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Non‐Phenolic Dicinnamamides from Pholiota Spumosa : Isolation, Synthesis and Antitumour Activity
Author(s) -
Clericuzio Marco,
Tabasso Silvia,
Garbarino Juan A.,
Piovano Marisa,
Cardile Venera,
Russo Alessandra,
Vidari Giovanni
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700558
Subject(s) - chemistry , putrescine , spermidine , polyamine , cinnamic acid , stereochemistry , biochemistry , enzyme
Two new amides derived from cinnamic acid, namely,( R )‐2‐hydroxyputrescine dicinnamamide ( 4 ) and pholiotic acid {(2 R )‐2‐[( S )‐3‐hydroxy‐3‐methylglutaryloxy]putrescine dicinnamamide} ( 5 ), in addition to the known compound maytenine ( N 1 , N 8 ‐dicinnamoyl spermidine) ( 3 ) were isolated from the fruiting bodies of the Basidiomycete Pholiota spumosa . The absolute configuration of 4 was established as ( R ) by its total synthesis starting from ( S )‐dimethylmalate, whereas that of 5 was determined by conversion into the known compound methyl ( S )‐4‐[( S )‐1‐(1‐naphthalen‐1‐yl)ethylcarbamoyl]‐3‐hydroxy‐3‐methylbutanoate ( 14 ). Compounds 3 and 5 exhibited an inhibitory effect on cell growth of the androgen‐insensitive DU‐145 prostate cancer cells, which suggests that these fungal polyamine conjugates, like other polyamine analogues, might have chemotherapeutic potential against androgen‐independent prostatic cancer. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)