PL237334B1 - 7-O-β-D-4'''-O-methyl-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone and 3'-O-β-D-4'''-O-methyl-glucopyranozyl-5,7-dihydroxy-4'-methoxyflavanone and method for simultaneously obtaining of 7-O-β-D-4'''-O-methyl-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone and 3'-O-β-D-4'''-O-methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone - Google Patents
7-O-β-D-4'''-O-methyl-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone and 3'-O-β-D-4'''-O-methyl-glucopyranozyl-5,7-dihydroxy-4'-methoxyflavanone and method for simultaneously obtaining of 7-O-β-D-4'''-O-methyl-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone and 3'-O-β-D-4'''-O-methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone Download PDFInfo
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- PL237334B1 PL237334B1 PL422147A PL42214717A PL237334B1 PL 237334 B1 PL237334 B1 PL 237334B1 PL 422147 A PL422147 A PL 422147A PL 42214717 A PL42214717 A PL 42214717A PL 237334 B1 PL237334 B1 PL 237334B1
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- dihydroxy
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- glucopyranosyl
- methoxyflavanone
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- 238000000034 method Methods 0.000 title claims abstract description 14
- 241000751139 Beauveria bassiana Species 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 230000009466 transformation Effects 0.000 claims abstract description 9
- 239000000758 substrate Substances 0.000 claims abstract description 8
- 230000000813 microbial effect Effects 0.000 claims abstract description 4
- 241000233866 Fungi Species 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- AIONOLUJZLIMTK-AWEZNQCLSA-N hesperetin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-AWEZNQCLSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 0 COc1ccc(C(CC2=O)Oc3c2c(O)cc(*)c3)cc1N Chemical compound COc1ccc(C(CC2=O)Oc3c2c(O)cc(*)c3)cc1N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 238000006206 glycosylation reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- LPEPZZAVFJPLNZ-SFHVURJKSA-N 8-Prenylnaringenin Natural products C1([C@@H]2CC(=O)C=3C(O)=CC(O)=C(C=3O2)CC=C(C)C)=CC=C(O)C=C1 LPEPZZAVFJPLNZ-SFHVURJKSA-N 0.000 description 1
- DFFCTMORCDDRBM-USGNCJJDSA-N CO[C@H](C(CO)O[C@H](C1O)Oc2cc(OC(CC3=O)c(cc4N)ccc4OC)c3c(O)c2)C1O Chemical compound CO[C@H](C(CO)O[C@H](C1O)Oc2cc(OC(CC3=O)c(cc4N)ccc4OC)c3c(O)c2)C1O DFFCTMORCDDRBM-USGNCJJDSA-N 0.000 description 1
- 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 description 1
- YKGCBLWILMDSAV-GOSISDBHSA-N Isoxanthohumol Natural products O(C)c1c2C(=O)C[C@H](c3ccc(O)cc3)Oc2c(C/C=C(\C)/C)c(O)c1 YKGCBLWILMDSAV-GOSISDBHSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- -1 flavonoid compounds Chemical class 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- YKGCBLWILMDSAV-SFHVURJKSA-N isoxanthohumol Chemical compound C1([C@H]2OC=3C(CC=C(C)C)=C(O)C=C(C=3C(=O)C2)OC)=CC=C(O)C=C1 YKGCBLWILMDSAV-SFHVURJKSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002417 nutraceutical Substances 0.000 description 1
- 235000021436 nutraceutical agent Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- YHWNASRGLKJRJJ-UHFFFAOYSA-N sophoraflavanone B Natural products C1C(=O)C2=C(O)C(CC=C(C)C)=C(O)C=C2OC1C1=CC=C(O)C=C1 YHWNASRGLKJRJJ-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Zgłoszenie dotyczy sposobu otrzymywania mieszaniny 7-O-ß-D-4'-O- metylo-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu, o wzorze 2 i 3'-O-ß-D-4"'-O-metylo-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu, o wzorze 3, na drodze transformacji mikrobiologicznej, przy użyciu systemu enzymatycznego grzybów strzępkowych z gatunku Beauveria bassiana. Jako substrat stosuje się 3',5,7-trihydroksy-4'-metoksyflawanon. Przedmiotem zgłoszenia jest także sama mieszanina związku o wzorze 2 i o wzorze 3, otrzymana powyższym sposobem."The application relates to a method of obtaining a mixture of 7-O-ß-D-4'-O-methyl-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone of formula 2 and 3'-O-ß-D-4"' -O-methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone, of the formula 3, by microbial transformation using the enzymatic system of the filamentous fungus Beauveria bassiana.3',5,7-trihydroxy is used as a substrate -4'-methoxyflavanone The subject of the application is also the same mixture of the compound of formula 2 and formula 3 obtained by the above method."
Description
Przedmiotem wynalazku jest mieszanina 7-Ο-β-D-4'- O-metylo-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu, o wzorze 2 i 3'-Ο-β-D -4'-O-metylo-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu, o wzorze 3 przedstawionym na rysunku oraz sposób jednoczesnego otrzymywania 7-Ο-β-D-4'-O-metylo-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu i 3'-Ο-β-D -4'-O-metylo-glukopiranozylo-5,7-dihydroksy-4'-metoksy-flawanonu.The subject of the invention is a mixture of 7-Ο-β-D-4'-O-methyl-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone, of the formula 2 and 3'-Ο-β-D -4'-O -methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxy flavanone of formula 3 shown in the figure and the method of simultaneous preparation of 7-Ο-β-D-4'-O-methyl-glucopyranosyl-3 ', 5-dihydroxy- 4'-methoxy flavanone and 3'-Ο-β-D -4'-O-methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxy-flavanone.
Budowa chemiczna otrzymanych składników mieszaniny wskazuje na ich aktywność biologiczną oraz ich potencjalne zastosowanie w przemyśle spożywczym i farmaceutycznym.The chemical structure of the obtained components of the mixture indicates their biological activity and their potential use in the food and pharmaceutical industries.
W dostępnej literaturze nie znaleziono doniesień o przedmiotowych związkach ani o sposobach ich otrzymywania.In the available literature, no reports of the compounds in question or the methods of their preparation were found.
Glikozylacja flawonoidów zwiększa ich hydrofilowość, co można wykorzystać podczas produkcji rozpuszczalnych w wodzie nutraceutyków. Związek według wynalazku jest potencjalnym materiałem wyjściowym dla dalszych strukturalnych modyfikacji, które mogą okazać się użyteczne w produkcji aktywniejszych związków.The glycosylation of flavonoids increases their hydrophilicity, which can be used in the production of water-soluble nutraceuticals. The compound of the invention is a potential starting material for further structural modifications that may prove useful in the production of more active compounds.
Szczep Beauveria bassiana AM 278 zdeponowany jest w kolekcji mikroorganizmów Katedry Chemii Uniwersytetu Przyrodniczego we Wrocławiu (ul. C.K. Norwida 25, 50-375 Wrocław).The Beauveria bassiana AM 278 strain is deposited in the collection of microorganisms of the Department of Chemistry, University of Life Sciences in Wrocław (C.K. Norwida 25, 50-375 Wrocław).
Znane są procesy biotransformacji przy udziale grzybów strzępkowych z gatunku Beauveria bassiana . Opisano m. in. jego zdolność do glikozylacji związków flawonoidowych. W wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Beauveria bassiana otrzymano szereg związków przy udziale tego gatunku, takich jak: z opisu PL 222200 - 4'-O-β-D -4''-metoksy-glukopiranozylo-3-[1'-hydroksyizopropylo]-4,2'-dihydroksy-6'-metoksy-3'-prenylo-a,3-dihydrochalkonu, z opisu PL 213614 - 7-O-3-D-4'-metoksyglukopiranozyd 8-prenylonaringeniny, z PL 226314 - 4'-O-3-D-4'-O-metylo-glukopiranozylo-1,2,a,3-tetrahydroksantohumolu K, z PL 210638 znane jest otrzymywanie 7-O-3-D-4'-metoksyglukopiranozyd izoksantohumolu, z PL 222788 - otrzymywanie 4'-O-3-D-4'-metoksy-glukopiranozylo-4,2'-dihydroksy-6'-metoksy-3'-prenylo-a,3-dihydrochalkonu, natomiast opis patentowy PL 215796 ujawnia otrzymywanie (Z)-6-O-3-D-4'-O-metylo-glukopiranozylo-4'-hydroksy-4-metoksy-7-prenyloauronu.Biotransformation processes involving the filamentous fungi Beauveria bassiana are known. It has been described, inter alia, its ability to glycosylate flavonoid compounds. As a result of the enzyme system contained in living cells of the Beauveria bassiana culture, a number of compounds were obtained with the participation of this species, such as: from the description PL 222200 - 4'-O-β-D -4 '' - methoxy-glucopyranosyl-3- [1 ' -hydroxyisopropyl] -4,2'-dihydroxy-6'-methoxy-3'-prenyl-a, 3-dihydroochalcone, from PL 213614 - 8-prenylnaringenin 7-O-3-D-4'-methoxyglucopyranoside, from PL 226314 - 4'-O-3-D-4'-O-methyl-glucopyranosyl-1,2, a, 3-tetrahydroxanthohumol K, from PL 210638 it is known to prepare isoxanthohumol 7-O-3-D-4'-methoxyglucopyranoside , from PL 222788 - preparation of 4'-O-3-D-4'-methoxy-glucopyranosyl-4,2'-dihydroxy-6'-methoxy-3'-prenyl-a, 3-dihydroochalcone, while the patent description PL 215796 discloses the preparation of (Z) -6-O-3-D-4'-O-methyl-glucopyranosyl-4'-hydroxy-4-methoxy-7-prenylaaurone.
Istotą wynalazku jest mieszanina 7-O-β-D -4'-O-metylo-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu i 3'-O-β-D -4'-O-metylo-glukopiranozylo-5,7-dihydroksy-4’-metoksyflawanonu.The essence of the invention is a mixture of 7-O-β-D -4'-O-methyl-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxyflavanone and 3'-O-β-D -4'-O-methyl-glucopyranosyl -5,7-dihydroxy-4'-methoxyflavanone.
Istotą wynalazku jest także sposób otrzymywania tych związków, polegający na tym, że substrat, którym jest 3',5,7-trihydroksy-4'-metoksyflawanon, poddaje się transformacji mikrobiologicznej, w wyniku czego otrzymuje się 7-O-β-D-4'-O-metylo-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanon i 3'-O-β-D -4'-O-metylo-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanon. Grzyby strzępkowe z gatunku Beauveria bassiana namnaża się w płynnym podłożu mikrobiologicznym, przy ciągłym mieszaniu reagentów, w temperaturze 12-40°C. Następnie do narośniętej hodowli dodaje się substrat i dalej prowadzi się proces do całkowitego zużycia substratu. Po zakończeniu transformacji roztwór transformacyjny ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą, oddziela frakcję organiczną, osusza bezwodnym siarczanem magnezu, odparowuje rozpuszczalnik i tak otrzymany surowy produkt oczyszcza się za pomocą technik chromatograficznych.The essence of the invention is also the method of obtaining these compounds, consisting in the fact that the substrate, which is 3 ', 5,7-trihydroxy-4'-methoxyflavanone, is subjected to microbiological transformation, as a result of which 7-O-β-D- is obtained. 4'-O-methyl-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone and 3'-O-β-D -4'-O-methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxy flavanone. Filamentous fungi of the species Beauveria bassiana are multiplied in a liquid microbial medium under constant stirring of the reagents at a temperature of 12-40 ° C. Subsequently, a substrate is added to the grown culture and the process is continued until the substrate is completely consumed. After completion of the transformation, the transformation solution was extracted with a water-immiscible organic solvent, the organic fraction was separated, dried over anhydrous magnesium sulfate, the solvent was evaporated and the crude product thus obtained was purified by chromatographic techniques.
Korzystnie jest, gdy grzybem z gatunku Beauveria bassiana jest szczep Beauveria bassiana AM 278.Preferably, the fungus of the species Beauveria bassiana is Beauveria bassiana AM 278.
Korzystnie jest, gdy reakcję prowadzi się w temperaturze 26°C.It is advantageous when the reaction is carried out at a temperature of 26 ° C.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Beauveria bassiana następuje reakcja glikozylacji substratu.By following the invention, the substrate glycosylation reaction takes place as a result of the enzyme system contained in living cells of the Beauveria bassiana culture.
Zasadniczą zaletą wynalazku jest otrzymanie, w łagodnych warunkach 7-O-β-D -4'-O-metylo-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu i 3'-O-β-D-4'-O-metylo-gIukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu, jako głównych produktów reakcji w kulturze Beauveria bassiana. Wydajność reakcji osiąga poziom ponad 30% dla obu związków.The main advantage of the invention is the preparation of 7-O-β-D -4'-O-methyl-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone and 3'-O-β-D-4'- under mild conditions. O-methyl-gIucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone as the main reaction products in Beauveria bassiana culture. The reaction yield is over 30% for both compounds.
Wynalazek jest bliżej objaśniony w przykładzie wykonania.The invention is explained in more detail in an exemplary embodiment.
P r z y k ł a d 1. Do kolby o pojemności 300 cm3, w której znajduje się 100 cm3 sterylnej pożywki zawierającej 3 g glukozy i 1 g aminobaku na 1 dm3 wody destylowanej, wprowadza się grzyby strzępkowe Beauveria bassiana AM278. Po 6 dniach wzrostu drobnoustrojów w temperaturze 26°C i przy ciągłym wstrząsaniu, dodaje się 15 mg 3',5,7-trihydroksy-4'-metoksyflawanonu, o wzorze 1, rozpuszczonego w 1,5 cm3 dimetylosulfotlenku. Transformację prowadzi się przy ciągłym wstrząsaniu przez 10EXAMPLE 1 To a flask of 300 cm 3, which is 100 cm 3 of sterile medium containing 3 g of glucose and 1 g aminobaku per 1 dm 3 of distilled water is introduced into filamentous fungi, Beauveria bassiana AM278. After 6 days, the growth of microorganisms at 26 ° C with continuous shaking, is added 15 mg of 3 ', 5,7-trihydroxy-4'-metoksyflawanonu of formula 1, dissolved in 1.5 cm 3 of dimethyl sulfoxide. The transformation is carried out under continuous shaking for 10
PL 237 334 B1 dób. Po tym czasie hodowlę zakwasza się 1-molowym kwasem chlorowodorowym do pH 4,5. Następnie, uzyskany roztwór transformacyjny ekstrahuje się trzykrotnie octanem etylu, osusza bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Uzyskuje się 25 mg surowego ekstraktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaninę chloroform : metanol w stosunku objętościowym 9:1. Po oczyszczeniu otrzymuje się 16,75 mg mieszaniny 7-Ο-β-D -4'-O-metylo-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu, o wzorze 2 i 3’-Ο-β-D- 4'-O-metylo-glukopiranozylo-5,7-dihydroksy-4’-metoksyflawanonu, o wzorze 3, z wydajnością 37,7% dla 7-Ο-β-D -4'-O-metylo-glukopiranozylo-3’,5-dihydroksy-4’-metoksyflawanonu i 32,8% dla 3’-Ο-β-D -4'-O-metylo-glukopiranozylo-5,7-dihydroksy-4’-metoksyflawanonu.Day. After this time, the culture is acidified with 1 M hydrochloric acid to a pH of 4.5. Then, the resulting transformation solution was extracted three times with ethyl acetate, dried with anhydrous magnesium sulfate, and the solvent was evaporated. This gives 25 mg of crude extract which is purified by chromatography using 9: 1 by volume chloroform: methanol as eluent. After purification, 16.75 mg of a mixture of 7-Ο-β-D -4'-O-methyl-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone, of the formula 2 and 3'-Ο-β-D are obtained. - 4'-O-methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxy flavanone, of formula 3, with a yield of 37.7% for 7-Ο-β-D -4'-O-methyl-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone and 32.8% for 3'-Ο-β-D -4'-O-methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxy flavanone.
Uzyskane produkty charakteryzują się następującymi danymi spektralnymi:The obtained products are characterized by the following spectral data:
7-Ο-β-D -4'-O-metylo-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanon:7-Ο-β-D -4'-O-methyl-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone:
1H NMR (600 MHz, DMSO-d6) δ (ppm): 2,75 (1H, dd, J=3,2; 17,1 Hz, H-3aeq), 2,77 (1H, dd, J=3,2; 17,1 Hz, H-3beq), 3,03 (1H, t, J=9,3 Hz, H-4), 3,19-3,23 (1H, m, H-2), 3,36-3,42 (2H, m, H-3, H-5), 3,28 (1H, dd, J=12,6; 17,1 Hz, H-3ax), 3,44 (3H, s, 4-OCHs), 3,47 (1H, m, Ha-6), 3,57-3,62 (1H, m, Hb6), 3,77 (3H, s, 4'OCHs) 5,00 (1H, d, J=7,8 Hz, H-1), 5,48 (1H, dd, J=3,2; 12,3 Hz, H-2a), 5,49 (1H, dd, J=3,2; 12,3 Hz, H-2b), 6,13 (1H, m, H-6), 6,15 (1H, m, H-8), 6,88 (1H, m, H-61), 6,95 (2H, m, H-2’, H-5'), 9,12 (1H, s, 3'-OH), 12,04 (1H, s, 5-OH), 13C NMR (150 MHz, DMSO-d6) δ (ppm): 42,15 (C-3), 55,69 (4'OCHs), 60,12 (C-6), 59,65 (4OCHsa), 59,68 (4OCH3b), 73,19 (C-2), 76,00 (C-3a), 76,02 (C-3b), 75,55 (C-5), 78,50 (C-2a), 78,54 (C-2b), 78,79 (C-4a), 78,96 (C-4b), 95,85 (C-8), 96,45 (C-6), 99,10 (C-1), 103,30 (C-10), 111,98 (C-5'), 114,17 (C-2'), 117,85 (C-6'), 129,62 (C-1'), 146,17 (C-3'), 147,99 (C-4'), 162,83 (C-9), 162,91 (C-5a), 162,94 (C-5b), 165,12 (C-7a), 165,20 (C-7b), 197,10 (C-4). 1 H NMR (600 MHz, DMSO-d6) δ (ppm): 2.75 (1H, dd, J = 3.2; 17.1 Hz, H-3aeq), 2.77 (1H, dd, J = 3.2; 17.1 Hz, H-3beq), 3.03 (1H, t, J = 9.3 Hz, H-4), 3.19-3.23 (1H, m, H-2) , 3.36-3.42 (2H, m, H-3, H-5), 3.28 (1H, dd, J = 12.6; 17.1 Hz, H-3ax), 3.44 ( 3H, s, 4-OCHs), 3.47 (1H, m, Ha-6), 3.57-3.62 (1H, m, Hb6), 3.77 (3H, s, 4'OCHs) 5 .00 (1H, d, J = 7.8Hz, H-1), 5.48 (1H, dd, J = 3.2; 12.3Hz, H-2a), 5.49 (1H, dd , J = 3.2; 12.3 Hz, H-2b), 6.13 (1H, m, H-6), 6.15 (1H, m, H-8), 6.88 (1H, m , H-6 1 ), 6.95 (2H, m, H-2 ', H-5'), 9.12 (1H, s, 3'-OH), 12.04 (1H, s, 5- OH), 13 C NMR (150 MHz, DMSO-d6) δ (ppm): 42.15 (C-3), 55.69 (4'OCHs), 60.12 (C-6), 59.65 ( 4OCHsa), 59.68 (4OCH3b), 73.19 (C-2), 76.00 (C-3a), 76.02 (C-3b), 75.55 (C-5), 78.50 ( C-2a), 78.54 (C-2b), 78.79 (C-4a), 78.96 (C-4b), 95.85 (C-8), 96.45 (C-6), 99.10 (C-1), 103.30 (C-10), 111.98 (C-5 '), 114.17 (C-2'), 117.85 (C-6 '), 129, 62 (C-1 '), 146.17 (C-3'), 147.99 (C-4 '), 162.83 (C-9), 162.91 (C-5a), 162.94 ( C-5b), 165.12 (C-7a), 165.20 (C-7b), 197.10 ( C-4).
3'-O-3-D-4'''-O-metylo-glukopiranozylo-5,7-dihydroksy-4’-metoksyflawanon:3'-O-3-D-4 '' - O-methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxy flavanone:
1H NMR (600 MHz, DMSO-d6) δ (ppm): 2,71 (1H, dd, J=3,2; 17,1 Hz, H-3eq), 3,01 (1H, t, J-9,3 Hz, H-4), 3,19-3,23 (1H, m, H-2), 3,36-3,42 (2H, m, H-3, H-5), 3,28 (1H, dd, J=12,6; 17,1 Hz, H-3ax), 3,44 (3H, s, 4OCH3), 3,47 (1H, m, Ha-6), 3,57-3,62 (1H, m, Hb-6), 3,77 (3H, s, 4'OCH3), 4,97 (1H, d, J=8,0 Hz, H-1), 5,46 (1H, dd, J=3,2; 12,3 Hz, H-2), 5,88 (1H, d, J=2,1 Hz, H-6), 5,90 (1H, d, J=2,1 Hz, H-8), 7,00 (1H, d, J=8,3 Hz, H-5'), 7,07 (1H, dd, J=2,1; 8,3 Hz, H-6'), 7,21 (1H, d, J=2,1 Hz, H-2'), 12,14 (1H, s, 5-OH), 13C NMR (150 MHz, DMSO-d6) δ (ppm): 41,90 (C-3), 55,71 (4'OCH3), 59,79 (C-4-OCH3), 60,12 (C-6), 73,35 (C-2), 76,64 (C-3), 75,55 (C-5), 78,39 (C-2), 79,19 (C-4), 95,07 (C-8), 95,43 (C-6), 99,20 (C-1 a), 99,27 (C-1b), 101,77 (C-10), 112,20 (C-5'), 113,63 (C-2'), 120,57 (C-6'), 130,82 (C-1'a), 130,88 (C-1'a), 146,48 (C-3'), 149,11 (C- 4'), 162,62 (C-9a), 162,67 (C-9b), 163,48 (C-5), 166,77 (C-7), 196,26 (C-4). 1 H NMR (600 MHz, DMSO-d6) δ (ppm): 2.71 (1H, dd, J = 3.2; 17.1 Hz, H-3eq), 3.01 (1H, t, J- 9.3 Hz, H-4), 3.19-3.23 (1H, m, H-2), 3.36-3.42 (2H, m, H-3, H-5), 3, 28 (1H, dd, J = 12.6; 17.1 Hz, H-3ax), 3.44 (3H, s, 4OCH3), 3.47 (1H, m, Ha-6), 3.57- 3.62 (1H, m, Hb-6), 3.77 (3H, s, 4'OCH3), 4.97 (1H, d, J = 8.0Hz, H-1), 5.46 ( 1H, dd, J = 3.2; 12.3 Hz, H-2), 5.88 (1H, d, J = 2.1 Hz, H-6), 5.90 (1H, d, J = 2.1 Hz, H-8), 7.00 (1H, d, J = 8.3 Hz, H-5 '), 7.07 (1H, dd, J = 2.1; 8.3 Hz, H-6 '), 7.21 (1H, d, J = 2.1 Hz, H-2'), 12.14 (1H, s, 5-OH), 13 C NMR (150 MHz, DMSO-d6 ) δ (ppm): 41.90 (C-3), 55.71 (4'OCH3), 59.79 (C-4-OCH3), 60.12 (C-6), 73.35 (C- 2), 76.64 (C-3), 75.55 (C-5), 78.39 (C-2), 79.19 (C-4), 95.07 (C-8), 95, 43 (C-6), 99.20 (C-1 a), 99.27 (C-1b), 101.77 (C-10), 112.20 (C-5 '), 113.63 (C -2 '), 120.57 (C-6'), 130.82 (C-1'a), 130.88 (C-1'a), 146.48 (C-3 '), 149.11 (C- 4 '), 162.62 (C-9a), 162.67 (C-9b), 163.48 (C-5), 166.77 (C-7), 196.26 (C-4 ).
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| PL422147A PL237334B1 (en) | 2017-07-07 | 2017-07-07 | 7-O-β-D-4'''-O-methyl-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone and 3'-O-β-D-4'''-O-methyl-glucopyranozyl-5,7-dihydroxy-4'-methoxyflavanone and method for simultaneously obtaining of 7-O-β-D-4'''-O-methyl-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone and 3'-O-β-D-4'''-O-methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone |
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| PL422147A PL237334B1 (en) | 2017-07-07 | 2017-07-07 | 7-O-β-D-4'''-O-methyl-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone and 3'-O-β-D-4'''-O-methyl-glucopyranozyl-5,7-dihydroxy-4'-methoxyflavanone and method for simultaneously obtaining of 7-O-β-D-4'''-O-methyl-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone and 3'-O-β-D-4'''-O-methyl-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone |
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