Literature DB >> 17055270

Ponapensin, a cyclopenta[bc]benzopyran with potent NF-kappaB inhibitory activity from Aglaia ponapensis.

Angela A Salim1, Alison D Pawlus, Hee-Byung Chai, Norman R Farnsworth, A Douglas Kinghorn, Esperanza J Carcache-Blanco.   

Abstract

Two new compounds, a cyclopenta[bc]benzopyran, ponapensin (1), and an aglaialactone, 5,6-desmethylenedioxy-5-methoxy-aglalactone (2), together with nine known compounds were isolated from the CHCl(3) soluble extract of the leaves and twigs of Aglaia ponapensis. Their structures were established by spectroscopic data interpretation. Ponapensin (1) exhibited significant NF-kappaB inhibitory activity in an Elisa assay, and was found to be more potent than the positive control rocaglamide. All of the compounds isolated were also tested in a panel of human cancer cell lines, with the known sterol E-volkendousin (3) and methyl rocaglate (aglafoline) found to be the only active substances.

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Year:  2006        PMID： 17055270      PMCID： PMC2786496          DOI： 10.1016/j.bmcl.2006.09.084

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  11 in total

1.  Cytotoxic constituents of the twigs and leaves of Aglaia rubiginosa.

Authors:  J Fausto Rivero-Cruz; Hee-Byung Chai; Leonardus B S Kardono; Fransisca M Setyowati; Johar J Afriatini; Soedarsano Riswan; Norman R Farnsworth; Geoffrey A Cordell; John M Pezzuto; Steven M Swanson; A Douglas Kinghorn
Journal:  J Nat Prod       Date:  2004-03       Impact factor: 4.050

2.  Bisamides, lignans, triterpenes, and insecticidal Cyclopenta[b]benzofurans from Aglaia species.

Authors:  G Brader; S Vajrodaya; H Greger; M Bacher; H Kalchhauser; O Hofer
Journal:  J Nat Prod       Date:  1998-12       Impact factor: 4.050

3.  Cytostatic mechanism and antitumor potential of novel 1H-cyclopenta[b]benzofuran lignans isolated from Aglaia elliptica.

Authors:  S K Lee; B Cui; R R Mehta; A D Kinghorn; J M Pezzuto
Journal:  Chem Biol Interact       Date:  1998-10-02       Impact factor: 5.192

4.  Development of a sensitive multi-well colorimetric assay for active NFkappaB.

Authors:  P Renard; I Ernest; A Houbion; M Art; H Le Calvez; M Raes; J Remacle
Journal:  Nucleic Acids Res       Date:  2001-02-15       Impact factor: 16.971

5.  Diamide derivatives and cycloartanes from the leaves of Aglaia elliptica.

Authors:  A Inada; T Sorano; H Murata; Y Inatomi; D Darnaedi; T Nakanishi
Journal:  Chem Pharm Bull (Tokyo)       Date:  2001-09       Impact factor: 1.645

6.  Macharistol, a new cytotoxic cinnamylphenol from the stems of Machaerium aristulatum.

Authors:  E K Seo; N C Kim; Q Mi; H Chai; M E Wall; M C Wani; H A Navarro; J P Burgess; J G Graham; F Cabieses; G T Tan; N R Farnsworth; J M Pezzuto; A D Kinghorn
Journal:  J Nat Prod       Date:  2001-11       Impact factor: 4.050

Review 7.  NF-kappa B: a lesson in family values.

Authors:  D Thanos; T Maniatis
Journal:  Cell       Date:  1995-02-24       Impact factor: 41.582

Review 8.  Potential of cyclopenta[b]benzofurans from Aglaia species in cancer chemotherapy.

Authors:  Soyoung Kim; Angela A Salim; Steven M Swanson; A Douglas Kinghorn
Journal:  Anticancer Agents Med Chem       Date:  2006-07       Impact factor: 2.505

9.  Rocaglamide derivatives are potent inhibitors of NF-kappa B activation in T-cells.

Authors:  Bernd Baumann; Frank Bohnenstengel; Daniela Siegmund; Harald Wajant; Christoph Weber; Ingrid Herr; Klaus-Michael Debatin; Peter Proksch; Thomas Wirth
Journal:  J Biol Chem       Date:  2002-09-16       Impact factor: 5.157

Review 10.  NF-kappa B: arresting a major culprit in cancer.

Authors:  Burkhard Haefner
Journal:  Drug Discov Today       Date:  2002-06-15       Impact factor: 7.851
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  16 in total

1.  Phytochemical and Bioactivity Studies on Constituents of the Leaves of Vitex Quinata.

Authors:  Ye Deng; Young-Won Chin; Hee-Byung Chai; Esperanza Carcache de Blanco; Leonardus B S Kardono; Soedarsano Riswan; Djaja D Soejarto; Norman R Farnsworth; A Douglas Kinghorn
Journal:  Phytochem Lett       Date:  2011-09-01       Impact factor: 1.679

Review 2.  Natural products as aromatase inhibitors.

Authors:  Marcy J Balunas; Bin Su; Robert W Brueggemeier; A Douglas Kinghorn
Journal:  Anticancer Agents Med Chem       Date:  2008-08       Impact factor: 2.505

Review 3.  Chemistry and biology of rocaglamides (= flavaglines) and related derivatives from aglaia species (meliaceae).

Authors:  Sherif S Ebada; Neil Lajkiewicz; John A Porco; Min Li-Weber; Peter Proksch
Journal:  Prog Chem Org Nat Prod       Date:  2011

Review 4.  The relevance of higher plants in lead compound discovery programs.

Authors:  A Douglas Kinghorn; Li Pan; Joshua N Fletcher; Heebyung Chai
Journal:  J Nat Prod       Date:  2011-06-08       Impact factor: 4.050

5.  Enantioselective photocycloaddition of 3-hydroxyflavones: total syntheses and absolute configuration assignments of (+)-ponapensin and (+)-elliptifoline.

Authors:  Neil J Lajkiewicz; Stéphane P Roche; Baudouin Gerard; John A Porco
Journal:  J Am Chem Soc       Date:  2012-07-25       Impact factor: 15.419

Review 6.  Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species.

Authors:  Li Pan; John L Woodard; David M Lucas; James R Fuchs; A Douglas Kinghorn
Journal:  Nat Prod Rep       Date:  2014-05-02       Impact factor: 13.423

7.  Biomimetic photocycloaddition of 3-hydroxyflavones: synthesis and evaluation of rocaglate derivatives as inhibitors of eukaryotic translation.

Authors:  Stéphane P Roche; Regina Cencic; Jerry Pelletier; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-03       Impact factor: 15.336

8.  Dichamanetin inhibits cancer cell growth by affecting ROS-related signaling components through mitochondrial-mediated apoptosis.

Authors:  Yeonjoong Yong; Susan Matthew; Jennifer Wittwer; Li Pan; Qi Shen; A Douglas Kinghorn; Steven M Swanson; Esperanza J Carcache DE Blanco
Journal:  Anticancer Res       Date:  2013-12       Impact factor: 2.480

9.  Cytotoxic xanthone constituents of the stem bark of Garcinia mangostana (mangosteen).

Authors:  Ah-Reum Han; Jeong-Ah Kim; Daniel D Lantvit; Leonardus B S Kardono; Soedarsono Riswan; Heebyung Chai; Esperanza J Carcache de Blanco; Norman R Farnsworth; Steven M Swanson; A Douglas Kinghorn
Journal:  J Nat Prod       Date:  2009-11       Impact factor: 4.050

10.  Constituents of the Leaves and Stem Bark of Aglaia foveolata.

Authors:  Angela A Salim; Hee-Byung Chai; Ismail Rachman; Soedarsono Riswan; Leonardus B S Kardono; Norman R Farnsworth; Esperanza J Carcache-Blanco; A Douglas Kinghorn
Journal:  Tetrahedron       Date:  2007-08-13       Impact factor: 2.457
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