Cacalolides from Senecio barba‐johannis

Abstract

From the roots of Senecio barba-johannis DC, the two new cacalolides 13-acetoxycacalohastin (2) and 13-hydroxy-14-oxocacalohastin (3), together with the known cacalolide 13-acetoxy-14-oxocacalohastin (4) were isolated. Their structures were determined on the basis of chemical and spectroscopic evidence. Complete 1 H and 13 C NMR chemical shift assignments of these compounds were achieved using one-and two-dimensional NMR methods, including gHMQC and gHMBC experiments.

Eremophilanes and Pyrrolizidine Alkaloids of Senecioneae Species

“…The methanol extract of roots of Roldana oaxacana gave the modified eremophilanes 13-acetoxy-14-oxocacalohastin (5) [12], maturin acetate (6) [13], maturone acetate (7) [14], and 13-hydroxy-14-oxocacalohastin (8) [12]. Additionally, β-sitosterol and stigmasterol as a mixture and β-sitosteryl β-D-glucopyranoside were obtained.…”

Chemical and Pharmacological Research on Plants from the Genus Senecio

“…Six new cacalolides 309 -314 were isolated from S. madagascariensis collected in Colombia [87]. From the roots of S. barba-johannis, the two new cacalolides 315 and 316, together with the known cacalolide 317, were isolated [3]. Two Senecio species (S. fuertesii and S. picardae) from the Dominican Republic afforded seven new cacalol derivatives, 318 -322 and 329 -331 [88].…”

“…Some Senecio species have a negative impact in many agricultural countries, because these plants are responsible for more deaths to livestock than any other poisonous plant. The toxicity exhibited by these plants has been attributed to their content of PAs and some furanoeremophilanes [3]. Senecio species were used in the folk medicine for the treatment of wounds and as antiemetic, anti-inflammatory, and vasodilatory preparations [1].…”

Natural sesquiterpenoids

“…Four pairs of new seco-macrotolides 296-299 have been obtained from Ligulariopsis shichuana, 313 whilst the lactone 300 has been found in Inula britannica. 291 A study of the roots of Senecio barba-johannis 314 afforded the two new cacalolides 301 and 302.…”