baohuoside I

Chemical Properties

Yellow needle-shaped crystals, soluble in methanol, derived from the whole herb of Epimedium.

Uses

Baohuoside I is an inhibitor of cell growth and also is a down-regulator of durvivin and cyclin D1 expression. Used in the treatment of esophageal cancer. Anti-cancer agent.

Definition

ChEBI: A glycosyloxyflavone that is 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone in which the hydroxy group at position 3 has been converted to its alpha-L-rhamnopyranoside.

Biological Activity

Icariside II (Baohuoside-I) is a flavonoid with cytoprotective, neuroprotective, antiproliferative, and erectile function properties.

Synthesis

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-HO (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%.

References

[1] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 122, p. 141 - 146
[2] Patent: CN104530127, 2016, B. Location in patent: Paragraph 0156-0159
[3] Patent: CN104387430, 2017, B. Location in patent: Paragraph 0109; 0110; 0111; 0112
[4] Journal of Natural Products, 2008, vol. 71, # 9, p. 1513 - 1517
[5] Journal of Asian Natural Products Research, 2015, vol. 17, # 6, p. 656 - 661