Design, synthesis, in vitro cytotoxicity evaluation and structure–activity relationship of Goniothalamin analogs

Ahmad, F.B., W.A. Tukol, S. Omar, and A.M. Sharif. 1991. 5-Acetyl goniothalamin, a styryl dihydropyrone from Goniothalamus uvaroides. Phytochemistry 30(7): 2430–2431. Ali, A.M., M.M. Mckeen, M. Hamid, Q.B. Aun, Y. Zauyah, H.L.P. Azimahtol, and K. Kawazu. 1997. Cytotoxicity and electron microscopy of cell death induced by goniothalamin. Planta Medica 63(01): 81–83. Azimahtol Hawariah, L.P., M. Munawer, and L.B. Din. 1994. Anti-fertility effect of goniothalamin: A styrylpyrone isolated from Goniothalamus tapis miq. Asia Pacific journal of pharmacology 9(273–277): 273. Azimahtol Hawariah, L.P., and J. Stanslas. 1998. Antagonistic effects of styrylpyrone derivative (spd) on 7, 12, dimethylbenzanthracene-induced rat mammary tumors. In vivo 12(4): 403–410. Cao, S.-G., X.-H. Wu, K.-Y. Sim, B.K.H. Tan, J.T. Pereira, and S.-H. Goh. 1998. Styryl-lactone derivatives and alkaloids from Goniothalamus borneensis (Annonaceae). Tetrahedron 54(10): 2143–2148. Cavalheiro, A.J., and M. Yoshida. 2000. 6-[ω-Arylalkenyl]-5,6-dihydro-α-pyrones from Cryptocarya moschata (Lauraceae). Phytochemistry 53(7): 811–819. Chan, K.M., N.F. Rajab, M.H.A. Ishak, A.M. Ali, K. Yusoff, L.B. Din, and S.H. Inayat-Hussain. 2006. Goniothalamin induces apoptosis in vascular smooth muscle cells. Chemico-Biological Interactions 159(2): 129–140. Chen, W.-Y., C.-C. Wu, Y.-H. Lan, F.-R. Chang, C.-M. Teng, and Y.-C. Wu. 2005. Goniothalamin induces cell cycle-specific apoptosis by modulating the redox status in MDA-MB-231 cells. European Journal of Pharmacology 522(1–3): 20–29. Chidambaram, N., K. Satyanarayana, and S. Chandrasekaran. 1989. A general approach to the synthesis of 5,6-dihydro-2(2H)pyranones; simple synthesis of α-pyrone, (±)-argentilactone and (±)-goniothalamin. Tetrahedron Letters 30(18): 2429–2432. Chien, A.L.T., and L.P. Azimahtol Hawariah. 2003. Styrylpyrone derivative induces apoptosis through the up-regulation of bax in the human breast cancer cell line MCF-7. Journal of Biochemistry and Molecular Biology 36: 269–274. De Fátima, Â., L.K. Kohn, M.A. Antônio, J.E. De Carvalho, and R.A. Pilli. 2005. (R)-Goniothalamin: Total syntheses and cytotoxic activity against cancer cell lines. Bioorganic & Medicinal Chemistry 13(8): 2927–2933. De Fátima, Â., L.K. Kohn, J.E. De Carvalho, and R.A. Pilli. 2006a. Cytotoxic activity of (S)-goniothalamin and analogues against human cancer cells. Bioorganic & Medicinal Chemistry 14(3): 622–631. De Fátima, Â., L.V. Modolo, L.S. Conegero, R.A. Pilli, C.V. Ferreira, L.K. Kohn, and J.E. De Carvalho. 2006b. Styryl lactones and their derivatives: Biological activities, mechanisms of action and potential leads for drug design. Current Medicinal Chemistry 13(28): 3371–3384. De Fátima, Â., and R.A. Pilli. 2003a. Enantioselective approach to the asymmetric synthesis of (6R)-hydroxymethyl-5,6-dihydro-2H-pyran-2-one. A formal synthesis of (R)-argentilactone and total synthesis of (R)-goniothalamin (RR-820CP). Arkivoc 2003(10): 118–126. De Fátima, Â., and R.A. Pilli. 2003b. Total syntheses of (R)-argentilactone and (R)-goniothalamin via catalytic enantioselective allylation of aldehydes. Tetrahedron Letters 44(48): 8721–8724. De Fátima, Â., W.F. Zambuzzi, L.V. Modolo, C.A.B. Tarsitano, F.R. Gadelha, S. Hyslop, J.E.D. Carvalho, I. Salgado, C.V. Ferreira, and R.A. Pilli. 2008. Cytotoxicity of goniothalamin enantiomers in renal cancer cells: Involvement of nitric oxide, apoptosis and autophagy. Chemico-Biological Interactions 176(2–3): 143–150. Drewes, S.E., M.M. Horn, and R.S. Shaw. 1995. Α-pyrones and their derivatives from two cryptocarya species. Phytochemistry 40(1): 321–323. Du, H., J. Long, J. Hu, X. Li, and K. Ding. 2002. 3,3′-Br2-BINOL-Zn complex: A highly efficient catalyst for the enantioselective hetero-Diels–Alder reaction. Organic Letters 4(24): 4349–4352. El-Sharkawy, S., Z. Yusuf, L.P. Azimahtol Hawariah, and A.M. Ali. 1996. Metabolism of goniothalamin in animal and microbial system. Bollettino Chimico Farmaceutico 135(1): 35–40. El-Zayat, A.A.E., N.R. Ferrigni, T.G. Mccloud, A.T. Mckenzie, S.R. Byrn, J.M. Cassady, C.-J. Chang, and J.L. Mclaughlin. 1985. Goniothalenol: A novel, bioactive, tetrahydrofurano-2-pyrone from Goniothalamus giganteus (Annonaceae). Tetrahedron Letters 26(8): 955–956. Fournier, L., P. Kocienski, and J.-M. Pons. 2004. The β-lactone route to α,β-unsaturated δ-lactones. Total syntheses of (±)-goniothalamin and (−)-massoialactone. Tetrahedron 60(7): 1659–1663. Gillard, F., D. Heissler, and J.-J. Riehl. 1988. Synthesis of the 5,6-dihydro-2-pyrone moiety of (+)-anamarin. Journal of the Chemical Society, Perkin Transactions 10(8): 2291–2295. Goh, S.H., G.C.L. Ee, C.H. Chuah, and C. Wei. 1995. Styrylpyrone derivatives from Goniothalamus dolichocarpus. Australian Journal of Chemistry 48(2): 199–205. Grubbs, R.H. 2004. Olefin metathesis. Tetrahedron 60(34): 7117–7140. Gruttadauria, M., P. Lo Meo, and R. Noto. 2004. Short and efficient chemoenzymatic synthesis of goniothalamin. Tetrahedron Letters 45(1): 83–85. Harsh, P., and G.A. O’doherty. 2009. De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations. Tetrahedron 65(26): 5051–5055. Hasan, C.M., M.A. Hussain, M.Y. Mia, and M.A. Rashid. 1995. Goniothalamin from Goniothalamus sesquipedalis. Fitoterapia 4: 378–379. Hlubucek, J.R., and A.V. Robertson. 1967. (+)-(5S)-δ-Lactone of 5-hydroxy-7-phenylhepta-2,6-dienoic acid, a natural product from Cryptocarya caloneura (Scheff.) Kostermans. Australian Journal of Chemistry 20(10): 2199–2206. Inayat-Hussain, S.H., B.O. Annuar, L.B. Din, A.M. Ali, and D. Ross. 2003. Loss of mitochondrial transmembrane potential and caspase-9 activation during apoptosis induced by the novel styryl-lactone goniothalamin in HL-60 leukemia cells. Toxicology in Vitro 17(4): 433–439. Inayat-Hussain, S.H., K.M. Chan, N.F. Rajab, L.B. Din, S.C. Chow, A. Kizilors, F. Farzaneh, and G.T. Williams. 2010. Goniothalamin-induced oxidative stress, DNA damage and apoptosis via caspase-2 independent and Bcl-2 independent pathways in jurkat T-cells. Toxicology Letters 193(1): 108–114. Inayat-Hussain, S.H., A.B. Osman, L.B. Din, A.M. Ali, R.T. Snowden, M. Macfarlane, and K. Cain. 1999. Caspases-3 and -7 are activated in goniothalamin-induced apoptosis in human jurkat T-cells. FEBS Letters 456(3): 379–383. Inayat-Hussain, S.H., L.T. Wong, K.M. Chan, N.F. Rajab, L.B. Din, R. Harun, A. Kizilors, N. Saxena, M. Mourtada-Maarabouni, F. Farzaneh, and G.T. Williams. 2009. RACK-1 overexpression protects against goniothalamin-induced cell death. Toxicology Letters 191(2–3): 118–122. Jagtap, P.G., Z. Chen, K. Koppetsch, E. Piro, P. Fronce, G.J. Southan, and K.-N. Klotz. 2009. Synthesis of (R)-3,4-dihydro-2H-pyran-2-carboxaldehyde: Application to the synthesis of potent adenosine A2A and A3 receptor agonist. Tetrahedron Letters 50(22): 2693–2696. Jewers, K., J.B. Davis, J. Dougan, A.H. Manchanda, G. Blunden, A. Kyi, and S. Wetchapinan. 1972. Goniothalamin and its distribution in four goniothalamus species. Phytochemistry 11(6): 2025–2030. Kabir, K.E., A.R. Khan, and M.A. Mosaddik. 2003. Goniothalamin—a potent mosquito larvicide from Bryonopsis laciniosa L. Journal of Applied Entomology 127(2): 112–115. Lan, Y.-H., F.-R. Chang, J.-H. Yu, Y.-L. Yang, Y.-L. Chang, S.-J. Lee, and Y.-C. Wu. 2003. Cytotoxic styrylpyrones from Goniothalamus amuyon L. Journal of Natural Products 66(4): 487–490. Lee, A.T., L.P. Azimahtol Hawariah, H.L. Azimahtol, and A.N. Tan. 2003. Styrylpyrone derivative (SPD) induces apoptosis in a caspase-7-dependent manner in the human breast cancer cell line MCF-7. Cancer Cell International 3: 1–8. Leßmann, T., M.G. Leuenberger, S. Menninger, M. Lopez-Canet, O. Müller, S. Hümmer, J. Bormann, K. Korn, E. Fava, M. Zerial, Thomas U. Mayer, and H. Waldmann. 2007. Natural product-derived modulators of cell cycle progression and viral entry by enantioselective oxa Diels–Alder reactions on the solid phase. Chemistry & Biology 14(4): 443–451. Meenakshii, N., A. Lee, H.L.P. Azimahtol, and S. Hasidah. 2000. Increased levels of apoptosis correlate with p53 protein accumulation in response to styrylpyrone derivative (SPD) treatment of the “Huggins Tumor”. Malaysian Applied Biology 29(1 & 2): 121–126. Mereyala, H.B., and M. Joe. 2001. Cytotoxic activity of styryl lactones and their derivatives. Current Medicinal Chemistry—Anti-Cancer Agents 1(3): 293–300. Mondon, M., and J.-P. Gesson. 2006. Asymmetric synthesis of styryl-lactones. Current Organic Synthesis 3(1): 41–75. Mosaddik, M.A., M. Ekramul Haque, and M. Abdur Rashid. 2000. Goniothalamin from Bryonopsis laciniosa linn (cucurbiataceae). Biochemical Systematics and Ecology 28(10): 1039–1040. Mosaddik, M.A., and M.E. Haque. 2003. Cytotoxicity and antimicrobial activity of goniothalamin isolated from Bryonopsis laciniosa. Phytotherapy Research 17(10): 1155–1157. Mu, Q., W.D. Tang, R.Y. Liu, C.M. Li, L.G. Lou, H.D. Sun, and C.Q. Hu. 2003. Constituents from the stems of Goniothalamus griffithii. Planta Medica 69(09): 826–830. O’connor, B., and G. Just. 1986. Syntheses of argentilactone 11 and goniothalamin 15. Tetrahedron Letters 27(43): 5201–5202. Pospíšil, J., and I.E. Markó. 2006. Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: First application of the sulfoxide-modified Julia olefination in total synthesis. Tetrahedron Letters 47(33): 5933–5937. Quitschalle, M., M. Christmann, U. Bhatt, and M. Kalesse. 2001. Synthesis of unsaturated lactone moieties by asymmetric hetero Diels–Alder reactions with binaphthol–titanium complexes. Tetrahedron Letters 42(7): 1263–1265. Rajab, N.F., Z.A. Hamid, H. Hassan, A.M. Ali, L.B. Din, and S.H. Inayat-Hussain. 2005. Evaluation of the cytotoxic and genotoxic effects of goniothalamin in leukemic cell lines. Environmental Mutagen Research 27(3): 161–164. Ram Reddy, M.V., H.C. Brown, and P.V. Ramachandran. 2001. Asymmetric allylboration for the synthesis of β-hydroxy-δ-lactone unit of statin drug analogs. Journal of Organometallic Chemistry 624(1–2): 239–243. Ramachandran, P.V., M.V.R. Reddy, and H.C. Brown. 2000. Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration–esterification ring-closing metathesis reactions. Tetrahedron Letters 41(5): 583–586. RodríGuez, J.G., R. Martín-Villamil, and A. Lafuente. 2003. Π-Extended conjugate phenylacetylenes Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge–transfer complexes. Tetrahedron 59(7): 1021–1032. Sabitha, G., K. Sudhakar, and J.S. Yadav. 2006. Application of the cosford cross-coupling protocol for the stereoselective synthesis of (R)-(+)-goniothalamin, (R)-(+)-kavain and (S)-(+)-7,8-dihydrokavain. Tetrahedron Letters 47(48): 8599–8602. Sam, T.W., C. Sew-Yeu, S. Matsjeh, E.K. Gan, D. Razak, and A.L. Mohamed. 1987. Goniothalamin oxide: An embryotoxic compound from Goniothalamus macrophyllus (Annonaceae). Tetrahedron Letters 28(22): 2541–2544. Schaus, S.E., J. Brånalt, and E.N. Jacobsen. 1998. Asymmetric hetero-Diels–Alder reactions catalyzed by chiral (salen)chromium(III) complexes. The Journal of Organic Chemistry 63(2): 403–405. Schmidt, B. 2004. Ruthenium-catalyzed olefin metathesis double-bond isomerization sequence. The Journal of Organic Chemistry 69(22): 7672–7687. Sun, B., J. Hoshino, K. Jermihov, L. Marler, J.M. Pezzuto, A.D. Mesecar, and M. Cushman. 2010. Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer. Bioorganic & Medicinal Chemistry 18(14): 5352–5366. Sundby, E., L. Perk, T. Anthonsen, A. Jørgen Aasen, and T. Vidar Hansen. 2004. Synthesis of (+)-goniothalamin and its enantiomer by combination of lipase catalyzed resolution and alkene metathesis. Tetrahedron 60(3): 521–524. Tanaka, S., S. Yoichi, L. Ao, M. Matumoto, K. Morimoto, N. Akimoto, G. Honda, M. Tabata, T. Oshima, T. Masuda, M. Zaini Bin Asmawi, Z. Ismail, S.M. Yusof, L.B. Din, and I.M. Said. 2001. Potential immunosuppressive and antiinflammatory activities of Malaysian medicinal plants characterized by reduced cell surface expression of cell adhesion molecules. Phytotherapy Research 15(8): 681–686. Teoh, P.L., and L.P. Azimahtol Hawariah. 1999. Effects of styrylpyrne derivative (SPD) on expression of Bcl-2 and box genes in human ovarian carcinoma cell line, Caov-3. Malaysian Applied Biology 28(1 & 2): 107–111. Wyatt, P., A. Hudson, J. Charmant, A.G. Orpen, and H. Phetmung. 2006. Synthesis and chemistry of enantiomerically pure 10,11-dihydrodibenzo[b,f]thiepines. Organic & Biomolecular Chemistry 4(11): 2218–2232. Zauyah, Y., A.H. Lope Pihie, R.M. Noah, and J. Stanslas. 1997. Cytotoxicity of goniothalamin on hormone-dependent breast cancer cells. Malaysian Journal of Biochemistry and Molecular Biology 2: 29–32. Zhang, W., and M.L. Go. 2007. Quinone reductase induction activity of methoxylated analogues of resveratrol. European Journal of Medicinal Chemistry 42(6): 841–850. Zhou, F.S., W.D. Tang, Q. Mu, G.X. Yang, Y. Wang, G.L. Liang, and L.G. Lou. 2005. Semisynthesis and antitumor activities of new styryl-lactone derivatives. Chemical & Pharmaceutical Bulletin 53(11): 1387–1391. Zhou, Z.-L., and J.F.W. Keana. 1999. A practical synthesis of 4-(substituted-benzyl)piperidines and (±)-3-(substituted-benzyl)pyrrolidines via a wittig reaction. The Journal of Organic Chemistry 64(10): 3763–3766.