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Prelandrine, the Key‐Step Intermediate in the Biosynthesis of the Macrocyclic Spermine Alkaloid Aphelandrine
Author(s) -
Nezbedová Lenka,
Hesse Manfred,
Drandarov Konstantin,
Werner Christa
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010131)84:1<172::aid-hlca172>3.0.co;2-b
Subject(s) - chemistry , atmospheric pressure chemical ionization , alkaloid , high performance liquid chromatography , spermine , mass spectrometry , biosynthesis , chromatography , stereochemistry , chemical ionization , organic chemistry , ionization , enzyme , ion
By means of the high sensitive on‐line‐coupled high‐performance liquid chromatography and atmospheric‐pressure chemical‐ionization mass spectrometry (HPLC/APCI‐MS and HPLC/APCI‐MS/MS) techniques, the new macrocyclic spermine alkaloid prelandrine ( 5 ) was detected in the roots of Aphelandra squarrosa (Acanthaceae), and its structure was elucidated as 4′‐hydroxyprotoverbine (=8‐(4‐hydroxyphenyl)‐1,5,9,13‐tetraazacycloheptadecan‐6‐one). It was further demonstrated that protoverbine ( 6 ) is enzymatically hydroxylated to prelandrine ( 5 ) in a reaction catalyzed by microsomes from the roots of A. squarrosa . The chemical synthesis of (−)‐( S )‐prelandrine is also described. The possible key role of prelandrine ( 5 ) as an intermediate in the biosynthesis of aphelandrine ( 1 ) is discussed.