New Insecticidal Rocaglamide Derivatives from the Roots of Aglaia duperreana

Abstract

Bioassay-guided fractionation of an extract obtained from roots of Aglaia duperreana led to the isolation of 17 1H-cyclopenta[b]benzofurans of the rocaglamide type. Of the compounds isolated, four rocaglamide derivatives (2, 6, 11, and 16) were obtained as new natural products, and their structure elucidation was conducted by spectral methods. For bioassay-guided fractionation and determination of LC50 and EC50 values, neonate larvae of Spodoptera littoralis were employed. The results of chronic feeding assays have shown new aspects of the structure−activity relationship of rocaglamide derivatives. The substitution of a hydroxyl group at C-8b by a methoxyl substituent leads to a loss of insecticidal activity in a manner not previously documented in this compound class.

Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis

“…According to a previous study, only two naturally occurring rocaglaol analogues from A. duppereana, which were also isolated from A. perviridis in the present investigation as compounds 8b-O-methylrocaglaol and methyl 8b-O-methylrocaglate (16), have been reported to have the OH group at C-8b substituted by a methoxy group. 40 Furthermore, analysis of the additional NOE effects gave supporting evidence that the relative configuration of compound 3 is identical with those of previously reported rocaglaol derivatives. 7,40 Thus, the structure of 3 was determined as 8b-Omethyl-4′-demethoxy-3′,4′-methylenedioxyrocaglaol.…”

“…40 Furthermore, analysis of the additional NOE effects gave supporting evidence that the relative configuration of compound 3 is identical with those of previously reported rocaglaol derivatives. 7,40 Thus, the structure of 3 was determined as 8b-Omethyl-4′-demethoxy-3′,4′-methylenedioxyrocaglaol.…”

“…To avoid the re-isolation of only the same cytotoxic agents as from the plant parts investigated above, the CHCl 3 -soluble extract of A. perviridis root was subjected to an LC-MS dereplication procedure, 16). 40 The isolates were tested for their cytotoxicity against the HT-29 cancer cell line as well as the normal colon cell line, CCD-112CoN. Finally, the NF-κB (p65) inhibitory effects of these compounds were also evaluated using an ELISA assay.…”

“…In addition, the occurrence of unknown cytotoxic compounds was suggested with possible molecular formulas of C 29 H 28 O 9 and C 27 H 26 O 7 . Further fractionation on this extract led to the purification of six additional rocaglaol derivatives, including two new cyclopenta [b]benzofurans, 8b-Omethyl-4′-demethoxy-3′,4′-methylenedioxyrocaglaol (3) and methyl 8b-O-methyl-4′-demethoxy-3′,4′-methylenedioxyrocaglate (4), along with four rare known rocaglates, methyl 1-formyloxy-4′-demethoxy-3′,4′-methylenedioxyrocaglate (14), 7 methyl 1-formyloxyrocaglate (15), 39 8b-O-methylrocaglaol, 40 and methyl 8b-O-methylrocaglate (16). 40 The isolates were tested for their cytotoxicity against the HT-29 cancer cell line as well as the normal colon cell line, CCD-112CoN.…”

Diamide Derivatives and Cycloartanes from the Leaves of Aglaia elliptica.

“…Several novel amides containing a cyclopenta-[bc]benzopyran moiety (ϭaglain-type) and a cyclopenta- [b]benzofuran moiety (ϭrocaglamide-type) as the acid part have been characterized from this genus, [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] some of which were shown to exhibit cytotoxic 1,3,5,7,10,19,20) insecticidal, 2,6,8,9,[11][12][13][14][15]17) and antifungal 4) activities. In our series of studies of this genus, 16) we have investigated the constituents of the leaves of Aglaia elliptica Bl.…”