Antitumor Germacranolides from Anvillea garcinii

Abstract

The aerial parts of Anvillea garcinii yielded two new germacranolides, 9 alpha-hydroxy-1 beta, 10 alpha-epoxyparthenolide (4) and parthenolid-9-one (5), in addition to the known 9 alpha-hydroxyparthenolide (1), 9 beta-hydroxyparthenolide (2), and 9 beta-hydroxy-1 beta, 10 alpha-epoxyparthenolide (3). The structures of the new compounds were elucidated from their spectral data (IR, MS, 1H- and 13C-NMR, 1H-1H COSY, and 1H-13C HETCOR) and by chemical derivatization. The hitherto unreported 13C-NMR data and carbon atom assignments of the previously isolated lactones 1, 2, and 3 were given. The in-vitro antitumor and anti-HIV activities were evaluated for the isolated compounds.

cis-Parthenolid-9-one from Anvillea garcinii

“…Previous examination of the aerial parts of the plant afforded five germacranolides9α-hydroxyparthenolide, 9β-hydroxyparthenolide, 9β-hydroxy-1β,10α-epoxyparthenolide, 9α-hydroxy-1β,10α-epoxyparthenolide, and parthenolid-9-one ( 1 ) 4 and two guaianolides, as well as flavonoidal components . The cytotoxic effects of the isolated germacranolides against a panel of approximately 60 human tumor cell lines were reported . We describe herein the isolation and structure determination of a new geometrical isomer of parthenolid-9-one and report the results of in vitro cytotoxicity and in vivo antineoplastic studies.…”

“…Compound 2 was isolated by chromatography of the partially purified CHCl 3 extract of A. garcinii on a Si gel column and further purified using a Chromatotron apparatus. Compound 1 , previously reported from the same plant, was isolated along with 2 . 1 H and 13 C NMR spectral data for 2 were strikingly similar to those of 1 , with only small differences in their chemical shifts, indicating that 2 also has a germacranolide skeleton.…”

“…(Asteraceae) is a wild plant found in areas of the Middle East . Previous examination of the aerial parts of the plant afforded five germacranolides9α-hydroxyparthenolide, 9β-hydroxyparthenolide, 9β-hydroxy-1β,10α-epoxyparthenolide, 9α-hydroxy-1β,10α-epoxyparthenolide, and parthenolid-9-one ( 1 ) 4 and two guaianolides, as well as flavonoidal components . The cytotoxic effects of the isolated germacranolides against a panel of approximately 60 human tumor cell lines were reported .…”

Antibacterial and Antifungal Sesquiterpenoids from Aerial Parts of Anvillea garcinii

“…Traditionally, the dried plant is crushed, mixed with honey or date and olive oil, and used to treat cold symptoms [4]. Flavonoids and sesquiterpene lactones have been the predominant class of secondary metabolites obtained by phytochemical studies on A. garcinii [5][6][7][8][9][10][11]. Our previous investigations on this plant disclosed the presence of sesquiterpene lactones of the guaianolide-and germacranolidetypes, including the corresponding amino acid adducts, as well as some flavonoids glycosides [11][12][13].…”

Voltammetric determination of parthenolide in spiked human plasma and urine

“…Parthenolide (1), a germacranolide sesquiterpene lactone, is the major constituent of European feverfew (Tanacetum parthenium) and several other members of the families Asteraceae and Magnoliaceae . Recently, 1 has attracted considerable attention because of its wide spectrum of biological effects, which include cytotoxic (Abdel-Sattar et al, 1996), antibacterial and anti-fungal (Fischer, 1991) activities. Parthenolide was also found to be the most active germacranolide against Mycobacterium tuberculosis and M. avium (Fischer et al, 1998).…”