Caldensinic acid, a prenylated benzoic acid from Piper caldense

The extracts from leaves of Piper caldense afforded the new prenylated benzoic acid, caldensinic acid (3-[(2′ E,6′ E,10′ E)-11′-carboxy-3′,7′,15′-trimethylhexadeca-2′,6′,10′,14′-tetraenyl]-4,5-dihydroxybenzoic acid). The natural compound and derivatives displayed antifungal activity against the phyt...

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Bibliographic Details
Published in:Phytochemistry letters 2009-08, Vol.2 (3), p.119-122
Main Authors: Freitas, Giovana C., Kitamura, Rodrigo O. Saga, Lago, João Henrique G., Young, Maria Claudia M., Guimarães, Elsie F., Kato, Massuo J.
Format: Article
Language:English
Subjects:
Antifungal activity
Caldensinic acid
Cladosporium cladosporioides
Piper
Piper caldense
Piperaceae
Prenylated benzoic acid
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Summary:The extracts from leaves of Piper caldense afforded the new prenylated benzoic acid, caldensinic acid (3-[(2′ E,6′ E,10′ E)-11′-carboxy-3′,7′,15′-trimethylhexadeca-2′,6′,10′,14′-tetraenyl]-4,5-dihydroxybenzoic acid). The natural compound and derivatives displayed antifungal activity against the phytopathogenic fungi Cladosporium cladosporioides and C. sphaerospermum by direct bioautography. The CH 2Cl 2 and MeOH extracts from leaves of Piper caldense were subjected to chromatographic separation procedures to afford the new prenylated benzoic acid, caldensinic acid (3-[(2′ E,6′ E,10′ E)-11′-carboxy-3′,7′,15′-trimethylhexadeca-2′,6′,10′,14′-tetraenyl]-4,5-dihydroxybenzoic acid) whose structure was determined by spectral analysis, mainly NMR ( 1H, 13C, HSQC, HMBC) and ESI-MS. The natural compound and derivatives displayed antifungal activity against the phytopathogenic fungi Cladosporium cladosporioides and C. sphaerospermum by direct bioautography.
ISSN:1874-3900
1876-7486
DOI:10.1016/j.phytol.2009.03.006