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Fraction B was recrystallized with acetone to give compound -Epicatchin (15, 13 mg).
The resulting solution was distilled in vacuo to give compound 3 as a pale yellow solid.
The organic layer was evaporated to give compound 10 (57% yield).
The sub-fraction EA was subjected to further column chromatography over silica gel eluting with n-hexane- EtOAc (3.5 6.5) as eluent to give compound 1 (11 mg), and n-hexane- EtOAc (4 6) to give compound 2 (7.8 mg).
The resulting solid was collected by filtration, washed with water and recrystallized from ethanol to give compound 6a d.
Fraction B1 was purified by preparative TLC (CHCl3 MeOH, 20 1) to give compound 3 (8 mg).
Fractions containing the product were combined and lyophilized to give compound 3 as white powder (2.3 mg, 0.0024 mmol, 72%).
F3 (98.4 mg) was subjected to semi-prep HPLC with isocratic elution (MeCN/H2O 90:10, 3 mL/min) to give compound 3 (0.8 mg).
Fraction E-4-6 (40 mg) was separated by semi-preparative HPLC (solvent system: 25% acetonitrile and 35% MeOH, respectively) to give compound (6) (4 mg).
After repeatedly purified by silica gel CC (CHCl3 acetone) and Sephadex LH-20 (CHCl3–MeOH, 1 1), II-c give compound clavolonine (11 mg).
Fraction C4 (515 mg) was purified by a semi-preparative HPLC (55 % CH3CN in H2O, 3 mL/min) to give compound 4 (15 mg).
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