Willow bark proanthocyanidins with potential for water treatment: Chemical characterization and zinc/bisphenol A removal

Jinze Dou; Toni Varila; Juha-Pekka Salminen; Sari Tuomikoski; Sami Hietala; Maria Hemmi; Tao Hu; Ulla Lassi; Tapani Vuorinen

doi:10.1016/j.seppur.2023.123943

Willow bark proanthocyanidins with potential for water treatment: Chemical characterization and zinc/bisphenol A removal

Jinze Dou
, Toni Varila
, Juha-Pekka Salminen
, Sari Tuomikoski
, Sami Hietala
, Maria Hemmi
, Tao Hu
, Ulla Lassi
, Tapani Vuorinen

Research output: Contribution to journal › Article › Scientific › peer-review

5 Citations (Scopus)

101 Downloads (Pure)

Abstract

This study investigates the chemical structure of proanthocyanidin-rich crude extracts from willow bark and these materials were tested initially as adsorbents for artificial (waste)water treatment. The crude extracts were obtained through mild water extraction and the colorant fractions were further chromatographically fractionated to understand the chemical structure of the willow bark proanthocyanidins. The chemistry of crude extracts and purified fractions were investigated using nuclear magnetic resonance (NMR) and ultraperformance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Both NMR (liquid and solid-state) and UPLC-MS/MS suggest that the crude extracts constitute of interflavan linked flavan-3-ols, i.e. proanthocyanidins with both procyanidin (PC)-type and prodelphinidin (PD)-type subunits, with the PC/PD ratio of approximately 2.3–2.5. PD-type proanthocyanidins were detected from the purified colorant fractions only with UPLC-MS/MS. Both the UPLC-MS/MS and size exclusion chromatography suggest that the crude extracts have an average oligomerization degree of roughly 5–6 flavan-3-ol units. Adsorption experiments showed that the activated foams made of crude extracts were effective in removing both zinc and Bisphenol A (BPA) with removal efficiencies of roughly 80–90% and thus these willow bark-derived proanthocyanidins are promising in water treatment. The significance of this study suggests the upgrading use of crude extracts for water treatment could significantly improve the value of willow bark.

Original language	English
Article number	123943
Number of pages	10
Journal	Separation and Purification Technology
Volume	318
Early online date	6 May 2023
DOIs	https://doi.org/10.1016/j.seppur.2023.123943
Publication status	Published - 1 Aug 2023
MoE publication type	A1 Journal article-refereed

Funding

This work made use of the RawMatTERS Finland infrastructure (RAMI) facilities based at Aalto University. This work was a part of the Academy of Finland's Flagship Programme under Project No. 318890 and No. 318891 (Competence Center for Materials Bioeconomy, FinnCERES). Dr. Leena Pitkänen from Aalto University provided the assistance for the molecular weight analysis using Gel Permeation Chromatography. The NMR premises from the University of Helsinki is also appreciated. This work made use of the RawMatTERS Finland infrastructure (RAMI) facilities based at Aalto University. This work was a part of the Academy of Finland's Flagship Programme under Project No. 318890 and No. 318891 (Competence Center for Materials Bioeconomy, FinnCERES). Dr. Leena Pitkänen from Aalto University provided the assistance for the molecular weight analysis using Gel Permeation Chromatography. The NMR premises from the University of Helsinki is also appreciated.

Keywords

NMR
Proanthocyanidins
Procyanidins
Prodelphinidins
Tannin
UPLC-MS/MS
Water treatment

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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CHEM_Dou_et_al_Willow_bark_2023_Separation_and_Purification_TechnologyFinal published version, 6.32 MBLicence: CC BY

Cite this

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title = "Willow bark proanthocyanidins with potential for water treatment: Chemical characterization and zinc/bisphenol A removal",

abstract = "This study investigates the chemical structure of proanthocyanidin-rich crude extracts from willow bark and these materials were tested initially as adsorbents for artificial (waste)water treatment. The crude extracts were obtained through mild water extraction and the colorant fractions were further chromatographically fractionated to understand the chemical structure of the willow bark proanthocyanidins. The chemistry of crude extracts and purified fractions were investigated using nuclear magnetic resonance (NMR) and ultraperformance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Both NMR (liquid and solid-state) and UPLC-MS/MS suggest that the crude extracts constitute of interflavan linked flavan-3-ols, i.e. proanthocyanidins with both procyanidin (PC)-type and prodelphinidin (PD)-type subunits, with the PC/PD ratio of approximately 2.3–2.5. PD-type proanthocyanidins were detected from the purified colorant fractions only with UPLC-MS/MS. Both the UPLC-MS/MS and size exclusion chromatography suggest that the crude extracts have an average oligomerization degree of roughly 5–6 flavan-3-ol units. Adsorption experiments showed that the activated foams made of crude extracts were effective in removing both zinc and Bisphenol A (BPA) with removal efficiencies of roughly 80–90\% and thus these willow bark-derived proanthocyanidins are promising in water treatment. The significance of this study suggests the upgrading use of crude extracts for water treatment could significantly improve the value of willow bark.",

keywords = "NMR, Proanthocyanidins, Procyanidins, Prodelphinidins, Tannin, UPLC-MS/MS, Water treatment",

author = "Jinze Dou and Toni Varila and Juha-Pekka Salminen and Sari Tuomikoski and Sami Hietala and Maria Hemmi and Tao Hu and Ulla Lassi and Tapani Vuorinen",

note = "Funding Information: This work made use of the RawMatTERS Finland infrastructure (RAMI) facilities based at Aalto University. This work was a part of the Academy of Finland's Flagship Programme under Project No. 318890 and No. 318891 (Competence Center for Materials Bioeconomy, FinnCERES). Dr. Leena Pitk{\"a}nen from Aalto University provided the assistance for the molecular weight analysis using Gel Permeation Chromatography. The NMR premises from the University of Helsinki is also appreciated. Publisher Copyright: {\textcopyright} 2023 The Author(s)",

year = "2023",

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doi = "10.1016/j.seppur.2023.123943",

language = "English",

volume = "318",

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T1 - Willow bark proanthocyanidins with potential for water treatment: Chemical characterization and zinc/bisphenol A removal

AU - Dou, Jinze

AU - Varila, Toni

AU - Salminen, Juha-Pekka

AU - Tuomikoski, Sari

AU - Hietala, Sami

AU - Hemmi, Maria

AU - Hu, Tao

AU - Lassi, Ulla

AU - Vuorinen, Tapani

N1 - Funding Information: This work made use of the RawMatTERS Finland infrastructure (RAMI) facilities based at Aalto University. This work was a part of the Academy of Finland's Flagship Programme under Project No. 318890 and No. 318891 (Competence Center for Materials Bioeconomy, FinnCERES). Dr. Leena Pitkänen from Aalto University provided the assistance for the molecular weight analysis using Gel Permeation Chromatography. The NMR premises from the University of Helsinki is also appreciated. Publisher Copyright: © 2023 The Author(s)

PY - 2023/8/1

Y1 - 2023/8/1

N2 - This study investigates the chemical structure of proanthocyanidin-rich crude extracts from willow bark and these materials were tested initially as adsorbents for artificial (waste)water treatment. The crude extracts were obtained through mild water extraction and the colorant fractions were further chromatographically fractionated to understand the chemical structure of the willow bark proanthocyanidins. The chemistry of crude extracts and purified fractions were investigated using nuclear magnetic resonance (NMR) and ultraperformance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Both NMR (liquid and solid-state) and UPLC-MS/MS suggest that the crude extracts constitute of interflavan linked flavan-3-ols, i.e. proanthocyanidins with both procyanidin (PC)-type and prodelphinidin (PD)-type subunits, with the PC/PD ratio of approximately 2.3–2.5. PD-type proanthocyanidins were detected from the purified colorant fractions only with UPLC-MS/MS. Both the UPLC-MS/MS and size exclusion chromatography suggest that the crude extracts have an average oligomerization degree of roughly 5–6 flavan-3-ol units. Adsorption experiments showed that the activated foams made of crude extracts were effective in removing both zinc and Bisphenol A (BPA) with removal efficiencies of roughly 80–90% and thus these willow bark-derived proanthocyanidins are promising in water treatment. The significance of this study suggests the upgrading use of crude extracts for water treatment could significantly improve the value of willow bark.

AB - This study investigates the chemical structure of proanthocyanidin-rich crude extracts from willow bark and these materials were tested initially as adsorbents for artificial (waste)water treatment. The crude extracts were obtained through mild water extraction and the colorant fractions were further chromatographically fractionated to understand the chemical structure of the willow bark proanthocyanidins. The chemistry of crude extracts and purified fractions were investigated using nuclear magnetic resonance (NMR) and ultraperformance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Both NMR (liquid and solid-state) and UPLC-MS/MS suggest that the crude extracts constitute of interflavan linked flavan-3-ols, i.e. proanthocyanidins with both procyanidin (PC)-type and prodelphinidin (PD)-type subunits, with the PC/PD ratio of approximately 2.3–2.5. PD-type proanthocyanidins were detected from the purified colorant fractions only with UPLC-MS/MS. Both the UPLC-MS/MS and size exclusion chromatography suggest that the crude extracts have an average oligomerization degree of roughly 5–6 flavan-3-ol units. Adsorption experiments showed that the activated foams made of crude extracts were effective in removing both zinc and Bisphenol A (BPA) with removal efficiencies of roughly 80–90% and thus these willow bark-derived proanthocyanidins are promising in water treatment. The significance of this study suggests the upgrading use of crude extracts for water treatment could significantly improve the value of willow bark.

KW - NMR

KW - Proanthocyanidins

KW - Procyanidins

KW - Prodelphinidins

KW - Tannin

KW - UPLC-MS/MS

KW - Water treatment

UR - https://www.scopus.com/pages/publications/85156191045

U2 - 10.1016/j.seppur.2023.123943

DO - 10.1016/j.seppur.2023.123943

M3 - Article

AN - SCOPUS:85156191045

SN - 1383-5866

VL - 318

JO - Separation and Purification Technology

JF - Separation and Purification Technology

M1 - 123943

ER -

Willow bark proanthocyanidins with potential for water treatment: Chemical characterization and zinc/bisphenol A removal

Abstract

Funding

Keywords

UN SDGs

Access to Document

Other files and links

Fingerprint

FinnCERES: Competence Center for the Materials Bioeconomy: A Flagship for our Sustainable Future

Raw Materials Research Infrastructure

Cite this

Willow bark proanthocyanidins with potential for water treatment: Chemical characterization and zinc/bisphenol A removal

Abstract

Funding

Keywords

UN SDGs

Access to Document

Other files and links

Fingerprint

Projects

FinnCERES: Competence Center for the Materials Bioeconomy: A Flagship for our Sustainable Future

Equipment

Raw Materials Research Infrastructure

Cite this