Anti-inflammatory 5-(11′Z-heptadecenyl)- and 5-(8′Z,11′Z-heptadecadienyl)-resorcinols from mango (Mangifera indica L.) peels

Phytochemistry

Volumn 69, Issue 4, 2008, Pages 988-993

  Knödler, Matthias ^a   Conrad, Jürgen ^a   Wenzig, Eva M ^b   Bauer, Rudolf ^b   Lacorn, Markus ^a   Beifuss, Uwe ^a   Carle, Reinhold ^a   Schieber, Andreas ^a  

^a UNIVERSITY OF HOHENHEIM   (Germany)

^b UNIVERSITY OF GRAZ   (Austria)

Author keywords

5 (11 Z Heptadecenyl) resorcinol; 5 Lipoxygenase; Anacardiaceae; Cyclooxygenase; Mangifera indica L.; MS; NMR

Indexed keywords

5 (11'Z HEPTADECENYL)RESORCINOL; 5 (8'Z,11'Z HEPTADECADIENYL)RESORCINOL; 5-(11'Z-HEPTADECENYL)RESORCINOL; 5-(8'Z,11'Z-HEPTADECADIENYL)RESORCINOL; ANTIINFLAMMATORY AGENT; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; LEUKOTRIENE; LEUKOTRIENE RECEPTOR BLOCKING AGENT; PLANT EXTRACT; PROSTAGLANDIN SYNTHASE INHIBITOR; RESORCINOL; RESORCINOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MANGO; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANTI-INFLAMMATORY AGENTS; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; LEUKOTRIENE ANTAGONISTS; LEUKOTRIENES; MAGNETIC RESONANCE SPECTROSCOPY; MANGIFERA; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PLANT EXTRACTS; RESORCINOLS;

ANACARDIACEAE; MANGIFERA INDICA;

EID: 39149129350     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.10.013     Document Type: Article

References (26)

1. Adams M., Kunert O., Haslinger E., and Bauer R. Inhibition of leukotriene biosynthesis by quinolone alkaloids from the fruits of Evodia rutaecarpa. Planta Med. 70 (2004) 904-908
2. Bandyopadhyay C., Gholap A.S., and Mamdapur V.R. Characterization of alkylresorcinol in mango (Mangifera indica L.) latex. J. Agric. Food Chem. 33 (1985) 377-379
3. Bouillant M.L., Jacoud C., Zanella I., Favre-Bonvin J., and Bally R. Identification of 5-(12-heptadecenyl)-resorcinol in rice root exudates. Phytochemistry 35 (1994) 769-771
4. Bradley S.A., and Krishnamurthy K. A modified CRISES-HSQC for band-selective IMPRESS. Magn. Reson. Chem. 43 (2005) 117-123
5. Calanni F., and Laufer S. Biochemistry and mediators of inflammation. In: Laufer S., Gay S., and Brune K. (Eds). Inflammation and Rheumatic Diseases. The Molecular Basis of Novel Therapies (2003), Georg Thieme Verlag, Stuttgart, Germany 15-57
6. Cojocaru M., Droby S., Glotterer E., Goldman A., Gottlieb H.E., Jacoby B., and Prusky D. 5-(12)-Heptadecenylresorcinol, the major component of the antifungal activity in the peel of mango fruit. Phytochemistry 25 (1986) 1093-1095
7. Crouch R., Boyer R.D., Johnson R., and Krishnamurthy K. Broadband and band-selective IMPRESS-gHMBC: compensation of refocusing inefficiency with synchronized inversion sweep. Magn. Reson. Chem. 42 (2004) 301-307
8. Droby S., Prusky D., Jacoby B., and Goldman A. Presence of antifungal compounds in the peel of mango fruits and their relation to latent infections of Alternaria alternata. Physiol. Plant Pathol. 29 (1986) 173-183
9. Fiebich B.L., Grozdeva M., Hess S., Hüll M., Danesch U., Bodensieck A., and Bauer R. Petasites hybridus extracts in vitro inhibit COX-2 and PGE2 release by direct interaction with the enzyme and by preventing p42/44 MAP kinase activation in rat primary microglial cells. Planta Med. 71 (2005) 12-19
10. Gonzales M.J.G., DeOliveira C.J.C., Fernandes J.O., Kijjoa A., and Herz W. Further alkyl and alkenylphenols of Knema laurina and Knema austrosiamensis: location of the double bond in the alkenyl side chains. Phytochemistry 43 (1996) 1333-1337
11. Hershko K., Weinberg I., and Ingber A. Exploring the mango - poison ivy connection: the riddle of discriminative plant dermatitis. Contact Dermatitis 52 (2005) 3-5
12. Jin W., and Zjawiony J.K. 5-Alkylresorcinols from Merulius incarnatus. J. Nat. Prod. 69 (2006) 704-706
13. Khare C.P. Indian Herbal Remedies (2004), Springer Verlag, Berlin, Heidelberg pp. 300-303
14. Knödler M., Berardini N., Kammerer D.R., Carle R., and Schieber A. Characterization of major and minor alk(en)ylresorcinols from mango (Mangifera indica L.) peels by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry. Rapid Commun. Mass Spectrom. 21 (2007) 945-951
15. Kozubek A., and Tyman J.H.P. Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biological activity. Chem Rev. 99 (1999) 1-25
16. Kozubek A., and Tyman J.H.P. Bioactive phenolic lipids. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry vol. 30 (2005), Elsevier, Amsterdam 111-190
17. Mattia C., and Coluzzi F. COX-2 inhibitors: pharmacological data and adverse effects. Minerva Anestesiol. 71 (2005) 461-470
18. Mukherjee D., Nissen S.E., and Topol E.J. Risk of cardiovascular events associated with selective COX-2 inhibitors. J. Am. Med. Assoc. 286 (2001) 954-959
19. CH. J. Am. Chem. Soc. 127 (2005) 6154-6155
20. Oka K., Saito F., Yasuhara T., and Sugimoto A. A study of cross-reactions between mango contact allergens and urushiol. Contact Dermatitis 51 (2004) 292-296
21. Paprikka K., Rowland I.R., Welch R.W., and Wähälä K. In vitro antioxidant activity and antigenotoxicity of 5-n-alkylresorcinols. J. Agric. Food Chem. 54 (2006) 1646-1650
22. Reininger E.A., and Bauer R. Prosaglandin-H-synthase (PGHS)-1 and -2 microtiter assays for the testing of herbal drugs and in vitro inhibition of PGHS-isoenzyms by polyunsaturated fatty acids from Platycodi radix. Phytomedicine 13 (2006) 164-169
23. Ross A.B., Kamal-Eldin A., and Ǻman P. Dietary alkyresorcinols: absorption, bioactivities, and possible use as biomarkers of whole-grain wheat- and rye-rich foods. Nutr. Rev. 62 (2004) 81-95
24. Scribe P., Guezennec J., Dagat J., Pepe C., and Saliot A. Identification of the position and the stereochemistry of the double bond in monounsaturated fatty acid methyl esters by gas chromatography/mass spectrometry of dimethyl disulfide derivatives. Anal. Chem. 60 (1988) 928-931
25. Valcic S., Wächter G.A., Eppler C.M., and Timmermann B.N. Nematicidal alkylene resorcinols from Lithraea molleoides. J. Nat. Prod. 65 (2002) 1270-1273
26. Wagner H., Breu W., Willer F., Wierer M., and Remiger P. In vitro inhibition of arachidonate metabolism by some alkamides and prenylated phenols. Planta Med. 55 (1989) 566-567