Journal of Natural Medicines

, Volume 72, Issue 1, pp 347–356 | Cite as

New 8,12;8,20-diepoxy-8,14-secopregnane hexa- and hepta-glycosides from the roots of Asclepias tuberosa

  • Tsutomu WarashinaEmail author
  • Toshio Miyase


Previously, phytochemical investigation of the roots of Asclepias tuberosa (Asclepiadaceae) led to the isolation of some 8,12;8,20-diepoxy-8,14-secopregnane tri-, tetra-, and penta-glycosides. An additional eight new minor 8,12;8,20-diepoxy-8,14-secopregnane glycosides were afforded in the recent investigation of this plant. These glycosides consisted of six or seven 2,6-dideoxy-hexopyranoses together with the aglycone, tuberogenin. The structures of each of these compounds were established using NMR, mass spectroscopic analysis and chemical evidence. As 8,12;8,20-diepoxy-8,14-secopregnane-type glycosides were observed only in A. tuberosa, these compounds were considered to be characteristic phytochemicals of this plant.


Asclepias tuberosa Asclepiadaceae 8,12;8,20-diepoxy-8,14-seco-pregnane glycoside Tuberoside 


Compliance with ethical standards

Conflict of interest

No potential conflict of interest was reported by the authors.

Supplementary material

11418_2017_1155_MOESM1_ESM.doc (1.1 mb)
Supplementary material 1 (DOC 1142 kb)
11418_2017_1155_MOESM2_ESM.docx (361 kb)
Supplementary material 2 (DOCX 361 kb)
11418_2017_1155_MOESM3_ESM.docx (107 kb)
Supplementary material 3 (DOCX 107 kb)
11418_2017_1155_MOESM4_ESM.doc (59 kb)
Supplementary material 4 (DOC 59 kb)


  1. 1.
    Abe F, Mohri Y, Yamauchi T (1991) 3′-epi-19-Norafroside and 12β-hydroxycoroglaucigenin from Asclepias currasavica. Chem Pharm Bull 39:2709–2711CrossRefGoogle Scholar
  2. 2.
    Abe F, Mohri Y, Yamauchi T (1992) Cardenolide glycosides from the seeds of Asclepias curassavica. Chem Pharm Bull 40:2197–2920Google Scholar
  3. 3.
    Abe F, Yamauchi T (2000) An androstane bioside and 3′-thiazolidinone derivatives of doubly-linked cardenolide glycosides from the roots of Asclepias tuberosa. Chem Pharm Bull 48:991–993CrossRefGoogle Scholar
  4. 4.
    Cheung HTA, Watson TP, Seiber JN, Nelson CJ (1980) 7β,8β-Epoxycardenolide glycosides of Asclepias eriocarpa. J Chem Soc Perkin Trans 1:2169–2173CrossRefGoogle Scholar
  5. 5.
    Cheung HTA, Chiu FCK, Watson TR, Wells RJ (1983) Cardenolide glycosides of the Asclepiadaceae. Glycosides from Asclepias fruticosa and the stereochemistry of uscharin, voruscharin and calotoxin. J Chem Soc Perkin Trans 1:2827–2835CrossRefGoogle Scholar
  6. 6.
    Cheung HTA, Nelson CJ, Watson TR (1988) Glucoside conjugates and other cardenolide glycosides from the monarch butterfly reared on Asclepias fruticosa L. J Chem Soc Perkin Trans 1:1851–1857CrossRefGoogle Scholar
  7. 7.
    Cheung HTA, Watson TP (1980) Stereochemistry of the hexosulose in cardenolide glycosides of the Asclepiadaceae. J Chem Soc Perkin Trans 1:2162–2168CrossRefGoogle Scholar
  8. 8.
    Cheung HTA, Nelson CJ (1989) Cardenolide glycosides with 5,6-unsaturation from Asclepias vestita. J Chem Soc Perkin Trans 1:1563–1570CrossRefGoogle Scholar
  9. 9.
    Brower LP (1969) Ecological chemistry. Sci Am 220:22–29CrossRefGoogle Scholar
  10. 10.
    Brower LP, Brower JVZ, Corvino JM (1967) Plant poisons in a terrestrial food chain. Proc Natl Acad Sci USA 57:893–898CrossRefGoogle Scholar
  11. 11.
    Brower LP, Ryerson WN, Coppinger LL, Glazier SC (1968) Ecological chemistry and the palatability spectrum. Science 161:1349–1350CrossRefGoogle Scholar
  12. 12.
    Warashina T, Noro T (1994) Steroidal glycosides from Asclepias fruticosa L. Chem Pharm Bull 42:322–326CrossRefGoogle Scholar
  13. 13.
    Warashina T, Noro T (2000) Cardenolide and oxypregnane glycosides from the roots of Asclepias incarnate L. Chem Pharm Bull 48:516–524CrossRefGoogle Scholar
  14. 14.
    Warashina T, Noro T (2008) Steroidal glycosides from the roots of Asclepias curassavica. Chem Pharm Bull 56:315–322CrossRefGoogle Scholar
  15. 15.
    Abe F, Mohri Y, Okabe H, Yamauchi T (1994) Steroidal constituents from the roots and stems of Asclepias fruticosa. Chem Pharm Bull 42:1777–1783CrossRefGoogle Scholar
  16. 16.
    Abe F, Yamauchi T (2000) Pregnane glycosides from the roots of Asclepias tuberosa. Chem Pharm Bull 48:1071–1072Google Scholar
  17. 17.
    Hatani A, Okumura Y, Maeda H (2004) Cell activator containing extract of Asclepias plant of Asclepiadaceae family, and the skin care preparation for external use. Jpn Kokai Tokkyo Koho: JP 2004-137161 AGoogle Scholar
  18. 18.
    Kikuchi H, Nakauchi R, Yoshida H, Yagi K (2008) The moisturizer, the antiaging agent, the skin-lightening agent, the antioxidant, the slimming agent, the treatment agent, the arginase active stimulators, and the skin applications. Jpn Kokai Tokkyo Koho JP 2008-255078 AGoogle Scholar
  19. 19.
    Warashina T, Umehara K, Miyase T, Noro T (2011) 8,12:8,20-Diexopy-8,14-secopregnane glycosides from the roots of Asclepias tuberosa and their effect on proliferation of human skin fibroblasts. Phytochemistry 72:1865–1875CrossRefGoogle Scholar
  20. 20.
    Warashina T, Noro T (2009) 8,14-secopregnane glycosides from the aerial parts of Asclepias tuberosa. Phytochemisty 70:1294–1304CrossRefGoogle Scholar
  21. 21.
    Kasai R, Okihara M, Asakawa J, Mizutani K, Tanaka O (1979) 13C NMR study of α- and β-anomeric pairs of d-mannopyranosides and l-rhamnopyranosides. Tetrahedron 35:1427–1432CrossRefGoogle Scholar
  22. 22.
    Warashina T, Noro T (2010) 8,12:8,20-Diexopy-8,14-secopregnane glycosides from the aerial parts of Asclepias tuberosa. Chem Pharm Bull 58:172–179CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan KK, part of Springer Nature 2017

Authors and Affiliations

  1. 1.School of Food and Nutritional SciencesUniversity of ShizuokaShizuokaJapan
  2. 2.School of Pharmaceutical SciencesUniversity of ShizuokaShizuokaJapan

Personalised recommendations