PL233418B1 - Method for producing optically pure (+)-(R)-7-hydroxyflavanone - Google Patents
Method for producing optically pure (+)-(R)-7-hydroxyflavanoneInfo
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- PL233418B1 PL233418B1 PL41394915A PL41394915A PL233418B1 PL 233418 B1 PL233418 B1 PL 233418B1 PL 41394915 A PL41394915 A PL 41394915A PL 41394915 A PL41394915 A PL 41394915A PL 233418 B1 PL233418 B1 PL 233418B1
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- hydroxy flavanone
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- hydroxyflavanone
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- SWAJPHCXKPCPQZ-CQSZACIVSA-N (2R)-7-hydroxyflavanone Chemical compound C1([C@H]2CC(=O)C3=CC=C(C=C3O2)O)=CC=CC=C1 SWAJPHCXKPCPQZ-CQSZACIVSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- SWAJPHCXKPCPQZ-UHFFFAOYSA-N ddC Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=CC=C1 SWAJPHCXKPCPQZ-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 13
- SWAJPHCXKPCPQZ-AWEZNQCLSA-N 7-Hydroxyflavanone Natural products C1([C@@H]2CC(=O)C3=CC=C(C=C3O2)O)=CC=CC=C1 SWAJPHCXKPCPQZ-AWEZNQCLSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 5
- 230000009466 transformation Effects 0.000 claims description 5
- 241000228245 Aspergillus niger Species 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000036983 biotransformation Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- USMZEYPOTJAYPT-LRROQMAJSA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O.O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 USMZEYPOTJAYPT-LRROQMAJSA-N 0.000 description 1
- CILPHQCEVYJUDN-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-ylcyclohexyl)oxyacetic acid Chemical class CC(C)C1CCC(C)CC1OCC(O)=O CILPHQCEVYJUDN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001306121 Dracaena <Squamata> 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 240000002529 Muntingia calabura Species 0.000 description 1
- 235000003886 Muntingia calabura Nutrition 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002001 anti-metastasis Effects 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
- 235000008696 isoflavones Nutrition 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 201000002740 oral squamous cell carcinoma Diseases 0.000 description 1
- 229940124606 potential therapeutic agent Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- REFJWTPEDVJJIY-UHFFFAOYSA-N quercetin Natural products C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 208000020029 respiratory tract infectious disease Diseases 0.000 description 1
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 1
- 235000005493 rutin Nutrition 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest sposób wytwarzania (+)-(R)-7-hydroksyflawanonu o wzorze 2, przedstawionym na rysunku.The present invention relates to a process for the preparation of (+) - (R) -7-hydroxy flavanone of the formula II shown in the drawing.
Związek ten może znaleźć zastosowanie jako antyoksydant w przemyśle spożywczym oraz jako składnik środków farmaceutycznych i kosmetycznych.This compound can be used as an antioxidant in the food industry and as a component of pharmaceutical and cosmetic products.
Flawonoidy to wtórne metabolity roślin o potencjale biologicznym pozwalającym na wykorzys tywanie ich jako farmaceutyki (Calcium Duo Allergo - kwercetyna, Rutinoscorbin® - rutyna, MenoStop® - izoflawony) (B. H. Havsteen, Pharmacology & Therapeutics, 2002, 96, 67-202, I. Erlund, Nutrition Research, 2004, 24, 851-874).Flavonoids are secondary metabolites of plants with biological potential allowing them to be used as pharmaceuticals (Calcium Duo Allergo - quercetin, Rutinoscorbin® - rutin, MenoStop® - isoflavones) (BH Havsteen, Pharmacology & Therapeutics, 2002, 96, 67-202, I. Erlund, Nutrition Research, 2004, 24, 851-874).
Występowanie 7-hydroksyflawanonu udowodniono w szeregu roślin mających zastosowanie w ziołolecznictwie lub mogących być w przyszłości wykorzystane jako składniki leków. S enancjomer 7-hydroksyflawanonu został wyizolowany m.in. z Dracena loureiri i Muntingia calabura (W.-L. Kuo, H.-R. Liao, J.-J. Chen, Molecules, 2014, 19 (12), 20521-20535, B.-N. Su, E. J. Park, J. S. Vigo, J. G. Graham, F. Cabieses, H. H. S., Fong, J. M. Pezzuto, A. D. Kinghorn, Phytochemistry, 2003, 63 (3), 335341, N. P. Lopes, M. J. Kato, M. Yoshida, Phytochemistry, 1999, 51, 29-33, D. Meksuriyen. G. A. Cordell, Journal of the Science Society of Thailand, 1988, 14, 3-24).The occurrence of 7-hydroxy flavanone has been proven in a number of plants that are used in herbal medicine or may be used in the future as drug components. The S enantiomer of 7-hydroxy flavanone has been isolated e.g. with Dracaena loureiri and Muntingia calabura (W.-L. Kuo, H.-R. Liao, J.-J. Chen, Molecules, 2014, 19 (12), 20521-20535, B.-N. Su, EJ Park , JS Vigo, JG Graham, F. Cabieses, HHS, Fong, JM Pezzuto, AD Kinghorn, Phytochemistry, 2003, 63 (3), 335341, NP Lopes, MJ Kato, M. Yoshida, Phytochemistry, 1999, 51, 29- 33, D. Mexuriyen. GA Cordell, Journal of the Science Society of Thailand, 1988, 14, 3-24).
Istnieje szereg badań dotyczących 7-hydroksyflawanonu jako potencjalnego środka terapeutycznego. Związek ten wykazuje aktywność przeciwbakteryjną w stosunku do Streptococcus pneumoniae i może być stosowany w leczeniu infekcji dróg oddechowych (I. C. Zampini, Journal of Ethnopharmacology, 2012, 140, 287-292). Udowodniono, że 7-hydroksyflawanon ma właściwości przeciwprzerzutowe w stosunku do komórek SCC-4 (ludzki płaskonabłonkowy rak jamy ustnej) (Shun-Fa Yang, Archives of oral biology, 2008, 53, 287-294). Ponadto, 7-hydroksyflawanon wykazuje aktywność immunomodulującą (M. L. Sharma, Phytomedicine, 1996, 3 (2), 191-195).There are a number of studies regarding 7-hydroxy flavanone as a potential therapeutic agent. This compound has antibacterial activity against Streptococcus pneumoniae and can be used in the treatment of respiratory tract infections (I. C. Zampini, Journal of Ethnopharmacology, 2012, 140, 287-292). 7-Hydroxy flavanone has been shown to have antimetastatic properties against SCC-4 cells (human oral squamous cell carcinoma) (Shun-Fa Yang, Archives of oral biology, 2008, 53, 287-294). Moreover, 7-hydroxy flavanone exhibits immunomodulatory activity (M. L. Sharma, Phytomedicine, 1996, 3 (2), 191-195).
Znana jest metoda otrzymywania R enancjomeru 7-hydroksyflawanonu w wyniku krystalizacji frakcjonowanej (-)-mentyloksyoctanów i łagodnej kwasowej hydrolizy mniej rozpuszczalnego diastereoizomeru (G. Cardillo, L. Merlini, G. Nasini, Journal of the Chemical Society C: Organic, 1971, 3967-3970).There is a known method of obtaining the R enantiomer of 7-hydroxy flavanone by fractional crystallization of (-) - menthyloxyacetates and mild acidic hydrolysis of the less soluble diastereoisomer (G. Cardillo, L. Merlini, G. Nasini, Journal of the Chemical Society C: Organic, 1971, 3967 -3970).
Do tej pory nie uzyskano R enancjomeru 7-hydroksyflawanonu metodą ekstrakcji z materiału roślinnego ani na drodze biotransformacji.So far, the R enantiomer of 7-hydroxy flavanone has not been obtained by extraction from plant material or by biotransformation.
Biotransformacje to przyjazna dla środowiska naturalnego alternatywa w stosunku do syntezy chemicznej. Biokatalizatory mogą modyfikować strukturę związków, co prowadzi do powstania metabolitów np. o zwiększonych właściwościach antyoksydacyjnych i lipofilowych poprawiających ich biodostępność i aktywność biologiczną (E. Kostrzewa-Susłow, J. Dmochowska-Gładysz, J. Oszmiański, Journal of Molecular Catalysis B: Enzymatic, 2007, 49 (1—4), 113-117, W. A. Loughlin, Bioresource Technology, 2000, 74, 49-62).Biotransformation is an environmentally friendly alternative to chemical synthesis. Biocatalysts can modify the structure of compounds, leading to the formation of metabolites, e.g. with increased antioxidant and lipophilic properties, improving their bioavailability and biological activity (E. Kostrzewa-Susłow, J. Dmochowska-Gładysz, J. Oszmiański, Journal of Molecular Catalysis B: Enzymatic, 2007, 49 (1-4), 113-117, WA Loughlin, Bioresource Technology, 2000, 74, 49-62).
Istotne są badania mające na celu uzyskanie czystych optycznie substancji naturalnych cechujących się właściwościami przeciwutleniającymi, które mogą być wykorzystane w przemyśle farmaceutycznym, ale też kosmetycznym i spożywczym.Research aimed at obtaining optically pure natural substances with antioxidant properties, which can be used in the pharmaceutical, cosmetics and food industries, is important.
Istota wynalazku polega na tym, że do podłoża odpowiedniego dla grzybów strzępkowych wprowadza się szczep Aspergillus niger KB. Po upływie co najmniej 48 godzin do hodowli wprowadza się substrat, którym jest (±)-octan 7-hydroksyflawanonu o wzorze 1, rozpuszczony w rozpuszczalniku organicznym mieszającym się z wodą. Transformację prowadzi się przy ciągłym wstrząsaniu, co najwyżej 30 godzin. Kolejno produkt ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą i oczyszcza chromatograficznie.The essence of the invention consists in introducing a strain of Aspergillus niger KB into a medium suitable for filamentous fungi. After at least 48 hours, a substrate is introduced into the culture, which is 7-hydroxy flavanone (±) -acetate of the formula I, dissolved in a water-miscible organic solvent. The transformation is carried out under continuous shaking for 30 hours at most. Subsequently, the product is extracted with a water-immiscible organic solvent and purified by chromatography.
Korzystnie jest, gdy stosunek masy dodawanego substratu do objętości hodowli wynosi 0,1 mg : 1 mL.Preferably, the ratio of the weight of the substrate added to the culture volume is 0.1 mg: 1 mL.
Korzystnie także jest, gdy proces prowadzi się w temperaturze od 20 do 30 stopni Celsjusza, zwłaszcza 25 stopni Celsjusza.It is also preferred that the process is carried out at a temperature of 20 to 30 degrees Celsius, especially 25 degrees Celsius.
Dodatkowo, korzystnie jest, gdy transformację prowadzi się przez 24 godziny.Additionally, it is preferred that the transformation is carried out for 24 hours.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w komórkach szczepu Aspergillus niger KB, następuje deestryfikacja przy C-7. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem, przez ekstrakcję rozpuszczalnikiem organicznym niemieszającym się z wodą (octan etylu).In accordance with the invention, deesterification at C-7 occurs as a result of the enzyme system contained in the cells of the Aspergillus niger KB 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).
Zasadniczą zaletą wynalazku jest otrzymanie (+)-(R)-7-hydroksyflawanonu z nadmiarem enancjomerycznym wynoszącym 100% ee, w temperaturze pokojowej i przy pH naturalnym dla szczepu.The main advantage of the invention is the preparation of (+) - (R) -7-hydroxy flavanone with an enantiomeric excess of 100% ee, at room temperature and at the natural pH of the strain.
PL 233 418 B1PL 233 418 B1
Wynalazek jest bliżej objaśniony na przykładzie wykonania.The invention is explained in more detail using an exemplary embodiment.
P r z y k ł a d. Do kolby Erlenmajera o pojemności 2000 cm3, w której znajduje się 500 cm3 sterylnej pożywki zawierającej 10 g aminobaku i 30 g glukozy, wprowadza się szczep A. niger KB. Po 96 godzinach jego wzrostu dodaje się 50 mg (±)-octanu 7-hydroksyflawanonu o wzorze 1, rozpuszczonego w 1 cm3 tetrahydrofuranu. Transformację prowadzi się w 25 stopniach Celsjusza przy ciągłym wstrząsaniu przez 24 godziny. Następnie mieszaninę poreakcyjną ekstrahuje się trzykrotnie octanem etylu, osusza bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymany ekstrakt oczyszcza się chromatograficznie, używając jako eluentu mieszaniny octanu etylu i chlorku metylenu w stosunku 1:1. Na tej drodze otrzymuje się 25 mg (+)-(R)-7-hydroksyflawanonu (wydajność 50%).Example d. To the Erlenmeyer flask with a capacity of 2,000 cm 3, which is 500 cm 3 of a sterile medium containing 10 g aminobaku and 30 g of glucose, introduced into A. niger strain KB. After 96 hours of its growth, 50 mg of 7-hydroxy flavanone (1) acetate, dissolved in 1 cm 3 of tetrahydrofuran, are added. The transformation is performed at 25 degrees Celsius with continuous shaking for 24 hours. Then, the reaction mixture was extracted three times with ethyl acetate, dried with anhydrous magnesium sulfate and the solvent was evaporated. The extract obtained is purified by chromatography using a 1: 1 mixture of ethyl acetate and methylene chloride as eluent. In this way, 25 mg of (+) - (R) -7-hydroxy flavanone are obtained (50% yield).
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi.The obtained product is characterized by the following spectral data.
Opis sygnałów pochodzących z widma 1H NMR (THF-d8): δ = 7.72 ppm (1H, d, J5,6 = 8.3 Hz, H-5), δ = 7.49 ppm (2H, d, J2-,3-(6-,5·) = 7.5 Hz, H-2', H-6'), δ = 7.37 ppm (2H, t, J3-,2-(5-,6·) = 7.5 Hz, H-3', H-5'), δ = 7.31 ppm (1H, t, J = 7.3 Hz, H-4'), δ = 6.45 ppm (1H, dd, Jąs = 8.7 Hz, Jąs = 1.9 Hz, H-6), δ = 6.34 ppm (1H, d, Js,6 = 2.3 Hz, H-8), δ = 5.45 ppm (1H, dd, J2,3ax = 12.99 Hz, J2,3eq = 2.82 Hz, H-2), δ = 2.93 ppm (1H, dd, J3ax,3eq = 16.6 Hz, J3ax,2 = 13.2 Hz, H-3ax), δ = 2.68 ppm (1H, dd, J3eq,3ax = 16.6 Hz, J3eq,2 = 3.0 Hz, H-3eq).Description of signals from the 1H NMR spectrum (THF-d8): δ = 7.72 ppm (1H, d, J5.6 = 8.3 Hz, H-5), δ = 7.49 ppm (2H, d, J2-, 3- (6 -, 5 ·) = 7.5 Hz, H-2 ', H-6'), δ = 7.37 ppm (2H, t, J3-, 2- (5-, 6) = 7.5 Hz, H-3 ', H-5 '), δ = 7.31 ppm (1H, t, J = 7.3 Hz, H-4'), δ = 6.45 ppm (1H, dd, Jąs = 8.7 Hz, Js = 1.9 Hz, H-6), δ = 6.34 ppm (1H, d, Js, 6 = 2.3 Hz, H-8), δ = 5.45 ppm (1H, dd, J2.3ax = 12.99 Hz, J2.3eq = 2.82 Hz, H-2), δ = 2.93 ppm (1H, dd, J3ax, 3eq = 16.6 Hz, J3ax, 2 = 13.2 Hz, H-3ax), δ = 2.68 ppm (1H, dd, J3eq, 3ax = 16.6 Hz, J3eq, 2 = 3.0 Hz, H-3eq).
Opis sygnałów pochodzących z widma 13C NMR (THF-d8): δ = 188.52 ppm (C-4), δ = 164.54 ppm (07), δ = 163.41 ppm (C-9), δ =139.90 ppm (C-1'), δ = 128.47 ppm (C-5), δ = 128.30 ppm (C-3', C-5’), δ = 128.04 ppm (C-4'), δ = 126.09 ppm (C-2', C-6'), δ = 114.26 ppm (C-10), δ = 110.23 ppm (C-6), δ = 102.56 ppm (C-8), δ = 79.84 ppm (C-2), δ = 44.25 ppm (C-3).Description of signals from the 13 C NMR spectrum (THF-d8): δ = 188.52 ppm (C-4), δ = 164.54 ppm (07), δ = 163.41 ppm (C-9), δ = 139.90 ppm (C-1) '), δ = 128.47 ppm (C-5), δ = 128.30 ppm (C-3', C-5 '), δ = 128.04 ppm (C-4'), δ = 126.09 ppm (C-2 ', C-6 '), δ = 114.26 ppm (C-10), δ = 110.23 ppm (C-6), δ = 102.56 ppm (C-8), δ = 79.84 ppm (C-2), δ = 44.25 ppm (C-3).
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL41394915A PL233418B1 (en) | 2015-09-14 | 2015-09-14 | Method for producing optically pure (+)-(R)-7-hydroxyflavanone |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL41394915A PL233418B1 (en) | 2015-09-14 | 2015-09-14 | Method for producing optically pure (+)-(R)-7-hydroxyflavanone |
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| Publication Number | Publication Date |
|---|---|
| PL413949A1 PL413949A1 (en) | 2017-03-27 |
| PL233418B1 true PL233418B1 (en) | 2019-10-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| PL41394915A PL233418B1 (en) | 2015-09-14 | 2015-09-14 | Method for producing optically pure (+)-(R)-7-hydroxyflavanone |
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| Country | Link |
|---|---|
| PL (1) | PL233418B1 (en) |
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| Publication number | Publication date |
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| PL413949A1 (en) | 2017-03-27 |
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