Alstonia macrophylla

Alstonia macrophylla Wall. Villalstonine, macralstonine, macral-... 

Apocynaceae Alstonia macrophylla Talcarpine Pleiocarp amine Alstoumerine 2-O-epiantirhine Alstonerine Alstophyline Macralstonine Alstomacrophyline Villalstonine Alstomacroline Macrocarpamine... 

Keawpradub, N., Eno-Amooquaye, E., Burke, P. J. and Houghton, P. J. 1999. Cytotoxic activity of indole alkaloids from Alstonia macrophylla. Planta Medica, 65 311-315. 

Alstonia macrophylla Wall, ex G. Don / stem EtOH/ Maceration Sweroside, naresuanoside [128]... 

Preparative chromatography was performed with thin layer chromatography (TLC) aluminum sheets and 8 2 chloroform/ methanol as mobile phase of a fraction from the 95% EtOH extract of stems of Alstonia macrophylla. This procedure led to the isolation of the compounds sweroside (2 mg) and naresuanoside (3 mg) [128]... 

The bisindole alkaloids alstomacrophylline 108 and alstomacroline 109 have been isolated from the root bark of Alstonia macrophylla along with the monomeric indole alkaloid 20- f-antirhine <1997P757>. A dimeric indole alkaloid, schischkiniin 110, was isolated from the seeds of Centaurea schischkinii <2005T9001>. 

Two new oxindoles, ATb-demethytalstophyllal oxindole (99) and alstonal (100), together with three known oxindoles Nb-demethylalstophylline oxindole (101), alstonisine (102), and talcarpine were isolated from Alstonia macrophylla occurring in Sabah, Malaysian Borneo [87]. Compound 99 is an isomer of the known 101. The NMR spectral data were similar to those of 101 except for the appearance of an aldehyde function and a vinylic methyl group in place of an... 

The stem-bark extract of the Malayan Alstonia macrophylla provided in addition to seven known alkaloids, three new indole alkaloids, lO-methoxyaflinisine (334), 10-methoxy-cathafoline (335) and alstonerinal (336) [226]. The latter is a type A macroline and coeluted with the known type B macroline, alstonerine (337) during chromatography, and proved resistant to further resolution by chromatography or fractional crystallization. Eventually a pure sample was obtained by reduction of a mixture of 336 and 337 to yield the isomeric alcohols 338 and 339, followed by oxidation of338 to yield alstonerinal (336). 

Demethoxycarbonyl-19,20-dihydrovobasine has been isolated from Rauwol-fia discolor and 17-0-benzoylvincamajine from Alstonia macrophylla. ... 

The monomeric cleavage base alstophylline (221) occurs naturally in Alstonia macrophylla Wall. Macroline (215) was previously isolated from villalstonine (213). The cleavage ketone, C20H26O2N2, has been assigned structure (222) based on the following considerations it is an indole and contains... 

Hydroxy-17-decarbomethoxy-16-dihydro-epiajmalicine (87), Q9H24N2O2, mp 185°C, is a new natural product encountered in the bark of Hunteria zeylanica, a plant endemic to Sri Lanka (78). Structural proof involved the semisynthesis of 87 by oxymercuration of corynantheal. Other indole alkaloids belonging to this class isolated from H. zeylanica included yohim-bol (88) and the new natural product epiyohimbol (89), C19H24N2O, mp 257°C, whose structures were confirmed by comparison with NaBfL reduction products of yohimbone. The fruits of Alstonia macrophylla have... 

Of the 12 alkaloids belonging to this group occurring in Sri Lankan flora, 11 were encountered in Alstonia macrophylla Wall, of the family Apocynaceae, and the remaining alkaloid was isolated from Taberrtaemon-tana divaricata (L.) Br. ex Roem et Schult. of the same family. Six of the alkaloids were found to be new. Vincamajine (101) and its new derivative, 19-hydroxyvincamajine (102), are two alkaloids of the ajmaline subgroup present in A. macrophylla (82). The structure of 102 was elucidated with the aid of IR, H NMR, and low-resolution MS data. A. macrophylla also... 

The sarpagine subgroup of indole alkaloids in Sri Lankan plants is represented by two new alkaloids alstoumerine (107) from Alstonia macrophylla (86) and 11 -methoxy-N-methyldihydropericydivine (108) from Tabemae-montana divaricata (87). Alstoumerine, C20H24N2O4, mp 170°C, [a]D -5.5°,... 

The Sri Lankan Alstonia macrophylla also contained a series of alkaloids belonging to the 4,21-seco-lO-deoxysarpagine or indolohomotropane subgroup. Talcarpine (109) (82,88), alstophylline (110), (82,88), and alstonerine [demethoxyalstophylline (111)] (79,82,88) are three known alkaloids isolated from A. macrophylla. Alstomacrocine (112), C21H28N2O2, on the other... 

The unusual oxindole alkaloid macroxine-A (159), C20H26N2O3, [a]D +72.2°, from Alstonia macrophylla was reported by Atta-ur-Rahman and co-workers (98). Although UV and IR spectra of macroxine-A showed some characteristics of an oxindole alkaloid, the MS had an important fragment ion at m/z 152 (40%) not usually found in the MS of oxindole... 

Two bis-indohomotropane alkaloids, macralstonine (188) and anhy-dromacralstonine (189), were isolated from the stem bark and leaves of Alstonia macrophylla (82). Root bark of the same plant was recently reported to contain macralstonine (188) (88). 

Broussonetia zeylanica Broussonetia zeylanica Alstonia macrophylla Tabemaemontana dichotoma Alstonia macrophylla Tabemaemontana dichotoma Tabemaemontana dichotoma Limonia acidissima Neolitsea fuscata Neisosperma oppositifolia Holarrhena mitis Hunteria zeylanica Hunteria zeylanica Tabemaemontana dichotoma Mitragyna parvifolia Uncaria elliptica Neisosperma oppositifolia Tabemaemontana divaricata Tabemaemontana divaricata Tabemaemontana dichotoma Tabemaemontana dichotoma Murraya koenigii Murraya koenigii... 

The structure of villalstonine (XIV), the principal alkaloid of Alstonia macrophylla, has recently been elucidated (28-32), mainly owing to the brilliant investigations of Hesse, Schmid, Taylor, and their collaborators (29, 30) their conclusions have been triumphantly confirmed by an independent X-ray crystal structure determination (31). Alkaloid B, one of the constituent bases of A. muelleriana Domin. (33), has been shown to be identical with villalstonine (31), the early work on which (see Volume... 

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