Skip to main content
SpringerLink
Log in

Evaluation of the chemical quality of Sekkoku (石斛) in current Japanese commercial crude drugs: constituents of Flickingeria xantholeuca (Rchb. f.) A.D. Hawkes

  • Original Paper
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

In our investigation, most Shihu (石斛; Japanese name, Sekkoku) in current Japanese commercial crude drugs were from Flickingeria xantholeuca (Orchidaceae). As the index compounds, three new ent-pimarane-type diterpenes, flickinxthanthosides A–C (1–3), one known analogue (7), and three new ent-kaurane-type diterpenes, flickinxanthosides D (4) and E (5) and flickinxanthol A (6) were isolated from the stem of F. xantholeuca. The structures of the new compounds were elucidated on the basis of spectroscopic analyses and chemical methods. We attempted to detect these index compounds from the MeOH extracts of other Dendrobium or Flickingeria plants using TLC and LC/MS.

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
Fig. 7

Similar content being viewed by others

References

  1. Xu J, Han QB, Li SL, Chen XJ, Wang XN, Zhao ZZ, Chen HB (2013) Chemistry, bioactivity and quality control of Dendrobium, a commonly used tonic herb in traditional Chinese medicine. Phytochem Rev 12:341–367

    Article  CAS  Google Scholar 

  2. Ng TB, Liu J, Wong JH, Ye X, Wing Sze SC, Tong Y, Zhang KY (2012) Review of research on Dendrobium, a prized folk medicine. Appl Microbiol Biotechnol 93:1795–1803

    Article  CAS  PubMed  Google Scholar 

  3. Lam Y, Ng TB, Yao RM, Shi J, Xu K, Wing Sze SC, Zhang KY (2015) Evaluation of chemical constituents and important mechanism of pharmacological biology in Dendrobium plants. Evid Based Complement Altern Med 29:841752

  4. Tezuka Y, Hirano H, Kikuchi T, Xu GJ (1991) Constituents of Ephemerantha lonchophylla: isolation of new phenolic compounds, ephemeranthol-A, ephemeranthol-B, and ephemeranthoquinone, and of a new diterpene glucoside, ephemeranthoside. Chem Pharm Bull 39(3):593–598

    Article  CAS  Google Scholar 

  5. Ma GX, Wang TS, Yin L, Pan Y (1998) Two pimarane diterpenoids from Ephemerantha lonchophylla and their evaluation as modulators of the multidrug resistance phenotype. J Nat Prod 61:112–115

    Article  CAS  Google Scholar 

  6. Li H, Zhao JJ, Chen JL, Zhu LP, Wang DM, Jiang L, Yang DP, Zhao ZM (2015) Diterpenoids from aerial parts of Flickingeria fimbriata and their nuclear factor-kappaB inhibitory activities. Phytochemistry 117:400–409

    Article  CAS  PubMed  Google Scholar 

  7. Hsu TC, Chung SW, Kuo CM (2012) Supplements to the Orchid flora of Taiwan. Taiwania 57(3):271–277

    Google Scholar 

  8. Snatzke G (1965) Circular dichroism. VIII. Modification of the octant rule for α, β-unsaturated ketones: theory. Tetrahedron 21:413–419

    Article  CAS  Google Scholar 

  9. Kan Y, Fujita T, Nagai H, Sakamoto B, Hokama Y (1998) Malyngamides M and N from the Hawaiian red alga Gracilaria coronopifolia. J Nat Prod 61:152–155

    Article  CAS  PubMed  Google Scholar 

  10. Tinto WF, Blyden G, Reynolds WF, McLean S (1991) Diterpene and anthraquinone constituents of Glycydendron amazonicum. J Nat Prod 54(4):1127–1130

    Article  CAS  Google Scholar 

  11. Liu G, Müller R, Rüedi P (2003) Chemical transformations of Phyllocladane (=13β-kaurane) diterpenoids. Helv Chem Acta 86:420–438

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to Dr. K. Minoura for NMR spectra recordings and Dr. M. Fujitake for mass spectra recordings at the Osaka University of Pharmaceutical Sciences. We thank Ms. Su Su Wai Lwin (Department of Agriculture, Ministry of Agriculture and Irrigation) for collaborating on the field survey in Myanmar.

Author information

Authors and Affiliations

  1. Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka, 569-1094, Japan

    Mei Muto, Kazuo Ozaki & Makio Shibano

  2. National Defense Medicinal College, 3-2 Namiki, Tokorozawa, Saitama, 359-8513, Japan

    Haruka Asahina

  3. Research Institute of Medicinal Plant Resources, Shinnihonseiyaku Co., Ltd., 275 Hongo-machi, Iwakuni, Yamaguchi, 740-0602, Japan

    Tatsufumi Yoshioka

Authors
  1. Mei Muto
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Haruka Asahina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tatsufumi Yoshioka
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kazuo Ozaki
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Makio Shibano
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Makio Shibano.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Muto, M., Asahina, H., Yoshioka, T. et al. Evaluation of the chemical quality of Sekkoku (石斛) in current Japanese commercial crude drugs: constituents of Flickingeria xantholeuca (Rchb. f.) A.D. Hawkes. J Nat Med 71, 238–248 (2017). https://doi.org/10.1007/s11418-016-1054-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-016-1054-5

Keywords

Search

Navigation