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References

  1. Colegate SM, Dorling PR, Huxtable CR. 1979. A spectroscopic investigation of swainsonine: an alpha-mannosidase inhibitor isolated from Swainsona canescens. Aust. J. Chem. 32: 2257-2264.
    CrossRef
  2. Lu H, Wang SS, Zhou QW, Zhao YN, Zhao BY. 2012. Damage and control of major poisonous plants in the western grasslands of China - a review. Rangeland J. 34: 329-339.
    CrossRef
  3. Dorling PR, Huxtable CR, Colegate SM. 1980. Inhibition of lysosomal α-mannosidase by swainsonine, an indolizidine alkaloid isolated from Swainsona canescens. Biochem. J. 191: 649-651.
    Pubmed PMC CrossRef
  4. Tulsiani DR, Harris TM, Touster O. 1982. Swainsonine inhibits the biosynthesis of complex glycoproteins by inhibition of golgi mannosidase II. J. Biol. Chem. 257: 7936-7939.
    Pubmed
  5. Kang MS, Elbein AD. 1983. Mechanism of inhibition of jack bean α-mannosidase by swainsonine. Plant Physiol. 71: 551-554.
    Pubmed PMC CrossRef
  6. Hino M, Nakayama O, Tsurumi Y, Adachi K, Shibata T, Terano H, et al. 1985. Studies of an immunomodulator, swainsonine. I. Enhancement of immune response by swainsonine in vitro. J. Antibiot. 38: 926-935.
    Pubmed CrossRef
  7. Goss PE, Baptiste J, Fernandes B, Baker M, Dennis JW. 1994. A phase I study of swainsonine in patients with advanced malignancies. Cancer Res. 54: 1450-1457.
    Pubmed
  8. Hamaguchi J, Nakagawa H, Takahashi M, Kudo T, Kamiyama N, Sun B, et al. 2007. Swainsonine reduces 5fluorouracil tolerance in the multistage resistance of colorectal cancer cell lines. Mol. Cancer 6: 58.
    Pubmed PMC CrossRef
  9. Santos FM, Latorre AO, Hueza IM, Sanches DS, Lippi LL, Gardner DR, et al. 2011. Increased antitumor efficacy by the combined administration of swainsonine and cisplatin in vivo. Phytomedicine 18: 1096-1101.
    Pubmed CrossRef
  10. You N, Liu W, Wang T, Ji R, Wang X, Gong Z, et al. 2012. Swainsonine inhibits growth and potentiates the cytotoxic effect of paclitaxel in hepatocellular carcinoma in vitro and in vivo. Oncol. Rep. 28: 2091-2100.
    Pubmed CrossRef
  11. Singh D, Kaur G. 2014. The antileukaemic cell cycle regulatory activities of swainsonine purified from Metarhizium anisopliae fermentation broth. Nat. Prod. Res. 28: 2044-2047.
    Pubmed CrossRef
  12. Zou HQ, Xu F, Zhang ZY, Sun X. 1997. Research progress of a promising anti-cancer drug swainsonine. Chin. Tradit. Drugs 28: 437-439.
  13. Liu BY, Liu YJ, Yin HR, Chen XH. 1999. Inhibition effect of swainsonine on the growth and metastasis of gastric cancer in vivo. Chin. J. Oncol. 20: 168-170.
  14. Shi Y, Li M, Xu F. 1999. Research overview of the toxic component of locoweed, swainsonine. J. Chin. Med. 22: 47-49.
  15. Sun JY, Zhu MZ, Wang SW. 2006. Effects of swainsonine on apoptosis of the human gastric carcinoma cell SGC-7901. West China J. Pharmaceut. Sci. 15: 197-201.
  16. Liu W, Zhang XB, Li Y, Yang FZ, Xie RM. 2006. Anti-tumor and immune enhancement of swainsonine. NW Pharm. J. 6: 258-260.
  17. White SL, Nagai T, Akiyama SK, Reeves EJ, Grzegorzewski K, Olden K. 1991. Swainsonine stimulation of the proliferation and colony forming activity of murine bone marrow. Cancer Commun. 3: 83-91.
    Pubmed
  18. Klein J-LD, Roberts JD, George MD, Kurtzberg J, Breton P, Chermann JC, et al. 1999. Swainsonine protects both murine and human haematopoietic systems from chemotherapeutic toxicity. Br. J. Cancer 80: 87-95.
    Pubmed PMC CrossRef
  19. Rooprai HK, Kandanearatchi A, Maidment SL, Christidou M, Trillo-Pazos G, Dexter DT, et al. 2001. Evaluation of the effects of swainsonine, captopril, tangeretin and nobiletin on the biological behaviour of brain tumour cells in vitro. Neuropathol. Appl. Neurobiol. 27: 29-39.
    Pubmed CrossRef
  20. Molyneux RJ, James LF. 1982. Loco intoxication: indolizidine alkaloids of spotted locoweed (Astragalus lentiginosus). Science 216: 190-191.
    Pubmed CrossRef
  21. Schneider MJ, Ungemach FS, Broquist HP, Harris TM. 1983. (1S,2R,8R,8aR)-1,2,8-Trihydroxyoctahydroindolizine (swainsonine), an α-mannosidase inhibitor from Rhizoctonia leguminicola. Tetrahedron 39: 29-32.
    CrossRef
  22. Ali MH, Hough L, Richardson AC. 1984. A chiral synthesis of swainsonine from D-glucose. J. Chem. Soc. Chem. Commun. 7: 447-448.
    CrossRef
  23. Cao GR, Li SJ, Duan DX, Zhao XW, Molyneux RJ. 1989. The isolation and identification of toxic components from Oxytropis ochrocephala. J. Northwest A&F Univ. (Nat. Sci. Ed.) 17: 1-8.
  24. James LF, Elbein AD, Molyneux RJ, Warren CD. 1989. Swainsonine and Related Glycosidase Inhibitors. Iowa State Press, Ames, IA
  25. Molyneux RJ, Mckenzie RA, O’Sullivan BM, Elbein AD. 1995. Identification of the glycosidase inhibitors swainsonine and calystegine B2 in weir vine (Ipomoea sp. Q6 {af f . Calobra}) and correlation with toxicity. J. Nat. Prod. 58: 878-886.
    Pubmed CrossRef
  26. Colodel EM, Gardner DR, Zlotowski P, Driemeier D. 2002. Identification of swainsonine as a glycoside inhibitor responsible for Sida carpinifolia poisoning. Vet. Hum. Toxicol. 44: 177-178.
    Pubmed
  27. Braun K, Romero J, Liddell C, Creamer R. 2003. Production of swainsonine by fungal endophytes of locoweed. Mycol. Res. 107: 980-988.
    Pubmed CrossRef
  28. Dantas AFM, Riet-Correa F, Gardner DR, Medeiros RMT, Barros SS, Anjos BL, et al. 2007. Swainsonine-induced lysosomal storage disease in goats caused by the ingestion of Turbina cordata in Northeastern Brazil. Toxicon 49: 111-116.
    Pubmed CrossRef
  29. Cook D, Gardner DR, Ralphs MH, Pfister JA, Welch KD, Green BT. 2009. Swainsoninine concentrations and endophyte amounts of Undifilum oxytropis in different plant parts of Oxytropis sericea. J. Chem. Ecol. 35: 1272-1278.
    Pubmed CrossRef
  30. Lu H, Quan HY, Ren ZH, Wang S, Xue RX, Zhao BY. 2016. The genome of Undifilum oxytropis provides insights into swainsonine biosynthesis and locoism. Sci. Rep. 6: 30760.
    Pubmed PMC CrossRef
  31. Cook D, Donzelli BGG, Creamer R, Baucom DL, Gardner DR, Pan J, et al. 2017. Swainsonine biosynthesis genes in diverse symbiotic and pathogenic fungi. G3 (Bethesda) 7: 1971-1979.
    CrossRef
  32. Tong DW, Cao GR, Li SJ. 2001. Isolation and identification of swainsonine from Oxytropis kansuensis Bunge. J. Northwest Sci. Tech. Univ. Agric. Foresty 29: 295-298.
  33. Wardrop DJ, Bowen EG. 2011. Nitrenium ion-mediated alkene bis-cyclofunctionalization: total synthesis of (-)-swainsonine. Org. Lett. 13: 2376-2379.
    Pubmed PMC CrossRef
  34. Alhawatema MS, Sanogo S, Baucom DL, Creamer R. 2015. A search f or t he p hylogenetic r elationship o f the a scomycete Rhizoctonia leguminicola using genetic analysis. Mycopathologia 179: 381-389.
    Pubmed CrossRef
  35. Braun K, Romero J, Liddell C, Creamer R. 2003. Production of swainsonine by fungal endophytes of locoweed. Mycol. Res. 8: 980-988.
    CrossRef
  36. Cook D, Beaulieu WT, Mott IW, Riet-Correa F, Gardner DR, Grum D, et al. 2013. Production of the alkaloid swainsonine by a fungal endosymbiont of the Ascomycete order Chaetothyriales in the host Ipomoea carnea. J. Agric. Food Chem. 61: 3797-3803.
    Pubmed CrossRef
  37. Wickwire BM, Harris CM, Harris TM, Broquist HP. 1990. Pipecolic acid biosynthesis in Rhizoctonia leguminicola. I. The lysine saccharopine, δ-piperidine-6-carboxylic acid pathway. J. Biol. Chem. 265: 14742-14747.
    Pubmed
  38. Wickwire BM, Wagner C, Broquist HP. 1990. Pipecolic acid biosynthesis in Rhizoctonia leguminicola. II. Saccharopine oxidase: a unique flavin enzyme involved in pipecolic acid biosynthesis. J. Biol. Chem. 265: 14748-14753.
    Pubmed
  39. Sim KL, Perry D. 1997. Analysis of swainsonine and its early metabolic precursors in cultures of Metarhizium anisopliae. Glycoconj. J. 14: 661-668.
    Pubmed CrossRef
  40. Gough FJ, Elliott ES. 1956. Black-patch of red clover and other legumes caused by Rhizoctonia leguminicola sp. nov. Bull. West Virginia Agric. Exp. Stn. 387: 1-23.
  41. Crump MH, Smalley EB, Henning JN, Nichols RE. 1963. Mycotoxicosis in animals fed legume hay infested with Rhizoctonia leguminicola. J. Am. Vet. Med. Assoc. 143: 996-997.
    Pubmed
  42. Aust SD, Broquist HP. 1965. Isolation of a parasympathomimetic alkaloid of fungal origin. Nature 205: 204.
    Pubmed CrossRef
  43. Rainey DP, Smalley EB, Crump MH, Strong FM. 1965. Isolation of salivation factor from Rhizoctonia leguminicola on red clover hay. Nature 205: 203-204.
    CrossRef
  44. Croom WJ, Hagler WMJ, Frotschel MA, Johnson AD. 1995. The involvement of slaframine and swainsonine in slobbers syndrome: a review. J. Anim. Sci. 73: 1499-1508.
    Pubmed CrossRef
  45. Yang MQ, Cao GR. 1997. Toxicity, metabolism and use of swainsonine. Prog. Vet. Med. 18: 20-25.
  46. Guengerich FP, Snyder JJ, Broquist HP. 1973. Biosynthesis of slaframine, (1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizine, a parasympathomimetic alkaloid of fungal origin. I. Pipecolic acid and slaframine biogenesis. Biochemistry 12: 4264-4269.
    Pubmed CrossRef
  47. Broquist H. 1986. Slaframine and swainsonine, mycotoxins from Rhizoctonia leguminicola. Toxin Rev. 5: 241-252.
    CrossRef
  48. Harris CM, Schneider MJ, Ungemach FS, Hill JE, Harris TM. 1988. Biosynthesis of the toxic indolizidine alkaloids slaframine and swainsonine in Rhizoctonia leguminicola: metabolism of 1-hydroxyindolizidines. J. Am. Chem. Soc. 110: 940-949.
    CrossRef
  49. Guo HL, Ye BL, Yue YY, Chen QT, Fu CS. 1986. Three new species of Metarhizium. Acta Mycol. Sin. 5: 185-190.
  50. Liu AY. 1988. A new record species of the genus Pseudomonas. Acta Mycol. Sin. 7: 192.
  51. Tamerler C, Ullah M, Adlard MW, Keshavarz T. 1998. Effect of pH on physiology of Metarhizium anisopliae for production of swainsonine. FEMS. Microbiol. Lett. 168: 17-23.
    Pubmed CrossRef
  52. Sim KL, Perry D. 1995. Swainsonine production by Metarhizium anisopliae determined by means of an enzymatic assay. Mycol. Res. 99: 1078-1082.
    CrossRef
  53. Patrick M, Adlard MW, Keshavarz T. 1993. Production of an indolizidine alkaloid, swainsonine by the filamentous fungus, Metarhizium anisopliae. Biotechnol. Lett. 15: 997-1000.
    CrossRef
  54. Pryor BM, Creamer R, Shoemaker RA, McLain-Romero J, Hambleton S. 2009. Undifilum, a new genus for endophytic Embellisia oxytropis and parasitic Helminthosporium bornmuelleri on legumes. Botany 87: 178-194.
    CrossRef
  55. Oldrup E, McLain-Romero J, Padilla A, Moya A, Gardner D, Creamer R. 2010. Localization of endophytic Undifilum fungi in locoweed seed and influence of environmental parameters on a locoweed in vitro culture system. Botany 88: 512-521.
    CrossRef
  56. Lu H, Li GZ, Yang XW, Cao D, Xue RX, Quan HY, et al. 2014. Diversity of endophytic fungi from Oxytropis kansuensis. Chin. J. Vet. Sci. 34: 1094-1099.
  57. Cao DD, Lu H, Li XM, Guo YZ, Xue RX, Quan HY, et al. 2015. Isolation, identification and diversity analysis of fungal endophyte in Astragalus stritus. Acta Agrestia Sin. 23: 1252-1258.
  58. Cao DD, Lu H, Xue RX, Wang H, Quan HY, Zhao BY. 2016. Effect of different culturing temperature on isolation and diversity of fungal endophyte in Astragalus variabilis. Chin. J. Vet. Sci. 52: 41-44.
  59. Harris CM, Campbell BC, Molyneux RJ, Harris TM. 1988. Biosynthesis of swainsonine in the diablo locoweed (Astragalus oxyphysus). Tetrahedron Lett. 29: 4815-4818.
    CrossRef
  60. Ralphs MH, Creamer R, Baucom D, Gardner DR, Welsh SL, Graham JD, et al. 2008. Relationship between the endophyte Embellisia spp. and the toxic alkaloid swainsonine in major locoweed species (Astragalus and Oxytropis). J. Chem. Ecol. 34: 32-38.
    Pubmed CrossRef
  61. Cook D, Gardner DR, Pfister JA. 2014. Swainsoninecontaining plants and their relationship to endophytic fungi. J. Agric. Food Chem. 62: 7326-7334.
    Pubmed CrossRef
  62. Zhang LL. 2014. Study on synthesis of swainsonine from endophytic fungi Undifilum oxytropis. Ningxia University, Ningxia, China.
  63. Xue RX, Quan HY, Ren ZH, Lu H, Zhao BY. 2016. Analysis of secondary metabolites of Undifilum oxytropis from locoweeds. Prog.Vet. Med. 7: 64-70.
  64. Broquist HP. 1991. Lysine-pipecolic acid metabolic relationships in microbes and mammals. Annu. Rev. Nutr. 11: 435-448.
    Pubmed CrossRef
  65. Guptar N, Spenser ID. 1969. Biosynthesis of the piperidine nucleus. The mode of incorporation of lysine into pipecolic acid and into piperidine alkaloids. J. Biol. Chem. 244: 88-94.
  66. He M. 2006. Pipecolic acid in microbes: biosynthetic routes and enzymes. J. Ind. Microbiol. Biotechnol. 33: 401-407.
    Pubmed CrossRef
  67. Chang YF, Adams E. 1971. Induction of separate catabolic pathways for L- and D-lysine in Pseudomonas putida. Biochem. Biophys. Res. Commun. 45: 570-577.
    CrossRef
  68. Miller DL, Rodwell VW. 1971. Metabolism of basic amino acids in Pseudomonas putida. Catabolism of lysine by cyclic and acyclic intermediates. J. Biol. Chem. 246: 2758-2764.
    Pubmed
  69. Yang GD. 2012. Study on the Synthesis of Swainsonine of Locoweed Endophytic Fungi. Northwest A&F University, Yangling, Xi’an, China.
  70. Kinzel JJ, Bhattacharjee JK. 1979. Role of pipecolic acid in the biosynthesis of lysine in Rhodotorula glutinis. J. Bacteriol. 138: 410-417.
    Pubmed PMC
  71. Kurtz M, Bhattacharjee JK. 1975. Biosynthesis of lysine in Rhodotorula glutinis: role of pipecolic acid. J. Gen. Microbiol. 86: 103-110.
    Pubmed CrossRef
  72. Mukherjee S, Dawe AL, Creamer R. 2012. Potential role for saccharopine reductase in swainsonine metabolism in endophytic fungus, Undifilum oxytropis. Fungal Biol. 116: 902-909.
    Pubmed CrossRef
  73. Fujii T, Narita T, Agematu H, Agata N, Isshiki K. 2000. Characterization of L-lysine 6-aminotransferase and its structural gene from Flavobacterium lutescens IFO3084. J. Biochem. 128: 391-397.
    Pubmed CrossRef
  74. Naranjo L, Valmaseda EM, Banuelos O, Lopez P, Riano J, Casqueiro J, et al. 2001. Conversion of pipecolic acid into lysine in Penicillium chrysogenum requires pipecolate oxidase and saccharopine reductase: characterization of the Iys7 gene encoding saccharopine reductase. J. Bacteriol. 183: 7165-7172.
    Pubmed PMC CrossRef
  75. Su SY, Teng C, Zhang W, Chen M. 2013. Progress on type III polyketide synthase from bacteria. Agric. Sci. Technol. (Beijing) 15: 119-129.
  76. Bernhardt R. 2006. Cytochromes P450 as versatile biocatalysts. J. Biotechnol. 124: 128-145.
    Pubmed CrossRef

Related articles in JMB

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Article

Review

J. Microbiol. Biotechnol. 2017; 27(11): 1897-1906

Published online November 28, 2017 https://doi.org/10.4014/jmb.1709.09003

Copyright © The Korean Society for Microbiology and Biotechnology.

The Biosynthesis Pathway of Swainsonine, a New Anticancer Drug from Three Endophytic Fungi

Zhenhui Ren , Runjie Song , Shuai Wang , Haiyun Quan , Lin Yang , Lu Sun , Baoyu Zhao and Hao Lu *

College of Veterinary Medicine, Northwest A&F University, Yangling, Shaanxi 712100, P.R. China

Received: September 1, 2017; Accepted: October 12, 2017

Abstract

Swainsonine (SW) is the principal toxic ingredient of locoweed plants that causes locoism
characterized by a disorder of the nervous system. It has also received widespread attention in
the medical field for its beneficial anticancer and antitumor activities. Endophytic fungi,
Alternaria sect. Undifilum oxytropis isolated from locoweeds, the plant pathogen Slafractonia
leguminicola, and the insect pathogen Metarhizium anisopliae, produce swainsonine. Acquired
SW by biofermentation has a certain foreground and research value. This paper mainly
summarizes the local and foreign literature published thus far on the swainsonine
biosynthesis pathway, and speculates on the possible regulatory enzymes involved in the
synthesis pathway within these three fungi in order to provide a new reference for research on
swainsonine biosynthesis by endophytic fungi.

Keywords: Swainsonine, biosynthesis, Alternaria oxytropis, Slafractonia leguminicola, Metarhizium anisopliae

References

  1. Colegate SM, Dorling PR, Huxtable CR. 1979. A spectroscopic investigation of swainsonine: an alpha-mannosidase inhibitor isolated from Swainsona canescens. Aust. J. Chem. 32: 2257-2264.
    CrossRef
  2. Lu H, Wang SS, Zhou QW, Zhao YN, Zhao BY. 2012. Damage and control of major poisonous plants in the western grasslands of China - a review. Rangeland J. 34: 329-339.
    CrossRef
  3. Dorling PR, Huxtable CR, Colegate SM. 1980. Inhibition of lysosomal α-mannosidase by swainsonine, an indolizidine alkaloid isolated from Swainsona canescens. Biochem. J. 191: 649-651.
    Pubmed KoreaMed CrossRef
  4. Tulsiani DR, Harris TM, Touster O. 1982. Swainsonine inhibits the biosynthesis of complex glycoproteins by inhibition of golgi mannosidase II. J. Biol. Chem. 257: 7936-7939.
    Pubmed
  5. Kang MS, Elbein AD. 1983. Mechanism of inhibition of jack bean α-mannosidase by swainsonine. Plant Physiol. 71: 551-554.
    Pubmed KoreaMed CrossRef
  6. Hino M, Nakayama O, Tsurumi Y, Adachi K, Shibata T, Terano H, et al. 1985. Studies of an immunomodulator, swainsonine. I. Enhancement of immune response by swainsonine in vitro. J. Antibiot. 38: 926-935.
    Pubmed CrossRef
  7. Goss PE, Baptiste J, Fernandes B, Baker M, Dennis JW. 1994. A phase I study of swainsonine in patients with advanced malignancies. Cancer Res. 54: 1450-1457.
    Pubmed
  8. Hamaguchi J, Nakagawa H, Takahashi M, Kudo T, Kamiyama N, Sun B, et al. 2007. Swainsonine reduces 5fluorouracil tolerance in the multistage resistance of colorectal cancer cell lines. Mol. Cancer 6: 58.
    Pubmed KoreaMed CrossRef
  9. Santos FM, Latorre AO, Hueza IM, Sanches DS, Lippi LL, Gardner DR, et al. 2011. Increased antitumor efficacy by the combined administration of swainsonine and cisplatin in vivo. Phytomedicine 18: 1096-1101.
    Pubmed CrossRef
  10. You N, Liu W, Wang T, Ji R, Wang X, Gong Z, et al. 2012. Swainsonine inhibits growth and potentiates the cytotoxic effect of paclitaxel in hepatocellular carcinoma in vitro and in vivo. Oncol. Rep. 28: 2091-2100.
    Pubmed CrossRef
  11. Singh D, Kaur G. 2014. The antileukaemic cell cycle regulatory activities of swainsonine purified from Metarhizium anisopliae fermentation broth. Nat. Prod. Res. 28: 2044-2047.
    Pubmed CrossRef
  12. Zou HQ, Xu F, Zhang ZY, Sun X. 1997. Research progress of a promising anti-cancer drug swainsonine. Chin. Tradit. Drugs 28: 437-439.
  13. Liu BY, Liu YJ, Yin HR, Chen XH. 1999. Inhibition effect of swainsonine on the growth and metastasis of gastric cancer in vivo. Chin. J. Oncol. 20: 168-170.
  14. Shi Y, Li M, Xu F. 1999. Research overview of the toxic component of locoweed, swainsonine. J. Chin. Med. 22: 47-49.
  15. Sun JY, Zhu MZ, Wang SW. 2006. Effects of swainsonine on apoptosis of the human gastric carcinoma cell SGC-7901. West China J. Pharmaceut. Sci. 15: 197-201.
  16. Liu W, Zhang XB, Li Y, Yang FZ, Xie RM. 2006. Anti-tumor and immune enhancement of swainsonine. NW Pharm. J. 6: 258-260.
  17. White SL, Nagai T, Akiyama SK, Reeves EJ, Grzegorzewski K, Olden K. 1991. Swainsonine stimulation of the proliferation and colony forming activity of murine bone marrow. Cancer Commun. 3: 83-91.
    Pubmed
  18. Klein J-LD, Roberts JD, George MD, Kurtzberg J, Breton P, Chermann JC, et al. 1999. Swainsonine protects both murine and human haematopoietic systems from chemotherapeutic toxicity. Br. J. Cancer 80: 87-95.
    Pubmed KoreaMed CrossRef
  19. Rooprai HK, Kandanearatchi A, Maidment SL, Christidou M, Trillo-Pazos G, Dexter DT, et al. 2001. Evaluation of the effects of swainsonine, captopril, tangeretin and nobiletin on the biological behaviour of brain tumour cells in vitro. Neuropathol. Appl. Neurobiol. 27: 29-39.
    Pubmed CrossRef
  20. Molyneux RJ, James LF. 1982. Loco intoxication: indolizidine alkaloids of spotted locoweed (Astragalus lentiginosus). Science 216: 190-191.
    Pubmed CrossRef
  21. Schneider MJ, Ungemach FS, Broquist HP, Harris TM. 1983. (1S,2R,8R,8aR)-1,2,8-Trihydroxyoctahydroindolizine (swainsonine), an α-mannosidase inhibitor from Rhizoctonia leguminicola. Tetrahedron 39: 29-32.
    CrossRef
  22. Ali MH, Hough L, Richardson AC. 1984. A chiral synthesis of swainsonine from D-glucose. J. Chem. Soc. Chem. Commun. 7: 447-448.
    CrossRef
  23. Cao GR, Li SJ, Duan DX, Zhao XW, Molyneux RJ. 1989. The isolation and identification of toxic components from Oxytropis ochrocephala. J. Northwest A&F Univ. (Nat. Sci. Ed.) 17: 1-8.
  24. James LF, Elbein AD, Molyneux RJ, Warren CD. 1989. Swainsonine and Related Glycosidase Inhibitors. Iowa State Press, Ames, IA
  25. Molyneux RJ, Mckenzie RA, O’Sullivan BM, Elbein AD. 1995. Identification of the glycosidase inhibitors swainsonine and calystegine B2 in weir vine (Ipomoea sp. Q6 {af f . Calobra}) and correlation with toxicity. J. Nat. Prod. 58: 878-886.
    Pubmed CrossRef
  26. Colodel EM, Gardner DR, Zlotowski P, Driemeier D. 2002. Identification of swainsonine as a glycoside inhibitor responsible for Sida carpinifolia poisoning. Vet. Hum. Toxicol. 44: 177-178.
    Pubmed
  27. Braun K, Romero J, Liddell C, Creamer R. 2003. Production of swainsonine by fungal endophytes of locoweed. Mycol. Res. 107: 980-988.
    Pubmed CrossRef
  28. Dantas AFM, Riet-Correa F, Gardner DR, Medeiros RMT, Barros SS, Anjos BL, et al. 2007. Swainsonine-induced lysosomal storage disease in goats caused by the ingestion of Turbina cordata in Northeastern Brazil. Toxicon 49: 111-116.
    Pubmed CrossRef
  29. Cook D, Gardner DR, Ralphs MH, Pfister JA, Welch KD, Green BT. 2009. Swainsoninine concentrations and endophyte amounts of Undifilum oxytropis in different plant parts of Oxytropis sericea. J. Chem. Ecol. 35: 1272-1278.
    Pubmed CrossRef
  30. Lu H, Quan HY, Ren ZH, Wang S, Xue RX, Zhao BY. 2016. The genome of Undifilum oxytropis provides insights into swainsonine biosynthesis and locoism. Sci. Rep. 6: 30760.
    Pubmed KoreaMed CrossRef
  31. Cook D, Donzelli BGG, Creamer R, Baucom DL, Gardner DR, Pan J, et al. 2017. Swainsonine biosynthesis genes in diverse symbiotic and pathogenic fungi. G3 (Bethesda) 7: 1971-1979.
    CrossRef
  32. Tong DW, Cao GR, Li SJ. 2001. Isolation and identification of swainsonine from Oxytropis kansuensis Bunge. J. Northwest Sci. Tech. Univ. Agric. Foresty 29: 295-298.
  33. Wardrop DJ, Bowen EG. 2011. Nitrenium ion-mediated alkene bis-cyclofunctionalization: total synthesis of (-)-swainsonine. Org. Lett. 13: 2376-2379.
    Pubmed KoreaMed CrossRef
  34. Alhawatema MS, Sanogo S, Baucom DL, Creamer R. 2015. A search f or t he p hylogenetic r elationship o f the a scomycete Rhizoctonia leguminicola using genetic analysis. Mycopathologia 179: 381-389.
    Pubmed CrossRef
  35. Braun K, Romero J, Liddell C, Creamer R. 2003. Production of swainsonine by fungal endophytes of locoweed. Mycol. Res. 8: 980-988.
    CrossRef
  36. Cook D, Beaulieu WT, Mott IW, Riet-Correa F, Gardner DR, Grum D, et al. 2013. Production of the alkaloid swainsonine by a fungal endosymbiont of the Ascomycete order Chaetothyriales in the host Ipomoea carnea. J. Agric. Food Chem. 61: 3797-3803.
    Pubmed CrossRef
  37. Wickwire BM, Harris CM, Harris TM, Broquist HP. 1990. Pipecolic acid biosynthesis in Rhizoctonia leguminicola. I. The lysine saccharopine, δ-piperidine-6-carboxylic acid pathway. J. Biol. Chem. 265: 14742-14747.
    Pubmed
  38. Wickwire BM, Wagner C, Broquist HP. 1990. Pipecolic acid biosynthesis in Rhizoctonia leguminicola. II. Saccharopine oxidase: a unique flavin enzyme involved in pipecolic acid biosynthesis. J. Biol. Chem. 265: 14748-14753.
    Pubmed
  39. Sim KL, Perry D. 1997. Analysis of swainsonine and its early metabolic precursors in cultures of Metarhizium anisopliae. Glycoconj. J. 14: 661-668.
    Pubmed CrossRef
  40. Gough FJ, Elliott ES. 1956. Black-patch of red clover and other legumes caused by Rhizoctonia leguminicola sp. nov. Bull. West Virginia Agric. Exp. Stn. 387: 1-23.
  41. Crump MH, Smalley EB, Henning JN, Nichols RE. 1963. Mycotoxicosis in animals fed legume hay infested with Rhizoctonia leguminicola. J. Am. Vet. Med. Assoc. 143: 996-997.
    Pubmed
  42. Aust SD, Broquist HP. 1965. Isolation of a parasympathomimetic alkaloid of fungal origin. Nature 205: 204.
    Pubmed CrossRef
  43. Rainey DP, Smalley EB, Crump MH, Strong FM. 1965. Isolation of salivation factor from Rhizoctonia leguminicola on red clover hay. Nature 205: 203-204.
    CrossRef
  44. Croom WJ, Hagler WMJ, Frotschel MA, Johnson AD. 1995. The involvement of slaframine and swainsonine in slobbers syndrome: a review. J. Anim. Sci. 73: 1499-1508.
    Pubmed CrossRef
  45. Yang MQ, Cao GR. 1997. Toxicity, metabolism and use of swainsonine. Prog. Vet. Med. 18: 20-25.
  46. Guengerich FP, Snyder JJ, Broquist HP. 1973. Biosynthesis of slaframine, (1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizine, a parasympathomimetic alkaloid of fungal origin. I. Pipecolic acid and slaframine biogenesis. Biochemistry 12: 4264-4269.
    Pubmed CrossRef
  47. Broquist H. 1986. Slaframine and swainsonine, mycotoxins from Rhizoctonia leguminicola. Toxin Rev. 5: 241-252.
    CrossRef
  48. Harris CM, Schneider MJ, Ungemach FS, Hill JE, Harris TM. 1988. Biosynthesis of the toxic indolizidine alkaloids slaframine and swainsonine in Rhizoctonia leguminicola: metabolism of 1-hydroxyindolizidines. J. Am. Chem. Soc. 110: 940-949.
    CrossRef
  49. Guo HL, Ye BL, Yue YY, Chen QT, Fu CS. 1986. Three new species of Metarhizium. Acta Mycol. Sin. 5: 185-190.
  50. Liu AY. 1988. A new record species of the genus Pseudomonas. Acta Mycol. Sin. 7: 192.
  51. Tamerler C, Ullah M, Adlard MW, Keshavarz T. 1998. Effect of pH on physiology of Metarhizium anisopliae for production of swainsonine. FEMS. Microbiol. Lett. 168: 17-23.
    Pubmed CrossRef
  52. Sim KL, Perry D. 1995. Swainsonine production by Metarhizium anisopliae determined by means of an enzymatic assay. Mycol. Res. 99: 1078-1082.
    CrossRef
  53. Patrick M, Adlard MW, Keshavarz T. 1993. Production of an indolizidine alkaloid, swainsonine by the filamentous fungus, Metarhizium anisopliae. Biotechnol. Lett. 15: 997-1000.
    CrossRef
  54. Pryor BM, Creamer R, Shoemaker RA, McLain-Romero J, Hambleton S. 2009. Undifilum, a new genus for endophytic Embellisia oxytropis and parasitic Helminthosporium bornmuelleri on legumes. Botany 87: 178-194.
    CrossRef
  55. Oldrup E, McLain-Romero J, Padilla A, Moya A, Gardner D, Creamer R. 2010. Localization of endophytic Undifilum fungi in locoweed seed and influence of environmental parameters on a locoweed in vitro culture system. Botany 88: 512-521.
    CrossRef
  56. Lu H, Li GZ, Yang XW, Cao D, Xue RX, Quan HY, et al. 2014. Diversity of endophytic fungi from Oxytropis kansuensis. Chin. J. Vet. Sci. 34: 1094-1099.
  57. Cao DD, Lu H, Li XM, Guo YZ, Xue RX, Quan HY, et al. 2015. Isolation, identification and diversity analysis of fungal endophyte in Astragalus stritus. Acta Agrestia Sin. 23: 1252-1258.
  58. Cao DD, Lu H, Xue RX, Wang H, Quan HY, Zhao BY. 2016. Effect of different culturing temperature on isolation and diversity of fungal endophyte in Astragalus variabilis. Chin. J. Vet. Sci. 52: 41-44.
  59. Harris CM, Campbell BC, Molyneux RJ, Harris TM. 1988. Biosynthesis of swainsonine in the diablo locoweed (Astragalus oxyphysus). Tetrahedron Lett. 29: 4815-4818.
    CrossRef
  60. Ralphs MH, Creamer R, Baucom D, Gardner DR, Welsh SL, Graham JD, et al. 2008. Relationship between the endophyte Embellisia spp. and the toxic alkaloid swainsonine in major locoweed species (Astragalus and Oxytropis). J. Chem. Ecol. 34: 32-38.
    Pubmed CrossRef
  61. Cook D, Gardner DR, Pfister JA. 2014. Swainsoninecontaining plants and their relationship to endophytic fungi. J. Agric. Food Chem. 62: 7326-7334.
    Pubmed CrossRef
  62. Zhang LL. 2014. Study on synthesis of swainsonine from endophytic fungi Undifilum oxytropis. Ningxia University, Ningxia, China.
  63. Xue RX, Quan HY, Ren ZH, Lu H, Zhao BY. 2016. Analysis of secondary metabolites of Undifilum oxytropis from locoweeds. Prog.Vet. Med. 7: 64-70.
  64. Broquist HP. 1991. Lysine-pipecolic acid metabolic relationships in microbes and mammals. Annu. Rev. Nutr. 11: 435-448.
    Pubmed CrossRef
  65. Guptar N, Spenser ID. 1969. Biosynthesis of the piperidine nucleus. The mode of incorporation of lysine into pipecolic acid and into piperidine alkaloids. J. Biol. Chem. 244: 88-94.
  66. He M. 2006. Pipecolic acid in microbes: biosynthetic routes and enzymes. J. Ind. Microbiol. Biotechnol. 33: 401-407.
    Pubmed CrossRef
  67. Chang YF, Adams E. 1971. Induction of separate catabolic pathways for L- and D-lysine in Pseudomonas putida. Biochem. Biophys. Res. Commun. 45: 570-577.
    CrossRef
  68. Miller DL, Rodwell VW. 1971. Metabolism of basic amino acids in Pseudomonas putida. Catabolism of lysine by cyclic and acyclic intermediates. J. Biol. Chem. 246: 2758-2764.
    Pubmed
  69. Yang GD. 2012. Study on the Synthesis of Swainsonine of Locoweed Endophytic Fungi. Northwest A&F University, Yangling, Xi’an, China.
  70. Kinzel JJ, Bhattacharjee JK. 1979. Role of pipecolic acid in the biosynthesis of lysine in Rhodotorula glutinis. J. Bacteriol. 138: 410-417.
    Pubmed KoreaMed
  71. Kurtz M, Bhattacharjee JK. 1975. Biosynthesis of lysine in Rhodotorula glutinis: role of pipecolic acid. J. Gen. Microbiol. 86: 103-110.
    Pubmed CrossRef
  72. Mukherjee S, Dawe AL, Creamer R. 2012. Potential role for saccharopine reductase in swainsonine metabolism in endophytic fungus, Undifilum oxytropis. Fungal Biol. 116: 902-909.
    Pubmed CrossRef
  73. Fujii T, Narita T, Agematu H, Agata N, Isshiki K. 2000. Characterization of L-lysine 6-aminotransferase and its structural gene from Flavobacterium lutescens IFO3084. J. Biochem. 128: 391-397.
    Pubmed CrossRef
  74. Naranjo L, Valmaseda EM, Banuelos O, Lopez P, Riano J, Casqueiro J, et al. 2001. Conversion of pipecolic acid into lysine in Penicillium chrysogenum requires pipecolate oxidase and saccharopine reductase: characterization of the Iys7 gene encoding saccharopine reductase. J. Bacteriol. 183: 7165-7172.
    Pubmed KoreaMed CrossRef
  75. Su SY, Teng C, Zhang W, Chen M. 2013. Progress on type III polyketide synthase from bacteria. Agric. Sci. Technol. (Beijing) 15: 119-129.
  76. Bernhardt R. 2006. Cytochromes P450 as versatile biocatalysts. J. Biotechnol. 124: 128-145.
    Pubmed CrossRef