A Rare Glutamine Derivative from the Flower Buds of Daylily

A rare glutamine derivative, hemerocallisamine I (1), was isolated from the methanolic extract of the flower buds of daylily, together with a new pyrrole alkaloid hemerocallisamine II (2) and a new γ-lactam derivative, hemerocallisamine III (3). The chemical structures of the new compounds were eluc...

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Bibliographic Details
Published in:Organic letters 2014-06, Vol.16 (11), p.3076-3078
Main Authors: Matsumoto, Takahiro, Nakamura, Seikou, Ohta, Tomoe, Fujimoto, Katsuyoshi, Yoshikawa, Masayuki, Ogawa, Keiko, Matsuda, Hisashi
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Flowers
Glutamine - analogs & derivatives
Glutamine - chemistry
Glutamine - isolation & purification
Lactams - chemistry
Lactams - isolation & purification
Magnetic Resonance Spectroscopy
Molecular Structure
Pyrroles - chemistry
Pyrroles - isolation & purification
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Summary:A rare glutamine derivative, hemerocallisamine I (1), was isolated from the methanolic extract of the flower buds of daylily, together with a new pyrrole alkaloid hemerocallisamine II (2) and a new γ-lactam derivative, hemerocallisamine III (3). The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. For hemerocallisamine I (1), the absolute configuration was determined by Mo–Kα X-ray crystallographic analysis. This is the first report of a glutamine derivative with a pyrrole ring from natural plants.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol501182v