$\require{mediawiki-texvc}$

연합인증

연합인증 가입 기관의 연구자들은 소속기관의 인증정보(ID와 암호)를 이용해 다른 대학, 연구기관, 서비스 공급자의 다양한 온라인 자원과 연구 데이터를 이용할 수 있습니다.

이는 여행자가 자국에서 발행 받은 여권으로 세계 각국을 자유롭게 여행할 수 있는 것과 같습니다.

연합인증으로 이용이 가능한 서비스는 NTIS, DataON, Edison, Kafe, Webinar 등이 있습니다.

한번의 인증절차만으로 연합인증 가입 서비스에 추가 로그인 없이 이용이 가능합니다.

다만, 연합인증을 위해서는 최초 1회만 인증 절차가 필요합니다. (회원이 아닐 경우 회원 가입이 필요합니다.)

연합인증 절차는 다음과 같습니다.

최초이용시에는
ScienceON에 로그인 → 연합인증 서비스 접속 → 로그인 (본인 확인 또는 회원가입) → 서비스 이용

그 이후에는
ScienceON 로그인 → 연합인증 서비스 접속 → 서비스 이용

연합인증을 활용하시면 KISTI가 제공하는 다양한 서비스를 편리하게 이용하실 수 있습니다.

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

Journal of microbiology and biotechnology, v.27 no.11, 2017년, pp.1897 - 1906  

Ren, Zhenhui (College of Veterinary Medicine, Northwest A&F University) ,  Song, Runjie (College of Veterinary Medicine, Northwest A&F University) ,  Wang, Shuai (College of Veterinary Medicine, Northwest A&F University) ,  Quan, Haiyun (College of Veterinary Medicine, Northwest A&F University) ,  Yang, Lin (College of Veterinary Medicine, Northwest A&F University) ,  Sun, Lu (College of Veterinary Medicine, Northwest A&F University) ,  Zhao, Baoyu (College of Veterinary Medicine, Northwest A&F University) ,  Lu, Hao (College of Veterinary Medicine, Northwest A&F University)

Abstract AI-Helper 아이콘AI-Helper

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. Undif...

주제어

AI 본문요약
AI-Helper 아이콘 AI-Helper

* AI 자동 식별 결과로 적합하지 않은 문장이 있을 수 있으니, 이용에 유의하시기 바랍니다.

가설 설정

  • anisopliae as well as some key enzymes that regulate SW synthesis. Combining the genome sequencing and functional analysis of A. oxytropis [30], we hypothesize the early steps of the SW biosynthesis pathway in A.oxytropis and some key enzymes that may be involved in the regulation of its synthesis. Production of a mutant A.
  • [59] found SW and the precursors of SW synthesis in locoweed (Astragalus oxyphysus) through the isotopic tracer method and preliminarily discussed the synthesis mechanism of SW. They hypothesized that the SW synthesis pathway from locoweed plants was similar to that from S.leguminicola and M.anisopliae. A.
본문요약 정보가 도움이 되었나요?

참고문헌 (76)

  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. 

  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. 

  3. Dorling PR, Huxtable CR, Colegate SM. 1980. Inhibition of lysosomal ${\alpha}$ -mannosidase by swainsonine, an indolizidine alkaloid isolated from Swainsona canescens. Biochem. J. 191:649-651. 

  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. 

  5. Kang MS, Elbein AD. 1983. Mechanism of inhibition of jack bean ${\alpha}$ -mannosidase by swainsonine. Plant Physiol. 71: 551-554. 

  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. 

  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. 

  8. Hamaguchi J, Nakagawa H, Takahashi M, Kudo T, Kamiyama N, Sun B, et al. 2007. Swainsonine reduces 5-fluorouracil tolerance in the multistage resistance of colorectal cancer cell lines. Mol. Cancer 6: 58. 

  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. 

  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. 

  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. 

  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. 

  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. 

  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. 

  20. Molyneux RJ, James LF. 1982. Loco intoxication: indolizidine alkaloids of spotted locoweed (Astragalus lentiginosus). Science 216: 190-191. 

  21. Schneider MJ, Ungemach FS, Broquist HP, Harris TM. 1983. (1S,2R,8R,8aR)-1,2,8-Trihydroxyoctahydroindolizine (swainsonine), an ${\alpha}$ -mannosidase inhibitor from Rhizoctonia leguminicola. Tetrahedron 39: 29-32. 

  22. Ali MH, Hough L, Richardson AC. 1984. A chiral synthesis of swainsonine from D-glucose. J. Chem. Soc. Chem. Commun. 7: 447-448. 

  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. 

  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. 

  27. Braun K, Romero J, Liddell C, Creamer R. 2003. Production of swainsonine by fungal endophytes of locoweed. Mycol. Res. 107: 980-988. 

  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. 

  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. 

  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. 

  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. 

  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. 

  34. Alhawatema MS, Sanogo S, Baucom DL, Creamer R. 2015. A search for the phylogenetic relationship of the a scomycete Rhizoctonia leguminicola using genetic analysis. Mycopathologia 179: 381-389. 

  35. Braun K, Romero J, Liddell C, Creamer R. 2003. Production of swainsonine by fungal endophytes of locoweed. Mycol. Res. 8: 980-988. 

  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. 

  37. Wickwire BM, Harris CM, Harris TM, Broquist HP. 1990. Pipecolic acid biosynthesis in Rhizoctonia leguminicola. I. The lysine saccharopine, ${\delta}$ -piperidine-6-carboxylic acid pathway. J. Biol. Chem. 265: 14742-14747. 

  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. 

  39. Sim KL, Perry D. 1997. Analysis of swainsonine and its early metabolic precursors in cultures of Metarhizium anisopliae. Glycoconj. J. 14: 661-668. 

  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. 

  42. Aust SD, Broquist HP. 1965. Isolation of a parasympathomimetic alkaloid of fungal origin. Nature 205: 204. 

  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. 

  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. 

  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. 

  47. Broquist H. 1986. Slaframine and swainsonine, mycotoxins from Rhizoctonia leguminicola. Toxin Rev. 5: 241-252. 

  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. 

  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. 

  52. Sim KL, Perry D. 1995. Swainsonine production by Metarhizium anisopliae determined by means of an enzymatic assay. Mycol. Res. 99: 1078-1082. 

  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. 

  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. 

  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. 

  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. 

  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. 

  61. Cook D, Gardner DR, Pfister JA. 2014. Swainsoninecontaining plants and their relationship to endophytic fungi. J. Agric. Food Chem. 62: 7326-7334. 

  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. 

  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. 

  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. 

  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. 

  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. 

  71. Kurtz M, Bhattacharjee JK. 1975. Biosynthesis of lysine in Rhodotorula glutinis: role of pipecolic acid. J. Gen. Microbiol. 86: 103-110. 

  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. 

  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. 

  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. 

  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. 

관련 콘텐츠

오픈액세스(OA) 유형

GOLD

오픈액세스 학술지에 출판된 논문

이 논문과 함께 이용한 콘텐츠

저작권 관리 안내
섹션별 컨텐츠 바로가기

AI-Helper ※ AI-Helper는 오픈소스 모델을 사용합니다.

AI-Helper 아이콘
AI-Helper
안녕하세요, AI-Helper입니다. 좌측 "선택된 텍스트"에서 텍스트를 선택하여 요약, 번역, 용어설명을 실행하세요.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.

선택된 텍스트

맨위로