Three new and two rare furanoeremophilanes from senecio asirensis

Abstract

Three new furanoeremophilanes have been obtained from the aerial parts of Senecio asirensis (N. O. Asteraceae), and characterized as 6-hydroxylmethyl-9-methoxyl-4,11-dimethylnaphtho[2,3-b]furan, designated asirensane-a (1), 6-hydroxyl-1,2-dimethoxyl-4,6,11-trimethyl-6-hydronaphtho[2,3-a]furan-7-one, named asirensane-b (2), and (6,12-dihydroxyl-9-methoxyl-4-methyl-11-acetyl-3,4-dihydronaphtho[2,3-b]furan- 3-yl)methyl (2'Z)-2'-methyl-but-2'-enoate, designated asirensane-c (3). In addition, two rare furanoeremophilanes have also been isolated and characterized from this source, namely 9-methoxyl-4,11-dimethylnaphtho[2,3-b]furan, named 14-nordehydro-calohastine (4), and 4,11-dimethylnaphtho[2,3-b]furan-6,9-dione, designated as maturinone (5). Their structures have been elucidated on the basis of spectral analysis. The alcoholic extract was also tested for anti-inflammatory activity, which decreased edema by 22% at a dose of 500 mg kg-1 after 3 h with respect to the control group treated only with carrageenan, while the standard drug phenylbutazone showed a 50% decrease at a dose of 100 mg kg-1, indicating that the extract has moderate anti-inflammatory activity.

Eremophilanes from Senecio mairetianus and Some Reaction Products

“…The relative stereochemistry of C-5 and C-10 was deduced from the chemical shift of CH [3][4][5][6][7][8][9][10][11][12][13][14]15 which indicated the trans-decalin system of mairetolide A (1). The COSY spectrum showed cross peaks of CH 3 -13 with H-6R (δ 2.21) and H-8 (δ 4.91), which suggested dihedral angles of about 90°for H-6R and H-8 with the double bond of C-7 (11), thus indicating an R-orientation for H-8.…”

“…The genus Senecio (Asteraceae) is considered poisonous since some of its species have been reported to be toxic to livestock and humans . This toxicity has been attributed to pyrrolizidine alkaloids, which, together with eremophilanes, are the most widespread secondary metabolites reported in the genus. − Studies have shown that pyrrolizidine alkaloids of the retronecine, heliotridine, and otonecine types are carcinogenic, genotoxic, mutagenic, and teratogenic. ,, Some eremophilanes have presented antifungal, anti-inflammatory, antihyperglycemic, cytotoxic, and antimicrobial activities. − …”

Phytochemical Composition and Cytotoxic Activity of Senecio asirensis Hexane Fraction Using In Vitro and In Silico Approaches

“…14 These species produce furanoeremophilanes, which are commonly isolated and characterized for their medicinal purposes. 15 Additionally, certain Senecio species exhibit gastroprotective effects and have been employed in the treatment of sexually transmitted infections. 16 This study aims to evaluate the antibacterial and cytotoxic properties of the methanol extract and fractions obtained from the aerial parts of S. asirensis.…”

“…14 These species produce furanoeremophilanes, which are commonly isolated and characterized for their medicinal purposes. 15 Additionally, certain Senecio species exhibit gastroprotective effects and have been employed in the treatment of sexually transmitted infections. 16…”