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Hydroxybenzoic Acids Are Significant Contributors to the Antioxidant Effect of Borututu Bark, Cochlospermum angolensis Welw. ex Oliv.

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ABSTRACT

1234514: Borututu (Cochlospermum angolensis) is an African tree whose bark has recently emerged as a herbal dietary supplement with claims for antioxidant activity. In order to substantiate the claimed activity of borututu supplements, we performed an activity-guided fractionation of the total extract utilizing a 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging assay. Subsequent flash and centrifugal chromatography resulted in the isolation of gallic acid () and protocatechuic acid () as the main antioxidant constituents. Two apocarotenoids and one flavonoid were also isolated from the chloroform fraction and were identified as cochloxanthin (), dihydrocochloxanthin (), and 7,4′-dimethyltaxifolin (), respectively. A High-performance liquid chromatography (HPLC) method was also developed for fingerprinting borututu samples, with Compounds – suggested as chemical markers for quality control purposes.

No MeSH data available.


Related in: MedlinePlus

Qualitative HPLC analysis of borututu bark. (A) Fingerprint of total methanolic extract (TME) and successive solvent fractions: chloroform (CF), ethyl acetate (EF), and methanol (MF; pseudomolecular ions [M−H]− of ellagic acids marked on peaks). (B) Pure compounds isolated from CF and EF: gallic acid (1), protocatechuic acid (2), cochloxanthin (3), dihydrocochloxanthin (4), and 7,4′-dimethyltaxifolin (5).
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antioxidants-06-00009-f005: Qualitative HPLC analysis of borututu bark. (A) Fingerprint of total methanolic extract (TME) and successive solvent fractions: chloroform (CF), ethyl acetate (EF), and methanol (MF; pseudomolecular ions [M−H]− of ellagic acids marked on peaks). (B) Pure compounds isolated from CF and EF: gallic acid (1), protocatechuic acid (2), cochloxanthin (3), dihydrocochloxanthin (4), and 7,4′-dimethyltaxifolin (5).

Mentions: HPLC fingerprinting was initially performed on borututu TME in order to identify different phytochemical markers that may be used to characterize the extract and to guide the subsequent isolation of these markers. Each solvent fraction of the total extract (CF, EF, and MF) contained one or more of the markers identified in TME. Figure 5A shows the fingerprint of the total extract and the chromatographic profiles of active subfractions with major markers identified in each. Fraction CF contained 3, 4, and 5 (retention times: 21.1, 22.3, and 13.6 min, respectively). Fraction EF showed 1 and 2 as its major constituents (retention times: 3.5 and 5.3 min, respectively). Fraction MF showed a cluster of peaks eluting between 7.5 and 11.5 min that were not isolated as pure compounds. However, these peaks showed the pseudomolecular ions [M−H]− 301, 315, 433, 447, 461, and 477 corresponding to ellagic acid and its glycosides and/or methyl analogs reported by Ferreres and co-workers [5]. The hexane fraction, on the other hand, did not possess any antioxidant activity and did not contain any significant UV-active markers. The same HPLC method was subsequently utilized to further confirm the purity of isolated compounds and to demonstrate their potential use as quality markers for borututu products (Figure 5B).


Hydroxybenzoic Acids Are Significant Contributors to the Antioxidant Effect of Borututu Bark, Cochlospermum angolensis Welw. ex Oliv.
Qualitative HPLC analysis of borututu bark. (A) Fingerprint of total methanolic extract (TME) and successive solvent fractions: chloroform (CF), ethyl acetate (EF), and methanol (MF; pseudomolecular ions [M−H]− of ellagic acids marked on peaks). (B) Pure compounds isolated from CF and EF: gallic acid (1), protocatechuic acid (2), cochloxanthin (3), dihydrocochloxanthin (4), and 7,4′-dimethyltaxifolin (5).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5384172&req=5

antioxidants-06-00009-f005: Qualitative HPLC analysis of borututu bark. (A) Fingerprint of total methanolic extract (TME) and successive solvent fractions: chloroform (CF), ethyl acetate (EF), and methanol (MF; pseudomolecular ions [M−H]− of ellagic acids marked on peaks). (B) Pure compounds isolated from CF and EF: gallic acid (1), protocatechuic acid (2), cochloxanthin (3), dihydrocochloxanthin (4), and 7,4′-dimethyltaxifolin (5).
Mentions: HPLC fingerprinting was initially performed on borututu TME in order to identify different phytochemical markers that may be used to characterize the extract and to guide the subsequent isolation of these markers. Each solvent fraction of the total extract (CF, EF, and MF) contained one or more of the markers identified in TME. Figure 5A shows the fingerprint of the total extract and the chromatographic profiles of active subfractions with major markers identified in each. Fraction CF contained 3, 4, and 5 (retention times: 21.1, 22.3, and 13.6 min, respectively). Fraction EF showed 1 and 2 as its major constituents (retention times: 3.5 and 5.3 min, respectively). Fraction MF showed a cluster of peaks eluting between 7.5 and 11.5 min that were not isolated as pure compounds. However, these peaks showed the pseudomolecular ions [M−H]− 301, 315, 433, 447, 461, and 477 corresponding to ellagic acid and its glycosides and/or methyl analogs reported by Ferreres and co-workers [5]. The hexane fraction, on the other hand, did not possess any antioxidant activity and did not contain any significant UV-active markers. The same HPLC method was subsequently utilized to further confirm the purity of isolated compounds and to demonstrate their potential use as quality markers for borututu products (Figure 5B).

View Article: PubMed Central - PubMed

ABSTRACT

1234514: Borututu (Cochlospermum angolensis) is an African tree whose bark has recently emerged as a herbal dietary supplement with claims for antioxidant activity. In order to substantiate the claimed activity of borututu supplements, we performed an activity-guided fractionation of the total extract utilizing a 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging assay. Subsequent flash and centrifugal chromatography resulted in the isolation of gallic acid () and protocatechuic acid () as the main antioxidant constituents. Two apocarotenoids and one flavonoid were also isolated from the chloroform fraction and were identified as cochloxanthin (), dihydrocochloxanthin (), and 7,4′-dimethyltaxifolin (), respectively. A High-performance liquid chromatography (HPLC) method was also developed for fingerprinting borututu samples, with Compounds – suggested as chemical markers for quality control purposes.

No MeSH data available.


Related in: MedlinePlus