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Isolation and characterization of antioxidant phenolic compounds from the aerial parts of Hypericum hyssopifolium L. by activity-guided fractionation.
J Ethnopharmacol. 2003 Jul; 87(1):73-83.JE

Abstract

Dried methanol extract of Hypericum hyssopifolium subsp. elongatum var. elongatum was dissolved in distilled water, and then fractioned by re-extracting with petroleum ether, chloroform, and ethyl acetate, subsequently. Antioxidant and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activities of these fractions were determined, in vitro. The amounts of total phenolic compounds were also determined. None of these fractions showed antioxidant activity, in contrast water and ethyl acetate fractions acted as prooxidant. However, the ethyl acetate fraction exhibited the highest DPPH radical-scavenging activity and the amount of its total phenolic compound was highest, too. Therefore, ethyl acetate fraction was subjected to further separation by chromatographic methods. Thus, five flavonoids (I3,II8-biapigenin, quercetin, quercetin-3-O-alpha-L-arabinofuranoside, quercetin-3-O-beta-D-galactopyranoside, quercetin-3-O-beta-D-galactopyranoside-7-O-beta-D-glucopyranoside) and a napthodianthrone (hypericin) were isolated, and their structures were determined by UV, IR, NMR, and MS spectroscopic methods. All isolated compounds showed antioxidant and DPPH radical-scavenging activities. Although, I3,II8-biapigenin and hypericin were able to show highest antioxidant activity, they had the lowest DPPH radical-scavenging activities. From these results, it can be suggested that these compounds may be used as potential antioxidants. In addition, the petroleum ether fraction was subjected to silica gel column chromatography (CC). Then, n-dotriacontanyl hexadecanoate, bis(2-methylheptyl) phthalate, and beta-sitosterol were isolated from it. It is of interest to present the spectral data of bis(2-methylheptyl) phthalate first time in the present study.

Authors+Show Affiliations

Atatürk Universitesi, Kazim Karabekir Eğitim Fakültesi, Kimya Eğitimi Anabilim Dali, 25240 Erzurum, Turkey.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

12787957

Citation

Cakir, Ahmet, et al. "Isolation and Characterization of Antioxidant Phenolic Compounds From the Aerial Parts of Hypericum Hyssopifolium L. By Activity-guided Fractionation." Journal of Ethnopharmacology, vol. 87, no. 1, 2003, pp. 73-83.
Cakir A, Mavi A, Yildirim A, et al. Isolation and characterization of antioxidant phenolic compounds from the aerial parts of Hypericum hyssopifolium L. by activity-guided fractionation. J Ethnopharmacol. 2003;87(1):73-83.
Cakir, A., Mavi, A., Yildirim, A., Duru, M. E., Harmandar, M., & Kazaz, C. (2003). Isolation and characterization of antioxidant phenolic compounds from the aerial parts of Hypericum hyssopifolium L. by activity-guided fractionation. Journal of Ethnopharmacology, 87(1), 73-83.
Cakir A, et al. Isolation and Characterization of Antioxidant Phenolic Compounds From the Aerial Parts of Hypericum Hyssopifolium L. By Activity-guided Fractionation. J Ethnopharmacol. 2003;87(1):73-83. PubMed PMID: 12787957.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isolation and characterization of antioxidant phenolic compounds from the aerial parts of Hypericum hyssopifolium L. by activity-guided fractionation. AU - Cakir,Ahmet, AU - Mavi,Ahmet, AU - Yildirim,Ali, AU - Duru,Mehmet Emin, AU - Harmandar,Mansur, AU - Kazaz,Cavit, PY - 2003/6/6/pubmed PY - 2003/11/13/medline PY - 2003/6/6/entrez SP - 73 EP - 83 JF - Journal of ethnopharmacology JO - J Ethnopharmacol VL - 87 IS - 1 N2 - Dried methanol extract of Hypericum hyssopifolium subsp. elongatum var. elongatum was dissolved in distilled water, and then fractioned by re-extracting with petroleum ether, chloroform, and ethyl acetate, subsequently. Antioxidant and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activities of these fractions were determined, in vitro. The amounts of total phenolic compounds were also determined. None of these fractions showed antioxidant activity, in contrast water and ethyl acetate fractions acted as prooxidant. However, the ethyl acetate fraction exhibited the highest DPPH radical-scavenging activity and the amount of its total phenolic compound was highest, too. Therefore, ethyl acetate fraction was subjected to further separation by chromatographic methods. Thus, five flavonoids (I3,II8-biapigenin, quercetin, quercetin-3-O-alpha-L-arabinofuranoside, quercetin-3-O-beta-D-galactopyranoside, quercetin-3-O-beta-D-galactopyranoside-7-O-beta-D-glucopyranoside) and a napthodianthrone (hypericin) were isolated, and their structures were determined by UV, IR, NMR, and MS spectroscopic methods. All isolated compounds showed antioxidant and DPPH radical-scavenging activities. Although, I3,II8-biapigenin and hypericin were able to show highest antioxidant activity, they had the lowest DPPH radical-scavenging activities. From these results, it can be suggested that these compounds may be used as potential antioxidants. In addition, the petroleum ether fraction was subjected to silica gel column chromatography (CC). Then, n-dotriacontanyl hexadecanoate, bis(2-methylheptyl) phthalate, and beta-sitosterol were isolated from it. It is of interest to present the spectral data of bis(2-methylheptyl) phthalate first time in the present study. SN - 0378-8741 UR - https://www.unboundmedicine.com/medline/citation/12787957/Isolation_and_characterization_of_antioxidant_phenolic_compounds_from_the_aerial_parts_of_Hypericum_hyssopifolium_L__by_activity_guided_fractionation_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0378874103001120 DB - PRIME DP - Unbound Medicine ER -