PL233277B1 - 7-propoxy-naringenin, 7,4'-dipropoxy-naringenin and method for simultaneously obtaining 7-propoxy-naringenin and 7,4'-dipropoxy-naringenin - Google Patents
7-propoxy-naringenin, 7,4'-dipropoxy-naringenin and method for simultaneously obtaining 7-propoxy-naringenin and 7,4'-dipropoxy-naringeninInfo
- Publication number
- PL233277B1 PL233277B1 PL422924A PL42292417A PL233277B1 PL 233277 B1 PL233277 B1 PL 233277B1 PL 422924 A PL422924 A PL 422924A PL 42292417 A PL42292417 A PL 42292417A PL 233277 B1 PL233277 B1 PL 233277B1
- Authority
- PL
- Poland
- Prior art keywords
- naringenin
- organic solvent
- formula
- propoxynaringenin
- dipropoxynaringenin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 229940117954 naringenin Drugs 0.000 title claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WGEYAGZBLYNDFV-UHFFFAOYSA-N naringenin Natural products C1(=O)C2=C(O)C=C(O)C=C2OC(C1)C1=CC=C(CC1)O WGEYAGZBLYNDFV-UHFFFAOYSA-N 0.000 claims description 6
- 235000007625 naringenin Nutrition 0.000 claims description 6
- FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims description 5
- 235000015320 potassium carbonate Nutrition 0.000 claims description 5
- 235000011181 potassium carbonates Nutrition 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 241000395050 Kaempferia parviflora Species 0.000 description 1
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 description 1
- 206010061306 Nasopharyngeal cancer Diseases 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- -1 alkyl naringenin derivatives Chemical class 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000004090 dissolution Methods 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
- 235000013305 food Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest 7-propoksynaringenina. Przedmiotem jest także 7,4'-dipropoksynaringenina. Przedmiotem wynalazku jest również sposób jednoczesnego otrzymywania 7-propoksynaringeniny oraz 7,4'-dipropoksynaringeniny.The present invention relates to 7-propoxynaringenin. The subject is also 7,4'-dipropoxynaringenin. The invention also relates to a method for the simultaneous preparation of 7-propoxynaringenin and 7,4'-dipropoxynaringenin.
Obecny stan wiedzy dowodzi aktywności cytotoksycznej alkilowych pochodnych naringeniny względem linii komórkowych nowotworu jamy nosowo-gardłowej (KB) oraz drobnokomórkowego raka płuc (NCI-H187) (C. Yenjai, S. Wanich, “Cytotoxicity against KB and NCI-H187 cell lines of modified flavonoids from Kaempferia parviflora, Bioorg. Med. Chem. Lett., 2010, 20, 2821-2823), a także względem nowotworu piersi (MCF-7) (J. Park et al., „Cytotoxic Effects of 7-O-butyl Naringenin on Human Breast Cancr MCF-7 Cells”, Food Sci. Biotechnol., 2010, 19, 77-724).The current state of knowledge proves the cytotoxic activity of alkyl naringenin derivatives against nasopharyngeal cancer (KB) and small cell lung cancer (NCI-H187) cell lines (C. Yenjai, S. Wanich, "Cytotoxicity against KB and NCI-H187 cell lines of modified flavonoids from Kaempferia parviflora, Bioorg. Med. Chem. Lett., 2010, 20, 2821-2823), and in relation to breast cancer (MCF-7) (J. Park et al., "Cytotoxic Effects of 7-O-butyl Naringenin on Human Breast Cancr MCF-7 Cells ”, Food Sci. Biotechnol., 2010, 19, 77-724).
W dostępnej literaturze nie znaleziono doniesień na temat 7-propoksynaringeniny oraz 7,4'-dipropoksynaringeniny i sposobu ich otrzymywania.There are no reports on 7-propoxynaringenin and 7,4'-dipropoxynaringenin and the method of their preparation in the available literature.
Istotą wynalazku jest 7-propoksynaringenina. Istotą jest również 7,4'-dipropoksynaringenina.The essence of the invention is 7-propoxynaringenin. The essence is also 7,4'-dipropoxynaringenin.
Istotą jest także sposób otrzymywania 7-propoksynaringeniny oraz 7,4'-dipropoksynaringeniny, polegający na tym, że do naringeniny o wzorze 1 dodaje się węglan potasu K2CO3 oraz 1-jodopropan w stosunku molowym co najmniej 1:1,5:5 oraz minimalną ilość rozpuszczalnika organicznego. Stanowi to mieszaninę reakcyjną, którą zabezpiecza się przed dostępem światła i pozostawia w temperaturze od 25°C do 45°C na okres od 24 do 72 godzin przy ciągłym mieszaniu. Po tym czasie rozpuszczalnik organiczny się odparowuje, a następnie dodaje się nasyconego roztworu chlorku sodu NaCI i prowadzi się ekstrakcję rozpuszczalnikiem organicznym niemieszającym się z wodą, osusza bezwodnym siarczanem magnezu i/lub bezwodnym siarczanem sodu, a rozpuszczalnik odparowuje się. Otrzymany ekstrakt oczyszcza się na kolumnie chromatograficznej.The essence is also the method of obtaining 7-propoxynaringenin and 7,4'-dipropoxynaringenin, consisting in adding potassium carbonate K2CO3 and 1-iodopropane in a molar ratio of at least 1: 1.5: 5 to naringenin of formula 1, and a minimum amount of organic solvent. This is a reaction mixture that is protected from light and left at 25 ° C to 45 ° C for 24 to 72 hours with constant stirring. After this time, the organic solvent is evaporated, then a saturated solution of sodium chloride NaCl is added and extraction is carried out with a water-immiscible organic solvent, dried with anhydrous magnesium sulfate and / or anhydrous sodium sulfate, and the solvent is evaporated. The obtained extract is purified by column chromatography.
Korzystnie jest, gdy stosunek molowy naringeniny o wzorze 1 do węglanu potasu K2CO3 oraz 1-jodopropan wynosi 1:1,5:5, przy temperaturze reakcji 40°C, w czasie 48 godzin.It is preferred that the molar ratio of naringenin I to potassium carbonate K2CO3 and 1-iodopropane is 1: 1.5: 5 at a reaction temperature of 40 ° C for 48 hours.
Korzystne jest, gdy rozpuszczalnikiem organicznym stosowanym do reakcji jest aceton.It is preferred that the organic solvent used for the reaction is acetone.
Korzystnie również jest, gdy rozpuszczalnikiem organicznym stosowanym do ekstrakcji jest octan etylu.It is also preferred that the organic solvent used for the extraction is ethyl acetate.
Korzystnym jest, gdy, eluent stosowany do oczyszczania na kolumnie chromatograficznej stanowi mieszanina heksanu, chlorku metylenu i octanu etylu w stosunku objętościowym 5:1:1.It is preferred that the eluent used for the purification by the column chromatography is a mixture of hexane, methylene chloride and ethyl acetate in a 5: 1: 1 volume ratio.
Zasadniczą zaletą wynalazku jest otrzymanie 7-propoksynaringeniny z wydajnością bliską 62%, przy jednoczesnym otrzymaniu 7,4'-dipropoksynaringeniny z wydajnością sięgającą 28% z użyciem łatwo dostępnych odczynników.The main advantage of the invention is the preparation of 7-propoxynaringenin with the efficiency close to 62%, while at the same time obtaining 7,4'-dipropoxynaringenin with the efficiency reaching 28% with the use of readily available reagents.
Sposób wykonania wynalazku objaśniony jest w przykładzie wykonania.The embodiment of the invention is explained in an embodiment.
P r z y k ł a d: W kolbie okrągłodennej zaopatrzonej w mieszadło magnetyczne umieszcza się 2 g naringeniny o wzorze 1 oraz 1,5229 g węglanu potasu K2CO3 i dodaje się 20 mL acetonu. Po rozpuszczeniu dodaje się kroplami do mieszaniny reakcyjnej 3,58 mL 1-jodopropanu. Reakcję zabezpiecza się przed dostępem światła i kontynuuje mieszanie przez 48 godzin utrzymując temperaturę 40°C. Po tym czasie, rozpuszczalnik odparowuje się i dodaje się 40 mL nasyconego roztworu chlorku sodu NaCI, a następnie prowadzi się 3-krotną ekstrakcję 30 mL octanu etylu. Połączone warstwy organiczne osusza się nad bezwodnym siarczanem sodu, rozpuszczalnik odparowuje się na wyparce próżniowej. Otrzymany surowy ekstrakt oczyszcza się na kolumnie chromatograficznej stosując, jako eluent mieszaninę heksanu, chlorku metylenu i octanu etylu w stosunku objętościowym 5:1:1. Na tej drodze otrzymuje się 1,4282 g 7-propoksynaringeniny w postaci białego proszku z wydajnością 61,85% oraz 0,7412 g 7,4'-dipropoksynaringeniny w postaci białego proszku z wydajnością 28,31%.Example 2: 2 g of naringenin of formula I and 1.5229 g of potassium carbonate K2CO3 are placed in a round-bottom flask equipped with a magnetic stirrer, and 20 mL of acetone are added. After dissolution, 3.58 mL of 1-iodopropane is added dropwise to the reaction mixture. The reaction is protected from light and stirring is continued for 48 hours while maintaining the temperature at 40 ° C. After this time, the solvent is evaporated off and 40 mL of saturated sodium chloride NaCl solution is added, followed by 3-fold extraction with 30 mL of ethyl acetate. The combined organic layers are dried over anhydrous sodium sulfate, the solvent is evaporated off in a vacuum evaporator. The obtained crude extract is purified by column chromatography using a 5: 1: 1 v / v mixture of hexane, methylene chloride and ethyl acetate as eluent. In this way, 1.4282 g of 7-propoxynaringenin in the form of a white powder with a yield of 61.85% and 0.7412 g of 7.4'-dipropoxynaringenin in the form of a white powder with a yield of 28.31% are obtained.
Stałe fizyczne i spektroskopowe otrzymanych związków są następujące:The physical and spectroscopic constants of the compounds obtained are as follows:
7-propoksynaringenina:7-propoxynaringenin:
Temp. topnienia (°C): 155-157 1H NMR (600 MHz, Chloroform-d) δ [ppm]: 12,01 (s, 1H, OH-5), 7,36 - 7,30 (m, 2H, AA'BB', H-2', H-6'), 6,91 - 6,85 (m, 2H, AA'BB', H-3', H-5'), 6,06 (d, J = 2,3 Hz, 1H, H-6), 6,03 (d, J = 2,3 Hz, 1H, H-8), 5,35 (dd, J = 13,0, 3,0 Hz, 1H, H-2), 5,20 (s, 1H, OH-4'), 3,92 (t, J = 6,6 Hz, 2H, -CH2-), 3,08 (dd, J = 17,1, 13,0 Hz, 1H, H-3a), 2,78 (dd, J = 17,1, 3,0 Hz, 1H, H-3b), 1,83 - 1,75 (m, 2H, -CH2-), 1,01 (t, J = 7,4 Hz, 3H, -CH3)Temp. mp (° C): 155-157 1 H NMR (600 MHz, Chloroform-d) δ [ppm]: 12.01 (s, 1H, OH-5), 7.36 - 7.30 (m, 2H, AA'BB ', H-2', H-6 '), 6.91 - 6.85 (m, 2H, AA'BB', H-3 ', H-5'), 6.06 (d, J = 2.3 Hz, 1H, H-6), 6.03 (d, J = 2.3 Hz, 1H, H-8), 5.35 (dd, J = 13.0, 3.0 Hz , 1H, H-2), 5.20 (s, 1H, OH-4 '), 3.92 (t, J = 6.6 Hz, 2H, -CH2-), 3.08 (dd, J = 17.1, 13.0 Hz, 1H, H-3a), 2.78 (dd, J = 17.1, 3.0 Hz, 1H, H-3b), 1.83 - 1.75 (m, 2H, -CH2-), 1.01 (t, J = 7.4Hz, 3H, -CH3)
7,4'-dipropoksynaringenina:7,4'-dipropoxynaringenin:
Temp. topnienia (°C): 93-96Temp. mp (° C): 93-96
PL 233 277 B1 1H NMR (600 MHz, Chloroform-d) δ [ppm]: 12,02 (s, 1H, OH-5), 7,39 - 7,33 (m, 2H, AA'BB', H-2', H-6'), 6,97 - 6,91 (m, 2H, AA'BB', H-3', H-5'), 6,05 (d, J = 2,3 Hz, 1H, H-6), 6,03 (d, J = 2,3 Hz, 1H, H-8), 5,35 (dd, J = 13,0, 3,0 Hz, 1H, H-2), 3,94 (t, J = 6,6 Hz, 2H, -CH2-), 3,92 (t, J = 6,6 Hz, 2H, -CH2-), 3,09 (dd, J = 17,1, 13,0 Hz, 1H, H-3a), 2,77 (dd, J = 17,1, 3,0 Hz, 1H, H-3b), 1,86 - 1,75 (m, 4H, -2x -CH2-), 1,04 (t, J = 7,4 Hz, 3H, -CH3-), 1,01 (t, J = 7,4 Hz, 3H, -CH3).GB 1 233 277 B1 H NMR (600 MHz, CHLOROFORM-d) δ [ppm]: 12.02 (s, 1H, OH-5), 7.39 - 7.33 (m, 2H, AA 'BB', H-2 ', H-6'), 6.97 - 6.91 (m, 2H, AA'BB ', H-3', H-5 '), 6.05 (d, J = 2.3 Hz, 1H, H-6), 6.03 (d, J = 2.3 Hz, 1H, H-8), 5.35 (dd, J = 13.0, 3.0 Hz, 1H, H- 2), 3.94 (t, J = 6.6 Hz, 2H, -CH2-), 3.92 (t, J = 6.6 Hz, 2H, -CH2-), 3.09 (dd, J = 17.1, 13.0 Hz, 1H, H-3a), 2.77 (dd, J = 17.1, 3.0 Hz, 1H, H-3b), 1.86 - 1.75 (m , 4H, -2x -CH2-), 1.04 (t, J = 7.4Hz, 3H, -CH3-), 1.01 (t, J = 7.4Hz, 3H, -CH3).
Claims (7)
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| PL422924A PL233277B1 (en) | 2017-09-21 | 2017-09-21 | 7-propoxy-naringenin, 7,4'-dipropoxy-naringenin and method for simultaneously obtaining 7-propoxy-naringenin and 7,4'-dipropoxy-naringenin |
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| PL422924A PL233277B1 (en) | 2017-09-21 | 2017-09-21 | 7-propoxy-naringenin, 7,4'-dipropoxy-naringenin and method for simultaneously obtaining 7-propoxy-naringenin and 7,4'-dipropoxy-naringenin |
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| Publication Number | Publication Date |
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| PL422924A1 PL422924A1 (en) | 2019-03-25 |
| PL233277B1 true PL233277B1 (en) | 2019-09-30 |
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| KR100898330B1 (en) * | 2007-09-12 | 2009-05-20 | 건국대학교 산학협력단 | Novel flavonoid derivatives 7-O- (3-benzyloxypropyl) -5,4'-O-dimethyl-apigenin having anticancer properties, preparations thereof and anticancer compositions comprising the same |
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