baohuoside I synthesis
- Product Name:baohuoside I
- CAS Number:113558-15-9
- Molecular formula:C27 H30 O10
- Molecular Weight:514.52
489-32-7
113558-15-9
The general procedure for the synthesis of 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-benzopyran-4-one from Icariin was performed as follows: firstly, mycelia from agar slants ( 2 cm2) of C. blakesleeana mycelium was transferred to 100 mL of medium and incubated at 30 °C and 175 rpm for 36 h to prepare the inoculum. Subsequently, 10 mL of inoculum was added to 1000 mL of liquid medium and the flasks were placed on a rotary shaker and pre-cultured for 36 h at 175 rpm, 30°C. After completion of the pre-culture, 100 mg of Icariin was dissolved in 2 mL of methanol and added to 2 L of medium for preparative biotransformation to reach a final concentration of 50 mg/L. After continuing the culture for 5 days, the culture was filtered, and the filtrate was extracted five times with equal volumes of EtOAc. At the same time, suspension cells of C. blakesleeana (5.2 g) were extracted using 1000 mL EtOAc. All EtOAc extracts were combined and concentrated under reduced pressure. The resulting residue (1.6 g) was upsampled onto an ODS column (200 g, 10 cm × 50 cm) and eluted with MeOH-H?O (10% to 90% gradient, flow rate 2.0 mL/min). Finally, 90.1 mg of icariside II was obtained from the 60% MeOH-eluted grade (500 mL) with a purity of 96.5%.
489-32-7
609 suppliers
$7.00/25mg
113558-15-9
234 suppliers
$6.00/1mg
Yield:113558-15-9 95.1%
Reaction Conditions:
with Cunninghamella blakesleana in methanol for 120 h;Microbiological reaction;regioselective reaction;
Steps:
2.3 Culture and biotransformation procedures
Mycelia of C. blakesleeana from agar slants (2cm2) were transferred to 100mL of medium and cultured at 30°C with 175rpm for 36h to make a stock inoculum. Then 10mL volume of the inoculum was added to 1000mL of liquid medium, and the flask was placed on rotary shaker operating at 175rpm and 30°C. After 36h of preculture, 100mg of icariin with 2mL methanol added into 2L of culture medium for preparative biotransformation with the final concentration of 50mg/L. The incubation was continued for 5 additional days. The culture was filtered, and the filtrate was extracted with same volume of EtOAc for five times. And the suspension cells of C. blakesleeana (5.2g) were also extracted by using EtOAc (1000mL). Then all extraction of EtOAc were collected and concentrated under the reduced pressure. The residues (1.6g) were applied to an ODS column (200g, 10cm×50cm) and eluted with MeOH-H2O (in a gradient manner from 10% to 90%, at a flow rate of 2.0mL/min). Totally, 90.1mg of icariside II (96.5% purity) was obtained from fraction of 60% MeOH (500mL).
References:
Xin, XiuLan;Fan, Guang-Jun;Sun, Zheng;Zhang, Ning;Li, Ye;Lan, Rong;Chen, Liang;Dong, PeiPei [Journal of Molecular Catalysis B: Enzymatic,2015,vol. 122,p. 141 - 146]
518-82-1
528 suppliers
$25.00/25mg
489-32-7
609 suppliers
$7.00/25mg
23313-21-5
172 suppliers
$49.00/5mg
113558-15-9
234 suppliers
$6.00/1mg