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Literature DB >> 20730041

Proteasome-inhibitory and cytotoxic constituents of Garcinia lateriflora: absolute configuration of caged xanthones.

Yulin Ren¹, Daniel D Lantvit, Esperanza J Carcache de Blanco, Leonardus B S Kardono, Soedarsono Riswan, Heebyung Chai, Charles E Cottrell, Norman R Farnsworth, Steven M Swanson, Yuanqing Ding, Xing-Cong Li, Jannie P J Marais, Daneel Ferreira, A Douglas Kinghorn.

Abstract

A new biflavonoid (1), a new xanthone enantiomer (2), five new caged xanthones (3-7), and several known compounds were isolated from the stem bark of Garcinia lateriflora, collected in Indonesia. The structures of the new compounds were determined by analysis of spectroscopic data, and the absolute configuration of the caged xanthones was shown for the first time at carbons 5, 7, 8, 8a, 10a, and 27, by analysis of COSY and NOESY NMR and ECD spectra. The biflavonoids exhibited proteasome inhibitory activity, and the known compound, morelloflavone (8) was found to have the greatest potency (IC(50) = 1.3 muM). The caged xanthones were cytotoxic towards HT-29 cells, with the known compound, morellic acid (10) being the most active (ED(50) = 0.36 muM). However, when tested in an in vivo hollow fiber assay, it was inactive at the highest dose tested (20 mg/kg).

Entities: CellLine Chemical Disease Gene Species

Year: 2010 PMID： 20730041 PMCID： PMC2923493 DOI： 10.1016/j.tet.2010.05.010

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

31 in total

1. Chemical constituents of Garcinia fusca: structure elucidation of eight new xanthones and their cancer chemopreventive activity.

Authors: Chihiro Ito; Masataka Itoigawa; Tomoko Takakura; Nijisiri Ruangrungsi; Fumio Enjo; Harukuni Tokuda; Hoyoku Nishino; Hiroshi Furukawa
Journal: J Nat Prod Date: 2003-02 Impact factor: 4.050

2. Caged-triprenylated and -tetraprenylated xanthones from the latex of Garcinia scortechinii.

Authors: Vatcharin Rukachaisirikul; Patima Painuphong; Yaowapa Sukpondma; Sorwaporn Koysomboon; Prakart Sawangchote; Walter C Taylor
Journal: J Nat Prod Date: 2003-07 Impact factor: 4.050

3. Synthesis of Optically Active endo,endo Bicyclo[2.2.2]octane-2,5-diol, Bicyclo[2.2.2]octane-2,5-dione, and Related Compounds.

Authors: Fredrik Almqvist; Niklas Ekman; Torbjörn Frejd
Journal: J Org Chem Date: 1996-05-31 Impact factor: 4.354

4. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds.

Authors: Nina Berova; Lorenzo Di Bari; Gennaro Pescitelli
Journal: Chem Soc Rev Date: 2007-02-05 Impact factor: 54.564

5. Polyprenylated xanthones from Garcinia lancilimba showing apoptotic effects against HeLa-C3 cells.

Authors: Quan-Bing Han; Hong-Lei Tian; Nian-Yun Yang; Chun-Feng Qiao; Jing-Zheng Song; Donald C Chang; Kathy Q Luo; Hong-Xi Xu
Journal: Chem Biodivers Date: 2008-12 Impact factor: 2.408

6. Antiviral activities of biflavonoids.

Authors: Y M Lin; M T Flavin; R Schure; F C Chen; R Sidwell; D L Barnard; J H Huffman; E R Kern
Journal: Planta Med Date: 1999-03 Impact factor: 3.352

7. The current state of ab initio calculations of optical rotation and electronic circular dichroism spectra.

Authors: T Daniel Crawford; Mary C Tam; Micah L Abrams
Journal: J Phys Chem A Date: 2007-11-07 Impact factor: 2.781

8. Theoretical calculation of electronic circular dichroism of the rotationally restricted 3,8''-biflavonoid morelloflavone.

Authors: Yuanqing Ding; Xing-Cong Li; Daneel Ferreira
Journal: J Org Chem Date: 2007-10-24 Impact factor: 4.354

9. Cytotoxic xanthones from Garcinia hanburyi.

Authors: J Asano; K Chiba; M Tada; T Yoshii
Journal: Phytochemistry Date: 1996-02 Impact factor: 4.072

Review 10. Use of the in vivo hollow fiber assay in natural products anticancer drug discovery.

Authors: Qiuwen Mi; John M Pezzuto; Norman R Farnsworth; Mansukh C Wani; A Douglas Kinghorn; Steven M Swanson
Journal: J Nat Prod Date: 2009-03-27 Impact factor: 4.050

10 in total

1. Investigation of Vietnamese plants for potential anticancer agents.

Authors: Lynette Bueno Pérez; Patrick C Still; C Benjamin Naman; Yulin Ren; Li Pan; Hee-Byung Chai; Esperanza J Carcache de Blanco; Tran Ngoc Ninh; Bui Van Thanh; Steven M Swanson; Djaja D Soejarto; A Douglas Kinghorn
Journal: Phytochem Rev Date: 2014-12 Impact factor: 5.374

2. Cytotoxic and NF-κB inhibitory sesquiterpene lactones from Piptocoma rufescens.

Authors: Yulin Ren; Ulyana Muñoz Acuña; Francisco Jiménez; Ricardo García; Melciades Mejía; Heebyung Chai; Judith C Gallucci; Norman R Farnsworth; Djaja D Soejarto; Esperanza J Carcache de Blanco; A Douglas Kinghorn
Journal: Tetrahedron Date: 2012-01-26 Impact factor: 2.457

3. Cytotoxic and NF-κB inhibitory constituents of the stems of Cratoxylum cochinchinense and their semisynthetic analogues.

Authors: Yulin Ren; Susan Matthew; Daniel D Lantvit; Tran Ngoc Ninh; Heebyung Chai; James R Fuchs; Djaja D Soejarto; Esperanza J Carcache de Blanco; Steven M Swanson; A Douglas Kinghorn
Journal: J Nat Prod Date: 2011-03-23 Impact factor: 4.050

Proteasome-inhibitory and cytotoxic constituents of Garcinia lateriflora: absolute configuration of caged xanthones.

1. Chemical constituents of Garcinia fusca: structure elucidation of eight new xanthones and their cancer chemopreventive activity.

2. Caged-triprenylated and -tetraprenylated xanthones from the latex of Garcinia scortechinii.

3. Synthesis of Optically Active endo,endo Bicyclo[2.2.2]octane-2,5-diol, Bicyclo[2.2.2]octane-2,5-dione, and Related Compounds.

4. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds.

5. Polyprenylated xanthones from Garcinia lancilimba showing apoptotic effects against HeLa-C3 cells.

6. Antiviral activities of biflavonoids.

7. The current state of ab initio calculations of optical rotation and electronic circular dichroism spectra.

8. Theoretical calculation of electronic circular dichroism of the rotationally restricted 3,8''-biflavonoid morelloflavone.

9. Cytotoxic xanthones from Garcinia hanburyi.

Review 10. Use of the in vivo hollow fiber assay in natural products anticancer drug discovery.

1. Investigation of Vietnamese plants for potential anticancer agents.

2. Cytotoxic and NF-κB inhibitory sesquiterpene lactones from Piptocoma rufescens.

3. Cytotoxic and NF-κB inhibitory constituents of the stems of Cratoxylum cochinchinense and their semisynthetic analogues.

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

5. Potential Anticancer Agents Characterized from Selected Tropical Plants.

6. Electrophilic aromatic prenylation via cascade cyclization.

7. Computational Study on the Conformations of Gambogic Acid.

8. Absolute configuration of (-)-gambogic acid, an antitumor agent.

9. Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors.

Review 10. Chemical and Biological Research on Herbal Medicines Rich in Xanthones.