Journal of Natural Medicines

, Volume 71, Issue 1, pp 238–248 | Cite as

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

  • Mei Muto
  • Haruka Asahina
  • Tatsufumi Yoshioka
  • Kazuo Ozaki
  • Makio Shibano
Original Paper


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 (13), 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.


ent-Pimarane-type diterpene ent-Kaurane-type diterpene Glycoside Flickingeria xantholeuca Orchidaceae TLC LC/MS 



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.


  1. 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 12:341–367CrossRefGoogle Scholar
  2. 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 93:1795–1803CrossRefPubMedGoogle Scholar
  3. 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 29:841752Google Scholar
  4. 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):593–598CrossRefGoogle Scholar
  5. 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 61:112–115CrossRefGoogle Scholar
  6. 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 117:400–409CrossRefPubMedGoogle Scholar
  7. 7.
    Hsu TC, Chung SW, Kuo CM (2012) Supplements to the Orchid flora of Taiwan. Taiwania 57(3):271–277Google Scholar
  8. 8.
    Snatzke G (1965) Circular dichroism. VIII. Modification of the octant rule for α, β-unsaturated ketones: theory. Tetrahedron 21:413–419CrossRefGoogle Scholar
  9. 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 61:152–155CrossRefPubMedGoogle Scholar
  10. 10.
    Tinto WF, Blyden G, Reynolds WF, McLean S (1991) Diterpene and anthraquinone constituents of Glycydendron amazonicum. J Nat Prod 54(4):1127–1130CrossRefGoogle Scholar
  11. 11.
    Liu G, Müller R, Rüedi P (2003) Chemical transformations of Phyllocladane (=13β-kaurane) diterpenoids. Helv Chem Acta 86:420–438CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan 2016

Authors and Affiliations

  1. 1.Osaka University of Pharmaceutical SciencesTakatsukiJapan
  2. 2.National Defense Medicinal CollegeTokorozawaJapan
  3. 3.Research Institute of Medicinal Plant ResourcesShinnihonseiyaku Co., Ltd.IwakuniJapan

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