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NMR, HPLC-ESI-MS, and MALDI-TOF MS analysis of condensed tannins from Delonix regia (Bojer ex Hook.) Raf. and their bioactivities.
J Agric Food Chem. 2012 May 16; 60(19):5013-22.JA

Abstract

The structures of the condensed tannins isolated from leaf, fruit, and stem bark of Delonix regia (Bojer ex Hook.) Raf. have been investigated with (13)C nuclear magnetic resonance ((13)C NMR) and high performance liquid chromatography electrospray ionization mass spectrometry (HPLC-ESI-MS) coupled with thiolysis and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analyses. The results showed that these condensed tannins from D. regia possessed structural heterogeneity in monomer units and degree of polymerization. Propelargonidin (PP) and procyanidin (PC) were found in the leaf, fruit, and stem bark of D. regia, while prodelphinidin (PD) was found only in the leaves. The polymer chain lengths of condensed tannins from leaf and fruit organs were detected to be trimers to hexadecamers but from trimers to tridecamers for stem bark. B-type linkages were present in all these compounds. Condensed tannins from different parts of D. regia can be explored as tyrosinase inhibitors and food antioxidants because of their potent antityrosinase and antioxidant activities. The inhibitor concentration leading to 50% enzyme activity (IC(50)) was estimated to be 38 ± 1, 73 ± 2, and 54 ± 1.5 μg/mL for the condensed tannins of leaf, fruit, and stem bark. Condensed tannins extracted from stem bark exhibited the highest antioxidant activity; the DPPH scavenging activity (IC(50)) and the FRAP values were 90 ± 2 μg/mL and 5.42 ± 0.09 mmol AAE/g, respectively.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chai WM
School of Life Sciences, Key Laboratory of the Ministry of Education for Coastal and Wetland Ecosystems, Xiamen University, Xiamen 361005, China.
Shi Y
No affiliation info available
Feng HL
No affiliation info available
Qiu L
No affiliation info available
Zhou HC
No affiliation info available
Deng ZW
No affiliation info available
Yan CL
No affiliation info available
Chen QX
No affiliation info available

MeSH

AntioxidantsChromatography, High Pressure LiquidEnzyme InhibitorsFabaceaeKineticsMagnetic Resonance ImagingMonophenol MonooxygenasePlant ExtractsPolymerizationProanthocyanidinsSpectrometry, Mass, Electrospray IonizationSpectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Pub Type(s)

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

Language

eng

PubMed ID

22515734

Citation

Chai, Wei-Ming, et al. "NMR, HPLC-ESI-MS, and MALDI-TOF MS Analysis of Condensed Tannins From Delonix Regia (Bojer Ex Hook.) Raf. and Their Bioactivities." Journal of Agricultural and Food Chemistry, vol. 60, no. 19, 2012, pp. 5013-22.
Chai WM, Shi Y, Feng HL, et al. NMR, HPLC-ESI-MS, and MALDI-TOF MS analysis of condensed tannins from Delonix regia (Bojer ex Hook.) Raf. and their bioactivities. J Agric Food Chem. 2012;60(19):5013-22.
Chai, W. M., Shi, Y., Feng, H. L., Qiu, L., Zhou, H. C., Deng, Z. W., Yan, C. L., & Chen, Q. X. (2012). NMR, HPLC-ESI-MS, and MALDI-TOF MS analysis of condensed tannins from Delonix regia (Bojer ex Hook.) Raf. and their bioactivities. Journal of Agricultural and Food Chemistry, 60(19), 5013-22. https://doi.org/10.1021/jf300740d
Chai WM, et al. NMR, HPLC-ESI-MS, and MALDI-TOF MS Analysis of Condensed Tannins From Delonix Regia (Bojer Ex Hook.) Raf. and Their Bioactivities. J Agric Food Chem. 2012 May 16;60(19):5013-22. PubMed PMID: 22515734.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - NMR, HPLC-ESI-MS, and MALDI-TOF MS analysis of condensed tannins from Delonix regia (Bojer ex Hook.) Raf. and their bioactivities. AU - Chai,Wei-Ming, AU - Shi,Yan, AU - Feng,Hui-Ling, AU - Qiu,Ling, AU - Zhou,Hai-Chao, AU - Deng,Zi-Wei, AU - Yan,Chong-Ling, AU - Chen,Qing-Xi, Y1 - 2012/05/03/ PY - 2012/4/21/entrez PY - 2012/4/21/pubmed PY - 2012/9/22/medline SP - 5013 EP - 22 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 60 IS - 19 N2 - The structures of the condensed tannins isolated from leaf, fruit, and stem bark of Delonix regia (Bojer ex Hook.) Raf. have been investigated with (13)C nuclear magnetic resonance ((13)C NMR) and high performance liquid chromatography electrospray ionization mass spectrometry (HPLC-ESI-MS) coupled with thiolysis and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analyses. The results showed that these condensed tannins from D. regia possessed structural heterogeneity in monomer units and degree of polymerization. Propelargonidin (PP) and procyanidin (PC) were found in the leaf, fruit, and stem bark of D. regia, while prodelphinidin (PD) was found only in the leaves. The polymer chain lengths of condensed tannins from leaf and fruit organs were detected to be trimers to hexadecamers but from trimers to tridecamers for stem bark. B-type linkages were present in all these compounds. Condensed tannins from different parts of D. regia can be explored as tyrosinase inhibitors and food antioxidants because of their potent antityrosinase and antioxidant activities. The inhibitor concentration leading to 50% enzyme activity (IC(50)) was estimated to be 38 ± 1, 73 ± 2, and 54 ± 1.5 μg/mL for the condensed tannins of leaf, fruit, and stem bark. Condensed tannins extracted from stem bark exhibited the highest antioxidant activity; the DPPH scavenging activity (IC(50)) and the FRAP values were 90 ± 2 μg/mL and 5.42 ± 0.09 mmol AAE/g, respectively. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/22515734/NMR_HPLC_ESI_MS_and_MALDI_TOF_MS_analysis_of_condensed_tannins_from_Delonix_regia__Bojer_ex_Hook___Raf__and_their_bioactivities_ L2 - https://doi.org/10.1021/jf300740d DB - PRIME DP - Unbound Medicine ER -