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Cardiac glycosides of theCheiranthus allioni. XII

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Abstract

The seeds ofCheiranthus allioni hort. have yielded three new cardenolides the structures of which have been established and which have been named as 4-dehydrosarmentogenin (II), 4-dehydrosarmentogenin rhamnoside (I), and 4-dehydrosarmentogenin rhamnoglucoside (IV). (II) — C23H32O5. m.p. 296–302°, [α] D 20 +26.2±3° (in pyridine) is 3β,11α,14-trihydroxy-14β-card-4,20(22)-dienolide. (I) C29-H42O9, m.p. 268–275°, [α] D 20 −38.2±3° (chloroform-ethanol) is 11α,14-dihydroxy-3β-α-L-rhamnopyranosyloxy-14β-card-4,20(22)-dienolide.(IV) C35H52O14, [α] D 20D −44.1±3° (methanol), is 3β-(4′-O-β-D-glucopyranosyl-α-L-rhamnopyranosyloxy)-14β-card-4, 20(22)-dienolide. An independent synthesis of 4-dehydrosarmentogenin (II) has been carried out, starting from 3β,5,11α,14-tetrahydroxy-5β,14β-card-20(22)-enolide, which has confirmed its structure.

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Additional information

For Communication XI, see [1].

All-Union Scientific-Research Drug Institute, Kharkov. Kharkov State Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 119–125, January–February, 1987.

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Makarevich, I.F., Pavlii, A.I. & Makarevich, S.I. Cardiac glycosides of theCheiranthus allioni. XII. Chem Nat Compd 23, 101–105 (1987). https://doi.org/10.1007/BF00602469

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Keywords

  • Methanol
  • Organic Chemistry
  • Pyridine
  • Glycoside
  • Cardiac Glycoside