Anthraquinones from the bark of Senna macranthera

Abstract

ABSTRACT2-acetyl physcion (2-acetyl-1,8-dihydroxy-6-methoxy-3-methyl-9,10-anthraquinone, 2), a rare anthraquinone, was isolated from Senna macranthera var. nervosa (Vogel) H.S. Irwin & Barneby (Fabaceae). The chemical structure was elucidated and all 1 H and 13 C NMR chemical shifts were assigned by NMR one-( 1 HNMR, { 1 H}-13 CNMR, and APT-13 CNMR) and two (COSY, NOESY, HMQC and HMBC) dimensional of this natural compound. Furthermore, the minor anthraquinones chrysophanol (3), chrysophanol-8-methyl ether (4) and physcion (5) were characterized by GC-MS analysis. The occurrence of the anthraquinones 3-5 confirms that S. macranthera is a typical representative of the genus Senna.

Senna macranthera(Leguminosae), una especie ornamental naturalizada en la Argentina

“…En Brasil, recibe los nombres: "manduirana", "bolão de-ouro", "chuva-de-ouro", "fedegoso", "pau-de-ovelha" (Rodrigues et al, 2005), "aleluia" (Branco et al, 2011), "são João" (Kiill et al, 2000), "cabo verde", "ibixuna", "mamangá", "pau fava", "tararaçu" (Lorenzi, 1992).…”

“…Éstas contienen cumarinas, saponinas, taninos, flavonoides, compuestos fenólicos, triterpenoides, antronas y esteroides (Diaz et al, 2010;Guarize, 2009;Guarize et al, 2011). Se han aislado antraquinonas de la corteza (Branco et al, 2011) y de las raíces (Mendonça et al, 2011), utilizadas en la elaboración de pigmentos y medicamentos. Del endosperma de las semillas se han obtenido compuestos con actividad anticoagulante (Pires et al, 2001).…”

<i>Ex vivo</i> Inhibitory Activity of the Ethanol Root Extract of <i>Senna occidentalis</i> (Labaceae) on Isolated Rat Uterus

“…This may be due to presence of spasmolytic phytochemical constituents within the roots of the plant. Phytochemical analysis previously conducted on S. occidentalis reported the presence of anthraquinones, tannins, emodin and chrysarobin (Branco et al, 2011;Yadav et al, 2010) and these have been reported to possess a relaxant effect on smooth muscles (Akubue et al, 1983;Longanga et al, 2000). Anthraquinones have been specifically reported to decrease spontaneous contractions of rat intestinal and uterine smooth muscles (Odenthal and Ziegler, 1988).…”

Bioactivity of 1-octacosanol from Senna crotalarioides (Fabaceae: Caesalpinioideae) to Control Spodoptera frugiperda (Lepidoptera: Noctuidae)

“…Some species of the genus Senna are used as foods, ornamental plants, or with medicinal purposes (Mazzio & Soliman 2010), while others have become invasive species (Richardson & Rejmánek 2011;Singhurst et al 2013), or are considered as noxious woody weed (Parolin 2005). Previous phytochemical studies have allowed the identification of a variety of compounds found in Senna spp., including alkaloids (Moo-Puc et al 2007), anthraquinones (Branco et al 2011), cardiac glycosides (Essiett & Bassey 2013), glucosides (sennosides) (Monkheang et al 2011), naphthopyrones (Graham et al 2004), phenols (Viegas Junior et al 2013, saponins (Oluwole et al 2016), triterpenes, (Luximon-Ramma et al 2002, among others. The metabolic content of Senna species has been associated with a variety of biological properties, including insecticidal activity (Yagi et al 2013;de Souza Tavares et al 2014;Vasudev et al 2015).…”