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Preparative isolation of six anti-tumour biflavonoids from Selaginella doederleinii Hieron by high-speed counter-current chromatography.
Phytochem Anal 2014 Mar-Apr; 25(2):127-33PA

Abstract

INTRODUCTION

Biflavonoids are the primary constituents of Selaginella doederleinii Hieron, to which different bioactivities have been attributed, including anti-cancer, anti-inflammatory, anti-oxidant, anti-fungal and anti-virus activity. However, effective methods for separation of these compounds are not currently available.

OBJECTIVE

To develop a high performance and bioassay-guided method for preparative isolation of biflavonoids from S. doederleini via high-speed counter-current chromatography (HSCCC).

METHODS

The anti-proliferation effects of four fractions (70% ethanol, petroleum ether, dichloromethane and acetic ether extracts) of S. doederleinii on five human cancer cells were monitored. The dichloromethane and acetic ether extracts showed good cytotoxicities to the studied cancer cell lines, guiding the subsequent separation. Two solvent systems composed of n-hexane:ethyl acetate:methanol:water (1:2:1.5:1.5, v/v) and n-hexane:ethyl acetate:methanol:water (3:2:3:2, v/v) were developed for separation of the active fractions, respectively. Identification of the biflavonoids was performed by EI-MS(n) , (1) H- and (13) C-NMR.'

RESULTS

Under the optimised conditions, 12.6 mg amentoflavone (91.4%), 6.6 mg robustaflavone (90.4%), 7.5 mg 2'', 3''-dihydro-3', 3'''-biapigenin (98.2%) and 7.3 mg 3', 3'''-binaringenin (90.3%) from acetic ether extract (500 mg) and 6.3 mg heveaflavone (93.5%) and 5.3 mg 7, 4', 7'', 4'''-tetra-O-methyl-amentoflavone (94.5%) from dichloromethane extract (200 mg) were obtained, respectively. The anti-proliferation effects of the six biflavonoids on the five human cancer cells were further verified.

CONCLUSION

The study provides methodological references for simultaneously preparative isolation of several bioactive biflavones from the herbal family of Selaginella. It is the first report discovering 2'', 3''-dihydro-3', 3'''-biapigenin and 3', 3'''-binaringenin from this herb and describing their cytotoxicities to human cancer cell lines.

Authors+Show Affiliations

Department of Pharmaceutical Analysis, Faculty of Pharmacy, Fujian Medical University, Fuzhou, 350004, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

24115163

Citation

Li, Shaoguang, et al. "Preparative Isolation of Six Anti-tumour Biflavonoids From Selaginella Doederleinii Hieron By High-speed Counter-current Chromatography." Phytochemical Analysis : PCA, vol. 25, no. 2, 2014, pp. 127-33.
Li S, Zhao M, Li Y, et al. Preparative isolation of six anti-tumour biflavonoids from Selaginella doederleinii Hieron by high-speed counter-current chromatography. Phytochem Anal. 2014;25(2):127-33.
Li, S., Zhao, M., Li, Y., Sui, Y., Yao, H., Huang, L., & Lin, X. (2014). Preparative isolation of six anti-tumour biflavonoids from Selaginella doederleinii Hieron by high-speed counter-current chromatography. Phytochemical Analysis : PCA, 25(2), pp. 127-33. doi:10.1002/pca.2478.
Li S, et al. Preparative Isolation of Six Anti-tumour Biflavonoids From Selaginella Doederleinii Hieron By High-speed Counter-current Chromatography. Phytochem Anal. 2014;25(2):127-33. PubMed PMID: 24115163.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Preparative isolation of six anti-tumour biflavonoids from Selaginella doederleinii Hieron by high-speed counter-current chromatography. AU - Li,Shaoguang, AU - Zhao,Meifeng, AU - Li,Yuxiang, AU - Sui,Yuxia, AU - Yao,Hong, AU - Huang,Liying, AU - Lin,Xinhua, Y1 - 2013/09/23/ PY - 2013/06/07/received PY - 2013/08/11/revised PY - 2013/08/20/accepted PY - 2013/10/12/entrez PY - 2013/10/12/pubmed PY - 2014/9/16/medline KW - Activity-guided preparative isolation KW - HSCCC KW - Selaginella doederleinii Hieron KW - biflavonoids KW - cytotoxicity SP - 127 EP - 33 JF - Phytochemical analysis : PCA JO - Phytochem Anal VL - 25 IS - 2 N2 - INTRODUCTION: Biflavonoids are the primary constituents of Selaginella doederleinii Hieron, to which different bioactivities have been attributed, including anti-cancer, anti-inflammatory, anti-oxidant, anti-fungal and anti-virus activity. However, effective methods for separation of these compounds are not currently available. OBJECTIVE: To develop a high performance and bioassay-guided method for preparative isolation of biflavonoids from S. doederleini via high-speed counter-current chromatography (HSCCC). METHODS: The anti-proliferation effects of four fractions (70% ethanol, petroleum ether, dichloromethane and acetic ether extracts) of S. doederleinii on five human cancer cells were monitored. The dichloromethane and acetic ether extracts showed good cytotoxicities to the studied cancer cell lines, guiding the subsequent separation. Two solvent systems composed of n-hexane:ethyl acetate:methanol:water (1:2:1.5:1.5, v/v) and n-hexane:ethyl acetate:methanol:water (3:2:3:2, v/v) were developed for separation of the active fractions, respectively. Identification of the biflavonoids was performed by EI-MS(n) , (1) H- and (13) C-NMR.' RESULTS: Under the optimised conditions, 12.6 mg amentoflavone (91.4%), 6.6 mg robustaflavone (90.4%), 7.5 mg 2'', 3''-dihydro-3', 3'''-biapigenin (98.2%) and 7.3 mg 3', 3'''-binaringenin (90.3%) from acetic ether extract (500 mg) and 6.3 mg heveaflavone (93.5%) and 5.3 mg 7, 4', 7'', 4'''-tetra-O-methyl-amentoflavone (94.5%) from dichloromethane extract (200 mg) were obtained, respectively. The anti-proliferation effects of the six biflavonoids on the five human cancer cells were further verified. CONCLUSION: The study provides methodological references for simultaneously preparative isolation of several bioactive biflavones from the herbal family of Selaginella. It is the first report discovering 2'', 3''-dihydro-3', 3'''-biapigenin and 3', 3'''-binaringenin from this herb and describing their cytotoxicities to human cancer cell lines. SN - 1099-1565 UR - https://www.unboundmedicine.com/medline/citation/24115163/Preparative_isolation_of_six_anti_tumour_biflavonoids_from_Selaginella_doederleinii_Hieron_by_high_speed_counter_current_chromatography_ L2 - https://doi.org/10.1002/pca.2478 DB - PRIME DP - Unbound Medicine ER -