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2014 | 61 | 2 |
Tytuł artykułu

Triterpene sapogenins with oleanene skeleton: chemotypes and biological activities

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
 Critical survey of a selected class of pentacyclic triterpenes - the oleanane family, is presented based on current literature in order to underline their value for medicinal chemistry and drug development potential. Oleanenes may be considered as a renewable resource of valuable research materials which are structurally diverse, inherently biocompatible and have built-in affinity for many categories of functional proteins. Although availability of particular compounds from natural sources may be very low, synthetic methods elaborated by generations of chemists, secure a way to obtaining desirable structures from commercial starting materials.
Słowa kluczowe
Wydawca
-
Rocznik
Tom
61
Numer
2
Opis fizyczny
p.227-243,ref.
Twórcy
autor
  • Pharmaceutical Research Institute, Warsaw, Poland
  • Pharmaceutical Research Institute, Warsaw, Poland
Bibliografia
  • Adams MM, Damani P, Perl NR, Won A, Hong F, Livingston PO, Ragupathi G, Gin DY (2010) Design and synthesis of potent Quillaja saponin vaccine adjuvants. J Am Chem Soc 132: 1939-1945.  
  • Arrau S, Delporte C, Cartagena C, Rodríguez-Díaz M, González P, Silva X, Cassels BK, Miranda HF (2011) Antinociceptive activity of Quillaja saponaria Mol. saponin extract, quillaic acid and derivatives in mice. J Ethnopharmacol 133: 164-167. 
  • Augustin JM, Kuzina V, Andersen SB, Bak S (2011) Molecular activities, biosynthesis and evolution of triterpenoid saponins. Phytochemistry 72: 435-457. 
  • Azimova SS (2013) Triterpene glycosides: Natural compounds. Plant sources, structure and properties, Springer, New York.
  • Bag BG, Dey PP, Dinda SK, Sheldrick WS, Oppel IM (2008) A simple route for renewable nano-sized arjunolic and asiatic acids and self- assembly of arjuna-bromolactone. Beilstein J Org Chem 4: DOI:10.3762/bjoc.4.24. 
  • Baldwin JE, Jones RH, Najera C, Yus M (1985) Functionalization of unactivated methyl groups through cyclopalladation reactions. Tetrahedron 41: 699-711.
  • Bishayee A, Ahmed S, Brankov N, Perloff M (2011) Triterpenoids as potential agents for the chemoprevention and therapy of breast cancer. Front Biosci 16: 980-996. 
  • Chadalapaka G, Jutooru I, McAlees A, Stefanac T, Safe S (2008) Structure-dependent inhibition of bladder and pancreatic cancer cell growth by 2-substituted glycyrrhetinic and ursolic acid derivatives. Bioorg Med Chem Lett 18: 2633-2639. 
  • Chen J, Gong Y, Liu J, Hua W, Zhang L, Sun H (2008) Synthesis and biological evaluation of novel pyrazolo (4,3-b) oleanane derivatives as inhibitors of glycogen phosphorylase. Chem Biodivers 5: 1304-1312. 
  • de la Puerta R, Martinez-Dominguez E, Ruiz-Gutierrez V (2000) Effect of minor components of virgin olive oil on topical anti-inflammatory assays. Zeitschrift für Naturforschung 55: 814-819. 
  • Dinda B, Debnath S, Mohanta BC, Harigaya Y (2010) Naturally occurring triterpenoid saponins. Chem Biodivers 7: 2327-2580. 
  • Eschenmoser A, Arigoni D (2005) Revisited after 50 Years: the 'stereochemical interpretation of the biogenetic isoprene rule for the triterpenes. Helv Chim Acta 88: 3011-3050.
  • Eschenmoser A, Ruzicka L, Jeger O, Arigoni D (1955) Zur Kenntnis der Triterpene. 190. Eine Stereochemische Interpretation der Biogenetischen Isoprenregel bei den Triterpenen. Helv Chim Acta 38: 1890-1904.
  • Farina C, Pinza M, Pifferi G (1998) Synthesis and anti-ulcer activity of new derivatives of glycyrrhetic, oleanolic and ursolic acids. Il Farmaco 53: 22-32. 
  • Froelich A, Gzella AK (2010) Oleanolic acid ethanol monosolvate. Acta Crystallogr Sect E Struct Rep Online 66: o2790. DOI:10.1107/S1600536810039929. 
  • Fu L, Gribble GW (2013) Efficient and scalable synthesis of bardoxolone methyl (CDDO-methyl Ester). Organic Lett 15: 1622-1625. 
  • Fukushima O, Seki H, Ohyama K, Ono E, Umemoto N, Mizutani M, Saito K, Muranaka T (2011) CYP716A Subfamily members are multifunctional oxidases in triterpenoid biosynthesis. Plant Cell Physiol 52: 2050-2061. 
  • Geisler K, Hughes RK, Sainsbury F, Lomonossoff GP, Rejzek M, Fairhurst S, Olsen CE, Motawia MS, Melton RE, Hemmings AM, Bak S, Osbourn A (2013) Biochemical analysis of a multifunctional cytochrome P450 (CYP51) enzyme required for synthesis of antimicrobial triterpenes in plants. Proc Natl Acad Sci USA 110: E3360-E3367. 
  • Ghosh J, Sil PC (2013) Arjunolic acid: A new multifunctional therapeutic promise of alternative medicine. Biochimie 95: 1098-1109. 
  • Graebin CS, Verli H, Guimaraes JA (2010) Glycyrrhizin and glycyrrhetic acid: scaffolds to promising new pharmacologically active compounds. J Braz Chem Soc 21: 1595-1615.
  • Gruza MM, Jatczak K, Zagrodzki B, Łaszcz M, Koziak K, Malińska M, Cmoch P, Giller T, Zegrocka-Stendel O, Woźniak K, Grynkiewicz G (2013) Preparation, purification and regioselective functionalization of protoescigenin - the main aglycone of escin complex. Molecules 18: 4389-4402. 
  • Hemalatha T, Pulavendran S, Balachandran C, Manohar BM, Puvanakrishnan R (2010) Arjunolic acid: A novel phytomedicine with multifunctional therapeutic applications. Indian J Exp Biol 48: 238-247. 
  • Hill RA, Connolly JD (2013) Triterpenoids. Nat Prod Rep 30: 1028-1065. 
  • Hostettmann K, Marston A (2005) Saponins. Cambridge University Press, Cambridge. 
  • Ijichi S, Tamagaki S (2005) Molecular design of sweet tasting compounds based on 3β-amino-3β-deoxy-18β-glycyrrhetinic acid: amido functionality eliciting tremendous sweetness. Chem Lett 34: 356-357.
  • Ikeda T, Yokomizo K, Okawa M, Tsuchihashi R, Kinjo J, Nohara T, Uyeda M (2005) Anti-herpes virus type 1 activity of oleanane-type triterpenoids. Biol Pharm Bull 28: 1779-1781. 
  • Ireland RE, Dawson MI, Welch SC, Hagenbach A, Bordner J, Trus B (1973) Total synthesis of terpenes, XVIII. Convergent, stereoselective total synthesis of the unsymmetrical pentacyclic triterpene alnusenone. J Am Chem Soc 95: 7829-7841.
  • Johnson WS, Plummer MS, Reddy SP, Bartlett WR (1993) Cation-stabilizing auxiliaries in polyene cyclizations. 7. The fluorine atom as a cation-stabilizing auxiliary in biomimetic polyene cyclizations. 4. Total synthesis of dl-β-amyrin. J Am Chem Soc 115: 515-521.
  • Kamble B, Gupta A, Patil D, Khatal L, Janrao S, Moothedath I, Duraiswamy B (2013) Determination of gymnemagenin in rat plasma using high-performance liquid chromatography-tandem mass spectrometry: application to pharmacokinetics after oral administration of Gymnema sylvestre extract. Biomedical Chromatography 27: 669-675. 
  • Konopleva M, Tsao T, Estrov Z, Lee RM, Wang RY, Jackson CE, McQueen T, Monaco G, Munsell M, Belmont J, Kantarjian H, Sporn MB, Andreeff M (2004) The synthetic triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid induces caspase-dependent and -independent apoptosis in acute myelogenous leukemia. Cancer Res 64: 7927-7935. 
  • Konoshima T, Takasaki M, Ichiishi E, Tokuda H, Nishino H, Duc NM, Kasai R, Yamasaki K (1999) Cancer chemopreventive activity of majonoside-R2 from Vietnamese ginseng, Panax vietnamensis. Cancer Lett 147: 11-16. 
  • Kroes BH, Beukelman CJ, Van Den Berg AJ, Wolbink GJ, Van Dijk H, Labadie RP (1997) Inhibition of human complement by β-glycyrrhetinic acid. Immunology 90: 115-120. 
  • Liang Z, Zhang L, Li L, Liu J, Li H, Zhang L, Chen L, Cheng K, Zheng M, Wen X, Zhang P, Hao J, Gong Y, Zhang X, Zhu X, Chen J, Liu H, Jiang H, Luo C, Sun H (2011) Identification of pentacyclic triterpenes derivatives as potent inhibitors against glycogen phosphorylase based on 3D-QSAR studies. Eur J Med Chem 46: 2011-2021. 
  • Liby KT, Sporn MB (2012) Synthetic oleanane triterpenoids: multifunctional drugs with a broad range of applications for prevention and treatment of chronic disease. Pharmacol Rev 64: 972-1003. 
  • Liu J (2005) Oleanolic acid and ursolic acid: research perspectives. J Ethnopharmacol 100: 92-94. 
  • Liu J, Sun H, Wang X, Mu D, Liao H, Zhang L (2007) Effects of oleanolic acid and maslinic acid on hyperlipidemia. Drug Dev Res 68: 261-266.
  • Lodeiro S, Xiong Q, Wilson WK, Kolesnikova MD, Onak CS, Matsuda SP (2007) An oxidosqualene cyclase makes numerous products by diverse mechanisms: a challenge to prevailing concepts of triterpene biosynthesis. J Am Chem Soc 129: 11213-11222. 
  • Maartmann-Moe K, Bicknell W, Francis GW (1987) Structure of olean-12(13)-en-3β-yl acetate. Acta Crystallogr C Struct Chem 43: 2362-2364.
  • Maitraie D, Hung CF, Tu HY, Liou YT, Wei BL, Yang SC, Wang JP, Lin CN (2009) Synthesis, anti-inflammatory, and antioxidant activities of 18β-glycyrrhetinic acid derivatives as chemical mediators of xanthine oxidase inhibitors. Bioorg Med Chem 17: 2785-2792. 
  • Mandal D, Panda N, Kumar S, Banerjee S, Mandal NB, Sahu NP (2006) A triterpenoid saponin possessing antileishmanial activity from the leaves of Careya arborea. Phytochemistry 67: 183-190. 
  • Manez R, Recio MC, Giner RM, Rios JL (1997) Effect of selected triterpenoids on chronic dermal inflammation. Eur J Pharmacol 334: 103-105. 
  • Martin R, Hernandez M, Cordova C, Nieto ML (2012) Natural triterpenes modulate immune-inflammatory markers of experimental autoimmune encephalomyelitis: therapeutic implications for multiple sclerosis. British J Pharmacol 166: 1708-1723. 
  • Medina-Franco JL, Giulianotti MA, Welmaker GS, Houghten RA (2013) Shifting from the single to the multitarget paradigm in drug discovery. Drug Discov Today 18: 495-501. 
  • Morikawa T, Li N, Nagatomo A, Matsuda H, Li X, Yoshikawa M (2006) Triterpene saponins with gastroprotective effects from tea seed (the seeds of Camellia sinensis). J Nat Prod 69: 185-190. 
  • Moses T, Pollier J, Thevelein JM, Goossens A (2013) Bioengineering of plant (tri)terpenoids: from metabolic engineering of plants to synthetic biology in vivo and in vitro. New Phytologist 200: 27-43. 
  • Negi JS, Negi PS, Pant GJ, Rawat MSM, Negi SK (2013) Naturally occurring saponins: chemistry and biology. J Poison Med Plant Res 1: 006-011.
  • Neufeldt SR, Sanford MS. (2010) O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization. Org Lett 12: 532-535. 
  • Nishino H, Nishino A, Takayasu J, Hasegawa T, Iwashima A, Hirabayashi K, Iwata S, Shibata S (1988) Inhibition of the tumor-promoting action of 12-O-tetradecanoylphorbol-13-acetate by some oleanane-type triterpenoid compounds. Cancer Res 48: 5210-5215. 
  • Parmar SK, Sharma TP, Airao VB, Bhatt R, Aghara R, Chavda S, Rabadiya SO, Gangwal AP (2013) Neuropharmacological effects of triterpenoids. Phytopharmacology 4: 354-372.
  • Parra A, Lopez PE, Garcia-Granados A (2010) Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive oil industry. Chem Biodivers 7: 421-439. 
  • Patel K, Gadewar M, Tripathi R (2012) Pharmacological and analytical aspects of gymnemic acid: a concise report. Asian Pac J Trop Dis 2: 414-416.
  • Pergola PE, Raskin P, Toto RD, Meyer CJ, Huff JW (2011) Bardoxolone methyl and kidney function in CKD with type 2 diabetes. N Engl J Med 365: 327-336. 
  • Podolak I, Galanty A, Sobolewska D (2010) Saponins as cytotoxic agents: a review. Phytochem Rev 9: 425-474. 
  • Pollier J, Goossens A (2012) Oleanolic acid. Phytochemistry 77: 10-15. 
  • Pollier J, Moses T, González-Guzmán M, De Geyter N, Lippens S, Vanden Bossche R, Marhavy P, Kremer A, Morreel K, Guérin CJ, Tava A, Oleszek W, Thevelein JM, Campos N, Goormachtig S, Goossens A (2013) The protein quality control system manages plant defence compound synthesis. Nature 504: 148-52. 
  • Porchezhian E, Dobriyal RM (2003) An overview on the advances of Gymnema sylvestre: chemistry, pharmacology and patents. Pharmazie 58: 5-12. 
  • Ragupathi G, Gardner JR, Livingston PO, Gin DY (2011) Natural and synthetic saponin adjuvant QS-21 for vaccines against cancer. Expert Rev Vaccines 10: 463-470. 
  • Rodríguez-Rodríguez R, Herrera MD, Perona JS, Ruiz-Gutiérrez V (2004) Potential vasorelaxant effects of oleanolic acid and erythrodiol, two triterpenoids contained in 'orujo' olive oil, on rat aorta. Brit J Nutrition 92: 635-642. 
  • Salminen A, Lehtonen M, Suuronen T, Kaarniranta K, Huuskonen J (2008) Terpenoids: natural inhibitors of NF-κB signaling with anti-inflammatory and anticancer potential. Cell Mol Life Sci 65: 2979-2999. 
  • Salvador JA, Silvestre SM, Pinto RM, Santos RC, LeRoux C (2012) New Applications for bismuth(iii) salts in organic synthesis: from bulk chemicals to steroid and terpene chemistry. Top Curr Chem 311: 143-178. 
  • Sánchez-González M, Lozano-Mena G, Juan ME, García-Granados A, Planas JM (2013) Assessment of the safety of maslinic acid, a bioactive compound from Olea europaea L. Mol Nutr Food Res 57: 339-346. 
  • Saneja A, Sharma C, Aneja KR, Pahwa R (2010) Gymnema sylvestre (Gurmar): A review. Der Pharmazia Lettre 2: 275-284.
  • Sheng H, Sun H (2011) Synthesis, biology and clinical significance of pentacyclic triterpenes: a multi-target approach to prevention and treatment of metabolic and vascular diseases. Nat Prod Rep 28: 543-593.  
  • Sporn MB, Liby KT, Yore MM, Fu L, Lopchuk JM, Gribble GW (2011) New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress. J Nat Prod 74: 537-545. 
  • Subba Rao GS, Kondaiah P, Singh SK, Ravanan P, Sporn MB (2008) Chemical modifications of natural triterpenes - glycyrrhetinic and boswellic acids: evaluation of their biological activity. Tetrahedron 64: 11541-11548. 
  • Sun H, Fang W-S, Wang W-Z, Hu C (2006) Structure-activity relationship of oleanane- and ursane-type triterpenoids. Bot Stud 47: 339-368.
  • Sun HX, Xie Y, Ye YP (2009) Advances in saponin-based adjuvants. Vaccine 27: 1787-1796. 
  • Surendra H, Corey EJ (2009) A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol. J Am Chem Soc 131: 13928-13929. 
  • Tatsuzaki J, Taniguchi M, Bastow KF, Nakagawa-Goto K, Morris-Natschke SL, Itokawa H, Baba K, Lee KH (2007) Anti-tumor agents 255: novel glycyrrhetinic acid - dehydrozingerone conjugates as cytotoxic agents. Bioorg Med Chem 15: 6193-6199. 
  • Tayek JA, Kalantar-Zadeh K (2013) The extinguished BEACON of bardoxolone: not a monday morning quarterback story. Am J Nephrol 37: 208-211. 
  • Thoppil RJ, Bishayee A (2011) Terpenoids as potential chemopreventive and therapeutic agents in liver cancer. World J Hepatol 3: 228-249. 
  • Ukiya M, Akihisa T, Tokuda H, Suzuki H, Mukainaka T, Ichiishi E, Yasukawa K, Kasahara Y, Nishino H (2002) Constituents of Compositae plants III. Anti-tumor promoting effects and cytotoxic activity against human cancer cell lines of triterpene diols and triols from edible chrysanthemum flowers. Cancer Lett 177: 7-12. 
  • Wen X-A, Liu J, Zhang L-Y, Ni P-Z, Sun H-B (2010) Synthesis and biological evaluation of arjunolic acid, bayogenin, hederagonic acid and 4-epi-hederagonic acid as glycogen phosphorylase inhibitors. Chin J Nat Med 8: 0441-0448.
  • Wang S, Fang W (2011) Design and synthesis of a dual linker for solid phase synthesis of oleanolic acid derivatives. Molecules 16: 4748-4763. 
  • Xue Z, Duan L, Liu D, Guo J, Ge S, et al. (2012) Divergent evolution of oxidosqualene cyclases in plants. New Phytologist 193: 1022-1038. 
  • Yadav VR, Prasad S, Sung B, Kannappan R, Aggarwal BB (2010) Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer. Toxins 2: 2428-2466. 
  • Yang X, Li G, Chen L, Zhang C, Wan X, Xu J (2011) Quantitative determination of hederagenin in rat plasma and cerebrospinal fluid by ultra fast liquid chromatography-tandem mass spectrometry method. J Chromatogr B Analyt Technol Biomed Life Sci 879: 1973-1979. 
  • Yin MC (2012) Anti-glycative potential of triterpenes: a mini-review. BioMedicine 2: 2-9.
  • Yoshikawa M, Murakami T, Matsuda H, Yamahara J, Murakami N, Kitagawa I (1996) Bioactive saponins and glycosides. III. Horse chestnut. (1): The structures, inhibitory effects on ethanol absorption and hypoglycemic activity of escins Ia, Ib, IIa, IIb and IIIa form the seeds of Aesculus hippocastanum L. Chem Pharm Bull 44: 1454-1464. 
  • Yu F, Wang Q, Zhang Z, Peng YY, Qiu YY, Shi YY, Zheng YX, Xiao SL, Wang H (2013) Development of oleanane-type triterpenes as a new class of HCV entry inhibitors. J Med Chem 56: 4300-4319. 
  • Zeng XY, Wang YP, Cantley J (2012) Oleanolic acid reduces hyperglycemia beyond treatment period with akt/foxo1-induced suppression of hepatic gluconeogenesis in type-2 diabetic mice. Plos One 7: e42115. 
  • Zhang W, Popovich DG (2009) Chemical and biological characterization of oleanane triterpenoids from soy. Molecules 14: 2959-2975. 
  • Zhou D, Jin H, Lin HB, Yang XM, Cheng YF, Deng FJ, Xu JP (2010) Antidepressant effect of the extracts from Fructus Akebiae. Pharmacol Biochem Behav 94: 488-495. 
  • Zwenger S, Basu C (2008) Plant terpenoids: applications and future potentials. Biotech Molecul Biol Rev 3: 001-007.
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