Triterpene-based plant defenses
Tóm tắt
Từ khóa
Tài liệu tham khảo
Abbot WS (1925) A method of computing the effectiveness of fan insecticide. J Econ Entomol 18:265–267
Abe M, Matsuda K (2000) Feeding deterrents from Momordica charantia leaves to cucurbitaceous feeding beetle species. Appl Entomol Zool 35:143–149
Almeida MMB, Arriaga AMC, Dos Santos AKL, Lemos TLG, Braz-Filho R, Curcino-Vieira IJ (2007) Occurrence and biological activity of quassinoids in the last decade. Quim Nova 30:935–951
Anaya AL, Mata R, González-Coloma A, Cruz-Ortega R, Guadaño A, Hernández-Bautista BE, Ríos G, Gómez-Pompa A (2003) Allelochemical potencial of Callicarpa acuminata (Verbenaceae). J Chem Ecol 29:2725–2740
Avilla J, Teixidó A, Velázquez C, Alvarenga N, Ferro E, Canela R (2000) Insecticidal activity of Maytenus species (Celastraceae). Nortriterpene quinone methides against codling moth, Cydia pomonella (L.) (Lepidoptera: Tortricidae). J Agric Food Chem 48:88–92
Baldovini N, Lavoine-Hanneguelle S, Ferrando G, Dusart G, Lizzani-Cuvelier L (2005) Necrodane monoterpenoids from Lavandula luisieri. Phytochemistry 66:1651–1655
Bloomquist JR (2001) GABA and glutamate receptors as biochemical sites for insecticide action. In: Ishaaya I (ed) Biochemical sites of insecticide action and resistance. Springer, New York, pp 17–41
Bloomquist JR (2003) Chloride channels as tools for developing selective insecticides. Arch Insect Biochem Physiol 54:145–156
Bloomquist JR, Boina DR, Chow E, Carlier PR, Reina M, González-Coloma A (2008) Mode of action of the plant-derived silphinenes on insect and mammalian GABA(A) receptor/chloride channel complex. Pest Biochem Physiol 91:17–23
Bretón J, Delgado-Martín J, Fraga BM, González AG (1969) Triterpenos de la Euphorbia paralias. Anales Real Soc Españ Fis Quim 65b:61–67
Butterworth JH, Morgan ED (1968) Isolation of a substance that suppresses feeding in locusts. Chem Commun, pp 23–24
Caballero-George C, Vanderheyden PML, Okamoto Y, Masaki T, Mbwambo Z, Apers S, Gupta MP, Pieters L, Vauquelin G, Vlietinck A (2004) Evaluation of bioactive saponins and triterpenoidal aglycons for their binding properties on human endothelin ETA and angiotensin AT1 receptors. Phytother Res 18:729–736
Castañeda P, García MR, Hernández E, Torres BA, Anaya AL, Mata R (1992) Effects of some compounds isolated from Calaeodendron mexicanum Standl (Euphorbiaceae) on seeds and phytopathogenic fungi. J Chem Ecol 18:1025–1037
Cespedes CL, Salazar JR, Martinez M, Aranda E (2005) Insect growth regulatory effects of some extracts and sterols from Myrtillocactus geometrizans (Cactaceae) against Spodoptera frugiperda and Tenebrio molitor. Phytochemistry 66:2481–2493
Chandravadana MV (1987) Identification of triterpenoid feeding deterrent of red pumpkin beetles (Aulacophora foveicollis) from Momordica charantia. J Chem Ecol 13:1689–1694
Chang CI, Kuo CC, Chang JY, Kuo YH (2004) Three new oleanane-type triterpenes from Ludwigia octovalvis with cytotoxic activity against two human cancer cell lines. J Nat Prod 67:91–93
D’Abrosca B, Florentino A, Monaco P, Pacifico S (2005) Radical-scavenging activities of new hydroxylated ursane triterpenes from cv. Annurca apples. Chem Biodiv 2:953–958
Danelli MGM, Soares DC, Abreu HS, Pecanha LMT, Saraiva EM (2009) Leishmanicidal effect of LLD-3, a nor-triterpene isolated from Lophanthera lactescens. Phytochemistry 70:608–614
De Andrade SF, Comunello E, Noldin VF, Delle Monache F, Cechinel Filho V, Niero R (2008) Antiulcerogenic activity of fractions and 3, 15-dioxo-21α-hydroxy-friedelane isolated from Maytenus robusta (Celastraceae). Arch Pharm Res 31:41–46
Duke SO, Oliva A (2004) Mode of action of phytotoxic terpenoids. In: Macías F, Galindo JCG, Molinillo JMG, Cutler HG (eds) Allelopathy, chemistry and mode of action of allelochemicals. CRC Press, Boca Raton, pp 201–216
Dzubak P, Hajduch M, Vydra D, Hustova A, Vasnika M, Biedermann D, Lenka M, Urban M, Sarek J (2006) Pharmacological activities of natural triterpenoids and their therapeutic implications. Nat Prod Rep 23:394–411
Eigenbrode SD, Espelie KE, Shelton AM (1991) Behaviour of neonate diamondback moth larvae Plutella xylostella (L.) on leaves and on extracted leaf waxes of resistant and susceptible cabbages. J Chem Ecol 17:1690–1691
Fraga BM, Reina M, Luis JG, Rodriguez ML (2003) Rhoiptelenol and rhoiptelenone, two pentacyclic triterpenes from Sideritis macrostachya Z. Natursforch 58c:621–625
Fu L, Zhang S, Li N, Wang J, Zhao M, Sakai J, Hasegawa T, Mitsui T, Kataoka T, Oka S, Kiuchi M, Hirose K, Ando M (2005) Three new triterpenes from Nerium oleander and biological activity of the isolated compounds. J Nat Prod 68:198–206
Golawska S (2007) Deterrence and toxicity of plants saponins for the pea aphid Acyrthosiphon pisum Harris. J Chem Ecol 33:1598–1606
González AG, Bretón JL, Fraga BM (1971) Constituents of Labiatae.1 Anagadiol, a new triterpenes from Salvia broussonetii Benth. Chem Commun, pp 567–568
González-Coloma A, Gutiérrez C, Cabrera R, Reina M (1997) Silphinene derivatives: their effects and modes of action on Colorado potato beetle. J Agric Food Chem 45:946–950
González-Coloma A, Guadaño A, Gutiérrez C, Cabrera R, de la Peña E, de la Fuente G, Reina M (1998) Antifeedant Delphinium diterpene alkaloids. Structure-activity relationships. J Agric Food Chem 46:286–290
González-Coloma A, Valencia F, Martín N, Hoffmann JJ, Hutter L, Marco JA, Reina M (2002a) Silphinene sesquiterpenes as model insect antifeedants. J Chem Ecol 28:117–129
González-Coloma A, Guadaño A, de Inés C, Martínez-Díaz R, Cortés D (2002b) Selective action of acetogenin mitochondrial complex I inhibitors. Z Naturforsch 57c:1028–1034
González-Coloma A, Martin-Benito D, Mohamed N, Garcia-Vallejo MC, Soria AC (2006) Antifeedant effects and chemical composition of essential oils from different populations of Lavandula luisieri L. Biochem Syst Ecol 34:609–616
Govindachari TR, Suresh G, Krishna-Kumari GN, Rajamannar T, Partho PD (1999) Nymania-3: A bioactive triterpenoid from Dysoxylun malabaricum. Fitoterapia 70:83–86
Gutiérrez C, Fereres A, Reina M, Cabrera R, González-Coloma A (1997) Behavioural and sub-lethal effects of structurally related conger terpenes on Myzus persicae. J Chem Ecol 23:1641–1650
Han SK, Ko YI, Park SJ, Jin IJ, Kim YM (1997) Oleanolic acid stabilize liposomal membranes. Lipids 32:769–773
Hu W, Cook BJ, Ampasala DR, Zheng S, Caputo G, Krell PJ, Retnakaran A, Arif BM, Feng Q (2004) Morphological and molecular effects of 20-hydroxyecdysone and its agonist tebufenozide on CF-203, a midgut-derived cell line from the spruce budworm, Choristoneura fumiferana. Arch Insect Biochem Physiol 55:68–78
Hua Y, Bentley MD, Cole BJW, Murray KD, Alford AR (1991) Triterpenes from the outer bark of Betula nigra. J Wood Chem Tech 11:503–516
Huang F, Chung BY, Bentley MD, Alford AR (1995) Colorado potato beetle antifeedants by simple modification of the birch bark triterpene betulin. J Agric Food Chem 43:2513–2516
Jagadeesh SG, Kripadanam GLD, Srimannarayana G (1998) Tobacco caterpillar antifeedant from the Gotti stem wood triterpene betulinic acid. J Agric Food Chem 46:2797–2799
Katerere DR, Gray AI, Nash RJ, Waigh RD (2003) Antimicrobial activity of pentacyclic triterpenes isolated from African Combretaceae. Phytochemistry 63:81–88
Kubo I, Hanke FJ, Asaka Y, Matsumoto T, He CH, Clardy J (1990) Insect antifeedants from tropical plants. Structure of dumsin. Tetrahedron 46:1512–1522
Kuo RY, Qian K, Morris-Natschke SL, Lee KH (2009) Plant derived triterpenes and analogues as antitumor and anti-HIV agents. Nat Prod Rep 26:1321–1344
Laurent P, Dooms C, Braeckman JC, Daloze D, Habib-Jiwan JL, Rozenberg R, Termonia A, Pasteels JM (2003) Recycling plant wax constituents for chemical defense: hemi-biosynthesis of triterpene saponins from β-amyrin in a leaf beetle. Naturwissenschaften 90:524–527
Lee MK, Kim YC (2001) Five novel neuroprotective triterpene esters of Ulmus davidiana var. japonica. J Nat Prod 64:328–331
Ley SV, Abad-Somovilla A, Anderson JC, Ayats C, Bänteli R, Beckmann E, Boyer A, Brasca MG, Brice A, Broughton HB, Burke BJ, Cleator E, Craig D, Denholm AA, Denton RM, Durand-Reville T, Gobbi LB, Göbel M, Gray BL, Grossmann RB, Gutteridge CE, Hahn N, Harding SL, Jennens DC, Jennens L, Lovell PJ, Lovell HJ, de la Puente ML, Kolb HC, Koot WJ, Maslen SL, McCusker CF, Mattes A, Pape AR, Pinto A, Santafianos D, Scott JS, Smith SC, Somers AQ, Spilling CD, Stelzer F, Toogood PL, Turner RM, Veitch GE, Wood A, Zumbrunn C (2008) The synthesis of azadirachtin: a potent insect antifeedant. Chem Eur J 14:10683–10704
Loeb MJ, De Loof A, Schoofs L, Isaac E (1998) Angiotensin II and angiotensin-converting enzyme as candidate compounds modulating the effects of testis ecdysiotropin in testes of the gypsy moth Lymantria dispar L. Gen Comput Endocrinol 112:232–239
Lugemwa PN, Huang FY, Bentley MD, Mendel MJ, Alford AR (1990) A Heliothis zea antifeedant from the abundant birch bark triterpene, betulin. J Agric Food Chem 38:493–496
Macías FA, Simonet AM, Esteban MD (1994) Potential allelophatic lupane triterpenes from bioactive fractions of Melilotus messanensis. Phytochemistry 36:1369–1379
Macías FA, Simonet AM, Esteban MD, Galindo JCG (1996) Triterpenoids from Melilotus messanensis: soyasapogenol G, the first natural carbonate derivative. Phytochemistry 41:1573–1577
Macías FA, Simonet AM, Galindo JCG (1997) Bioactive steroids and triterpenes from Melilotus messanensis and their allelopathic potential. J Chem Ecol 23:1781–1803
Macías-Rubalcava ML, Hernández-Bautista BE, Jiménez-Estrada M, Cruz-Ortega R, Anaya AL (2007) Pentacyclic triterpenes with selective bioactivity from Sebastiana adenophora leaves, Euphorbiaceae. J Chem Ecol 33:147–156
Mallavadhani UV, Mahapatra A, Raja SS, Manjuka C (2003) Antifeedant activity of some pentacyclic triterpene acids and their fatty acid ester analogues. J Agric Food Chem 51:1952–1955
Marheineke K, Grunewald S, Christie W, Reilander H (1998) Lipid composition of Spodoptera frugiperda (Sf9) and Trichoplusia ni (Tn) insect cells used for baculovirus infection. FEBS Lett 441:49–52
Matsuda K (1998) Feeding stimulants of leaf beetles. In: Jolivet P, Petitipierre E, Hsiao TH (eds) Biology of chrysomelidae. Kluwer Academic Publishers, Dordrecht, pp 41–56
Mazoir N, Benharref A, Bailén M, Reina M, González-Coloma A (2008) Bioactive triterpene derivatives from the latex of two Euphorbia species. Phytochemistry 69:1328–1338
Moiteiro C, Justino F, Tavares R, Marcelo-Curto MJ, Florencio MH, Nascimento MSJ, Pedro M, Cerqueira F, Pinto MM (2001) Synthetic seco-friedelane and friedelane derivatives as inhibitors of human lymphocyte proliferation and growth of human cancer cell lines in vitro. J Nat Prod 64:1273–1277
Moiteiro C, Justino F, Tavares R, Marcelo-Curto MJ, Nascimento MSJ, Pedro M, Pinto MM (2004) Hemisynthetic secofriedelane triterpenes with inhibitory activity against the growth of human cancer cell lines in vitro. J Nat Prod 67:1193–1196
Moiteiro C, Joao M, Curto OM, Mohamed N, Bailen M, Martínez-Díaz R, González-Coloma A (2006) Biovalorization of friedelane triterpenes derived from cork processing industry byproducts. J Agric Food Chem 54:3566–3571
Muceniece R, Saleniece K, Rumaks J, Krigere L, Dzirkale Z, Mezhapuke R, Zharkova O, Klusa V (2008) Betulin binds to γ-aminobutyric acid receptors and exert anticolvunsant action in mice. Pharm Biochem Behav 90:712–716
Mullin CA, Chyb S, Eichenseer H, Hollister B, Frazier JL (1994) Neuroreceptor mechanisms in insect gustation: a pharmacological approach. J Insect Physiol 40:913–931
Mullin CA, González-Coloma A, Gutiérrez C, Reina M, Eichenseer H, Hollister B, Chyb S (1997) Antifeedant effects of some novel terpenoids on Chrysomelidae beetles: comparison with alkaloids on an alkaloid-adapted and non adapted species. J Chem Ecol 23:1851–1865
Nakatani M (1999) Insect antifeeding limonoids from the chinaberry tree Melia azedarach Linn. and related compounds. In: Cooper R, Snyder JK (eds) Biology–chemistry interface: a tribute to Koji Nakanishi. Marcel Dekker, New York, pp 1–22
Nathan SS, Choi MY, Paik CH, Seo HY (2007) The food consumption, utilization, and detoxification enzyme activity of the rice leaffolder larvae after treatment with Dysoxylum triterpenes. Pest Biochem Physiol 88:260–267
Oleszek W (1993) Allelophatic potentials of alfalfa (Medicago sativa) saponins: their relation to antifungal and hemolytic activities. J Chem Ecol 19:1063–1074
Poitut S, Bues S (1970) Elevage de plusieursespeces de Lepidopteres Noctuidae sur milleu artificial simplifié. Ann Zool Ecol Anim 2:79–91
Polonsky J (1985) Quassinoid bitter principles II. In: Herz W, Grisebach H, Kirby GW, Ch Tamm (eds) Progress in the chemistry of organic natural products, vol 47. Springer, New York, pp 221–264
Pungitore CR, García M, Gianello JC, Sosa ME, Tonn CE (2005) Insecticidal and antifeedant effects of Junellia aspera (Verbenaceae) triterpenes and derivatives on Sitophilus oryzae (Coleoptera: Curculionidae). J Stored Prod Res 41:433–443
Qi SA, Wu DG, Chen L, Ma YB, Luo XD (2003) Insect antifeedant from Munronia henryi: structure of munroniamide. J Agric Food Chem 51:6949–6952
Reina M, González-Coloma A, Gutiérrez C, Cabrera R, Rodríguez ML, Fajardo V, Villarroel L (2001) Defensive chemistry of Senecio miser Hook. J Nat Prod 64:6–11
Sanjan KP, Partho PD (1993) Influence of asiatic acid, a triterpenoid from Shorea robusta, in the feeding and enzyme activity of Oxya fuscovittata (Insecta, Orthoptera). J Appl Entomol 115:506–510
Sanz J, Soria AC, García-Vallejo MC (2004) Analysis of volatile components of Lavandula luisieri L. by direct thermal desorption-gas chromatography-mass spectrometry. J Chromatography 1024:139–146
Saxena BB, Zhu L, Hao M, Kisilis E, Katdare M, Oktem O, Bomshteyn A, Rathnam P (2006) Boc-lysinate-betulonic acid: a potent, anti-prostate cancer agent. Bioorg Med Chem 14:6349–6358
Segal R, Pisanty S, Wormser R, Azaz E, Seia MN (2006) Anticariogenic activity of licorine and glycyrrhizine I. Inhibition of in vitro plaque formation by Streptococcus mutans. J Pharm Sc 74:79–81
Setzer W, Setzer MC (2003) Plant-derived triterpenoids as potential antineoplastic agents. Mini Rev Med Chem 3:540–556
Shankaranarayana KH, Ayyar KS, Rao GSK (1980) Insect growth inhibitor from the bark of Santalum album. Phytochemistry 19:1239–1240
Shen LR, Guo D, Yu YM, Yin BW, Zhao L, Shi QW, Wang YL, Huo CH (2009) Chemical constituents of plant from the genus Xylocarpus. Chem Biodiv 6:1293–1308
Shukla YN, Srivastava R, Tripathi AK, Prajapati V (2000) Characterization of an ursane triterpenoid from Centella asiatica with growth inhibitory activity against Spilarctia obliqua. Pharm Biol 38:262–267
Mukherjee R, Srivatava SK, Siddiqui MJA, Jaggi M, Singh AT, Vardhan A, Singh MK, Rajendran P, Jajoo HK, Burman AC, Kumar V, Rani D, Agarwal SK (2006) Novel betulinic acid derivatives A-ring condensed to a heterocyclic group. Pat. WO/2006/085334
Simmonds MSJ, Stevenson PC, Porter EA, Veitch N (2001) Insect antifeedant activity of three new tetranortriterpenois from Trichilia pallida. J Nat Prod 64:1117–1120
Suresh G, Gopalakrishnan G, Wesley SD, Singh NDP, Malathi R, Rajan SS (2002) Insect antifeedant activity of tetranortriterpenoids from the Rutales. A perusal of structural relations. J Agric Food Chem 50:4484–4490
Tamura Y, Hattori M, Konno K, Kono Y, Honda H, Ono H, Yoshida M (2004) Triterpenoid and caffeic acid derivatives in the leaves of ragweed, Ambrosia artemisiifolia L. (Asterales: Asteraceae), as feeding stimulants of Ophraella communa Le Sage (Coleoptera: Chrysomelidae). Chemoecology 14:113–118
Tapondjou LA, Lontsi D, Sondengam BL, Choi J, Lee KT, Jung HJ (2003) In vivo anti-conceptive and anti-inflammatory effects of the two triterpenes, ursolic acid and 23-hydroxyursolic acid, from Cussonia bancoensis. Arch Pharm Res 26:143–146
Tava A, Avato P (2006) Chemical and biological activity of triterpene saponins from Medicago species. Nat Prod Commun 1:1159–1180
Taylor WG, Fields PG, Sutherland DH (2004) Insecticidal components from field pea extracts: soyasaponins and lysolecithins. J Agric Food Chem 52:7484–7490
Webb J, Fowls R, Rees HH (1995) Enzymes of ecdysteroid transformation and inactivation in the midgut of the cotton leafworm Spodoptera littoralis: Properties and development profiles. Biochem J 312:561–568
Wen Y, Sun H, Liu J, Wu G, Zhang L, Wu X, Ni P (2005) Pentacyclic triterpenes. Part 1. The first example of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases. Bioorg Med Chem Lett 15:4944–4948
Wu J, Zhang S, Bruhn T, Xiao Q, Diung H, Bringmann G (2008) Xylogranatins F-R: Antifeedant from the Chinese mangrove, Xylocarpus granatum, a new biogenetic pathway to tetranortriterpenoids. Chem Eur J 14:1114–1129
Yasui H (2002) Identification of antifeedant in bitter gourd leaves and their effects on feeding behaviour of several lepidopteran species. JARQ 36:25–30
Yuan WH, Yi YH, Xue M, Zhang HW, La MP (2008) Two antifungal active triterpene glycosides from sea cucumber Holothuria (Microthele) axiloga. Chin J Nat Med 6:105–108
Zhu M, Philipson JD, Greengrass PM, Bowery NG (1996) Chemical and biological investigation of the root bark of Clerodendrum mandarinorum. Planta Med 62:393–396