Triterpenoids from Gymnema sylvestre and their pharmacological activities

Molecules

Volumn 19, Issue 8, 2014, Pages 10956-10981

  Di Fabio, Giovanni ^a   Romanucci, Valeria ^a   De Marco, Anna ^a   Zarrelli, Armando ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Gymnema sylvestre; Oleanes; Pharmacological activities; Phytochemistry; Triterpenoids

Indexed keywords

PLANT EXTRACT; TRITERPENE;

CHEMISTRY; GYMNEMA SYLVESTRE; MEDICINAL PLANT; METABOLISM; METABOLOME; SECONDARY METABOLISM;

GYMNEMA SYLVESTRE; METABOLOME; PLANT EXTRACTS; PLANTS, MEDICINAL; SECONDARY METABOLISM; TRITERPENES;

EID: 84906679707     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules190810956     Document Type: Review

References (67)

1. Oksman-Caldentey, K.M.; Inze, D. Plant cell factories in the post-genomic era: New ways to produce designer secondary metabolites. Trends Plant Sci. 2004, 9, 433-440.
2. Duradeva, N.; Pichersky, E. Metabolic engineering of plant volatiles. Curr. Opin. Biotech. 2008, 19, 1-9.
3. Picman, J.; Picman, A.K. Autotoxicity in Parthenium hysterophorus and its possible role in control of germination. Biochem. Sys. Ecol. 1984, 12, 287-292.
4. Inderjit; Keating, K.I. Allelopathy: Principles, procedures, processes, and promises for biological control. Adv. Agron. 1999, 67, 141-231.
5. Montesinos, E. Development, registration and commercialization of microbial pesticides for plant protection. Int. Microbiol. 2003, 6, 245-252.
6. Dayan, F.E.; Duke, S.O. Biobased herbicides. In Proceedings of the 233rd ACS National Meeting, Chicago, IL, USA, 25-29 March 2007; AGRO-200.
7. Macias, F.A.; Molinillo, J.M.G.; Varela, R.M.; Galindo, J.C.G. Allelopathy - a natural alternative for weed control. Pest Manag. Sci. 2007, 63, 327-348.
8. Liu, A.G.; Cui, Y.; Zhu, Y.D.; Gao, W.; Kong, C.H.; Xu, X.H. Allelochemicals and mechanism of weed-suppressing activity from allelopathic rice. In Proceedings of the International Forum on Green Chemical Science & Engineering and Process Systems Engineering, Tianjin, China, 8-10 October 2006; pp. 546-549.
9. Kaufman, P.B.; Cseke, L.J.; Warber, S.; Duke, J.A.; Brielmann, H.L. Natural Products from Plants; CRC Press: Boca Raton, FL, USA 1999.
10. Fiehn, O. Metabolomics-the link between genotypes and phenotypes. Plant Mol. Biol. 2002, 48, 155-171.
11. Dixon, R.A. Natural products and plant disease resistance. Nature 2001, 411, 843-847.
12. Canter, P.H.; Thomas, H.; Ernst, E. Bringing medicinal plants into cultivation: Opportunities and challenges for biotechnology. Trends Biotechnol. 2005, 23, 180-185.
13. Rates, S.M.K. Plants as sources of drugs. Toxicon 2001, 39, 603-613.
14. Raskin, I.; Ribnicky, D.M.; Komarnytsky, S.; Ilic, N.; Poulev, A.; Borisjuk, N.; Brinker, A.; Moreno, D.A.; Ripoll, C.; Yakoby, N.; et al. Plants and human health in the twenty-first century. Trends Biotechnol. 2002, 20, 522-531.
15. Balandrin, M.F.; Klocke, J.A. Medicinal, Aromatic and Industrial Materials from Plants. In Biotechnology in Agriculture and Forestry; Springer Verlag: Berlin, Germany, 1981; Volume 40, pp. 1-35.
16. Newman, D.J.; Cragg, G.M. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod. 2008, 70, 461-477.
17. Dzubak, P.; Hajduch, M.; Vydra, D.; Hustova, A.; Kvasnica, M.; Biedermann, D.; Markova, L.; Urban, M.; Sarek, A. Pharmacological activities of natural triterpenoids and their therapeutic implications. J. Nat. Prod. Rep. 2006, 23, 394-411.
18. Dewick, P.M. Medicinal Natural Products, 3rd Ed.; John Wiley & Sons Ltd: Chichester, West Sussex, UK, 2009; p. 187.
19. Breitmaier, E. Terpenes; Wiley-VCH, Weinheim, Germany, 2006.
20. Gills, P.M., Jr. Revised section F: Natural products and related compounds. Pure Appl. Chem. 1999, 71, 587-593.
21. Fraga, B.M. Natural sesquiterpenoids. Nat. Prod. Rep. 2008, 25, 1180-1209.
22. Hanson, J.R. Diterpenoids. Nat. Prod. Rep. 2007, 24, 1332-1341.
23. Connolly, J.D.; Hill, R.A. Triterpenoids. Nat. Prod. Rep. 2008, 25, 794-830.
24. Lois, L.M.; Campos, N.; Putra, S.R.; Danielsen, K.; Rohmer, M.; Boronat, A. Cloning and characterization of a gene from Escherichia coli encoding and transketolase-like enzyme that catalyze the synthesis of D-1-deoxyxylulose 5-phosphate, a common precursor for isoprenoid, thiamin and pyridoxol biosynthesis. Proc. Natl. Acad. Sci. USA 1998, 95, 2015-2110.
25. Gildemeister, E.; Hoffmann, F. In Die ätherischen Öle, 4th ed.; Akademie Verlag: Berlin, Germany, 1960; pp. 1-7.
26. Sandermann, W. Naturharze, Terpentinöl, Tallöl; Springer Verlag: Berlin, Germany, 1960.
27. Osbourn, A.E. Saponin and olant defence - a soap story. Trends Plant Sci. 1996, 1, 4-9.
28. Osbourn, A.E. Preformed antimicrobial compound and plant defense against fungal attack. Plant Cell 1996, 8, 1821-1831.
29. Harmatha, J. Chemo-ecological role spirostanol saponins in the interaction between plants and insect. In Saponins in Food, Feedstuffs and Medicinal Plants; Olezsek, W., Marston, A., Eds.; Kluwer Academic: Dordrecht, The Netherlands, 2000.
30. Yoshikawa, K.; Nakagawa, M.; Yamamoto, R.; Arihara, S.; Matsuura, K. Studies on taste modifiers. II. Purification and structure determination of gymnemic acids, antisweet active principle from Gymnema sylvestre leaves. Tetrahedron Lett. 1989, 30, 1547-1550.
31. Yoshikawa, K.; Amimoto, K.; Arihara, S.; Matsuura, K. Structure studies of new antisweet constituents from Gymnema sylvestre. Tetrahedron Lett. 1989, 30, 1103-1106.
32. Kazujo, Y.; Kayoko, A.; Shigenobu, A.; Kouji, M. Gymenmic acids V, VI and VII from Gur-ma, the leaves of Gymnema sylvestre R. Br. Chem. Pharm. Bull. 1989, 37, 852-854.
33. Kurihara, K. Inhibition of cyclic 3',5'-nucleotide phosphodiesterase in bovine taste papillae by bitter taste stimuli. Febs Lett. 1972, 27, 279-281.
34. Yoshikawa, K.; Arihara, S.; Matsuura, K. A new type of antisweet principles occurring in Gymnema sylvestre. Tetrahedron Lett. 1991, 32, 789-792.
35. Yoshikawa, K.; Nakagawa, M.; Yamamoto, R.; Arihara, S.; Matsuura, K. Antisweet natural products. V. Structures of gymnemic acids VIII-XII from Gymnema sylvestre R. Br. Chem. Pharm. Bull. 1992, 40, 1779-1782.
36. Yoshikawa, K.; Kondo, Y.; Arihara, S.; Matsuura, K. Antisweet natural products. IX. Structures of gymnemic acids XV-XVIII from Gymnema sylvestre R. Br. Chem. Pharm. Bull. 1993, 41, 1730-1732.
37. Masuyuki, Y.; Toshiyuki, M.; Hisashi, M. Medicinal foodstuffs. X. Structures of new triterpene glycosides, Gymnemosides-c, -d, -e, and -f, from the leaves of Gymnema sylvestre R. Br.: Influence of Gymnema glycosides on glucose uptake in rat small intestinal fragmentes. Chem. Pharm. Bull. 1997, 45, 2034-2038.
38. Kimura, I.; Zasshi, Y. Medical benefits of using natural compounds and their derivatives having multiple pharmacological actions. Actions 2006, 126, 133-143.
39. Henkel, T.; Brunne, R.M.; Muller, H.M.; Reichel, F. Statistical investigation into the structural complementary of natural products and synthetic compound. Angew. Chem. Int. 1999, 38, 643-647.
40. Eggersdofer, M. Terpenes. In Ullmann's Encyclopedia of Industrial Chemistry, Electronic Release; Wiley-VCH, Weinheim, Germany, 2005.
41. Duke, S.O.; Romagni, J.G.; Dayan, F.E. Natural products as sources for new mechanisms of herbicidal action. Crop Prot. 2000, 19, 583-589.
42. Catchpole, O.J.; von Kamp, J.C.; Grey, J.B. Extraction of squalene from shark liver oil in a packed column using supercritical carbon dioxide. Ind. Eng. Chem. Res. 1997, 36, 4318-4324.
43. Pietsch, A.; Jaeger, P. Concentration of squalene from shark liver oil by short-path distillation. Eur. J. Lipid. Sci. Technol. 2007, 109, 1077-1082.
44. Eisenreich, W.; Rohdich, F.; Bacher, A. Deoxyxylulose phosphate pathway to terpenoids. Trends Plant Sci. 2001, 6, 78-84.
45. Stocklin, W. Gymnemagenin, vermutliche struktur Glykoside und Aglykone, 289. Mitteilung. Helv. Chim. Acta 1967, 50, 491-503.
46. Yoshikawa, M.; Murakami, T.; Kadoya, M.; Li, Y.; Murakami, N.; Yamahara, J.; Matsuda, H. Medicinal foodstuffs. IX. The inhibitors of glucose absorption from the leaves of Gymnema sylvestre R. Br. (Asclepiadaceae): Structures of gymnemosides a and b. Chem. Pharm. Bull. 1997, 45, 1671-1676.
47. Murakami, N.; Murakami, T.; Kadoya, M.; Matsuda, H.; Yamahara, J.; Yoshikawa, M. New hypoglycemic constituents in "gymnemic acid" from Gymnema sylvestre. Chem. Pharm. Bull. 1996, 44, 469-471.
48. Nishino, H.; Nishino, A.; Takayasu, J.; Hasegawa, T.; Iwashima, A.; Hirabayashi, K.; Iwata, S.; Shibata, S. Inhibition of the tumor-promoting action of 12-O-tetradecanoylphorbol 13-acetate by some oleanane-type triterpenoid compounds. Cancer Res. 1988, 48, 5210-5521.
49. Shibata, S. Antitumor-promoting and anti-inflammatory activities of licorice principles and their modified compounds. In ACS Symposium Series Food Phytochemicals for Cancer Prevention II; American Chemical Society: Washington, DC, USA, 1994; Volume 547, pp. 308-321.
50. Nishino, H.; Shibata, S.; Hirabayashi, K.; Iwata, S. Antitumor-promoting activity of glycyrrhetinic acid-related compounds. Kyoto-Furitsu Ika Daigaku Zasshi 1986, 95, 1563-1566.
51. Satomi, Y.; Nishino, H.; Shibata, S. Glycyrrhetinic and related compounds induce G1 arrest and apoptosis in human hepatocellular carcinoma HepG2. Anticancer Res. 2005, 25, 4043-4047.
52. Ohigashi, H.; Takamura, H.; Koshimizu, H.; Tokuda, H.; Ito, Y. Search for possible antitumor promoters by inhibition of 12-O-tetradecanoylphorbol-13- acetate-induced Epstein-Barr virus activation. Ursolic acid and oleanolic acid from an anti-inflammatory. Cancer Lett. 1986, 30, 143-151.
53. Lee, J.S.; Yoo, H.S.; Suh, Y.G.; Jung, J.K.; Kim J.W. Structure-activity relationship of pentacylic triterpene esters from Uncaria rhynchophylla as inhibitors of phospholipase Cγ1. Planta Med. 2008, 74, 1481-1487.
54. Skehan, P.; Stroreng, R.; Scudiero, D.; Monks, A.; Mcmahon, J.; Vistica, D.; Warren, J.T.; Bokesch, H.; Kenney, S.; Boyd, M.R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Nat. Cancer 1990, 82, 1107-1112.
55. Lee, I.K.; Choi, S.U.; Lee, K.R. Triterpene saponins from Pleurospermum kamtschaticum and their biological activity. Chem. Pharm. Bull. 2012, 60, 1011-1018.
56. Liu, H.M.; Kiuchi, F.; Tsuda, Y. Isolation and structure elucidation of gymnemic acids, antisweet principles of Gymnema sylvestre. Chem. Pharm. Bull. 1992, 40, 1366-1375.
57. Yoshisuke, T.; Fumiyuki, K.; Hong-Min, L. Establishment of the structure of gymenmagenin by X-ray analysis and the structure of deacylgymnemic acid. Tetrahedron Lett. 1989, 30, 361-362.
58. Zarrelli, A.; Ladhari, A.; Haouala, R.; di Fabio, G.; Previtera, L.; DellaGreca, M. New acylated oleane and lupane triterpenes from Gymnema sylvestre. Helv. Chim. Acta 2013, 96, 2200-2206.
59. Sahu, N.P.; Mahato, S.B.; Sarkar, S.K.; Poddar, G. Triterpenoid saponins from Gymnema sylvestre. Phytochemistry 1996, 41, 1181-1185.
60. Zarrelli, A.; Della Greca, M.; Ladhari, A.; Haouala, R.; Previtera, L. New Triterpenes from Gymnema sylvestre. Helv. Chim. Acta 2013, 96, 1036-1045.
61. Sarkar, S.K. Potential Hypoglycemic and Antihyperglycemic Triterpenold Saponins from Gymnema sylvestre. In Proceedings of 210th ACS National Meeting, Chicago, IL, USA, August 1995; In Book of Abstracts; AGFD-239.
62. García-Granados, A.; Lopez, P.E.; Melguizo, E.; Parra, A.; Simeo, Y. Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A. J. Org. Chem. 2007, 72, 3500-3509.
63. Spasov, A.A.; Samokhina, M.P.; Bulanov, A.E. Medicinal plants antidiabetic properties of Gymnema sylvestre (a review). Pharm. Chem. J. 2008, 42, 29-31.
64. Ye, W.C.; Liu, X.; Zhao, S.X.; Che, C.T. Triterpenes from Gymnema sylvestre growing in China. Biochem. Syst. Ecol. 2001, 29, 1193-1195.
65. Sugihara, Y.; Nojima, H.; Matsuda, H.; Murakami, T.; Yoshikawa, M.; Kimura, I. Antihyperglycemic effects of gymnemic acid IV, a compound derived from Gymnema sylvestre leaves in streptozotocin-diabetic mice. J. Asian Nat. Prod. Res. 2000, 2, 321-327.
66. Maser, E.; Blum, A. Selektiver Inhibitor der 11β-Hydroxysteroid Dehydrogenase. DE 102004040690 A1, 2 March 2006.
67. Shibata, S.; Nishino, H.; Hirabayashi, K.; Iwata, S. Epicarcinogen Inhibitors Containing Oleanane Triterpenes. JP 63057519 A, 12 March 1988.