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

Ishibashi, Fumito; Satasook, Chutamas; Ismant, Murray B.; Towers, G.H.N.

doi:10.1016/s0031-9422(00)94986-0

Cited by 116 publications

(92 citation statements)

References 6 publications

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“…The relative configuration of 1 was established primarily by analysis of the splitting patterns, and the coupling constant values between H-1, H-2, and H-3 indicating a 1a, 2a, 3b configuration, as well as a cis-BC ring junction. [8][9][10] These relative configurations were confirmed by NOESY experiments, wherein correlations were observed from H-1 to H-2 and H-6Ј and from H-2 to H-3. Due to their structural similarity, all rocaglamide-related natural products that have so far been examined display CD spectra very similar to that of rocaglamide itself.…”

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confidence: 53%

“…Due to their structural similarity, all rocaglamide-related natural products that have so far been examined display CD spectra very similar to that of rocaglamide itself. 8,10,11) The CD curve of 1 was also very similar to that of rocaglamide, with a prominent negative cotton effect at 274 nm as the most characteristic feature, suggesting the presence of the usual rocaglamide-analogue absolute stereostructure, with a 1R, 2R, 3S, 3aR, 8bS-configuration. On the basis of the above evidence, the structure of 1 was characterized as 1-O-formylrocagloic acid.…”

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confidence: 67%

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Potent Cytotoxic Rocaglamide Derivatives from the Fruits of Amoora cucullata

Chumkaew

Kato

Chantrapromma

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Two new rocaglamide derivatives, 1-O-formylrocagloic acid (1) and 3-hydroxy rocagloic acid (2), together with five known compounds, rocaglaol (3), rocagloic acid (4), 3-hydroxymethylrocaglate (5), 1-O-formylmethyl rocaglate (6), and methylrocaglate (7), were isolated from the fruits of Amoora cucullata. Their structures were elucidated by spectroscopic methods. Compounds 1-3, 6, and 7 exhibited potent cytotoxicity against KB, BC, and NCI-H187 cell lines, whereas 4 and 5 showed selective cytotoxicity against NCI-H187 cell line.

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confidence: 53%

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confidence: 67%

Potent Cytotoxic Rocaglamide Derivatives from the Fruits of Amoora cucullata

Chumkaew

Kato

Chantrapromma

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Its molecular formula was assigned as C 30 (Table 3). These characteristic NMR data suggested that 5 possesses a cycloartane skeleton, which has been reported as one of the major classes of triterpenes isolated from Aglaia species.…”

Section: Resultsmentioning

confidence: 99%

Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis

Li¹,

Acuña²,

Li³

et al. 2013

Planta Med

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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...

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“…3,4 The plant is used in Indonesian folk medicine for the treatment of fever, diarrhea, contused wound, coughs and skin diseases. 4 Previous phytochemical studies on Aglaia plants reported the presence of rocaglamide, 5,6,7 bisamides, 8,9 sesquiterpenoids, 10,11 diterpenoids, 12,13 dammaranetype triterpenoids, [14][15][16] cycloartane-type triterpenoids, 17,18 and apotirucallane triterpenoids. 19,20 Although secondary metabolites of other Aglaia species have been investigated previously, the chemical composition of A. ellipticais yet to be reported.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxicity and Structure Activity Relationship of Dammarane-Type Triterpenoids from the Bark of Aglaia elliptica against P-388 Murine Leukemia Cells

et al. 2017

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− Six dammarane-type triterpenoids, dammar-24-en-3β-ol (1), 3β-epicabraleahydroxy lactone (2), (E)-25-hydroperoxydammar-23-en-3β,20-diol (3), dammar-24-en-3β,20-diol (4), 3β-acetyl-20S,24S-epoxy-25-hydroxydammarane (5), and 3β-epiocotillol (6) were isolated from the methanolic extract of the bark of Aglaia elliptica. The chemical structure were identified on the basis of spectroscopic evidence and by comparison with those spectra previously reported. Compounds 1 -6 were isolated first time from this plant. Compounds 1 -6, along with a known synthetic analog, cabraleone (7) were evaluated their cytotoxic activity against P-388 murine leukimia cells in vitro. Among those compounds 3β-acetyl-20S,24S-epoxy-25-hydroxydammarane (5) showed strongest cytotoxic activity with IC 50 value of 8.02 ± 0.06 μM.

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

Cited by 116 publications

References 6 publications

Potent Cytotoxic Rocaglamide Derivatives from the Fruits of Amoora cucullata

Potent Cytotoxic Rocaglamide Derivatives from the Fruits of Amoora cucullata

Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis

Cytotoxicity and Structure Activity Relationship of Dammarane-Type Triterpenoids from the Bark of Aglaia elliptica against P-388 Murine Leukemia Cells

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