PL237129B1 - 3-O-(β-D-4'-O-methylglucopyranosyl)-estrone and method for producing 3-O-(β-D-4'-O-methylglucopyranosyl)-estrone - Google Patents
3-O-(β-D-4'-O-methylglucopyranosyl)-estrone and method for producing 3-O-(β-D-4'-O-methylglucopyranosyl)-estrone Download PDFInfo
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- PL237129B1 PL237129B1 PL422501A PL42250117A PL237129B1 PL 237129 B1 PL237129 B1 PL 237129B1 PL 422501 A PL422501 A PL 422501A PL 42250117 A PL42250117 A PL 42250117A PL 237129 B1 PL237129 B1 PL 237129B1
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- 229960003399 estrone Drugs 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 claims abstract description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 241000188153 Isaria fumosorosea Species 0.000 claims abstract description 7
- 239000000758 substrate Substances 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000000605 extraction Methods 0.000 claims abstract description 3
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 8
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims description 7
- 230000009466 transformation Effects 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 2
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 claims 1
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 abstract description 2
- 108090000790 Enzymes Proteins 0.000 abstract description 2
- 230000009471 action Effects 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 244000005700 microbiome Species 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 229960005309 estradiol Drugs 0.000 description 5
- 229930182833 estradiol Natural products 0.000 description 5
- 239000000262 estrogen Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940011871 estrogen Drugs 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 230000004071 biological effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001076 estrogenic effect Effects 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 230000035800 maturation Effects 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 210000005132 reproductive cell Anatomy 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001836 utereotrophic effect Effects 0.000 description 2
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 229920013685 Estron Polymers 0.000 description 1
- 206010017076 Fracture Diseases 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
- 206010058359 Hypogonadism Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000001164 Osteoporotic Fractures Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000037182 bone density Effects 0.000 description 1
- 230000004097 bone metabolism Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000002657 hormone replacement therapy Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
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- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Zgłoszenie dotyczy 3-O-(ß-D-4'-O-metyloglukopiranozylo)-estron o wzorze 2 i sposób jej wytwarzania. Sposób polega na tym, że w wyniku działania układu enzymatycznego zawartego w komórkach szczepu Isaria fumosorosea KCh J2, następuje przyłączenie ß-D-4'-O-metyloglukopiranozy do grupy hydroksylowej substratu. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem, przez ekstrakcję rozpuszczalnikiem organicznym niemieszającym się z wodą (octan etylu).The application relates to 3-O-(ß-D-4'-O-methylglucopyranosyl)-estrone of formula 2 and a method for its preparation. The method consists in the fact that as a result of the action of the enzyme system contained in the cells of the Isaria fumosorosea KCh J2 strain, ß-D-4'-O-methylglucopyranose is attached to the hydroxyl group of the substrate. The product thus obtained is separated from the aqueous culture of the microorganism by a known method by extraction with a water-immiscible organic solvent (ethyl acetate).
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest nowy 3-O -(3-D-4’-O-metyloglukopiranozylo)-estron.The present invention relates to a novel 3-O - (3-D-4'-O-methylglucopyranosyl) oestrone.
Przedmiotem jest również sposób wytwarzania 3-O-(3-D-4’-O -metyloglukopiranozylo)-estronu.There is also provided a process for the production of 3-O- (3-D-4′-O-methylglucopyranosyl) -estrone.
Metoda, według wynalazku może znaleźć zastosowanie w przemyśle farmaceutycznym do wytwarzania leków regulujących prawidłowy rozwój i utrzymanie żeńskiego fenotypu oraz stymulujących rozwój komórek rozrodczych.The method according to the invention may find application in the pharmaceutical industry for the production of drugs that regulate the proper development and maintenance of the female phenotype and stimulate the development of reproductive cells.
Estrogeny są zaangażowane w rozwój i utrzymanie żeńskiego fenotypu, dojrzewanie komórek rozrodczych oraz prawidłowy rozwój ciąży. Są również ważne dla wielu innych, nie związanych z płciowością procesów, obejmujących wzrost, dojrzewanie układu nerwowego, metabolizmu kości oraz przebudowę i reakcje śródbłonka (Yasui T, Uemura H, Tezuka M, Yamada M, Irahara M, Miura M, et al. Biological effects of hormone replacement therapy in relation to serum estradiol levels. Horm Res 2001 ;56:38-44; Ettinger B, Pressman A, Sklarin P, Bauer DC, Cauley JA, Cummings SR. Association between low levels of serum estradiol, bone density, and fractures among elderly women: the study of osteoporotic fractures. J Clin Endocrinol Metab 1998; 83:2239-2243; Amin S, Zhang Y, Sawin CT, Evans SR, Hannan MT, Kiel DP, et al. Association of hypogonadism and estradiol levels with bone mineral density in elderly men from the Framingham Study. Ann Intern Med 2000;133:951-963.). U kobiet, estrogeny są głównie wytwarzane w jajnikach, a czasie ciąży również w łożysku. Małe ilości są produkowane przez gruczoły nadnerczy. Dwa główne biologicznie aktywne estrogeny u nieciężarnych kobiet to estron i estradiol. Związki te mogą w organizmach ssaków być przekształcane w siebie nawzajem przez dehydrogenazę 173-hydroksy steroidową. Estron w zależności od stosowanego oznaczenia przypisuje się 20-80% aktywności biologicznej estradiolu (Owens JW, Ashby J. Critical review and evaluation of the uterotrophic bioassay for the identification of possible estrogen agonists and antagonists: in support of the validation of the OECD uterotrophic protocols for the laboratory rodent. Organisation for Economic Co-operation and Development. Crit Rev Toxicol 2002,32: 445-520; Fang H, Tong W, Perkins R, Soto AM, Prechtl NV, Sheehan DM. Quantitative comparison of in vitro assays for estrogenic activities. Environ Health Perspect 2000;108:723-9; Le Guevel R, Pakdel F. Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. Hum Reprod 2001;16:1030-1036).Estrogens are involved in the development and maintenance of the female phenotype, the maturation of reproductive cells and the proper development of pregnancy. They are also important to many other non-sexuality-related processes including growth, nervous system maturation, bone metabolism, and endothelial remodeling and responses (Yasui T, Uemura H, Tezuka M, Yamada M, Irahara M, Miura M, et al. Biological effects of hormone replacement therapy in relation to serum estradiol levels. Horm Res 2001; 56: 38-44; Ettinger B, Pressman A, Sklarin P, Bauer DC, Cauley JA, Cummings SR. Association between low levels of serum estradiol, bone density , and fractures among elderly women: the study of osteoporotic fractures. J Clin Endocrinol Metab 1998; 83: 2239-2243; Amin S, Zhang Y, Sawin CT, Evans SR, Hannan MT, Kiel DP, et al. Association of hypogonadism and estradiol levels with bone mineral density in elderly men from the Framingham Study. Ann Intern Med 2000; 133: 951-963.). In women, oestrogens are mainly produced in the ovaries and also in the placenta during pregnancy. Small amounts are produced by the adrenal glands. The two main biologically active estrogens in non-pregnant women are estrone and estradiol. These compounds can be transformed into each other in mammals by 173-hydroxy steroid dehydrogenase. Estron, depending on the assay used, is assigned to 20-80% of the biological activity of estradiol (Owens JW, Ashby J. Critical review and evaluation of the uterotrophic bioassay for the identification of possible estrogen agonists and antagonists: in support of the validation of the OECD uterotrophic protocols for the laboratory rodent. Organization for Economic Co-operation and Development. Crit Rev Toxicol 2002, 32: 445-520; Fang H, Tong W, Perkins R, Soto AM, Prechtl NV, Sheehan DM. Quantitative comparison of in vitro assays for estrogenic activities. Environ Health Perspect 2000; 108: 723-9; Le Guevel R, Pakdel F. Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. Hum Reprod 2001; 16: 1030-1036).
Z opisu zgłoszenia wynalazku P-416996 znany jest szczep Isaria fumosorosea KCh J2.From the description of the application of the invention P-416996 the strain Isaria fumosorosea KCh J2 is known.
W literaturze nie ma doniesień dotyczących 3-O -(3-D-4’-O-metyloglukopiranozylo)-estronu.There are no reports in the literature on 3-O - (3-D-4'-O-methylglucopyranosyl) -estrone.
Wynalazek polega na tym, że wprowadzenie 3-D-4’-O -metyloglukopiranozy w cząsteczce estronu, prowadzi się w wodnej kulturze szczepu Isaria fumosorosea KCh J2.The invention is based on the fact that the introduction of 3-D-4'-O-methylglucopyranose in the estrone molecule is carried out in an aqueous culture of the strain Isaria fumosorosea KCh J2.
Istota wynalazku polega na tym, że do podłoża odpowiedniego dla grzybów strzępkowych wprowadza się szczep Isaria fumosorosea KCh J2. Po upływie co najmniej 48 godzin do hodowli wprowadza się substrat, którym jest estron o wzorze 1, rozpuszczony w rozpuszczalniku organicznym mieszającym się z wodą. Transformację prowadzi się w temperaturze od 20 do 30 stopni Celsjusza, przy ciągłym wstrząsaniu, co najmniej 24 godziny. Kolejno produkt ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą i oczyszcza chromatograficznie.The essence of the invention consists in introducing the Isaria fumosorosea KCh J2 strain into a medium suitable for filamentous fungi. After at least 48 hours, the substrate is introduced into the culture, which is an estrone of the formula I, dissolved in a water-miscible organic solvent. The transformation is carried out at a temperature of 20 to 30 degrees Celsius with continuous shaking for at least 24 hours. 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 0,2 g : 1 L.Preferably, the ratio of the mass of the added substrate to the culture volume is 0.2 g: 1 L.
Korzystnie także jest, gdy proces prowadzi się w temperaturze 25 stopni Celsjusza.It is also preferred that the process is carried out at a temperature of 25 degrees Celsius.
Korzystnie także jest, gdy transformację prowadzi się przez co najmniej 24 godziny, najlep iej przez 72 godziny.It is also preferred that the transformation is carried out for at least 24 hours, preferably 72 hours.
Dodatkowo, korzystnie jest, gdy rozpuszczalnikiem stosowanym do ekstrakcji jest octan etylu.Additionally, it is preferred that the extraction solvent is ethyl acetate.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w komórkach szczepu Isaria fumosorosea KCh J2, następuje przyłączenie 3-D-4’-O-metyloglukopiranozy do grupy hydroksylowej substratu.Following the invention, as a result of the action of the enzyme system contained in the cells of the strain Isaria fumosorosea KCh J2, the attachment of 3-D-4'-O-methylglucopyranose to the hydroxyl group of the substrate takes place.
Zasadniczą zaletą wynalazku jest otrzymanie 3-O-(3-D-4’-O-metyloglukopiranozylo)-estron, z wydajnością izolowaną na poziomie 40% (konwersja według NMR = 85%), w temperaturze pokojowej i przy pH naturalnym dla szczepu.The main advantage of the invention is the preparation of 3-O- (3-D-4'-O-methylglucopyranosyl) -estrone with an isolated yield of 40% (conversion according to NMR = 85%), at room temperature and pH natural for the strain.
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 5 g aminobaku i 15 g glukozy, wprowadza się szczep Isaria fumosorosea KCh J2. Po 72 godzinach jego wzrostu dodaje się 100 mg estronu o wzorze 1, rozpuszczonego w 1 cm3 DMSO. Transformację prowadzi się w 25 stopniach Celsjusza przy ciągłym wstrząsaniu przez 24 godziny. Następnie mieszaninę poreakcyjną ekstrahuje się trzykrotnie octanem etylu, osusza bezwodnymExample d. To the Erlenmeyer flask with a capacity of 2,000 cm 3, which is 500 cm 3 of a sterile medium containing 5 g aminobaku and 15 g of glucose, the strain is introduced Isaria fumosorosea SDS J2. After 72 hours of growth, 100 mg of estrone of formula 1, dissolved in 1 cm 3 of DMSO, are added. The transformation is carried out at 25 degrees Celsius with continuous shaking for 24 hours. The reaction mixture was then extracted three times with ethyl acetate, dried with anhydrous
PL 237 129 B1 siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymany ekstrakt oczyszcza się chromatograficznie, używając jako eluentu mieszaniny chloroform i metanol 9:1.With magnesium sulfate and evaporate the solvent. The extract obtained is purified by chromatography using a 9: 1 mixture of chloroform and methanol as eluent.
Na tej drodze otrzymuje się 40 mg 3-O-(β-ϋ-4’-O-metyloglukopiranozylo)estron, (konwersja według NMR = 85%).In this way, 40 mg of 3-O- (β-ϋ-4'-O-methylglucopyranosyl) estrone are obtained (conversion by NMR = 85%).
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
1H NMR (600MHz) (ppm) (DMSO) δ: 0.84 (s, 3H, 18-H); 1.30-1.42 (m, 3H, 11-Κβ, 12-Ha, 14-H); 1.45-1.53 (m, 2H, 7-Ha, 8-H); 1.56 (tt, 1H, J = 11.9, 9.0 Hz, 15-Ha); 1.74-1.77 (m, 1H, 12-Hβ); 1.901.98 (m, 2H, 7-Κβ, 15-Ha); 2.05 (dd, 1H, J = 18.8, 9.1 Hz, 16-Ha); 2.15-2.21 (m, 1H, 9-H); 2.31-2.37 (m, 1H, 11-Ha); 2.45 (dd, 1H, J = 19.0, 8.3 Hz, 16-Κβ); 2.79-2.87 (m, 2H, 6-Ha, 6-Κβ); 3.03 (t, 1H, J = 9.4 Hz, 4-H’); 3.22 (ddd, 1H, J = 8.6, 8.1, 5.2 Hz, 5-H’); 3.33 (ddd, 1H, J = 9.8, 4.9, 2.0 Hz, 2-H’); 3.36 (s, 3H, -OC H3); 3.40 (td, 1H, J = 9.0, 5.4 Hz, 3-H’); 3.50 (ddd, 1H, J = 11.6, 6.3, 5.2 Hz, one of 6-H’); 3.63 (ddd, 1H, J = 11.7, 4.8, 1.7 Hz, one of 6-H’); 4.68 (dd, 1H, J = 6.3, 5.1 Hz, C’6-O H); 4.81 (d, 1H, J = 7.8 Hz, 1 -H’); 5.23 (d, 1H, J = 5.4 Hz, C’3-O H); 5.33 (d, 1H, J = 5.3 Hz, C’2-O H); 6.73 (d, 1H, J = 2.6 Hz, 4-H); 6.80 (dd, 1H, J = 8.6, 2.6 Hz, 2-H); 7.18 (d, 1H, J = 8.6 Hz, 1-H). 1 H NMR (600MHz) (ppm) (DMSO) δ: 0.84 (s, 3H, 18-H); 1.30-1.42 (m, 3H, 11-Κβ, 12-Ha, 14-H); 1.45-1.53 (m, 2H, 7-Ha, 8-H); 1.56 (mp, 1H, J = 11.9, 9.0 Hz, 15-Ha); 1.74-1.77 (m, 1H, 12-Hβ); 1,901.98 (m, 2H, 7-Κβ, 15-Ha); 2.05 (dd, 1H, J = 18.8, 9.1 Hz, 16-Ha); 2.15-2.21 (m, 1H, 9-H); 2.31-2.37 (m, 1H, 11-Ha); 2.45 (dd, 1H, J = 19.0, 8.3 Hz, 16-Κβ); 2.79-2.87 (m, 2H, 6-Ha, 6-Κβ); 3.03 (t, 1H, J = 9.4 Hz, 4-H '); 3.22 (ddd, 1H, J = 8.6, 8.1, 5.2 Hz, 5-H '); 3.33 (ddd, 1H, J = 9.8, 4.9, 2.0 Hz, 2-H '); 3.36 (s, 3H, -OC H3); 3.40 (td, 1H, J = 9.0, 5.4 Hz, 3-H '); 3.50 (ddd, 1H, J = 11.6, 6.3, 5.2 Hz, one of 6-H '); 3.63 (ddd, 1H, J = 11.7, 4.8, 1.7 Hz, one of 6-H '); 4.68 (dd, 1H, J = 6.3, 5.1 Hz, C'6-OH); 4.81 (d, 1H, J = 7.8Hz, 1 -H '); 5.23 (d, 1H, J = 5.4Hz, C'3-OH); 5.33 (d, 1H, J = 5.3Hz, C'2-OH); 6.73 (d, 1H, J = 2.6 Hz, 4-H); 6.80 (dd, 1H, J = 8.6, 2.6 Hz, 2-H); 7.18 (d, 1H, J = 8.6 Hz, 1-H).
13C NMR (151MHz) (ppm) (DMSO) δ: 126,11 (C-1); 113,78 (C-2); 155,27 (C-3); 116,32 (C-4); 137,36 (C-5); 29,19 (C-6); 26,05 (C-7); 37,84 (C-8); 43,51 (C-9); 133,09 (C-10); 25,51 (C-11); 31,38 (C-12); 47,36 (C-13); 49,60 (C-14); 21,17 (C-15); 35,41 (C-16); 219,74 (C-17); 13,55 (C-18); 100,34 (C-1’); 73,49 (C-2’); 76,35 (C-3’); 79,08 (C-4’); 75,60 (C-5’); 60,31 (C-6’); 59,67 (-O C H3). 13 C NMR (151MHz) (ppm) (DMSO) δ: 126.11 (C-1); 113.78 (C-2); 155.27 (C-3); 116.32 (C-4); 137.36 (C-5); 29.19 (C-6); 26.05 (C-7); 37.84 (C-8); 43.51 (C-9); 133.09 (C-10); 25.51 (C-11); 31.38 (C-12); 47.36 (C-13); 49.60 (C-14); 21.17 (C-15); 35.41 (C-16); 219.74 (C-17); 13.55 (C-18); 100.34 (C-1 '); 73.49 (C-2 '); 76.35 (C-3 '); 79.08 (C-4 '); 75.60 (C-5 '); 60.31 (C-6 '); 59.67 (-OC H3).
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| DE2326084A1 (en) * | 1973-05-19 | 1974-12-05 | Schering Ag | Oestratriene 3-beta glucosides prepn - by adding 3-hydroxy steroid to a carbohydrate-contg. fungal culture medium |
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