ent-Abietane diterpenoids from Isodon xerophilus

Abstract

Three new ent-abietanoids, named xerophilusins XIV-XVI, and four known analogues, as well as four known chemical constituents were isolated from the leaves of Isodon xerophilus. Their structures were elucidated by extensive spectroscopic studies, and comparison with literature data. In addition, the cytotoxic activity of the ent-abietanoids against chronic myelogenous leukemia (K562), stomach adenocarcinoma (MKN45), and hepatocellular carcinoma (HepG2) human cell lines was investigated and no activities were observed.

(10E,12E,14E)-9,16-Dioxooctadeca-10,12,14-trienoic acid

“…This study is the first report of the presence of 9,16-dioxo-10E,12E,14E octadecatrienoic acid in the Caryophyllales order. This compound has previously been described only in the Asteraceae (Herz & Kulanthaivel, 1984) and Lamiaceae (Li et al, 2011) families.…”

“…For phytochemical investigation on Silene maritima With., see: Adrian-Romero et al (1998). For previous descriptions of the title compound, see: Herz & Kulanthaivel (1984); Li et al (2011). For lipoxygenase action on -linoleic acid, see: Vellosillo et al (2007).…”

Ent-Abietanoids Isolated from Isodon serra

“…Previous phytochemical investigations of this species have afforded abundant bioactive ent -kaurane diterpenoids [ 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. Our continuing research for bioactive constituents of the aerial parts of this plant collected in the E′mei mountain, Sichuan Province of China, has led to the discovery of eight diterpenoids, including four new ent -abietanoids, named serrin K ( 1 ), xerophilusin XVII ( 2 ), and enanderianins Q and R ( 3 and 4 ), together with four known analogues, rubescansin J ( 5 ), (3α,14β)-3,18-[(1-methylethane-1,1-diyl)dioxy]- ent -abieta-7,15(17)-diene-14,16-diol ( 6 ) [ 11 ], xerophilusin XIV ( 7 ) [ 12 ], and enanderianin P ( 8 ) [ 13 ] ( Figure 1 ). In contrast to the previous chemical investigations of this plant, this was the first discovery of the ent -abietane diterpenoids from this species.…”

Obtención y actividad antiinflamatoria de flavonoides y terpenoides aislados de Cayaponia tayuya e Isodon xerophilus

“…I. xerophilus representa una abundante fuente de compuestos terpenoides biológicamaente activos; de este grupo, miembros diterpenoides ent-abietanos y ent-kauranos, y triterpenoides fueron aislados e identificados a partir de extractos de sus hojas. Las investigaciones farmacológicas se enfocaron en la evaluación citotóxica de los compuestos aislados sobre líneas celulares tumorales humanas a fin de avalar el uso tradicional de la planta como antitumoral (Hou et al, 2000a(Hou et al, , 2000b(Hou et al, , 2001a(Hou et al, , 2001bMcClatchey y Stevens, 2001;Li et al, 2007, Li et al, 2011Sun et al, 2006;Tian et al, 2006;Weng et al, 2007;Zhang et al, 2014;Yao et al, 2015).…”

“…xerophilus, especie objeto de estudio en esta tesis doctoral, ha sido ampliamente usada como agente antitumoral, antiinflamatorio y antibacteriano por la población local de la provincia de Yunnan (Li et al, 2007;Li et al, 2011;Li et al, 2012). Las hojas utilizadas en la preparación de infusiones frías, conocidas con el nombre de "liang cha", se administran para el tratamiento y la prevención del dolor de garganta y muscular, fiebre, congestión e inflamación asociados al resfriado común (Weng et al, 2007).…”