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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- 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
- 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
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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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