Abdurazag A. Auzi

Antiinflammatory sesquiterpenes from the root oil of Ferula hermonis

Ferula hermonis Boiss. (Apiaceae), commonly known as ‘Shilsh‐el‐zallouh’, ‘Hashishat‐al‐kattira’ or ‘The Lebanese viagra’, is a small shrub that grows abundantly on the Hermon Mountain between Syria and Lebanon. The seeds and roots of this plant have long been used in the Middle East as an aphrodisiac, and for the treatment of frigidity and impotence for both men and women. The antiinflammatory properties of three major daucane esters, ferutinin (1) teferin (2) and teferidin (3), isolated from the root oil of Ferula hermonis, were assessed by the carrageenan‐induced oedema model in rats. The antiinflammatory effect of both 1 and 2 was observed with a dose of 100 mg/kg, while compound 3 did not show any antiinflammatory activity; conversely it produced a significant proinflammatory effect 2 and 3 h after carrageenan injection. Copyright

Feruhermonins A–C: three daucane esters from the seeds of Ferula hermonis (Apiaceae)

Seventeen daucane esters have been isolated from the seeds of Ferula hermonis Boiss (Apiaceae). Three of these sesquiterpenes, 4β-hydroxy-6α-benzoyl-7-daucen-9-one (1), 4β, 8β-dihydroxy-6α-benzoyl-dauc-9-ene (2), and 4β, 9α-dihydroxy-6α-benzoyl-dauc-7-ene (4), named feruhermonins A–C, respectively, are novel natural products. The structures of these compounds were elucidated unequivocally by a series of 1D and 2D NMR analyses. Although 4β, 8β-dihydroxy-6α-(4-hydroxy-3-methoxybenzoyl)-dauc-9-ene (3) was reported previously, the complete spectroscopic data for this compound are presented here for the first time.

Distribution of flavonoids, alkaloids, acetophenones and phloroglucinols in the genus Bosistoa (Rutaceae)

The leaves of six of the seven species currently assigned to the Australian genus Bosistoa (Rutacea) have been examined. Major groups of metabolites isolated were flavones and flavanones, 1,3,5-oxygenated acridone alkaloids phloroglucinols and acetophenones, all of which are further modified by the addition of 5-carbon prenyl substituents. In a recent revision Bosistoa was divided into two groups and the distribution of flavonoid aglycones is found to coincide with Group II while species in Group 1 yield acridones, phloroglucinols and acetophenones. It is suggested that secondary metabolite production in Bosistoa is best rationalized by considering a central triketide or tetraketide which through either internal cyclization (phloroglucinols, acetophenones) or condensation with anthranilic acid (acridone alkaloids) or cinnamic acids (flavonoids) can give rise to all major groups of metabolites.

Acridone alkaloids from Bosistoa transversa

Abstract Eight acridone alkaloids were isolated from Bosistoa transversa . Three of them are novel and have been identified as 1,3,5-trihydroxy-2-(2ξ-hydroxy-3-methylbut-3-enyl)-10-methylacridan-9-one (trivial name, bosistidine), 1,3,5-trihydroxy-2-(2ξ-hydroxy-3-methylbut-3-enyl)-4-(3-methylbut-2-enyl)-10-methylacridan-9-one (bosistine) and 1,3,5-trihydroxy-4-(2ξ-hydroxy-3-methylbut-3-enyl)-yukocritine. The structures were elucidated on the basis of NMR spectral data, notably NOESY and HMBC experiments.

A xanthine alkaloid from the leaves of Bosistoa floydii

Abstract A novel xanthine alkaloid and two known flavonoids have been isolated from the leaves of Bosistoa floydii and identified as 1,3-di(3-methylbut-2-enyl)-7-methylxanthine, 5,4′-dihydroxy-3,7,3′-trimethoxyflavone and 5-hydroxy-3,3′,4′,5′,7-pentamethoxyflavone.

Phloroglucinol derivatives from leaves of Bosistoa pentacocca

Abstract Leaves from four collections of Bosistoa pentacocca , two of the variety connaricarpa and one each of the type variety and var. dryanderensis , have been examined. In each, the major metabolite isolated was characterized as 2-(3,7-dimethyloct-2.5-dienyl)-6-(3-methylbut-2-enyl)phloroglucinol-1-acetate (trivial name pentacoccol). Four other pentacoccol derivatives were obtained as minor components, pentacoccol-5-methyl ether(from var. pentacocca and var. dryanderesis , 2,2-dimethyl-3ξ, 7-dihydroxy-5-acetoxy-6-(3,7-dimethyloct-2,5-dienyl-3,4-dihydrobenzo-[2 H ]-pyran (3′-hydroxydihydropyranopentacoccol from var. connaricarpa ), 2′-(1 -hydroxy-1-methylethyl)-4-acetoxy-5-(3,7-dimethyloct-2,5-dienyl)-6-hydroxybenzo-[2 H ]-furan (2′-(1-hydroxyosopropyl) furanopentacoccol from var. pentacocca and 4-acetoxy-5-(3,7-dimethyloct-2,5-dienyl)-6-hydroxybenzo-[2 H ]-furan (furanopentacoccol from var. dryanderensis . All compounds were identified on the basis of their spectroscopic data.

Novel Prenylated Acetophenones from Bosistoa selwynii

Abstract From the aerial parts of Bosistoa selwynii (Rutaceae) four novel prenylated acetophenones were isolated and identified as pyranoselwynone (5-hydroxy-6-acetyl-{6,6-dimethyl-5ξ-hydroxy-4,5-di-hydropyrano}-[3,2-h]-2,2-dimethylbenzopyran), selwynone (5,7-dihydroxy-6-acetyl-8-(3-methylbut-2-enyl)-3,4-dihydro-2,2-dimethyl-3ξ-hydroxypyran), furanoselwynone (5-hydroxy-6-acetyl-{5-[1-hydroxy-1-methylethyl]-4,5-dihydro-furano}-[3,2-h]-2,2-dimethylpyran), and isofurano-selwynone (7-hydroxy-8-acetyl-{5-[1-hydroxy-1-methylethyl]-4,5-dihydrofurano}-[3,2-f]-2,2-dimethylpyran). Other compounds isolated were a series of eight acridone alkaloids (reported on previously), the coumarins scopoletin and braylin and the triterpenes lupeol and β-amyrin. The structures of the new acetophenones were elucidated on the basis of NMR spectral data.