PL241002B1 - Method of preparing 2'-O-β-D-(4"-O-methylglucopyranosyl)-flavone - Google Patents
Method of preparing 2'-O-β-D-(4"-O-methylglucopyranosyl)-flavone Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 241000030456 Isaria farinosa Species 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- YEHDMSUNJUONMW-UHFFFAOYSA-N 2'-methoxyflavone Chemical compound COC1=CC=CC=C1C1=CC(=O)C2=CC=CC=C2O1 YEHDMSUNJUONMW-UHFFFAOYSA-N 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 7
- 230000009466 transformation Effects 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- 239000003480 eluent Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000003595 spectral effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 abstract description 3
- 108090000790 Enzymes Proteins 0.000 abstract description 3
- 238000010520 demethylation reaction Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- 244000005700 microbiome Species 0.000 abstract description 2
- 229930003935 flavonoid Natural products 0.000 description 5
- 150000002215 flavonoids Chemical class 0.000 description 5
- 235000017173 flavonoids Nutrition 0.000 description 5
- 229930003944 flavone Natural products 0.000 description 4
- 150000002213 flavones Chemical class 0.000 description 4
- 235000011949 flavones Nutrition 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 2
- 102000000340 Glucosyltransferases Human genes 0.000 description 2
- 108010055629 Glucosyltransferases Proteins 0.000 description 2
- 101100369992 Homo sapiens TNFSF10 gene Proteins 0.000 description 2
- 244000072254 Primula veris Species 0.000 description 2
- 102000046283 TNF-Related Apoptosis-Inducing Ligand Human genes 0.000 description 2
- 108700012411 TNFSF10 Proteins 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BWAGQNPYTNMEJP-UHFFFAOYSA-N 2-phenylchromene-4-thione Chemical class O1C2=CC=CC=C2C(=S)C=C1C1=CC=CC=C1 BWAGQNPYTNMEJP-UHFFFAOYSA-N 0.000 description 1
- ZAIANDVQAMEDFL-UHFFFAOYSA-N 3-methoxy-2-phenylchromen-4-one Chemical class O1C2=CC=CC=C2C(=O)C(OC)=C1C1=CC=CC=C1 ZAIANDVQAMEDFL-UHFFFAOYSA-N 0.000 description 1
- 102000051366 Glycosyltransferases Human genes 0.000 description 1
- 108700023372 Glycosyltransferases Proteins 0.000 description 1
- 235000002343 Primula veris Nutrition 0.000 description 1
- 235000002315 Rosa hybrid cultivar Nutrition 0.000 description 1
- 101100434907 Rosa hybrid cultivar RhGT1 gene Proteins 0.000 description 1
- 244000037691 Rosa hybrida Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940046836 anti-estrogen Drugs 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000967 entomopathogenic effect Effects 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 229940066493 expectorants Drugs 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 108700014210 glycosyltransferase activity proteins Proteins 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Zgłoszenie dotyczy sposobu wytwarzania 2'-O-ß-D-(4"-O-metyloglukopiranozylo)-flawonu. W wyniku działania układu enzymatycznego zawartego w komórkach szczepu Isaria farinosa KCh KW1.1, następuje O-demetylacja i 4"-O-metyloglikozylacja. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem, przez ekstrakcję rozpuszczalnikiem organicznym niemieszającym się z wodą (octan etylu).The application concerns the method of producing 2'-O-ß-D-(4"-O-methylglucopyranosyl)-flavone. As a result of the activity of the enzyme system contained in the cells of the Isaria farinosa KCh KW1.1 strain, O-demethylation and 4"-O- methylglycosylation. The product thus obtained is separated from the aqueous culture of the microorganism by a known method by extraction with a water-immiscible organic solvent (ethyl acetate).
Description
PL 241 002 B1PL 241 002 B1
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest sposób wytwarzania 2’-O-e-D-(4”-O-metyloglukopiranozylo)-flawonu.The present invention relates to a process for the preparation of 2′-O-e-D- (4 "-O-methylglucopyranosyl) -flavone.
Metoda, według wynalazku może znaleźć zastosowanie w przemyśle farmaceutycznym do wytwarzania składników preparatów poprawiających funkcjonowanie przewodu pokarmowego.The method according to the invention may find application in the pharmaceutical industry for the production of ingredients of preparations improving the functioning of the gastrointestinal tract.
Flawony są syntezowane przez rośliny i stanowią składnik naszej diety o wysokim potencjale antyoksydacyjnym oraz zdolności do modulowania różnych układów enzymatycznych związanych z wieloma chorobami (Mughal E.U., Ayaz M., Hussain Z., Hasan A., Sadiq A., Riaz M., Malik A., Hussain S., Choudhary M.l. 2006. Synthesis and antibacterial activity of substituted flavones, 4-thioflavones and 4-iminoflavones. Bioorg. Med. Chem. 14: 4704-4711). Zarówno naturalne, półsyntetyczne i syntetyczne flawony zostały scharakteryzowane pod kątem szeregu działań terapeutycznych, takich jak działania przeciwzapalne, przeciwestrogenowe, przeciwdrobnoustrojowe (Cushnie T.P.T., Lamb A.J. 2005. Antimicrobial activity of flavonoids. Int. J. Antimicrol. Agents 26: 343-35), przeciwalergiczne, przeciwutleniające, przeciwnowotworowe czy też cytotoksyczne (Havsteen B. 1983. Flavonoids, a class of natural products of high pharmacological potency. Biochem. Pharmacol. 32: 1141-1148; Aregawi M., Williams R., Dye C., Cibulskis R., Otten M. 2008. World Malaria 2008, World Health Organization (WHO): Geneva). 2’-metoksyflawon był wyizolowany z kultury tkankowej rośliny leczniczej Primula veris, z której wykonuje się preparaty wykrztuśne (Jaromir Budzianowski, Maria Morozowska, Maria Wesołowska. Lipophilic flavones of Primula veris L. from field cultivation and in vitro cultures. Phytochemistry 66 (2005) 1033-1039).Flavones are synthesized by plants and are part of our diet with high antioxidant potential and the ability to modulate various enzyme systems associated with many diseases (Mughal E.U., Ayaz M., Hussain Z., Hasan A., Sadiq A., Riaz M., Malik A., Hussain S., Choudhary M.I. 2006. Synthesis and antibacterial activity of substituted flavones, 4-thioflavones and 4-iminoflavones. Bioorg. Med. Chem. 14: 4704-4711). Both natural, semi-synthetic and synthetic flavones have been characterized for a number of therapeutic activities, such as anti-inflammatory, anti-estrogen, and antimicrobial activities (Cushnie T.P.T., Lamb A.J. 2005. Antimicrobial activity of flavonoids. Int. J. Antimicrol. Agents 26: 343-35), antiallergic, antioxidant, antitumor or cytotoxic (Havsteen B. 1983. Flavonoids, a class of natural products of high pharmacological potency. Biochem. Pharmacol. 32: 1141-1148; Aregawi M., Williams R., Dye C., Cibulskis R ., Otten M. 2008. World Malaria 2008, World Health Organization (WHO): Geneva). 2'-methoxyflavone was isolated from the tissue culture of the medicinal plant Primula veris, from which expectorants are made (Jaromir Budzianowski, Maria Morozowska, Maria Wesołowska. Lipophilic flavones of Primula veris L. from field cultivation and in vitro cultures. Phytochemistry 66 (2005) 1033-1039).
2’-metoksyflawon jest aktywnym czynnikiem wywołującym apoptozę indukowaną przez TRAIL w ludzkich białaczkowych komórkach MOLT-4 (Benjawan Wudtiwai, Bungorn Sripanidkulchai, Prachya Kongtawelert, Ratana Banjerdpongchai. Methoxyflavone derivatives modulate the effect of TRAIL-induced apoptosis in human leukemic cell lines. Journal of Hematology & Oncology 2011, 4:52). Obecność jednostki cukrowej ma wpływ na stabilność i rozpuszczalność flawonoidów, a często także wpływa na ich biodostępność i bioaktywność (Wang X. Structure, mechanism and engineering of plant natural product glycosyltransferases. FEBS Lett. 2009; 583(20):3303-9; Wang L, Han W, Xie C, Hou J, Fang Q, Gu J, et al. Comparing the acceptor promiscuity of a Rosa hybrida glucosyltransferase RhGT1 and an engineered microbial glucosyltransferase OleDPSA toward a small flavonoid library. Carbohydr Res. 2013; 368:73-7; Pandey RP, Gurung RB, Parajuli P, Koirala N, Tuoi LT, Sohng JK. Assessing acceptor substrate promiscuity of YjiC-mediated glycosylation toward flavonoids. Carbohydr Res. 2014; 393:26-31).2'-methoxyflavone is an active agent of TRAIL-induced apoptosis in human MOLT-4 leukemic cells (Benjawan Wudtiwai, Bungorn Sripanidkulchai, Prachya Kongtawelert, Ratana Banjerdpongchai. Methoxyflavone derivatives modulate the effect of TRAIL-induced lines in human leukoptosis. Hematology & Oncology 2011, 4:52). The presence of a sugar unit affects the stability and solubility of flavonoids, and often also affects their bioavailability and bioactivity (Wang X. Structure, mechanism and engineering of plant natural product glycosyltransferases. FEBS Lett. 2009; 583 (20): 3303-9; Wang L, Han W, Xie C, Hou J, Fang Q, Gu J, et al. Comparing the acceptor promiscuity of a Rosa hybrida glucosyltransferase RhGT1 and an engineered microbial glucosyltransferase OleDPSA toward a small flavonoid library. Carbohydr Res. 2013; 368: 73 -7; Pandey RP, Gurung RB, Parajuli P, Koirala N, Tuoi LT, Sohng JK. Assessing acceptor substrate promiscuity of YjiC-mediated glycosylation toward flavonoids. Carbohydr Res. 2014; 393: 26-31).
Szczep Isaria farinosa KCh KW1.1 był wcześniej ujawniony w literaturze (Kozłowska E., Urbaniak M., Grzeszczuk J., Hoc N., Sycz J., Dymarska M., Kostrzewa-Susłow E., Stępień Ł., Pląskowska E., Janeczko T. (2018) Biotransformation of steroids by entomopathogenic strains of Isaria farinosa. Microbial Cell Factories 17:71. https://doi.org/10.1186/s12934-018-0920-0).The Isaria farinosa strain KCh KW1.1 was previously disclosed in the literature (Kozłowska E., Urbaniak M., Grzeszczuk J., Hoc N., Sycz J., Dymarska M., Kostrzewa-Susłow E., Stępień Ł., Pląskowska E. , Janeczko T. (2018) Biotransformation of steroids by entomopathogenic strains of Isaria farinosa. Microbial Cell Factories 17:71. Https://doi.org/10.1186/s12934-018-0920-0).
Istota wynalazku polega na tym, że do podłoża odpowiedniego dla grzybów strzępkowych wprowadza się Isaria farinosa KCh KW1.1. Po upływie co najmniej 48 godzin do hodowli wprowadza się substrat, którym jest 2’-metoksyflawon, rozpuszczony w rozpuszczalniku organicznym mieszającym się z wodą. Transformację prowadzi się w temperaturze od 20 do 30 stopni Celsjusza, przy ciągłym wstrząsaniu, co najmniej 1 dobę. Kolejno produkt ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą i oczyszcza chromatograficznie.The essence of the invention consists in introducing Isaria farinosa KCh KW1.1 into a substrate suitable for filamentous fungi. After at least 48 hours, the substrate is introduced into the culture, which is 2'-methoxy flavone dissolved in a water-miscible organic solvent. The transformation is carried out at a temperature of 20 to 30 degrees Celsius, with continuous shaking, for at least 1 day. Subsequently, the product is extracted with a water-immiscible organic solvent and purified by chromatography.
W wyniku regioselektywnej O-demetylacji i 4”-O-metyloglikozylacji otrzymuje się 2’-O -e-D-(4”- O-metyloglukopiranozylo)-flawon, a reakcję prowadzi się w wodnej kulturze szczepu Isaria farinosa KCh KW1.1.Regioselective O-demethylation and 4 "-O-methylglycosylation give 2'-O -e-D- (4" - O-methylglucopyranosyl) -flavone, and the reaction is carried out in an aqueous culture of the Isaria farinosa KCh KW1.1 strain.
Korzystnie jest, gdy stosunek masy dodawanego substratu do objętości hodowli wynosi 0,2 g : 1 L.Preferably, the ratio of the mass of the added substrate to the culture volume is 0.2 g: 1 L.
Korzystnie także jest, gdy proces prowadzi się w temperaturze 25 stopni Celsjusza.It is also preferred that the process is carried out at a temperature of 25 degrees Celsius.
Dodatkowo, korzystnie jest, gdy transformację prowadzi się przez 7 dni.Additionally, it is preferred that the transformation is carried out for 7 days.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w komórkach szczepu Isaria farinosa KCh KW1.1, następuje regioselektywna O-demetylacja i 4”-O -metyloglikozylacja substratu. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem, przez ekstrakcję rozpuszczalnikiem organicznym niemieszającym się z wodą (octan etylu). Zasadniczą zaletą wynalazku jest otrzymanie 2’-O-e-D-(4”- O -metyloglukopiranozylo)-flawonu, z wydajnością izolowaną na poziomie 10% (konwersją według HPLC <40%), w temperaturze pokojowej i przy pH naturalnym dla szczepu.By following the invention, regioselective O-demethylation and 4 "-O-methylglycosylation of the substrate occur as a result of the enzyme system contained in the cells of the Isaria farinosa KCh KW1.1 strain. The product obtained in this way is separated from the aqueous culture of the microorganism by a known method by extraction with a water-immiscible organic solvent (ethyl acetate). The main advantage of the invention is to obtain 2'-O-e-D- (4 "- O-methylglucopyranosyl) -flavone with an isolated yield of 10% (conversion according to HPLC <40%), at room temperature and pH natural for the strain.
Claims (5)
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| PL429216A PL241002B1 (en) | 2019-03-11 | 2019-03-11 | Method of preparing 2'-O-β-D-(4"-O-methylglucopyranosyl)-flavone |
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| PL241002B1 true PL241002B1 (en) | 2022-07-11 |
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