Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter December 7, 2021

An update on the progress of microbial biotransformation of commercial monoterpenes

  • Ruchika Mittal , Gauri Srivastava and Deepak Ganjewala ORCID logo EMAIL logo


Monoterpenes, a class of isoprenoid compounds, are extensively used in flavor, fragrance, perfumery, and cosmetics. They display many astonishing bioactive properties of biological and pharmacological significance. All monoterpenes are derived from universal precursor geranyl diphosphate. The demand for new monoterpenoids has been increasing in flavor, fragrances, perfumery, and pharmaceuticals. Chemical methods, which are harmful for human and the environment, synthesize most of these products. Over the years, researchers have developed alternative methods for the production of newer monoterpenoids. Microbial biotransformation is one of them, which relied on microbes and their enzymes. It has produced many new desirable commercially important monoterpenoids. A growing number of reports reflect an ever-expanding scope of microbial biotransformation in food and aroma industries. Simultaneously, our knowledge of the enzymology of monoterpene biosynthetic pathways has been increasing, which facilitated the biotransformation of monoterpenes. In this article, we have covered the progress made on microbial biotransformation of commercial monoterpenes with a brief introduction to their biosynthesis. We have collected several reports from authentic web sources, including Google Scholar, Pubmed, Web of Science, and Scopus published in the past few years to extract information on the topic.

Corresponding author: Deepak Ganjewala, Amity Institute of Biotechnology, Amity University Uttar Pradesh, Sector-125, Noida 201303, UP, India, E-mail:


The corresponding author of the manuscript would like to thank Council of Scientific and Industrial Research (CSIR) New Delhi Government of India for providing financial support for our ongoing research program on microbial biotransformation of alkaloids. Also, I would like to thank founder Dr. Ashok K. Chauhan and Chancellor Mr. Atul Chauhan, Amity University Uttar Pradesh, Noida India, for providing necessary support and facilities.

  1. Author contribution: Ms. Ruchika Mittal and Gauri Srivastava are PhD scholars and working on biotransformation of alkaloids and monoterpenes. Both have surveyed and collected literature, and typewrite the manuscript. Deepak Ganjewala: Analyses of research reports, interpretation, execution and manuscript writing.

  2. Research funding: None declared.

  3. Conflict of interest statement: All authors have no conflict of interest.

  4. Consent for publication: All authors are agreed for submission of this paper.


1. Tholl, D. Biosynthesis and biological functions of terpenoids in plants. Adv Biochem Eng Biotechnol 2015;148:63–106. in Google Scholar

2. Pichersky, E, Raguso, AR. Why do plants produce so many terpenoid compounds? New Phytol 2018;220:692–702. in Google Scholar

3. Heiling, S, Schuman, CM, Schoettner, M, Mukerjee, P, Berger, B, Schneider, B, et al.. Jasmonate and hsystemin regulate key malonylation steps in the biosynthesis of 17-hydroxygeranyllinalool diterpene glycosides, anabundant and effective direct defense against herbivores in Nicotiana attenuata. Plant Cell 2010;22:273–92. in Google Scholar

4. Keeling, IC, Bohlmann, J. Genes, enzymes and chemicals of terpenoid diversity in the constitutive and induced defence of conifers against insects and pathogens. New Phytol 2006;170:657–75. in Google Scholar

5. Ganjewala, D, Gupta, KA. Lemongrass (Cymbopogon flexuosus Steud.) wats essential oil: overview and biological activities. Recent Prog Med Plants 2013;37:235–71.Search in Google Scholar

6. Bauer, K, Garbe, D, Surburg, H. Common fragrance and flavor materials: preparation, properties and uses. New York, USA: John Wiley and Sons; 2008.Search in Google Scholar

7. Ganjewala, D, Gupta, KA, Muhury, R. An update on bioactive potential of a monoterpene aldehyde citral. J Biol Active Prod Nat 2012;2:186–99. in Google Scholar

8. Lange, MB, Ahkami, A. Metabolic engineering of plant monoterpenes, sesquiterpenes and diterpenes-current status and future opportunities. Plant Biotechnol J 2013;11:169–96. in Google Scholar

9. Yadav, JV, Mey De, M, Lim Giaw, C, Kumaran, PA, Stephanopoulos, G. The future of metabolic engineering and synthetic biology: towards a systematic practice. Metab Eng 2012;14:233–41. in Google Scholar

10. Korman, PT, Opgenorth, HP, Bowie, UJ. A synthetic biochemistry platform for cell free production of monoterpenes from glucose. Nat Commun 2017;8:1–8. in Google Scholar

11. Hegazy, ME, Mohamed, TA, El Shamy, AI, Abou-El-Hamd, HM, Mahalel, UA, Reda, EH, et al.. Microbial biotransformation as a tool for drug development based on natural products from mevalonic acid pathway: a review. J Adv Res 2015;6:17–33. in Google Scholar

12. Shalit, M, Guterman, I, Volpin, H, Bar, E, Tamari, T, Menda, N, et al.. Volatile ester formation in roses identification of an acetyl-coenzyme A. Geraniol/citronellol acetyltransferase in developing rose petals. Plant Physiol 2003;131:1868–76. in Google Scholar

13. Sharmeen, JB, Mahomoodally, FM, Zengin, G, Maggi, F. Essential oils as natural sources of fragrance compounds for cosmetics and cosmeceuticals. Molecules 2021;26:666. in Google Scholar

14. Guterman, I, Masci, T, Chen, X, Negre, F, Pichersky, E, Dudareva, N, et al.. Generation of phenylpropanoid pathway-derived volatiles in transgenic plants: rose alcohol acetyltransferase produces phenylethyl acetate and benzyl acetate in Petunia flowers. Plant Mol Biol 2006;60:555–63. in Google Scholar

15. Pichersky, E, Dudareva, D. Scent engineering: toward the goal of controlling how flowers smell. Trends Biotechnol 2007;25:105–10. in Google Scholar

16. Lucker, J, Bouwmeester, JH, Schwab, W, Blaas, J, Plas Der Van, LHW, Verhoeven, AH. Expression of Clarkia S-linalool synthase in transgenic Petunia plants results in the accumulation of S-linalyl-β-d-glucopyranoside. Plant J 2001;27:315–24. in Google Scholar

17. Nogues, I, Loreto, F. Regulation of isoprene and monoterpene emission in isoprenoid synthesis in plants and microorganisms. New York: New Concepts and Experimental Approaches Springer; 2013:139–53 pp.10.1007/978-1-4614-4063-5_10Search in Google Scholar

18. Rohmer, M, Knani, M, Simonin, P, Sutter, B, Sahm, H. Isoprenoid biosynthesis in bacteria: a novel pathway for early steps leading to isopentenyl diphosphate. Biochem J 1993;295:517–24. in Google Scholar

19. Rodriguez-Concepcion, M, Boronat, A. Elucidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis in bacteria and plastids a metabolic milestone achieved through genomics. Plant Physiol 2002;130:1079–89. in Google Scholar

20. Mahmoud, SS, Croteau, BR. Strategies for transgenic manipulation of monoterpene biosynthesis in plants. Trends Plant Sci 2002;7:366–73. in Google Scholar

21. Dudareva, N, Andersson, S, Orlova, I, Gatto, N, Reichelt, M, Rhodes, D, et al.. The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers. PNAS 2005;102:933–8. in Google Scholar

22. Banerjee, A, Sharkey, DT. Methylerythritol 4-phosphate (MEP) pathway metabolic regulation. Nat Prod Rep 2014;31:1043–55. in Google Scholar

23. Frank, A, Groll, M. The methylerythritol phosphate pathway to isoprenoids. Chem Rev 2017;117:5675–703. in Google Scholar

24. Gupta, KA, Ganjewala, D. A study on biosynthesis of citral in lemongrass (C. flexuosus) cv. Suvarna. Acta Physiol Plant 2015;37:1–8. in Google Scholar

25. Kleinig, H. The role of plastids in isoprenoid biosynthesis. Annu Rev Plant Physiol Plant Mol Biol 1989;40:39–59. in Google Scholar

26. Schwender, J, Zeidler, J, Groner, R, Muller, C, Focke, M, Braun, S, et al.. Incorporation of 1-deoxy-d-xylulose into isoprene and phytol by higher plants and algae. FEBS Lett 1997;414:129–34. in Google Scholar

27. Altincicek, B, Hintz, M, Sanderbrand, S, Wiesner, J, Beck, E, Jomaa, H. Tools for discovery of inhibitors of the 1-deoxy-d-xylulose 5-phosphate (DXP) synthase and DXP reductoisomerase: an approach with enzymes from the pathogenic bacterium Pseudomonas aeruginosa. FEMS Microbiol Lett 2000;190:329–33. in Google Scholar

28. Kollas, KA, Duin, CE, Eberl, M, Altincicek, B, Hintz, M, Reichenberg, A, et al.. Functional characterization of GcpE, an essential enzyme of the non-mevalonate pathway of isoprenoid biosynthesis. FEBS Lett 2002;532:432–6. in Google Scholar

29. Eisenreich, W, Bacher, A, Arigoni, D, Rohdich, F. Biosynthesis of isoprenoids via the non-mevalonate pathway. CMLS 2004;61:1401–26. in Google Scholar

30. Hsieh, HM, Goodman, MH. Functional evidence for the involvement of Arabidopsis IspF homolog in the non-mevalonate pathway of plastid isoprenoid biosynthesis. Planta 2006;223:779–84. in Google Scholar

31. Sauret-Gueto, S, Botella-Pavia, P, Flores-Perez, U, Martinez-Garcia, FJ, Roman San, C, Leon, P, et al.. Plastid cues post transcriptionally regulate the accumulation of key enzymes of the methylerythritol phosphate pathway in Arabidopsis. Plant Physiol 2006;141:75–84. in Google Scholar

32. Dong, L, Miettinen, K, Goedbloed, M, Verstappen, AWF, Voster, A, Jongsma, AM, et al.. Characterization of two geraniol synthases from Valeriana officinalis and Lippia dulcis: similar activity but difference in subcellular localization. Metab Eng 2013;20:198–211. in Google Scholar

33. Davis, ME, Croteau, R. Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes and diterpenes. Berlin, Heidelberg: Springer; 2000:53–95 pp.10.1007/3-540-48146-X_2Search in Google Scholar

34. Degenhardt, J, Kollner, GT, Gershenzon, J. Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants. Phytochemistry 2009;70:1621–37. in Google Scholar

35. Iijima, Y, Davidovich-Rikanati, R, Fridman, E, Gang, RD, Bar, E, Lewinsohn, E, et al.. The biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of basil. Plant Physiol 2004;136:3724–36. in Google Scholar

36. Yang, T, Li, J, Wang, XH, Zeng, Y. A geraniol-synthase gene from Cinnamomum tenuipilum. Phytochemistry 2005;66:285–93. in Google Scholar

37. Ito, M, Honda, G. Geraniol synthases from perilla and their taxonomical significance. Phytochemistry 2007;68:446–53. in Google Scholar

38. Magnard, LJ, Roccia, A, Caissard, CJ, Vergne, P, Sun, P, Hecquet, R, et al.. Plant volatiles biosynthesis of monoterpene scent compounds in roses. Science 2015;349:81–3. in Google Scholar

39. Li, X, Xu, Y, Shen, S, Yin, X, Klee, H, Zhang, B, et al.. Transcription factor CitERF71 activates the terpene synthase gene CitTPS16 involved in the synthesis of e-geraniol in sweet orange fruit. J Exp Bot 2017;68:4929–38. in Google Scholar

40. Sangwan Singh, R, Sangwan Singh, N, Luthra, R. Metabolism of acyclic monoterpenes: partial purification and properties of geraniol dehydrogenase from lemongrass (Cymbopogon flexuosus Stapf.) leaves. J Plant Physiol 1993;142:129–34.10.1016/S0176-1617(11)80952-1Search in Google Scholar

41. Roberts, CS. Production and engineering of terpenoids in plant cell culture. Nat Chem Biol 2007;3:387–95. in Google Scholar

42. Longo, AM, Sanroman, AM. Production of food aroma compounds: microbial and enzymatic methodologies. Food Technol Biotechnol 2006;44:335–53.Search in Google Scholar

43. Ishihara, K, Hamada, H, Hirata, T, Nakajima, N. Biotransformation using plant cultured cells. J Mol Catal B Enzym 2003;23:145–70. in Google Scholar

44. Shimoda, K, Kondo, Y, Nishida, T, Hamada, H, Nakajima, N, Hamada, H. Biotransformation of thymol, carvacrol, and eugenol by cultured cells of Eucalyptus perriniana. Phytochemistry 2006;67:2256–61. in Google Scholar

45. Adrekani, SRM, Linley, AP, Harkissb, JK, Mohagheghzadeh, A, Gholami, A, Mosaddegh, M. Biotransformation of monoterpenoids by suspension cultures of Lavandula angustifolia. Iran J Pharm Sci 2007;3:93–100.Search in Google Scholar

46. Lindmark-Henriksson, M, Isaksson, D, Vanek, T, Valterova, I, Hogberg, EH, Sjodin, K. Transformation of terpenes using a Picea abies suspension culture. J Biotechnol 2004;107:173–84. in Google Scholar

47. Dvorakova, M, Valterova, I, Vanek, T. Biotransformation of a monoterpene mixture by in vitro cultures of selected Conifer species. Nat Prod Commun 2007;2:233–8.Search in Google Scholar

48. Limberger, RP, Aleixo, AM, Fett-Neto, AG, Henriques, AT. Bioconversion of (+)- and (−)-alpha-pinene to (+)- and (−)-verbenone by plant cell cultures of Psychotria brachyceras and Rauvolfia sellowii. Electron J Biotechnol 2007;10:500–7. in Google Scholar

49. Bicas, LJ, Fontanille, P, Pastore, MG, Larroche, C. A bioprocess for the production of high concentrations of R-(+)-α-terpineol from R-(+)-limonene. Process Biochem 2010;45:481–6. in Google Scholar

50. Bicas, LJ, Silva, CJ, Dionisio, PA, Pastore, MG. Biotechnological production of bioflavours and functional sugars. Food Sci Techol 2010;30:7–18. in Google Scholar

51. Farooq, A, Choudhary, IM, Tahara, S, Atta-ur-Rahman, Baserc Can, HK, Demirci, F. The microbial oxidation of (–)-β-pinene by Botrytis cinerea. Z Nat C 2002;57:686–90. in Google Scholar

52. Krings, U, Hardebusch, B, Albert, D, Berger, GR, Marostica, M, Pastore, MG. Odor-active alcohols from the fungal transformation of α-farnesene. J Agric Food Chem 2006;54:9079–84. in Google Scholar

53. Marostica, RM, Pastore, MG. Production of R-(+)-α-terpineol by the biotransformation of limonene from orange essential oil using cassava waste water as medium. Food Chem 2007;101:345–50. in Google Scholar

54. Parra, A, Rivas, F, Garcia-Granados, A, Martinez, A. Microbial transformation of triterpenoids. Mini Rev Org Chem 2009;6:307–20. in Google Scholar

55. Borges, BK, Borges, SDW, Pupo, TM, Bonato, SP. Endophytic fungi as models for the stereoselective biotransformation of thioridazine. Appl Microbiol Biotechnol 2007;77:669–74. in Google Scholar

56. Borges, DW, Borges, K, Bonato, P, Said, S, Pupo, M. Endophytic fungi: natural products, enzymes and biotransformation reactions. Curr Org Chem 2009;13:1137–63. in Google Scholar

57. Soares-Castro, P, Soares, F, Santos, PM. Current advances in the bacterial toolbox for the biotechnological production of monoterpene based aroma compounds. Molecules 2021;26:91. in Google Scholar

58. Zikmundova, M, Drandarov, K, Bigler, L, Hesse, M, Werner, S. Biotransformation of 2-benzoxazolinone and 2-hydroxy-1,4-benzoxazin-3-one by endophytic fungi isolated from Aphelandra tetragona. Appl Environ Microbiol 2002;68:4863–70. in Google Scholar

59. Pimentel, M, Molina, G, Dionisio, PA, Junior Marostica, RM, Pastore, MG. The use of endophytes to obtain bioactive compounds and their application in biotransformation process. Biotechnol Res Int 2011;2011:1–11. in Google Scholar

60. Singh, A, Singh, DK, Kharwar, RN, White, JF, Gond, SK. Fungal endophytes as efficient sources of plant-derived bioactive compounds and their prospective applications in natural product drug discovery: insights, avenues, and challenges. Microorganisms 2021;9:197. in Google Scholar

61. Chen, L, Pang, Y, Luo, Y, Cheng, X, Lv, B, Li, C. Separation and purification of plant terpenoids from biotransformation. Eng Life Sci 2021. in Google Scholar

62. Yang, D, Wang, Q. Biotransformation of monoterpenes by whole cells of eleven Praxelis clematidea-derived endophytic fungi. Int J Nutr Food Eng 2021;15:32–7.Search in Google Scholar

63. Nielsen, J, Keasling, DJ. Engineering cellular metabolism. Cell 2016;164:1185–97. in Google Scholar

64. Mora-Pale, M, Sanchez-Rodriguez, PS, Linhatrdt, JR, Dordick, SJ, Koffas, GAM. Metabolic engineering and in vitro biosynthesis of phytochemicals and non-natural analogues. Plant Sci 2013;210:10–24. in Google Scholar

65. Vickers, EC, Bongers, M, Liu, Q, Delatte, T, Bouwmeester, H. Metabolic engineering of volatile isoprenoids in plants and microbes. Plant Cell Environ 2014;37:1753–75. in Google Scholar

66. Curran, KA, Alper, SH. Expanding the chemical palate of cells by combining systems biology and metabolic engineering. Metab Eng 2012;14:289–97. in Google Scholar

67. Hong, KK, Nielsen, J. Metabolic engineering of Saccharomyces cerevisiae: a key cell factory platform for future biorefineries. CMLS 2012;69:2671–90. in Google Scholar

68. Lee, WJ, Na, D, Park, MJ, Lee, J, Choi, S, Lee, YS. Systems metabolic engineering of microorganisms for natural and non-natural chemicals. Nat Chem Biol 2012;8:536–46. in Google Scholar

69. Dudley, MQ, Karim, SA, Jewett, CM. Cell-free metabolic engineering: biomanufacturing beyond the cell. Biotechnol J 2015;10:69–82. in Google Scholar

70. Pickens, BL, Tang, Y, Chooi, HY. Metabolic engineering for the production of natural products. Ann Rev Chem Biomol Eng 2011;2:211–36. in Google Scholar

71. Immethun, MC, Hoynes-O’Connor, GA, Balassy, A, Moon, ST. Microbial production of isoprenoids enabled by synthetic biology. Front Microbiol 2013;4:1–8. in Google Scholar

72. Bution, LM, Molina, G, Abrahao, RM, Pastore, MG. Genetic and metabolic engineering of microorganisms for the development of new flavor compounds from terpenic substrates. Crit Rev Biotechnol 2015;35:313–25. in Google Scholar

73. Ajikumar, KP, Tyo, K, Carlsen, S, Mucha, O, Phon, HT, Stephanopoulos, G. Terpenoids: opportunities for biosynthesis of natural product drugs using engineered microorganisms. Mol Pharm 2008;5:167–90. in Google Scholar

74. Noma, Y, Asakawa, Y. 14 Biotransformation of monoterpenoids by microorganisms, insects, and mammals. Essential 2020;585:613–767. in Google Scholar

75. Santos, SA, Pereira, N, Silva Da, MI, Sarquis, MIM, Antunes, CAO. Peroxidase catalyzed microbiological oxidation of isosafrol into piperonal. Process Biochem 2004;39:2269–75. in Google Scholar

76. Toniazzo, G, Oliveira, DD, Dariva, C, Oestreicher, GE, Antunes, CAO. Biotransformation of (−)β-pinene by Aspergillus niger ATCC 9642. Appl Biochem Biotechnol 2005;3:837–44. in Google Scholar

77. Javidnia, K, Aram, F, Solouki, M, Mehdiopour, AR, Gholami, M, Miri, R. Microbial biotransformation of some monoterpene hydrocarbons. Ann Microbiol 2009;59:349–51. in Google Scholar

78. Schewe, H, Mirata, AM, Holtmann, D, Schrader, J. Biooxidation of monoterpenes with bacterial monooxygenases. Process Biochem 2011;46:1885–99. in Google Scholar

79. Wu, T, Li, S, Zhang, B, Bi, C, Zhang, X. Engineering Saccharomyces cerevisiae for the production of the valuable monoterpene ester geranyl acetate. Microb Cell Factories 2018;17:1–0. in Google Scholar

80. Hook, LI, Ryan, S, Sheridan, H. Biotransformation of aliphatic and aromatic ketones, including several monoterpenoid ketones and their derivatives by five species of marine microalgae. Phytochemistry 2003;63:31–6. in Google Scholar

81. Li, H, Lan, W, Cai, C, Zhou, Y, Lin, Y. Biotransformation of limonene by marine bacteria. Chin J Anal Chem 2006;34:946–50. in Google Scholar

82. Carvalho De, RCCC, Fonseca Da, RMM. Biotransformation of terpenes. Biotechnol Adv 2006;24:134–42.10.1016/j.biotechadv.2005.08.004Search in Google Scholar

83. Chatterjee, T. Biotransformation of geraniol by Rhodococcus sp. strain GR3. Biotechnol Appl Biochem 2004;39:303–6. in Google Scholar

84. Wolken, W, Van Der Werf, M. Geraniol biotransformation-pathway in spores of Penicillium digitatum. Appl Microbiol Biotechnol 2001;57:731–7. in Google Scholar

85. Demyttenaere, RCJ, Herrera, CDM, Kimpe, DN. Biotransformation of geraniol, nerol and citral by sporulated surface cultures of Aspergillus niger and Penicillium sp. Phytochemistry 2000;55:363–73. in Google Scholar

86. Ponzoni, C, Gasparetti, C, Goretti, M. Biotransformation of acyclic monoterpenoids by Debaryomyces sp., Kluyveromyces sp. and Pichia sp. strains of environmental origin. Chem Biodivers 2008;5:471–83. in Google Scholar

87. Leutou, SA, Yang, G, Nenkep, NV. Microbial transformation of a monoterpene, geraniol, by the marine-derived fungus Hypocrea sp. J Microbiol Biotechnol 2009;19:1150–2.Search in Google Scholar

88. Schrader, J, Berger, GR. Biotechnological production of terpenoid flavor and fragrance compounds. Biotechnol 2008;10:373–422. in Google Scholar

89. Esmaeili, A, Tavassoli, A. Microbial transformation of citral by Penicillium sp. Acta Biochim Pol 2010;57:265–8.10.18388/abp.2010_2404Search in Google Scholar

90. Esmaeili, A, Rohany, S, Safaiyan, S. Biotransformation of citral by free and immobilized Saccharomyces cerevisiae. Chem Nat Compd 2012a;48:322–4. in Google Scholar

91. Esmaeili, A, Rohany, S, Safaiyan, S, Amir, ZS. Microbial transformation of citral by Aspergillus niger-PTCC 5011 and study of the pathways involved. Czech J Food Sci 2011;29:610–5. in Google Scholar

92. Sousa, DPD, Goncalves, RCJ, Quintans-Junior, L, Cruz, SJ, Araujo, MAD, Almeida, DNR. Study of anticonvulsant effect of citronellol a monoterpene alcohol in rodents. Neurosci Lett 2006;401:231–5. in Google Scholar

93. Pimentel, M, Molina, G, Bertucci, T, Pastore, G. Biotransformation of citronellol in rose oxide by Pseudomonas sp. Chem Eng Trans 2012;27:295–300.Search in Google Scholar

94. Demyttenaere, RCJ, Vanoverschelde, J, Kimpe, DN. Biotransformation of (R)-(+)- and (S)-(−)-citronellol by Aspergillus sp. and Penicillium sp. and the use of solid-phase microextraction for screening. J Chromatogr A 2004;1027:137–46. in Google Scholar

95. Tozoni, D, Zacaria, J, Vanderlinde, R, Delamare, LPA, Echeverrigaray, S. Degradation of citronellol, citronellal and citronellyl acetate by Pseudomonas mendocina IBPse 105. Electron J Biotechnol 2010;13:1–7. in Google Scholar

96. Velankar, RH, Heble, RM. Biotransformation of (l)-citronellal to (l)-citronellol by free and immobilized Rhodotorula minuta. Electron J Biotechnol 2003;6:90–103. in Google Scholar

97. Yu, W, Liu, H, Liu, M, Liu, Z. Selective hydrogenation of citronellal to citronellol over polymer-stabilized noble metal colloids. React Funct Polym 2000;44:21–9. in Google Scholar

98. Duetz, AW, Bouwmeester, H, Beilen Van, BJ, Witholt, B. Biotransformation of limonene by bacteria, fungi, yeasts, and plants. Appl Microbiol Biotechnol 2003;61:269–77. in Google Scholar

99. Panakkal, EJ, Kitiborwornkul, N, Sriariyanun, M, Ratanapoompinyo, J, Yasurin, P, Asavasanti, S, et al.. Production of food flavouring agents by enzymatic reaction and microbial fermentation. Appl Sci Eng Prog 2021;14:297–312. in Google Scholar

100. de Souza Sevalho, E, Paulino, BN, de Souza, AQL, de Souza, ADL. Fungal biotransformation of limonene and pinene as a biotechnological approach for production of aroma compounds 2021;1–17. in Google Scholar

101. Molina, G, Bution, LM, Bicas, LJ, Dolder, HAM, Pastore, MG. Comparative study of the bioconversion process using R-(+)- and S-(−)-limonene as substrates for Fusarium oxysporum 152B. Food Chem 2015;174:606–13. in Google Scholar

102. Bicas, JL, Fontanille, P, Pastore, GM, Larroche, C. Characterization of monoterpene biotransformation in two Pseudomonads. J Appl Microbiol 2008;105:1991–2001. in Google Scholar

103. Chatterjee, T, Bhattacharyya, D. Biotransformation of limonene by Pseudomonas putida. Appl Microbiol Biotechnol 2001;55:541–6. in Google Scholar

104. Sales, A, Afonso, LF, Americo, JA, de Freitas Rebelo, M, Pastore, GM, Bicas, JL. Monoterpene biotransformation by Colletotrichum species. Biotechnol Lett 2018;40:561–7. in Google Scholar

105. Sales, A, Pastore, GM, Bicas, JL. Optimization of limonene biotransformation to limonene-1,2-diol by Colletotrichum nymphaeae CBMAI 0864. Process Biochem 2019;1:25–31. in Google Scholar

106. Rottava, I, Cortina, FP, Grando, EC, Colla, SRA, Martello, E, Cansian, LR, et al.. Isolation and screening of microorganisms for R-(+)-limonene and (−)-β-pinene biotransformation. Appl Biochem Biotechnol 2010;162:719–32. in Google Scholar

107. Rottava, I, Cortina, FP, Martello, E, Cansian, LR, Toniazzo, G, Antunes, CAO, et al.. Optimization of α-terpineol production by the biotransformation of R-(+)-limonene and (−)-β-pinene. Appl Biochem Biotechnol 2011;164:514–23. in Google Scholar

108. de Medeiros, TDM, Alexandrino, TD, Pastore, GM, Bicas, JL. Extraction and purification of limonene-1,2-diol obtained from the fungal biotransformation of limonene. Separ Purif Technol 2021;254:117683. in Google Scholar

109. Rozenbaum, FH, Patitucci, LM, Antunes, CAO, Pereira, N. Production of aromas and fragrances through microbial oxidation of monoterpenes. Braz J Chem Eng 2006;23:273–9. in Google Scholar

110. Bnina, EB, Daami-Remadi, M, Jannet, HB. Access to oxygenated monoterpenes via the biotransformation of (R)-Limonene by Trichoderma harzianum and Saccharamyces cerevisiae. Chem Afric 2020;3:647–56. in Google Scholar

111. Sales, A, Felipe, LDO, Bicas, JL. Production, properties, and applications of α-terpineol. Food Bioprocess Technol 2020;13:1261–79. in Google Scholar

112. Bhatia, PS, Letizia, SC, Api, MA. Fragrance material review on alpha-terpineol. Food Chem Toxicol 2008;46:280–5. in Google Scholar

113. Jun, M, Jeong, W, Ho, C. Health promoting properties of natural flavor substances. Food Sci Biotechnol 2006;15:329.Search in Google Scholar

114. Schelz, Z, Molnar, J, Hohmann, J. Antimicrobial and antiplasmid activities of essential oils. Fitoterapia 2006;77:279–85. in Google Scholar

115. Adams, A, Demyttenaere, RCJ, Kimpe, DN. Biotransformation of (R)-(+)- and (S)-(−)-limonene to α-terpineol by Penicillium digitatum – investigation of the culture conditions. Food Chem 2003;80:525–34. in Google Scholar

116. Demyttenaere, JC, Van Belleghem, K, De Kimpe, N. Biotransformation of (R)-(+)-and (S)-(−)-limonene by fungi and the use of solid phase microextraction for screening. Phytochemistry 2001;57:199–208. in Google Scholar

117. Tai, NY, Xu, M, Ren, NJ, Dong, M, Yang, YZ, Pan, S, et al.. Optimisation of α-terpineol production by limonene biotransformation using Penicillium digitatum DSM 62840. J Sci Food Agric 2016;96:954–61. in Google Scholar

118. Prieto, AGS, Perea, AJV, Ortiz, CCL. Microbial biotransformation of (R)-(+)-limonene by Penicillium digitatum DSM 62840 for producing (R)-(+)-terpineol. Vitae 2011;18:136–72.10.17533/udea.vitae.10068Search in Google Scholar

119. Molina, G, Pessôa, MG, Bicas, JL, Fontanille, P, Larroche, C, Pastore, GM. Optimization of limonene biotransformation for the production of bulk amounts of α-terpineol. Bioresour Technol 2019;1:122–80. in Google Scholar

120. Pescheck, M, Mirata, AM, Brauer, B, Krings, U, Berger, GR, Schrader, J. Improved monoterpene biotransformation with Penicillium sp. by use of a closed gas loop bioreactor. J Ind Microbiol Biotechnol 2009;36:827–36. in Google Scholar

121. Betts, JT. Solid phase microextraction of volatile constituents from individual fresh eucalyptus leaves of three species. Planta Med 2000;66:193–5. in Google Scholar

122. Vespermann, AK, Paulino, NB, Barcelos, CM. Biotransformation of α- and β-pinene into flavor compounds. Appl Microbiol Biotechnol 2017;101:1805–17. in Google Scholar

123. Joshi, AR, Sharma, UR, Samani, K, Surendra, V, Swamy, G, Manjunath, PM. Review on therapeutic activity of pinene (C10H16): an essential oil. Int J Adv Res Pharm Educ 2020;2:28–33.Search in Google Scholar

124. Çorbac, C. Biotransformation of terpene and terpenoid derivatives by Aspergillus niger NRRL 326. Biologia 2020;75:1473–81.10.2478/s11756-020-00459-1Search in Google Scholar

125. Parshikov, IA, Sutherland, JB. The use of Aspergillus niger cultures for biotransformation of terpenoids. Process Biochem 2014;49:2086–3000. in Google Scholar

126. Lee, YS, Kim, HS, Hong, YC. Biotransformation of (−)-α-pinene and geraniol to α-terpineol and p-menthane-3,8-diol by the white rot fungus. Polyporusbrumalis J Microbiol 2015;53:462–7. in Google Scholar

127. Esmaeili, A, Hashemi, E, Safaiyan, S, Rustaiyan, A. Biotransformation of myrcene by Pseudomonas putida PTCC 1694. Herba Pol 2011;57:51–8.Search in Google Scholar

128. Esmaeili, A, Hashemi, E. Biotransformation of myrcene by Pseudomonas aeruginosa. Chem Cent J 2011;5:1–7. in Google Scholar

129. Thompson, ML, Marriott, R, Dowle, A, Grogan, G. Biotransformation of β-myrcene to geraniol by a strain of Rhodococcus erythropolis isolated by selective enrichment from hop plants. Appl Microbiol Biotechnol 2010;85:721–30. in Google Scholar

130. Krugener, S, Krings, U, Rinne, S, Berger, GR. Bioconversion of β-myrcene to perillene-metabolites, pathways, and enzymes. In: Proc Weurman Symposium; 2008.Search in Google Scholar

131. Esmaeili, A, Khodadadi, A, Safaiyan, S. Biotransformation of thymol by Aspergillus niger. Chem Nat Compd 2012;47:966–8. in Google Scholar

132. Pereira, I, Severino, P, Santos, AC, Silva, AM, Souto, EB. Linalool bioactive properties and potential applicability in drug delivery systems. Colloids Surf B Biointerfaces 2018;1:566–78. in Google Scholar

133. Bormann, S, Etschmann, WMM, Mirata, AM, Schrader, J. Integrated bioprocess for the stereospecific production of linalool oxides from linalool with Corynespora cassiicola DSM 62475. J Ind Microbiol Biotechnol 2012;39:1761–9. in Google Scholar

134. Etschmann, WMM, Bormann, S, Schrader, J. Microbial conversion of (±) linalool to linalool oxides by Corynespora cassiicola. Fla Sci 2014:201–4. in Google Scholar

135. Mirata, MA, Wüst, M, Mosandl, A, Schrader, J. Fungal biotransformation of (±)-linalool. J Agric Food Chem 2008;56:3287–96. in Google Scholar

136. King, A, Richard Dickinson, J. Biotransformation of monoterpene alcohols by Saccharomyces cerevisiae, Torulaspora delbrueckii and Kluyveromyces lactis. Yeast 2000;16:499–506.<499::aid-yea548>;2-e.10.1002/(SICI)1097-0061(200004)16:6<499::AID-YEA548>3.0.CO;2-ESearch in Google Scholar

Received: 2021-07-04
Accepted: 2021-11-14
Published Online: 2021-12-07
Published in Print: 2022-05-25

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 5.10.2023 from
Scroll to top button