Phenolic compounds from Bursera simaruba Sarg. bark: Phytochemical investigation and quantitative analysis by tandem mass spectrometry

Phytochemistry

Volumn 70, Issue 5, 2009, Pages 641-649

  Maldini, Mariateresa ^a   Montoro, Paola ^a   Piacente, Sonia ^a   Pizza, Cosimo ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

Bursera simaruba; LC ESI MS MS; Lignans; NMR; Phenolic compounds

Indexed keywords

PHENOL DERIVATIVE;

ARTICLE; BARK; BURSERACEAE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TANDEM MASS SPECTROMETRY; VALIDATION STUDY;

BURSERACEAE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHENOLS; PLANT BARK; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; TANDEM MASS SPECTROMETRY;

BURSERA SIMARUBA; BURSERACEAE;

EID: 64949185942     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.02.009     Document Type: Article

References (44)

1. Abad M.J., Bermejo P., Carretero E., Martinez-Acitores C., Noguera B., and Villar A. Anti-inflammatory activity of some medicinal plant extracts form Venezuela. J. Ethnopharmacol. 55 (1996) 63-68
2. Arvigo R., and Balik M. Bursera simaruba. In: Arvigo R., and Balik M. (Eds). Rainforest Remedies. One Hundred Healing Herbs of Belize. second ed. (1993), Lotus Press, Twin Lakes, WI 118-119
3. Badillo V.M., Schnee L., and Benitez d.R.C. Clave de las Familias de Plantas Superiores de Venezuela. seventh ed. (1985), Espasande, Caracas, Venezuela
4. Bianchi E., Caldwell M.E., and Cole J.R. Antitumor agents from Bursera microphylla (Burseraceae) I. Isolation and characterization of deoxypodophyllotoxin. J. Pharm. Sci. 57 (1968) 696-697
5. Borges-Argaez R., Escalante-Erosa F., May-Pat F., Medina-Baizabal L., Ojeda-Uc Y., Peraza-Sànchez S.R., Perez-Rodriguez M., Salazar-Aguilar N.E., Sima-Polanco P., and Peňa-Rodrìguez L.M. Bioactive metabolites from Yucatecan medicinal plants. In: Shahidi F., and Ho C.T. (Eds). Phytochemicals and Phytopharmaceuticals (2000), AOCS press, Champaign 332-341
6. Borsato M.L.C., Grael C.F.F., Souza G.E.P., and Lopes N.P. Analgesic activity of the lignans from Lychnophora ericoides. Phytochemistry 55 (2000) 809-813
7. Broomhead A.J., and Dewick P.M. Aryltetralin lignans from Linum flavum and Linum capitatum. Phytochemistry 29 (1990) 3839-3844
8. Broomhead A.J., and Dewick P.M. Tumor-inhibitory aryltetralin lignans in Podophyllum versipelle, Diphylleia cymosa and Diphylleia grayi. Phytochemistry 29 (1990) 3831-3837
9. Carletti A., Emmenegger H., and Stahelin H. Antimitotic properties of substances derived from podophyllotoxin. Actual. Pharmacol. 12 (1959) 103-128
10. Carretero M.E., Lòpez-Perez J.L., Abad M.J., Bermejo P., Tillet S., Israel A., and Noguera-P B. Preliminary study of the anti-inflammatory activity of hexane extract and fractions from Bursera simaruba (Linneo) Sarg. (Burseraceae) leaves. J. Ethnopharmacol. 116 (2008) 11-15
11. Chao Y.Y., Chen I.S., Yeh J.L., Chen J.J., Ko Y.C., Lu Y.C., Su W., Chen W.C., and Jan C.R. Effect of lignans isolated from Hernandia nymphaeifolia on estrogenic compounds-induced calcium mobilization in human neutrophils. Life Sci. 70 (2002) 3109-3121
12. 2+ signaling in renal tubular cells. Eur. J. Pharmacol. 443 (2002) 31-38
13. Chen J., Chang Y.L., Teng C.M., and Chen I.S. Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia. Planta Med. 66 (2000) 251-256
14. Chosson E., Chaboud A., Chulia A.J., and Raynaud J. A phloracetophenone glucoside from Rhododendron ferrugineum. Phytochemistry 47 (1997) 87-88
15. Ciccio J.F., and Rosales K.M. Isolation of the lignan yatein from bark of Bursera simaruba (Burseraceae). Ing. Cien. Quim. 15 (1995) 20-21
16. Culioli G., Mathe C., Archier P., and Vieillescazes C. A lupane triterpene from frankincense (Boswellia sp., Burseraceae). Phytochemistry 62 (2003) 537-541
17. Estévez-Braun A., Estévez-Reyes R., and Gonzàlez A.G. 13C NMR assignments of some dibenzyl-γ-butyrolactone lignans. Phytochemistry 43 (1996) 885-886
18. Gu J., Park E.J., Totura S., Riswan S., Fong H.H.S., Pezzuto J.M., and Kinghorn A.D. Constituents of the Twigs of Hernandia ovigera that Inhibit the transformation of JB6 murine epidermal cells. J. Nat. Prod. 65 (2002) 1065-1068
19. Horowitz R.M., and Gentili B. Flavonoids of citrus VI. Structure of neohesperidose. Tetrahedron 19 (1963) 773-782
20. Ichikawa K., Kinoshita T., Nishibe S., and Sankawa U. The calcium-antagonist activity of lignans. Chem. Pharm. Bull. 34 (1986) 3514-3517
21. Ikeda R., Nagao T., Okabe H., Nakano Y., Matsunaga H., Katano M., and Mori M. Antiproliferative constituents in Umbelliferae plants. IV. Constituents in the fruits of Anthriscus sylvestris Hoffm. Chem. Pharm. Bull. 46 (1998) 875-878
22. International Conferences on Harmonization (ICH), 1995. Note for guidance on validation of analytical procedures: text and methodology, Q2 (R1), 1995. .
23. Jang D.S., Cuendet M., Su B.N., Totura S., Riswan S., Fong H.H.S., Pezzuto J.M., and Kinghorn A.D. Constituents of the seeds of Hernandia ovigera with inhibitory activity against cyclooxygenase-2. Planta Med. 70 (2004) 893-896
24. Jeong G., Kwon O.K., Park B.Y., Oh S.R., Ahn K.S., Chang M.J., Oh W.K., Kim J.C., Byung-Sun M., Youn-Chul K., and Hyeong-Kyu L. Lignans and coumarins from the roots of Anthriscus sylvestris and their increase of caspase-3 activity in HL-60 cells. Biol. Pharm. Bull. 30 (2007) 1340-1343
25. Jolad S.D., Wiedhopf R.M., and Cole J.R. Cytotoxic agents from Bursera klugii (Burseraceae) I: isolation of sapelins A and B. J. Pharm. Sci. 66 (1977) 889-890
26. Jolad S.D., Wiedhopf R.M., and Cole J.R. Cytotoxic agents from Bursera morelensis (Burseraceae): deoxypodophyllotoxin and a lignan, 5′-desmethoxydeoxypodophyllotoxin. J. Pharm. Sci. 66 (1977) 892-893
27. Jutiviboonsuk A., Zhang H., Tan T.G., Ma C., Van Hung N., Cuong N.M., Bunyapraphatsara N., Soejarto D.D., and Fong H.H.S. Bioactive constituents from roots of Bursera tonkinensis. Phytochemistry 66 (2005) 2745-2751
28. Kiralj R., Ferriera M.M.C., Donate P.M., da Silva R., and Albuquerque S. Conformational study of (8α, 8′β)-bis(substituted phenyl)-lignano-9,9′-lactones by means of combined computational, database mining, NMR, and chemometric approaches. J. Phys. Chem. A 111 (2007) 6316-6333
29. Kitts D.D., Yuan Y.V., Wijewickreme A.N., and Thompson L.U. Antioxidant activity of the flaxseed lignan secoisolariciresinol diglycoside and its mammalian lignan metabolites enterodiol and enterolactone. Mol. Cell. Biochem. 202 (1999) 91-100
30. Kuo Y., Kuo Y.H., Lin Y.L., and Tsai W.J. Yatein from Chamaecyparis obtusa suppresses herpes simplex virus type 1 replication in HeLa cells by interruption the immediate-early gene expression. Antiviral Res. 70 (2006) 299-311
31. Lima L.M., Perazzo F.F., Carvalho J.C.T., and Bastos J.K. Anti-inflammatory and analgesic activities of the ethanolic extracts from Zanthoxylum riedelianum (Rutaceae) leaves and stem bark. J. Pharm. Pharmacol. 59 (2007) 1151-1158
32. Markkanen T., Makinen M.L., Maunuksela E., and Himanen P. Podophyllotoxin lignans under experimental antiviral research. Drugs Exp. Clin. Res. 7 (1981) 711-718
33. Nakanishi T., Inatomi Y., Murata H., Shigeta K., Iida N., Inada A., Murata J., Farrera M.A.P., Iinuma M., Tanaka T., Tajima S., and Oku N. A and known cytotoxic aryltetralin-type lignans from stems of Bursera graveolens. Chem. Pharm. Bull. 53 (2005) 229-231
34. Noguera B., Dìaz E., Garcìa M.V., San Feliciano A., Lòpez-Perez J.L., and Israel A. Anti-inflammatory activity of leaf extract and fractions of Bursera simaruba (L.) Sarg. (Burseraceae). J. Ethnopharmacol. 92 (2004) 129-133
35. Peraza-Sànchez S.R., and Peňa-Rodrìguez L.M. Isolation of picropolygamain from the resin of Bursera simaruba. J. Nat. Prod. 55 (1992) 1768-1771
36. Peraza-Sànchez S.R., Salazar-Aguilar N.E., and Peňa-Rodrìguez L.M. A triterpene from the resin of Bursera simaruba. J. Nat. Prod. 58 (1995) 271-274
37. Rashid M.A., Gustafson K.R., Cardellina J.H., and Boyd M.R. A podophyllotoxin derivative from Bridelia ferruginea. Nat. Prod. Lett. 14 (2000) 285-292
38. Sosa S., Balick M.J., Arvigo R., Esposito R.G., Pizza C., Altinier G., and Tubaro A. Screening of the topical anti-inflammatory activity of some Central American plants. J. Ethnopharmacol. 81 (2002) 211-215
39. Syamasundar K.V., and Mallavarapu G.R. Two triterpenoid lactones from the resin of Bursera delpechiana. Phytochemistry 40 (1995) 337-339
40. von Wartburg A., Angliker E., and Renz J. Lignan glucosides from Podophyllum peltatum. Helv. Chim. Acta 40 (1957) 1331-1357
41. Wen C.C., Kuo Y.H., Jan J.T., Liang P.H., Wang S.Y., Liu H.G., Lee C.K., Chang S.T., Kuo C.J., Lee S.S., Hou C.C., Hsiao P.W., Chien S.C., Shyur L.F., and Yang N.S. Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus. J. Med. Chem. 50 (2007) 4087-4095
42. Wickramaratne D.B.M., Mar W., Chai H., Castillo J.J., Farnsworth N.R., Soejarto D.D., Cordell G.A., Pezzuto J.M., and Kinghorn A.D. Cytotoxic constituents of Bursera permollis. Planta Med. 61 (1995) 80-81
43. Yoshikawa K., Sugawara S., and Arihara S. Phenylpropanoids and other secondary metabolites from fresh fruits of Picrasma quassioides. Phytochemistry 40 (1995) 253-256
44. Źoelek T., Paradowska K., and Wawer I. 13C CP MAS NMR and GIAO-CHF calculations of coumarins. Solid State Nucl. Magn. Reson. 23 (2003) 77-87