RU99113031A - EPOTILONS C, D, E AND F, THEIR RECEIVING AND MEANS ON THEIR BASIS - Google Patents

EPOTILONS C, D, E AND F, THEIR RECEIVING AND MEANS ON THEIR BASIS

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Publication number
RU99113031A
RU99113031A RU99113031/04A RU99113031A RU99113031A RU 99113031 A RU99113031 A RU 99113031A RU 99113031/04 A RU99113031/04 A RU 99113031/04A RU 99113031 A RU99113031 A RU 99113031A RU 99113031 A RU99113031 A RU 99113031A
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epothilone
biotransformant
culture
representing
fact
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RU99113031/04A
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Russian (ru)
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RU2198173C2 (en
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Ханс РАЙХЕНБАХ
Герхард ХЕФЛЕ
Клаус ГЕРТ
Хайнрих ШТАЙНМЕТЦ
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Гезелльшафт Фюр Биотехнологише Форшунг Мбх (Гбф)
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Claims (19)

1. Эпотилон общей формулы
Figure 00000001

где R = Н, СН3.1. Epothilone General formula
Figure 00000001

where R = H, CH 3 . 2. Эпотилон по п. 1, представляющий собой эпотилон С при R = Н. 2. Epothilone according to claim 1, representing epothilone C with R = N. 3. Эпотилон по п. 1, представляющий собой эпотилон D при R = СН3.3. Epothilone according to claim 1, representing epothilone D with R = CH 3 . 4. Эпотилон по п. 2, суммарной формулы C26H39NO5S, отличающийся 1H- и 13С-ЯМР-спектрами согласно таблице 1.4. Epothilone according to claim 2, the total formula C 26 H 39 NO 5 S, characterized by 1 H- and 13 C-NMR spectra according to table 1. 5. Эпотилон по п. 3, суммарной формулы C27H41N05S, отличающийся Н- и 13С-ЯМР-спектрами согласно таблице 1.5. Epothilone according to claim 3, the total formula C 27 H 41 N0 5 S, different H- and 13 C-NMR spectra according to table 1. 6. Эпотилон общей формулы
Figure 00000002

где R = Н, СН3.6. Epothilone of General Formula
Figure 00000002

where R = H, CH 3 . 7. Эпотилон по п. 6, представляющий собой эпотилон Е при R = Н. 7. Epothilone under item 6, representing epothilone E with R = N. 8. Эпотилон по п. 6, представляющий собой эпотилон F при R = СН3.8. The epothilone according to claim 6, representing epothilone F with R = CH 3 . 9. Эпотилон по п. 7 суммарной формулы С26Н39N07S, отличающийся следующим 1Н-ЯМР-спектром (300 МГц, CDCl3) : δ = 2.38 (2-Нa), 2.51 (2-Нb), 4.17 (3-Н), 3.19 (6-Н), 3.74 (7-Н), 1.30-1.70 (8-Н, 9-Н2, 10-Н2, 11-H2), 2.89 (12-Н), 3.00 (13-Н), 1.88 (14-Нa), 2.07 (14-Нb), 5.40 (15-Н), 6.57 (17-Н), 7.08 (19-Н), 4.85 (21-H2), 1.05 (22-Н3), 1.32 (23-Н3), 1.17 (24-Н3), 0.97 (25-Н3), 2.04 (27-Н3).9. Epothilone according to claim 7 of the general formula C 26 H 39 N0 7 S, characterized by the following 1 H-NMR spectrum (300 MHz, CDCl 3 ): δ = 2.38 (2-H a ), 2.51 (2-H b ) , 4.17 (3-Н), 3.19 (6-Н), 3.74 (7-Н), 1.30-1.70 (8-Н, 9-Н 2 , 10-Н 2 , 11-Н 2 ), 2.89 (12- H), 3.00 (13-H), 1.88 (14-H a ), 2.07 (14-H b ), 5.40 (15-H), 6.57 (17-H), 7.08 (19-H), 4.85 (21 -H 2 ), 1.05 (22-H 3 ), 1.32 (23-H 3 ), 1.17 (24-H 3 ), 0.97 (25-H 3 ), 2.04 (27-H 3 ). 10. Эпотилон по п. 8 суммарной формулы C27H41NO7S, отличающийся следующим 1H-ЯМР-спектром (300 МГц, СDС13) : δ = 2.37 (2-Нa), 2.54 (2-Нb), 4.20 (3-Н), 3.27 (6-Н), 3.74 (7-Н), 1.30-1.70 (8-Н, 9-Н2, 10-H2, 11-Н2), 2.78 (13-Н), 1.91 (14-Н), 2.06 (14-Нb), 5.42 (15-Н), 6.58 (17-Н), 7.10 (19-Н), 4.89 (21-Н2), 1.05 (22-Н3), 1.26 (23-Н3), 1.14 (24-Н3), 0.98 (25-Н3), 1.35 (26-Н3), 2.06 (27-Н3).10. Epothilone according to claim 8 of the total formula C 27 H 41 NO 7 S, characterized by the following 1 H-NMR spectrum (300 MHz, CDCl 3 ): δ = 2.37 (2-H a ), 2.54 (2-H b ) , 4.20 (3-H), 3.27 (6-H), 3.74 (7-H), 1.30-1.70 (8 H, 9-H 2, 10-H 2, 11-H 2), 2.78 (13- H), 1.91 (14-H), 2.06 (14-H b ), 5.42 (15-H), 6.58 (17-H), 7.10 (19-H), 4.89 (21-H 2 ), 1.05 (22 -H 3 ), 1.26 (23-H 3 ), 1.14 (24-H 3 ), 0.98 (25-H 3 ), 1.35 (26-H 3 ), 2.06 (27-H 3 ). 11. Биотрансформант эпотилонов, полученный
а) культивированием микроорганизма Sorangium cellulosum DSM 6773 в присутствии адсорбирующей смолы известным образом, отделением культуры от адсорбирующей смолы и, в случае необходимости, добавлением ко всему количеству или к части отделенной культуры метанольного раствора исходного эпотилона,
б) инкубированием культуры с добавленным эпотилоном с последующим добавлением адсорбирующей смолы,
в) отделением адсорбирующей смолы от культуры элюированием метанолом и концентрированием элюата до получения сырого экстракта,
г) разделением сырого экстракта этилацетатом и водой, отделением этилацетатной фазы с последующим ее концентрированием до получения масла,
д) хроматографией масла на обращенной фазе при следующих условиях:
материал колонки - Нуклеосил 100 С-18, 7 мкм
размеры колонки - 250 х 4 мм
растворитель - метанол/вода = 60 : 40
скорость протекания растворителя - 1,2 мл/мин
с последующим отделением содержащих биотрансформант фракций, детектируемых гашением флуоресценции при 254 нм, и выделением биотрансформанта.11. Biotransformant epothilones obtained
a) cultivating the microorganism Sorangium cellulosum DSM 6773 in the presence of an adsorbing resin in a known manner, separating the culture from the adsorbing resin and, if necessary, adding to the whole or part of the separated culture a methanol solution of the starting epothilone,
b) incubating the culture with added epothilone followed by the addition of an adsorbent resin,
c) separating the adsorption resin from the culture by elution with methanol and concentrating the eluate to obtain a crude extract,
g) separation of the crude extract with ethyl acetate and water, separating the ethyl acetate phase, followed by concentration to an oil,
e) reverse phase oil chromatography under the following conditions:
column material - Nucleosil 100 C-18, 7 microns
column dimensions - 250 x 4 mm
solvent - methanol / water = 60: 40
solvent flow rate 1.2 ml / min
with the subsequent separation of fractions containing biotransformant, detected by quenching of fluorescence at 254 nm, and release of biotransformant. 12. Биотрансформант по п.11, полученный с использованием в качестве исходного эпотилона эпотилона А. 12. Biotransformant according to claim 11, obtained using epothilone A. as starting epothilone. 13. Биотрансформант по п.11, полученный с использованием в качестве исходного эпотилона эпотилона В. 13. Biotransformant according to claim 11, obtained using epothilone B. as the starting epothilone. 14. Биотрансформант по п.12, полученный тем, что на стадии д) отделяются фракции со значением Rt, равным 5,0 мин.14. Biotransformant according to item 12, obtained by the fact that at the stage d) fractions are separated with an R t value of 5.0 minutes. 15. Биотрансформант по п.13, полученный тем, что на стадии д) отделяются фракции со значением Rt, равным 5,4 мин.15. Biotransformant according to item 13, obtained by the fact that at the stage d) fractions are separated with an R t value of 5.4 minutes. 16. Биотрансформант по п.9 или 10, полученный тем, что на стадии (а) отделяется культура в возрасте 3 - 4 или более суток. 16. Biotransformant according to claim 9 or 10, obtained by the fact that at stage (a) a culture is separated at the age of 3-4 days or more. 17. Биотрансформант по пп.9 - 15, полученный тем, что на стадии (б) осуществляется инкубирование в течение 1 - 2 или более суток. 17. Biotransformant for PP.9 - 15, obtained by the fact that at the stage (b) is incubated for 1 to 2 or more days. 18. Средство для защиты растений в сельском и лесном хозяйстве и/или в садоводстве, состоящее из одного или более соединений по одному из предыдущих пунктов или одного или нескольких из этих соединений наряду с одним или несколькими обычными носителями и/или разбавителями. 18. Plant protection product in agriculture and forestry and / or gardening, consisting of one or more compounds in one of the preceding paragraphs or one or more of these compounds, along with one or more conventional carriers and / or diluents. 19. Терапевтическое средство, в частности, для использования в качестве цитостатического средства, состоящее из одного или более соединений по одному или нескольким из предыдущих пунктов или из одного или более соединений по одному или нескольким из предыдущих пунктов наряду с одним или несколькими обычными носителями и/или разбавителями. 19. A therapeutic agent, in particular, for use as a cytostatic agent, consisting of one or more compounds according to one or more of the preceding paragraphs or one or more compounds of one or more of the preceding paragraphs along with one or more conventional carriers and / or thinners.
RU99113031/04A 1996-11-18 1997-11-18 Epotylones c, d, e and f, their synthesis and agents based on thereof RU2198173C2 (en)

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DE19647580.5 1996-11-18
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