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Two new rocaglamides, 8b-O-5-oxohexylrocaglaol (1) and elaeagnin (2), together with twelve known compounds, were isolated from the bark of Aglaia elaeagnoidea and the whole tree of A. odorata. Their structures were determined using spectroscopic methods, mainly 1D and 2D NMR. Cytotoxic activity against HepG2 human liver cancer cells of the isolated compounds was evaluated in vitro using the SRB assay. Three rocaglamide derivatives, dehydroaglaiastatin (13), 8b-O-5-oxohexylrocaglaol (1) and rocaglaol (5), exhibited significant effects with IC50 values of 0.69, 4.77 and 7.37 µM, respectively.

Pacar cina (Aglaia odorata Lour) is a plant that is widely used as an traditional medicine because of natural materials they contain. The study aims to from Pacar cina extracts and toxicity test of each extract and isolated compound by BSLT (Brine Shrimp Lethality Test) method. The method used in the maceration. In this study, the n-hexane, ethyl acetate, methanol extracts and β-sitosterol compound showed toxic effect (LC50 261,17; 110; 266,75 and 100 μg/mL, respectively). The toxicity degree among the three extracts and isolated compound is β-sitosterol > ethyl acetate > n-hexane > methanol.

Nine new flavaglines that are flavonol-diamide [3+2] adducts as well as 12 known flavaglines were isolated from the leaves of Aglaia odorata (Meliaceae). The new compounds included eight 2,3,4,5-tetrahydro-2,5-methanobenzo[b]oxepine derivatives, aglaodoratins A–H (1–8), and a tetrahydro-cyclopenta[b]benzofuran derivative, aglaodoratin I (9). X-ray single crystallographic analysis of compound 1 confirmed the structure and absolute configuration of 1. The absolute configuration of aglaodoratin I (9) was elucidated from ECD data. Aglaodoratin C (3), a rare C-10 carbonylated aglain-type derivative, demonstrated inhibition of HepG2 liver carcinoma cell proliferation via G2/M arrest and induced apoptotic cell death at a concentration of 25 μM.

Twelve compounds were isolated from the roots of Aglaia odorata. Their structures were established on the basis of NMR and MS data as rocaglaol (1), rocaglamide (2), eichlerialactone (3), sapelins A (4), isofouquierone (5), eichlerianic acid (6), shoreic acid (7), agladupol E (8), 3-epimeliantriol (9), cleomiscosins B (10), 2β,3β-dihydroxy-5α-pregnane-16-one (11) and β-D-glucopyranos-1-yl N-methylpyrrole-2-carboxylate (12). Among them, compounds 1 and 2 showed significant cytotoxicity against human cancer cell (HL-60, SMMC-7721, A-549, MCF-7 and SW480) with IC50 values of 0.007-0.095 μM, while compounds 3-5 and 10 and 11 showed moderate to no cytotoxicity (IC50 0.43 to values >40 μM). Compound 6 showed only weak cytotoxicity (IC50 6.87 to >40 μM) and its epmier 7 was completely inactivite (IC50>40 μM) in the assay. However, potent synergistic effect was observed when the molar ratio of 6 to 7 is between 4:1 and 1:1.

Phytochemical investigation of Aglaia odorata var. microphyllina led to the isolation of two new rocaglamide derivatives and three known ones. The structures of the two new compounds were elucidated as 8b-methoxy-desmethylrocaglamide ( 1 ) and 3′-hydroxy-8b-methoxy-rocaglamide ( 2 ) by spectroscopic techniques (IR, MS, 1D and 2D NMR) and comparing with published data. All the five compounds were evaluated for cytotoxic activity against K562 cell line by MTT method. The results indicated that the OH at 8b position was a decisive group for cytotoxic activity.

Chemical investigation of the leaves of the oriental medicinal plant Aglaia odorata resulted in the isolation of five compounds: two dolabellane diterpenoids, two dammarane triterpenoids and a protostane triterpenoid, along with twenty known compounds. Their structures were elucidated on the basis of extensive spectroscopic analysis and by comparison of their NMR spectroscopic data with those reported in the literature. The anti-inflammatory activities of all compounds were evaluated as inhibitory activities against lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264.7 cell lines. Eleven compounds possessed potent nitric oxide inhibitory activity with IC(50) values ranging from 2.1 to 14.2 μM, these being better than that of the positive control, indomethacin (IC(50)=14.5 μM). In addition, three compounds exhibited significant activity against PGE(2) release with IC(50) values of 2.6, 16.1 and 23.0 μM.

A bioassay-guided fractionation of the allelochemicals of the ethyl acetate fraction extracted from Aglaia odorata led to isolation of a bisamide, odorine. The growth inhibitory effects of odorine and ethyl acetate fraction were studied for comparison on Echinochloa crus-galli. Odorine and ethyl acetate fraction of A. odorata could inhibit the germination and seedling growth of E. crus-galli, with ethyl acetate fraction being more potent. Thus, ethyl acetate fraction was selected for further experiment, E. crus-galli seeds were studied the effects of the ethyl acetate fraction from A. odorata leaves in wettable powder formulation on imbibition and α-amylase activity. It was found that treated seeds showed lower imbibition and α-amylase activity. The results of cytogenetic bioassay in Allium cepa roots showed that ethyl acetate fraction inhibited cell mitosis and induced mitotic abnormalities resulting from its action on chromatin organization and mitotic spindle in the exposed roots.

A long chain alcohol, 1-eicosanol together with two sterols, β-sitosterol and stigmasterol had been isolated from hexane extract of stem bark of pacar cina (Aglaia odorata Lour) (Meliaceae). These structures had been established based on spectroscopic data (IR and NMR) and by comparison to those of standard compounds. Keywords: Aglaia odorata Lour, Alcohol, Meliaceae, Sterol

The very pleasant (flowery, hay- and tea-like, woody) smelling essential oil of the flowers of Aglaia odorata Lour. (Meliaceae) consists mainly of cadinane derivatives (ca. 48%, including 27% of δ-cadinene, 24). A main constituent is muurola-4,10(14)-dien-1β-ol (4%, 37), accompanied by the new epimeric 1α-alcohol, 54. Methyl jasmonates (4%, 36, 50) obviously make an important odour contribution. Copyright © 1999 John Wiley & Sons, Ltd.

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.

[structure: see text] A novel triterpenoid, 21,25-cyclodammar-20(22)-ene-3beta,24alpha-diol, has been isolated from Aglaia odorata. Its structure was elucidated on the basis of 1D- and 2D-NMR and MS spectra and then confirmed by X-ray diffraction. It represents a new type of natural five-membered-ring triterpenoid, named cyclodammarane. Its possible biopathway was that squalene-2,3;22,23-diepioxide was directly cyclized to form 24,25-epoxydammar-20(21)-en-3-ol, followed by protonation of the remaining 24,25-epoxide and the cation attacking 21(20) methylene to generate the E ring.

1 A new dammarane triterpene, 3-acetoxy aglinin C (), and a new aglain, 10-oxo-aglaxiflorin D (2), along with five known compounds, 3 - 7, were isolated from the leaves of Aglaia odorata using chromatographic methods. The structures of 1 and 2 were determined on the basis of spectroscopic analyses. Bioactivities of 1 - 7 against AGZY 83-a (human lung cancer cell line) and SMMC-7721 (human liver cancer cell line) cells were determined.

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 Hubn.), 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.

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.

The title compound, known as odorine or roxburghiline {systematic name: (S)-N-[(R)-1-cinnamoylpyrrolidin-2-yl]-2-methylbutanamide}, C18H24N2O2, is a nitrogenous compound isolated from the leaves of Aglaia odorata. The absolute configuration was determined by refinement of the Flack parameter with data collected using Cu Kα radiation showing positions 2 and 2′ to be S and R, respectively. The pyrrolidine ring adopts an envelope conformation. In the crystal, molecules are linked into chains along [010] by intermolecular N—H...O hydrogen bonds.

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.

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. LD50 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.

Eight flavaglines, six cyclopenta[b]benzofurans, a cyclopenta[bc]benzopyran, and a benzo[b]oxepine, together with an aromatic butyrolactone were isolated from Aglaia odorata, A. elaeagnoidea, and A. edulis (Meliaceae) and tested against the three plant pathogens Pyricularia grisea, Fusarium avenaceum, and Alternaria citri for antifungal properties. Using the microdilution technique linked with digital image analysis of germ tubes, the benzofurans displayed strong activity, whereas the benzopyran, benzoxepine, and butyrolactone were inactive at the highest concentration tested. P. grisea, responsible for rice blast disease, was the most susceptible fungus against all benzofurans, with rocaglaol as the most active derivative. Based on EC(50), EC(90), and MIC values, the antifungal activity of rocaglaol was clearly higher than of the reference compounds, blasticidin S and Benlate.

Eleganoside A (1) and odoratanone A (15), a triterpenoid trisaccharide glycoside and a nortriterpenoid, together with twelve known compounds (2–13) and a mixture of cerebrosides (14) were isolated from Gelsemium elegans and Aglaia odorata. Their structures were elucidated by extensive spectroscopic and spectrometric analysis. Eleganoside A (1) features a 3- O-α-L-rhamnopyranosyl (1→4)-β-D-glucopyranosyl (1→4)-β-D-glucopyranoside of a peculiar 3,16-dihydroxyl-lanosta-8,24-dien-26-oic acid triterpenoid skeleton, and odoratanone A (15) is a 29-norcycloartane-type triterpenoid bearing an unusual five-membered methyl acetal ring. Anti-acetylcholinesterase/butyrylcholinesterase (AChE/BChE) assay indicated that at 50 μM, ethyl caffeate (5) was promising as a dual inhibitor of AChE and BChE, and paeonol (3) and 24-hydroperoxy-24-vinylcholesterol (9) exhibited BChE-selective inhibition.

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.

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 30 H 50 O 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).

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.