Abstract:The antiproliferative and antimicrobial effects of thirteen compounds isolated from Inula viscosa (L.) were tested in this study. The antiproliferative activity was tested against three cell lines using the MTT assay. The microdilution method was used to study the antimicrobial activity against two Gram positive bacteria, two Gram negative bacteria and one fungus. The apoptotic activity was determined using a TUNEL colorimetric assay. Scanning electron microscopy was used to study the morphological changes in treated cancer cells and bacteria. Antiproliferative activity was observed in four flavonoids (nepetin, 3,3′-di-O-methylquercetin, hispidulin, and 3-O-methylquercetin). 3,3′-di-OMethylquercetin and 3-O-methylquercetin showed selective antiproliferative activity against MCF-7 cells, with IC 50 values of 10.11 and 11.23 µg/mL, respectively. Both compounds exert their antiproliferative effect by inducing apoptosis as indicted by the presence of DNA fragmentation, nuclear condensation, and formation of apoptotic bodies in treated cancer cells. The antimicrobial effect of Inula viscosa were also noticed in 3,3′-di-O-methylquercetin and 3-O-methyquercetin that inhibited Bacillus cereus at MIC of 62.5 and 125 µg/mL, respectively. Salmonella typhimurium was inhibited by both compounds at MIC of 125 µg/mL. 3,3′-di-O-Methylquercetin induced damage in bacterial cell walls and cytoplasmic membranes. Methylated quercetins isolated from Inula viscosa have improved anticancer and antimicrobial properties compared with other flavonoids and are promising as potential anticancer and antimicrobial agents.

Colchicum ritchii of Jordanian origin has yielded the diphenolic phenethyltetrahydroisoquinoline (-)-isoautumnaline [2], which is the first naturally occurring analog of the known (-)-autumnaline [1]. The absolute configuration of both alkaloids was established through a study of their cd spectra. Two new colchicine-type alkaloids are (-)-specioritchine[5] and its structural isomer (-)-speciocolchine [6]. Androcymbine, which was previously known only in the levorotatory form, has now been found as the dextrorotatory enantiomer 7. It is accompanied in the plant by the related base (+ )-colchiritchine {8}.Initial investigations on Colchicum ritchii R. Br. (Liliaceae) had revealed the presence of ( -)-colchicine [3], ( -)-N-formyldeacetylcolchicine, (-)-demecolcine, ( -)-colchiceine, and a compound believed to be either (-)-2or (-)-3-demethylcolchicine (1-3).Presently, we were able to collect this plant in southern Jordan, and the study of its alkaloidal content yielded a variety of alkaloids belonging to the autumnaline [1], colchicine [3], and androcymbine [4} series. With the exception of (-)-autumnaline [1] and (-)-isoautumnaline [2], Tables 1 and 2 list the alkaloids isolated and characterized by us, together with their 'H-nmr chemical shifts obtained at either 200 or 360 MHz in CDC13 solution. Chemical shift assignments were confirmed through appropriate decoupling and nOe experiments.Because the present work represents our initial effort in the realm of Colchicum alkaloids, and because we did not possess in our alkaloidal collection samples of such compounds for comparison purposes, with the single exception of the commercially available ( -)-colchicine [3], we endeavored first to obtain complete high resolution nmr data for the known alkaloids we had isolated. Subsequently, this information was used in the characterization of five new alkaloids found in the plant.Our first new alkaloid was the diphenolic phenethyltetrahydroisoquinoline (-)isoautumnaline [2], C21H27NO5, which was obtained mixed with the known structur-1 R,=Me, R2 = H 2 R1=H,R2=Me('Hnmr

Four new and 14 known compounds have been isolated from Inula viscosa of Jordanian origin. The new isolates are 11(13)-eudesmen-12-oic acids, 3beta-hydroxyilicic acid (1), 3alpha-hydroxy-epi-ilicic acid (2), 2alpha-hydroxyilicic acid (3) and 9beta-hydroxy-2-oxoisocostic acid (4).

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Polyalthia acuminata Thw. (Annonaceae) has furnished the new aporphines (-)-norliridinine ( 1), (-)-3-hydroxynomuciferine (2), (-)-norannuradhapurine (9), and (-)-noroliveroline (11). Monophenolic aporphines bearing the phenol group at C-3 exhibit both a bathochromic shift as well as hyperchromic effect in their uv spectra in basic solution. Ar-Methylation of 1 yields (-)-liridinine, which is thus firmly represented by expression 7. Similar treatment of 2 leads to (-)-3-hydroxynuciferine (8) which is identical with the alkaloid (-)-lirinine. This last transformation establishes with certainty the position of the phenol in (-)lirinine.