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Isolation and elucidation of the structure of homocryptolepinone
Author(s) -
Sharaf Maged H. M.,
Schiff Paul L.,
Tackie Albert N.,
Phoebe Charles H.,
Davis Ann O.,
Webster Andrews C.,
Crouch Ronald C.,
Martin Gary E.
Publication year - 1995
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.5570320537
Subject(s) - chemistry , alkaloid , stereochemistry , biogenesis , two dimensional nuclear magnetic resonance spectroscopy , biochemistry , gene
The structure of a new indolobenzazepine alkaloid, homocryptolepinone, isolated from extracts of the roots of the indigenous Ghanaian medicinal plant Cryptolepis sanguinolenta , is reported. The structure was determined using mass spectrometric, one‐dimensional nOe difference nmr, and inverse‐detected two‐dimensional nmr experiments which included HMQC, IDR‐(Inverted Direct Response)‐HMQC‐TOCSY, and HMBC experiments. The structure of homocryptolepinone is significant in that it may provide insight into the biogenesis of the benzpyrrolizinobenzazepine portion of the structure of the complex spiro nona‐cyclic alkaloid cryptospirolepine previously isolated in these laboratories from C. sanguinolenta , and which has no precedent in alkaloid chemistry.