Prenylated Coumarins, Chalcone and New Cinnamic Acid and Dihydrocinnamic Acid Derivatives from Brosimum gaudichaudii

Abstract

Três novos derivados naturais dos ácidos cinâmico e diidrocinâmico foram isolados das raízes de Brosimum gaudichaudii, além de mais quatorze substâncias naturais conhecidas (dez cumarinas, uma chalcona, os dois esteróides b-sitosterol e 3b-O-b-D-glicopiranosil-b-sitosterol e o triterpeno bamirina). As estruturas destas substâncias foram estabelecidas com base na análise de dados espectrais, inclusive experiências de RMN 2D e espectros de massas. O ácido 4-hidroxi-3-prenilcinâmico pode ser postulado como precursor para todas substancias aromáticas. As novas substâncias naturais são derivadas do precursor das cumarinas que perdeu a possibilidade de formar o anel lactônico devido a O-metilação. Three new natural cinnamic acid and dihydrocinnamic acid derivatives were isolated from the roots of Brosimum gaudichaudii, in addition to fourteen known substances (ten coumarins, one chalcone, b-sitosterol, 3b-O-b-D-glucopyranosylsitosterol and b-amyrin). The structures were established by spectral data, including analysis of 2D-NMR experiments and mass spectra. All aromatic compounds have 4-hydroxy-3-prenylcinnamic acid as a common precursor. The new substances are derived from a precursor of the coumarins, which through an O-methylation lost its ability to form the lactone ring.

A substrate-specific cytochrome P450 monooxygenase, CYP6AB11, from the polyphagous navel orangeworm (Amyelois transitella)

“…species of legumes by A. transitella. This preadaption in turn may have enabled A. transitella to utilize a wide variety of nonindigenous tree fruit crops in Moraceae, Rosaceae, Rutaceae and other families containing prenylated compounds (Murray et al, 1982;Sang et al, 2002;Monteiro et al, 2002).…”

Ethnopharmacology of Fruit Plants: A Literature Review on the Toxicological, Phytochemical, Cultural Aspects, and a Mechanistic Approach to the Pharmacological Effects of Four Widely Used Species

“…Spectral analysis was carried out on an extract from B. gaudichaudii root bark, which led to the identification of a new coumarin called gaudichaudine ( 29 ), the coumarins psoralen ( 25 ), bergaptene ( 26 ), luvangetin ( 30 ) and (+)−(2’ S , 3’ R )-3’-hydroxyrmesin ( 31 ) and the pyranocoumarin xanthyletin ( 32 ). Subsequently, using the same type of extract and the same plant organ, the same researchers found the following secondary metabolites: coumarins marmesin ( 33 ), 1’,2’-dehydromarmesin ( 34 ), 8-methoxymarmesin ( 35 ) and 1’-hydroxy-3’- O -β-glucopyranosylmarmesin ( 36 ); the chalcone 2’,4’,4-trihydroxy-3’3-diprenylchalcone ( 37 ); and the triterpene β-amyrin ( 38 ) [ 93 , 94 ].…”

New Cytotoxic Alkylated Chalcones from Fatoua villosa

“…The known compounds were identified as 2 0 ,4dihydroxy-3,4 0 -dimethoxychalcone (4), [17] oxyphyllumchalcone C (5), [18] renifolin C (6), [19] isobavachalcone (7), [20] [21] kanzonol B (8), [22][23] (+)-fatouain A (9), [13] (-)-fatouain B (10), [13] glabralactone (11), [24] 1 0 ,2 0 -dehydromarmesin (12), [25] 8-hydroxyxanthyletin (13), [26] seseline (14), [27] dihydroxanthyletin (15), [28] 5,7-dihydroxy-6-prenyl coumarin (16), [29] 7-hydroxycoumarin (17), [30] and 7-hydroxy-5-methoxycoumarin (18), [31] resp., by comparing their spectroscopic data with those reported.…”