Current Science

Open Access Open Access  Restricted Access Subscription Access

Methoxybenzaldehydes in Plants:Insight to the Natural Resources, Isolation, Application and Biosynthesis


Affiliations
1 Natural Product Biotechnology Group, Agricultural and Food Engineering Department, Indian Institute of Technology Kharagpur, Kharagpur 721 302, India
 

Methoxybenzaldehydes in plants are one of the important groups of benzoate derivatives. Some of them, exhibiting refreshing fragrance can be used as flavouring ingredients in food and cosmetics. Therefore, they have important roles in food and cosmetic industries. Methoxybenzaldehydes also exhibit significant medicinal properties and thus have certain prospects in pharmaceutical industry. Biosynthesis of benzoic acid in plants has been explored in the last decade. There has been focus on benzaldehyde and methoxybenzaldehyde biosynthesis as well. There have been several studies regarding the biosynthetic route and mechanism of formation of benzaldehyde via benzoic acid from cinnamate and further addition of 'methoxy' group to it in the last few years. Still there are many ambiguities regarding the medicinal properties and biosynthesis of methoxybenzaldehydes. This review highlights the latest advances in fragrant methoxybenzaldehyde research and the knowledge gaps till date. The review also discusses the occurrence of methoxybenzaldehydes in plants, their separation methods, medicinal properties and biosynthesis.

Keywords

Biosynthesis, Plants, Medicinal Properties, Methoxybenzaldehyde, Vanillin.
User
Notifications
Font Size

  • Chakraborty, D., Sircar, D. and Mitra, A., Phenylalanine ammonialyase-mediated biosynthesis of 2-hydroxy-4-methoxybenzaldehyde in ischolar_mains of Hemidesmus indicus. J. Plant Physiol., 2008, 165, 1033–1040.

  • Kundu, A. and Mitra, A., Flavouring extracts of Hemidesmus indicus ischolar_mains and Vanilla planifolia pods exhibit in vitro acetylcholinesterase inhibitory activities. Plant Foods Hum. Nutr., 2013, 68, 247–253.

  • Kundu, A. and Mitra, A., Evaluating tyrosinase (monophenolase) inhibitory activity from fragrant ischolar_mains of Hemidesmus indicus for potent use in herbal products. Ind. Crops Prod., 2014, 52, 394–399.

  • Zamzuri, N. A. and Abd-Aziz, S., Biovanillin from agro wastes as an alternative food flavour. J. Sci. Food Agric., 2012, 93, 429–438.

  • Chopra, R. N., Nayar, S. R. and Chopra, I. C., In Glossary of Indian Medicinal Plants, CSIR Publication, New Delhi, 1980, p. 132.

  • Sircar, D., Dey, G. and Mitra, A., A validated HPLC method for simultaneous determination of 2-hydroxy-4-methoxybenzaldehyde and 2-hydroxy-4-methoxybenzoic acid in ischolar_main organs of Hemidesmus indicus. Chromatographia, 2007, 65, 349–353.

  • Kubo, I. and Kinst-Hori, I., 2-Hydroxy-4-methoxybenzaldehyde a potent tyrosinase inhibitor from African medicinal plants. Planta Med., 1999, 65, 19–22.

  • Fimognari, C. et al., Mitochondrial pathway mediates the antileukemic effects of Hemidesmus indicus, a promising botanical drug. PLOS ONE, 2011, 6, e21544.

  • Nagarajan, S., Jagan Mohan Rao, L. and Gurudutt, K. N., Chemical composition of the volatiles of Hemidesmus indicus R. Br. Flavour Frag. J., 2001, 16, 212–214.

  • Girdhar, P., Rajasekaran, T. and Ravishankar, G. A., Improvement of growth and ischolar_main specific flavour compound 2-hydroxy-4methoxybenzaldehyde of micropropagated plants of Decalepis hamiltonii Wight & Arn., under triacontanol treatment. Sci. Hortic., 2005, 106(2), 228–236.

  • Kundu, A., Jawali, N. and Mitra, A., Shikimate pathway modulates the elicitor-stimulated accumulation of fragrant 2-hydroxy-4methoxybenzaldehyde in Hemidesmus indicus ischolar_mains. Plant Physiol. Biochem., 2012, 56, 104–108.

  • Mukonyi, K. W. and Ndiege, I. O., 2-Hydroxy-4-methoxybenzaldehyde: aromatic taste modifying compound from Mondia whytei. Bull Chem. Soc. Ethiop., 2001, 15(2), 137–141.

  • Jeong, E. Y., Cho, K. S. and Lee, H. S., Food protective effects of Periploca sepium oil and its active component against stored food mites. J. Food Prot., 2012, 75(1), 118–122.

  • Shreaz, S., Bhatia, R., Khan, N., Muralidhar, S., Basir, S. F., Manzoor, N. and Khal, L. A., Exposure of Candida to p-anisaldehyde inhibits its growth and ergosterol biosynthesis. J. Gen. Appl. Microbiol., 2011, 57(3), 129–136.

  • Grey, R. and Bonner, J., Structure determination and synthesis of a plant growth inhibitor, 3-acetyl-6-methoxybenzaldehyde, found in the leaves of Encclia furinosa. J. Am. Chem. Soc., 1948, 70(3), 1249–1253.

  • Podstolski, A., Havin-Frenkel, D., Malinowski, J., Blount, J. W., Kourteva, G. and Dixon, R. A., Unusual 4-hydroxybenzaldehyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifolia. Phytochemistry, 2002, 61, 611–620.

  • Dignum, M. J. W., Kerler, J. and Verpoorte, R., Vanilla production: technological, chemical, and biosynthetic aspects. Food Rev. Int., 2001, 17, 199–219.

  • Paramita, V. and Yulianto, M. E., Effect of β-glucosidase activity on the vanillin enzymatic formation by using rumen liquid for cell walls degradation. J. Food Res., 2013, 2, 65–69.

  • Makkar, H. P. S. and Beeker, K., Isolation of tannins from leaves of some trees and shrubs and their properties. J. Agric. Food Chem., 1994, 42, 731–734.

  • Sreekumar, S., Seeni, S. and Puspagandhan, P., Production of 2hydroxy 4-methoxy benzaldehyde using ischolar_main cultures of Hemidesmus indicus. Biotech. Lett., 1998, 20, 631–635.

  • Sreekumar, S., Seeni, S., and Pushpagandhan, P., Micropropagation of Hemidesmus indicus for cultivation and production of 2hydroxy 4-methoxy benzaldehyde. Plant Cell Tissue Organ Cult., 2000, 62, 211–218.

  • Wang, J. et al., Antimicrobial and antioxidant activities of the ischolar_main bark essential oil of Periploca sepium and its main component 2hydroxy-4-methoxybenzaldehyde. Molecules, 2010, 15, 5807–5817.

  • Rey, S., Carbonel, F., Dupont, A. and Vandoorn, M., LaboPharma-Probl. Tech., 1980, 28, 493–496.

  • Belay, M. T. and Poole, C. F., Determination of vanillin and related flavor compounds in natural vanilla extracts and vanilla flavored foods by thin layer chromatography and automated multiple development. Chromatographia, 1993, 37, 365–373.

  • Butehorn, U. and Pyell, U., Micellar electrokinetic chromatography as a screening method for the analysis of vanilla flavourings and vanilla extracts. J. Chromatogr. A, 1996, 736, 321–332.

  • Ranadive, A. S., Vanillin and related flavor compounds in vanilla extracts made from beans of various global origins. J. Agric. Food Chem., 1992, 40, 1922–1924.

  • Rao, S. R. and Ravisankar, G. A., Biotransformation of isoeugenol to vanilla flavour metabolites and capsaicin in suspended and immobilized cell cultures of Capsicum frutescens: study of the influence of b-cyclodextrin and fungal elicitor. Process Biochem., 1999, 35, 341–348.

  • Waliszewski, K. N., Pardio, V. T. and Ovando, S. L., A simple and rapid HPLC technique for vanillin determination in alcohol extract. Food Chem., 2007, 101, 1059–1062.

  • Sinha, A. K., Verma, S. C. and Sharma, U. K., Development and validation of an RP-HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia. J. Sep. Sci., 2007, 30, 15–20.

  • Cicchetti, E. and Chaintreau, A., Quantitation of the main constituents of vanilla by reverse phase HPLC and ultra-high-pressureliquidchromatography with UV detection: method validation and performance comparison. J. Sep. Sci., 2009, 32, 1957–1964.

  • López-Malo, A., Alzamora, S. M. and Argaiz, A., Effect of natural vanillin on germination time and radial growth of moulds in fruit based agar systems. Food Microbiol., 1995, 12, 213–219.

  • Cerrutti, P. and Alzamora, S. M., Inhibitory effects of vanillin on some food spoilage yeasts in laboratory media and fruit purees. Int. J. Food Microbiol., 1996, 29, 379–386.

  • Fitzgerald, D. J., Stratford, M., Gasson, M. J. and Narbad, A., The potential application of vanillin in preventing yeast spoilage of ready-to-drink beverages. J. Food Prot., 2004, 67, 391–395.

  • Fitzgerald, D. J., Stratford, M., Gasson, M. J., Ueckert, J., Bos, A. and Narbad, A., Mode of antimicrobial action of vanillin against Escherichia coli, Lactobacillus plantarumand Listeria innocua. J. Appl. Microbiol., 2004, 97, 104–113.

  • Arulvasu, C., Shivaranjani, S., Revati, M. and Hemavati, M., Free radical scavenging activity and cytotoxic effect of anisaldehyde on human cancer cell line. In Paper presented at the International Conference on Advance in New Materials. Department of Inorganic Chemistry, University of Madras, Chennai, 20 and 21 June 2014.

  • Lin, C., Yang, J., Chang, C., Kuo, S., Lee, M. and Huang, L., Synthesis and anticancer activity of benzyloxybenzaldehyde derivatives against HL-60 cells. Bioorg. Med. Chem., 2005, 13, 1537–1544.

  • Kubo, I. and Kinst-Hori, I., Tyrosinase inhibitors from anise oil. J. Agric. Food Chem., 1998, 46, 1268–1271.

  • Mahanga, G. M., Akenga, T. O., Lwande, W. and Ndiege, I. O., 2Hydroxy-4-methoxybenzaldehyde: larvicidal structure activity studies. Bull. Chem. Soc. Ethiop., 2005, 19(1), 61–68.

  • Beuerle, T. and Pichersky, E., Purification and characterization of benzoate: coenzyme A ligase from Clarkia breweri. Arch. Biochem. Biophys., 2002, 400, 258–264.

  • Walton, N. J., Mayer, M. J. and Narbad, A., Vanillin. Phytochemistry, 2003, 63, 505–515.

  • Boatright, J. et al., Understanding in vivo benzenoid meta bolism in petunia petal tissue. Plant Physiol., 2004, 135, 1993–2011.

  • Mustafa, N. R. and Verpoorte, R., Chorismate derived C6C1 compounds in plants. Planta, 2005, 222, 1–5.

  • Wildermuth, M. C., Variation on a theme: synthesis and modification of plant benzoic acids. Curr. Opin. Plant Biol., 2006, 9, 288–296.

  • Orlova, I. et al., Reduction of benzenoid synthesis in petunia flowers reveals multiple pathways to benzoic acid and enhancement in auxin transport. Plant Cell, 2006, 18, 3458–3475.

  • Qualleya, A. V., Widhalma, J. R., Funmilayo, A., Kisha, C. M. and Dudareva, N., Completion of the core β-oxidative pathway of benzoic acid biosynthesis in plants. Proc. Natl. Acad. Sci. USA, 2012, 109(40), 16383–16388.

  • Walton, N. J., Narbad, A., Faulds, C. B. and Williamson, G., Novel approaches to the biosynthesis of vanillin. Curr. Opin. Biotechnol., 2000, 11, 490–496.

  • Kanisawa, T., Tokoro, K. and Kawahara, S. In Olfaction Taste XI (Proceeding of the International Symposium) (eds Kurihara, K., Suzuki, N. and Ogawa, H.), Springer, Tokyo, 1994, p. 268.

  • Tokoro, K., Kawahara, S., Amano, A., Kanisawa, T. and Indo, M., In Flavour Science and Technology (eds Bessiere, Y. and Thomas, A. F.), John Wiley, Chichester, 1990, Vol. 73, pp. 73–76.

  • Zenk, M. H., Biosynthese von vanillin in Vanilla planifolia Andr. Z. Pflanzenphysiol., 1965, 53, 404–414.

  • El-Basyouni, S. Z., Chen, D., Ibrahim, R. K., Neish, A. C. and Towers, G. H. N., The biosynthesis of hydroxybenzoic acids in higher plants. Phytochemistry, 1964, 3, 485–492.

  • Negishi, O., Sugiura, K. and Negishi, Y., Biosynthesis of vanillin via ferulic acid in Vanilla planifolia. J. Agric. Food Chem., 2009, 11, 57(21), 9956–9961.

  • Romagnoli, L. G. and Knorr, D., Effects of ferulic acid treatment on growth and flavour development of cultured Vanilla planifola cells. Food Biotechnol., 1988, 2, 83–104.

  • Labuda, I. M., Keon, K. A. and Goers, S. K., Progress in flavour precursor studies: analysis, generation, biotechnology. In Proceedings of the International Conference (eds Schreier, P. and Winter Halter, P.), Allured Publishing Corp., IL, 1993, p. 477.

  • Funk, C. and Brodelius, P. E., Phenylpropanoid metabolism in suspension cultures of Vanilla planifolia Andr. II. Effects of precursor feeding and metabolic inhibitors. Plant Physiol., 1990, 94, 95–101.

  • Funk, C. and Brodelius, P. E., Phenylpropanoid metabolism in suspension cultures of Vanilla planifolia Andr. III. Conversion of 4-methoxycinnamic acids into 4-hydroxybenzoic acids. Plant Physiol., 1990, 94, 102–108.

  • French, C. J., Vance, C. P. and Towers, G. H. N., Conversion of p-coumaric acid to p-hydroxybenzoic acid by cell free extracts of potato tubers and Polyporu shispidus. Phytochemistry, 1976, 15, 564–566.

  • Schnitzler, J. P., Madlung, J., Rose, A. and Seitz, H. U., Biosynthesis of p-hydroxybenzoic acid in elicitor-treated carrot cell cultures. Planta, 1992, 188, 594–600.

  • Sircar, D. and Mitra, A., Evidence for p-hydroxybenzoate formation involving phenylpropanoid chain-cleavage in hairy ischolar_mains of Daucus carota. J. Plant Physiol., 2008, 165, 407–414.

  • Yazaki, K., Heide, L. and Tabata, M., Formation of phydroxybenzoic acid from p-coumaric acid by cell free extract of Lithospermum erythrorhizon cell cultures. Phytochemistry, 1991, 30, 2233–2236.

  • Gasson, M. J. et al., Metabolism of ferulic acid to vanillin: a bacterial gene of the enoyl-SCoA hydratase/isomerase superfamily encodes an enzyme for the hydration and cleavage of a hydroxycinnamic acid SCoAthioester. J. Biol. Chem., 1998, 273, 4163–4170.

  • Mitra, A. et al., 4-Hydroxycinnamoyl-CoA hydratase/lyase (HCHL) – an enzyme of phenylpropanoid chain cleavage from Pseudomonas. Arch. Biochem. Biophys., 1999, 365, 10–16.

  • Havin-Frenkel, D., Podstolski, A. and Knorr, D., Effect of light on vanillin precursors formation by in vitro cultures of Vanilla planifolia. Plant Cell Tissue Org. Cult., 1996, 45, 133–136.

  • Gallage, N. J. et al., Vanillin formation from ferulic acid in Vanilla planifolia is catalysed by a single enzyme. Nature Commun., 2014, 5, 4037; doi:10.1038/ncomms5037

  • Pak, F. E., Gropper, S., Dai, W. D., Havkin-Frenkel, D. and Belanger, F. C., Characterization of a multifunctional methyltransferases from the orchid Vanilla planifolia. Plant Cell Rep., 2004, 22, 959–966.

  • Giridhar, P., Rajasekaran, T., Nagarajan, S. and Ravishankar, G. A., Production of 2-hydroxy-4-methoxybenzaldehyde in ischolar_mains of tissue culture raised and acclimatized plants of Decalepis hamiltonii Wight & Arn., an endangered shrub endemic to southern India and evaluation of its performance vis-a-vis plants from natural habitat. Indian J. Exp. Biol., 2004, 42(1), 106–110.

  • Kneer, R., Poulev, A. A., Olesinski, A. and Raskin, I., Characterization of the elicitor-induced biosynthesis and secretion of genistein from ischolar_mains of Lupinus luteus L. J. Exp. Bot., 1999, 50, 1553-1559.


Abstract Views: 2771

PDF Views: 81




  • Methoxybenzaldehydes in Plants:Insight to the Natural Resources, Isolation, Application and Biosynthesis

Abstract Views: 2771  |  PDF Views: 81

Authors

Anish Kundu
Natural Product Biotechnology Group, Agricultural and Food Engineering Department, Indian Institute of Technology Kharagpur, Kharagpur 721 302, India
Adinpunya Mitra
Natural Product Biotechnology Group, Agricultural and Food Engineering Department, Indian Institute of Technology Kharagpur, Kharagpur 721 302, India

Abstract


Methoxybenzaldehydes in plants are one of the important groups of benzoate derivatives. Some of them, exhibiting refreshing fragrance can be used as flavouring ingredients in food and cosmetics. Therefore, they have important roles in food and cosmetic industries. Methoxybenzaldehydes also exhibit significant medicinal properties and thus have certain prospects in pharmaceutical industry. Biosynthesis of benzoic acid in plants has been explored in the last decade. There has been focus on benzaldehyde and methoxybenzaldehyde biosynthesis as well. There have been several studies regarding the biosynthetic route and mechanism of formation of benzaldehyde via benzoic acid from cinnamate and further addition of 'methoxy' group to it in the last few years. Still there are many ambiguities regarding the medicinal properties and biosynthesis of methoxybenzaldehydes. This review highlights the latest advances in fragrant methoxybenzaldehyde research and the knowledge gaps till date. The review also discusses the occurrence of methoxybenzaldehydes in plants, their separation methods, medicinal properties and biosynthesis.

Keywords


Biosynthesis, Plants, Medicinal Properties, Methoxybenzaldehyde, Vanillin.

References





DOI: https://doi.org/10.18520/cs%2Fv111%2Fi8%2F1325-1334