Triterpene-based plant defenses

Phytochemistry Reviews

Volumn 10, Issue 2, 2011, Pages 245-260

  González Coloma, Azucena ^a   López Balboa, Carmen ^a   Santana, Omar ^a   Reina, Matías ^b   Fraga, Braulio M ^b  

^a INSTITUTO DE CIENCIAS AGRARIAS   (Spain)

^b INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

Antifeedant; Bioactivity; Cytotoxic; Phytotoxic; Triterpenes

Indexed keywords

3 OXO OLEAN 12 EN 28 OIC ACID; ANAGADIOL; BETA AMYRIN; BETULIC ACID; BETULIC ACID ACETATE; BETULIN; BETULIN DIACETATE; EPIFRIEDELINOL; EPIFRIEDELINOL ACETATE; FRIEDELIN; FRIEDELINOL; FRIEDELINOL ACETATE; GERMANICOL; GLUTINOL; INSECTICIDE; LUPEOL; LUPEOL ACETATE; OLEANOLIC ACID; OLEANOLIC ACID ACETATE; OLEANOLIC ACID METHYL ESTER; PENTACYCLIC TRITERPENE; RHOIPTELENOL; RHOIPTELENOL ACETATE; RHOIPTELENONE; TRITERPENE; UNCLASSIFIED DRUG; UVAOL DIACETATE;

ANIMAL CELL; APHID; ARMYWORM; ARTICLE; BIOLOGICAL ACTIVITY; CHO CELL; COLORADO POTATO BEETLE; CONTROLLED STUDY; CYTOTOXICITY; FEMALE; GERMINATION; INSECT CONTROL; INSECTICIDAL ACTIVITY; LETTUCE; MYZUS PERSICAE; NONHUMAN; PHYTOCHEMISTRY; PHYTOTOXICITY; PLANT DEFENSE; PRIORITY JOURNAL; SPODOPTERA LITTORALIS; STRUCTURE ACTIVITY RELATION;

HEXAPODA; LEPTINOTARSA DECEMLINEATA; MAMMALIA; MYZUS PERSICAE; SPODOPTERA LITTORALIS;

EID: 79954615573     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-010-9187-8     Document Type: Article

References (92)

1. WS Abbot 1925 A method of computing the effectiveness of fan insecticide J Econ Entomol 18 265 267
2. M Abe K Matsuda 2000 Feeding deterrents from Momordica charantia leaves to cucurbitaceous feeding beetle species Appl Entomol Zool 35 143 149 10.1303/aez.2000.143
3. MMB Almeida AMC Arriaga AKL Dos Santos TLG Lemos R Braz-Filho IJ Curcino-Vieira 2007 Occurrence and biological activity of quassinoids in the last decade Quim Nova 30 935 951 10.1590/S0100-40422007000400033 1:CAS:528:DC%2BD2sXotlOisrw%3D
4. AL Anaya R Mata A González-Coloma R Cruz-Ortega A Guadaño BE Hernández-Bautista G Ríos A Gómez-Pompa 2003 Allelochemical potencial of Callicarpa acuminata (Verbenaceae) J Chem Ecol 29 2725 2740 10.1023/B:JOEC.0000008019.22063.5c (Pubitemid 38018280)
5. J Avilla A Teixidó C Velázquez N Alvarenga E Ferro R Canela 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 10637057 10.1021/jf990008w 1:CAS:528:DyaK1MXnslensbk%3D (Pubitemid 30054075)
6. N Baldovini S Lavoine-Hanneguelle G Ferrando G Dusart L Lizzani-Cuvelier 2005 Necrodane monoterpenoids from Lavandula luisieri Phytochemistry 66 1651 1655 15953623 10.1016/j.phytochem.2005.04.040 1:CAS:528:DC%2BD2MXmvVWlsrc%3D (Pubitemid 41026617)
7. 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
8. JR Bloomquist 2003 Chloride channels as tools for developing selective insecticides Arch Insect Biochem Physiol 54 145 156 14635176 10.1002/arch.10112 1:CAS:528:DC%2BD3sXps1ers7o%3D (Pubitemid 38592053)
9. JR Bloomquist DR Boina E Chow PR Carlier M Reina A González-Coloma 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 10.1016/j.pestbp.2007.12.002 1:CAS:528:DC%2BD1cXksVartL8%3D
10. J Bretón J Delgado-Martín BM Fraga AG González 1969 Triterpenos de la Euphorbia paralias Anales Real Soc Españ Fis Quim 65b 61 67
11. Butterworth JH, Morgan ED (1968) Isolation of a substance that suppresses feeding in locusts. Chem Commun, pp 23-24
12. C Caballero-George PML Vanderheyden Y Okamoto T Masaki Z Mbwambo S Apers MP Gupta L Pieters G Vauquelin A Vlietinck 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 15478202 10.1002/ptr.1521 1:CAS:528:DC%2BD2cXhtVGgsbzL (Pubitemid 39481692)
13. P Castañeda MR García E Hernández BA Torres AL Anaya R Mata 1992 Effects of some compounds isolated from Calaeodendron mexicanum Standl (Euphorbiaceae) on seeds and phytopathogenic fungi J Chem Ecol 18 1025 1037 10.1007/BF00980060
14. CL Cespedes JR Salazar M Martinez E Aranda 2005 Insect growth regulatory effects of some extracts and sterols from Myrtillocactus geometrizans (Cactaceae) against Spodoptera frugiperda and Tenebrio molitor Phytochemistry 66 2481 2493 16122768 10.1016/j.phytochem.2005.07.010 1:CAS:528:DC%2BD2MXhtFSmtrfJ (Pubitemid 41427773)
15. MV Chandravadana 1987 Identification of triterpenoid feeding deterrent of red pumpkin beetles (Aulacophora foveicollis) from Momordica charantia J Chem Ecol 13 1689 1694 10.1007/BF00980210 1:CAS:528:DyaL2sXlslalt7s%3D
16. CI Chang CC Kuo JY Chang YH Kuo 2004 Three new oleanane-type triterpenes from Ludwigia octovalvis with cytotoxic activity against two human cancer cell lines J Nat Prod 67 91 93 14738395 10.1021/np030267m 1:CAS:528: DC%2BD3sXpvFKiu7k%3D (Pubitemid 38141320)
17. B D'Abrosca A Florentino P Monaco S Pacifico 2005 Radical-scavenging activities of new hydroxylated ursane triterpenes from cv. Annurca apples Chem Biodiv 2 953 958 10.1002/cbdv.200590072 (Pubitemid 41057414)
18. MGM Danelli DC Soares HS Abreu LMT Pecanha EM Saraiva 2009 Leishmanicidal effect of LLD-3, a nor-triterpene isolated from Lophanthera lactescens Phytochemistry 70 608 614 19359020 10.1016/j.phytochem.2009.03.009 1:CAS:528:DC%2BD1MXltVynur4%3D
19. SF De Andrade E Comunello VF Noldin F Delle Monache V Cechinel Filho R Niero 2008 Antiulcerogenic activity of fractions and 3, 15-dioxo-21α- hydroxy-friedelane isolated from Maytenus robusta (Celastraceae) Arch Pharm Res 31 41 46 18277606 10.1007/s12272-008-1118-5
20. 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
21. P Dzubak M Hajduch D Vydra A Hustova M Vasnika D Biedermann M Lenka M Urban J Sarek 2006 Pharmacological activities of natural triterpenoids and their therapeutic implications Nat Prod Rep 23 394 411 16741586 10.1039/b515312n 1:CAS:528:DC%2BD28XmslaisLs%3D (Pubitemid 43847140)
22. SD Eigenbrode KE Espelie AM Shelton 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 10.1007/BF00984697
23. BM Fraga M Reina JG Luis ML Rodriguez 2003 Rhoiptelenol and rhoiptelenone, two pentacyclic triterpenes from Sideritis macrostachya Z Natursforch 58c 621 625 (Pubitemid 37224248)
24. L Fu S Zhang N Li J Wang M Zhao J Sakai T Hasegawa T Mitsui T Kataoka S Oka M Kiuchi K Hirose M Ando 2005 Three new triterpenes from Nerium oleander and biological activity of the isolated compounds J Nat Prod 68 198 206 15730243 10.1021/np040072u 1:CAS:528:DC%2BD2MXnvVemug%3D%3D (Pubitemid 40299806)
25. S Golawska 2007 Deterrence and toxicity of plants saponins for the pea aphid Acyrthosiphon pisum Harris J Chem Ecol 33 1598 1606 17610116 10.1007/s10886-007-9333-y 1:CAS:528:DC%2BD2sXot1yjtbc%3D (Pubitemid 47174809)
26. González AG, Bretón JL, Fraga BM (1971) Constituents of Labiatae.1 Anagadiol, a new triterpenes from Salvia broussonetii Benth. Chem Commun, pp 567-568
27. A González-Coloma C Gutiérrez R Cabrera M Reina 1997 Silphinene derivatives: their effects and modes of action on Colorado potato beetle J Agric Food Chem 45 946 950 10.1021/jf960574g (Pubitemid 127483734)
28. A González-Coloma A Guadaño C Gutiérrez R Cabrera E de la Peña G de la Fuente M Reina 1998 Antifeedant Delphinium diterpene alkaloids. Structure-activity relationships J Agric Food Chem 46 286 290 10554234 10.1021/jf970585p (Pubitemid 128488059)
29. A González-Coloma F Valencia N Martín JJ Hoffmann L Hutter JA Marco M Reina 2002 Silphinene sesquiterpenes as model insect antifeedants J Chem Ecol 28 117 129 11868669 10.1023/A:1013566919874 (Pubitemid 34165689)
30. A González-Coloma A Guadaño C de Inés R Martínez-Díaz D Cortés 2002 Selective action of acetogenin mitochondrial complex I inhibitors Z Naturforsch 57c 1028 1034 (Pubitemid 36137347)
31. A González-Coloma D Martin-Benito N Mohamed MC Garcia-Vallejo AC Soria 2006 Antifeedant effects and chemical composition of essential oils from different populations of Lavandula luisieri L Biochem Syst Ecol 34 609 616 10.1016/j.bse.2006.02.006
32. TR Govindachari G Suresh GN Krishna-Kumari T Rajamannar PD Partho 1999 Nymania-3: A bioactive triterpenoid from Dysoxylun malabaricum Fitoterapia 70 83 86 10.1016/S0367-326X(98)00036-7 1:CAS:528:DyaK1MXjvFyjtbo%3D (Pubitemid 29230114)
33. C Gutiérrez A Fereres M Reina R Cabrera A González-Coloma 1997 Behavioural and sub-lethal effects of structurally related conger terpenes on Myzus persicae J Chem Ecol 23 1641 1650 10.1023/B:JOEC.0000006428.00568.c5 (Pubitemid 27291664)
34. SK Han YI Ko SJ Park IJ Jin YM Kim 1997 Oleanolic acid stabilize liposomal membranes Lipids 32 769 773 9252966 10.1007/s11745-997-0098-9 1:CAS:528:DyaK2sXkvFeltrg%3D (Pubitemid 27328059)
35. W Hu BJ Cook DR Ampasala S Zheng G Caputo PJ Krell A Retnakaran BM Arif Q Feng 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 14745824 10.1002/arch.10124 1:CAS:528:DC%2BD2cXhsFOhs7Y%3D (Pubitemid 38592409)
36. Y Hua MD Bentley BJW Cole KD Murray AR Alford 1991 Triterpenes from the outer bark of Betula nigra J Wood Chem Tech 11 503 516 10.1080/02773819108051090 1:CAS:528:DyaK38XlsFKjtg%3D%3D
37. F Huang BY Chung MD Bentley AR Alford 1995 Colorado potato beetle antifeedants by simple modification of the birch bark triterpene betulin J Agric Food Chem 43 2513 2516 10.1021/jf00057a035 1:CAS:528:DyaK2MXns1CjtL4%3D
38. SG Jagadeesh GLD Kripadanam G Srimannarayana 1998 Tobacco caterpillar antifeedant from the Gotti stem wood triterpene betulinic acid J Agric Food Chem 46 2797 2799 10.1021/jf970768b 1:CAS:528:DyaK1cXktFKqtrw%3D (Pubitemid 128488374)
39. ULB Jayasinghe Y Fujimoto 1999 Insecticidal saponin from Pometia eximia Fitoterapia 70 87 88 10.1016/S0367-326X(98)00008-2 1:CAS:528:DyaK1MXjvFyjtbs%3D (Pubitemid 29230115)
40. DR Katerere AI Gray RJ Nash RD Waigh 2003 Antimicrobial activity of pentacyclic triterpenes isolated from African Combretaceae Phytochemistry 63 81 88 12657301 10.1016/S0031-9422(02)00726-4 1:CAS:528:DC%2BD3sXit1Knt7g%3D (Pubitemid 36427443)
41. I Kubo FJ Hanke Y Asaka T Matsumoto CH He J Clardy 1990 Insect antifeedants from tropical plants. Structure of dumsin Tetrahedron 46 1512 1522 10.1016/S0040-4020(01)81960-8
42. RY Kuo K Qian SL Morris-Natschke KH Lee 2009 Plant derived triterpenes and analogues as antitumor and anti-HIV agents Nat Prod Rep 26 1321 1344 19779642 10.1039/b810774m 1:CAS:528:DC%2BD1MXhtFOiu7rF
43. P Laurent C Dooms JC Braeckman D Daloze JL Habib-Jiwan R Rozenberg A Termonia JM Pasteels 2003 Recycling plant wax constituents for chemical defense: hemi-biosynthesis of triterpene saponins from β-amyrin in a leaf beetle Naturwissenschaften 90 524 527 14610652 10.1007/s00114-003-0471-y 1:CAS:528:DC%2BD3sXovVKms7Y%3D (Pubitemid 37491652)
44. MK Lee YC Kim 2001 Five novel neuroprotective triterpene esters of Ulmus davidiana var. japonica J Nat Prod 64 328 331 11277749 10.1021/np0004799 1:CAS:528:DC%2BD3MXhsFKhtrc%3D (Pubitemid 32249797)
45. SV Ley A Abad-Somovilla JC Anderson C Ayats R Bänteli E Beckmann A Boyer MG Brasca A Brice HB Broughton BJ Burke E Cleator D Craig AA Denholm RM Denton T Durand-Reville LB Gobbi M Göbel BL Gray RB Grossmann CE Gutteridge N Hahn SL Harding DC Jennens L Jennens PJ Lovell HJ Lovell ML de la Puente HC Kolb WJ Koot SL Maslen CF McCusker A Mattes AR Pape A Pinto D Santafianos JS Scott SC Smith AQ Somers CD Spilling F Stelzer PL Toogood RM Turner GE Veitch A Wood C Zumbrunn 2008 The synthesis of azadirachtin: a potent insect antifeedant Chem Eur J 14 10683 10704 10.1002/chem.200801103 1:CAS:528:DC%2BD1cXhsV2ktb3F
46. J Liu 1995 Pharmacology of oleanolic and ursolic acids J Ethnopharm 49 57 68 10.1016/0378-8741(95)90032-2 1:CAS:528:DyaK28Xht12gtL4%3D
47. MJ Loeb A De Loof L Schoofs E Isaac 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 10.1006/gcen.1998.7169 1:CAS:528:DyaK1cXnsVSiurs%3D (Pubitemid 28516178)
48. PN Lugemwa FY Huang MD Bentley MJ Mendel AR Alford 1990 A Heliothis zea antifeedant from the abundant birch bark triterpene, betulin J Agric Food Chem 38 493 496 10.1021/jf00092a035 1:CAS:528:DyaK3cXhtFCisL8%3D
49. FA Macías AM Simonet MD Esteban 1994 Potential allelophatic lupane triterpenes from bioactive fractions of Melilotus messanensis Phytochemistry 36 1369 1379 10.1016/S0031-9422(00)89726-5 (Pubitemid 2133903)
50. FA Macías AM Simonet MD Esteban JCG Galindo 1996 Triterpenoids from Melilotus messanensis: soyasapogenol G, the first natural carbonate derivative Phytochemistry 41 1573 1577 10.1016/0031-9422(95)00812-8 (Pubitemid 3040908)
51. FA Macías AM Simonet JCG Galindo 1997 Bioactive steroids and triterpenes from Melilotus messanensis and their allelopathic potential J Chem Ecol 23 1781 1803 10.1023/B:JOEC.0000006451.19649.a0 (Pubitemid 27347644)
52. ML Macías-Rubalcava BE Hernández-Bautista M Jiménez-Estrada R Cruz-Ortega AL Anaya 2007 Pentacyclic triterpenes with selective bioactivity from Sebastiana adenophora leaves, Euphorbiaceae J Chem Ecol 33 147 156 17151909 10.1007/s10886-006-9208-7 (Pubitemid 46011209)
53. UV Mallavadhani A Mahapatra SS Raja C Manjuka 2003 Antifeedant activity of some pentacyclic triterpene acids and their fatty acid ester analogues J Agric Food Chem 51 1952 1955 12643657 10.1021/jf020691d 1:CAS:528: DC%2BD3sXhsVaqu74%3D
54. K Marheineke S Grunewald W Christie H Reilander 1998 Lipid composition of Spodoptera frugiperda (Sf9) and Trichoplusia ni (Tn) insect cells used for baculovirus infection FEBS Lett 441 49 52 9877163 10.1016/S0014-5793(98)01523-3 1:CAS:528:DyaK1cXotVKjs70%3D (Pubitemid 29012370)
55. 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
56. N Mazoir A Benharref M Bailén M Reina A González-Coloma 2008 Bioactive triterpene derivatives from the latex of two Euphorbia species Phytochemistry 69 1328 1338 18304594 10.1016/j.phytochem.2008.01.004 1:CAS:528:DC%2BD1cXktVCiu78%3D
57. C Moiteiro F Justino R Tavares MJ Marcelo-Curto MH Florencio MSJ Nascimento M Pedro F Cerqueira MM Pinto 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 11678649 10.1021/np010217m 1:CAS:528:DC%2BD3MXmvVKiu74%3D (Pubitemid 33029205)
58. C Moiteiro F Justino R Tavares MJ Marcelo-Curto MSJ Nascimento M Pedro MM Pinto 2004 Hemisynthetic secofriedelane triterpenes with inhibitory activity against the growth of human cancer cell lines in vitro J Nat Prod 67 1193 1196 15270581 10.1021/np0498915 1:CAS:528:DC%2BD2cXlsFemsLw%3D (Pubitemid 38971687)
59. C Moiteiro M Joao OM Curto N Mohamed M Bailen R Martínez- Díaz A González-Coloma 2006 Biovalorization of friedelane triterpenes derived from cork processing industry byproducts J Agric Food Chem 54 3566 3571 19127726 10.1021/jf0531151 1:CAS:528:DC%2BD28XjslChtLs%3D (Pubitemid 43844182)
60. R Muceniece K Saleniece J Rumaks L Krigere Z Dzirkale R Mezhapuke O Zharkova V Klusa 2008 Betulin binds to γ-aminobutyric acid receptors and exert anticolvunsant action in mice Pharm Biochem Behav 90 712 716 10.1016/j.pbb.2008.05.015 1:CAS:528:DC%2BD1cXhtVClurbJ
61. CA Mullin S Chyb H Eichenseer B Hollister JL Frazier 1994 Neuroreceptor mechanisms in insect gustation: a pharmacological approach J Insect Physiol 40 913 931 10.1016/0022-1910(94)90130-9 1:CAS:528:DyaK2MXit1Crurs%3D (Pubitemid 2161530)
62. CA Mullin A González-Coloma C Gutiérrez M Reina H Eichenseer B Hollister S Chyb 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 10.1023/B:JOEC.0000006455.72602.3f 1:CAS:528:DyaK2sXlt1Cgu7o%3D
63. 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
64. SS Nathan MY Choi CH Paik HY Seo 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 10.1016/j.pestbp. 2006.12.004 1:CAS:528:DC%2BD2sXlt1Wqs78%3D (Pubitemid 46729559)
65. W Oleszek 1993 Allelophatic potentials of alfalfa (Medicago sativa) saponins: their relation to antifungal and hemolytic activities J Chem Ecol 19 1063 1074 10.1007/BF00987369 1:CAS:528:DyaK3sXms1Kqsbc%3D
66. S Poitut S Bues 1970 Elevage de plusieursespeces de Lepidopteres Noctuidae sur milleu artificial simplifié Ann Zool Ecol Anim 2 79 91
67. 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 (Pubitemid 15031281)
68. CR Pungitore M García JC Gianello ME Sosa CE Tonn 2005 Insecticidal and antifeedant effects of Junellia aspera (Verbenaceae) triterpenes and derivatives on Sitophilus oryzae (Coleoptera: Curculionidae) J Stored Prod Res 41 433 443 10.1016/j.jspr.2004.07.001 1:CAS:528: DC%2BD2MXisVCnsLk%3D (Pubitemid 40383814)
69. SA Qi DG Wu L Chen YB Ma XD Luo 2003 Insect antifeedant from Munronia henryi: structure of munroniamide J Agric Food Chem 51 6949 6952 14611152 10.1021/jf030292y 1:CAS:528:DC%2BD3sXot1OjtLg%3D
70. M Reina A González-Coloma C Gutiérrez R Cabrera ML Rodríguez V Fajardo L Villarroel 2001 Defensive chemistry of Senecio miser Hook J Nat Prod 64 6 11 11170657 10.1021/np000114o 1:CAS:528: DC%2BD3cXosVOgt7g%3D (Pubitemid 32109266)
71. KP Sanjan PD Partho 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 10.1111/j.1439-0418.1993. tb00420.x
72. J Sanz AC Soria MC García-Vallejo 2004 Analysis of volatile components of Lavandula luisieri L. by direct thermal desorption-gas chromatography-mass spectrometry J Chromatography 1024 139 146 10.1016/j.chroma.2003.10.024 1:CAS:528:DC%2BD3sXps1OmtL0%3D (Pubitemid 37532541)
73. BB Saxena L Zhu M Hao E Kisilis M Katdare O Oktem A Bomshteyn P Rathnam 2006 Boc-lysinate-betulonic acid: a potent, anti-prostate cancer agent Bioorg Med Chem 14 6349 6358 16777417 10.1016/j.bmc.2006.05.048 1:CAS:528: DC%2BD28XosVOhsL0%3D (Pubitemid 44224077)
74. R Segal S Pisanty R Wormser E Azaz MN Seia 2006 Anticariogenic activity of licorine and glycyrrhizine I. Inhibition of in vitro plaque formation by Streptococcus mutans J Pharm Sc 74 79 81 10.1002/jps.2600740121
75. W Setzer MC Setzer 2003 Plant-derived triterpenoids as potential antineoplastic agents Mini Rev Med Chem 3 540 556 12871157 10.2174/ 1389557033487854 1:CAS:528:DC%2BD3sXms1WgsLs%3D
76. KH Shankaranarayana KS Ayyar GSK Rao 1980 Insect growth inhibitor from the bark of Santalum album Phytochemistry 19 1239 1240 10.1016/0031-9422(80) 83096-2 1:CAS:528:DyaL3MXmsFyqsA%3D%3D
77. LR Shen D Guo YM Yu BW Yin L Zhao QW Shi YL Wang CH Huo 2009 Chemical constituents of plant from the genus Xylocarpus Chem Biodiv 6 1293 1308 10.1002/cbdv.200800025 1:CAS:528:DC%2BD1MXht1Sqsr%2FE
78. YN Shukla R Srivastava AK Tripathi V Prajapati 2000 Characterization of an ursane triterpenoid from Centella asiatica with growth inhibitory activity against Spilarctia obliqua Pharm Biol 38 262 267 21214472 1:CAS:528: DC%2BD3cXovFOisL4%3D
79. 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
80. MSJ Simmonds PC Stevenson EA Porter N Veitch 2001 Insect antifeedant activity of three new tetranortriterpenois from Trichilia pallida J Nat Prod 64 1117 1120 11520244 10.1021/np010197o 1:CAS:528:DC%2BD3MXls12qu7c%3D (Pubitemid 32800356)
81. G Suresh G Gopalakrishnan SD Wesley NDP Singh R Malathi SS Rajan 2002 Insect antifeedant activity of tetranortriterpenoids from the Rutales. A perusal of structural relations J Agric Food Chem 50 4484 4490 12137465 10.1021/jf025534t 1:CAS:528:DC%2BD38XltVahur8%3D (Pubitemid 34823970)
82. Y Tamura M Hattori K Konno Y Kono H Honda H Ono M Yoshida 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 10.1007/s00049-004-0269-1 1:CAS:528:DC%2BD2cXjslersLw%3D (Pubitemid 38463870)
83. LA Tapondjou D Lontsi BL Sondengam J Choi KT Lee HJ Jung 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 12643591 10.1007/BF02976660 1:CAS:528:DC%2BD3sXitlCqsr8%3D (Pubitemid 43086235)
84. A Tava P Avato 2006 Chemical and biological activity of triterpene saponins from Medicago species Nat Prod Commun 1 1159 1180 1:CAS:528: DC%2BD2sXhsFaksr0%3D
85. WG Taylor PG Fields DH Sutherland 2004 Insecticidal components from field pea extracts: soyasaponins and lysolecithins J Agric Food Chem 52 7484 7490 15675793 10.1021/jf0308051 1:CAS:528:DC%2BD2cXpslentbY%3D
86. J Webb R Fowls HH Rees 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 8526871 1:CAS:528:DyaK2MXpvVensbw%3D (Pubitemid 26002226)
87. Y Wen H Sun J Liu G Wu L Zhang X Wu P Ni 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 16169219 10.1016/j.bmcl.2005.08.026 1:CAS:528:DC%2BD2MXhtVynu7%2FO (Pubitemid 41400161)
88. J Wu S Zhang T Bruhn Q Xiao H Diung G Bringmann 2008 Xylogranatins F-R: Antifeedant from the Chinese mangrove, Xylocarpus granatum, a new biogenetic pathway to tetranortriterpenoids Chem Eur J 14 1114 1129
89. H Yasui 2002 Identification of antifeedant in bitter gourd leaves and their effects on feeding behaviour of several lepidopteran species JARQ 36 25 30 1:CAS:528:DC%2BD38Xks1WrsL0%3D (Pubitemid 35008398)
90. WH Yuan YH Yi M Xue HW Zhang MP La 2008 Two antifungal active triterpene glycosides from sea cucumber Holothuria (Microthele) axiloga Chin J Nat Med 6 105 108 10.3724/SP.J.1009.2008.00105 1:CAS:528:DC%2BD1cXltlSrs70%3D (Pubitemid 351454308)
91. M Zhu JD Philipson PM Greengrass NG Bowery 1996 Chemical and biological investigation of the root bark of Clerodendrum mandarinorum Planta Med 62 393 396 9005449 10.1055/s-2006-957923 1:CAS:528:DyaK28XnsVyhs7Y%3D (Pubitemid 26370326)
92. YM Zhu JK Shen HK Wang LM Cosentino KH Lee 2001 Synthesis and anti-HIV activity of oleanolic acid derivatives Bioorg Med Chem Lett 11 3115 3118 11720855 10.1016/S0960-894X(01)00647-3 1:CAS:528:DC%2BD3MXoslahs7Y%3D (Pubitemid 33092005)