Insecticidal flavaglines and other compounds from Fijian Aglaia species

Greger, Harald; Pacher, Thomas; Brem, Brigitte; Bacher, Markus; Hofer, Otmar

doi:10.1016/s0031-9422(00)00471-4

Cited by 82 publications

(66 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…FA was isolated from the roots of Aglaia australiensis C. M. Pannell (HG 662) collected in Atherton Tablelands, Queensland, Australia. The methanolic extract was partitioned between water and chloroform, and the lipophilic fraction was separated by preparative medium pressure liquid chromatography and thin-layer chromatography as described previously (61). FA was also chemically synthesized using a previously described synthetic route (62).…”

Section: Methodsmentioning

confidence: 99%

Therapeutic suppression of translation initiation modulates chemosensitivity in a mouse lymphoma model

Bordeleau

Robert²,

Gerard³

et al. 2008

J. Clin. Invest.

Self Cite

254

411

View full text Add to dashboard Cite

Disablement of cell death programs in cancer cells contributes to drug resistance and in some cases has been associated with altered translational control. As eukaryotic translation initiation factor 4E (eIF4E) cooperates with c-Myc during lymphomagenesis, induces drug resistance, and is a genetic modifier of the rapamycin response, we have investigated the effect of dysregulation of the ribosome recruitment phase of translation initiation on tumor progression and chemosensitivity. eIF4E is a subunit of eIF4F, a complex that stimulates ribosome recruitment during translation initiation by delivering the DEAD-box RNA helicase eIF4A to the 5′ end of mRNAs. eIF4A is thought to prepare a ribosome landing pad on mRNA templates for incoming 40S ribosomes (and associated factors). Using small molecule screening, we found that cyclopenta[b]benzofuran flavaglines, a class of natural products, modulate eIF4A activity and inhibit translation initiation. One member of this class of compounds, silvestrol, was able to enhance chemosensitivity in a mouse lymphoma model in which carcinogenesis is driven by phosphatase and tensin homolog (PTEN) inactivation or elevated eIF4E levels. These results establish that targeting translation initiation can restore drug sensitivity in vivo and provide an approach to modulating chemosensitivity.

show abstract

Section: Methodsmentioning

confidence: 99%

Therapeutic suppression of translation initiation modulates chemosensitivity in a mouse lymphoma model

Bordeleau

Robert²,

Gerard³

et al. 2008

J. Clin. Invest.

Self Cite

254

411

View full text Add to dashboard Cite

show abstract

“…For example, compound 8 shows excellent insecticidal activity against littoralis [2]. Moreover, aglaiastatin and dehydro-aglaiastatin with cyclopentane fused other cycle and show almost the same good insecticidal activity, indicating that the substituents at 1-position and 2-position have little effect on the insecticidal activity, which has been ever regarded as the major site for structural modification [3,4]. Owing to oxidative aglafolin containing b-keto ester unit, further structural modification and derivatization become much more easily.…”

Section: Studies On Synthesis and Biological Activity Of Oxidative Agmentioning

confidence: 99%

Studies on Synthesis and Biological Activity of Oxidative Aglafolin Derivatives

Wang

Xie

et al. 2014

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

in Wiley Online Library (wileyonlinelibrary.com).The synthesis of the key intermediate of rocaglamide, oxidative aglafolin, was studied, and its diastereoisomers were obtained. The amination of oxidative aglafolin was also investigated, affording amino derivatives. The preliminary bioassay results indicate that these new aglafolin derivatives showed certain degree of insecticidal and repellent activity against Plutella xylostella and Laphygma exigua.

show abstract

“…All of the above-mentioned NMR observations suggested that compound 5 is a cyclopenta[bc]benzopyran derivative containing a bisamide side chain. [4][5][6]13,15,[28][29][30] In the HMBC spectrum, correlations from the proton at δ H 4.37 (H-3) to δ C 172.1 (C-11) and 131.6 (C-2″, 6″) of the monosubstituted aromatic ring, and from the proton at δ H 4.22 (H-4) to δ C 109.9 (C-5a) and 172.1 (C-11), suggested that the locations of the aromatic ring and the pyrrolidine-type bisamide unit are at C-3 and C-4, respectively. The vicinal coupling constant (9.3 Hz) between H-3 and H-4 was only compatible with a H-3α and a H-4β configuration for this class of compound.…”

mentioning

confidence: 99%

Cytotoxic Flavaglines and Bisamides from Aglaia edulis.

Kim¹,

Chin²,

Su³

et al. 2007

J. Nat. Prod.

View full text Add to dashboard Cite

Two new cyclopenta [b]benzofurans, aglaroxin A 1-O-acetate (2) and 3′-methoxyaglaroxin A 1-Oacetate (3), a new benzo [b]oxepine, 19,20-dehydroedulisone A (4), and five new cyclopenta [bc]benzopyrans, edulirin A (5), edulirin A 10-O-acetate (6), 19,20-dehydroedulirin A (7), isoedulirin A (8), and isoedulirin B (9), were isolated from the bark of Aglaia edulis, along with one known cyclopenta [b]benzofuran, aglaroxin A (1). Additionally, four new amides, aglamides A-D (10-13), as well as three known compounds, aglalactone, scopoletin, and 5-hydroxy-3,6,7,4′-tetramethoxyflavone, were isolated from the leaves and/or twigs of this species. The structures of the new compounds (2-13) were elucidated by interpretation of their spectroscopic data. All isolates obtained in this study were evaluated for cytotoxicity against both several human cancer cell lines (Lu1, LNCaP, and MCF-7) and a non-tumorigenic (HUVEC) cell line. Among these isolates, the cyclopenta [b]benzofurans (1-3) exhibited potent in vitro cytotoxic activity (ED 50 range 0.001 to 0.8 μg/mL). Aglaroxin A 1-O-acetate (2) was further evaluated in the in vivo P388 lymphocytic leukemia model, by intraperitoneal injection, but found to be inactive in this model.The cyclopenta [b]benzofurans have been isolated only from the genus Aglaia (Meliaceae) and occur in two structurally related groups of compounds, the benzo [b]oxepines and cyclopenta [bc]benzopyrans. 1,2 These classes of compounds have been termed as "flavaglines" because their mutual biogenetic origin is postulated to involve a flavonoid unit linked to a cinnamic acid moiety. [3][4][5][6] Among the flavaglines, cyclopenta [b]benzofurans have received considerable recent attention as interesting lead compounds for cancer chemotherapy, [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] as a result of the cyclopenta [b]benzofuran derivative, rocaglamide from Aglaia elliptifolia, being found to exhibit antineoplastic activity in an in vivo model. 20 As a part of a National Cooperative Drug Discovery Group (NCDDG) program to discover new antitumor agents from plants, 21, 22 the leaves, twigs, and bark of Aglaia edulis (Roxb.) Wall. (Meliaceae) were separately collected in Indonesia. The chloroform-soluble partitions of the three methanol extracts of these three plant parts were subjected to detailed investigation due to their cytotoxic activities demonstrated against a small panel of human cancer cell lines. 3H, s) in the 1 H NMR spectrum suggested the presence of an acetyl group at C-1. Consistent with the 1 H NMR spectrum of compound 2, its 13 C NMR spectrum also displayed the signals for a disubstituted and a monosubstituted benzene ring, as well as for two quaternary carbons at δ C 101.0 (C-3a) and 93.3 (C-8b). In the HMBC spectrum of compound 2, correlations from H-1 and OAc to the signal at δ C 169.8 indicated the acetoxy group to be located at C-1, while correlations from resonances for H-2 and the two N-Me groups to the signal at δ C 167.5 suggested the location of the amide group at...

show abstract

Insecticidal flavaglines and other compounds from Fijian Aglaia species

Cited by 82 publications

References 26 publications

Therapeutic suppression of translation initiation modulates chemosensitivity in a mouse lymphoma model

Therapeutic suppression of translation initiation modulates chemosensitivity in a mouse lymphoma model

Studies on Synthesis and Biological Activity of Oxidative Aglafolin Derivatives

Cytotoxic Flavaglines and Bisamides from Aglaia edulis.

Contact Info

Product

Resources

About