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Anti-melanogenesis Activities for the Terpenes from the Acantophanax koreanum Stems

섬오갈피나무 줄기 유래 테르펜 화합물의 멜라닌 생성 저해 활성

  • Mun, Seung Ri (Department of Chemistry and Cosmetics, Jeju National University) ;
  • Hyun, Ju Mi (Department of Chemistry and Cosmetics, Jeju National University) ;
  • Jo, Yeon Jeong (Department of Chemistry and Cosmetics, Jeju National University) ;
  • Jung, Eun Yeong (Department of Beauty Arts, Cheju Halla University) ;
  • Lee, Nam Ho (Department of Chemistry and Cosmetics, Jeju National University)
  • 문승리 (제주대학교 화학.코스메틱스학과) ;
  • 현주미 (제주대학교 화학.코스메틱스학과) ;
  • 조연정 (제주대학교 화학.코스메틱스학과) ;
  • 정은영 (제주한라대학교 뷰티아트과) ;
  • 이남호 (제주대학교 화학.코스메틱스학과)
  • Received : 2017.10.03
  • Accepted : 2017.10.31
  • Published : 2017.12.30

Abstract

A. koreanum was investigated to identify the constituents possessing whitening effects. As anti-melanogenesis activities were screened for the ethanol extract and solvent fractions, n-hexane (Hex) and ethyl acetate (EtOAc) fractions showed the most potent activities. Three constituents were isolated from the n-Hex fraction of A. koreanum; kaurenoic acid (1), $16{\alpha}$-hydro-17-isovaleroyloxy-ent-kauran-19-oicacid (2), $16{\alpha}$-hydroxy-17-isovaleroyl-oxy-ent-kauran-19-oic acid (3). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including $^1H$ and $^{13}C$ NMR spectra, as well as comparison of the data to the literature values. Whitening effects were studied for the isolated compounds. Upon the anti-melanogenesis test using ${\alpha}-MSH$ stimulated B16F10 melanoma cells, the compounds 1, 2 and 3 inhibited the cellular melanogenesis and intracellular tyrosinase activities effectively. Based on these results, A. koreanum stems extract could be potentially applicable as whitening ingredients in cosmetic formulations.

본 연구에서는 섬오갈피 줄기 추출물 및 용매 분획물의 미백 활성을 검색하고 유효성분을 분리하여 화학구조를 규명하였다. 섬오갈피 줄기 에탄올 추출물 및 용매 분획물의 멜라닌 생성 억제활성을 측정한 결과, 헥산 및 에틸아세테이트 분획물에서 우수한 멜라닌 생성 억제 효과가 있음을 확인하였다. 비교적 세포독성이 적은 헥산 분획물에서 유효성분을 찾고자 크로마토크래피를 실시하여 3개의 화합물을 분리하였으며 $^1H$$^{13}C$ NMR 데이터 분석 및 문헌 비교를 통하여 화학구조를 동정하였다; kaurenoic acid (1), $16{\alpha}$-hydro-17-isovaleroyloxy-ent-kauran-19-oic acid (2), $16{\alpha}$-hydroxy-17-isovaleroyloxy-ent-kauran-19-oic acid (3). 분리된 화합물에 대한 미백 활성 실험 결과, 화합물 1-3 모두 농도의존적으로 멜라닌 생성을 억제하였다. 또한 세포 내 티로시나제 효소의 활성을 감소시킴을 확인하였으며 이러한 연구 결과를 바탕으로 섬오갈피 줄기 추출물은 기능성 미백 화장품 소재로써 활용 가능할 것이라 사료된다.

Keywords

References

  1. B. J. Ha, Cosmeceuticals, Shinkwangpub, 67 (2001).
  2. Y. Jin, S. Y. Ahn, E. S. Hong, G. H. Li, E. K. Kim, and K. H. Raw, Extraction of whitenin agents from natural plants and whitening effect, J. Korean Ind. Eng. Chem., 16, 348 (2005).
  3. T. H. Lee, H. J. Kim, and Y. B. Kim, Depigmentation activity of barley, unpolished rice, Job's-tear, J. Korean Med. Ophthalmol. Otolaryngol. Dermatol., 16, 57 (2003).
  4. J. J. Ahn, T. Y. Hwang, and H. S. Kim, Study on the physiological activities of Cleyera japonica extract, Korean J. Plant Res., 28(2), 153 (2015). https://doi.org/10.7732/kjpr.2015.28.2.153
  5. J. S. Ko, Y. T. Yang, J. K. Park, and Y. J. Lee, Tamraogapi-Cultivation, use and health, Jejuculturepub, 15 (2008).
  6. S. E. Lee, D. W. Son, Y. P. Yoon, S. Y. Lee, B. J. Lee, and S. H. Lee, Protective effect of the methanol extracts of Acanthopanax koreanum against oxidative stress, Kor. J. Pharmacogn., 37(1), 16 (2006).
  7. Korea Patent 10-2013-0043889 (2013).
  8. J. H. Ryu, H. Ahn, J. Y. Kim, and Y. K. Kim, Inhibitory activity of plant extracts on nitric oxide synthesis in LPS-activated macrophages, Phytother. Res., 17, 485 (2003). https://doi.org/10.1002/ptr.1180
  9. Z. Li, J. H Kim, X. Q. Liu, K. T. Lee, and C. S. Yook, Anticancer effects in vitro and chemical compositions of extracts of Acanthopanax henryi, J. Acupuncture and Herbs, 1, 49 (2014).
  10. X. F. Cai, G. Shen, N. T. Dat, O. H. Kang, Y. M. Lee, J. J. Lee, and Y. H. Kim, Inhibitory effect of kaurane type diterpenoids from Acanthopanax koreanum on TNF-${\alpha}$ secretion from trypsin-stimulated HMC-1 cells, Arch. Pharm. Res., 26(9), 731 (2013). https://doi.org/10.1007/BF02976683
  11. H. A. Jung, E. J. Lee, J. S. Kim, S. S. Kang, J. H. Lee, B. S. Min, and J. S. Choi, Cholinesterase and BACE1 inhibitory diterpenoids from Aralia cordata, Arch. Pharm. Res., 32(10), 1399 (2009). https://doi.org/10.1007/s12272-009-2009-0
  12. L. A. Paiva, L. A. Gurgel, R. M. Silva, A. R. Tome, N. V. Gramosa, E. R. Silveria, F. A. Santos, and V. S. Rao, Anti-inflammatory effect of kaurenoic acid, a diterpene from Copaifera langsdorffi on acetic acid-induced colitis in rats, Vascul Pharmacol., 39(6), 303 (2002). https://doi.org/10.1016/S1537-1891(03)00028-4
  13. F. M. Peria, D. G. Tiezzi, D. P. Tirapelli, F. S. Neto, C. R. Tirapelli, S. Ambrosio, H. F. Oliveira, and L. Tirapelli, Kaurenoic acid antitumor activity in breast cancer cells, J. Clinical Oncology, 28(15), e13641 (2010). https://doi.org/10.1200/jco.2010.28.15_suppl.e13641
  14. T. C. Okoye, P. A. Akah, C. O. Okoli, A. C. Ezike, E. O. Omeje, and U. E. Odoh, Antimicrobial effect of a lipophilic fraction and kaurenoic acid isolated from the root bark extracts of Annona senegalensis, J. Evid. Based Complementary Altern. Med., 2012, 10 (2012).
  15. Korea Patent 10-1765577 (2017).