New nitrogenous and aromatic derivatives from Aglaia argentea and A. forbesii

Dumontet, Vincent; Thoison, Odile; Omobuwajo, O. R.; Martin, Marie‐Thérèse; Perromat, G.; Chiaroni, A.; Riche, C.; Païs, M.; Sévenet, Thierry; Hadi, A. Hamid A.

doi:10.1016/0040-4020(96)00322-5

Cited by 78 publications

(143 citation statements)

References 6 publications

Supporting

Mentioning

134

Contrasting

Order By: Relevance

“…These proton signals suggested that 1 is based on a typical cyclopenta [b]benzopyran skeleton as found previously in several other Aglaia species. 3,10,12,41,42 Besides the signals ascribed to the general cyclopenta [b]benzopyran skeletal feature, a putrescinyl 4-hydroxytiglate moiety was recognized. The latter was based on the carbon signals of four CH 2 groups at δ C 38.3 (C-13), 27.9 (C-14), 26.2 (C-15) and 39.8 (C-16), a carbonyl group at δ C 169.6 (C-18), a trisubstituted double bond at δ C 133.…”

Section: Resultsmentioning

confidence: 99%

Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis

Li¹,

Acuña²,

Li³

et al. 2013

Planta Med

View full text Add to dashboard Cite

Eight new compounds, including two cyclopenta [b]benzopyran derivatives (1, 2), two cyclopenta [b]benzofuran derivatives (3, 4), three cycloartane triterpenoids (5-7), and an apocarotenoid (8), together with 16 known compounds, were isolated from the chloroform-soluble partitions of separate methanol extracts of a combination of the fruits leaves and twigs, and of the roots of Aglaia perviridis collected in Vietnam. Isolation work was monitored using human colon cancer cells and facilitated with an LC/MS dereplication procedure. The structures of the new compounds (1-8) were determined on the basis of spectroscopic data interpretation. The Mosher ester method was employed to determine the absolute configurations of 5-7, and the absolute configurations of the 9,10-diol unit of compound 8 was established by a dimolybdenum tetraacetate [Mo 2 (AcO) 4 ] induced circular dichroism (ICD) procedure. Seven known rocaglate derivatives (9-15) exhibited significant cytotoxicity against the HT-29 cell line, with rocaglaol (9) being the most potent (ED 50 0.0007 µM). The new compounds 2-4 were also active against this cell line, with ED 50 values ranging from 0.46 to 4.7 µM. The cytotoxic compounds were evaluated against a normal colon cell line, CCD-112CoN. In addition, the new compound perviridicin B (2), three known rocaglate derivatives (9, 11, 12), as well as a known sesquiterpene, 2-oxaisodauc-5-en-12-al (17), showed significant NF-κB (p65) inhibitory activity in an ELISA assay.* Corresponding Author. Tel: +1-614-247-8094. Fax: +1-614-247-8119. kinghorn@pharmacy.ohio-state.edu. # Dedicated to Dr. Lester A. Mitscher, of the University of Kansas, for his pioneering work on the discovery of bioactive natural products and their derivatives ASSOCIATED CONTENT Supporting Information. 1 H, 13 C and 2D NMR spectra of compounds 1-8, 1 H NMR of (R)-and (S)-MTPA esters of 5-7. This material is available free-of-charge via the Internet at http://pubs.acs.org. NIH Public AccessAuthor Manuscript J Nat Prod. Author manuscript; available in PMC 2014 March 22. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author ManuscriptAglaia Lour., containing more than 120 species, is the largest genus of the plant family Meliaceae. 1 Aglaia species have attracted considerable interest in the area of natural products research, since they are a rich source of the "flavagline" class of bioactive agents. Flavagline derivatives have been proposed to be biogenetically derived from the coupling of a flavonoid unit and a cinnamic acid amide moiety, and can be divided into three subtypes, namely, the cyclopenta [b]benzofurans, the cyclopenta [b]benzopyrans, and the benzo [b]oxepines. [2][3][4][5] More than 100 flavaglines have been isolated from over 30 Aglaia species to date. [2][3][4][5] In a search for new anticancer agents from tropical plants, several Aglaia species, including Aglaia crassinervia, 6 A. edulis, 7 A. elliptica, 8 A. foveolata, 9-11 A. ponapensis, 12 and A. rubiginosa, 13 mainly collected from Indonesia, have been in...

show abstract

Section: Resultsmentioning

confidence: 99%

Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis

Li¹,

Acuña²,

Li³

et al. 2013

Planta Med

View full text Add to dashboard Cite

show abstract

“…Melting points (Yanaco micro melting-point apparatus) were uncorrected. 1 General procedure for the preparation of (2-allyloxyaryl)-2-propen-1-ol (3a-e) Under N 2 , the O-allyloxybenzaldehydes (2a-e) (30 mmol) dissolved in anhydrous THF (100 mL) was stirred and cooled to 0 o C and was subsequently added vinylmagnesium bromide (1.6 M) (22.5 mL, 36 mmol). The resulting mixture was stirred at 0 o C for 0.5 hr and then at room temperature for 2 hr and then, quenched with saturated aq.…”

Section: Methodsmentioning

confidence: 99%

“…The 1-benzoxepine moiety which plays a core structure both in naturally occurring products 1 and in certain synthetic biological molecules, 2 have abstracted the attention of chemists. In addition, benzoxepinone which has been employed as starting material, can be converted to corresponding quinoline by the Friedlander reaction, 3 and can be transformed into benzoxepine by isomerization of double bond, reduction of carbonyl group, and dehydration of giving alcohol in sequence.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1-benzoxepin-5-ones (ols) from salicylaldehydes via ring-closing metathesis

Li¹,

Chen²,

Chen³

et al. 2008

Arkivoc

View full text Add to dashboard Cite

show abstract

“…The benzofuran derivatives, isolated from natural sources as well as synthetic, show cytostatic and/or antitumor activity (e.g., [1][2][3][4][5][6][7][8][9]). Therein, neolignans isolated from the Persea species are cytotoxic in vitro to the human cancer cell lines: mouth epidermoid carcinoma, lung adenocarcinoma, and colon adenocarcinoma [7].…”

Section: Introductionmentioning

confidence: 99%

Derivatives of benzo[b]furan. Part II. Structural studies of derivatives of 2- and 3-benzo[b]furancarboxylic acids

et al. 2012

View full text Add to dashboard Cite

The selected derivatives of the 2-and 3-benzo [b]furancarboxylic acids were synthesized and their structures were studied using the X-ray crystallography and the computational methods. The monocarboxylic acids (1-3) crystallize as dimers stabilized by the O-HÁÁÁO intermolecular hydrogen bonds. Moreover, intramolecular hydrogen bonds are formed between the OH and C(=O)CH 3 groups, substituted to the aromatic ring (2-4). In the crystal structures of 1-4, weak C-HÁÁÁO, C-HÁÁÁp, and C-HÁÁÁBr interactions stabilize the three-dimensional packing of molecules. The crystalline sodium complex of 1 has the stoichiometry [Na 1 Á1A 2 Á1B]Á1C, thus, the asymmetric unit contains three different moieties of 1. In this complex, the Na ? cation is hexacoordinated having a strongly distorted tetragonal bipyramidal polyhedron. For each molecule 1-4, several conformers were obtained in the gas phase. It was achieved by the rotations of substituents [COOR and/or C(=O)CH 3 , where R = H, CH 3 ] with respect to the rigid benzo[b]furan system. As indicated by the quantum-chemical calculations, the solid-state conformers for 3 and 4 (3-benzo[b]furancarboxylic acid derivatives) are the most stable ones. In contrast, the solidstate conformers of the 2-benzo[b]furancarboxylic acid derivatives (1, 2) have the energies higher than the lowest energy conformer by 1.23 and 0.69 kcal/mol, respectively. It seems that intermolecular contacts in the crystal influence on the orientation of substituents, and the conformers observed in the sodium complex of 1 provide evidence of such flexibility.

show abstract

New nitrogenous and aromatic derivatives from Aglaia argentea and A. forbesii

Cited by 78 publications

References 6 publications

Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis

Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis

Synthesis of 1-benzoxepin-5-ones (ols) from salicylaldehydes via ring-closing metathesis

Derivatives of benzo[b]furan. Part II. Structural studies of derivatives of 2- and 3-benzo[b]furancarboxylic acids

Contact Info

Product

Resources

About