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Taxus brevifolia a High-Value Medicinal Plant, as a Source of Taxol

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Medicinal and Aromatic Plants of North America

Part of the book series: Medicinal and Aromatic Plants of the World ((MAPW,volume 6))

Abstract

The genus Taxus has created considerable interest due to the presence of taxol. Taxol is one of the best-selling medicaments used in the treatment of ovarian, lung and breast cancers and Kaposi’s sarcoma. In this chapter, we briefly describe the current possibilities to produce the taxol from natural sources, synthetic approaches for taxol and its analogues, anticancer activity of taxol and secondary metabolites of T. brevifolia.

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References

  • Appendino G, Cravotto G, Enriu R, Gariboldi E, Barbo L, Torregiani E, Gabetta B, Zini G, Bombardelli E (1994) Taxoids from the Roots of Taxus × media cv. Hicksii. J Nat Prod 57:607–613

    Article  CAS  Google Scholar 

  • Arslanian RL, Bailey DT, Kent MC, Richheimer SL, Thornburg KR, Timmons DW, Zheng QY (1995) Brevitaxin, a new diterpenolignan from the bark of Taxus brevifolia. J Nat Prod 58:583–585

    Article  CAS  PubMed  Google Scholar 

  • Balza F, Tachibana S, Barrios H, Towers GHN (1991) Brevifoliol, a taxane from Taxus brevifolia. Phytochemistry 30:1613–1416

    Article  CAS  Google Scholar 

  • Barboni L, Gariboldi P, Torregiani E, Appendino G, Gabetta B, Bombardelli E (1994) Taxol analogues from the roots of Taxus x media. Phytochemistry 36:987–990

    Article  CAS  Google Scholar 

  • Beutler JA, Chmurny GM, Look SA, Witherup KM (1991) Taxinine M, a new tetracyclic taxane from Taxus brevifolia. J Nat Prod 54:893–897

    Article  CAS  PubMed  Google Scholar 

  • Bringi V, Kadkade PG, Prince CL, Roach BL (2007) Enhanced production of taxol and taxanes by cell cultures of Taxus species. US 7264951 B1 20070904

    Google Scholar 

  • Chen R, Kingston DGI (1994) Isolation and structure elucidation of new taxoids from Taxus brevifolia. J Nat Prod 57:1017–1021

    Article  CAS  PubMed  Google Scholar 

  • Chowdhary K, Jangir M, Sharma S (2017) Endosymbionts: a continuing source of cytotoxic metabolite taxol. Int J Adv Res 5:1–8

    Article  CAS  Google Scholar 

  • Christen AA, Bland J, Gibson DM (1989) Cell cultures as a means to produce Taxol. Proc Am Assoc Cancer Res 30:566

    Google Scholar 

  • Christen AA, Gibson DM, Bland J (1991) Production of Taxol or taxol-like compounds with Taxus brevifolia callus cell culture. US Patent No 5019504

    Google Scholar 

  • Chu A, Zajicek J, Davin LB, Lewis NG, Croteau RB (1992) Mixed acetoxy-benzoxy taxane esters from Taxus brevifolia. Phytochemistry 31:4249–4252

    Article  CAS  Google Scholar 

  • Chu A, Zajicek J, Towers GHN, Soucy-Breau CM, Lewis NG, Croteau R (1993a) Brevifoliol: A structure revision. Phytochemistry 34:269–271

    Google Scholar 

  • Chu A, Davin LB, Zajicek J, Lewis NG, Croteau R (1993b) Intramolecular acyl migrations in taxanes from Taxus brevifolia. Phytochemistry 34:473–476

    Google Scholar 

  • Chu A, Furlan M, Davin LB, Zajicek J, Towers GHN, Soucy-Breau CM, Rettig SJ, Croteau R, Lewis NG (1994) Phenylbutanoid and taxane-like metabolites from needles of Taxus brevifolia. Phytochemistry 36:975–985

    Article  CAS  Google Scholar 

  • Cragg GM, Schepartz SA, Suffness M, Grever MR (1993) The taxol supply crisis. New NCI policies for handling the large-scale production of novel natural product anticancer and anti-HIV agents. J Nat Prod 56:1657–1668

    Article  CAS  PubMed  Google Scholar 

  • Denis JN, Greene AE, Guenard D, Gueritte-Voegelein F, Mangatal L, Potier P (1988) A highly efficient, practical approach to natural taxol. J Am Chem Soc 110:5917–5919

    Article  CAS  Google Scholar 

  • Dumontet C, Sikic BI (1999) Mechanisms of action of and resistance to antitubulin agents: Microtubule dynamics, drug transport, and cell death. J Clin Oncol 17:1061–1061

    Article  CAS  PubMed  Google Scholar 

  • Fu Y, Li S, Zu Y, Yang G, Yang Z, Luo M, Jiang S, Wink M, Efferth T (2009) Medicinal chemistry of paclitaxel and its analogues. Curr Med Chem 16:3966–3985

    Article  CAS  PubMed  Google Scholar 

  • Fuchs DA, Johnson RK (1978) Cytologic evidence that taxol, an antineoplastic agent from Taxus brevifolia, acts as a mitotic spindle poison. Cancer Treat Rep 62:1219–1222

    CAS  PubMed  Google Scholar 

  • Fumoleau P, Seidman AD, Trudeau ME, Chevallier B, Ten Bokkel Huininik WW (1997) Docetaxel: a new active agent in the therapy of metastatic breast cancer. Expert Opin Investig Drugs 6:1853–1865

    Article  PubMed  Google Scholar 

  • Gan F, Zheng G, Peng L, Luo J (1997) Study on cell suspension culture of Taxus yunnanensis. Acta Phytophysiol Sinica 23:43–46

    Google Scholar 

  • Gueritte-Voegelein F, Guenard D, Lavelle F, LeGoff M-T, Mangatal L, Potier P (1991) Relationships between the structure of taxol analogues and their antimitotic activity. Jour. Med Chem 34:992–998

    Article  CAS  Google Scholar 

  • Hamburger M, Hostettmann K (1991) Bioactivity in plants: the link between phytochemistry and medicine. Phytochemistry 30:3864–3874

    Article  CAS  Google Scholar 

  • Henderson IC, Berry DA, Demetri GD, Cirrincione CT, Goldstein LJ, Martino S, Ingle JN, Cooper MR, Hayes DF, Tkaczuk KH, Fleming G, Holland JF, Duggan DB, Carpenter JT, Frei E, Schilsky RL, Wood WC, Muss HB, Norton L (2003) Improved outcomes from adding sequential paclitaxel but not from escalating doxorubicin dose in an adjuvant chemotherapy regimen for patients with node-positive primary breast cancer. J Clin Oncol 21:976–983

    Article  CAS  PubMed  Google Scholar 

  • Hoke SH, Cooks RG, Chang CJ, Kelly RC, Qualls SJ, Alvarado B, McGuire MT, Snader KM (1994) Determination of taxanes in Taxus bervifolia extracts by MS/MS and HPLC. J Nat Prod 57:277–286

    Article  CAS  PubMed  Google Scholar 

  • Holton RA, Somoza C, Kim HB, Liang F, Biediger RJ, Boatman PD, Shindo M, Smith CC, Kim S, Nadizadeh H, Suzuki Y, Tao C, Yu P, Tang S, Zhang P, Murthi KK, Gentile LN, Liu JH (1994) First total synthesis of Taxol. J Am Chem Soc 116:1597–1600

    Article  CAS  Google Scholar 

  • Horwitz SB (2004) Personal recollections on the early development of taxol. J Nat Prod 67:136–138

    Article  CAS  PubMed  Google Scholar 

  • Horwitz SB, Fant J, Schiff PB (1979) Promotion of microtubule assembly in vitro by taxol. Nature 277:665–667

    Article  PubMed  Google Scholar 

  • Hosie RC (1969) Native trees of Canada, 7th edn. Canadian Forestry Service, Department of Fisheries and Forestry, Ottawa, ON, 380 p

    Google Scholar 

  • Hu YM, Gan FY, Lu CH, Ding HS, Shen YM (2003) Production of taxol and related taxanes by cell suspension cultures of Taxus yunnanensis. Acta Bot Sin 45:373–378

    CAS  Google Scholar 

  • Huang CHO, Kingston DGI, Magri NF, Samaranayake G, Boettner FE (1986) New taxanes from Taxus brevifolia, 2. J Nat Prod 49:665–669

    Article  CAS  PubMed  Google Scholar 

  • Ji Y, Bi J-N, Yan B, Zhu X-D (2006) Taxol-producing fungi: A new approach to industrial production of taxol. Chin J Biotech 22:1–6

    Article  Google Scholar 

  • Ketchum REB, Luong JV, Gibson DM (1999) Efficient extraction of paclitaxel and related taxoids from leaf tissue of Taxus using a potable solvent system. J Liq Chromatog Related Tech 22:1715–1732

    Article  CAS  Google Scholar 

  • Kikuchi Y, Yatagai M (2003) The commercial cultivation of Taxus species and production of Taxoids. In: Itokawa H, Lee KH (eds) Taxus: the Genus Taxus. CRC Press, pp 151–178

    Google Scholar 

  • Kingston DGI, Hawkins DR, Ovington L (1982) New taxanes from Taxus brevifolia. J Nat Prod 45:466–470

    Article  CAS  PubMed  Google Scholar 

  • Li JY, Stroble G, Sidhu R, Hess WM, Ford EJ (1996) Endophytic taxol producing fungi from bald cypress, Taxodium distichum. Microbiology 142:2223–2226

    Article  CAS  PubMed  Google Scholar 

  • Little EL Jr (1979) Checklist of United States trees (native and naturalized). Agric. Handb. 541. U.S. Department of Agriculture, Forest Service, Washington, DC, 375 p

    Google Scholar 

  • Miele M, Anna Mumot AM, Zappa A, Romano P, Ottaggio L (2012) Hazel and other sources of paclitaxel and related compounds. Phytochem Rev 11:211–225

    Article  CAS  Google Scholar 

  • Morihira K, Hara R, Kawahara S, Nishimori T, Nakamura N, Kusama H, Kuwajima I (1998) Enantio-selective total synthesis of Taxol. J Am Chem Soc 120:12980–12981

    Article  CAS  Google Scholar 

  • Moss RW (1998) Herbs against Cancer: history and controversy Equinox Press Inc, 300 p

    Google Scholar 

  • Neto AGF, Di Cosmo F (1992) Distribution and amounts of taxol in different shoot parts of Taxus cuspidata. Planta Med 58:464–466

    Article  Google Scholar 

  • Nicolaou KC, Yang Z, Liu JJ, Ueno H, Nantermet PG, Guy RK, Claiborne CF, Renaud J, Couladouros EA, Paulvannan K (1994) Total synthesis of taxol. Nature 367:630–634

    Article  CAS  PubMed  Google Scholar 

  • Park YK, Chung ST, Row KH (1999) Preparative chromatographic separation of Taxol from yew trees. J Liq Chromatogr Related Technol 22:2577–2761

    Article  Google Scholar 

  • Preston RJ Jr (1948) North American trees. The Iowa State College Press, Amess, IA, 371 p

    Google Scholar 

  • Rao KV (1993) Taxol and related taxanes. I Taxanes of Taxus brevifolia bark. Pharm Res 10:521–524

    Article  CAS  PubMed  Google Scholar 

  • Rao K, Hanuman JB, Alvarez C, Stoy M, Juchum J, Davies RM, Baxley R (1995) A new large-scale process for taxol and related taxanes from Taxus brevifolia. Pharm Res 12:1003–1010

    Article  CAS  PubMed  Google Scholar 

  • Rao KV, Bhakuni RS, Hanuman JB, Davies R, Johnson J (1996) Taxanes from the bark of Taxus brevifolia. Phytochemistry 41:863–866

    Article  CAS  Google Scholar 

  • Rowinsky EK (1997) The development and clinical utility of the taxane class of anti-microtubule chemotherapy agents. Annu Rev Med 48:353–374

    Article  CAS  PubMed  Google Scholar 

  • Rowinsky EK, Onetto N, Canetta RM, Arbuck SG (1992) Taxol: the first of the taxanes, an important new class of anticancer agents. Semin Oncol 19:646–662

    CAS  PubMed  Google Scholar 

  • Senilh V, Blechert S, Colin M, Guenard D, Picot F, Potier P (1984) Mise en evidence de Nouveaux analogues du taxol extraits de Taxus baccata. J Nat Prod 47:131–137

    Article  CAS  Google Scholar 

  • Stierle A, Strobel G, Stierle D (1993) Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of pacific yew. Science 260:214–216

    Article  CAS  PubMed  Google Scholar 

  • Strobel G, Yang XS, Sears J, Kramer R, Sidhu RS, Hess WM (1996) Taxol from Pestalotiopsis microspora, an endophytic fungus of Taxus wallachiana. Microbiology 142:435–440

    Article  CAS  PubMed  Google Scholar 

  • Suffness M (1995) Taxol: Science and Applications. CRC Press, New York

    Google Scholar 

  • Theodoridis G, Verpoorte R (1996) Taxol analysis by high performance liquid chromatography: a review. Phytochem Anal 7:169–184

    Article  CAS  Google Scholar 

  • Tubiana-Hulin M (2005) How to maximize the efficacy of taxanes in breast cancer. Cancer Treat Rev 31:S3–S9

    Article  CAS  PubMed  Google Scholar 

  • Vaishampayan U, Parchment RE, Jasti BR, Hussain M (1999) Taxanes: an overview of the pharmacokinetics and pharmacodynamics. Urology 54:22–29

    Article  CAS  PubMed  Google Scholar 

  • Valero V, Jones SE, von Hoff DD, Booser DJ, Mennel RG, Ravdin PM, Holmes FA, Rahman Z, Schottstaedt MW, Erban JK, Esparza-Guerra L, Earhart RH, Hortobagyi GN, Burris HA 3rd. (1998) A phase II study of docetaxel in patients with paclitaxelresistant metastatic breast cancer. Jour Clin Oncol 16:3362–3368

    Article  CAS  Google Scholar 

  • Velde DGV, Georg GI, Gollapudi SR, Jampani HB, Liang X-Z, Mitscher LA, Ye Q-M (1994) Wallifoliol, a taxol congener with a novel carbon skeleton, from Himalayan Taxus wallichiana. J Nat Prod 37:862–867

    Article  Google Scholar 

  • Venook AP, Egorin MJ, Rosner GL, Brown TD, Jahan TM, Batist G, Hohl R, Budman D, Ratain MJ, Kearns CM, Schilsky RL (1998) Phase I and pharmacokinetic trial of paclitaxel in patients with hepatic dysfunction: Cancer and Leukemia Group B 9264. J Clin Oncol 16:1811–1819

    Article  CAS  PubMed  Google Scholar 

  • Verschraegen C, Sittisomwong T, Kudelka A, Guedes E, Steger M, Nelson-Taylor T, Vincent M, Rogers R, Atkinson E, Kavanagh J (2000) Docetaxel for patients with paclitaxel resistant Mullerian carcinoma. J Clin Oncol 18:2733–2739

    Article  CAS  PubMed  Google Scholar 

  • Verweij J, Clavel M, Chevalier B (1994) Paclitaxel (taxol) and docetaxel (Taxotere): not simply two of a kind. Ann Oncol 5:495–505

    Article  CAS  PubMed  Google Scholar 

  • Vidensek N, Lim P, Campbell A, Carlson C (1990) Taxol content in bark, wood, root, leaf, twig, and seedling from several Taxus species. J Nat Prod 53:1609–1615

    Article  CAS  PubMed  Google Scholar 

  • Wang JF, Li GL, Lu HY, Zheng ZH, Huang YJ, Su WJ (2000) Taxol from Tubercularia sp. strain TF5, an endophytic fungus of Taxus mairei. FEMS Microbiol Lett 193:249–253

    Article  CAS  PubMed  Google Scholar 

  • Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT (1971) Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 93:2325–2327

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Institute of the Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent, Uzbekistan

    N. Z. Mamadalieva

  2. Medicinal Plants Program, University of Massachusetts, Stockbridge School of Agriculture, Amherst, MA, USA

    N. A. Mamedov

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  1. N. Z. Mamadalieva
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  2. N. A. Mamedov
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Correspondence to N. A. Mamedov .

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  1. Faculty of Agriculture and Food Science, Széchenyi István University, Mosonmagyaróvar, Hungary

    Ákos Máthé

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Mamadalieva, N.Z., Mamedov, N.A. (2020). Taxus brevifolia a High-Value Medicinal Plant, as a Source of Taxol. In: Máthé, Á. (eds) Medicinal and Aromatic Plants of North America. Medicinal and Aromatic Plants of the World, vol 6. Springer, Cham. https://doi.org/10.1007/978-3-030-44930-8_9

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