N-Methyl-2,3,6-Trimethoxymorphinandien-7-one N-oxide: A Minor Alkaloid from Alseodaphne perakensts

Abstract

Unimity of Calymia, Berkeky, Ca/.$mia 94720hSTRACr.--The novel alkaloid N-methyl-2,3,6-trimethoxymorphi~dien-7-one Noxide [2] has been isolated as a minor constituent from Als&phnept7uknrrisS. Alsdpbne perakensis (Gamb.) Kosterm. (Iauraceae) is a tree of moderate size that is widely distributed throughout peninsular Malaysia. Although there has been no reported use of this plant in traditional folk medicine practices (l), in field tests the leaves were found to be rich in alkaloids (2).' Initial chemical work on this species (3) led to the isolation of the major alkaloidal component, N-methyl-2,3 ,6-trimethoxymorphinandien-7-one El), a compound noted previously in Cocculus laurafolius DC. (Menispermaceae) (4), Rhzgzucarya w emifeu Miers (Menispermaceae) ( 5 ) , and Litsea sebifera B1. (Lauraceae) (6).In further work, we have now isolated a new polar, minor alkaloid, N-methyl-2,3,6-trimethoxymorphinandien-7-one N-oxide 121 present in the extract of the 1 'At the time of collection and preparation of this "Proceedings" the plant was tentatively assigned, incorrectly, as Deba&a mirrocmpa. 0 2 leaves of A . perakmis. All attempts to crystalize the alkaloid, which is rather hygroscopic, proved hitless, and after purification by multiple preparative tlc the compound was obtained as an amorphous, pale yellow solid.The spectroscopic data were particularly useful in assigning structure. The uv spectrum is similar to that of 1 (7), suggesting close similarities in the respective chromophores, and the ir spectrum substantiated the presence of the conjugated carbonyl and aromatic functionalities. The general appearance of the 'H-nmr spectrum of 2 was also similar to that of 1, with the exception of small chemical shift differences in comparable resonances. Three methoxy substituents and the N-methyl group were clearly present (6 3.89, 3.85, 3.80, and 3.41, respectively), and four one-proton singlet signals were consistent with the two para oriented aromatic protons and the two cyclohexadienonyl protons. Other discrete structural elements recognizable, which were ac-

Activity-Guided Isolation of Antioxidative Constituents ofCotinuscoggygria

“…20,21 Methyl gallate (5): off-white powder; EIMS m/z 184; IR, 1 H NMR, and 13 C NMR data were consistent with literature values. 22,23,28 Pentagalloyl glucose (6): off-white crystals; ESIMS (positive-ion mode) m/z 941; 1 H NMR and 13 C NMR data were consistent with literature values. 24 Methylation of Compound 1.…”

“…Methyl gallate (5): off-white powder; EIMS m / z 184; IR, 1 H NMR, and 13 C NMR data were consistent with literature values. ,, …”

“…Compounds 4 − 6 were isolated using repeated Si gel column chromatography from an initial collection of C. coggygria made in 1972 and were identified as gallic acid, , methyl gallate, , and pentagalloyl glucose, respectively.…”

New Alkaloids from Annona purpurea

“…18 The identities of the known compounds were verified by comparing UV, IR, 1 H NMR, 13 C NMR, and MS data with published values. 4,[7][8][9][10][11][12][13][14][15][16][17][18][19]…”

“…Among these, 7-dehydroaporphine alkaloids exhibited significant antiplatelet aggregation activity. ,, In this paper, we report herein three new alkaloids, promucosine ( 1 ), romucosine F ( 2 ), and romucosine G ( 3 ), along with 28 known compounds. From the methanolic extract of the stems of A. purpurea , the following known compounds were isolated: seven aporphines, (+)-norpurpureine, (−)-norglaucine, (+)-northalbaicalidine, (+)-thalicsimidine [(+)-purpureine], (−)-lirinidine, (+)-apoglaziovine, and (+)-isocorydine; four oxoaporphines, lysicamine, liriodenine, oxopurpureine, and oxoglaucine; one proaporphine, (+)-stepharine; three morphinandienones, (−)-pallidine, (−)-norpallidine, and (+)- O -methylflavinantine; , one benzylisoquinoline, (+)-reticuline; one isoquinolone, thalifoline; one lactam, squamolone; one acetogenin, purpurenin; five benzenoids, methylparaben, isovanillic acid, vanillin, isovanillin, and p -methoxybenzoic acid; and four steroids, β -sitosterol, stigmasterol, β -sitosteryl- β - d -glucoside, and stigmasteryl- β - d -glucoside . The identities of the known compounds were verified by comparing UV, IR, 1 H NMR, 13 C NMR, and MS data with published values. ,− …”