Alkaloids of Caryomene olivascens (Menispermaceae). Bisbenzylisoquinoline with new structure.
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Abstract:
Nine isoquinoline alkaloids belonging to the protoberberine, proaporphine and bisbenzyl-isoquinoline series were isolated from Caryomene olivascens (Menispermaceae). Four compounds are new : (-)-2-norlimacine (4), (-)-caryolivine (6), (+)-1, 2-dehydro-2-norlimacusine (9) and N-formylstepharine (3). The last one is the first N-formyl derivative to be reported in the proaporphine group. Its biogenetic origin is discussed. Structures were established on the basis of 360 MHz (FT) nuclear magnetic resonance measurements and also by chemical correlation in the case of 3.Keywords:
Menispermaceae
Isoquinoline
Derivative (finance)
From the leaves of Stephania cepharantha HAYATA (Menispermaceae) cultivated in Japan, a new morphinane alkaloid, cephasugine (1), was isolated together with 14 known alkaloids. The structure of 1 was elucidated as the N-methyl derivative of sinococuline (17) by comparison of spectroscopic data with those of cephakicine (16). This is the first report of the alkaloidal constituents of the leaves of S. cepharantha.
Menispermaceae
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Isoquinoline
Aporphine
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Isoquinoline
Tetrahydroisoquinoline
Hydroxymethyl
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Isoquinoline
Menispermaceae
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Abstract The synthesis of the novel enamide isoquinoline alkaloid polycarpine, ( Z )‐1‐(2′‐hydroxy‐3′,4′‐dimethoxy‐benzylidene)‐3,4‐dihydro‐6,7‐dimethoxy‐2‐(1H)isoquinolinecarboxaldehyde, proceeding from commercially available 2′,3′,4′‐trimethoxyacetophenone in seven steps is described. The O ‐methyl and O ‐benzyl derivatives were also obtained.
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Analysis of the alkaloidal fraction of the stem bark extract of Pachygone dasycarpa (Menispermaceae) resulted in the isolation of 10 known bisbenzylisoquinolines, (+)-tetrandrine, (+)-penduline, (+)-fangchinoline, (+)-atherospermoline, (+)-N-methyl-7-O-demethylpeinamine, (+)-daphnoline, (4-)-isotrilobine (1), (+)-cocsuline (2), (+)-tricordatine (3), (+)-2'-norcocsuline, and the new alkaloid (+)-12-O-methyltricordatine (4). The last bisbenzylisoquinoline alkaloid isolated, (+)-angchibangkine (5), is the first member of this alkaloid class found to possess three diphenyl ether bridges in the 7-6',8-7', and 11-12' positions. Structure elucidation of these alkaloids and of (+)-O-methylangchibangkine (6) was achieved by analysis of spectral data. Compounds 4-6 show antiplasmodial activity against Plasmodium falciparum.
Menispermaceae
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Berberis
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Abstract Die Struktur der in der Titelpflanze enthaltenen gelben Verbindung (VIa) wird durch Synthese aus dem Amin (I) und dem Säurechlorid (IIa) über die Stufen (IIIa)‐(Va) bestätigt.
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A phytochemical investigation of the stems of Synclisia scabrida Miers (Menispermaceae) resulted in the isolation of a number of known bisbenzylisoquinoline alkaloids: cycleanine, norcycleanine, cocsuline and cocsoline. A new alkaloid, cycleanine N-oxide was also isolated.
Menispermaceae
Phytochemical
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