Kingianic Acids A-G, Endiandric Acid Analogues from Endiandra kingiana

Molecules

Volumn 19, Issue 2, 2014, Pages 1732-1747

  Azmi, Mohamad Nurul ^a   Gény, Charlotte ^b   Leverrier, Aurélie ^b   Litaudon, Marc ^b   Dumontet, Vincent ^b   Birlirakis, Nicolas ^b   Guéritte, Françoise ^b   Leong, Kok Hoong ^a   Halim, Siti Nadiah Abd ^a   Mohamad, Khalit ^a   Awang, Khalijah ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b CNRS   (France)

Author keywords

Anti apoptotic proteins; Bcl xL; Endiandra kingiana; Endiandric acids; Kingianic acids; Lauraceae; Mcl 1

Indexed keywords

ANTINEOPLASTIC AGENT; CARBOXYLIC ACID; ENDIANDRIC ACID; PLANT EXTRACT;

APOPTOSIS; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; HT 29 CELL LINE; HUMAN; LAURACEAE; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CARBOXYLIC ACIDS; DRUG SCREENING ASSAYS, ANTITUMOR; HT29 CELLS; HUMANS; LAURACEAE; MOLECULAR STRUCTURE; PLANT EXTRACTS; X-RAY DIFFRACTION;

EID: 84894618121     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19021732     Document Type: Article

References (32)

1. Litaudon, M.; Bousserouel, H.; Awang, K.; Nosjean, O.; Martin, M.-T.; Tran Huu Dau, M.-E.; Hadi, H.A.; Boutin, J.A.; Sévenet, T.; Guéritte, F. A dimeric sesquiterpenoid from a Malaysian Meiogyne as a new inhibitor of Bcl-xL/BakBH3 domain peptide interaction. J. Nat. Prod. 2009, 72, 480-483.
2. Leverrier, A.; Dau, M.E.T.H.; Retailleau, P.; Awang, K.; Guéritte, F.; Litaudon, M. Kingianin A: A new natural pentacyclic compound from Endiandra kingiana. Org. Lett. 2010, 12, 3638-3641.
3. Leverrier, A.; Martin, M.-T.; Servy, C.; Ouazzani, J.; Retailleau, P.; Awang, K.; Mukhtar, M.R.; Guéritte, F.; Litaudon, M. Rearranged diterpenoids from the biotransformation of ent trachyloban-18-oic acid by Rhizopus arrhizus. J. Nat. Prod. 2010, 76, 1121-1125.
4. Leverrier, A.; Awang, K.; Guéritte, F.; Litaudon, M. Pentacyclic polyketides from Endiandra kingiana as inhibitors of the Bcl-xL/Bak interaction. Phytochemistry 2011, 72, 1443-1452.
5. Ng, F.S.P. Tree Flora of Malaya, a Manual for the Forester; Whitmore, T.C., Ed.; Longman: Kuala Lumpur, Malaysia, 1989; Volume 4, p. 141.
6. Burkill, I.H. A Dictionary of the Economic Products of the Malay Peninsular, 2nd ed.; Government of Malaya and Singapore: Kuala Lumpur, Malaysia, 1966; p. 1773.
7. Maberley, D.J. Mabberley's Plant-Book: A Portable Dictionary of Plants, Their Classification and Uses, 3rd ed.; Cambridge University Press: Cambridge, UK, 2008; p. 1021.
8. Bandaranayake, W.M.; Banfield, J.E.; Black, D.S.C.; Fallon, G.D.; Gatehouse, B.M. Endiandric acid, a novel carboxylic acid from Endiandra introrsa (Lauraceae): X-Ray structure determination. J. Chem. Soc. Chem. Commun. 1980, 162-163, doi:10.1039/C39800000162.
9. Bandaranayake, W.M.; Banfield, J.E.; Black, D.S.C.; Fallon, G.D.; Gatehouse, B.M. Constituents of Endiandra species. I. Endiandric acid, a novel carboxylic acid from Endiandra introrsa (Lauraceae) and a derived lactone. Aust. J. Chem. 1981, 34, 1655-1667.
10. Bandaranayake, W.M.; Banfield, J.E.; Black, D.S.C.; Fallon, G.D.; Gatehouse, B.M. Constituents of Endiandra species. III. 4-[(E,E)-5'-Phenylpenta- 2',4'-dien-1'-yl]tetracyclo[ 5,4,0,02,5,03,9]undec-10-ene-8-carboxylic acid from Endiandra introrsa (Lauraceae). Aust. J. Chem. 1982, 35, 567-579.
11. Bandaranayake, W.M.; Banfield, J.E.; Black, D.S.C. Constituents of Endiandra species. II. (E)-4-(6'-phenyltetracyclo[5.4.2.03,13.010,12]trideca-4', 8'-dien-11'yl)but-2-enoic acid from Endiandra introrsa (Lauraceae) and a derived lactone. Aust. J. Chem. 1982, 35, 557-565.
12. Bandaranayake, W.M.; Banfield, J.E.; Black, D.S.C. Postulated electrocyclic reactions leading to endiandric acid and related natural products. J. Chem. Soc. Chem. Commun. 1980, 902-903, doi:10.1039/C39800000902.
13. Banfield, J.E.; Black, D.S.C.; Fallon, G.D.; Gatehouse, B.M. Constituents of Endiandra species. V. 2-[3',5'-Dioxo-4'-phenyl-10'-{(E,E)-5''-phenyl-penta- 2'',4''-dien-1''-yl}-2',4',6'-triazatetracyclo [5,4,2,02,6,08,11] tridec12'-en-9'-yl]-acetic acid derived from Endiandra introrsa (Lauraceae). Aust. J. Chem. 1983, 36, 627-632.
14. Banfield, J.E.; Black, D.S.C.; Johns, S.R.; Willing, R.I. Constituents of Endiandra species. IV. 2-(8'-[(E,E)-5"-phenylpenta-2",4"-dien- 1"-yl]bicyclo[4.2.0]octa-2',4'-dien-7'-yl)acetic acid, a biogenetically predicted metabolite of Endiandra introrsa (Lauraceae) and its structure determination by means of 1D and 2D NMR spectroscopy. Aust. J. Chem. 1982, 35, 2247-2256.
15. Nicolaou, K.C.; Petasis, N.A.; Zipkin, R.E. The endiandric acid cascade. Electrocyclizations in organic synthesis. 4. Biomimetic approach to endiandric acids A-G. Total synthesis and thermal studies. J. Am. Chem. Soc. 1982, 104, 5560-5562.
16. Nicolaou, K.C.; Zipkin, R.E.; Petasis, N.A. The endiandric acid cascade. Electrocyclizations in organic synthesis. 3. "Biomimetic" approach to endiandric acids A-G. Synthesis of precursors. J. Am. Chem. Soc. 1982, 104, 5558-5560.
17. Nicolaou, K.C.; Petasis, N.A. Strategies and Tactics in Organic Synthesis; Lindberg, T., Ed.; Academic Press: San Diego, CA, USA, 1984; Volume 1, pp. 155-173.
18. Chouna, J.R.; Nkeng-Efouet, P.A.; Lenta, B.N.; Devkota, K.P.; Neumann, B.; Stammler, H.-G.; Kimbu, S.F.; Sewald, N. Antibacterial endiandric acid derivatives from Beilschmiedia anacardioides. Phytochemistry 2009, 70, 684-688.
19. Chouna, J.R.; Nkeng-Efouet, P.A.; Lenta, B.N.; Wansi, J.D.; Kimbu, S.F.; Sewald, N. Endiandric acid derivatives from the stem bark of Beilschmiedia anacardioides. Phytochem. Lett. 2010, 3, 13-16.
20. Talontsi, F.M.; Lamshöft, M.; Bauer, J.O.; Razakarivony, A.A.; Andriamihaja, B.; Strohmann, C.; Spiteller, M. Antibacterial and antiplasmodial constituents of Beilschmiedia cryptocaryoides. J. Nat. Prod. 2013, 76, 97-102.
21. Yang, P.-S.; Cheng, M.-J.; Peng, C.-F.; Chen, J.-J.; Chen, I.-S. Endiandric acid analogues from the roots of Beilschmiedia erythrophloia. J. Nat. Prod. 2009, 72, 53-58.
22. Huang, Y.-T.; Chang, H.-S.; Wang, G.-J.; Cheng, M.-J.; Chen, C.-H.; Yang, Y.-J.; Chen, I.-S. Anti-inflammatory endiandric acid analogues from the roots of Beilschmiedia tsangii. J. Nat. Prod. 2011, 74, 1875-1880.
23. Williams, R.B.; Martin, S.M.; Hu, J.-F.; Norman, V.L.; Goering, M.G.; Loss, S.; O'Neil-Johnson, M.; Eldridge, G.R.; Starks, C.M. Cytotoxic and antibacterial beilschmiedic acids from a gabonese species of Beilschmiedia. J. Nat. Prod. 2012, 75, 1319-1325.
24. Gravel. E.; Poupon, E. Biogenesis and biomimetic chemistry: Can complex natural products be assembled spontaneously? Eur. J. Org. Chem. 2008, 1, 27-42.
25. Huang, Y.-T.; Chang, H.-S.; Wang, G.-J.; Lin, C.-H.; Chen, I.-S. Secondary metabolites from the roots of Beilschmiedia tsangii and their anti-inflammatory activities. Int. J. Mol. Sci. 2012, 13, 16430-16443.
26. Qian, J.; Voorbach, M.J.; Huth, J.R.; Coen, M.L.; Zhang, H.; Ng, S.-C.; Comess, K.M.; Petros, A.M.; Rosenberg, S.H.; Warrior, U.; et al. Discovery of novel inhibitors of Bcl-xL using multiple high-throughput screening platforms. Anal. Biochem. 2004, 328, 131-138.
27. Bruker (2000). SAINT and SMART; Bruker AXS Inc.: Madison, WI, USA, 2000.
28. Sheldrick, G.M. SHELXTL. Version 5.1 Bruker AXS; University of Göttingen: Göttingen, Germany, 2008.
29. Nikolovska-Coleska, Z.; Wang, R.; Fang, X.; Pan, H.; Tomita, Y.; Li, P.; Roller, P.P.; Krajewski, K.; Saito, N.G.; Stuckey, J.A.; et al. Development and optimization of a binding assay for the XIAP BIR3 domain using fluorescence polarization. Anal. Biochem. 2004, 332, 261-273.
30. Cheng, Y.; Prusoff, W.H. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
31. Zhang, J.H.; Chung, T.D.; Oldenburg, K.R. A simple statistical parameter for use in evaluation and validation of high throughput screening assays. J. Biomol. Screen. 1999, 4, 67-73.
32. Riss, T.L.; Moravec, R.A. Comparison of MTT, XTT, and a novel tetrazolium compound MTS for in vitro proliferation and chemosensitivity assays. Mol. Biol. Cell 1992, 3, 184a-188a.