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Preparative isolation of four new and two known flavonoids from the leaf of Patrinia villosa Juss. by counter-current chromatography and evaluation of their anticancer activities in vitro.
J Chromatogr A. 2006 May 19; 1115(1-2):103-11.JC

Abstract

A preparative counter-current chromatography (CCC) was used to isolate and separate chemical constituents from the leaf of Patrinia villosa, a famous traditional Chinese medicinal herb. Six flavonoids including two known and four novel compounds were successfully simultaneous purified by CCC with a two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (10: 13: 13: 10, v/v) by increasing the flow rate of the mobile phase from 1.0 ml/min to 2.0 ml/min after 110 min to bring out the late eluters. The separation produced total of 44.9 mg fraction I with 99.1% purity, 35.5 mg fraction II with 98.8% purity, 79.8 mg fraction III with 99.3% purity, 45.8 mg fraction IV with 98.8% purity, 39.8 mg fraction V with 98.6% purity and 9.6 mg fraction VI with 97.5% purity from 400 mg crude extract in one single isolation procedure and less than 10 h, and the obtained fractions were all analyzed by high performance liquid chromatography (HPLC). Their chemical structures were elucidated as (2S)-5,7,2',6'-tetrahydroxy-6,8-di (gamma,gamma-dimethylallyl) flavanone (1), (2S)-5,7,2',6'-tetrahydroxy-6-lavandulylated flavanone (2), (2S)-5,7,2',6'-tetrahydroxy-4'-lavandulylated flavanone (3), (2S)-5,2',6'-trihydroxy-2'',2''-dimethylpyrano [5'', 6'': 6, 7] flavanone (4), (2S, 3''S)-5,2',6'-trihydroxy-3''-gamma,gamma-dimethylallyl-2'',2''-dimethyl-3'',4''-dihydropyrano [5'', 6'': 6, 7] flavanone (5) and licoagrochalcone B (6), respectively, by spectrum methods including UV, IR, high resolution (HR)-electrospray ionization (ESI)-MS, 1-dimension (1D) and 2-dimension (2D) NMR techniques. Among them, compounds 2, 3, 4, and 5 were new compounds and discovered from nature for the first time. The recoveries of the six compounds were 91.2%, 91.4%, 92.1%, 90.5%, 90.3% and 89.7%, respectively, in CCC step. Subsequently, their anticancer activities were also examined to inhibit human cancer cells' growth including A549, BEL-7402, SGC-7901, MCF-7, HT-29, K562 and A498 cell lines by MTT method in vitro. The results indicated that the compounds 1, 2 and 3 exhibited high anticancer activities (IC50 < 7 microg/ml), especially to K562 cancer cell (IC50 < 3.1 microg/ml), and the compounds 4, 5 and 6 exhibited weaker inhibition effect (IC50 < 30 microg/ml).

Authors+Show Affiliations

Peng J
Shanghai Key Laboratory for Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University, No. 325 Guohe Road, Shanghai 200433, China.
Fan G
No affiliation info available
Wu Y
No affiliation info available

MeSH

Antineoplastic Agents, PhytogenicCountercurrent DistributionFlavonoidsHT29 CellsHumansK562 CellsPatriniaTumor Cells, Cultured

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16545824

Citation

Peng, Jinyong, et al. "Preparative Isolation of Four New and Two Known Flavonoids From the Leaf of Patrinia Villosa Juss. By Counter-current Chromatography and Evaluation of Their Anticancer Activities in Vitro." Journal of Chromatography. A, vol. 1115, no. 1-2, 2006, pp. 103-11.
Peng J, Fan G, Wu Y. Preparative isolation of four new and two known flavonoids from the leaf of Patrinia villosa Juss. by counter-current chromatography and evaluation of their anticancer activities in vitro. J Chromatogr A. 2006;1115(1-2):103-11.
Peng, J., Fan, G., & Wu, Y. (2006). Preparative isolation of four new and two known flavonoids from the leaf of Patrinia villosa Juss. by counter-current chromatography and evaluation of their anticancer activities in vitro. Journal of Chromatography. A, 1115(1-2), 103-11.
Peng J, Fan G, Wu Y. Preparative Isolation of Four New and Two Known Flavonoids From the Leaf of Patrinia Villosa Juss. By Counter-current Chromatography and Evaluation of Their Anticancer Activities in Vitro. J Chromatogr A. 2006 May 19;1115(1-2):103-11. PubMed PMID: 16545824.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Preparative isolation of four new and two known flavonoids from the leaf of Patrinia villosa Juss. by counter-current chromatography and evaluation of their anticancer activities in vitro. AU - Peng,Jinyong, AU - Fan,Guorong, AU - Wu,Yutian, Y1 - 2006/03/20/ PY - 2005/12/09/received PY - 2006/02/23/revised PY - 2006/02/24/accepted PY - 2006/3/21/pubmed PY - 2006/7/20/medline PY - 2006/3/21/entrez SP - 103 EP - 11 JF - Journal of chromatography. A JO - J Chromatogr A VL - 1115 IS - 1-2 N2 - A preparative counter-current chromatography (CCC) was used to isolate and separate chemical constituents from the leaf of Patrinia villosa, a famous traditional Chinese medicinal herb. Six flavonoids including two known and four novel compounds were successfully simultaneous purified by CCC with a two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (10: 13: 13: 10, v/v) by increasing the flow rate of the mobile phase from 1.0 ml/min to 2.0 ml/min after 110 min to bring out the late eluters. The separation produced total of 44.9 mg fraction I with 99.1% purity, 35.5 mg fraction II with 98.8% purity, 79.8 mg fraction III with 99.3% purity, 45.8 mg fraction IV with 98.8% purity, 39.8 mg fraction V with 98.6% purity and 9.6 mg fraction VI with 97.5% purity from 400 mg crude extract in one single isolation procedure and less than 10 h, and the obtained fractions were all analyzed by high performance liquid chromatography (HPLC). Their chemical structures were elucidated as (2S)-5,7,2',6'-tetrahydroxy-6,8-di (gamma,gamma-dimethylallyl) flavanone (1), (2S)-5,7,2',6'-tetrahydroxy-6-lavandulylated flavanone (2), (2S)-5,7,2',6'-tetrahydroxy-4'-lavandulylated flavanone (3), (2S)-5,2',6'-trihydroxy-2'',2''-dimethylpyrano [5'', 6'': 6, 7] flavanone (4), (2S, 3''S)-5,2',6'-trihydroxy-3''-gamma,gamma-dimethylallyl-2'',2''-dimethyl-3'',4''-dihydropyrano [5'', 6'': 6, 7] flavanone (5) and licoagrochalcone B (6), respectively, by spectrum methods including UV, IR, high resolution (HR)-electrospray ionization (ESI)-MS, 1-dimension (1D) and 2-dimension (2D) NMR techniques. Among them, compounds 2, 3, 4, and 5 were new compounds and discovered from nature for the first time. The recoveries of the six compounds were 91.2%, 91.4%, 92.1%, 90.5%, 90.3% and 89.7%, respectively, in CCC step. Subsequently, their anticancer activities were also examined to inhibit human cancer cells' growth including A549, BEL-7402, SGC-7901, MCF-7, HT-29, K562 and A498 cell lines by MTT method in vitro. The results indicated that the compounds 1, 2 and 3 exhibited high anticancer activities (IC50 < 7 microg/ml), especially to K562 cancer cell (IC50 < 3.1 microg/ml), and the compounds 4, 5 and 6 exhibited weaker inhibition effect (IC50 < 30 microg/ml). SN - 0021-9673 UR - https://www.unboundmedicine.com/medline/citation/16545824/Preparative_isolation_of_four_new_and_two_known_flavonoids_from_the_leaf_of_Patrinia_villosa_Juss__by_counter_current_chromatography_and_evaluation_of_their_anticancer_activities_in_vitro_ DB - PRIME DP - Unbound Medicine ER -