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The isolation and structure determination of cryptomisrine, a novel indolo[3,2‐ b ]quinoline dimeric alkaloid from cryptolepis sanguinolenta
Author(s) -
Sharaf Maged H. M.,
Schiff Paul L.,
Tackie Albert N.,
Phoebe Charles H.,
Johnson Robert L.,
Minick Doug,
Crouch Ronald C.,
Martin Gary E.,
Andrews C. Webster
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330343
Subject(s) - chemistry , quinoline , homonuclear molecule , heteronuclear molecule , alkaloid , stereochemistry , dept , two dimensional nuclear magnetic resonance spectroscopy , carbon 13 nmr , monomer , proton nmr , molecule , nuclear magnetic resonance spectroscopy , organic chemistry , polymer
The isolation and structure determination of cryptomisrine, a novel indolo[3,2‐ b ]quinoline dimeric alkaloid obtained from extracts of the roots of the Ghanaian medicinal plant Cryptolepis sanguinolenta is reported. The structure determination was made via a consideration of the spectral data, including uv, ir, nmr, and mass spectra. In particular, one‐dimensional proton/carbon nmr, one‐dimensional nOe difference nmr, and a series of homonuclear (COSY) and inverse‐detected heteronuclear two‐dimensional (HMQC, HMBC) experiments were utilized, as well as high resolution FABMS. Cryptomisrine is most unusual in that its two monomeric parts apparently exist in such a C 2 symmetric environment that only one set of proton and carbon nmr resonances are observed. Cryptomisrine is the first example of a dimeric indolo‐[3,2‐ b ]quinoline alkaloid to have been isolated from nature.