Aglaia Odorata Research Articles

An insecticidal rocaglamide derivatives and related compounds from Aglaia odorata (Meliaceae)

Organic extracts of the twigs and leaves of Aglaia odorata yielded eight insecticidal cyclopentatetrahydrobenzofuran rocaglamide derivatives including three congeners which proved to be new natural products. Moreover, four new cyclopentatetrahydrobenzopyran aglain derivatives, as well as the known aminopyrrolidine odorine and odorinol, syringaresinol and flavonoid derivatives were also isolated. Structure elucidation of the new compounds is described and a rationale of the biosynthesis of the rocaglamide and aglain congeners is considered. The isolated rocaglamide derivatives exhibited strong insecticidal activity towards neonate larvae of the polyphagous pest insect Spodoptera littoralis when incorporated into artificial diet with LC50 values varying from 1.0‐8.0 ppm. The most active compounds showed LC50 values between 1.0 and 1.1 ppm, comparable to those of the insecticide azadirachtin, which was used as a positive control. The remaining compounds isolated from A. odorata were inactive with regard to insecticidal activity. # 1999 Elsevier Science Ltd. All rights reserved.

A revision of the structure of ferrugin from aglaia ferruginaea

The structure of ferrugin from Aglaia ferruginaea has been revised to be the same as rocaglaol which has been isolated from Aglaia odorata.

Insecticidal activity of Aglaia odorata extract and the active principle, rocaglamide, to the European corn borer, Ostrinia nubilalis Hübn. (Lep., Pyralidae)

Abstract: A standardized twig extract of the Asian shrub, Aglaia odorata Lour. (Meliaceae), and rocaglamide, a purified active principle of the extract, were evaluated for potential to control the European corn borer (Ostrinia nubilalis Hübn.), via incorporation into meridic diet fed to larvae. Life cycle bioassays using the extract revealed that it inhibited larval growth at all concentrations tested (12.5–100 p.p.m./fresh wt.) and delayed mean time to pupation from 24.1 days (control) to 83.8 days (50 ppm). Other effects include reduced pupal and adult weights and an increase in the frequency of deformed pupae. Investigation of consumption rates and dietary utilization in larvae feeding on diet containing the extract suggested that it acts via a combination of antifeedant and postingestive (toxic) actions. Life cycle bioassays using rocaglamide demonstrated that this compound is an extremely potent inhibitor of larval growth, with concentration dependent activity observed at dietary concentrations from 0.05‐0.02 ppm. Effects at these levels include severe reductions in growth and pupal weight, and increases in larval mortality and time to pupation. Rocaglamide appears to be as, or even more active, than the very effective botanical pesticide azadrachtin from the neem tree.

Cyclopentabenzofuran lignan protein synthesis inhibitors from Aglaia odorata.

In the course of screening for Ras function inhibitors, rocaglaol (1) and the related compounds, the known pyrimidinone (2) and the novel aglaiastatin (3), were isolated from a CHCI3 extract of the leaves of Aglaia odorata. The structure of 3 was elucidated as a novel cyclopentabenzofuran on the basis of its NMR spectroscopic data and by X-ray crystallographic analysis. These compounds (1-3) were potent inhibitors of the growth of K-ras-NRK cells, with IC50 values of 1-10 ng/mL, and induced normal morphology in K-ras-NRK cells at 10-30 ng/mL. They also specifically inhibited protein synthesis. Aglaiastatin (3) was slightly more potent than 1 and 2 in inhibiting cell growth. Aglaiastatin (3) reduced the amount of Ras, possibly by inhibiting its de novo synthesis.

Insecticidal bioactivity of crude extracts of Aglaia species (meliaceae)

Crude foliar extracts of 19 species of Aglaia (Meliaceae), mostly of Indo-Malaysian origin, were screened for larval growth inhibiting and insecticidal effects on the polyphagous lepidopteran Peridroma saucia (Noctuidea). Extracts of at least seven of these species significantly reduce larval growth of P. saucia. Aglaia odorata yielded the most inhibitory extracts, but there is significant (35-fold) geographical variation in the bioactivity of extracts within this widespread species. In addition, extracts of bark are significantly more active than foliar extracts. Foliar extracts significantly deter neonate larvae, but nutritional analyses of fourth instar larvae fed artificial diets laced with A. odorata extracts indicate that both diet consumption and dietary utilizatin are impaired. These results are similar to that obtained with pure (−)-rocaglamide, an insecticidal principle isolated from A. odorata. This species should provide a useful starting point for the development of a botanical insecticide.

Isolation and X-ray structure determination of a novel pyrimidinone from Aglaia odorata

A new pyrimidinone has been isolated from the Thai medicinal plant Aglaia odorata Lour., and its structure elucidated by X-ray crystallography and NMR spectroscopy; the results reveal a unique structural backbone of fused five- and six-membered rings.

Bisamides from Aglaia species: structure analysis and potential to reverse drug resistance with cultured cells.

The structure of pyramidatine [1], a new bisamide alkaloid from leaves of Aglaia pyramidata, was determined through extensive nmr studies, including homonuclear COSY, NOESY, APT, HETCOR, and selective INEPT techniques. Revision of the 13C-nmr assignment of piriferine [2], an alkaloid previously isolated from A. pirifera, was achieved by examination of several 2D nmr spectra (homonuclear COSY, NOESY, and HETCOR) and confirmed by selective INEPT nmr experiments. Evaluation of the cytotoxic potential of the two alkaloids, along with two other bisamides from Aglaia odorata, odorine [3] and 5'-epi-odorine [4], was carried out in eleven human cancer cell lines. None of these bisamides showed significant cytotoxicity. Nevertheless, piriferine [2], odorine [3], and 5'-epi-odorine [4] were found to inhibit the growth of the vinblastine-resistant KB cells by enhancing the anticancer activity of vinblastine.

Insecticidal 1 H-cyclopentatetrahydro[ b]benzofurans from Aglaia odorata

Bioassay-directed separation of a methanolic extract of the leaves of Aglaia odorata led to the isolation of a known cyclopentatetrahydrobenzofuran, rocaglamide, along with its congeners, desmethylrocaglamide, methyl rocaglate and rocaglaol. The structures of the three new compounds were determined on the basis of spectroscopic evidence and by comparisons of their 1H NMR data with those of rocaglamide. Rocaglamide and methyl rocaglate exhibited potent insecticidal activity both through growth inhibition and contact toxicity to the variegated cutworm, Peridroma saucia.

Rocaglamide, a natural benzofuran insecticide from Aglaia odorata

Rocaglamide, a highly substituted benzofuran, was isolated and identified as the active insecticidal constituent in the twigs of the Chinese rice flower bush, Aglaia odorata. This compound inhibits larval growth and is insecticidal to both variegated cutworms, Peridroma saucia and Asian armyworms, Spodoptera litura. LD 50 values for fourth-instar P. saucia larvae were found to be 0.32 μg larvae −1 topically and 0.34 μg larvae −1 orally. Dammarane triterpenes and aminopyrrolidine bis-amides such as odorinol isolated from A. odorata were inactive against P. saucia.

Constituents of thai medicinal plants - iv new nitrogenous compounds - odorine and odorinol

Two new nitrogenous compounds were isolated from the leaves of Aglaia odorata . Their structures were elucidated by spectral evidences as odorine (1) and odorinol (2).

Triterpenoids of Aglaia odorata. Configuration of trisubstituted epoxides

Structures are established for three dammarane triterpenoids [(1c), (3a), and (3c)] isolated from Aglaia odorata. The stereochemistry at C-24 of these compounds and of aglaiol (1a) has been elucidated. The possibility that (3c)(a 24,25-dihydroxy-3-ketone) is identical with aglaiondiol, previously described as 3β,25-dihydroxy-5α-dammar-20-en-24-one, is discussed. It is shown that the configuration of trisubstituted epoxides can be conveniently determined by acid-catalysed methanolysis and application of Horeau's method to the resulting methoxy-alcohol.

Triterpenoid constituents of thai medicinal plants—II : Isomeric aglaitriols and aglaiondiol

Three new tetracyclic triterpenes, aglaiondiol and two isomers of aglaitriol, were isolated from the light petroleum extracts of leaves of Aglaia odorata. The isomers of aglaitriol ( 2) were separated by fractional crystallisation of the triacetates which on hydrolysis gave the epimers 2c and 2d. The structures of 2c, 2d and aglaiondiol ( 3) have been established by interconversion with aglaiol ( 1).

Constituents of thai medicinal plants—I aglaiol

Five crystalline compounds have been isolated from the leaves of the oriental medicinal plant Aglaia odorata Lour. (Meliaceae). One of these (agliol) is a tetracyclic triterpene, C 30H 50O 2, which according to chemical reactions and spectra is shown to possess structure I. This formula was confirmed by correlation with a derivative from dammaradienyl acetate (VII).