Skip to main content
SpringerLink
Log in

Tetrahydroxanthones from Mongolian medicinal plant Gentianella amarella ssp. acuta

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

Abstract

Two tetrahydroxanthones, 1,3,5S,8S-tetrahydroxy-5,6,7,8-tetrahydroxanthone (1) and 1,3,5R,8S-tetrahydroxy-5,6,7,8-tetrahydroxanthone (2), and six new tetrahydroxanthone glycosides, amarellins A–F (3–8), were isolated from the aerial parts of a Mongolian medicinal plant Gentianella amarella ssp. acuta (Gentianaceae). The structures of 1–8 were elucidated on the basis of spectroscopic analysis, chemical conversion, and ECD calculation. Amarellins A–C (3–5) were assigned as 8-O-β-d-glucoside, 8-O-β-d-xyloside, and 1-O-β-d-glucoside of 1, respectively, while amarellins D–F (6–8) were elucidated to be 8-O-β-d-xyloside, 1-O-β-d-glucoside, and 3-O-β-d-glucoside of 2, respectively.

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

  1. Struwe L (2014) Classification and evolution of the family Gentianaceae. In: Rybczyński JJ, Davey MR, Mikula A (eds) The Gentianaceae. Characterization and ecology, vol 1. Springer, Berlin, pp 13–35

    Chapter  Google Scholar 

  2. Li MH, Zhou LS, Fang HY, Song XL, Zhang N (2010) Quantification of xanthones in a Mongolian health tea using high-performance liquid chromatography. J Med Plants Res 4:1704–1707

    CAS  Google Scholar 

  3. Lv LJ, Li MH (2009) Terpenoids, flavonoids and xanthones from Gentianella acuta (Gentianaceae). Biochem Syst Ecol 37:497–500

    Article  CAS  Google Scholar 

  4. Tanaka N, Takekata M, Kurimoto SI, Kawazoe K, Murakami K, Damdinjav D, Dorjbal E, Kashiwada Y (2015) Algiolide A, secoiridoid glucoside from Mongolian medicinal plant Gentiana algida. Tetrahedron Lett 56:817–819

    Article  CAS  Google Scholar 

  5. Kaldas M, Miura I, Hostettmann K (1978) Campestroside, a new tetrahydroxanthone glucoside from Gentiana campestris. Phytochemistry 17:295–297

    Article  CAS  Google Scholar 

  6. Zhou HM, Liu YL, Blaskó G, Cordell GA (1989) Swertiabisxanthone-I from Swertia macrosperma. Phytochemistry 28:3569–3571

    Article  CAS  Google Scholar 

  7. Urbain A, Marston A, Sintra Grilo L, Bravo J, Purev O, Purevsuren B, Batsuren D, Reist M, Carrupt PA, Hostettmann K (2008) Xanthones from Gentianella amarella ssp. acuta with acetylcholinesterase and monoamine oxidase inhibitory activities. J Nat Prod 71:895–897

    Article  CAS  PubMed  Google Scholar 

  8. Ishimaru K, Sudo H, Satake M, Matsunaga Y, Hasegawa Y, Takemoto S, Shimomura K (1990) Amarogentin, amaroswerin and four xanthones from hairy root cultures of Swertia japonica. Phytochemistry 29:1563–1565

    Article  CAS  Google Scholar 

  9. Tomimori T, Komatsu M (1969) Studies on the constituents of Swertia japonica. VI. On the flavonoid and xanthone constituents of Swertia randaiensis. Hayata and S. swertopsis Makino. Yakugaku Zasshi 89:1276–1282

    CAS  PubMed  Google Scholar 

  10. Faizi S, Zikr-ur-Rehman S, Ali M, Naz A (2006) Temperature and solvent dependent NMR studies on mangiferin and complete NMR spectral assignments of its acyl and methyl derivatives. Magn Reson Chem 44:838–844

    Article  CAS  PubMed  Google Scholar 

  11. Inouye H, Ueda S, Nakamura Y (1966) Structure of sweroside, a new glucoside from Swertia japonica. Tetrahedron Lett 7:5229–5234

    Article  Google Scholar 

  12. Kubota T, Tomita Y (1961) The structure of swertiamarin. Tetrahedron Lett 2:176–182

    Article  Google Scholar 

  13. Ikeshiro Y, Tomita Y (1984) A new iridoid glucoside of Swertia japonica. Planta Med 50:485–488

    Article  CAS  PubMed  Google Scholar 

  14. Kizu H, Shimana H, Tomimori T (1995) Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc. Chem Pharm Bull 43:2187–2194

    Article  CAS  PubMed  Google Scholar 

  15. Hase K, Li J, Basnet P, Xiong Q, Takamura S, Namba T, Kadota S (1997) Hepatoprotective principles of Swertia japonica Makino on d-galactosamine/lipopolysaccharide-induced liver injury in mice. Chem Pharm Bull 45:1823–1827

    Article  CAS  PubMed  Google Scholar 

  16. Du XG, Wang W, Zhang QY, Cheng J, Avula B, Khan IA, Guo DA (2012) Identification of xanthones from Swertia punicea using high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 26:2913–2923

    Article  CAS  PubMed  Google Scholar 

  17. Wang QH, Bao B, Chen YL (2014) Structure elucidation and NMR assignments of two unusual xanthones from Lomatogonium carinthiacum (Wulf) Reichb. Magn Reson Chem 52:37–39

    Article  PubMed  Google Scholar 

  18. Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I (2007) Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull 55:899–901

    Article  CAS  PubMed  Google Scholar 

  19. Du XG, Wang W, Zhang SP, Pu XP, Zhang QY, Ye M, Zhao YY, Wang BR, Khan IA, Guo DA (2010) Neuroprotective xanthone glycosides from Swertia punicea. J Nat Prod 73:1422–1426

    Article  CAS  PubMed  Google Scholar 

  20. Zhou NJ, Geng CA, Huang XY, Ma YB, Zhang XM, Wang JL, Chen JJ (2015) Anti-hepatitis B virus active constituents from Swertia chirayita. Fitoterapia 100:27–34

    Article  CAS  PubMed  Google Scholar 

  21. Spartan’10, Wavefunction Inc., Irvine, CA

  22. Gaussian 09, Revision C.01, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski, JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2010) Gaussian, Inc., Wallingford, CT

  23. Bruhn T, Schaumlöffel A, Hemberger Y, Bringmann G (2013) SpecDis, version 1.61. University of Würzburg, Germany

    Google Scholar 

Download references

Acknowledgments

This work was partly supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

Author information

Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima, 770-8505, Japan

    Shuangxin Lu, Naonobu Tanaka, Kazuyoshi Kawazoe & Yoshiki Kashiwada

  2. Graduate School of Bioscience and Bioindustry, Tokushima University, Tokushima, 770-8513, Japan

    Naonobu Tanaka

  3. Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, 862-0082, Japan

    Kotaro Murakami

  4. School of Pharmaceutical Biomedical Sciences, Mongolian National University of Medical Sciences, Ulaanbaatar, 14210, Mongolia

    Davaadagva Damdinjav & Enkhjargal Dorjbal

Authors
  1. Shuangxin Lu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Naonobu Tanaka
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kazuyoshi Kawazoe
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kotaro Murakami
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Davaadagva Damdinjav
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Enkhjargal Dorjbal
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yoshiki Kashiwada
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yoshiki Kashiwada.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lu, S., Tanaka, N., Kawazoe, K. et al. Tetrahydroxanthones from Mongolian medicinal plant Gentianella amarella ssp. acuta . J Nat Med 70, 780–788 (2016). https://doi.org/10.1007/s11418-016-1015-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-016-1015-z

Keywords

Search

Navigation