A New Tetrahydroprotoberberine Alkaloid from <i>Corydalis caseana</i> A. Gray

Yu, Chao-Mei; MacLean, David B.; Rodrigo, R.; Manske, Richard H. F.

doi:10.1139/v71-018

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(D_7= 16)1

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1971

1988

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Cited by 8 publications

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“…This included homo and hetero 2-D correlated experiments. Comparison of the spectra of an authentic sample of caseanidine (10), kindly provided by Dr. D.B. MacLean, confirmed the assignment.…”

supporting

confidence: 60%

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The Isolation and Characterization of a New Tetrahydroprotoberberine Alkaloid from Corydalis clarkei

Rothera¹,

Wehrli²,

Cook³

1985

J. Nat. Prod.

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The MeOH extract of Corydalis clarkei Prain yielded two tetrahydroprotoberberine alkaloids that bear the unusual 1,2- and 9, 10-tetraoxygenated substitution pattern observed previously only in caseanidine . The alkaloids have been identified as caseanidine (1) and the new alkaloid, clarkeanidine (2). The 1H- and 13C-nmr shifts of both alkaloids have been assigned unambiguously using 2-D nmr. The elucidation of the structure of 2 was achieved by comparison of the 1H- and 13C-nmr spectra of 2 with those of caseanidine coupled with additional spectroscopic evidence.

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supporting

confidence: 60%

“…This conclusion rests on the fact that the 13C-nmr signals for C-6 in 1 and 2 (49.2 and 49.1 ppm, respectively) are upfield of the expected tram shift value of approximately 51.4 ppm (15); moreover, the Bohlmann bands are weak. The stereochemistry of 2 at C-14 is based on that of caseanidine (1) (10). EXPERIMENTAL…”

Section: (D_7= 16)mentioning

confidence: 99%