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Journal of Natural Medicines

, Volume 72, Issue 1, pp 155–160 | Cite as

Sesquiterpenes from fruits of Torilis japonica with inhibitory activity on melanin synthesis in B16 cells

  • Da Hye Song
  • Yang Hee Jo
  • Jong Hoon Ahn
  • Seon Beom Kim
  • Cheong-Yong Yun
  • Youngsoo Kim
  • Bang Yeon Hwang
  • Mi Kyeong LeeEmail author
Original Paper
  • 274 Downloads

Abstract

Melanin, a dark macromolecular pigment, protects skin from harmful damage. However, abnormal accumulation is responsible for hyperpigmentation disorders. Melanogenesis inhibitors have therefore become important constituents in cosmetic products for depigmentation. Torilis japonica Decandolle (Umbelliferae) is a biennial plant which is distributed in East Asia. Fruits of this plant have been used for the treatment of skin disease and inflammation. In our previous study, torilin, a major sesquiterpene of T. japonica, showed an inhibitory effect on melanin production in α-melanocyte stimulating hormone (α-MSH)-activated B16 melanoma cells. Further extensive chromatographic separation resulted in thirteen compounds. On the basis of spectroscopic analysis, the structures of the compounds isolated were determined to be three new sesquiterpenes, viz. a guaiane-type, epoxytorilinol (1), a eudesmane-type, elematorilone (2) and a cadinane-type, cardinatoriloside (3), together with ten known sesquiterpenes (413). Of the compounds isolated, compounds 4–6 and 11–13 inhibited α-MSH-activated melanin production in B16 melanoma cells with IC50 values from 72.9 to 191.0 μM.

Keywords

Torilis japonica Sesquiterpene Cadinane Eudesmane Guaiane Anti-melanogenesis 

Notes

Acknowledgements

This work was supported by Basic Science Research Program (2015R1D1A1A09058498) through the National Research Foundation of Korea.

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

References

  1. 1.
    Bae KH (2000) The medicinal plants of Korea. Kyo-Hak Publishing Co., SeoulGoogle Scholar
  2. 2.
    Park WS, Son ED, Nam GW, Kim SH, Noh NS, Lee BG, Jang IS, Kim SE, Lee JJ, Lee CH (2003) Torilin from Torilis japonica, as a new inhibitor of testosterone 5 alpha-reductase. Planta Med 69:459–461CrossRefGoogle Scholar
  3. 3.
    Ryu JH, Jeong YS (2001) A new guaiane type sesquiterpene from Torilis japonica. Arch Pharm Res 24:532–535CrossRefGoogle Scholar
  4. 4.
    Kitajima J, Suzuki N, Satoh M, Watanabe M (2002) Sesquiterpenoids of Torilis japonica fruit. Phytochemistry 59:811–815CrossRefGoogle Scholar
  5. 5.
    Lee IK, Lee JH, Hwang EI, Yun BS (2008) New guaiane sesquiterpenes from the fruits of Torilis japonica. Chem Pharm Bull 56:1483–1485CrossRefGoogle Scholar
  6. 6.
    Endale M, Lee WM, Kwak YS, Kim NM, Kim BK, Kim SH, Cho J, Kim S, Park SC, Yun BS, Ko D, Rhee M (2013) Torilin ameliorates type II collagen-induced arthritis in mouse model of rheumatoid arthritis. Int Immunopharmacol 16:232–242CrossRefGoogle Scholar
  7. 7.
    Park HW, Choi SU, Baek NI, Kim SH, Eun JS, Yang JH, Kim DK (2006) Guaiane sesquiterpenoids from Torilis japonica and their cytotoxic effects on human cancer cell lines. Arch Pharm Res 29:131–134CrossRefGoogle Scholar
  8. 8.
    Choi Y, Lee MK, Lim SY, Sung SH, Kim YC (2009) Inhibition of inducible NO synthase, cyclooxygenase-2 and interleukin-1β by torilin is mediated by mitogen-activated protein kinases in microglial BV2 cells. Br J Pharmacol 156:933–940CrossRefGoogle Scholar
  9. 9.
    Cho WI, Choi JB, Lee K, Chung MS, Pyun YR (2008) Antimicrobial activity of torilin isolated from Torilis japonica fruit against Bacillus subtilis. J Food Sci 73:37–46CrossRefGoogle Scholar
  10. 10.
    Chang TS (2009) An updated review of tyrosinase inhibitors. Int J Mol Sci 10:2440–2475CrossRefGoogle Scholar
  11. 11.
    Solano F, Briganti S, Picardo M, Ghanem G (2006) Hypopigmenting agents: an updated review on biological, chemical and clinical aspects. Pigment Cell Res 19:550–571CrossRefGoogle Scholar
  12. 12.
    Rigopoulos D, Gregoriou S, Katsambas A (2007) Hyperpigmentation and melisma. J Cosmet Dermatol 6:195–202CrossRefGoogle Scholar
  13. 13.
    Nieuweboer-Krobotova L (2013) Hyperpigmentation: types, diagnostics and targeted treatment options. J Eur Acad Dermatol Venereol S1:2–4CrossRefGoogle Scholar
  14. 14.
    Prota G (1988) Progress in the chemistry of melanins and related metabolites. Med Res Rev 8:525–556CrossRefGoogle Scholar
  15. 15.
    Rees JL (2003) Genetics of hair and skin color. Annu Rev Genet 37:67–90CrossRefGoogle Scholar
  16. 16.
    Kim YJ, Uyana H (2005) Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 62:1707–1723CrossRefGoogle Scholar
  17. 17.
    Parvez S, Kang M, Chung HW, Bae H (2007) Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries. Phytother Res 21:805–816CrossRefGoogle Scholar
  18. 18.
    Yun CY, Kim D, Lee WH, Park YM, Lee SH, Na M, Jahng Y, Hwang BY, Lee MK, Han SB, Kim Y (2009) Torilin from Torilis japonica inhibits melanin production in alpha-melanocyte stimulating hormone-activated B16 melanoma cells. Planta Med 75:1505–1508CrossRefGoogle Scholar
  19. 19.
    Fu HW, Zhang L, Yi T, Feng YL, Tian JK (2010) Two new guaiane-type sesquiterpenoids from the fruits of Daucus carota L. Fitoterapia 81:443–446CrossRefGoogle Scholar
  20. 20.
    Wang HX, Liu CM, Liu Q, Gao K (2008) Three types of sesquiterpenes from rhizomes of Atractylodes lancea. Phytochemistry 69:2088–2094CrossRefGoogle Scholar
  21. 21.
    Karamenderes C, Bedir E, Pawar R, Baykan S, Khan IA (2007) Elemanolide sesquiterpenes and eudesmane sesquiterpene glycosides from Centaurea hierapolitana. Phytochemistry 68:609–615CrossRefGoogle Scholar
  22. 22.
    Kuo YH, Chyu CF, Lin HC (2003) Cadinane-type sesquiterpenes from the roots of Taiwania cryptomerioides Hayata. Chem Pharm Bull 51:986–989CrossRefGoogle Scholar
  23. 23.
    Kuo YH, Chen CH, Chien SC, Lin YL (2002) Five new cadinane-type sesquiterpenes from the heartwood of Chamaecyparis obtusa var. formosana. J Nat Prod 65:25–28CrossRefGoogle Scholar
  24. 24.
    Fu HW, Zhang L, Yi T, Chen RZ, Wang X, Tian JK (2010) Two new guaiane-type sesquiterpene glycosides from the fruits of Daucus carota L. Chem Pharm Bull 58:125–128CrossRefGoogle Scholar
  25. 25.
    Yu Y, Gao H, Dai Y, Xiao GK, Zhu HJ, Yao XS (2011) Guaiane-type sesquiterpenoid glucosides from Gardenia jasminoides Ellis. Magn Reson Chem 49:258–261CrossRefGoogle Scholar
  26. 26.
    Kitajima J, Suzuki N, Tanaka Y (1998) Three new sesquiterpenoid glucosides of Ficus pumila fruit. Chem Pharm Bull 48:77–80CrossRefGoogle Scholar
  27. 27.
    Brown GD, Liang GY, Sy LK (2003) Terpenoids from the seeds of Artemisia annua. Phytochemistry 64:303–323CrossRefGoogle Scholar
  28. 28.
    Shin H, Hong SD, Roh E, Jung SH, Cho WJ, Park SH, Yoon DY, Ko SM, Hwang BY, Hong JT, Heo TY, Han SB, Kim Y (2015) cAMP-dependent activation of protein kinase A as a therapeutic target of skin hyperpigmentation by diphenylmethylene hydrazine carbothioamide. Br J Pharmacol 172:3434–3445CrossRefGoogle Scholar
  29. 29.
    Kim SB, Jo YH, Liu Q, Ahn JH, Hong IP, Han SM, Hwang BY, Lee MK (2015) Optimization of extraction condition of bee pollen using response surface methodology: correlation between anti-melanogenesis, antioxidant activity, and phenolic content. Molecules 20:19764–19774CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan KK 2017

Authors and Affiliations

  • Da Hye Song
    • 1
  • Yang Hee Jo
    • 1
  • Jong Hoon Ahn
    • 1
  • Seon Beom Kim
    • 1
  • Cheong-Yong Yun
    • 1
  • Youngsoo Kim
    • 1
  • Bang Yeon Hwang
    • 1
  • Mi Kyeong Lee
    • 1
    Email author
  1. 1.College of PharmacyChungbuk National UniversityCheongjuKorea

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