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Preparative separation and bioactivity of oligomeric proanthocyanidins

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Abstract

Oligomeric proanthocyanidins are among the most widely distributed polyphenols in the plant kingdom, being endowed with antioxidant, anti-inflammatory, antimicrobial, immunomodulatory, antitumor and cardioprotective activities. Since oligomeric proanthocyanidins are found in limited amounts in plants and plant-derived products, there is a great need for efficient separation methodologies that can supply analytical quality standards or sufficient material for further bioassays. By efficiently providing a good molar mass distribution of oligomeric proanthocyanidins according to their degree of polymerization, Sephadex LH is the most used sorbent in column chromatography, together with other size exclusion polymers, such as Toyopearl, Diaion, MCI gel CHP or Amberlite. Combination of normal and reversed-phase high pressure liquid chromatography can significantly reduce the total number of chromatographic steps required to obtain high purity oligomeric proanthocyanidins, whereas hydrophilic interaction liquid chromatography on Diol phases can yield proanthocyanidins with a higher degree of polymerization. By lacking a solid support, countercurrent separations can solve issues related to irreversible adsorption, giving higher recoveries, low sample denaturation and a facile scale-up from analytical to industrial production. By taking advantage of the complementarity of all these chromatographic techniques, high-purity oligomeric proanthocyanidin fractions or individual compounds can be obtained on a large scale in a reduced number of separation steps.

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Abbreviations

ABTS:

2-2′-Azino-di-(3-ethylbenzthiazoline sulfonic acid)

BHA:

Butylhydroxyanisole

CC:

Column chromatography

CCS:

Countercurrent separation

CPC:

Centrifugal partition chromatography

DP:

Degree of polymerization

DPPH:

2,2-Diphenyl-1-picrylhydrazyl

EC50 :

Efficient concentration 50%

FRAP:

Ferric reducing antioxidant power

HILIC:

Hydrophilic interaction liquid chromatography

HPLC:

High-pressure liquid chromatography

HSCCC:

High-speed countercurrent chromatography

IFN:

Interferon

IL:

Interleukin

LPLC:

Low-pressure liquid chromatography

LPS:

Lipopolysaccharide

LSRCCC:

Low-speed rotary countercurrent chromatography

MIP:

Macrophage inflammatory protein

MLCCC:

Multi-layer countercurrent chromatography

MMP:

Metalloproteinase

MPLC:

Medium-pressure liquid chromatography

NADPH:

Reduced nicotinamide adenine dinucleotide phosphate

NBT:

Nitroblue tetrazolium

NK:

Natural killer

NO:

Nitric oxide

NP:

Normal-phase

PA:

Proanthocyanidin

PC:

Procyanidin

PD:

Prodelphinidin

PMN:

Polymorphonuclear

RP:

Reversed-phase

TEAC:

Trolox equivalent antioxidant capacity

Th:

T helper

TLC:

Thin-layer chromatography

TNF-α:

Tumor necrosis factor alpha

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Authors and Affiliations

  1. Department of Pharmacognosy, Faculty of Pharmacy, Grigore T. Popa University of Medicine and Pharmacy Iasi, 16 Universitatii Street, 700115, Iasi, Romania

    Simon Vlad Luca, Alexandra Bujor, Anca Miron, Ana Clara Aprotosoaie & Adriana Trifan

  2. Department of Pharmacognosy with Medicinal Plant Unit, Medical University of Lublin, 1 Chodzki Street, 20-093, Lublin, Poland

    Simon Vlad Luca & Krystyna Skalicka-Woźniak

  3. Department of Pharmaceutical Technology, Faculty of Pharmacy, Grigore T. Popa University of Medicine and Pharmacy Iasi, 16 Universitatii Street, 700115, Iasi, Romania

    Alexandra Bujor

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  1. Simon Vlad Luca
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  2. Alexandra Bujor
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  3. Anca Miron
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Correspondence to Anca Miron or Krystyna Skalicka-Woźniak.

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Luca, S.V., Bujor, A., Miron, A. et al. Preparative separation and bioactivity of oligomeric proanthocyanidins. Phytochem Rev 19, 1093–1140 (2020). https://doi.org/10.1007/s11101-019-09611-5

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