Novel Acetogenins from the Leaves ofDasymaschalon sootepense

Abstract

The hexane extract from the leaves of Dasymaschalon sootepense Craib (Annonaceae) showed strong cytotoxic activity against the L1210 tumor cell line. Activity‐directed fractionation of the extract by column chromatography on silica gel and high‐pressure liquid chromatography led to the isolation of the acetogenins 1 – 4 as the main active principles. The structures of the two novel structures named sootepensin A (1) and sootepensin B (2) were elucidated by spectroscopic analysis (UV, EI‐ and ESI‐MS, 1D‐ and 2D‐1H‐ and 13C‐NMR). The absolute configurations were established by 2D‐NMR experiments utilizing Mosher esters. Two recently described compounds, tonkinin C (3) and tonkinesin C (4), were also isolated and are new to the genus Dasymaschalon. All four acetogenins were found to be highly cytotoxic against the L1210 tumor cell line.

Dasymaschalolactams A–E, Aristolactams from a Twig Extract of Dasymaschalon dasymaschalum

“…In Thailand, only 12 species are recognized . Previous phytochemical investigations on this genus have resulted in the isolation of various classes of compounds including flavonoids, triterpenoids, alkaloids, , neolignans, benzyl benzoate derivatives, , phenylpropanoids, acetogenins, and oxygenated cyclohexene derivatives. , Some of these compounds have shown interesting biological properties including cytotoxicity, − , antimalarial, anti-inflammatory, and anti-HIV effects. , Dasymaschalon dasymaschalum (Blume) I.M. Turner has many synonym names, including D. blumei Finet & Gagnep., D. coelophloeum (Scheff.)…”

“…). max 3224, 2998, 1670, 1448, 1350, 1287 cm −1 ; 1 H and13 C NMR, see Tables1 and 2; HRESITOFMS m/z 362.1001 [M + Na] + (calcd for C 19 H 17 NO 5 Na, 362.1004). Dasymaschalolactam B (2): light yellow, viscous oil; UV (MeOH) λ max (log ε) 399 (2.66), 276 (3.39), 258 (3.44), 229 (3.29), 204 (3.38) nm; IR (neat) ν max 3241, 2939, 1688, 1378, 1083 cm −1 ; 1 H and13 C NMR, see Tables1 and 2; HRESITOFMS m/z 340.1186 [M + H] + (calcd for C 19 H 18 NO 5 , 340.1185).…”

“…max 3224, 2998, 1670, 1448, 1350, 1287 cm −1 ; 1 H and13 C NMR, see Tables1 and 2; HRESITOFMS m/z 362.1001 [M + Na] + (calcd for C 19 H 17 NO 5 Na, 362.1004). Dasymaschalolactam B (2): light yellow, viscous oil; UV (MeOH) λ max (log ε) 399 (2.66), 276 (3.39), 258 (3.44), 229 (3.29), 204 (3.38) nm; IR (neat) ν max 3241, 2939, 1688, 1378, 1083 cm −1 ; 1 H and13 C NMR, see Tables1 and 2; HRESITOFMS m/z 340.1186 [M + H] + (calcd for C 19 H 18 NO 5 , 340.1185). C (3): yellow, viscous oil; UV (MeOH) λ max (log ε) 400 (2.69), 257 (3.52), 233 (3.37) nm; IR (neat) ν max 3203, 2925, 2858, 1694, 1468, 1382 cm −1 ; 1 H and 13 C NMR, see Tables 1 and 2; HRESITOFMS m/z 348.0849 [M + Na] + (calcd for C 18 H 15 NO 5 Na, 348.0848).…”

“…C (3): yellow, viscous oil; UV (MeOH) λ max (log ε) 400 (2.69), 257 (3.52), 233 (3.37) nm; IR (neat) ν max 3203, 2925, 2858, 1694, 1468, 1382 cm −1 ; 1 H and 13 C NMR, see Tables 1 and 2; HRESITOFMS m/z 348.0849 [M + Na] + (calcd for C 18 H 15 NO 5 Na, 348.0848). Dasymaschalolactam D (4): brown, viscous oil; UV (MeOH) λ max (log ε) 396 (2.64), 276 (3.41), 258 (3.47), 233 (3.42), 204 (3.32) nm; IR (neat) ν max 3241, 2935, 1682, 1383, 1260, 1076 cm −1 ; 1 H and13 C NMR, see Tables1 and 2; HRESITOFMS m/z 326.1031 [M + H] + (calcd for C 18 H 16 NO 5 , 326.1028). Dasymaschalolactam E (5): yellow, viscous oil; UV (MeOH) λ max (log ε) 335 (3.18), 284 (3.87), 234 (3.72), 215 (3.75) nm; IR (neat) ν max 3224, 2942, 1678, 1605, 1376, 1109, 1035 cm −1 ; 1 H and13 C NMR, see Tables1 and 2; HRESITOFMS m/z 296.0927 [M + H] + (calcd for C 17 H 14 NO 4 , 296.0923).…”

“…Dasymaschalolactam D (4): brown, viscous oil; UV (MeOH) λ max (log ε) 396 (2.64), 276 (3.41), 258 (3.47), 233 (3.42), 204 (3.32) nm; IR (neat) ν max 3241, 2935, 1682, 1383, 1260, 1076 cm −1 ; 1 H and13 C NMR, see Tables1 and 2; HRESITOFMS m/z 326.1031 [M + H] + (calcd for C 18 H 16 NO 5 , 326.1028). Dasymaschalolactam E (5): yellow, viscous oil; UV (MeOH) λ max (log ε) 335 (3.18), 284 (3.87), 234 (3.72), 215 (3.75) nm; IR (neat) ν max 3224, 2942, 1678, 1605, 1376, 1109, 1035 cm −1 ; 1 H and13 C NMR, see Tables1 and 2; HRESITOFMS m/z 296.0927 [M + H] + (calcd for C 17 H 14 NO 4 , 296.0923). Dasymaschalolactone (17): colorless, viscous oil; UV (MeOH) λ max (log ε) 295 (3.17), 237 (3.64), 208 (4.35) nm; IR (neat) ν max 2950, 2901, 1750, 1604, 1180 cm −1…”