Skip to main content
SpringerLink
Log in

Triterpene glycosides with stimulatory activity on melanogenesis from the aerial parts of Weigela subsessilis

  • Research Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Three new triterpene glycosides (Lonicerosides K, L and M) and 11 known compounds were isolated from the aerial parts of Weigela subsessilis. Among the known isolated compounds, loniceroside A, sweroside, kaempferol-3-O-glucopyranoside 6″-(3-hydroxy-3-methylglutarate), kaempferol-3-O-acetylglucoside and grandifloroside were reported for the first time in a Weigela genus plant. Their chemical structures were identified using extensive spectroscopic analysis including two-dimensional (2D)-NMR experiments, HR-ESI-QTOF-MS and comparison with reported data. Among these compounds, lonicerosides A and L had potent melanogenesis stimulatory activity in murine B16F0 melanoma cells. The structural relationship of active compounds was discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  • Ahn, M.J., S.J. Hur, E.H. Kim, S.H. Lee, J.S. Shin, M.K. Kim, J.A. Uchizono, W.K. Whang, and D.S. Kim. 2014. Scopoletin from Cirsium setidens increases melanin synthesis CREB phosphorylation in B16F10 cells. Korean Journal of Physiology & Pharmacology 18: 307–311.

  • Alikhan, A., L.M. Felsten, M. Daly, and V. Petronic-Rosic. 2011. Vitiligo: a comprehensive overview. Part I: Introduction, epidemiology, quality of life, diagnosis, differential diagnosis, associations, histopathology, etiology, and work-up. Journal of the American Academy of Dermatology 65(3): 473–491.

    Article  PubMed  Google Scholar 

  • Burton, G., and E.A. Evans-Illidge. 2014. Emerging R and D law: The Nagoya Protocol and its implications for researchers. ACS Chemical Biology 9: 588–591.

    Article  CAS  PubMed  Google Scholar 

  • Chang, C.S. 1997. Flavonoid chemistry of Weigela (Caprifoliaceae) in Korea. Journal of Plant Research 110: 275–281.

    Article  CAS  Google Scholar 

  • Chae, H.S., O.H. Kang, Y.S. Lee, J.G. Choi, Y.C. Oh, H.J. Jang, M.S. Kim, J.H. Kim, S.L. Jeong, and D.Y. Kwon. 2009. Inhibition of LPS-induced iNOS, COX-2 and inflammatory mediator expression by Paeonol through the MAPKs inactivation in RAW 264.7 cells. The American Journal of Chinese Medicine 37: 181–194.

  • Felsten, L.M., A. Alikhan, and V. Petronic-Rosic. 2011. Vitiligo: a comprehensive overview. Part II: Treatment options and approach to treatment. Journal of the American Academy of Dermatology 65(3): 493–514.

    Article  PubMed  Google Scholar 

  • Fu, Q., K. Zan, M.B. Zhao, S.X. Zhou, S.P. Shi, Y. Jiang, and P.F. Tu. 2010. Triterpene saponins from Clematis chinensis and their potential anti-inflammatory activity. Journal of Natural Product 73: 1234–1239.

    Article  CAS  Google Scholar 

  • Hu, J., Y. Song, H. Li, B. Yang, X. Mao, Y. Zhao, and Z. Shi. 2014. Cytotoxic triterpene glycosides from the roots of Sanguisorba officinalis. Archives of Pharmacal Research. doi:10.1007/s12272-014-0477-3.

  • Jung, G.D., J.Y. Yang, E.S. Song, and J.W. Park. 2001. Stimulation of melanogenesis by glycyrrhizin in B16 melanoma cells. Experimental & Molecular Medicine 33(3): 131–135.

    Article  CAS  Google Scholar 

  • Kim, D.Y., J.W. Lee, S.H. Whang, Y.K. Park, S.K. Hann, and Y.J. Shin. 2009. Quality of life for Korean patients with vitiligo: Skindex-29 and its correlation with clinical profiles. Journal of Dermatology 36: 317–322.

  • Kim, T.J. 1996. Korean resources plants, 146. Seoul: Seoul National University.

    Google Scholar 

  • Kizu, H., and T. Tomimori. 1982. Studies on the constituents of Clematis. V. On the saponins of the roots of Clematis chinensis Osbeck. Chemical & Pharmaceutical Bulletin 30: 3340–3346.

    Article  CAS  Google Scholar 

  • Kuroda, M., T. Shizume, and Y. Mikaki. 2014. Triterpene glycosides from the stems and leaves of Lonicera japonica. Chemical & Pharmaceutical Bulletin 62(1): 92–96.

    Article  CAS  Google Scholar 

  • Lee, J.S., E.S. Jung, J.H. Park, K.S. Jung, E.K. Park, J.E. Kim, S.T. Hong, J.I. Park, S.H. Park, S.Y. Lee, and D.H. Park. 2005. Glycyrrhizin induces melanogenesis by elevating a cAMP level in b16 melanoma cells. Journal of Investigative Dermatology. 124: 405–411.

    Article  CAS  PubMed  Google Scholar 

  • Lee, M.S., and P.T. Thuong. 2010. Stimulation of glucose uptake by triterpenoids from Weigela subsessilis. Phytotherapy Research. 24(1): 49–53.

    Article  CAS  PubMed  Google Scholar 

  • Lee, M.Y., J.E. Yuk, O.K. Kwon, S.R. Oh, H.K. Lee, and K.S. Ahn. 2012. Zuonin B Inhibits Lipopolysaccharide-induced inflammation via downregulation of the ERK1/2 and JNK pathways in RAW264.7 macrophages. Evidence-Based Complementary and Alternative Medicine 728196, 8 pages.

  • Lee, S.R., E.S. Jung, S.G. Do, G.Y. Jung, G.P. Song, J.M. Song, and C.H. Lee. 2014. Correlation between species-specific metabolite profiles and bioactivities of blueberries (Vaccinium spp.). Journal of Agricultural and Food Chemistry 62: 2126–2133.

  • Li, B., Z. Abliz, G. Fu, M. Tang, and S. Yu. 2005. Characteristic fragmentation behavior of some glucuronide-type triterpenoid saponins using electrospray ionization tandem mass spectrometry. Rapid Communication in Mass Spectrometry. 19: 381–390.

    Article  Google Scholar 

  • Manga, P., D. Sheyn, F. Yang, R. Sarangarajan, and R.E. Boissy. 2006. A role for tyrosinase-related protein 1 in 4-tert-butylphenol-induced toxicity in melanocytes: Implications for vitiligo. American Journal of Pathology 169(5): 1652–1662.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Matsuda, H., N. Hirata, Y. Kawaguchi, M. Yamazaki, S. Naruto, M. Shibano, M. Taniguchi, K. Baba, and M. Kubo. 2005. Melanogenesis stimulation in murine B16 Melanoma cells by Umberiferae plant extracts and their coumarin constituents. Biological and Pharmaceutical Bulletin 28(7): 1229–1233.

  • Odashima, S., T. Ohta, H. Kohno, T. Matsuda, I. Kitagawa, H. Abe, and S. Arichi. 1985. Control of phenotypic expression of cultured B16 melanoma cells by plant glycosides. Cancer Research 45: 2781–2784.

  • Son, K.H., K.Y. Jung, H.W. Chang, H.P. Kim, and S.S. Kang. 1994. Triterpenoid saponins from the aerial parts of Lonicera japonica. Phytochemistry 35(4): 1005–1008.

    Article  CAS  PubMed  Google Scholar 

  • Song, H.H., H.S. Chae, S.R. Oh, H.K. Lee, and Y.W. Chin. 2012. Anti-inflammatory and anti-allergic effect of Agaricus blazei extract in bone marrow-derived mast cells. The American Journal of Chinese Medicine 40(5): 1073–1084.

  • Sun, F., Q. He, P. Shi, P. Xiao, and Y. Cheng. 2007. Characterization and identification of triterpenoid saponins in crude extracts from Clematis spp. by high-performance liquid chromatography/electrospray ionization with multi-stage tandem mass spectrometry. Rapid Communication in Mass Spectrometry 21: 3743–3750.

  • Thuong, P.T., B.S. Min, W.Y. Jin, M.K. Na, J.P. Lee, R.S. Seong, Y.M. Lee, K.S. Song, Y.H. Seong, H.K. Lee, K.H. Bae, and S.S. Kang. 2006. Anti-complementary activity of ursane-type triterpenoids from Weigela subsessilis. Biological and Pharmaceutical Bulletin. 29(4): 830–833.

    Article  CAS  PubMed  Google Scholar 

  • Thuong, P.T., W.Y. Jin, J.P. Lee, R.S. Seong, Y.M. Lee, Y.H. Seong, K.S. Song, and K.H. Bae. 2005a. Inhibitory effect on TNF-alpha-induced IL-8 production in the HT29 cell of constituents from the leaf and stem of Weigela subsessilis. Archives of Pharmacal Research 28(10): 1135–1141.

    Article  CAS  PubMed  Google Scholar 

  • Thuong, P.T., M.K. Na, N.D. Su, R.S. Seong, Y.M. Lee, D.E. Sok, and K.H. Bae. 2005b. Inhibitory effect of coumarins from Weigela subsessilis on low density lipoprotein oxidation. Biological and Pharmaceutical Bulletin. 28(6): 1095–1097.

    Article  CAS  PubMed  Google Scholar 

  • Won, H.M., Y.S. Kwon, J.H. Lee, and C.M. Kim. 2004. Chemical constituents of the leaves of Weigela subsessillis. Korean Journal of Pharmacognosy. 35(1): 1–5.

    CAS  Google Scholar 

  • Yamaguchi, Y., and V.J. Hearing. 2009. Physiological factors that regulate skin pigmentation. BioFactors 35(2): 193–199.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Yamaguchi, Y., and V.J. Hearing. 2014. Melanocytes and their diseases. Cold Spring Harb Perspect Med 4: a017046.

  • Yamauchi, K., T. Mitsunaga, and I. Batubara. 2014. Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells. Bioorganic & Medicinal Chemistry 22: 937–944.

Download references

Acknowledgments

We thank Dr. Dong Ho Jung (KRIBB) for assistance with our NMR spectra. This research was supported by a Grant from the KRIBB Research Initiative program and the Jeonnam Development Institute for Korean Traditional Medicines.

Author information

Authors and Affiliations

  1. Biomolecular Science, University of Science and Technology, UST, Daejeon, 305-806, Korea

    Yu-Mi Won, Zuh-Kyung Seong, Jae-Lim Kim & Hyeong-Kyu Lee

  2. Natural Medicine Research Center, Korea Research Institute of Bioscience & Biotechnology, Yeongudanji-ro 30, Ochang-eup, Cheongwon-gu, Cheongju-si, 363-883, Korea

    Yu-Mi Won, Zuh-Kyung Seong, Jae-Lim Kim, Hyuk-Hwan Song, Doo-Young Kim, Jung-Hee Kim, Sei-Ryang Oh & Hyeong-Kyu Lee

  3. Division of AIDS, Center for Immunology and Pathology, Korea National Institute of Health, 187 Osongsaengmyeong2-ro, Cheongwon-gu, Cheongju-si, 363-951, Korea

    Hui-Seong Kim

  4. Jeonnam Development Institute for Korean Traditional Medicines, 288 Woodland-gil, Anyang-myeon, Jangheung-Gun, Jeonnam, Korea

    Hyun-Woo Cho & Jung-Hee Cho

Authors
  1. Yu-Mi Won
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zuh-Kyung Seong
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jae-Lim Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hui-Seong Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hyuk-Hwan Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Doo-Young Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Jung-Hee Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Sei-Ryang Oh
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Hyun-Woo Cho
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Jung-Hee Cho
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Hyeong-Kyu Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hyeong-Kyu Lee.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 2271 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Won, YM., Seong, ZK., Kim, JL. et al. Triterpene glycosides with stimulatory activity on melanogenesis from the aerial parts of Weigela subsessilis . Arch. Pharm. Res. 38, 1541–1551 (2015). https://doi.org/10.1007/s12272-014-0524-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-014-0524-0

Keywords

Search

Navigation