Literature DB >> 17326683

Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest.

Brent J Yoder1, Shugeng Cao, Andrew Norris, James S Miller, Fidy Ratovoson, Jeremi Razafitsalama, Rabodo Andriantsiferana, Vincent E Rasamison, David G I Kingston.   

Abstract

Bioassay-guided fractionation of an extract of the fruit of Macaranga alnifolia from Madagascar led to the isolation of four new prenylated stilbenes, schweinfurthins E-H (1-4), and one new geranylated dihydroflavonol, alnifoliol (5). The known prenylated stilbene vedelianin (6) and the known geranylated flavonoids bonanniol A (7), diplacol (8), bonannione A (9), and diplacone (10) were also isolated. All 10 compounds were tested for antiproliferative activity in the A2780 human ovarian cancer cell line assay. Vedelianin (IC50 = 0.13 microM) exhibited the greatest activity among all isolates, while schweinfurthin E (IC50 = 0.26 microM) was the most potent of the new compounds.

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Year:  2007        PMID： 17326683      PMCID： PMC2614403          DOI： 10.1021/np060484y

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  16 in total

1.  Mappain, a new cytotoxic prenylated stilbene from Macaranga mappa.

Authors:  J E van Der Kaaden; T K Hemscheidt; S L Mooberry
Journal:  J Nat Prod       Date:  2001-01       Impact factor: 4.050

2.  Antifungal clerodane diterpenes from Macaranga monandra (L) Muell. et Arg. (Euphorbiaceae).

Authors:  Martin A Salah; Erdal Bedir; Ngeh J Toyang; Ikhlas A Khan; M Dewayne Harries; David E Wedge
Journal:  J Agric Food Chem       Date:  2003-12-17       Impact factor: 5.279

3.  Potential cancer chemopreventive constituents of the leaves of Macaranga triloba.

Authors:  Dae Sik Jang; Muriel Cuendet; Alison D Pawlus; Leonardus B S Kardono; Kazuko Kawanishi; Norman R Farnsworth; Harry H S Fong; John M Pezzuto; A Douglas Kinghorn
Journal:  Phytochemistry       Date:  2004-02       Impact factor: 4.072

4.  Synthesis of nonracemic 3-deoxyschweinfurthin B.

Authors:  Jeffrey D Neighbors; John A Beutler; David F Wiemer
Journal:  J Org Chem       Date:  2005-02-04       Impact factor: 4.354

5.  Constituents of the leaves of Macaranga tanarius.

Authors:  Suporn Phommart; Pakawadee Sutthivaiyakit; Nitirat Chimnoi; Somsak Ruchirawat; Somyote Sutthivaiyakit
Journal:  J Nat Prod       Date:  2005-06       Impact factor: 4.050

6.  Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.

Authors:  J A Beutler; R H Shoemaker; T Johnson; M R Boyd
Journal:  J Nat Prod       Date:  1998-12       Impact factor: 4.050

7.  C-geranyl compounds from Mimulus clevelandii.

Authors:  W R Phillips; N J Baj; A A Gunatilaka; D G Kingston
Journal:  J Nat Prod       Date:  1996-05       Impact factor: 4.050

8.  Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: differences of bioactivity in the enantiomeric series.

Authors:  Nolan R Mente; Andrew J Wiemer; Jeffrey D Neighbors; John A Beutler; Raymond J Hohl; David F Wiemer
Journal:  Bioorg Med Chem Lett       Date:  2006-12-12       Impact factor: 2.823

9.  Radiation survival parameters of antineoplastic drug-sensitive and -resistant human ovarian cancer cell lines and their modification by buthionine sulfoximine.

Authors:  K G Louie; B C Behrens; T J Kinsella; T C Hamilton; K R Grotzinger; W M McKoy; M A Winker; R F Ozols
Journal:  Cancer Res       Date:  1985-05       Impact factor: 12.701

10.  A new prenylated flavonoid from propolis collected in Okinawa, Japan.

Authors:  Shigenori Kumazawa; Hitomi Goto; Tomoko Hamasaka; Syuichi Fukumoto; Takunori Fujimoto; Tsutomu Nakayama
Journal:  Biosci Biotechnol Biochem       Date:  2004-01       Impact factor: 2.043
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  29 in total

1.  Structural analogues of schweinfurthin F: probing the steric, electronic, and hydrophobic properties of the D-ring substructure.

Authors:  Natalie C Ulrich; John G Kodet; Nolan R Mente; Craig H Kuder; John A Beutler; Raymond J Hohl; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2010-01-04       Impact factor: 3.641

2.  Design, synthesis and 3D-QSAR study of cytotoxic flavonoid derivatives.

Authors:  Lili Ou; Shuang Han; Wenbo Ding; Zhe Chen; Ziqi Ye; Hongyu Yang; Goulin Zhang; Yijia Lou; Jian-Zhong Chen; Yongping Yu
Journal:  Mol Divers       Date:  2010-11-14       Impact factor: 2.943

3.  Fluorescent schweinfurthin B and F analogs with anti-proliferative activity.

Authors:  Joseph J Topczewski; Craig H Kuder; Jeffrey D Neighbors; Raymond J Hohl; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2010-07-29       Impact factor: 3.641

4.  Antiproliferative xanthones of Terminalia calcicola from the Madagascar rain forest.

Authors:  Shugeng Cao; Peggy J Brodie; James S Miller; Richard Randrianaivo; Fidy Ratovoson; Chris Birkinshaw; Rabodo Andriantsiferana; Vincent E Rasamison; David G I Kingston
Journal:  J Nat Prod       Date:  2007-02-27       Impact factor: 4.050

5.  Synthesis of indole analogues of the natural schweinfurthins.

Authors:  John G Kodet; David F Wiemer
Journal:  J Org Chem       Date:  2013-09-05       Impact factor: 4.354

6.  A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway.

Authors:  Tianhong Yang; Lingling Fang; Agnes M Rimando; Victor Sobolev; Keithanne Mockaitis; Fabricio Medina-Bolivar
Journal:  Plant Physiol       Date:  2016-06-29       Impact factor: 8.340

7.  Synthesis and structure activity relationships of schweinfurthin indoles.

Authors:  John G Kodet; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2014-03-06       Impact factor: 3.641

8.  Molecular and cellular dissection of the oxysterol-binding protein cycle through a fluorescent inhibitor.

Authors:  Tiphaine Péresse; David Kovacs; Mélody Subra; Joëlle Bigay; Meng-Chen Tsai; Joël Polidori; Romain Gautier; Sandy Desrat; Lucile Fleuriot; Delphine Debayle; Marc Litaudon; Van-Cuong Pham; Jérôme Bignon; Bruno Antonny; Fanny Roussi; Bruno Mesmin
Journal:  J Biol Chem       Date:  2020-02-19       Impact factor: 5.157

9.  Synthesis of amide isosteres of schweinfurthin-based stilbenes.

Authors:  David P Stockdale; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2017-08-09       Impact factor: 3.641

10.  Schweinfurthins I and J from Macaranga schweinfurthii.

Authors:  Paul Klausmeyer; Que N Van; Johnson Jato; Thomas G McCloud; John A Beutler
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050
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