Chemical constituents of Piptadenia gonoacantha (Mart.) J.F. Macbr (pau jacaré)

Abstract

The phytochemical investigation of Piptadenia gonoacantha (Mart.) J.F. Macbr. (Leguminosae-Mimosoideae), commonly known as "pau jacaré" (alligator stick), afforded sitosterol, campesterol, stigmasterol, the N-benzoylphenylalanine-2-benzoylamide-3-phenylpropyl ester, known as asperphenamate, sitosterol-3-O-β-D-glucopyranoside, besides three flavonoids, apigenin, 5-O-methylapigenin and 7,4'-dihydroxy-3',5-dimethoxyflavone from its branches. From its leaves, the methyl gallate and two flavonoids, vitexin and isovitexin, were isolated. From its bark, a mixture of sitosterol, campesterol, and stigmasterol, besides a mixture of cycloartenone, cycloartan-25-en-3-one, and 24-methylene-cycloartenone, and the pure triterpenes 24-methylenecycloartanol, friedelin, lupeol and lupenone, were isolated. Their structures were established on the basis of spectral analysis, comparison with literature data and GC-MS analysis of the mixtures. The ester, flavonoids and the cycloartanes are been identified for first time in the genus Piptadenia.

Two newPenicilliumspeciesPenicillium buchwaldiiandPenicillium spathulatum, producing the anticancer compound asperphenamate

“…These species all belong to the Trichocomaceae . However, asperphenamate has also been found in a series of unrelated plant species: Anaphalis subumbellata (Compositae), Artemisia anomala (Asteraceae), Begonia nantoensis (Begoniaceae), Cantharanthus pusillus (Apocunaceae), Croton hieronymi (Euphorbiaceae), Desmos longiflorus (Annonaceae), Dorstenia dinklagei (Moraceae), Ficus mucoso (Moraceae), Grangea maderaspatana (Compositae), Leucas aspera (Lamiaceae), Medicago polymorpha (Fabaceae), Melastroma malabathricum (Lamiaceae), Miliusa velutina (Annonaceae), Piper aurantiacum (Piperaceae), Piptadenia gonoacantha (Leguminosae), Saurauia napaulensis (Actinidiaceae), Uvaria ufa (Annonaceae), Wikstroemia indica (Thymelaceae) and Zeyhera digitalis (Bignoniaceae) (Battersby & Kapil, 1965;Banerji & Ray, 1981;Wu et al, 2004;Talapatra et al, 1983;Poi & Anityachoudhury, 1986;Jakupovic et al, 1987;Singh & Jain, 1990;Catal an et al, 2003;Bankeu et al, 2010;Geng et al, 2006;Pomini et al, 2006;Sandhu et al, 2006;Vouffo et al, 2008;Xiao et al, 2007;Carvalho et al, 2010;Macabeo et al, 2010;Sirat et al, 2010) leading to the suggestion that asperphenamate may be produced by endophytic fungi rather than plants (Macabeo et al, 2010). Asperphenamate has recently attracted much interest because of its antitumor (Wu et al, 2004;Yuan et al, 2010Yuan et al, , 2012Li et al, 2012) and antimicrobial activity.…”

Antinociceptive and Anti-Inflammatory Effects of Hydroalcoholic Extract of Leaves of Piptadenia Gonoacantha (Mart.) Macbr. In Experimental Animal Models

“…In EPG was identified presence of flavonoids like apigenins, vitexin, and isovitexin (Carvalho et al, 2010), which have previously demonstrated to possess antinociceptive and anti-inflammatory activities (Mills and Bone, 2000;Jeong et al, 2009;Alves et al, 2012). Some flavonoids may interfere with inflammatory response by inhibiting COX-2 (Havsteen, 2002).…”

“…The plant is commonly used in folk medicine to treat inflammatory disorders, and popularly known as "pau jacaré" (alligator stick). Phytochemical studies have be performed on the composition of P. gonoacantha, and a number of compounds have been identified such as triterpenes (friedelin, lupenone, lupeol, cycloartenone, cycloartan-25-26-en-3-one, 24-methylene-cycloartanone, and 24-methylenecycloartanol), steroids (sitosterol, campesterol, and stigmasterol), saponin (sitosterol-3-O -β-D-glucopyranoside), flavonoids (apigenin, 5-methylapigenin, 7,4'-dihydroxy-3',5-dimethoxyflavone, vitexin, and isovitexin), asperphenamate and methyl gallate (Carvalho et al, 2010). However, no research has been investigated on the analgesic and anti-inflammatory activity of P. gonoacantha yet.…”

Chemical Constituents and Lethality ofPseudopiptadenia Contorta(DC.) G. P. Lewis & M. P. Lima (Fabaceae) againstArtemia salinaLeach

“…As espécies também são bastante utilizadas na recuperação ambiental, devido ao crescimento rápido em solos pobres e degradados. 5 A química do gênero esta caracterizada pela presença de alcalóides, 6,7 flavonóides, [8][9][10] triterpenóides 11 e taninos. 12 Algumas espécies do gênero são utilizadas na medicina tradicional no tratamento de diarreia, infecções do trato urinário, dores de cabeça e garganta, gastrite, tuberculose, pneumonia, gonorreia e varíola.…”