cis-Parthenolid-9-one from Anvillea garcinii

Abstract

The cis-isomer (2) of the previously isolated parthenolid-9-one (1) was isolated from Anvillea garcinii and the structures and relative stereochemistries of both were determined from NMR data in combination with single-crystal X-ray analysis. In vitro cytotoxicity and in vivo antitumor activity for both compounds are reported.

Cytotoxic Activity of Germacrane-Type Sesquiterpene Lactones from Dimerostemma aspilioides

“…Other germacranolides with a similar structure to compound 1, including the 4,5epoxide, but with a carbonyl or an acetoxy group at position C-9 and a methyl moiety at C-10 and lacking the side chain attached at C-8, showed cytotoxic effects against a panel of cancer cells, with IC 50 values ranging from 0.67 to 10.5 μM. 28,29 These IC 50 values are comparable to those obtained herein (Table 2), which suggests that both the epoxide C4−C5 and α-methylene-γ-lactone contribute more efficiently to toxicity than the α,β-unsaturated chain at C-8 or the substituents at C-10. The presence of the 4,5-epoxide may explain the higher cytotoxicity displayed by compound 1 in particular compared to compound 2.…”

Centrifugal partition chromatography elution gradient for isolation of sesquiterpene lactones and flavonoids from Anvillea radiata

“…Given the two molecular families (flavonoids and germacranolides) described as present in the selected plant material and the previous extraction methods reported in literature [11][12][13][14][15], chloroform was chosen as extraction solvent to obtain the most selective extraction conditions for germacranolides.…”

“…Conventional procedures (maceration, liquid-liquid extraction, silica gel column chromatography) have been previously used to isolate small amounts of germacranolides from different CHCl 3 extracts of the aerial parts of A. garcinii or A. radiata. The Germacranolides extracted from A. radiata have been identified as 9␣-hydroxyparthenolide [11] 9␤-hydroxyparthenolide [12], 9␤-hydroxy-1␤,10␣-epoxyparthenolide [12], 9␣-hydroxy-1␤,10␣-epoxyparthenolide [13], 8␣,9␣-epoxyparthenolide [14], parthenolid-9-one [13] and cis-parthenolid-9-one [15]. In addition, thirteen minor flavonoids (four aglycones and nine flavonol glycosides), have been reported [16].…”

Antibacterial and Antifungal Sesquiterpenoids from Aerial Parts of Anvillea garcinii

“…The class of Anvillea sesquiterpene lactones is dominated by derivatives with the parthenolide skeleton, germacranolides endowed with significant biological activities in cancer and inflammation, as well as in metabolic disorders [14]. Previous examination of the aerial parts of A. garcinii have afforded several members of the parthenolide class, such as 9α-and 9β-hydroxyparthenolide, 9αand 9β-hydroxy-1β,10α-epoxyparthenolide, parthenolid-9-one, and its cis-isomer [15]. In addition, guaianolide-type sesquiterpenoids, a class of phytochemicals with a broad range of activities, including cytotoxic, antiprotozoal, and anti-inflammatory potential [16], also constitute prominent A. garcinii metabolites.…”