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Lignans from the fruits of the red pepper (Capsicum annuum L.) and their antioxidant effects

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Abstract

The fruits of Capsicum annuum were extracted using 80% aqueous MeOH, and fractionated using EtOAc and water. Repeated column chromatography using silica gel, octadecyl silica gel, and Sephadex LH-20 for the EtOAc fraction led to the isolation of a new lignan glycoside and a known one, icariside E5. From the results of spectroscopic data, including EIMS, FABMS, UV, IR, 1H and 13C-NMR, DEPT, and 2D-NMR (COSY, HSQC, HMBC), the chemical structure of the new lignan glycoside was determined as (8R)-isodehydrodiconiferyl alcohol-4′-O-(6″-vanilloyl)-β-D-glucopyranoside named vanilloylicariside E5. All isolated compounds were tested for antioxidant activities using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Icariside E5 (2) and (8R)-Isodehydrodiconiferyl alcohol (3) exhibited a strong scavenging effect on DPPH (2: IC50=42.1 µM, 3: IC50=4.5 µM).

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References

  • Almela, L., Lopez-Roca, J. M., Candela, M. E., and Alcazar, M. D. Carotenoid composition of new cultivars of red pepper for paprika. J. Agric. Food Chem., 39, 1606–1609 (1991).

    Article  CAS  Google Scholar 

  • Beltran, J., Ghosh, A. K., and Basu, S. Immunotherapy of tumors with neuroimmune ligand capsaicin. J. Immunol., 178, 3260–3264 (2007).

    CAS  PubMed  Google Scholar 

  • Garces, C. A., Gil, O. R., Alvarez, F. A., and Arnedo, A. M. S. Inheritance of capsaicin and dihydrocapsaicin, determined by HPLC-ESI/MS in an intraspecific cross of Capsicum annuum L. J. Agric. Food Chem., 55, 6951–1956 (2007).

    Article  CAS  Google Scholar 

  • Gupta, R. S., Dixit, V. P., and Dobhal, M. P. Hypocholesterolaemic effect of the oleoresin of Capsicum annum L. in gerbils (Meriones hurrianae Jerdon). Phytother. Res., 16, 273–275 (2002).

    Article  CAS  PubMed  Google Scholar 

  • Higuchi, H., Fukui, K., Kinjo, J., and Nohara, T. Leguminous plants 29. Four new glycosides from Albizziae Cortex III. Chem. Pharm. Bull., 40, 534–345 (1992).

    CAS  Google Scholar 

  • Iorizzi, M., Lanzotti, V., De Marino, S., Zollo, F., Blanco, M. M., Macho, A., and Munoz, E. New glycosides from Capsicum annuum L. var. acuminatum. Isolation, structure determination, and biological activity. J. Agric. Food Chem., 49, 2022–2029 (2001).

    Article  CAS  PubMed  Google Scholar 

  • Izumitani, Y., Yahara, S., and Nohara, T. Novel acyclic diterpenes glycosides, capsianosides VI, G and H from Capsicum plants. Chem. Pharm. Bull., 38, 1299–1307 (1990).

    CAS  Google Scholar 

  • Mabel, S. M., Feng, X. T., Thomas, C. W. M., and Henry, N. C. W., On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton. Tetrahedron, 54, 12429–12444 (1998).

    Article  Google Scholar 

  • Maoka, T., Mochida, K., Kozuka, M., Ito, Y., Fujiwara, Y., Hashimoto, K., Enjo, F., Ogata, M., Nobukuni, Y., Tokuda, H., and Nishino, H. Cancer chemopreventive activity of carotenoids in the fruits of red paprika Capsicum annuum L. Cancer Lett., 172, 103–109 (2001).

    Article  CAS  PubMed  Google Scholar 

  • Materska, M. and Perucka, I. Antioxidant activity of the main phenolic compounds isolated from hot pepper fruit (Capsicum annuum L.). J. Agric. Food Chem., 53, 1750–1756 (2005).

    Article  CAS  PubMed  Google Scholar 

  • Miyase, T., Ueno, A., Takizawa, N., Kobayashi, H., and Oguchi, H. Ionone and lignan glycosides from Epimedium diphyllum. Phytochemistry, 28, 3483–3485 (1989).

    Article  CAS  Google Scholar 

  • Moon, J. H., Tsushida, T., Nakahara, K., and Terao, J. Identification of quercetin 3-O-β-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin. Free Rad. Biol. Med., 30, 1274–1285 (2001).

    Article  CAS  PubMed  Google Scholar 

  • PAO: major food and agricultural commodities and producers, http://www.fao.org/Ag/AGL/aglw/cropwater/pepper.stm (2001).

  • Reilly, C. A., Crouch, D. J., and Yost, G. S. Andrenyak, D. M., Detection of pepper spray residues on fabrics using liquid chromatography-mass spectrometry. J. Forensic Sci., 47, 37–43 (2002).

    CAS  Google Scholar 

  • Sun, T., Xu, Z., Wu, C. T., Janes, M., Prinyawiwatkul, W., and No, H. K. Antioxidant activities of different colored sweet bell peppers (Capsicum annuum L.). J. Food Sci., 72, 98–102 (2007).

    Article  CAS  Google Scholar 

  • Tsai, T. H., Tsai, P. J., and Ho, S. C. Antioxidant and antiinflammatory activities of several commonly used spices. J. Food Sci., 70, 93–97 (2005).

    Article  Google Scholar 

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Correspondence to Nam-In Baek.

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Lee, DY., Lee, DG., Cho, JG. et al. Lignans from the fruits of the red pepper (Capsicum annuum L.) and their antioxidant effects. Arch. Pharm. Res. 32, 1345–1349 (2009). https://doi.org/10.1007/s12272-009-2001-8

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  • DOI: https://doi.org/10.1007/s12272-009-2001-8

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