y., Gong N. B., Zheng Q. T. Beesiosides G, H, and J-N, seven new cycloartane triterpene glycosides from Beesia calthifolia. J Nat Prod: 2002; 65 147 152 (Pubitemid 34171172)
21. Yan Y. X., Hu X. D., Chen J. C., Sun Y., Zhang X. M., Qing C., Qiu M. H. Cytotoxic triterpenoid alkaloids from Buxus microphylla. J Nat Prod: 2009; 72 308 311
22. Yokosuda A., Sato K., Yamori T., Mimaki Y. Triterpene glycosides from Curligo orchioides and their cytotoxic activity. J Nat Prod: 2010; 73 1102 1106
23. Fu X., Li X. C., Smillie T. J., Carvahlo P., Mabusela W., Syce J., Johnson Q., Folk W., Avery M. A., Khan I. A. Cycloartane glycosides from Sutherlandia frutescens. J Nat Prod: 2008; 71 1749 1753
24. Shiao Y. J., Chen W. P., Lin Y. L. New poliphenols and triterpene from the pseudobulbs of Pleione formosana. J Chin Chem Soc: 2009; 56 828 833
25. Ahmad V. U., Atta-ur-Rahman A. Handbook of natural products data: pentacyclic triterpenoids. Amsterdam Elsevier: 1994; 76
26. Hirohara M., Yasuoka Y., Arai Y., Shiojima K., Ageta H., Chang H. C. Triterpenoids from the fern Goniophlebium mengtzeense. Phytochemistry: 1997; 45 1023 1029 (Pubitemid 27265694)
27. Achenbach H., Utz W., Usubillaga A., Rodriguez H. A. Lignans from Krameria ixina. Phytochemistry: 1991; 30 3753 3757
28. Achenbach H., Grob J., Dominguez X. A., Verde S. J., Salgado F. Ramosissin and other methoxylated nor-neolignans from Krameria ramosissima. Phytochemistry: 1987; 26 2041 2043
29. Akihisa T., Yasukawa K., Yamaura M., Ukiya M., Kimura Y., Shimizu N., Arai K. Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects. J Agric Food Chem: 2000; 48 2313 2319 (Pubitemid 30431233)
30. Aquila S., Rojano B., Recio M. C., Giner R. M., Schinella G. R., Debenedetti S. L., Saez J., Ríos J. L. Anti-inflammatory activity of berenjenol and related compounds. Planta Med: 2009; 75 18 23
31. Du Q., Chen Z., Zhou L. F., Zhang Q., Huang M., Yin K. S. Inhibitory effects of astragaloside IV on ovalbumin-induced chronic experimental asthma. Can J Physiol Pharmacol: 2008; 86 449 457 (Pubitemid 351948684)
32. Vitor C. E., Figueiredo C. P., Hara D. B., Bento A. F., Mazzuco T. L., Calixto J. B. Therapeutic action and underlying mechanisms of a combination of two pentacyclic triterpenes, α - and β -amyrin, in a mouse model of colitis. Br J Pharmacol: 2009; 157 1034 1044
33. Yasukawa K., Akihisa T., Kimura Y., Tamura T., Takido M. Inhibitory effect of cycloartenol ferulate, a component of rice bran, on tumor promotion in two-stages carcinogenesis in mouse skin. Biol Pharm Bull: 1998; 21 1072 1076 (Pubitemid 28513985)