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Pregnane glycosides from the bark of Marsdenia cundurango and their cytotoxic activity

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Abstract

Seven new pregnane glycosides (17) and eight known compounds (815) were isolated from the bark of Marsdenia cundurango (Asclepiadaceae). The structures of 17 were determined by spectroscopic analysis, including two-dimension NMR spectroscopy, chemical transformations, and chromatographic analysis of the hydrolyzed products. The isolated compounds 115 were evaluated for their cytotoxic activity against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, and TIG-3 normal human lung cells, including apoptosis-inducing activity of a representative pregnane glycoside in HL-60 cells.

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References

  1. The Ministry of Health, Labour and Welfare, Japan. The Japanese pharmacopoeia, 17th edn (Ministry notification no. 64 of March 7, 2016). The Ministry of Health, Labour and Welfare, Tokyo

  2. Tschesche R, Welzel P, Snatzke G (1965) Digitanolglykoside—XII die constitution von kondurangogenin A, dem aglykon eines esterglykosids der kondurangorinde. Tetrahedron 21:1777–1795

    Article  CAS  Google Scholar 

  3. Tschesche R, Welzel P, Fehlhaber H (1965) Digitanolglykoside—XIII massenspektrometrische untersuchungen am kondurangogenin A. Tetrahedron 21:1797–1807

    Article  CAS  Google Scholar 

  4. Tschesche R, Kohl H, Welzel P (1967) Digitanolglykoside—XVI die struktur der kondurangogenine A und C. Tetrahedron 23:1461–1471

    Article  CAS  Google Scholar 

  5. Tschesche R, Kohl H (1968) Digitanolglykoside-XIX die struktur der kondurangoglykoside A, A1 und C, C1. Tetrahedron 24:4359–4371

    Article  CAS  Google Scholar 

  6. Hayashi K, Wada K, Mitsuhashi H, Bando H, Takase M, Terada S, Koide Y, Aiba T, Narita T, Mizuno D (1980) Antitumor active glycosides from Condurango cortex. Chem Pharm Bull 28:1954–1958

    Article  CAS  Google Scholar 

  7. Hayashi K, Wada K, Mitsuhashi H, Bando H, Takase M, Terada S, Koide Y, Aiba T, Narita T (1981) Further investigation of antitumor condurangoglycosides with C-18 oxygenated aglycone. Chem Pharm Bull 29:2725–2730

    Article  CAS  Google Scholar 

  8. Berger S, Junior P, Kopanski L (1988) Structural revision of pregnane ester glycosides from Condurango cortex and new compounds. Phytochemistry 27:1451–1458

    Article  CAS  Google Scholar 

  9. Umehara K, Endoh M, Miyase T, Kuroyanagi M, Ueno A (1994) Studies on differentiation inducers. Pregnane derivatives from Condurango cortex. Chem Pharm Bull 42:611–616

    Article  CAS  Google Scholar 

  10. Sikdar S, Mukherjee A, Boujedaini N, Khuda-Bukhsh AR (2013) Ethanolic extract of Condurango (Marsdenia condurango) used in traditional systems of medicine including homeopathy against cancer can induce DNA damage and apoptosis in non small lung cancer cells, A549 and H522, in vitro. Tang Humanit Med 3:e9

    Google Scholar 

  11. Sikdar S, Mukherjee A, Ghosh S, Khuda-Bukhsh AR (2014) Codurango glycoside-rich components stimulate DNA damage-induced cell cycle arrest and ROS-mediated caspase-3 dependent apoptosis through inhibition of cell-proliferation in lung cancer, in vitro and in vivo. Environ Toxicol Pharmacol 37:300–331

    Article  CAS  Google Scholar 

  12. Yokosuka A, Mimaki Y, Sashida Y (2002) Steroidal and pregnane glycosides from the rhizomes of Tacca chantrieri. J Nat Prod 65:1293–1298

    Article  CAS  Google Scholar 

  13. Kubo A, Kuroda M, Yokosuka A, Sakagami H, Mimaki Y (2015) Amurensiosides L-P, five new cardenolide glycosides from the roots of Adonis amurensis. Nat Prod Commun 10:27–32

    PubMed  Google Scholar 

  14. Yokosuka A, Iguchi T, Kawahata R, Mimaki Y (2018) Cytotoxic bufadienolides from the whole plants of Helleborus foetidus. Phytochem Lett 23:94–99

    Article  CAS  Google Scholar 

  15. Zhang Y, Yuan J, Ding W (1993) Structural elucidation of marsdeoreophiside A. Zhongcaoyao 24:171–173

    CAS  Google Scholar 

  16. Allgeier H (1968) Struktur der pachybiose und asclepobiose. Helv Chim Acta 51:311–325

    Article  CAS  Google Scholar 

  17. Gupta VS, Kumar A, Deepak D, Khare A, Khare NK (2003) Pregnanes and pregnane glycosides from Marsdenia roylei. Phytochemistry 64:1327–1333

    Article  CAS  Google Scholar 

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Acknowledgements

This work was financially supported in part by the Japan Society for the Promotion of Sciences (JSPS) KAKENHI (Grant number 26860069).

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Correspondence to Akihito Yokosuka.

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Tatsuno, S., Yokosuka, A., Hatsuma, F. et al. Pregnane glycosides from the bark of Marsdenia cundurango and their cytotoxic activity. J Nat Med 73, 93–103 (2019). https://doi.org/10.1007/s11418-018-1248-0

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  • DOI: https://doi.org/10.1007/s11418-018-1248-0

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