Volatile terpenoids of endophyte-free and infected peppermint (Mentha piperita L.): Chemical partitioning of a symbiosis

Microbial Ecology

Volumn 54, Issue 4, 2007, Pages 685-696

  Mucciarelli, Marco ^a   Camusso, Wanda ^a   Maffei, Massimo ^a   Panicco, Paola ^a   Bicchi, Carlo ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

TERPENE;

ARTICLE; CHEMISTRY; FUNGUS; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; MENTHA; MICROBIOLOGY; MYCELIUM; PLANT LEAF; PLANT ROOT; SYMBIOSIS; VOLATILIZATION;

FUNGI; MENTHA; MYCELIUM; PLANT LEAVES; PLANT ROOTS; SYMBIOSIS; TERPENES; VOLATILIZATION;

FUNGI; MENTHA X PIPERITA;

EID: 35448987281     PISSN: 00953628     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00248-007-9227-0     Document Type: Article

References (70)

1. Ahmad, A, Alam, M, Janardhanan, KK (2001) Fungal endophyte enhances biomass production and essential oil yield of east Indian lemongrass. Symbiosis 30: 275-285
2. Akiyama, K, Hayashi, H (2002) Arbuscular mycorrhizal fungus-promoted accumulation of two new triterpenoids in cucumber roots. Biosci Biotechnol Biochem 66: 762-769
3. Akiyama, K, Matsuzaki, K, Hayashi, H (2005) Plant sesquiterpenes induce hyphal branching in arbuscular mycorrhizal fungi. Nature 435: 824-827
4. Augusto, F, Valente, ALP (2002) Applications of solid-phase microextraction to chemical analysis of live biological samples. TrAC, Trends Anal Chem 21: 428-438
5. Bauch, J, Puls, J, Klupsch, R, Vogel, C (2004) Biological and chemical characteristics of included sapwood of Juniperus virginiana L. Holzforschung 58: 74-81
6. Bertea, CM, Maffei, M, Schalk, M, Karp, F, Croteau, R (2001) Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene. Arch Biochem Biophys 390: 279-286
7. Besserer, A, Puech-Pages, V, Kiefer, P, Gomez-Roldan, V, Jauneau, A, Roy, S, Portais, JC, Roux, C, Becard, G, Sejalon-Delmas, N (2006) Strigolactones stimulate arbuscular mycorrhizal fungi by activating mitochondria. PloS Biol 4: 1239-1247
8. Bicchi, C, Panero, OM, Pellegrino, GM, Vanni, AC (1997) Characterization of roasted coffee and coffee beverages by solid phase microextraction Gas chromatography and principal component analysis. J Agric Food Chem 45: 4680-4686
9. Bicchi, C, D Amato, A, Rubiolo, P (1999) Cyclodextrin derivatives as chiral selectors for direct gas chromatographic separation of enantiomers in the essential oil, aroma and flavour fields. J Chromatogr A 843: 99-121
10. Bicchi, C, Cordero, C, Iori, C, Rubiolo, P, Sandra, P (2000) Headspace sorptive extraction (HSSE) in the headspace analysis of aromatic and medicinal plants. HRC, J High Resolut Chromatogr 23: 539-546
11. Bicchi, C, Iori, C, Rubiolo, P, Sandra, P (2002) Headspace sorptive extraction (HSSE), stir bar sorptive extraction (SBSE), and solid phase microextraction (SPME) applied to the analysis of roasted arabica coffee and coffee brew. J Agric Food Chem 50: 449-459
12. Bicchi, C, Cordero, C, Liberto, E, Rubiolo, P, Sgorbini, B (2004) Automated head-space solid-phase dynamic extraction to analyse the volatile fraction of food matrices. J Chromatogr 1024: 217-226
13. Copetta, A, Lingua, G, Berta, G (2006) Effects of three AM fungi on growth, distribution of glandular hairs, and essential oil production in Ocimum basilicum L. var. Genovese. Mychorriza 16: 485-494
14. Davis, EM, Ringer, KL, McConkey, ME, Croteau, R (2005) Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint. Plant Physiol 137: 873-881
15. Demyttenaere, JCR, De Kimpe, N (2001) Biotransformation of terpenes by fungi study of the pathways involved. J Mol Catal B Enzym 11: 265-270
16. Demyttenaere, JCR, Morina RM, Sandra, P (2003) Monitoring and fast detection of mycotoxin-producing fungi based on headspace solid-phase microextraction and headspace sorptive extraction of the volatile metabolites. J Chromatogr A 985: 127-135
17. Demyttenaere, JCR, Vanoverschelde, J, De Kimpel, N (2004) Biotransformation of (R)-(+)- and (S)-(-)-citronellol by Aspergillus. J Chromatogr A 1027: 137-146
18. Espinosa-Garcia, FJ, Langenheim, JH (1991a) Effect of some leaf essential oil phenotypes in coastal redwood on the growth of several fungi with endophytic stages. Biochem Syst Ecol 19: 629-642
19. Espinosa-Garcia, FJ, Langenheim, JH (1991b) Effect of some leaf essential oil phenotypes from coastal redwood on growth of its predominant endophytic fungus, Pleuroplaconema sp. J Chem Ecol 17: 1837-1857
20. Fiedler, K, Schütz, E, Geh, S (2001) Detection of microbial organic compounds (MVOCs) produced by moulds on various materials. Int J Hyg Environ Health 201: 111-121
21. Gatenby, WA, Munday-Finch, SC, Wilkins, AL, Miles, CO (1999) Terpendole M, a novel indole-diterpenoid isolated from Lolium perenne infected with the endophytic fungus Neotyphodium lolii. J Agric Food Chem 47: 1092-1097
22. Giamperi, L, Fraternale, D, Ricci, D (2002) The in vitro action of essential oils on different organisms. J Essent Oil Res 14: 312-318
23. Gupta, ML, Prasad, A, Ram, M, Kumar, S (2002) Effect of the vesicular-arbuscular mycorrhizal (VAM) fungus Glomus fasciculatum on the essential oil yield related characters and nutrient acquisition in the crops of different cultivars of menthol mint (Mentha arvensis) under field conditions. Bioresour Technol 81: 77-79
24. Hans, J, Hause, B, Strack, D, Walter, MH (2004) Cloning, characterization, and immunolocalization of a mycorrhiza-inducible 1-deoxy-d-xylulose 5-phosphate reductoisomerase in arbuscule-containing cells of maize. Plant Physiol 134: 614-624
25. Harborne, JB (1991) Recent advances in the ecological chemistry of plant terpenoids. In: Harborne, JB, Tomas-Barberan, FA (Eds.) Ecological Chemistry and Biochemistry of Plant Terpenoids, Clarendon Press, Oxford, pp 399-426
26. Ishikawa, NK, Yamaji, K, Tahara, S, Fukushi, Y, Takahashi, K (2000) Highly oxidized cuparene-type sesquiterpenes from a mycelial culture of Flammulina velutipes. Phytochemistry 54: 777-782
27. Ishikawa, NK, Fukushi, Y, Yamaji, K, Tahara, S, Takahashi, K (2001) Antimicrobial cuparene-type sesquiterpenes, enokipodins C and D, from a mycelial culture of Flammulina velutipes. J Nat Products 64: 932-934
28. Ismailialaoui, M, Benjilali, B, Buisson, D, Azerad, R (1992) Biotransformation of terpenic compounds by fungi. 1. Metabolism of R-(+)-pulegone. Tetrahedron Lett 33: 2349-2352
29. Jurc, D, Bojovic, S, Jurc, M (1999) Influence of endogenous terpenes on growth of three endophytic fungi from the needles of Pinus nigra Arnold. Phyton Ann Rei Bot 39: 225-229
30. Kapoor, R, Giri, B, Mukerji, KG (2002a) Mycorrhization of coriander (Coriandrum sativum L) to enhance the concentration and quality of essential oil. J Sci Food Agric 82: 339-342
31. Kapoor, R, Giri, B, Mukerji, KG (2002b) Glomus macrocarpum: a potential bioinoculant to improve essential oil quality and concentration in Dill (Anethum graveolens L.) and Carum (Trachyspermum ammi Linn.) Sprague. World J Microbiol Biotechnol 18: 459-463
32. Langenheim, JH (1994) Higher plant terpenoids-a phytocentric overview of their ecological roles. J Chem Ecol 20: 1223-1280
33. Madyastha, KM, Thulasiram, HV (1999) Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis. J Agric Food Chem 47: 1203-1207
34. Maffei, M (1990) Plasticity and genotypic variation in some Mentha x verticillata hybrids. Biochem Syst Ecol 18: 493-502
35. Maffei, M, Mucciarelli, M, Scannerini, S (1994) Are leaf area index (LAI) and flowering related to oil productivity in peppermint? Flavour Fragr J 9: 119-124
36. Maffei, M, Scannerini, S (2000) UV-B effect on photomorphogenesis and essential oil composition in peppermint (Mentha piperita L.). J Essent Oil Res 12: 523-529
37. Maffei, M, Camusso, W, Sacco, S (2001) Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential. Phytochemistry 58: 703-707
38. Mahmoud, SS, Croteau, RB (2003) Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase. Proc Natl Acad Sci USA 100: 14481-14486
39. Maier, W, Hammer, K, Dammann, U, Schulz, B, Strack, D (1997) Accumulation of sesquiterpenoid cyclohexenone derivatives induced by an arbuscular mycorrhizal fungus in members of the Poaceae. Planta 202: 36-42
40. McGarvey, DJ, Croteau, R (1995) Terpenoid metabolism. Plant Cell 7: 1015-1026
41. Miyazawa, M, Kawazoe, H, Hyakumachi, M (2002) Biotransformation of l-menthol by soil-borne plant pathogenic fungi (Rhizoctonia solani). J Chem Technol Biotechnol 77: 21-24
42. Mucciarelli, M, Camusso, W, Bertea, CM, Bossi, S, Maffei, M (2001) Effect of (+)-pulegone and other oil components of Mentha x piperita on cucumber respiration. Phytochemistry 57: 91-98
43. Mucciarelli, M, Scannerini, S, Bertea, CM, Maffei, M (2002) An ascomycetous endophyte isolated from Mentha piperita L.: biological features and molecular studies. Mycologia 94: 28-39
44. Mucciarelli, M, Scannerini, S, Bertea, CM, Maffei, M (2003) In vitro and in vivo peppermint (Mentha piperita) growth promotion by nonmycorrhizal fungal colonization. New Phytol 158: 579-591
45. Murashige, T, Skoog, F (1962) A revised medium for rapid growth and byoassays with tobacco tissue cultures. Physiol Plant 15: 473-497
46. Nabeta, K, Kawakita, K, Yada, Y, Okuyama, H (1993) Biosynthesis of sesquiterpenes from deuterated mevalonates in Perilla callus. Biosci Biotechnol Biochem 57: 792-798
47. Napierala-Filipiak, A, Werner, A, Mardarowicz, M, Gawdzik, J (2002) The effects of heavy metals, content of nutrients and inoculation with mycorrhizal fungi on the level of terpenoids in roots of Pinus sylvestris seedlings. Acta Physiol Plant 24: 137-143
48. Oumzil, H, Ghoulami, S, Rhajaoui, M, Ilidrissi, A, Fkih-Tetouani, S, Faid, M, Benjouad, A (2002) Antibacterial and antifungal activity of essential oils of Mentha suaveolens. Phytotherapy Res 16: 727-731
49. Packiyasothy, EV, Kyle, S (2002) Antimicrobial properties of some herb essential oils. Food Aust 54: 384-387
50. Pandey, RR, Arora, DK, Dubey, RC (1993) Antagonistic interactions between fungal pathogens and phylloplane fungi of guava. Mycopathologia 124: 31-39
51. Pichersky, E, Gershenzon, J (2002) The formation and function of plant volatiles: perfumes for pollinator attraction and defense. Curr Opin Plant Biol 5: 237-243
52. Raffa, KF, Smalley, EB (1995) Interaction of pre-attack and induced monoterpene concentrations in host conifer defense against bark beetle fungal complexes. Oecologia 102: 285-295
53. Riu-Aumatell, M, Castellari, M, Lopez-Tamames, E, Galassi, S, Buxaderas, S (2004) Characterisation of volatile compounds of fruit juices and nectars by HS/SPME and GUMS. Food Chem 87: 627-637
54. Sassa, T, Kenmoku, H, Sato, M, Murayama, T, Kato, N (2003) (+)-Menthol and its hydroxy derivatives, novel fungal monoterpenols from the fusicoccin-producing fungi, Phomopsis amygdali F6A and Niigata 2. Biosci Biotechnol Biochem 67: 475-479
55. Sati, S, Mathela, CS (2005) Essential oil composition of Valeriana hardwickii var. arnottiana from the Himalayas. Flavour Fragr J 20: 299-301
56. Scannerini, S, Fusconi, A, Mucciarelli, M (2001) The effect of endophytic fungi on host plant morphogenesis. In: Seckbach, J (Ed.) Symbiosis, Cellular Origin and Life in Extreme Habitats, Kluwer Academic Publishers, Dordrecht, pp 427-447
57. Schardl, CL (1996) Interactions of grasses with endophytic Epichloë species and hybrids. In: Stacey, G, Keen, NT (Eds.) Plant Microbe Interactions, Chapman Hall, New York, pp 107-140
58. Schulz, B, Rommert, AK, Dammann, U, Aust, HJ, Strack, D (1999) The endophyte-host interaction: a balanced antagonism? Mycol Res 103: 1275-1283
59. Schulz, B, Boyle, C, Draeger, S, Rommert, AK, Krohn, K (2002) Endophytic fungi: a source of novel biologically active secondary metabolites. Mycol Res 106: 996-1004
60. Stinson, M, Ezra, D, Hess, WM, Sears, J, Strobel, G (2003) An endophytic Gliocladium sp. of Eucryphia cordifolia producing selective volatile antimicrobial compounds. Plant Sci 165: 913-922
61. Strobel, GA, Dirkse, E, Sears, J, Markworth, C (2001) Volatile antimicrobials from Muscodor albus, a novel endophytic fungus. Microbiology 7: 2943-2950
62. Takahashi, H, Noma, Y, Toyota, M, Asakawa, Y (1994) Biotransformation of (-)- and (+)-neomenthols and isomenthol by Aspergillus niger. Phytochemistry 35: 1465-1467
63. Tamasloukht, M, Sejalon-Delmas, N, Kluever, A, Jauneau, A, Roux, C, Becard, G, Franken, P (2003) Root factors induce mitochondrial-related gene expression and fungal respiration during the developmental switch from asymbiosis to presymbiosis in the arbuscular mycorrhizal fungus Gigaspora rosea. Plant Physiol 131: 1468-1478
64. Toyota, M, Koyama, H, Asakawa, Y (1997) Sesquiterpenoids from the three Japanese liverworts Lejeunea aquatica, L. flava and L. japonica. Phytochemistry 46: 145-150
65. van Dyk, MS, van Rensburg, E, Rensburg, IPB, Moleleki, N (1998) Biotransformation of monoterpenoid ketones by yeasts and yeast-like fungi. J Mol Catal B Enzym 5: 149-154
66. Viiri, H, Annila, E, Kitunen, V, Niemela, P (2001) Induced responses in stilbenes and terpenes in fertilized Norway spruce after inoculation with blue-stain fungus, Ceratocystis polonica. Trees 15: 112-122
67. Werner, A, Napierala-Filipiak, A, Mardarowicz, M, Gawdzik, J (2004) The effect of two substrates differing in the amount of toxic metals and nutrients on the content of volatile organic compounds in roots of Pinus sylvestris. Acta Physiol Plant 26: 187-196
68. Yue, Q, Miller, CJ, White, JF Jr, Richardson, MD (2000) Isolation and characterization of fungal inhibitors from Epichloë festucae. J Agric Food Chem 48: 4687-4962
69. Yue, Q, Wang, C, Gianfagna, TJ, Meyer, WA (2001) Volatile compounds of endophyte-free and infected tall fescue (Festuca arundinacea Schreb.). Phytochemistry 58: 935-941
70. Zhang, Z, Pawliszyn, J (1993) Headspace solid-phase microextraction. Anal Chem 65: 1843-1852