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References

  1. Hou K. 1984. A Dictionary of the Families and Genera of Chinese Seed Plants. Science Press, Beijing, China.
  2. Qian JY, Liu D, Huang AG. 2004. The efficiency of flavonoids in polar extracts of Lycium chinense Mill fruits as free radical scavenger. Food Chem. 87: 283-288.
    CrossRef
  3. Gao XM, Xu ZM, Li ZW. 2000. Traditional Chinese Medicines. People’s Health Publishing House, Beijing, China.
  4. Sannai A, Fujimori T, Kato K. 1980. Isolation of (−)-1,2-dehydro-α-cyperone and solavetivone from Lycium chinense. Plant Biochem. 21: 2986-2987.
    CrossRef
  5. Kim SY, Choi YH, Huh H, Kim JW, Kim YC, Lee HS. 1997. New antihepatotoxic cerebroside from Lycium chinense fruits. J. Nat. Prod. 60: 274-276.
    Pubmed CrossRef
  6. Pérez-Jiménez J, Serrano J, Tabernero M, Arranz S, DíazRubio ME, García-Diz L, et al. 2009. Bioavailability of phenolic antioxidants associated with dietary fiber: plasma antioxidant capacity after acute and long-term intake in humans. Plant Foods Human Nutr. 64: 102-107.
    Pubmed CrossRef
  7. Chon SU, Heo BG, Park YS, Kim DK, Gorinstein S. 2009. Total phenolics level, antioxidant activities and cytotoxicity of young sprouts of some traditional Korean salad plants. Plant Foods Human Nutr. 64: 25-31.
    Pubmed CrossRef
  8. Bystrom LM, Lewis BA, Brown DL, Rodriguez EO. 2009. Phenolics, sugars, antimicrobial and free-radical-scavenging activities of Melicoccus bijugatus Jacq. fruits from the Dominican Republic and Florida. Plant Foods Human Nutr. 64: 160-166.
    Pubmed CrossRef
  9. Han SH, Lee HH, Lee IS. 2002. A new phenolic amide from Lycium chinense Miller. Arch. Pharm. Res. 25: 433-437.
    Pubmed CrossRef
  10. Kaplanski G, Marin V, Julian FM, Mantovani A, Farnarier C. 2003. IL-6: a regulator of the transition from neutrophil to monocyte recruitment during inflammation. Trends Immun. 24: 25-29.
    CrossRef
  11. Lawrence T, Willoughby DA, Gilroy DW. 2002. Antiinflammatory lipid mediators and insights into the resolution of inflammation. Nat. Rev. Immunol. 2: 787-795.
    Pubmed CrossRef
  12. Eiserich JP, Hristova M, Cross CE, Jones AD, Freeman BA, Halliwell B, et al. 1998. Formation of nitric oxide derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature 391: 393-397.
    Pubmed CrossRef
  13. Fu X, Huang Y, Kang X, Li T, Jia X, Dong L, et al. 2014. The wolfberry bud tea has enhanced antioxidant activities. Austin J. Nutr. Food Sci. 2: 1018.
  14. D’Agostino P, Ferlazzo V, Milano S, La Rosa M, Di Bella G, Caruso R, et al. 2001. Anti-inflammatory effects of chemically modified tetracyclines by the inhibition of nitric oxide and interleukin-12 synthesis in J774 cell line. Int. Immunopharm. 1: 1765-1776.
    CrossRef
  15. Fautz R, Husein B, Hechenberger C. 1991. Application of the neutral red assay (NR assay) to monolayer cultures of primary hepatocytes: rapid colorimetric viability determination for the unscheduled DNA synthesis test (UDS). Mutat. Res. 253: 173-179.
    CrossRef
  16. Yoshihara T, Takamatsu S, Sakamura S. 1978. Three new phenolic amides from the roots of eggplant (Solanum melongena L.). Agric. Biol. Chem. 43: 623-627.
    CrossRef
  17. Chen CY, Chang FR, Yen HF, Wu YC. 1998. Amides from stems of Annona cherimola. Phytochemistry 49: 1443-1447.
    CrossRef
  18. Kim HR, Min HY, Jeong YH, Lee SK, Lee NS, Seo EK. 2005. Cytotoxic constituents from the whole plant of Corydalis pallida. Arch. Pharm. Res. 28: 1224-1227.
    Pubmed CrossRef
  19. Kanada RM, Simionato JI, de Arruda RF, de Oliveira Santin SM, de Souza MC, da Silva CC. 2012. N-trans-feruloyltyramine and flavonol glycosides from the leaves of Solanum sordidum. Braz. J. Pharm. 22: 502-506.
    CrossRef
  20. Fujii T, Wakaizumi M, Ikami T, Saito M. 2008. Amla (Emblica officinalis Gaertn.) extract promotes procollagen production and inhibits matrix metalloproteinase-1 in human skin fibroblasts. J. Ethnopharm. 119: 53-57.
    Pubmed CrossRef
  21. Hämäläinen M, Nieminen R, Vuorela P, Heinonen M, Moilanen E. 2007. Anti-inflammatory effects of flavonoids:genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and NF-κB activations, whereas flavone, isorhamnetin, naringenin, and pelargonidin inhibit only NF-κB activation along with their inhibitory effect on iNOS expression and NO production in activated macrophages. Mediators Inflamm. 2007: 45673.
    Pubmed PMC CrossRef
  22. Choi J, Huh K, Kim SH, Lee KT, Park HJ, Han YN. 2002. Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals. J. Ethnopharm. 79: 199-204.
    CrossRef
  23. Speroni E, Cervellati R, Innocenti G, Costa S, Guerra MC, Dall’ Acqua S, et al. 2005. Anti-inflammatory, anti-nociceptive and antioxidant activities of Balanites aegyptiaca (L.) Delile. J. Ethnopharm. 98: 177-125.
    Pubmed CrossRef
  24. Kim YL, Han MS, Lee JS, Kim JW, Kim YC. 2003. Inhibitory phenolic amides on lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells from Beta vulgaris var. cicla seeds. Phytother. Res. 17: 983-985.
    Pubmed CrossRef
  25. Efdi M, Ohguchi K, Akao Y, Nozawa Y, Koketsu M, Ishihara H. 2007. N-transferuloyltyramine as a melanin biosynthesis inhibitor. Biol. Pharm. Bull. 30: 1972-1974.
    Pubmed CrossRef
  26. Fujita S, Ninomiya M, Efdi M, Ohguchi K, Nozawa Y, Koketsu M. 2010. Isolation of chemical constituents from Enicosanthum cupulare (King) Airy-Shaw. Nat. Prod. Res. 24: 1630-1636.
    Pubmed CrossRef

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Article

J. Microbiol. Biotechnol. 2017; 27(8): 1386-1391

Published online August 28, 2017 https://doi.org/10.4014/jmb.1702.02004

Copyright © The Korean Society for Microbiology and Biotechnology.

Nitric Oxide Inhibition and Procollagen Type I Peptide Synthesis Activities of a Phenolic Amide Identified from the Stem of Lycium chinense Miller

Chan Seam Gil 1, Moon Sik Jang 2 and Seok Hyun Eom 1*

Department of Horticultural Biotechnology, College of Life Sciences, Kyung Hee University, Republic of Korea, 1The Garden of Naturalsolution Company, Republic of Korea

Received: February 3, 2017; Accepted: May 15, 2017

Abstract

The bioactivities of boxthron fruits, a source of oriental medicine, are well known, whereas
phytochemical studies of the boxthorn stem are rare. In this study, the stem extract of
boxthorn (Lycium chinense Miller) and its subfractions were evaluated for their effects on nitric
oxide (NO) inhibition and procollagen type I peptide (PIP) synthesis. A phenolic amide
isolated from the stem extract was also assayed for these effects. The compound, N-transferuloyltyramine,
was identified by 1H, 13C, and 2D-nuclear magnetic resonance analyses. In
NO inhibition, the chloroform fraction (CF) exhibited the strongest inhibitory activity
(MIC50 = 24.69 μg/ml) among the subfractions of the ethanol extract (EE). N-transferuloyltyramine
isolated from the CF showed strong NO inhibitory activity, presenting with
an MIC50 of 31.36 μg/ml. The EE, CF, and N-trans-feruloyltyramine shown to have NO
inhibition activity were assayed for the activity of PIP synthesis. The EE and CF showed
relatively high PIP values of 38.8% and 24.21% at 100 μg/ml, respectively. The PIP value for
20 μg/ml N-trans-feruloyltyramine showed a 36% increase compared with the non-treated
control, whereas that treated with 20 μg/ml ascorbic acid as a positive control showed a 13%
increase. The results suggest that the proper stem extract of boxthorn stem could be efficiently
used to produce good cosmetic effects.

Keywords: Boxthorn, nitric oxide inhibition, N-trans-feruloyltyramine, procollagen type I peptide synthesis

References

  1. Hou K. 1984. A Dictionary of the Families and Genera of Chinese Seed Plants. Science Press, Beijing, China.
  2. Qian JY, Liu D, Huang AG. 2004. The efficiency of flavonoids in polar extracts of Lycium chinense Mill fruits as free radical scavenger. Food Chem. 87: 283-288.
    CrossRef
  3. Gao XM, Xu ZM, Li ZW. 2000. Traditional Chinese Medicines. People’s Health Publishing House, Beijing, China.
  4. Sannai A, Fujimori T, Kato K. 1980. Isolation of (−)-1,2-dehydro-α-cyperone and solavetivone from Lycium chinense. Plant Biochem. 21: 2986-2987.
    CrossRef
  5. Kim SY, Choi YH, Huh H, Kim JW, Kim YC, Lee HS. 1997. New antihepatotoxic cerebroside from Lycium chinense fruits. J. Nat. Prod. 60: 274-276.
    Pubmed CrossRef
  6. Pérez-Jiménez J, Serrano J, Tabernero M, Arranz S, DíazRubio ME, García-Diz L, et al. 2009. Bioavailability of phenolic antioxidants associated with dietary fiber: plasma antioxidant capacity after acute and long-term intake in humans. Plant Foods Human Nutr. 64: 102-107.
    Pubmed CrossRef
  7. Chon SU, Heo BG, Park YS, Kim DK, Gorinstein S. 2009. Total phenolics level, antioxidant activities and cytotoxicity of young sprouts of some traditional Korean salad plants. Plant Foods Human Nutr. 64: 25-31.
    Pubmed CrossRef
  8. Bystrom LM, Lewis BA, Brown DL, Rodriguez EO. 2009. Phenolics, sugars, antimicrobial and free-radical-scavenging activities of Melicoccus bijugatus Jacq. fruits from the Dominican Republic and Florida. Plant Foods Human Nutr. 64: 160-166.
    Pubmed CrossRef
  9. Han SH, Lee HH, Lee IS. 2002. A new phenolic amide from Lycium chinense Miller. Arch. Pharm. Res. 25: 433-437.
    Pubmed CrossRef
  10. Kaplanski G, Marin V, Julian FM, Mantovani A, Farnarier C. 2003. IL-6: a regulator of the transition from neutrophil to monocyte recruitment during inflammation. Trends Immun. 24: 25-29.
    CrossRef
  11. Lawrence T, Willoughby DA, Gilroy DW. 2002. Antiinflammatory lipid mediators and insights into the resolution of inflammation. Nat. Rev. Immunol. 2: 787-795.
    Pubmed CrossRef
  12. Eiserich JP, Hristova M, Cross CE, Jones AD, Freeman BA, Halliwell B, et al. 1998. Formation of nitric oxide derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature 391: 393-397.
    Pubmed CrossRef
  13. Fu X, Huang Y, Kang X, Li T, Jia X, Dong L, et al. 2014. The wolfberry bud tea has enhanced antioxidant activities. Austin J. Nutr. Food Sci. 2: 1018.
  14. D’Agostino P, Ferlazzo V, Milano S, La Rosa M, Di Bella G, Caruso R, et al. 2001. Anti-inflammatory effects of chemically modified tetracyclines by the inhibition of nitric oxide and interleukin-12 synthesis in J774 cell line. Int. Immunopharm. 1: 1765-1776.
    CrossRef
  15. Fautz R, Husein B, Hechenberger C. 1991. Application of the neutral red assay (NR assay) to monolayer cultures of primary hepatocytes: rapid colorimetric viability determination for the unscheduled DNA synthesis test (UDS). Mutat. Res. 253: 173-179.
    CrossRef
  16. Yoshihara T, Takamatsu S, Sakamura S. 1978. Three new phenolic amides from the roots of eggplant (Solanum melongena L.). Agric. Biol. Chem. 43: 623-627.
    CrossRef
  17. Chen CY, Chang FR, Yen HF, Wu YC. 1998. Amides from stems of Annona cherimola. Phytochemistry 49: 1443-1447.
    CrossRef
  18. Kim HR, Min HY, Jeong YH, Lee SK, Lee NS, Seo EK. 2005. Cytotoxic constituents from the whole plant of Corydalis pallida. Arch. Pharm. Res. 28: 1224-1227.
    Pubmed CrossRef
  19. Kanada RM, Simionato JI, de Arruda RF, de Oliveira Santin SM, de Souza MC, da Silva CC. 2012. N-trans-feruloyltyramine and flavonol glycosides from the leaves of Solanum sordidum. Braz. J. Pharm. 22: 502-506.
    CrossRef
  20. Fujii T, Wakaizumi M, Ikami T, Saito M. 2008. Amla (Emblica officinalis Gaertn.) extract promotes procollagen production and inhibits matrix metalloproteinase-1 in human skin fibroblasts. J. Ethnopharm. 119: 53-57.
    Pubmed CrossRef
  21. Hämäläinen M, Nieminen R, Vuorela P, Heinonen M, Moilanen E. 2007. Anti-inflammatory effects of flavonoids:genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and NF-κB activations, whereas flavone, isorhamnetin, naringenin, and pelargonidin inhibit only NF-κB activation along with their inhibitory effect on iNOS expression and NO production in activated macrophages. Mediators Inflamm. 2007: 45673.
    Pubmed KoreaMed CrossRef
  22. Choi J, Huh K, Kim SH, Lee KT, Park HJ, Han YN. 2002. Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals. J. Ethnopharm. 79: 199-204.
    CrossRef
  23. Speroni E, Cervellati R, Innocenti G, Costa S, Guerra MC, Dall’ Acqua S, et al. 2005. Anti-inflammatory, anti-nociceptive and antioxidant activities of Balanites aegyptiaca (L.) Delile. J. Ethnopharm. 98: 177-125.
    Pubmed CrossRef
  24. Kim YL, Han MS, Lee JS, Kim JW, Kim YC. 2003. Inhibitory phenolic amides on lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells from Beta vulgaris var. cicla seeds. Phytother. Res. 17: 983-985.
    Pubmed CrossRef
  25. Efdi M, Ohguchi K, Akao Y, Nozawa Y, Koketsu M, Ishihara H. 2007. N-transferuloyltyramine as a melanin biosynthesis inhibitor. Biol. Pharm. Bull. 30: 1972-1974.
    Pubmed CrossRef
  26. Fujita S, Ninomiya M, Efdi M, Ohguchi K, Nozawa Y, Koketsu M. 2010. Isolation of chemical constituents from Enicosanthum cupulare (King) Airy-Shaw. Nat. Prod. Res. 24: 1630-1636.
    Pubmed CrossRef