Phragmalin Limonoids from Swietenia macrophylla and Their Antifeedant Assay against Mahogany Predator

Abstract

The purification of the hexanic extract from the leaves of a native variety of mahogany collected in Santarém (Pará, Brazil) afforded eight new phragmalin limonoids along with eight known compounds. This variety, according to field observations, should be considered resistant against the specialist insect Hypsipyla grandella, that attacks the terminal shoots only of juvenile mahogany and not of matured ones. After observing that four phragmalin limonoids were present just in mature leaves, we carried out two bioassays, one of them using a fraction from hexanic extract of mature leaves and another using a mix of four limonoids. The results of the bioassay using the isolated limonoids showed a direct effect on the larvae of H. grandella, suggesting that these limonoids act as inhibitors of larvae growth. This should be the reason why larvae choose the young leaves for their development.

Secure and Sustainable Sourcing of Plant Tissues for the Exhaustive Exploration of Their Chemodiversity

“…These marker compounds belong to the class of limonoids, which are taxonomic markers of the species. The mass spectra of these compounds were compared with those obtained from the substances isolated and identified by our group [ 12 , 40 , 41 ]. The chromatographic profiles of the samples ( Figure 6 ) associated with the four steps were compared to obtain a preliminary evaluation of the procedure.…”

“…Standards of the compounds 12α-acetoxyl-20β,21β-22α,23α-diepoxyswietephragmin C, 12α-acetoxyswietephragmin D, 3β- O -detigloyl-3β- O -benzoyl-6- O -acetylswietephragmin D, 6-acetoxy-12α-deacetoxyl-8,9,30-ortho-tigloylate-swietemacrophine, 12α-acetoxyswietephragmin C, 8,9,30- ortho -tigloylate swietemacrophine, 3β- O -detigloyl-3β- O -benzoyl-6- O -acetylswietephragmin E, 3β- O -detigloyl-3β- O -benzoyl-12α-acetoxyswietephragmin D were previously isolated from S. macrophylla leaves [ 12 , 40 , 41 ] standards physalin B, physalin G, physalin D and isophysalin B were from P . angulata leaves [ 39 ] and arabelline, 4- O -β- d -apiofuranosyl-(1′′′,6′′)-β-D-glucopyranosyl-diphyllin, 5- O -β-D-glucopyranosyljusticidin B, cleistanthin B, phyllanthostatin A, tuberculatin and justicidin B from the leaves of P. brasiliensis [ 48 ].…”

Research progress of meliaceous limonoids from 2011 to 2021

“…The distribution of phragmalin-class limonoids ( C295–C669 ) in plants is similar to mexicanolide-class and is almost concomitant, except that phragmalins are mainly present in the genus Chukrasia (138, 37.4%, accounts for 93% of limonoids from the genus Chukrasia ). 69,262,267–286 The genera Xylocarpus (59, 16.0%), 36,55,56,58,72,83,128,207,210,215,217,229,234,235,242,253,287–291 Trichilia (47, 12.7%), 62,233,247,292–297 and Swietenia (35, 9.5%) 219,246,248,298–302 also provide abundant phragmalin-class limonoids (Table S1.12†). The rest, about a quarter of phragmalins, are isolated from 10 genera.…”

Chemistry and Biology of Novel Meliaceae Limonoids

“…OAc; R 2 = Ac; R 3 = OH; R 4 = R 5 = H; R 6 = CH 3 Xylocarpus moluccensis 143 1144 Xylomolin L2 R 1 = OH; R 2 = Tig; R 3 = R 4 = H; R 5 = OH; R 6 = CH 3 Xylocarpus moluccensis 143 1145 12-Deacetylxyloccensin U R 1 = OH; R 2 = Ac; R 3 = R 4 = H; R 5 = OH; R 6 = CH 3 Xylocarpus moluccensis 352 1146 2-O-Acetyl-2-dehydroxy-12deacetylxyloccensin U OAc; R 2 = Ac; R 3 = R 4 = H; R 5 = OH; R 6 = CH 3 Xylocarpus moluccensis 352 1147 Andirolide Y R 1 = OCOCH 2 CH 3 ; R 2 = Ac; R 3 = OAc; R 4 = H; R 5 = OAc; R 6 = CH 3 Carapa guianensis 310 1148 Chukvelutilide N R 1 = OCOCH(CH 3 ) 2 ; R 2 = Ac; R 3 = R 4 = H; R 5 = OH; R 6 = CH 3 OH; R 2 = COCH(CH 3 ) 2 ; R 3 = R 4 = R 5 = H; Ac; R 3 = OH; R 4 = H; R 5 = OH Xylocarpus granatum 414 1160 12α-acetoxyswietephragmin I R 1 = OAc; R 2 = Tig; R 3 = R 4 = H; R 5 = OAC; R 6 = CH 3 Swietenia macrophylla 415 1161 3β-O-detigloyl-3β-O-benzoyl-12α-acetoxyswietephragmin I R 1 = OAc; R 2 = Bz; R 3 = R 4 = H; R 5 = OAc; R 6 = CH 3 Swietenia macrophylla 415 1162 8,9,30-ortho-tigloylateswietemacrophine R 1 = OH; R 2 = Tig; R 3 = R 4 = H; R 5 = OAc; R 6 = (E)-CH 3 C=CHCH 3 Swietenia macrophylla 415 1163 2-deacetyl-6-acetoxyl-swietephragmin I R 1 = OH; R 2 = Tig; R 3 = OAc; R 4 = R 5 = H; R 6 = CH 3 Swietenia macrophylla 415 2-deacetyl-12α-acetoxyswietephragmin I R 1 = OH; R 2 = Tig; R 3 = R 4 = H; R 5 = OAc; R 6 = CH 3 Swietenia macrophylla 415 3β-O-detigloyl-3β-O-benzoyl-6-O-acetylswietephragmin D R 1 = OH; R 2 = Bz; R 3 = OAc; R 4 = R 5 = H; R 6 = CH(CH 3 ) 2 Swietenia macrophylla 415 6-acetoxyl-12α-deacetoxyl-8,9,30ortho-tigloylate-swietemacrophine R 1 = OH; R 2 = Tig; R 3 = OAc; R 4 = R 5 = H; R 6 = ( OH; R 2 = Ac; R 3 = α-OH; R 4 = H; R 5 = OH; R 6 = CHXylocarpus moluccensis 337 2-O-acetylthaixylomolin Z R 1 = OAc; R 2 = Ac; R 3 = α-OH; R 4 = H; R 5 = OH; H; R 2 = Ac; R 3 = OAc; R 4 = H; R 5 = Ac; R6 = CH(CH 3 ) 2 Chukrasia tabularis 409 Chukbularisin D R 1 = H; R 2 = Ac; R 3 = OAc; R 4 = R 5 = Ac; R 6 = CH(CH 3 ) 2 Chukrasia tabularis 395 Chukbularisin E R 1 = COCH(CH 3 ) 2 ; R 2 = Ac; R 3 = OAc; R 4 = R 5 = Ac; R 6 = CH 3 Chukrasia tabularis 395 Chukvelutilide O R 1 = COCH(CH 3 ) 2 ; R 2 = Ac; R 3 = OH; R 4 = H; R 5 = Ac; R 6 = CH 3Chukrasia tabularis403 Tabularin R R 1 = R 2 = H; R 3 = OAc; R 4 = R 5 = Ac; R 6 = CH 3 Chukrasia tabularis 405 Chubularisin C R 1 = R 2 = R 3 = H; R 4 = Ac; R 5 = COCH(CH 3 ) 2 COCH(CH 3 ) 2 ; R 2 = Ac; R 3 = OAc; R 4 = Ac; R 5 = COCH(CH 3 ) 2 ; R 6 = CH 3Chukrasia tabularis410 Moluccensin Z1Chukrasia tabularis386 Hainanxylogranin RXylocarpus granatum152 Moluccensin Z2Chukrasia tabularis 386 12α-acetoxyl-20β,21β-22α,23αdiepoxyswietephragmin C Swietenia macrophylla415 …”