696
Views
0
CrossRef citations to date
0
Altmetric
Review Article

Advances in the Extraction, Purification and Detection of the Natural Product 1-Deoxynojirimycin

, , , , & ORCID Icon
Pages 246-257 | Published online: 08 Jan 2020

References

  • Yagi, M.; Kouno, T.; Aoyagi, Y.; Murai, H. The Structure of Moraoline, a Piperidine Alkaloid from Morus Species. J. Agric. Chem. Soc. Jpn. 1976, 50, 571–572. DOI: 10.1271/nogeikagaku1924.50.11_571.
  • Song, W.; Wang, H. J.; Bucheli, P.; Zhang, P. F.; Wei, D. Z.; Lu, Y. H. Phytochemical Profiles of Different Mulberry (Morus sp.) Species from China. J. Agric. Food Chem. 2009, 57, 9133–9140. DOI: 10.1021/jf9022228.
  • Daimon, T.; Taguchi, T.; Meng, Y.; Katsuma, S.; Mita, K.; Shimada, T. Beta-Fructofuranosidase Genes of the Silkworm, Bombyx mori: Insights into Enzymatic Adaptation of B. mori to Toxic Alkaloids in Mulberry Latex. J. Biol. Chem. 2008, 28, 15271–15279. DOI: 10.1074/jbc.M709350200.
  • Asano, N.; Nishida, M.; Miyauchi, M.; Ikeda, K.; Yamamoto, M.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J. Polyhydroxylated Pyrrolidine and Piperidine Alkaloids from Adenophora Triphylla Var. japonica (Campanulaceae). Phytochemistry 2000, 53, 379–382. DOI: 10.1016/S0031-9422(99)00555-5.
  • Inouye, S.; Tsuruoka, T.; Ito, J.; Niida, T. Structure and Synthesis of Nojirimycin. Tetrahedron 1968, 24, 2125–2144. DOI: 10.1016/0040-4020(68)88115-3.
  • Ezure, Y.; Ojima, N.; Konno, K.; Miyazaki, K.; Yamada, N.; Sugiyama, M.; Toh, M.; Nakamura, T. Isolation of 1,5-Dideoxy-1,5-imino-D-Mannitol from Culture Broth of Streptomyces Species. J. Antibiot. 1988, 41, 1142–1144. DOI: 10.7164/antibiotics.41.1142.
  • Robson, W. Physiological and Genetic Studies of Deoxynojirimycin Production in Streptomyces Species, in Department of Biological Science. University of Warwick, Coventry, UK, 1993, p. 253.
  • Stein, D.; C.; Kopec, L. K.; Yasbin, R. E.; Young, F. E. Characterization of Bacillus subtilis DSM704 and Its Production of 1-Deoxynojirimycin. Appl. Environ. Microb. 1984, 48, 280–284. DOI: 10.1016/0141-4607(84)90089-1.
  • Nakagawa, K.; Kubota, H.; Tsuzuki, T.; Kariya, J.; Kimura, T.; Oikawa, S.; Miyazawa, T. Validation of an Ion Trap Tandem Mass Spectrometric Analysis of Mulberry 1-Deoxynojirimycin in Human Plasma: Application to Pharmacokinetic Studies. Biosci. Biotechnol. Biochem. 2008, 72, 2210–2213. DOI: 10.1271/bbb.80200.
  • Deng, M. J.; Lin, X. D.; Wen, C. W.; Dong, M. J.; Lin, Q. T.; Zhang, S. Z.; Xu, J. P. Metabolic Changes in the Midgut of Eri Silkworm after Oral Administration of 1-Deoxynojirimycin: A 1H-NMR-Based Metabonomic Study. PloS One 2017, 13, e0191080. DOI: 10.1371/journal.pone.0173213.
  • Zhang, S. Z.; Yu, H. Z.; Deng, M. J.; Ma, Y.; Fei, D. Q.; Wang, J.; Li, Z.; Meng, Y.; Xu, J. P. Comparative Transcriptome Analysis Reveals Significant Metabolic Alterations in Eri-Silkworm (Samia Cynthia Ricini) Haemolymph in Response to 1-Deoxynojirimycin. PLoS One 2018, 13, e0191080. DOI: 10.1371/journal.pone.0191080.
  • Legler, G. Glycoside Hydrolases: Mechanistic Information from Studies with Reversible and Irreversible Inhibitors. Cheminform 1990, 22, 319–384. DOI: 10.1002/chin.199125293.
  • Asano, N.; Kizu, H.; Oseki, K.; Tomioka, E.; Matsui, K.; Okamoto, M.; Baba, M. N-Alkylated Nitrogen-in-the-Ring Sugars: Conformational Basis of Inhibition of Glycosidases and HIV-1 Replication. J. Med. Chem. 1995, 38, 2349–2356. DOI: 10.1021/jm00013a012.
  • Watson, A. A.; Fleet, G. W. J.; Asano, N.; Molyneux, R. J.; Nash, R. J. Polyhydroxylated Alkaloids - Natural Occurrence and Therapeutic Applications. Phytochemistry 2001, 56, 265–295. DOI: 10.1016/S0031-9422(00)00451-9.
  • Li, Y. G.; Ji, D. F.; Zhong, S.; Lin, T. B.; Lv, Z. Q.; Hu, G. Y.; Wang, X. 1-deoxynojirimycin Inhibits Glucose Absorption and Accelerates Glucose Metabolism in Streptozotocin-Induced Diabetic Mice. Sci. Rep. 2013, 3, 1337. DOI: 10.1038/srep01377.
  • Zhao, Q.; Jia, T. Z.; Cao, Q. C.; Tian, F.; Ying, W. T. A Crude 1-DNJ Extract from Home Made Bombyx Batryticatus Mori. L. inhibits Diabetic Cardiomyopathy-Associated Fibrosis in db/db Mice and Reduces Protein N-Glycosylation Levels. IJMS. 2018, 19, 1699. DOI: 10.20944/preprints201804.0350.v1.
  • Do, H. J.; Chung, J. H.; Hwang, J. W.; Kim, O. Y.; Lee, J. Y.; Shin, M. J. 1-deoxynojirimycin Isolated from Bacillus subtilis Improves Hepatic Lipid Metabolism and Mitochondrial Function in High-Fat-Fed Mice. Food Chem. Toxicol. 2015, 75, 1–7. DOI: 10.1016/j.fct.2014.11.001.
  • Kim, J.; Yun, E. Y.; Quan, F. S.; Park, S. W.; Goo, T. W. Central Administration of 1-Deoxynojirimycin Attenuates Hypothalamic Endoplasmic Reticulum Stress and Regulates Food Intake and Body Weight in Mice with High-Fat Diet-Induced Obesity. Evid. Based Complement Altern. Med. 2017, 2017, 1– DOI: 10.11-55/2017/3607089.
  • Moscona, A. Neuraminidase Inhibitors for Influenza. N Engl. J. Med. 2005, 353, 1363–1373. DOI: 10.1056/NEJMra050740.
  • Jacob, G. S. Glycosylation Inhibitors in Biology and Medicine. Curr. Opin. Struct. Biol. 1995, 5, 605–611. DOI: 10.1016/0959-440X(95)80051-4.
  • Shuang, E.; Kazushi, Y.; Yu, S.; Yui, M.; Yui, I.; Toshiyuki, K.; Kiyotaka, N.; Teruo, M.; Tsuyoshi, T. Intake of Mulberry 1-Deoxynojirimycin Prevents Colorectal Cancer in Mice. J. Clin. Biochem. Nutr. 2017, 61, 47–52. DOI: 10.3164/jcbn.16.
  • Maruo, S.; Yamashita, H.; Miyazaki, K.; Yamamoto, H.; Kyotani, Y.; Ogawa, H.; Kojima, M.; Ezure, Y. A Novel and Efficient Method for Enzymatic Synthesis of High Purity Maltose Using Moranoline (1-Deoxynojirimycin). Biosci. Biotechnol. Biochem. 1992, 56, 1406–1409. DOI: 10.1271/bbb.56.1406.
  • Maruo, S.; Yamamoto, H.; Toda, M.; Tachikake, N.; Kojima, M.; Ezure, Y. Enzymatic Synthesis of High Purity Maltotetraose Using Moranoline(1-Deoxynojirimycin). Biosci. Biotechnol. Biochem. 1993, 57, 499–501. DOI: ttp://joi.jlc.jst.go.jp/JST.Journalarchive/bbb1992/57.499?from = CrossRef.
  • Guo, S. Q.; Cui, Y. L.; Wang, K. B.; Zhang, W.; Tan, G. Y.; Wang, B. M.; Cui, L. W. Development of a Specific Monoclonal Antibody for the Quantification of Artemisinin in Artemisia Annua and Rat Serum. Anal. Chem. 2016, 88, 2701–2706. DOI: 10.1021/acs.analchem.5b04058.
  • Gao, K.; Zheng, C. L.; Wang, T.; Zhao, H. H.; Wang, J.; Wang, Z. Y.; Zhai, X.; Jia, Z. J.; Chen, J. X.; Zhou, Y. W.; Wang, W. 1-Deoxynojirimycin: Occurrence, Extraction, Chemistry, Oral Pharmacokinetics, Biological Activities and in Silico Target Fishing. Molecules 2016, 21, 1600. DOI: 10.3390/molecules21111600.
  • Wagner, H.; Ulrich-Merzenich, G. Evidence and Rational Based Research on Chinese Drugs; Springer: Wien, 2013; Vol. xii, p. 525. DOI: 10.1007/978-3-7091-0442-2.
  • Banerjee, G.; Chattopadhyay, P. Vanillin Biotechnology: The Perspectives and Future. J. Sci. Food Agric. 2019, 99, 499–506. DOI: 10.1002/jsfa.9303.
  • Yu, X.; Che, Z. P.; Xu, H. Recent Advances in the Chemistry and Biology of Podophyllotoxins. Chem. Eur. J. 2017, 23, 4467–4526. DOI: 10.1002/chem.201602472.
  • Zheng, Y. W.; Hong, D. Y. Flora of China; Science Press: China, 2010.
  • Kinast, G.; Schedel, M. A Four-Step Synthesis of 1-Deoxynojirimycin with a Biotransforrnation as Cardinal Reaction Step. Angew. Chem. Int. Ed. Engl. 1981, 20, 805–806. DOI: 10.1002/anie.198108051.
  • Paulsen, H.; Sangster, I.; Heyns, K. Syntheses and Reaktionen Von Keto-Piperdinosen. Chem. Ber. 1967, 100, 802–1001. DOI: 10.1002/cber.19671000314.
  • Kinast, G.; Schedel, M. Production of N-Substituted Derivatives of 1-Deoxy-Nojirimycin, U.S. Patent 4,266,025. 1981.
  • Alexander, S.; Franz, E.; Peter, F. Aldolase-Catalyzed C-C Bond Formation for Stereoselective Synthesis of Nitrogen-Containing Carbohydrates. J. Org. Chem. 1990, 55, 3926–3932. DOI: http://dx.doi.org/10.18419/opus-1124.
  • Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Polyhydroxylated Piperidines and Azepanes from D-Mannitol - Synthesis of 1-Deoxynojirimycin and Analogs. Tetrahedron Lett. 1994, 35, 3293–3296. DOI: 10.1016/S0040-4039(00)76888-2.
  • Seo, M. J.; Nam, Y. D.; Lee, S. Y.; Park, S. L.; Yi, S. H.; Lim, S. I. Isolation of the Putative Biosynthetic Gene Cluster of 1-Deoxynojirimycin by Bacillus amyloliquefaciens 140N, Its Production and Application to the Fermentation of Soybean Paste. Biosci. Biotechnol. Biochem. 2013, 77, 398–401. DOI: 10.1271/bbb.120753.
  • Jiang, P. X.; Mu, S. S.; Li, H.; Li, Y. H.; Feng, C. M.; Jin, J. M.; Tang, S. Y. Design and Application of a Novel High-Throughput Screening Technique for 1-Deoxynojirimycin. Sci. Rep. 2015, 5, 8563. DOI: 10.1038/srep08563.
  • Rayamajhi, V.; Dhakal, D.; Chaudhary, A. K.; Sohng, J. K. Improved Production of 1-Deoxynojirymicin in Escherichia coli through Metabolic Engineering. World J. Microbiol. Biotechnol. 2018, 34, 77. DOI: 10.1007/s11274-018-2462-3.
  • Kang, K. D.; Cho, Y. S.; Song, J. H.; Park, Y. S.; Lee, J. Y.; Hwang, K. Y.; Rhee, S. K.; Chung, J. H.; Kwon, O.; Seong, S. I. Identification of the Genes Involved in 1-Deoxynojirimycin Synthesis in Bacillus subtilis MORI 3K-85. J. Microbiol. 2011, 49, 431–440. DOI: 10.1007/s12275-011-1238-3.
  • Wang, D.; Zhao, L.; Wang, D.; Liu, J.; Yu, X.; Wei, Y.; Ouyang, Z. Transcriptome Analysis and Identification of Key Genes Involved in 1-Deoxynojirimycin Biosynthesis of Mulberry (Morus Alba L.). PeerJ. 2018, 6, e5443. DOI: 10.7717/peerj.5443.
  • Asano, N.; Kato, A.; Miyauchi, M.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J. Nitrogen-Containing Furanose and Pyranose Analogues from Hyacinthus Orientalis. J. Nat. Prod. 1998, 61, 625–628. DOI: 10.1021/np9705726.
  • Shibano, M.; Fujimoto, Y.; Kushino, K.; Kusano, G.; Baba, K. Biosynthesis of 1-Deoxynojirimycin in Commelina Communis: A Difference between the Microorganisms and Plants. Phytochemistry 2004, 65, 2661–2665. DOI: 10.1016/j.phytochem.2004.08.013.
  • Chen, H. X.; Liu, Y. Q.; Wang, W. B.; Olatunji, O. J.; Pan, G.; Ouyang, Z. Proteomic-Based Approach to the Proteins Involved in 1-Deoxynojirimycin Accumulation in Silkworm Bombyx mori (Lepidoptera: Bombycidae). J. Insect. Sci. 2018, 18, 1536–2442. DOI: 10.1093/jisesa/iey007.
  • Yatsunami, K.; Murata, K.; Kamei, T. 1-Deoxynojirimycin Content and Alfa-Glucosidase Inhibitory Activity and Heat Stability of 1-Deoxynojirimycin in Silkworm Powder. Food Nutr. Sci. 2011, 02, 87–89. DOI: 10.4236/fns.2011.22011.
  • Kim, H. S.; Kim, Y. H.; Hong, Y. S.; Paek, N. S.; Lee, H. S.; Kim, T. H.; Kim, K. W.; Lee, J. J. alpha-Glucosidase Inhibitors from Commelina Communis. Planta Med. 1999, 65, 437–439. DOI: 10.1055/s-2006-960803.
  • Kim, J. W.; Kim, S.-U.; Lee, H. S.; Kim, I.; Ahn, M. Y.; Ryu, K. S. Determination of 1-Deoxynojirimycin in Morus Alba L. leaves by Derivatization with 9-Fluorenylmethyl Chloroformate Followed by Reversed-Phase High-Performance Liquid Chromatography. J. Chromatogr. A 2003, 1002, 93–99. DOI: 10.1016/S0021-9673(03)00728-3.
  • Magalhaes, A. F.; Santos, C. C.; Magalhaes, E. G.; Nogueira, M. A. Detection of Polyhydroxyalkaloids in Lonchocarpus Extracts by GC-MS of Acetylated Derivatives. Phytochem. Anal. 2002, 13, 215–221. DOI: 10.1002/pca.645.
  • Xu, B.; Zhang, D. Y.; Liu, Z. Y.; Zhang, Y.; Liu, L.; Li, L.; Liu, C. C.; Wu, G. H. Rapid Determination of 1-Deoxynojirimycin in Morus Alba L. leaves by Direct Analysis in Real Time (DART) Mass Spectrometry. J. Pharm. Biomed. Anal. 2015, 14, 447–454. DOI: 10.1016/j.jpba.2015.06.010.
  • Liu, C.; Xiang, W.; Yu, Y.; Shi, Z. Q.; Huang, X. Z.; Xu, L. Comparative Analysis of 1-Deoxynojirimycin Contribution Degree to α-Glucosidase Inhibitory Activity and Physiological Distribution in Morus Alba L. Ind. Crops Prod. 2015, 70, 309–315. DOI: 10.1016/j.indcrop.2015.02.046.
  • Katalin, G.; András, S.; Klára, V. Microwave Extraction: A Novel Sample Preparation Method for Chromatography. J. Chromatogr. A 1986, 371, 299–306. DOI: 10.1016/S0021-9673(01)94714-4.
  • Hu, R. J.; Che, Z. M. Study on the Microwave—Assisted Extraction Method of DNJ from muberIly Ieaves. Food Sci. Technol. 2007, 32, 139–141. (in Chinese). DOI: 10.3969/j.issn.1673-6044.2008.01.016.
  • Ramya, V.; Nidoni, U.; Sharangouda, H.; Ramachandra, C. T.; Ashoka, J.; Lavanya, V. Process Optimization of Supercritical Carbon Dioxide (SC-CO2) Extraction Parameters for Extraction of Deoxynojirimycin (1-DNJ) from Mulberry (Morus Alba L.) Leaves. Jans. 2016, 8, 405–411. DOI: 10.31018/jans.v8i1.807.
  • Nuengchamnong, N.; Ingkaninan, K.; Kaewruang, W.; Wongareonwanakij, S.; Hongthongdaeng, B. Quantitative Determination of 1-Deoxynojirimycin in Mulberry Leaves Using Liquid Chromatography-Tandem Mass Spectrometry. J. Pharm. Biomed. Anal. 2007, 44, 853–858. DOI: 10.1016/j.jpba.2007.03.031.
  • Evans, S. V.; Fellows, L. E.; Shing, T. K. M.; Fleet, G. W. J. Glycosidase Inhibition by Plant Alkaloids Which Are Structural Analogues of Monosaccharides. Phytochemistry 1985, 24, 1953–1955. DOI: 10.1016/S0031-9422(00)83099-X.
  • Jiang, Y. G.; Wang, C. Y.; Jin, C.; Jia, J. Q.; Guo, X. J.; Zhang, G. Z.; Gui, Z. Z. Improved 1-Deoxynojirimycin (DNJ) Production in Mulberry Leaves Fermented by Microorganism. Braz. J. Microbiol. 2014, 45, 721–729. DOI: 10.1590/S1517-83822014000200048.
  • Matsuura, T. Progress in Membrane Science and Technology for Seawater Desalination - a Review. Desalination 2001, 134, 47–54. DOI: 10.1016/S0011-9164(01)00114-X.
  • Zhong, Y. J.; Lei, W.; Li, X. N.; Huang, L. Z.; Yi, C. Y. Enrichment and Purification of Hypoglycemic Components (1-Deoxynojirimycin)in Folium Mori. J. Zhejiang Univ. Technol. 2013, 41, 241–143. (in Chinese). http://en.cnki.com.cn/Article_en/CJFDTOTAL-ZJGD201303003.htm.
  • Jeong, J. H.; Lee, N. K.; Cho, S. H.; Jeong, D. Y.; Jeong, Y. S. Enhancement of 1-Deoxynojirimycin Content and α-Glucosidase Inhibitory Activity in Mulberry Leaf Using Various Fermenting Microorganisms Isolated from Korean Traditional Fermented Food. Biotechnol. Bioproc. E 2014, 19, 1114–1118. DOI: 10.1007/s12257-014-0277-0.
  • Kojima, M.; Tachikake, N.; Kyotani, Y.; Konno, K.; Maruo, S.; Yamamoto, M.; Ezure, Y. Effect of Dissolved Oxygen and ph on Moranoline (1-Deoxynojirimycin) Fermentation by streptomyces lavendulae. J. Fermen Bioeng. 1995, 79, 391–394. DOI: 10.1016/0922-338X(95)94004-B.
  • Ezure, Y.; Maruo, S.; Miyazaki, K.; Kawamata, M. Moranoline (1-Deoxynojirimycin) Fermentation and Its Improvement. Agric. Biol. Chem. 1985, 49, 1119–1125. DOI: 10.1271/bbb1961.49.1119.
  • Zhang, L.; Bai, Y.; Su, S.; Ouyang, Z.; Liu, L.; Pan, G.; Qian, D.; Duan, J. Metabolism, Transformation and Dynamic Changes of Alkaloids in Silkworm during Feeding Mulberry Leaves. Nat. Prod. Res. 2019, 33, 1182–1190. DOI: 10.1080/14786419.2018.
  • Lou, D. S.; Zou, F. M.; Yan, H.; Gui, Z. Z. Factors Influencing the Biosynthesis of 1- Deoxynojirimycin in Morus Alba L. Afr. J. Agr. Res. 2011, 6, 2998–3006. DOI: 10.5897/AJAR11.185.
  • Rodríguez-Sánchez, S.; Hernández-Hernández, O.; Ruiz-Matute, A. I.; Sanz, M. L. A Derivatization Procedure for the Simultaneous Analysis of Iminosugars and Other Low Molecular Weight Carbohydrates by GC–MS in Mulberry (Morus sp.). Food Chem. 2011, 126, 353–359. DOI: 10.1016/j.foodchem.2010.10.097.
  • Hu, X. Q.; Jiang, L.; Zhang, J. G.; Deng, W.; Wang, H. L.; Wei, Z. J. Quantitative Determination of 1-Deoxynojirimycin in Mulberry Leaves from 132 Varieties. Ind. Crops Prod. 2013, 49, 782–784. DOI: 10.1016/j.indcrop.2013.06.030.
  • Kimura, T.; Nakagawa, K.; Saito, Y.; Yamagishi, K.; Suzuki, M.; Yamaki, K.; Shinmoto, H.; Miyazawa, T. Simple and Rapid Determination of 1-Deoxynojirimycin in Mulberry Leaves. Biofactors 2004, 22, 341–345. DOI: 10.1002/biof.5520220167.
  • Chen, Y.; Yang, Y. K.; Wang, Z. Y. Determinationofl—Deoxynojirimycinin Mulberry Resources by HPLC. J. Chinese Mat. Med. 2010, 21, 245–246. (in Chinese). DOI: 10.3321/j.issn:1001-5302.2005.09.012.
  • Yin, H.; Shi, X. Q.; Sun, B.; Ye, J. J.; Duan, Z. A.; Zhou, X. L.; Cui, W. Z.; Wu, X. F. Accumulation of 1-Deoxynojirimycin in Silkworm, Bombyx mori L. J. Zhejiang Univ. Sci. B 2010, 11, 286–291. DOI: 10.1631/jzus.B0900344.
  • Yang, S.; Wang, B.; Xia, X.; Li, X.; Wang, R.; Sheng, L.; Li, D.; Liu, Y.; Li, Y. Simultaneous Quantification of Three Active Alkaloids from a Traditional Chinese Medicine Ramulus Mori (Sangzhi) in Rat Plasma Using Liquid Chromatography-Tandem Mass Spectrometry. J. Pharm. Biomed. Anal. 2015, 109, 177–183. DOI: 10.1016/j.jpba.2015.02.019.
  • Liang, T.; Liu, S.; Wang, F.; Gu, J.; Lu, Y.; Chen, W.; Li, C.; Zheng, Y.; Peng, G. A UPLC-MS/MS Method for Simultaneous Determination of 1-Deoxynojirimycin and N-Methyl-1-Deoxynojirimycin in Rat Plasma and Its Application in Pharmacokinetic and Absolute Bioavailability Studies. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2018, 1072, 205–210. DOI: 10.1016/j.jchromb.2017.10.055.
  • Nakagawa, K.; Kubota, H.; Kimura, T.; Yamashita, S.; Tsuzuki, T.; Oikawa, S.; Miyazawa, T. Occurrence of Orally Administered Mulberry 1-Deoxynojirimycin in Rat Plasma. J. Agric. Food Chem. 2007, 55, 8928–8933. DOI: 10.1021/jf071559m.
  • Nakagawa, K.; Ogawa, K.; Higuchi, O.; Kimura, T.; Miyazawa, T.; Hori, M. Determination of Iminosugars in Mulberry Leaves and Silkworms Using Hydrophilic Interaction Chromatography-Tandem Mass Spectrometry. Anal. Biochem. 2010, 404, 217–222. DOI: 10.1016/j.ab.2010.05.007.
  • Kim, J. Y.; Kwon, H. J.; Jung, J. Y.; Kwon, H. Y.; Baek, J. G.; Kim, Y. S.; Kwon, O. Comparison of Absorption of 1-Deoxynojirimycin from Mulberry Water Extract in Rats. J. Agric. Food Chem. 2010, 58, 6666–6671. DOI: 10.1021/jf100322y.
  • Yoshihashi, T.; Do, H. T.; Tungtrakul, P.; Boonbumrung, S.; Yamaki, K. Simple, Selective, and Rapid Quantification of 1-Deoxynojirimycin in Mulberry Leaf Products by High-Performance Anion-Exchange Chromatography with Pulsed Amperometric Detection. J. Food Sci. 2010, 75, C246–50. DOI: 10.1111/j.1750-3841.2010.01528.x.
  • Yang, H. X. The Studies on the Extraction, Purification and Content Determination of DNJ from Mulberry Leaves; Zhejiang University: Hangzhou, 2003.
  • Barker, S. A. Matrix Solid Phase Dispersion (MSPD). J. Biochem. Bioph. Meth. 2007, 70, 151–162. DOI: 10.1016/j.jbbm.2006.06.005.
  • Schmidt, C. M.; Smolke, C. D. RNA Switches for Synthetic Biology. Cold Spring Harb. Perspect. Biol. 2019, 11, pii: a032532. DOI: 10.1101/cshperspect.a032532.
  • Stalikas, C. D. Extraction, Separation, and Detection Methods for Phenolic Acids and Flavonoids. J. Sep. Sci. 2007, 30, 3268–3295. DOI: 10.1002/jssc.200700261.
  • Hu, K. f.; Li, Y.; Du, Y.; Su, B.; Lu, A. Of 1-Deoxynojirimycin Component Correlation between Medicinal Parasitic Loranthus from Loranthaceae and Their Mulberry Host Trees. J. Med. Plant Res. 2011, 5, 4326–4331. http://www.academicjournals.org/JMPR.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.