Constituents of the Root Wood of Austroplenckia populnea var. ovata

Abstract

The root wood of Austroplenckia populnea var. ovata was extracted successively with chloroform and methanol. Lapachol and dehydro-beta-lapachone were isolated from the chloroform extract, and euonine, alatusinine, wilfordine, 2-O-deacetyleuonine (1), 7-O-deacetyleuonine (2), and austronine (3) from the methanol extract. The structures of the new compounds 1-3 were elucidated by spectroscopic data interpretation. Lapachol, dehydro-beta-lapachone, euonine, alatusinine, and wilfordine are known compounds that are newly identified from root wood of Austroplenckia populnea.

Lapachol: An overview

“…In conclusion, the synthesis of lapachol was important for the varification of the structure but is of little practical value when considering the abundance this natural product as a metabolite in several tropical trees. A range of naphthoquinone derivatives, including phylloquinone (vitamin K 1 ) and menaquinone (vitamin K 2 ), are produced from chorismate (16) via isochorismate (17), 2succinoyl-6-hydroxycyclohexa-2,4-diene-1-carboxylate (SHCHC) (22), and orthosuccinoylbenzoate (OSB) (23) (Scheme 6). 72 The biosynthesis of OSB has been demonstrated for the first time in a Gram-positive bacterium, namely Bacillus subti1is.…”

“…Lapachol (1) has also been isolated from other families such as Verbenaceae, Proteaceae, Leguminosae, Sapotaceae, Scrophulariaceae, and Malvaceae (Table 1). Among the many significantly biologically active naphthoquinones, lapachol (1) is one of the most versatile biologically active compounds and its presence was sought and found later in several other species [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32] and different families as illustrated in Table 1.…”

Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

“…Althoughw eu sed no acid conditions, methoxylated stenocarpoquinone Ba nalogues 8 were not generated. 7-and 8-Methoxydehydro-a-lapachones 9b and 9c were prepared in 74 and 74 %y ield, respectively.T os ynthesize dehydro-b-lapachone 10 a, [23] dehydro-a-lapachone 9a was treated with TiCl 4 in CH 2 Cl 2 at 0 8Ct og ive the target product 10 a in 40 %y ield. However,t hese reaction conditions surprisingly provided dehydro-a-lapachone (9a, Scheme1.Preparation of lapacholsv ia the Heck reaction and synthesis of b-lapachones anddunniones.…”

“…68 %); [22] its carbon signal at the C10a position appeared at d C = 152.5 ppm, which is ac haracteristic signal of linear-type pyranonaphthoquinones. 7-and 8-Methoxydehydro-a-lapachones 9b and 9c were prepared in 74 and 74 %y ield, respectively.T os ynthesize dehydro-b-lapachone 10 a, [23] dehydro-a-lapachone 9a was treated with TiCl 4 in CH 2 Cl 2 at 0 8Ct og ive the target product 10 a in 40 %y ield. Presumably,t he ring-opening reactionw as driven by the in situ generation of at itanium(IV)dione complex, which was subsequently cyclized on the other side.…”

Pentacyclic Triterpenoids Isolated from Celastraceae: A Focus in the 13C-NMR Data

“…The following are available online, Table S1: Pentacyclic triterpenoids isolated from Celastraceae species (2001–2021) [ 257 , 258 , 259 , 260 , 261 , 262 , 263 , 264 , 265 , 266 , 267 , 268 , 269 , 270 , 271 , 272 , 273 , 274 , 275 , 276 , 277 , 278 , 279 , 280 , 281 , 282 , 283 , 284 , 285 , 286 , 287 , 288 , 289 , 290 , 291 , 292 , 293 , 294 , 295 , 296 , 297 , 298 , 299 , 300 , 301 , 302 , 303 , 304 , 305 , 306 , 307 ,…”