Telisatin A, Telisatin B, and Telitoxinone, Three New Aporphinoids from Telitoxicum peruvianum

Abstract

The structures of telisatins A [1] and B [2] and telitoxinone {31, three new aporphinoid alkaloids isolated from a neutral fraction of Telitoxicum peruvianum, were determined by spectral data interpretation.

Phytochemical Investigation andIn VitroCytotoxic Evaluation of Alkaloids fromAbuta rufescens

“…This fraction also yielded a second tropoloisoquinoline alkaloid, isoimerubrine (7) [9], for the first time in this species. Repeated column chromatography of the phenolic alkaloid fraction afforded the known azafluoranthene norrufescine (8) [3] and telisatin A (9), an aporphine alkaloid [10]. However, another azafluoranthene, telitoxine (10) [11], and the oxoaporphine subsessiline (11) [12] were isolated here for the first time from A. rufescens.…”

Total Syntheses of Telisatin A, Telisatin B and Lettowianthine

“…234-235 °C (Lit. [ 1 ] m.p. 238-239 °C); UV (MeOH) λ max nm (log ε): 207 (4.03), 257 (4.26), 284sh (3.60), 322 (3.70), 336 (3.80), 352sh (3.56); IR (CH 2 Cl 2 -film) ν max cm -1 : 2925, 1748, 1701, 1605, 1584, 1531, 1462, 1423, 1386, 1306, 1261, 1195, 1149, 1131, 1112, 1037, 969, 924, 802, 759.…”

“…218-219 °C (Lit. [ 1 ] m.p. 221-222 °C); UV (MeOH) λ max nm (log ε): 203 (4.33), 223sh (4.26), 257 (4.59), 318sh (3.99), 329 (4.07); IR (CH 2 Cl 2 -film) ν max cm -1 : 2942, 2864, 1749, 1716, 1702, 1619, 1607, 1579, 1527, 1515, 1452, 1406, 1389, 1323, 1146, 1125, 1071, 1033, 973, 814, 757; 1 H-NMR: δ 9.37 (1H, br d, J = 8.5 Hz, H−11), 8.60 (1H, dd, J = 8.0, 1.3 Hz, H−8), 7.64-7.56 (1H, m, H−9), 7.55-7.45 (1H, m, H−10), 4.14 (3H, s, OCH 3 ), 4.03 (3H, s, OCH 3 ), 4.01 (3H, s, OCH 3 ), 3.91 (2H, t, J = 6.5 Hz, CH 2 ), 3.33 (2H, t, J = 6.5 Hz, CH 2 ); 13 C-NMR: δ 180.69(C), 159.86(C), 152.58(C), 152.16(C), 152.03(C), 150.16(C), 128.71(CH), 127.53(CH), 126.63(C), 126.38(C), 126.11(C), 125.78(CH), 123.66(CH), 121.18(C), 114.14(C), 104.17(C), 61.47(OCH 3 ), 61.30(OCH 3 ), 60.48 (OCH 3 ), 36.14(CH 2 ), 21.21(CH 2 ); HRMS (ESI-TOF) calcd for C 21 H 17 NO 5 ([M+H + ]) = 364.1179, Found 364.1231.…”

“…To date only five members of this type of aporphine alkaloids have been found to occur in Nature. These are telisatin A ( 1 ) and telisatin B ( 2 ) from Telitoxicum peruvianum Moldenke (Menispermaceae) [ 1 ], lettowianthine ( 3 ) and 11-methoxy-lettowianthine ( 4 ) from Lettowianthus stellatus Diels (Annonaceae) [ 2 ], and laurodionine ( 5 ) from Phoebe formosana Hayata (Lauraceae) [ 3 ]. Annonbraine, isolated from Annona glaba L (Annonaceae), was also assigned the same structure as lettowianthine ( 3 ), although there was a big difference in the melting points of the two alkaloids [ 4 ].…”

A Facile Synthesis of Telisatin A via Microwave-Promoted Annulation and ­Reformatsky Reaction

“…The plant has been used as an ingredient of curare by the Huitoto Indians in Peru. 2 Laurodionine (1c) was isolated from the stems of Phoebe formosana, Hayata (Lauraceae) which is abundantly available in Taiwan. 3 The last two compounds, lettowianthine (1d) and 11-methoxylettowianthine (1e), were isolated from the root bark of Lettowianthus stellatus, a plant growing in coastal rain forests of Kenya and Tanzania.…”