Cytotoxic Coumarins fromMammea harmandii

Abstract

Two new naturally occurring coumarins, isomesuol (1) and mammearin A (2), together with nine known Mammea coumarins 3-11 were isolated from the EtOAc extract of the leaves and twigs of Mammea harmandii. Coumarins 1, 3 and 4 showed cytotoxicity against a panel of mammalian cancer cell lines. Their structures were determined by spectroscopic methods. The assignments of 13C-NMR signals of isomesuol (1), which was isolated for the first time as a natural product, have been revised.

Cytotoxic 4-Phenylcoumarins from the Leaves of Marila pluricostata

“…Coumarins 4 − 17 were identified as known mammeisin (mammea A/AA) ( 4 ), , isomammeisin (mammea A/BA) ( 5 ), mammeigin (mammea A/AA cyclo D) ( 6 ), , MAB 5 (mammea A/AB cyclo D) ( 7 ), mesuagin (mammea A/AD cyclo D) ( 8 ), isomesuol ( 9 ) MAB 1 (mammea A/AB) ( 10 ), mesuol (mammea A/AD) ( 11 ), (mammea A/BB) ( 12 ), , isodispar B ( 13 ), cyclomammeisin (mammea A/AA cyclo F) ( 14 ), , disparinol A ( 15 ), MAB 3 (mammea A/AB cyclo F) ( 16 ), and mesuol cyclo F (mammea A/AD cyclo F) ( 17 ), through the complete analysis of their NMR and MS data and comparison with those reported in the literature for these compounds. 13 C NMR data for compounds 5 , 10 , and 17 were not reported before and have, therefore, been included in this paper (Table ).…”

“…Finally, fraction J, chromatographed over silica gel using CH 2 Cl 2 /MeOH (1:1), afforded coumarins 1 (27 mg, 0.014%) and 3 (15.3 mg, 0.0082%). Phenylcoumarins 4 − 17 were identified by comparison of their spectroscopic data with those reported in the literature. − …”

Lepidotol A from Mesua lepidota Inhibits Inflammatory and Immune Mediators in Human Endothelial Cells

“…An HMBC correlation between the carbon at δ C 62.3 and both H-1″a and H-1″b suggested the geminal disposition of the two prenyl groups at the C-6 quaternary carbon (Figure S3, Supporting Information). The 1 H and 13 C NMR spectra also showed two methyls at δ H 1.31 (6H, d, J = 6.7 Hz, Me-3‴ and Me-4‴), a methine proton at δ H 3.98 (1H, sept, J = 6.7 Hz, H-2‴), and a carbonyl carbon at δ C 205.2 (C-1‴), which indicated the presence of an isobutyryl group . The HMBC spectrum exhibited correlations between the hydrogen-bonded hydroxy (δ H 18.89) and the carbons at δ C 62.3 (C-6), 104.6 (C-8), 200.4 (C-5), and 205.2 (C-1‴).…”

Neoflavonoids as Inhibitors of HIV-1 Replication by Targeting the Tat and NF-κB Pathways

“…The neoflavonoids with anti-HIV activity possessing 4-phenylcoumarin skeleton have been obtained mainly from Calophyllaceae family that includes the genera: Calophyllum [ 15 , 16 , 17 , 18 , 19 , 20 , 21 ]; Mammea [ 21 , 22 , 23 , 24 , 25 , 26 ]; Mesua [ 27 , 28 , 29 , 30 , 31 , 32 , 33 ]; Kielmeyera [ 34 , 35 , 36 , 37 , 38 ]; and Marila [ 39 ], from which several 4-phenyl chromen-2-one derivatives have been isolated.…”