PL236832B1 - Method for obtaining 3'-O-β-D-glucopyranosyl-5.7-dihydroxy-4'-methoxyflavanone - Google Patents
Method for obtaining 3'-O-β-D-glucopyranosyl-5.7-dihydroxy-4'-methoxyflavanone Download PDFInfo
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- PL236832B1 PL236832B1 PL422811A PL42281117A PL236832B1 PL 236832 B1 PL236832 B1 PL 236832B1 PL 422811 A PL422811 A PL 422811A PL 42281117 A PL42281117 A PL 42281117A PL 236832 B1 PL236832 B1 PL 236832B1
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- Prior art keywords
- glucopyranosyl
- dihydroxy
- methoxyflavone
- transformation
- absidia coerulea
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- 238000000034 method Methods 0.000 title claims abstract description 17
- 241000293029 Absidia caerulea Species 0.000 claims abstract description 12
- 230000009466 transformation Effects 0.000 claims abstract description 11
- 239000000758 substrate Substances 0.000 claims abstract description 7
- QAGGICSUEVNSGH-UHFFFAOYSA-N Diosmetin Natural products C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=CC=C(O)C=C2O1 QAGGICSUEVNSGH-UHFFFAOYSA-N 0.000 claims abstract description 3
- MBNGWHIJMBWFHU-UHFFFAOYSA-N diosmetin Chemical group C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 MBNGWHIJMBWFHU-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000002906 microbiologic effect Effects 0.000 claims abstract description 3
- 241000233866 Fungi Species 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 230000000813 microbial effect Effects 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
- 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
- 238000003756 stirring Methods 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 abstract description 3
- 108090000790 Enzymes Proteins 0.000 abstract description 3
- 235000013305 food Nutrition 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 241000689297 Saussurea stella Species 0.000 description 4
- 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
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 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
- 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
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 flavone glycosides Chemical class 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229930182487 phenolic glycoside Natural products 0.000 description 2
- 150000007950 phenolic glycosides Chemical class 0.000 description 2
- 244000062995 Cassia occidentalis Species 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
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent 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
- 238000000605 extraction Methods 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 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)
- Pyrane Compounds (AREA)
Abstract
Zgłoszenie dotyczy sposobu otrzymywania 3'-O-ßS-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawonu, o wzorze 2, na drodze transformacji mikrobiologicznej, przy użyciu systemu enzymatycznego grzybów z gatunku Absidia coerulea, gdzie jako substrat stosuje się 3',5,7-trihydroksy-4'-metoksyflawon o wzorze 1. Związek będący przedmiotem zgłoszenia jest biologicznie czynny i może mieć zastosowanie w przemyśle spożywczym i farmaceutycznym.The application concerns a method for obtaining 3'-O-ßS-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavone, of the formula 2, by microbiological transformation, using the enzyme system of the Absidia coerulea fungus, where the substrate is 3',5,7-trihydroxy-4'-methoxyflavone of the formula 1. The subject of the application is biologically active and can be used in the food and pharmaceutical industries.
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest sposób otrzymywania 3'-O-3-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawonu o wzorze przedstawionym na rysunku.The subject of the invention is a process for the preparation of 3'-O-3-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavone with the formula shown in the drawing.
Budowa chemiczna otrzymanego związku wskazuje na jego aktywność biologiczną oraz potencjalne zastosowanie w przemyśle spożywczym i farmaceutycznym.The chemical structure of the obtained compound indicates its biological activity and potential application in the food and pharmaceutical industries.
W literaturze znany jest 3'-O-3-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawon naturalnie występujący np. w strączyńcu (S. Kitanaka, M. Takido: „Studies of the constituents of the leaves of Cassia torosa Cav. III. The structures of two new flavone glycosides”, Chem. Pharm. Bull., 1992, 40, 249-251) i Saussurea Stella (T.M. Wang, R.F. Wang, H.B. Chen, M.Y. Shang, S.Q. Cai: „Alkyl and phenolic glycosides from Saussurea Stella, Fitoterapia, 2013, 88, 38-43).In the literature, 3'-O-3-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavone is known, naturally occurring e.g. in a pod (S. Kitanaka, M. Takido: "Studies of the constituents of the leaves of Cassia torosa Cav. III. The structures of two new flavone glycosides ", Chem. Pharm. Bull., 1992, 40, 249-251) and Saussurea Stella (TM Wang, RF Wang, HB Chen, MY Shang, SQ Cai:" Alkyl and phenolic glycosides from Saussurea Stella, Fitoterapia, 2013, 88, 38-43).
W literaturze opisana została metoda pozyskiwania tego związku poprzez ekstrakcję z Saussurea stella jednakże z bardzo małą wydajnością wynoszącą 0,003% (T.M. Wang, R.F. Wang, H.B. Chen, M.Y. Shang, S.Q. Cai: „Alkyl and phenolic glycosides from Saussurea stella, Fitoterapia, 2013, 88, 38-43).The literature describes a method of obtaining this compound by extraction from Saussurea stella, however with a very low efficiency of 0.003% (TM Wang, RF Wang, HB Chen, MY Shang, SQ Cai: "Alkyl and phenolic glycosides from Saussurea stella, Fitoterapia, 2013, 88, 38-43).
Nie jest znana metoda otrzymywania 3'-O-3-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawonu na drodze syntezy chemicznej ani transformacji mikrobiologicznej.There is no known method to obtain 3'-O-3-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavone by chemical synthesis or microbiological transformation.
Szczep Absidia coerulea AM93 zdeponowany jest w kolekcji mikroorganizmów Katedry Chemii Uniwersytetu Przyrodniczego we Wrocławiu (ul. C.K. Norwida 25, 50-375 Wrocław).Absidia coerulea AM93 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 Absidia coerulea . Opisano m. in. jego zdolność do glikozylacji związków flawonoidowych. W wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Absidia coerulea otrzymano szereg związków. Z opisu patentowego PL223441(B1) znana jest metoda otrzymywania 4'-O-3-D-glukopiranozylo4,2'-dihydroksy-6'-metoksy-3'-prenylo-a,3-dihydrochalkonu, z opisu PL226315(B1) znany jest sposób otrzymywania 2'-O-3-D-glukopiranozylo-1,2,a,3-tetrahydroksantohumolu C, z PL223446(B1) - 4'-Oβ-D-glukopiranozyloksantohumolu C, opis PL222175(B1) ujawnia otrzymywanie 4'-O-β-D-glukopiranozylo-β-[1'''-hydroksyizopropylo]-4,2'-dihydroksy-6'-metoksy-3'-prenylo-α,β-dihydro-chalkonu, opisBiotransformation processes involving filamentous fungi of the Absidia coerulea species are known. Among others, its ability to glycosylate flavonoid compounds. As a result of the action of the enzyme system contained in living cells of Absidia coerulea culture, a number of compounds were obtained. From the patent description PL223441 (B1) there is known a method for the preparation of 4'-O-3-D-glucopyranosyl-4,2'-dihydroxy-6'-methoxy-3'-prenyl-a, 3-dihydroochalcone, known from PL226315 (B1) is a method for preparing 2'-O-3-D-glucopyranosyl-1,2, a, 3-tetrahydroxanthohumol C, from PL223446 (B1) - 4'-Oβ-D-glucopyranosylxanthohumol C, description PL222175 (B1) discloses the preparation of 4 ' -O-β-D-glucopyranosyl-β- [1 '' - hydroxyisopropyl] -4,2'-dihydroxy-6'-methoxy-3'-prenyl-α, β-dihydro-chalcone, description
PL222731(B1) wskazuje na otrzymywanie mieszaniny 7-O-β-D-glukopiranozylo-5-hydroksy-4'-metoksyizoflawonu i 5-O-β-D-glukopiranozylo-7-hydroksy-4'-metoksyizoflawonu, natomiast PL210084(B1) opisuje otrzymywanie 4'-O-β-D-glukozylo-2',4-dihydroksy-6'-metoksy-3'-prenylochalkonu.PL222731 (B1) indicates the preparation of a mixture of 7-O-β-D-glucopyranosyl-5-hydroxy-4'-methoxyisoflavone and 5-O-β-D-glucopyranosyl-7-hydroxy-4'-methoxyisoflavone, while PL210084 (B1 ) describes the preparation of 4'-O-β-D-glucosyl-2 ', 4-dihydroxy-6'-methoxy-3'-prenylchalcone.
Istotą wynalazku jest sposób otrzymywania 3'-O-β-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawonu, polegający na tym, że substrat, którym jest 3',5,7-trihydroksy-4’-metoksyflawon, poddaje się transformacji mikrobiologicznej, w wyniku czego otrzymuje się 3'-O-β-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawon. Grzyby strzępkowe z gatunku Absidia coerulea 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 proces, aż 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 the method of obtaining 3'-O-β-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavone, consisting in the fact that the substrate, which is 3 ', 5,7-trihydroxy-4'-methoxyflavone, undergoes a microbial transformation to give 3'-O-β-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavone. Filamentous fungi of the species Absidia coerulea 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 także jest, gdy transformację prowadzi się szczepem Absidia coerulea AM93.It is also preferred that the transformation is carried out with the strain Absidia coerulea AM93.
Korzystnie jest, gdy reakcję prowadzi się w temperaturze 26°C.It is advantageous when the reaction is carried out at 26 ° C.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Absidia coerulea następuje reakcja glukozylacji substratu.In accordance with the invention, a glucosylation reaction of the substrate takes place as a result of the enzyme system contained in the living cells of the Absidia coerulea culture.
Zasadniczą zaletą wynalazku jest otrzymanie, w łagodnych warunkach 3'-O-β-D-glukopiranozylo5,7-dihydroksy-4'-metoksyflawonu, jako głównego produktu reakcji w kulturze Absidia coerulea. Wydajność reakcji osiąga poziom ponad 26%.The main advantage of the invention is to obtain, under mild conditions, 3'-O-β-D-glucopyranosyl5,7-dihydroxy-4'-methoxyflavone as the main reaction product in Absidia coerulea culture. The reaction efficiency is over 26%.
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 dP r z k ł a d
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 Absidia coerulea AM93. Po 6 dniach wzrostu drobnoustrojów w temperaturze 26°C i przy ciągłym wstrząsaniu, dodaje się 15 mg 3',5,7-trihydroksy-4’-metoksyflawonu, o wzorze 1, rozpuszczonego w 1,5 cm3 dimetylosulfotlenku. Transformację prowadzi się przy ciągłym wstrząsaniu przez 10 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 magnezuTo 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 fungus Absidia coerulea AM93. After 6 days, the growth of microorganisms at 26 ° C with continuous shaking, is added 15 mg of 3 ', 5,7-trihydroxy-4'-metoksyflawonu of formula 1, dissolved in 1.5 cm 3 of dimethyl sulfoxide. The transformation is carried out under continuous shaking for 10 days. 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.
PL 236 832 B1 i odparowuje rozpuszczalnik. Uzyskuje się 12 mg surowego ekstraktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaninę chloroform : metanol w stosunku objętościowym 7 : 1. Po oczyszczeniu otrzymuje się 6,13 mg 3'-O-3-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawonu, o wzorze 2 z wydajnością 26,5%.And the solvent is evaporated off. 12 mg of crude extract is obtained, which is purified by chromatography using a 7: 1 mixture of chloroform: methanol as eluent. After purification, 6.13 mg of 3'-O-3-D-glucopyranosyl-5,7-dihydroxy are obtained. -4'-methoxyflavone, Formula 2 in a yield of 26.5%.
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
1H NMR (600 MHz, DMSO-d6) δ (ppm): 3,17 (1H, m, H-4), 3,29 (1H, m, H-2), 3,31 (1H, m, H3''), 3,47 (1H, m, H-5), 3,50 (1H, m, Ha-6''), 3,72 (1H, m, Hb-6), 3,87 (3H, s, 4'-OCH3), 5,12 (1H, d, J = 7,3 Hz, H-1''), 6,20 (1H, d, J = 2,1 Hz, H-8), 6,54 (1H, d, J = 2,1 Hz, H-6), 6,90 (1H, s, H-3), 7,16 (1H, m, J = 8,6, H-5'), 7,72 (2H, m, H-2', H-6'), 12,92 (1H, s, 5-OH), 13C NMR (150 MHz, DMSO-d6) δ (ppm): 55,9 (4'-OCH3), 60,7 (C-6), 69,8 (C-4), 73,21 (C-2”), 76,9 (C-3), 77,2 (C-5''), 94,3 (C-6), 99,0 (C-8), 99,9 (C-1), 103,6 (C-10), 103,8 (C-3), 112,4 (C-5'), 113,0 (C-2'), 121,1 (C-6'), 122,9 (C-1'), 146,7 (C-3'), 152,2 (C-4'), 157,4 (C-5), 161,4 (C-9), 163,2 (C-2), 164,7 (C-7), 181,7 (C-4). 1 H NMR (600 MHz, DMSO-d6) δ (ppm): 3.17 (1H, m, H-4), 3.29 (1H, m, H-2), 3.31 (1H, m, H3 "), 3.47 (1H, m, H-5), 3.50 (1H, m, Hb-6"), 3.72 (1H, m, Hb-6), 3.87 ( 3H, s, 4'-OCH 3 ), 5.12 (1H, d, J = 7.3 Hz, H-1 "), 6.20 (1H, d, J = 2.1 Hz, H- 8), 6.54 (1H, d, J = 2.1Hz, H-6), 6.90 (1H, s, H-3), 7.16 (1H, m, J = 8.6, H-5 '), 7.72 (2H, m, H-2', H-6 '), 12.92 (1H, s, 5-OH), 13 C NMR (150 MHz, DMSO-d6) δ (ppm): 55.9 (4'-OCH 3 ), 60.7 (C-6), 69.8 (C-4), 73.21 (C-2 ”), 76.9 (C-3 ), 77.2 (C-5 "), 94.3 (C-6), 99.0 (C-8), 99.9 (C-1), 103.6 (C-10), 103 . 8 (C-3), 112.4 (C-5 '), 113.0 (C-2'), 121.1 (C-6 '), 122.9 (C-1'), 146, 7 (C-3 '), 152.2 (C-4'), 157.4 (C-5), 161.4 (C-9), 163.2 (C-2), 164.7 (C -7), 181.7 (C-4).
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| PL237334B1 (en) | 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 | |
| PL237133B1 (en) | 7-O-β-D-4'''-O-methyl-glucopyranosyl-5-hydroxyflavanone and method for obtaining 7-O-β-D-4'''-O-methyl-glucopyranosyl-5-hydroxyflavanone | |
| PL234137B1 (en) | 7-O-β-D-4'''-O-methyl-glucopyranosyl-5-hydroxy-4'-methoxyisoflavanone and method for obtaining 7-O-β-D-4'''-O-methyl-glucopyranosyl-5-hydroxy-4'-methoxyisoflavanone | |
| PL223444B1 (en) | Method for preparing 1",2",α,β-tetrahydroxanthohumol C | |
| PL223446B1 (en) | 4'-O-β-D-glucopyranosylxanthohumol C and a method for its manufacturing | |
| PL223441B1 (en) | 4'-O-β-D-glucopyranosyl-4, 2'-dihydroxy-6'-methoxy-3'-prenyl-α, β-dihydrochalcone and a process for its preparation | |
| PL237335B1 (en) | 7-O-β-D-4''-O-methyl-glucopyranosyl-4',5-dihydroxyflavanone and method for obtaining 7-O-β-D-4''-O-methyl-glucopyranosyl-4',5-dihydroxyflavanone | |
| PL234087B1 (en) | 7-O-β-D-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone and method for obtaining 7-O-β-D-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone | |
| PL231813B1 (en) | Method for obtaining 7-O-β-D-glucopyranosyl-5,4'-dihydroxyflavone | |
| PL237130B1 (en) | 7-O-β-D-4''-O-methyl-glucopyranosyl-3',4',5-trihydroxyflavanone and method for obtaining 7-O-β-D-4''-O-methyl-glucopyranosyl-3',4',5-trihydroxyflavanone | |
| PL234826B1 (en) | Method for obtaining a mixture of 3'-O-β-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone and 7-O-β-D-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone | |
| PL234658B1 (en) | Method for obtaining 7-O-β-D-glucopyranosyl-5-hydroxyflavone | |
| PL234088B1 (en) | 7-O-β-D-4'''-O-methyl-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone and method for obtaining 7-O-β-D-4'''-O-methyl-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone | |
| PL229155B1 (en) | (Z)-2''-(2' '-hydroxyisopropyl)-dihydrofuran[4'',5'',6,7]-4'-hydroxy-4-metoxiaurone and a method for its preparation | |
| PL223442B1 (en) | 4'-O-β-D-glucopyranosyl-1",2"-dihydroxanthohumol K and its manufacturing process |