seco-Pregnane Glycosides from Australian Caustic Vine (Cynanchum viminalesubsp. australe)

Autor: Xue, Yongbo, Savchenko, Andrei I., Agnew-Francis, Kylie A., Miles, Jared A., Holt, Tina, Lu, Hieng, Chow, Sharon, Forster, Paul I., Boyle, Glen M., Ross, Benjamin P., Fischer, Katja, Kutateladze, Andrei G., Williams, Craig M.
Zdroj: Journal of Natural Products; March 2023, Vol. 86 Issue: 3 p490-497, 8p
Abstrakt: Cynanchum viminalesubsp. australe, more commonly known as caustic vine, is a leafless succulent that grows in the northern arid zone of Australia. Toxicity toward livestock has been reported for this species, along with use in traditional medicine and its potential anticancer activity. Disclosed herein are novel seco-pregnane aglycones cynavimigenin A (5) and cynaviminoside A (6), together with new pregnane glycosides cynaviminoside B (7) and cynavimigenin B (8). Cynavimigenin B (8) contains an unprecedented 7-oxobicyclo[2.2.1]heptane moiety in the seco-pregnane series, likely arising from a pinacol-type rearrangement. Interestingly, these isolates displayed only limited cytotoxicity in cancer and normal human cell lines, in addition to low activity against acetylcholinesterase and Sarcoptes scabieibioassays, suggesting that 5–8are not associated with the reported toxicity of this plant species.
Databáze: Supplemental Index