Guaianolides in apiaceae: perspectives on pharmacology and biosynthesis
Tóm tắt
Từ khóa
Tài liệu tham khảo
Ahmed S (1998) Isolation and Structural elucidation of chemical constituents from Fumaria indica, Ferula oopoda and Withania somnifera. Ph.D. Thesis, University of Karachi
Andrews SP, Ball M, Wierschem F, Cleator E, Oliver S, Hogenauer K, Simic O, Antonello A, Hunger U, Smith MD, Ley SV (2007) Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition. Chem Eur J 13(20):5688–5712. doi: 10.1002/chem.200700302
Appendino G, Valle MG, Caniato R, Cappelletti EM (1986) Sesquiterpene Lactones from Laserpitium garganicum. Phytochem 25(7):1747–1749. doi: 10.1016/S0031-9422(00)81252-2
Azarken R, Guerra FM, Moreno-Dorado FJ, Jorge ZD, Massanet GM (2008) Substituent effects in the transannular cyclizations of germacranes. Synthesis of 6-epi-costunolide and five natural steiractinolides. Tetrahedron 64:10896–10905. doi: 10.1016/j.tet.2008.09.017
Barton Sir D, Nakanishi K, Meth-Cohn O (1999) Comprehensive natural products chemistry. Elsevier Science Ltd, London
Beekman AC, Woerdenbag WV, Pras N, Konings AWT, Wikström HV, Schmidt TJ (1997) Structure-cytotoxicity relationship of some helenanolide-type sesquiterpene lactones. J Nat Prod 60:252–257. doi: 10.1021/np960517h
Berenbaum MR (2001) Chemical mediation of coevolution: phylogenetic evidence for apiaceae and associates. Ann Mo Bot Gard 88:45–59. doi: 10.2307/2666131
Berg JM, Tymoczkom JL, Stryer L (2007) Biochemistry. W.H. Freeman and company, New York
Bertea CM, Voster A, Verstappen FWA, Maffei M, Beekwilder J, Bouwmeester HJ (2006) Isoprenoid biosynthesis in Artemisia annua: Cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library. Arch Biochem Biophys 448(1–2):3–12. doi: 10.1016/j.abb.2006.02.026
Bick JA, Lange BM (2003) Metabolic cross talk between cytosolic and plastidial pathways of isoprenoid biosynthesis: unidirectional transport of intermediates across the chloroplast envelope membrane. Arch Biochem Biophys 415(2):146–154. doi: 10.1016/S0003-9861(03)00233-9
Bohlmann J, Meyer-Gauen G, Croteau R (1998) Plant terpenoid synthases: molecular biology and phylogenetic analysis. Proc Natl Acad Sci USA 95(8):4126–4133. doi: 10.1073/pnas.95.8.4126
Chandran SS, Nan A, Rosen DM, Ghandehari H, Denmeade SR (2007) A prostate-specific antigen activated N-(2-hydroxypropyl) methacrylamide copolymer prodrug as dual-targeted therapy for prostate cancer. Mol Cancer Ther 6(11):2928–2937. doi: 10.1158/1535-7163.MCT-07-0392
Chang MCY, Keasling JD (2006) Production of isoprenoid pharmaceuticals by engineered microbes. Nat Chem Biol 2(12):674–681. doi: 10.1038/nchembio836
Choi JH, Ha J, Park JH, Lee JY, Lee YS, Park HJ, Choi JW, Masuda Y, Nakaya K, Lee KT (2002) Costunolide triggers apoptosis in human leukemia U937 cells by depleting intracellular thiols. Jpn J Cancer Res 93:1327–1333
Christensen SB, Norup E, Rasmussen U (1984a) Chemistry and structure-activity relationship of the histamine secretagogue thapsigargin and related compounds. In: Krogsgaard-Larsen P, Christensen SB, Kofod H (eds) Natural products and drug development. Munksgaard, Copenhagen
Christensen SB, Norup E, Rasmussen U, Madsen JO (1984b) Structure of histamine releasing guaianolides from Thapsia species. Phytochem 23(8):1659–1663. doi: 10.1016/S0031-9422(00)83463-9
Christensen SB, Andersen A, Smitt UW (1997) Sesquiterpenoids from Thapsia species and medicinal chemistry of the thapsigargins. Fortschr Chem Org Naturst 71:129–167
Christensen SB, Andersen A, Kromann H, Treiman M, Tombal B, Denmeade S, Isaacs JT (1999) Thapsigargin analogues for targeting programmed death of androgen-independent prostate cancer cells. Bioorg Med Chem 7(7):1273–1280. doi: 10.1016/S0968-0896(99)00074-7
Christiansen AV, Paalum H, Andersen SM, Pujadas A, Smitt UW (1997) Quantitative determination of thapsigargins in roots and fruits from Thapsia gymnesica. Planta Med 63:565–567. doi: 10.1055/s-2006-957769
De Kraker JW, Franssen MCR, de Groot A, Konig WA, Bouwmeester HJ (1998) (+)-Germacrene A biosynthesis—The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory. Plant Physiol 117(4):1381–1392. doi: 10.1104/pp.117.4.1381
De Kraker JW, Franssen MCR, Dalm MCF, de Groot A, Bouwmeester HJ (2001) Biosynthesis of germacrene A carboxylic acid in chicory roots. Demonstration of a cytochrome P450 (+)-germacrene A hydroxylase and NADP(+)-dependent sesquiterpenoid dehydrogenase(s) involved in sesquiterpene lactone biosynthesis. Plant Physiol 125(4):1930–1940. doi: 10.1104/pp.125.4.1930
De Kraker JW, Franssen MCR, Joerink M, de Groot A, Bouwmeester HJ (2002) Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome P450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory. Plant Physiol 129(1):257–268. doi: 10.1104/pp.010957
Denmeade SR, Isaacs JT (2005) The SERCA pump as a therapeutic target: making a “smart bomb” for prostate cancer. Cancer Biol Ther 4(1):14–22
Denmeade SR, Lin XS, Isaacs JT (1996) Role of programmed (apoptotic) cell death during the progression and therapy for prostate cancer. Prostate 28(4):251–265. doi: 10.1002/(SICI)1097-0045(199604)28:4<251::AID-PROS6>3.0.CO;2-G
Dewick PM (1995) The Biosynthesis of C-5-C-20 Terpenoid Compounds. Nat Prod Rep 12:507–534. doi: 10.1039/np9951200507
Djermanovic M, Stefanovic M, Djermanovic V, Milovanovic M (1995) Structure elucidation of the sesquiterpene lactones from plant species Laserpitium latifolium L. J Herbs Spices Med Plants 3(2):3–10. doi: 10.1300/J044v03n02_02
Falsone G, Haddad H, Wendisch D (1986) Sesquiterpene lactone triesters with unusual structures from Thapsia garganica L (Umbelliferae). Arch Pharm (Weinheim) 319(4):372–379. doi: 10.1002/ardp.19863190414
GenSpera (2009) Technology information, GenSpera, Inc, San Antonio, Texas, USA. http://www.genspera.com . Cited 23 Feb 2009
Ghisalberti EL (1994) The Daucane (Carotane) class of sesquiterpenes. Phytochem 37(3):597–623. doi: 10.1016/S0031-9422(00)90327-3
Hampel D, Mosandl A, Wust M (2005) Biosynthesis of mono- and sesquiterpenes in carrot roots and leaves (Daucus carota L.): metabolic cross talk of cytosolic mevalonate and plastidial methylerythritol phosphate pathways. Phytochem 66(3):305–311. doi: 10.1016/j.phytochem.2004.12.010
Hemmerlin A, Hoeffler JF, Meyer O, Tritsch D, Kagan IA, Grosdemange-Billiard C, Rohmer M, Bach TJ (2003) Cross-talk between the cytosolic mevalonate and the plastidial methylerythritol phosphate pathways in tobacco bright yellow-2 cells. J Biol Chem 278(29):26666–26676. doi: 10.1074/jbc.M302526200
Holub M, Budesinsky M (1986) Review article number 20. Sesquiterpene lactones of the umbelliferae. Phytochem 25(9):2015–2026. doi: 10.1016/0031-9422(86)80060-7
Holub M, Samek Z (1973) On Terpenes. 222. Structure of archangelolide, a sesquiterpenic lactone from Laserpitium archangelica wulf. Collect Czech Chem Commun 38(3):731–738
Holub M, Degroote R, Herout V, Sorm F (1968) Plant Substances. 28. Oxygen-containing components of light petroleum extract of Laser trilobum (L) Borkh root structure of laserine. Collect Czech Chem Commun 33(9):2911
Holub M, Herout V, Samek Z, Motl O (1972) Terpenes. 214. Structure of 2 sesquiterpenic lactones, isomontanolide and acetylisomontanolide from Laserpitium siler L. Collect Czech Chem Commun 37(4):1186
Holub M, Samek Z, Vasickova S, Masojidkova M (1978a) Terpenes. 251. 11-hydroxy-1-beta-H, 5-beta-H, 6-alpha-, 7-alpha-H-guaian-6, 12-olides—relative and absolute-configuration of sesquiterpenic lactones montanolide, isomontanolide, acetylisomontanolide and related substances. Collect Czech Chem Commun 43(9):2444–2470
Holub M, Motl O, Samek Z (1978b) Terpenes. 252. Structure and relative and absolute-configurations of sesquiterpenic lactones gradolide and polhovolide from Laserpitium Siler L. Collect Czech Chem Commun 43(9):2471–2477
Holub M, Toman J, Herout V (1987) The phylogenetic-relationships of the asteraceae and apiaceae based on phytochemical characters. Biochem Syst Ecol 15(3):321–326. doi: 10.1016/0305-1978(87)90006-8
Iranshahi M, Hosseini ST, Shahverdi AR, Molazade K, Khan SS, Ahmad VU (2008) Diversolides A-G, guaianolides from the roots of Ferula diversivittata. Phytochem 69:2753–2757 Observe that retraction of claims on diversolides A, C–G are in the process of being printed
Jakobsen CM, Denmeade SR, Isaacs JT, Gady A, Olsen CE, Christensen SB (2001) Design, synthesis, and pharmacological evaluation of thapsigargin analogues for targeting apoptosis to prostatic cancer cells. J Med Chem 44(26):4696–4703. doi: 10.1021/jm010985a
Kabilov MH, Saidkhodzhaev AI, Malikov VM, Melibaev S (1994) Sesquiterpene lactones of Ferula koso-poljanskyi. Chem Nat Compd 30(4):523. doi: 10.1007/BF00630416
Lee SH, Lee MY, Kang HM, Han DC, Son KH, Yang DC, Sung ND, Lee CW, Kim HM, Kwon BM (2003) Anti-tumor activity of the farnesyl-protein transferase inhibitors arteminolides, isolated from artemisa. Bioorg Med Chem 11:4545–4549. doi: 10.1016/j.bmc.2003.08.008
Li YS, Chen JJ, Zhou H, Luo SD, Wang HY, Zhu DY (2003) Two new guaianolides and a new daucene derivative from Sinodielsia yunnanensis. Planta Med 69(10):962–964. doi: 10.1055/s-2003-45111
Liu HZ, Jensen KG, Tran LM, Chen M, Zhai L, Olsen CE, Sohoel H, Denmeade SR, Isaacs JT, Christensen SB (2006) Cytotoxic phenylpropanoids and an additional thapsigargin analogue isolated from Thapsia garganica. Phytochem 67(24):2651–2658. doi: 10.1016/j.phytochem.2006.10.005
Milosavljevic S, Bulatovic V, Stefanovic M (1999) Sesquiterpene lactones from the Yugoslavian wild growing plant families asteraceae and apiaceae. J Serb Chem Soc 64(7–8):397–442
Muckensturm B, Diyani F, Reduron J-P (1995) Grilactone and other terpenoids from Anthriscus nitida. Biochem Syst Ecol 23(7/8):875–876. doi: 10.1016/0305-1978(95)00058-5
Muckensturm B, Diyani F, Nouën DL, Fkih-Tetouani S, Reduron J-P (1997) Ammolactone, a guaianolide from a medicinal plant, Ammodaucus leucotrichus. Phytochem 44(5):907–910. doi: 10.1016/S0031-9422(96)00621-8
Nawrot J, Smitalova Z, Holub M (1983) Terpenes. 273. Deterrent activity of sesquiterpene lactones from the umbelliferae against storage pests. Biochem Syst Ecol 11(3):243–245. doi: 10.1016/0305-1978(83)90061-3
Norup E, Smitt UW, Christensen SB (1986) The potencies of Thapsigargin and analogs as activators of rat peritoneal mast-cells. Planta Med 52(4):251–255. doi: 10.1055/s-2007-969144
Nurmukhamedova MR, Kasymov SZ, Melibaev S (1982) Grilactone from Ferula-Penninervis. Him Prir Soedin 2:261
Nurmukhamedova MR, Kasymov SZ, Sidyakin GP (1983) Ferolid—A new lactone from Ferula-Penninervis. Him Prir Soedin 4:533
Nurmukhamedova MR, Kasymov S, Abdullaev ND, Sidyakin GP (1985) Structure of fegolide. Him Prir Soedin 3:335–337
Okada K, Kasahara H, Yamaguchi S, Kawaide H, Kamiya Y, Nojiri H, Yamane H (2008) Genetic evidence for the role of isopentenyl diphosphate isomerases in the mevalonate pathway and plant development in arabidopsis. Plant Cell Physiol 49(4):604–616. doi: 10.1093/pcp/pcn032
Piet DP, Schrijvers R, Franssen MCR, de Groot A (1995) Biotransformation of Germacrane epoxides by Cichorium intybus. Tetrahedron 51(22):6303–6314. doi: 10.1016/0040-4020(95)00272-A
Pinar M, Rico M, Rodriguez B (1982) Desangeloylshairidin, a sesquiterpene lactone from Guillonea scabra. Phytochem 21:1802–1804
Pinar M, Rodriguez B, Rico M, Perales A, Fayos J (1983) Guillonein, An epoxyguaianolide from Guillonea scabra, X-Ray structure determination. Phytochem 22:987–990. doi: 10.1016/0031-9422(83)85037-7
Rasmussen U, Christensen SB, Sandberg F (1978) Thapsigargine and thapsigargicine, two new histamine liberators from Thapsia garganica L. Acta Pharm Suec 15(2):133–140
Rasmussen U, Christensen SB, Sandberg F (1981) Phytochemistry of the genus Thapsia. Planta Med 43:336–341. doi: 10.1055/s-2007-971521
Ro DK, Paradise EM, Ouellet M, Fisher KJ, Newman KL, Ndungu JM, Ho KA, Eachus RA, Ham TS, Kirby J, Chang MCY, Withers ST, Shiba Y, Sarpong R, Keasling JD (2006) Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 440(7086):940–943. doi: 10.1038/nature04640
Rohdich F, Hecht S, Gartner K, Adam P, Krieger C, Amslinger S, Arigoni D, Bacher A, Eisenreich W (2002) Studies on the nonmevalonate terpene biosynthetic pathway: metabolic role of IspH (LytB) protein. Proc Natl Acad Sci USA 99(3):1158–1163. doi: 10.1073/pnas.032658999
Rohmer M, Knani M, Simonin P, Sutter B, Sahm H (1993) Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem J 295:517–524
Rontein D, Onillon S, Herbette G, Lesot A, Werck-Reichhart D, Sallaud C, Tissier A (2008) CYP725A4 from yew catalyzes complex structural rearrangement of taxa-4(5), 11(12)-diene into the cyclic ether 5(12)-oxa-3(11)-cyclotaxane. J Biol Chem 283(10):6067–6075. doi: 10.1074/jbc.M708950200
Rubal JJ, Guerra FM, Moreno-Dorado FJ, Jorge ZD, Massanet GM, Sohoel H, Smitt UW, Frydenvang K, Christensen SB, Nielsen C, Erikson M (2006) Sesquiterpenes from Thapsia nitida var. meridionalis and Thapsia nitida var. nitida. J Nat Prod 69(11):1566–1571. doi: 10.1021/np0603065
Rubal JJ, Guerra FM, Moreno-Dorado FJ, Akssira M, Mellouki F, Pujadas AJ, Jorge ZD, Massanet GM (2007a) Sulfur-containing sesquiterpenes from Thapsia villosa. Tetrahedron 60:159–164. doi: 10.1016/j.tet.2003.10.079
Rubal JJ, Moreno-Dorado FJ, Guerra FM, Jorge ZD, Saouf A, Akssira M, Mellouki F, Romero-Garrido R, Massanet GM (2007b) A pyran-2-one and four meroterpenoids from Thapsia transtagana and their implication in the biosynthesis of transtaganolides. Phytochem 68:2480–2486. doi: 10.1016/j.phytochem.2007.06.023
Rüngeler P, Castro V, Mora G, Gören N, Vichnewski W, Pahl HL, Merfort I, Schmidt TJ (1999) Inhibition of transcription factor NF-κB by sesquiterpene lactones: a proposed molecular mechanism of action. Bioorg Med Chem 7:2343–2352. doi: 10.1016/S0968-0896(99)00195-9
Rychlewska U, Hodgson DJ, Holub M, Budesinsky M, Smitalova Z (1985) On Terpenes 288 The Structure of 2-Oxo-8-alpha-angeloyloxy-11-alpha-acetoxy-5-beta-H,6-alpha-H,7-alpha-H-guai-1(10),3-dien-6,12-olide, a sesquiterpene lactone from Laserpitium prutenicum L. Revision of the stereostructures of native 2-oxoguai-1(10),3-dien-6,12-olides from the species of the Umbelliferae family. Collect Czech Chem Commun 50(11):2607–2624
Sagitdinova GV, Saidkhodzhaev AI, Malikov VM, Pimenov MG, Melibeav S (1990) Sesquiterpene lactones of Ferula clematidifolia and Ligularia alpigena. Him Prir Soedin 4:553–555
Schall A, Reiser O (2008) Synthesis of biologically active guaianolides with a trans-annulated lactone moiety. Eur J Org Chem 2353–2364. doi: 10.1002/ejoc.200700880
Serkerov SV (1980) Stereochemistry of Guaianolides of Ferula oopoda. Him Prir Soedin 5:629–633
Serkerov SV, Rikhlevska U, Aleskerova AN, Mirbabaev NF (1991) New guanolide—Opofersin from Ferula Oopoda roots. Him Prir Soedin 3:318–319
Siedle B, García-Piñeres AJ, Murillo R, Schulte-Mönting J, Castro V, Rüngeler P, Klaas CA, Da Costa FB, Kisiel W, Merfort I (2004) Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NF-κB. J Med Chem 47:6042–6054. doi: 10.1021/jm049937r
Smitalova Z, Budesinsky M, Saman D, Vasickova S, Holub M (1984) On Terpenes. 279. Components of the extract from the underground parts of Laserpitium siler L of Slovenian origin, mainly sesquiterpenic lactones. Collect Czech Chem Commun 49(4):852–870
Smitalova Z, Budesinsky M, Saman D, Holub M (1986) On Terpenes. 291. Minor sesquiterpenic lactones of Laser trilobum (L) Borkh species. Collect Czech Chem Commun 51(6):1323–1339
Smitt UW, Cornett C, Andersen A, Christensen SB, Avato P (1990) New proazulene guaianolides from Thapsia villosa. J Nat Prod 53(6):1479–1484. doi: 10.1021/np50072a012
Smitt UW, Jager AK, Adsersen A, Gudiksen L (1995) Comparative studies in phytochemistry and fruit anatomy of Thapsia garganica and T. transtagana, Apiaceae (Umbelliferae). Bot J Linn Soc 117(4):281–292. doi: 10.1006/bojl.1995.0019
Søhoel H, Jensen AM, Moller JV, Nissen P, Denmeade SR, Isaacs JT, Olsen CE, Christensen SB (2006) Natural products as starting materials for development of second-generation SERCA inhibitors targeted towards prostate cancer cells. Bioorg Med Chem 14(8):2810–2815. doi: 10.1016/j.bmc.2005.12.001
Song Q, Gomezbarrios ML, Hopper EL, Hjortso MA, Fischer NH (1995) Biosynthetic-studies of lactucin derivatives in hairy root cultures of Lactuca floridana. Phytochem 40(6):1659–1665. doi: 10.1016/0031-9422(95)00478-P
Steele CL, Crock J, Bohlmann J, Croteau R (1998) Sesquiterpene synthases from grand fir (Abies grandis)—Comparison of constitutive and wound-induced activities, and cDNA isolation, characterization and bacterial expression of delta-selinene synthase and gamma-humulene synthase. J Biol Chem 273(4):2078–2089. doi: 10.1074/jbc.273.4.2078
Suzuki K, Okasaka M, Kashiwada Y, Takaishi Y, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O, Sekiya M, Ikeshiro Y (2007) Sesquiterpene lactones from the roots of Ferula varia and their cytotoxic activity. J Nat Prod 70(12):1915–1918. doi: 10.1021/np0703996
Teoh KH, Polichuk DR, Reed DW, Nowak G, Covello PS (2006) Artemisia annua L (Asteraceae) trichome-specific cDNAs reveal CYP71AV1, a cytochrome P450 with a key role in the biosynthesis of the antimalarial sesquiterpene lactone artemisinin. FEBS Lett 580(5):1411–1416. doi: 10.1016/j.febslet.2006.01.065
Toyoshima C, Nomura H (2002) Structural changes in the calcium pump accompanying the dissociation of calcium. Nature 418(6898):605–611. doi: 10.1038/nature00944
Wang NH, Taniguchi M, Tsuji D, Doi M, Ohishi H, Yoza K, Baba K (2003) Four guaianolides from Sinodielsia yunnanensis. Chem Pharm Bull (Tokyo) 51(1):68–70. doi: 10.1248/cpb.51.68
Wictome M, Holub M, East JM, Lee AG (1994) The importance of the hydroxyl moieties for inhibition of Ca2+-ATPases by trilobolide and 2, 5-di(tert-butyl)-1, 4-benzohydroquinone. Biochem Biophys Res Commun 199(2):916–921. doi: 10.1006/bbrc.1994.1316
Withers ST, Keasling JD (2007) Biosynthesis and engineering of isoprenoid small molecules. Appl Microbiol Biotechnol 73(5):980–990. doi: 10.1007/s00253-006-0593-1