A Caryachnine N-Methosalt From Cryptocarya chinensis and PMR Spectral Characteristics of Some Quaternary Pavine Alkaloids

Chen, Chung-hsiung; Lee, Shoei-shen; Lai, Chung-fang; Wu, J.; Beal, Jack L.

doi:10.1021/np50002a005

Cited by 12 publications

(12 citation statements)

References 9 publications

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“…Besides the structural elucidation of neocaryachine, we also examined the spectral properties of caryachine N-metho perchlorate [5], a quaternary base previously isolated from C. chinensis (4). Its :H chemical shifts (Table 1) were assigned by nOe studies and double resonance experiments.…”

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Neocaryachine, a New Pavine Alkaloid from Cryptocarya chinensis, and NMR Spectral Properties of Related Alkaloids

Lee¹,

Liu²,

Chen³

1990

J. Nat. Prod.

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Cryptocarya chinensis. Its structure was established by spectral analysis including nOe and 2D nmr techniques. 13C-nmr assignments of the related pavine alkaloids (-)-caryachine [2], (-)eschscholtzine [3], (+)-eschscholtzidine [4], and their corresponding N-metho iodides 6 and 7 were also made by using 1 and (-)-caryachine N-metho perchlorate [5] as model compounds.Cryptocarya chinensis Hemsl. (Lauraceae) is a perennial plant widely distributed in forests on lowlands of altitude 500-1000 m in Taiwan and in southeastern China (1). Past studies on the alkaloidal constituents of this species have revealed that it is a good source for pavine alkaloids (2-4). So far, three tertiary pavine alkaloids, namely (-)caryachine [2}, (-)-eschscholtzine [3], and (+ )-eschscholtzidine [4], and a quaternary pavine, (-)-caryachine N-metho perchlorate [5], have been isolated from this species.Here we report the isolation and characterization of an additional new pavine alkaloid, neocaryachine [1], from the stem bark of this plant.

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Neocaryachine, a New Pavine Alkaloid from Cryptocarya chinensis, and NMR Spectral Properties of Related Alkaloids

Lee¹,

Liu²,

Chen³

1990

J. Nat. Prod.

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“…-147°(c= 1.64, CHC13) (35) [a}25D: -150°(c=0.34, CHC13) (36) [<x]27D: -151°(c=0.5, CHC13) (8) [al21D: -153°±3°(c=0.30, CHC1}) (37) £a]27D: -153.69°(c=2.786, CHC13) (14) [a]D: -154°( = 2.79, CHC13) (10) £a]20D: -154°±4°C HC13) (3) UV: (EtOH) 205 sh (4.94), 230 sh (4.12), 278 sh (37), 190(100), 177 (7), 176(6), 175 (15), 162(7), 137 (6) -194.2°(c= 1.56, MeOH) (10,46) UV: (EtOH) 235 sh (4.01), 282 sh(3.88), 290(3.97), 303 (3.72) (10) 'H-NMR: (CDClj) 2.50 (s, 3H,NCH3), 3.76(s, 3H, OCH3), 3.83 (s, 3H, OCH3), 3.91 (s, 1H, CH), 4.01 (s, 1H, CH), 5.79 and 5.81 (ABq,J=l Hz, 2H, OCH20), 6.41 (s, 2H, ArH), 6.58 C20H21O4N: 339.1470…”

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“…(48) [a]28D: 0°( c=0.27, EtOH) (48) UV: (EtOH) 291.5 (3.97) (48) 'H-NMR: (CDC13) 2.54 (s, 3H, NCH3), 3.86(s, 3H, OCH3), 5.83 and 5.88 (q, 7=1.8 13. (-)-CARYACHINE N-METHO SALT C20H22O4N+: 340.1549 MP: (C104~) 211-212°( H20) (15) ( ) 174-175°(MeOH) (15)…”

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The Pavine and Isopavine Alkaloids

Gözler¹,

Lantz²,

Shamma³

1983

J. Nat. Prod.

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“…This alkaloid was found so far only in Cryptocarya chinensis HEMSL. (Lauraceae) 21. In all three species a negligible amount of escholamine (Vlb) was detected, which is the main alkaloid of the species E. c/.…”

Section: Collection Czechoslovak Chem Commun [Vol 511 [19861mentioning

confidence: 96%

On alkaloids from the aerial parts of three Eschscholtzia species

Slavík

Slavíková

1986

Collect. Czech. Chem. Commun.

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In the aerial parts of Eschscholtzia californica CHAM., E. dougla.lii (HOOK. et ARN.) WALP. and E. g/auca GREENE the main alkaloidal component is the quaternary base californidine. Eschscholtzine, allocryptopine, and protopine belong among the dominant tertiary alkaloids, which are accompanied by a small amount of N-methyllaurotetanine and the quaternary benzophenanthridines (sanguinarine, chelerythrine, chelirubine, chelilutine, and macarpine). The pavinane alkaloids isonorargemonine, caryachine, norargemonine, and bisnorargemonine and the aporphine alkaloids corydine and isocorydine were isolated from the aerial part of the E. douglasii species for the first time. These alkaloids were also detected in E. californica and E. glauca. Corytuberine was also isolated from all three species. From the fraction of quaternary alkaloids after conversion to iodides, in addition to californidine, escholamidine iodide was isolated from E. californica and E. douglasii species. From E. douglasii N-methyIcaryachininium iodide and from E. glauca magnoflorine iodide were also isolated. The presence of a small amount of the mentioned quaternary alkaloids, as well as traces of escholamine were also detectable in all three species.

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A Caryachnine N-Methosalt From Cryptocarya chinensis and PMR Spectral Characteristics of Some Quaternary Pavine Alkaloids

Cited by 12 publications

References 9 publications

Neocaryachine, a New Pavine Alkaloid from Cryptocarya chinensis, and NMR Spectral Properties of Related Alkaloids

Neocaryachine, a New Pavine Alkaloid from Cryptocarya chinensis, and NMR Spectral Properties of Related Alkaloids

The Pavine and Isopavine Alkaloids

On alkaloids from the aerial parts of three Eschscholtzia species

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