A Novel Chlorinated Diphenyl Ether fromByrsonima microphylla(Malpighiaceae)

NEW DEGRADED QUINONE DITERPENOID FROM THE STEMS OF Byrsonima coccolobifolia Kunth. (Malpighiaceae)

“…Naphthoquinones, their derivatives, xanthones, and terpene derivatives have been isolated previously from members of this genus. 4,19,20,23 Quinones are derived from the oxidation of phenolic compounds; the oxidation of catechols (1,2-dihydroxybenzenes) leads to orthoquinones, and the oxidation of quinols (1,4-dihydroxybenzenes) leads to para-quinones. Accordingly, terpenoid quinones are built up from shikimate and terpenoid pathways.…”

“…The phytochemical investigation of the leaves and stems afforded the flavonoids (+)-catechin, (-)-epicatechin, quercitrin and isoquercitrin, which are frequently found in Byrsonima species including B. basiloba, 6,7 B. bucidaefolia, 8 B. crassa, 9,10 B. crassifolia, [11][12][13][14] B. fagifolia, [15][16][17] B. intermedia, 18 B. microphylla, 19,20 and B. verbascifolia; 21,22 the investigation also afforded the tannins 3,5-di-O-galloylquinic acid, 5-O-galloylquinic acid, 5-O-(3-methylgalloyl)-quinic acid, 3,4,5-tri-O-galloylquinic acid and gallic acid, which have been previously described in B. crassa 9,10 and B. fagifolia. [15][16][17] Among the compounds isolated from the stems of B. coccolobifolia, (+)-syringaresinol and trigonostemone are new in the genus Byrsonima.…”

“…[3][4][5] The compounds most commonly isolated from this genus are flavonoids, terpenes, gallic acids and quinic acid derivatives. 1 Among the constituents, flavonoids (flavanones, bioflavonoids, flavonols and procyanidins), triterpenes (with oleanolic and ursolic skeletons) and modified triterpenoids (steroids) are commonly found in B. basiloba, 6,7 B. bucidaefolia, 8 B. crassa, 9,10 B. crassifolia, [11][12][13][14] B. fagifolia, [15][16][17] B. intermedia, 18 B. microphylla, 19,20 and B. verbascifolia. 21,22 Previous studies on the leaves of B. coccolobifolia revealed the presence of flavonoids, gallic acid and xanthones.…”

Naturally Occurring Asterric Acid Analogs: Chemistry and Biology

“…Methyl asterrate (3) was reported to perform weak cytotoxic activities against diverse tumor cell lines, including HepG2, HL-60, MOLT-3, MCF-7, NCI-H460, and SF-268 cell lines. 63,64 Asterric acid (1), geodin hydrate (12), methyl dichloroasterrate (17), methyl chloroasterrate (18), neogeodin hydrate (27), and iizukine A (29) all manifested cytotoxic effects on HL-60, BEL-7402, and A-549 cell lines to various degrees. 32 Butyl 2,4-dichloroasterrate ( 22) and 3-methylpentyl-2,4-dichloroasterrate (30) performed weak cytotoxic activity against HL-60, HCT116, PC-3, and HT-29 cancer cell lines.…”

“…72−75 Asterric acid analogs (48−51) were found to exert potent scavenging effects on the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical with max radical scavenging rates of 88.6− 103.3% and antioxidant activity in oxygen radical absorbance capacity (ORAC) assay with 3.2−12.8 ORAC units. 43 Corynether A (57) also displayed moderate antioxidant activity with 4.3 ORAC units, 47 and neogeodin hydrate (27) showed inhibition against superoxide anion radical formation by xanthine/xanthine oxidase (XXO) with an IC 50 value of 179.1 ± 13.1 μM but no inhibitory activity against aromatase enzyme. 30 The investigators suggested that the phenolic hydroxy group might be the functional group.…”