α,β-Unsaturated monoterpene acid glucose esters: Structural diversity, bioactivities and functional roles

Phytochemistry

Volumn 72, Issue 18, 2011, Pages 2259-2266

  Goodger, Jason Q D ^a   Woodrow, Ian E ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Carboxylic acid; Cuniloside; Eucalyptus; Glucosyl ester; Menthiafolic acid; Michael acceptor; Monoterpene glycoside; Monoterpenoid ester; Oleuropeic acid; Plant defence

Indexed keywords

EUCALYPTUS; MYRTACEAE;

EID: 80054938812     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.08.026     Document Type: Short Survey

References (73)

1. S. Amslinger The tunable functionality of α,β-unsaturated carbonyl compounds enables their differential application in biological systems ChemMedChem 5 2010 351 356
2. L. Ascensão, N. Marques, and M.S. Pais Peltate glandular trichomes of Leonatis leonurus leaves: ultrastructure and histochemical characterization of secretions Int. J. Plant Sci. 158 1997 249 258 (Pubitemid 27474102)
3. S. Begum, Farhat, and B.S. Siddiqui Chromenone glucosides acylated with monoterpene acids from the leaves of Eucalyptus camaldulensis var. obtusa Helv. Chim. Acta 94 2011 238 247
4. B. Bonnlander, B. Baderschneider, M. Messerer, and P. Winterhalter Isolation of two novel terpenoid glucose esters from Riesling wine J. Agric. Food Chem. 46 1998 1474 1478 (Pubitemid 128498791)
5. L. Boulekbache-Makhlouf, E. Meudec, M. Chibane, J.-P. Mazauric, S. Slimani, M. Henry, V. Cheynier, and K. Madani Analysis by high-performance liquid chromatography diode array detection mass spectrometry of phenolic compounds in fruit of Eucalyptus globulus cultivated in Algeria J. Agric. Food Chem. 58 2010 12615 12624
6. D.J. Bowles, E.K. Lim, B. Poppenberger, and F.E. Vaistij Glycosyltransferases of lipophilic small molecules Annu. Rev. Plant Biol. 57 2006 567 597 (Pubitemid 44061037)
7. I. ali, and A. Yürüker Anatolioside E: a new acyclic monoterpene glycoside from Viburnum orientale Helv. Chim. Acta 76 1993 2563 2569
8. I. ali, and A. Yürüker Anatoliosides: five novel acyclic monoterpene glycosides from Viburnum orientale Helv. Chim. Acta 76 1993 416 424
9. L. Caputi, E.K. Lim, and D.J. Bowles Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds Chem. - Eur. J. 14 2008 6656 6662
10. J. Crouzet, and D. Chassagne Glycosidically bound volatiles in plants R. Ikan, Naturally Occurring Glycosides 1999 John Wiley and Sons Chichester 225 274
11. V.M. Dembitsky Chemistry and biodiversity of the biologically active natural glycosides Chem. Biodiversity 1 2004 673 781
12. V.M. Dembitsky Astonishing diversity of natural surfactants: biologically active hemi- and monoterpenoid glycosides Lipids 41 2006 1 27
13. A.T. Dinkova-Kostova, and P. Talalay Relation of structure of curcumin analogs to their potencies as inducers of phase 2 detoxification enzymes Carcinogenesis 20 1999 911 914 (Pubitemid 29191875)
14. A.T. Dinkova-Kostova, and P. Talalay Direct and indirect antioxidant properties of inducers of cytoprotective proteins Mol. Nutr. Food Res. 52 2008 S128 S138
15. A. Fahn Secretory tissues in vascular plants New Phytol. 108 1988 229 257
16. A. Fahn Structure and function of secretory cells Adv. Bot. Res. 31 2000 37 75
17. X.S. Feng, Y. Qu, Z.H. Wu, L. Xu, D.S. Zhang, H.Y. Gao, and L.J. Wu Two new secoiridoid glucosides from Syrninga velutina Kom Chin. Chem. Lett. 20 2009 702 705
18. P.V. Gersbach The essential oil secretory structures of Prostanthera ovalifolis (Lamiaceae) Ann. Bot. 89 2002 255 260 (Pubitemid 34527449)
19. J.Q.D. Goodger, B. Cao, I. Jayadi, S.J. Williams, and I.E. Woodrow Non-volatile components of the essential oil secretory cavities of Eucalyptus leaves: discovery of two glucose monoterpene esters, cuniloside B and froggattiside A Phytochemistry 70 2009 1187 1194
20. J.Q.D. Goodger, A.M. Heskes, M.C. Mitchell, D.J. King, E.H. Neilson, and I.E. Woodrow Isolation of intact sub-dermal secretory cavities from Eucalyptus Plant Methods 6 2010 20
21. E. Gowan, B.A. Lewis, and R. Turgeon Phloem transport of antirrhinoside, an iridoid glycoside, in Asarina scandens (Scrophulariaceae) J. Chem. Ecol. 21 1995 1781 1788 (Pubitemid 3023432)
22. Z. Gu, H. Liang, H. Chen, Y. Xu, L. Yan, and W. Zhang Isolation and structure of camaldulenside from Eucalyptus camaldulensis var. pendula Blak. et Jacobs Acta Pharmacol. Sin. 35 2000 511 513
23. Q. Guo, and X. Yang Cypellocarpin C and other compounds from the fruits of Eucalyptus globulus Labill Biochem. Syst. Ecol. 34 2006 543 545
24. Z. Hakki, B. Cao, A.M. Heskes, J.Q.D. Goodger, I.E. Woodrow, and S.J. Williams Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus Carbohydr. Res. 345 2010 2079 2084
25. J.B. Harborne, and J.J. Corner Plant polyphenols 4. Hydroxycinnamic acid-sugar derivatives Biochem. J. 81 1961 242 250
26. T. Hase, T. Iwagawa, and K. Munesada A bitter monoterpene glucoside from Viburnum phlebotrichum Phytochemistry 21 1982 1435 1437
27. T. Hasegawa, F. Takano, T. Takata, M. Niiyama, and T. Ohta Bioactive monoterpene glycosides conjugated with gallic acid from the leaves of Eucalyptus globulus Phytochemistry 69 2008 747 753 (Pubitemid 351146588)
28. K. Holmberg Natural surfactants Curr. Opin. Colloid Interface Sci. 6 2001 148 159 (Pubitemid 32447576)
29. S.M. Hopkinson The chemistry and biochemistry of phenolic glycosides Q. Rev. - Chem. Soc. 23 1969 98 124
30. A.J. Hou, Y.Z. Liu, Z.W. Lin, and H.D. Sun Eucaglobulin, a new complex of gallotannin and monoterpene from Eucalyptus globulus Chin. Chem. Lett. 9 1998 541 543 (Pubitemid 128544542)
31. A.J. Hou, Y.Z. Liu, Z.W. Lin, and H.D. Sun Hydrolyzable tannins and related polyphenols from Eucalyptus globulus J. Asian Nat. Prod. Res. 2 2000 205 212
32. S. Hyodo, H. Etoh, N. Yamashita, K. Sakata, and K. Ina Structure of resinosides from Eucalyptus resinifera as repellents against the blue mussel, Mytilus edulis Biosci. Biotechnol. Biochem. 56 1992 138
33. R. Ikan Preface R. Ikan, Naturally Occurring Glycosides 1999 John Wiley and Sons Ltd. Chichester
34. H. Ito, M. Koreishi, H. Tokuda, H. Nishino, and T. Yoshida Cypellocarpins A-C, phenol glycosides esterified with oleuropeic acid, from Eucalyptus cypellocarpa J. Nat. Prod. 63 2000 1253 1257
35. N. Kasajima, H. Ito, T. Hatano, T. Yoshida, and M. Kaneda Cypellogins A, B and C, acylated flavonol glycosides from Eucalyptus cypellocarpa Chem. Pharmacol. Bull. 53 2005 1345 1347 (Pubitemid 41425638)
36. Y.K. Koleva, J.C. Madden, and M.T.D. Cronin Formation of categories from structure-activity relationships to allow read-across for risk assessment: toxicity of α,β-unsaturated carbonyl compounds Chem. Res. Toxicol. 21 2008 2300 2312
37. W. Kraus Investigation of biologically active natural products using online LC-bioassay, LC-NMR, and LC-MS techniques J. Toxicol. 22 2003 495 508 (Pubitemid 37523692)
38. L. Li, Y. Peng, L.J. Xu, T.N. Wu-Lan, R.B. Shi, and P.G. Xiao Chemical constituents from Ligustrum robustum Bl Biochem. Syst. Ecol. 38 2010 398 401
39. G. Liger-Belair, C. Cilindre, R.D. Gougeon, M. Lucio, I. Gebefugi, P. Jeandet, and P. Schmitt-Kopplin Unraveling different chemical fingerprints between a champagne wine and its aerosols Proc. Natl. Acad. Sci. USA 106 2009 16545 16549
40. E.K. Lim, C.J. Doucet, Y. Li, L. Elias, D. Worrall, S.P. Spencer, J. Ross, and D.J. Bowles The activity of Arabidopsis glycosyltransferases toward salicylic acid, 4-hydroxybenzoic acid, and other benzoates J. Biol. Chem. 277 2002 586 592 (Pubitemid 34952095)
41. B.R. Loveys, S.P. Robinson, J.J. Brophy, and E.K. Chacko Mango sapburn: components of fruit sap and their role in causing skin damage Funct. Plant Biol. 19 1992 449 457
42. K.M. Madyastha, and V. Srivatsan Biotransformations of a-terpineol in the rat: its effects on the liver microsomal cytochrome P-450 system Bull. Environ. Contam. Toxicol. 41 1988 17 25
43. D. Manns, and R. Hartmann Monoterpene glucosides from Cunila spicata Planta Med. 60 1994 467 469 (Pubitemid 24330779)
44. D. Meng, J. Wu, and W. Zhao Glycosides from Breynia fruticosa and Breynia rostrata Phytochemistry 71 2010 325 331
45. T. Nakanishi, N. Iida, Y. Inatomi, H. Murata, A. Inada, J. Murata, F.A. Lang, M. Iinuma, T. Tanaka, and Y. Sakagami A monoterpene glucoside and three megastigmane glycosides from Juniperus communis var. depressa Chem. Pharmacol. Bull. 53 2005 783 787 (Pubitemid 41327622)
46. O.P. Noté, A. Mitaine-Offer, T. Miyamoto, T. Paululat, D.E. Pegnyemb, and M. Lacille-Dubois Tetrapterosides A and B, two new oleanane-type saponins from Tetrapleura tetraptera Mag. Res. Chem. 47 2009 277 282
47. L. Panizzi, M.L. Scarpati, and C. Trogol Sulla oleuropeina Gazz. Chim. Ital. 95 1965 1279 1292
48. H. Pfander, and H. Stoll Terpenoid glycosides Nat. Prod. Rep. 8 1991 69 95
49. G. Regev-Shoshani, O. Shosheyov, I. Bilkis, and Z. Kerem Glycosylation of resveratrol protects it from enzymic oxidation Biochem. J. 374 2003 157 163 (Pubitemid 37046939)
50. P.B. Reichardt, T.P. Clausen, and J.P. Bryant Phenol glycosides in plant defense against herbivores Biologically Active Natural Products 1988 American Chemical Society 130 142
51. S. Reicheneder, and C. Unverzagt Synthesis of dimeric terpenoyl glycoside side chains from cytotoxic saponins Angew. Chem. 43 2004 4353 4357 (Pubitemid 39257419)
52. V. Renganathan, and K.M. Madyastha Linalyl acetate is metabolized by Pseudomonas incognita with the acetoxy group intanct Appl. Environ. Microbiol. 45 1983 6 15 (Pubitemid 13175272)
53. G.G. Santos, J.C.N. Alves, J.M. Rodilla, P.A. Duarte, A.M. Lithgow, and J.G. Urones Terpenoids and other constituents of Eucalyptus globulus Phytochemistry 44 1997 1309 1312 (Pubitemid 27130943)
54. M.L. Scarpati, and C. Trogolo 6-O-oleuropeoylsucrose from Olea europaea Tetrahedron Lett. 46 1966 5673 5674
55. E. Stahl-Biskup Monoterpene glycosides, state-of-the-art Flavour Frag. J. 2 1987 75 82
56. E. Stahl-Biskup, F. Intert, J. Holthuijzen, M. Stengele, and G. Schulz Glycosidically bound volatiles - a review 1986-1991 Flavour Frag. J. 8 1993 61 80
57. Y. Takeda, A. Takechi, T. Masuda, and H. Otsuka An acyclic monoterpene glucosyl ester from Lantana lilacia Planta Med. 64 1998 78 79 (Pubitemid 28060006)
58. M. Takido, K. Fukuhara, S. Yamanouchi, and S. Takahashi Phlebotrichin, a phenolic compound from the fresh leaves of Viburnum phlebotrichum Phytochemistry 22 1983 223 225
59. P. Talalay, M.J. De Long, and H.J. Prochaska Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis Proc. Natl. Acad. Sci. USA 85 1988 8261 8265
60. Q.G. Tan, X.H. Cai, T. Feng, and X.D. Luo Megastigmane-type compounds from Rotala rotundifolia Chin. J. Nat. Med. 7 2009 187 189
61. T. Tanahashi, A. Shimada, N. Nagakura, K. Inoue, M. Ono, T. Fujita, and C.C. Chen Structure elucidation of six acylated iridoid glucosides from Jasminum hemsleyi Chem. Pharm. Bull. (Tokyo) 43 1995 729 733
62. R. Taskova, N. Handjieva, D. Peev, and S. Popov Iridoid glucosides from three Veronica species Phytochemistry 49 1998 1323 1327 (Pubitemid 28524944)
63. W.W. Thomson, K.A. Platt-Aloia, and A.G. Endress Ultrastructure of oil gland development in the leaf of Citrus sinensis L Bot. Gaz. 137 1976 330 340
64. L.-W. Tian, Y.-J. Zhang, Y.-F. Wang, C.-C. Lai, and C.-R. Yang Eucalmaidins A-E, (+)-oleuropeic acid derivatives from the fresh leaves of Eucalyptus maideni J. Nat. Prod. 72 2009 1608 1611
65. L.-W. Tian, Y.-J. Zhang, C. Qu, Y.-F. Wang, and C.-R. Yang Phloroglucinol glycosides from the fresh fruits of Eucalyptus maideni J. Nat. Prod. 73 2010 160 163
66. G.W. Turner, J. Gershenzon, and R.B. Croteau Development of peltate glandular trichomes of peppermint Plant Physiol. 124 2000 665 679
67. Y. Vasserot, A. Arnaud, and P. Galzy Monoterpenol glycosides in plants and their biotechnological transformation Acta Biotechnol. 15 1995 77 95
68. A. Werker Function of essential oil-secreting glandular hairs in aromatic plants of the Lamiaceae - a review Flavour Frag. J. 8 1993 249 255
69. X. Yang, and Q. Guo Studies on chemical constituents in fruits of Eucalyptus globulus Zhongguo Zhong Yao Za Zhi 32 2007 496 500
70. X. Yang, Q. Guo, Y. Wang, W. Xu, L. Tian, and X. Tian Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 cell model Bioorg. Med. Chem. Lett. 17 2007 1107 1111 (Pubitemid 46177600)
71. M.S. Yates, M. Tauchi, F. Katsuoka, K.C. Flanders, K.T. Liby, T. Honda, G.W. Gribble, D.A. Johnson, J.A. Johnson, N.C. Burton, T.R. Guilarte, M. Yamamoto, M.B. Sporn, and T.W. Kensler Pharmacodynamic characterization of chemopreventive triterpenoids as exceptionally potent inducers of Nrf2-regulated genes Mol. Cancer Ther. 6 2007 154 162 (Pubitemid 46206678)
72. X.N. Zhong, H. Otsuka, T. Ide, E. Hirata, and Y. Takeda Hydroquinone diglycoside acyl esters from the leaves of Myrsine seguinii Phytochemistry 52 1999 923 927
73. K. Zou, Y. Zhao, G. Tu, J. Cui, Z. Jia, and R. Zhang Two diasteromeric saponins with cytotoxic activity from Albizia julibrissin Carbohydr. Res. 324 2000 182 188 (Pubitemid 30069463)