Archives of Pharmacal Research

, Volume 32, Issue 10, pp 1345–1349

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

  • Dae-Young Lee
  • Do-Gyeong Lee
  • Jin-Gyeong Cho
  • Myun-Ho Bang
  • Ha-Na Lyu
  • Youn-Hyung Lee
  • Se-Young Kim
  • Nam-In Baek
Research Articles Drug Discovery and Development

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).

Key words

Capsicum annuum L. Vanilloylicariside E5 Icariside E5 (8R)- Isodehydrodiconiferyl alcohol Antioxidant activity DPPH 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 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).CrossRefGoogle Scholar
  2. Beltran, J., Ghosh, A. K., and Basu, S. Immunotherapy of tumors with neuroimmune ligand capsaicin. J. Immunol., 178, 3260–3264 (2007).PubMedGoogle Scholar
  3. 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).CrossRefGoogle Scholar
  4. 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).CrossRefPubMedGoogle Scholar
  5. 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).Google Scholar
  6. 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).CrossRefPubMedGoogle Scholar
  7. 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).Google Scholar
  8. 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).CrossRefGoogle Scholar
  9. 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).CrossRefPubMedGoogle Scholar
  10. 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).CrossRefPubMedGoogle Scholar
  11. Miyase, T., Ueno, A., Takizawa, N., Kobayashi, H., and Oguchi, H. Ionone and lignan glycosides from Epimedium diphyllum. Phytochemistry, 28, 3483–3485 (1989).CrossRefGoogle Scholar
  12. 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).CrossRefPubMedGoogle Scholar
  13. PAO: major food and agricultural commodities and producers, http://www.fao.org/Ag/AGL/aglw/cropwater/pepper.stm (2001).
  14. 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).Google Scholar
  15. 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).CrossRefGoogle Scholar
  16. 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).CrossRefGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea and Springer Netherlands 2009

Authors and Affiliations

  • Dae-Young Lee
    • 1
  • Do-Gyeong Lee
    • 1
  • Jin-Gyeong Cho
    • 1
  • Myun-Ho Bang
    • 2
  • Ha-Na Lyu
    • 1
  • Youn-Hyung Lee
    • 3
  • Se-Young Kim
    • 1
  • Nam-In Baek
    • 1
    • 4
  1. 1.Graduate School of Biotechnology and Department of Oriental Medicinal Materials & ProcessingKyung Hee UniversityYonginKorea
  2. 2.Skin Biotechnology CenterKyung Hee University Gyeonggi BiocenterSuwonKorea
  3. 3.Department of Horticultural BiotechnologyKyung Hee UniversityYonginKorea
  4. 4.Graduate School of BiotechnologyKyung Hee UniversityYong-InKorea

Personalised recommendations