Abstract
Plant secondary metabolites, the so-called natural products, are used as flavors, food additives, and pharmaceuticals. Since complex natural products are not economically produced by total chemical synthesis except for some small molecules, most of the useful metabolites are still obtained from wild or cultivated plant resources. Alternatively, plant cell culture technique would be a potential method to produce these useful secondary metabolites, and commercial production of some useful secondary metabolites has been achieved (Kolewe et al. 2008; Smetanska 2008). Furthermore, biotransformation by plant cell cultures could be a useful method to convert natural products or unnatural synthetic products into chemically different products of economical importance. This chapter will focus on biosynthesis and biotransformation of useful chemical compounds using plant cell culture technology.
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References
Akiu S, Suzuki Y, Fujinuma Y, Asahara T, Fukuda M (1988) Inhibitory effect of arbutin in melanogenesis: biochemical study in cultured B16 melanoma cells and effect on the UV-induced pigmentation in human skin. Proc Jpn Soc Investig Dermatol 12:138–139
Alfermann AW, Schuller I, Reinhard E (1980) Biotransformation of cardiac glycosides by immobilized cells of digitalis lanata. Planta Med 40:218–223
Bley KR (2004) Recent developments in transient receptor potential vanilloid receptor agonist-based therapies. Expert Opin Investig Drugs 13:1445–1456
Botta B, Monache GD, Misiti D, Vitali A, Zappia G (2001) Aryltetralin ligrans: chemistry, pharmacology and biotransformations. Curr Med Chem 8:1363–1381
Eilert U, DeLuca V, Kurz WGW, Constabel F (1987) Alkaloid formation by habituated and tumorous cell suspension cultures of Catharanthus roseus. Plant Cell Rep 6:271–274
Eilert U, Kurz WGW, Constabel F (1985) Stimulation of sanguinarine accumulation in Papaver somniferum cell cultures by fungal elicitors. J Plant Physiol 119:65–76
Facchini PJ, Hagel JM, Liscombe DK, Loukania N, MacLeod BP, Samanani N, Zulak KG (2007) Opium poppy: blueprint for an alkaloid factory. Phytochem Rev 6:97–124
Facchini PJ, De Luca V (2008) Opium poppy and madagascar periwinkle: model non-model systems to investigate alkaloid biosynthesis in plants. Plant J 54:763–784
Frense D (2007) Taxanes: perspectives for biotechnological production. Appl Microbiol Biotech-nol 73:1233–1240
Fujita Y, Hara Y, Suga C, Morimoto T (1981) Production of shikonin derivatives by cell suspension cultures of Lithospermum erythrorhizon. II. A new medium for the production of shikonin derivatives. Plant Cell Rep 1:61–63
Furuya T, Kawaguchi K, Hirotani M (1988) Biotransformation of digitoxigenin by cell suspension cultures of Strophanthus gratus. Phytochemistry 27:2129–2133
Furuya T, Yoshikawa T, Orihara Y, Oda H (1983) Saponin production in cell suspension cultures of Panax ginseng. Planta Med 48:83–87
Georgiev MI, Pavlov AI, Bley T (2007) Hairy root type plant in vitro systems as sources of bioactive substances. Appl Microbiol Biotechnol 74:1175–1185
Hashimoto T, Hayashi A, Amano Y, Kohno J, Iwanari H, Usuda S, Yamada Y (1991) Hyoscya-mine 6β-hydroxylase, an enzyme involved in tropane alkaloid biosynthesis, is localized at the pericycle of the root. J Biol Chem 266:4648–4653
Hashimoto T, Yamada Y (1994) Alkaloid biogenesis: molecular aspects. Annu Rev Plant Physiol Plant Mol Biol 45:257–285
Hayashi H, Fukui H, Tabata M (1988) Examination of triterpenoids produced by callus and cell suspension cultures of Glycyrrhiza glabra. Plant Cell Rep 7:508–511
Hayashi H, Sakai T, Fukui H, Tabata M (1990) Formation of soyasaponins in licorice cell suspension cultures. Phytochemistry 29:3127–3129
Hayashi H, Fukui H, Tabata M (1993) Distribution pattern of saponins in different organs of Glycyrrhiza glabra. Planta Med 59:351–353
Hayashi H, Huang P, Inoue K (2003) Up-regulation of soyasaponin biosynthesis by methyl jasmonate in cultured cells of Glycyrrhiza glabra. Plant Cell Physiol 44:404–411
Hayashi H, Huang P, Takada S, Obinata M, Inoue K, Shibuya M, Ebizuka Y (2004) Differential expression of three oxidosqualene cyclase mRNAs in Glycyrrhiza glabra. Biol Pharm Bull 27:1086–1092
Heide L, Nishioka N, Fukui H, Tabata M (1989) Enzymatic regulation of shikonin biosynthesis in Lithospermum erythrorhizon cell cultures. Phytochemistry 28:1873–1877
Hirotani M, Furuya T (1980) Biotransformation of digitoxigenin by cell suspension cultures of Digitalis purpurea. Phytochemistry 19:531–534
Inomata S, Yokoyama M, Seto S, Yanagi M (1991) High level production of arbutin from hydroquinone in suspension cultures of Catharanthus roseus. Plant Cell Physiol 36:315–319
Jennewein S, Croteau R (2001) Taxol: biosynthesis, molecular genetics, and biotechnological applications. Appl Microbiol Biotechnol 57:13–19
Kamada H, Okamura N, Satake M, Harada H, Shimomura K (1986) Alkaloid production by hairy root cultures in Atropa belladonna. Plant Cell Rep 5:239–242
Kaminaga Y, Nagatsu A, Akiyama T, Sugimoto N, Yamazaki T, Maitani T, Mizukami H (2003) Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus. FEBS Lett 555:311–316
Kawaguchi K, Hirotani M, Furuya T (1989) Biotransformation of digitoxigenin by cell suspension cultures of Strophanthus intermedius. Phytochemistry 28:1093–1097
Kim YS, Cho JH, Ahn J, Hwang B (2006) Upregulation of isoprenoid pathway genes during enhanced saikosaponin biosynthesis in the hairy roots of Bupleurum falcatum. Mol Cell 22:269–274
Kitajima M, Fischer U, Nakamura M, Ohsawa M, Ueno M, Takayama H, Unger M, Stoeckigt J, Aimi N (1998) Anthraquinones from Ophiorrhiza pumila tissue and cell cultures. Phytochem-istry 48:107–111
Kolewe ME, Gaurav V, Roberts SC (2008) Pharmaceutically active natural product synthesis and supply via plant cell culture technology. Mol Pharm 5:243–256
Kometani T, Tanimoto H, Nishijima T, Kanabara I, Okada S (1993) Glucosylation of capsaicin by cell suspension cultures of Coffea arabica. Biosci Biotechnol Biochem 57:2192–2193
Kopec SE, Irwin RS, DeBellis RJ, Bohlke MB, Maher TJ (2008) The effects of Tween-80 on the integrity of solutions of capsaicin: useful information for performing tussigenic challenges. Cough 4:3
Kutney JP, Chen YP, Gao S, Hewitt GM, Kuri-Brena F, Milanova RK, Stoynov N (1993) Studies with plant cell cultures of Podophyllum peltatum L. II. Biotransformation of dibenzylbutano-lides to lignans. Development of a “biological factory” for lignan synthesis. Heterocycles 36:13–20
Li SM, Hennig S, Heide L (1998) Shikonin: a geranyl diphosphate-derived plant hemiterpenoid formed via the mevalonate pathway. Tetrahedron Lett 39:2721–2724
Liu C, Zhao Y, Wang Y (2006) Artemisinin: current state and perspectives for biotechnological production of an antimalarial drug. Appl Microbiol Biotechnol 72:11–20
Lorence A, Medina-Boliver F, Nessler CL (2004) Camptothecin and 10-hydroxycamptothecin from Camptotheca acuminata hairy root. Plant Cell Rep 22:437–441
Lorence A, Nessler CL (2004) Camptothecin, over four decades of surprising findings. Phyto-chemistry 65:2735–2749
Maheshwari RK, Singh AK, Gaddipati J, Srimal RC (2006) Multiple biological activities of curcumin: a short review. Life Sci 27:2081–2087
Mano Y, Nabeshima S, Matsui C, Ohkawa H (1986) Production of tropane alkaloids by hairy root cultures. Agric Biol Chem 50:2715–2722
Mano Y, Ohkawa H, Yamada Y (1989) Production of tropane alkaloids by hairy root cultures of Duboisia leichhardtii transformed by Agrobacterium rhizogenes. Plant Sci 59:191–201
Masada S, Kawase Y, Nagatoshi M, Oguchi Y, Terasaka K, Mizukami H (2007) An efficient chemoenzymatic production of small molecule glucosides with in situ UDP-glucose recycling. FEBS Lett 581:2562–2567
Matsuda J, Okabe S, Hashimoto T, Yamada Y (1991) Molecular cloning of hyoscyamine 6beta-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, from cultured roots of Hyoscyamus niger. J Biol Chem 266:9460–9464
Mihara S, Hiraoka K, Kameda W (1992) Synthesis of N-[4-(R-D-glucopyranosyloxy)-3-methox-ybenzyl] nonamide and its β-anomer. J Agric Food Chem 40:2057–2059
Mizukami H, Konoshima M, Tabata M (1978) Variation in pigment production in Lithospermum erythrorhizon callus cultures. Phytochemistry 17:95–97
Moyano E, Palazón J, Bonfill M, Osuna L, Cusinó RM, Oksman-Caldentey KM, Piñol MT (2007) Biotransformation of hyoscyamine into scopolamine in transgenic tobacco cell cultures. J Plant Physiol 164:521–524
Nakagawa K, Konagai A, Fukui H, Tabata M (1984) Release and crystallization of berber-ine in the liquid medium of Thalictrum minus cell suspension cultures. Plant Cell Rep 3:254–257
Orihara Y, Miyatake H, Furuya T (1991) Triglucosylation on the biotransformation of (+)-menthol by cultured cells of Eucaryptus perriniana. Phytochemistry 30:1843–1845
Paniego NB, Giuletti AM (1994) Artemisia annua L. dedifferentiated and differentiated cultures. Artemisinin production. Plant Cell Tissue Organ Cult 36:163–168
Papageorgiou VP, Assimopoulou AN, Couladouros EA, Hepworth D, Nicolaou KC (1999) The chemistry and biology of alkannin, shikonin, and related naphthazarin natural products. Angew Chem Int Ed 38:270–300
Park SU, Facchini PJ (2000) Agrobacterium rhizogenes—mediated transformation of opium poppy, Papaver somniferum L., and California poppy, Eschscholzia californica Cham., root cultures. J Exp Bot 347:1005–1016
Parr AJ, Peerless ACJ, Hamill JD, Walton NJ, Robins RJ, Rhodes MJC (1988) Alkaloid production by transformed root cultures of Catharanthus roseus. Plant Cell Rep 7:309–312
Payne J, Hamill JD, Robins RJ, Rhodes MJC (1987) Production of hyoscyamine by hairy root cultures of Datura stramonium. Planta Med 53:474–478
Puricelli L, Caniato R, Monache GD (2003) Biotransformation of a dibenzylbutanolide to podo-phyllotoxin analogues by shoot cultures of Haplophyllum patavinium. Chem Pharm Bull 51:848–850
Rohmer M (1999) The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae, and higher plants. Nat Prod Rep 16:565–574
Rao RS, Ravishankar GA (1999) Biotransformation of isoeugenol to vanilla flavour metabolites and capsaicin in freely suspended and immobilized cell cultures of Capsicum frutescens: study of the influence of β-cyclodextrin and fungal elicitor. Process Biochem 35:341–348
Saito K, Sudo H, Yamazaki M, Koseki-Nakamura M, Kitajima M, Takayama H, Aimi N (2001) Feasible production of camptothecin by hairy root culture of Ophiorrhiza pumila. Plant Cell Rep 20:267–271
Sakato K, Tanaka H, Mukai N, Misawa M (1974) Isolation and identification of camptothecin from cells of Camptotheca acuminata suspension cultures. Agric Biol Chem 38:217–218
Sato F, Yamada Y (1984) High berberine producing cultured Coptis japonica cells. Phytochemis-try 23:281–285
Seki H, Ohyama K, Sawai S, Mizutani M, Ohnishi T, Sudo H, Akashi T, Aoki T, Saito K, Muranaka T (2008) Licorice β-amyrin 11-oxidase, a cytochrome P450 with a key role in the biosynthesis of the triterpene sweetener glycyrrhizin. Proc Natl Acad Sci USA 105:14204–14209
Shibata S (2000) A drug over the millennia: pharmacognosy, chemistry, and pharmacology of licorice. Yakugaku Zasshi 120:849–862
Shimoda K, Kondo Y, Nishida T, Hamada H, Nakajima N, Hamada H (2006) Biotransformation of thymol, carvacrol, and eugenol by cultured cells of Eucalyptus perriniana. Phytochemistry 67:2256–2261
Shimoda K, Kwon S, Utsuki A, Ohiwa S, Katsuragi H, Yonemoto N, Hamada H, Hamada H (2007) Glycosylation of capsaicin and 8-nordihydrocapsaicin by cultured cells of Cathar-anthus roseus. Phytochemistry 68:1391–1396
Smetanska I (2008) Production of secondary metabolites using plant cell cultures. Adv Biochem Eng Biotechnol 111:187–228
Spieler H, Alfermann AW, Reinhard E (1985) Biotransformation of b-methyldigitoxin by cell cultures of Digitalis lanata in airlift and stirred tank reactors. Appl Microbiol Miotechnol 23:1–4
Suga T, Hirata T (1990) Biotransformation of exogeneous substrates by plant cell cultures. Phytochemistry 29:2393–2406
Tabata M, Yamamoto H, Hiraoka N, Konoshima M (1972) Organization and alkaloid production in tissue cultures of Scopolia parviflora. Phytochemistry 11:949–955
Tabata M, Mizukami H, Hiraoka N, Konoshima M (1974) Pigment formation of callus cultures of in Lithospermum erythrorhizon. Phytochemistry 13:927–932
Tabata M, Ikeda F, Hiraoka N, Konoshima M (1976) Glucosylation of phenolic compounds by Datura innoxia cell suspension cultures. Phytochemistry 15:1225–1229
Tabata M, Fujita Y (1985) Production of shikonin by plant cell cultures. In: Zaitlin M, Day P, Hollander A (eds) Biotechnology in Plant Science. Acad Press, Orland, pp 207–218
Tabata M (1996) The mechanism of shikonin biosynthesis in Lithospermum cell cultures. Plant Tissue Cult Lett 13:117–125
Tani M, Takeda K, Yazaki K, Tabata M (1993) Effects of oligogalacturonides on biosynthesis of shikonin in Lithospermum cell cultures. Phytochemistry 34:1285–1290
Tani Y, Fujioka T, Hamada H, Kunimatsu M, Furuichi Y (2003) Favorable effects of vanillylnonamide-b-D-glucoside on serum lipids in hyperlipidemic rats. J Jpn Soc Nutr Food Sci 56:181–187
Toivonen L, Balsevich J, Kurz WGW (1989) Indole alkaloid production by hairy root cultures of Catharanthus roseus. Plant Cell Tissue Organ Cult 18:79–93
Toivonen L, Rosenqvit H (1995) Establishment and growth characteristics of Glycyrrhiza glabra hairy root cultures. Plant Cell Tissue Organ Cult 41:249–258
Uomori A, Seo S, Tomita Y (1974) Studies on the constituents in tissue cultures of Bupleurum falcatum L. Syoyakugaku Zasshi 28:152–160
Waller GR, Nowacki EK (1978) Alkaloid Biology and Metabolism in Plant. Plenum Publ, New York, USA
Weathers PJ, Cheetham RD, Follansbee E, Teoh K (1994) Artemisinin production by transformed roots of Artemisia annua. Biotechnol Lett 16:1281–1286
Wildung MR, Croteau R (1996) A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis. J Biol Chem 271:9201–9204
Yamada Y, Endo T (1984) Tropane alkaloid production in cultured cells of Duboisia leichhardtii. Plant Cell Rep 3:186–188
Yamada Y, Hashimoto T (1982) Production of tropane alkaloids in cultured cells of Hyoscyamus niger. Plant Cell Rep 1:101–103
Yamamoto H, Zhao P, Yazaki K, Inoue K (2002) Regulation of lithospermic acid B and shikonin production in Lithospermum erythrorhizon cell suspension cultures. Chem Pharm Bull 50:1086–1090
Yamazaki Y, Sudo H, Yamazaki M, Aimi N, Saito K (2003) Camptothecin biosynthetic genes in hairy roots of Ophiorrhiza pumila: Cloning, characterization and differential expression in tissues and by stress compounds. Plant Cell Physiol 44:395–403
Yazaki K, Takeda K, Tabata M (1997) Effects of methyl jasmonate on shikonin and dihydroechi-nofuran production in Lithospermum cell cultures. Plant Cell Physiol 38:776–782
Yazaki K, Kunihisa M, Fujisaki T, Sato F (2002) Geranyl diphosphate: 4-hydroxybenzoate geranyltransferase from Lithospermum erythrorhizon. Cloning and characterization of a key enzyme in shikonin biosynthesis. J Biol Chem 277:6240–6246
Yamazaki Y, Kitajima M, Arita M, Takayama H, Sudo H, Yamazaki M, Aimi N, Saito K (2004) Biosynthesis of camptothecin. In silico and in vitro tracer study from [1-13C] glucose. Plant Physiol 134:161–170
Yokoyama M, Inomata S, Seto S, Yanagi M (1990) Effect of sugars on the glucosylation of exogenous hydroquinone by Catharanthus roseus cells in suspension culture. Plant Cell Physiol 31:551–555
Yukimune Y, Tabata H, Higashi Y, Hara Y (1996) Methyl jasmonate induced overproduction of paclitaxel and baccatin III in Taxus cell suspension cultures. Nat Biotechnol 14:1129–1132
Yun DJ, Hashimoto T, Yamada Y (1992) Metabolic engineering of medicinal plants: transgenic Atropa belladonna with an improved alkaloid composition. Proc Natl Acad Sci USA 89:11799–11803
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Mizukami, H., Hayashi, H. (2010). Biosynthesis and Biotransformation. In: Kole, C., Michler, C.H., Abbott, A.G., Hall, T.C. (eds) Transgenic Crop Plants. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-04809-8_9
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