Journal of Functional Foods: Ting Xia, Bo Zhang, Wenhui Duan, Jin Zhang, Min Wang

Journal of Functional Foods xxx (xxxx) xxxx
Contents lists available at ScienceDirect
Journal of Functional Foods

journal homepage: www.elsevier.com/locate/jff
Nutrients and bioactive components from vinegar: A fermented and

functional food
⁎
Ting Xia, Bo Zhang, Wenhui Duan, Jin Zhang, Min Wang
State Key Laboratory of Food Nutrition and Safety, Key Laboratory of Industrial Fermentation Microbiology, College of Biotechnology, Tianjin University of Science and
Technology, Tianjin, China
A R T I C LE I N FO A B S T R A C T
Keywords: Vinegar has been widely used as acidic condiment worldwide for thousands of years. Vinegar contains various
Vinegar nutrients and bioactive components, which are brewed by liquid-state and solid-state fermentation techniques.
Nutrients This review highlights the nutrients and bioactive components in different types of vinegars and their functional
Bioactive components properties. Nutrients in vinegar include amino acids, sugars, vitamins, and minerals. The functions of these
Health benefits
nutrients were providence energy, regulation of cell metabolism regulation, immunoregulation, antioxidation,
Fermented food
anticoagulation and improvement of brain development. In addition, the bioactive components in vinegar in-
clude organic acids, polyphenols, melanoidins, and tetramethylpyrazine, which have the functions of anti-
oxidative activity, regulation of lipid metabolism, liver protection, blood pressure and glucose control, anti-
fatigue and anti-tumor. However, further studies are needed to explore the novel functional compounds in
vinegars and their molecular mechanisms on health benefits in future.
1. Introduction fermentation during the brewing process (Chen, Chen, et al., 2016).
These functional compounds not only contribute to the flavors of vi-
Vinegar, a kind of acidic condiment, has been in use for more than negars, but also play important roles in the prevention and treatment of
3000 years (Solieri & Giudici, 2009). Both solid-state and liquid-state human diseases, through their antibacterial and anti-inflammatory
fermentation methods are being used in the production of vinegar properties (Hindi, 2013), by regulating blood lipid levels (Beheshti
(Bertelli et al., 2015; Xu, Huang, et al., 2011; Xu, Xu, et al., 2011). et al., 2012), weight loss (Petsiou, Mitrou, Raptis, & Dimitriadis, 2014),
Based on the raw materials used, the vinegar produced may be classi- antifatigue (Cho et al., 2015), and antitumor (Baba, Higashi, &
fied into grain vinegar and fruit vinegar. Vinegar is a well-known fer- Kanekura, 2013). Otherwise, furan and HMF as the main products
mented food all over the world. In European countries, vinegar is during the Maillard reaction can be detected in vinegars (Lalou et al.,
mainly produced using liquid-state fermentation, such as balsamic vi- 2015; Nie, Huang, et al. 2013; Nie, Zheng et al., 2013), which have
negar, sherry vinegar, and apple cider vinegar. The raw materials used negative effects on human health (Capuano & Fogliano, 2011; Severin,
in the preparation of vinegar are fruits such as grapes, apples, tomatoes, Dumont, Jondeau-Cabaton, Graillot, & Chagnon, 2010). This review
persimmons, and pineapples. In Asian countries, most types of vinegar, summarizes the nutrients and bioactive compounds in vinegars and
including Kurozu vinegar, Shanxi aged vinegar, Zhenjiang aromatic their functional properties.
vinegar, and Baoning vinegar, are brewed by solid-state fermentation.
The raw materials comprise sorghum, wheat bran, beans, rice, and rice 2. Nutrients
hulls. The production processes of vinegar are shown in Fig. 1.
Vinegars are rich in nutrients and bioactive compounds including The nutritional constituents in vinegars include amino acids, sugars,
amino acids, sugars, organic acids, polyphenols, melanoidins, and tet- vitamins, and microelements, (Chou, Liu, Yang, Wu, & Chen, 2015;
ramethylpyrazine (Ho, Lazim, Fazry, Zaki, & Lim, 2016; Xia et al., Koyama et al., 2017), which can maintain acid base balance, regulate
2018). The kinds and concentrations of the substances in vinegars are cell metabolism, provide energy, and improve the immune system
closely related to the raw materials used and production technology (Budak, Aykin, Sevdim, Greene, & Guzel-Seydim, 2014; Kim, Hong,
employed, and the chemical reactions, physical changes, and microbial Suh, & Shin, 2016).
⁎
Corresponding author at: State Key Laboratory of Food Nutrition and Safety. Key Laboratory of Industrial Fermentation Microbiology, College of Biotechnology,
Tianjin University of Science & Technology, Tianjin 300457, China.
E-mail address: [email protected] (M. Wang).
https://doi.org/10.1016/j.jff.2019.103681
Received 19 August 2019; Received in revised form 5 November 2019; Accepted 13 November 2019
1756-4646/ © 2019 Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/BY-NC-ND/4.0/).
Please cite this article as: Ting Xia, et al., Journal of Functional Foods, https://doi.org/10.1016/j.jff.2019.103681
T. Xia, et al. Journal of Functional Foods xxx (xxxx) xxxx
Fig. 1. The production progress of vinegars.
2.1. Amino acids (Cho, Chang, & Chang, 2007). GABA also promotes diuresis and lowers
lipid levels and blood pressure (Dhakal, Bajpai, & Baek, 2012; Kimura,
Amino acids in vinegars are mainly derived from raw materials and Hayakawa, & Sansawa, 2002). Moreover, microorganisms have the
proteins of microbial decomposition (Maestre et al., 2008). Recent ability to decompose high molecular weight proteins into peptides and
studies have reported the presence of both free and nonprotein amino amino acids during fermentation. Ye, Morimura, Han, Shigematsu, and
acids in vinegars (Álvarez-Cáliz et al., 2012; Chen, Gui, Shi, Zhang, & Kida (2004) demonstrated that the main components in vinegars
Chen, 2013). The amino acids in the different types of vinegars are showed angiotensin I- converting enzyme (ACE) inhibitory activity in
shown in Table 1. vitro, which may be because of the peptides, whose content increased
By comparing the data of amino acids in different types of vinegars during acetic acid fermentation. Collectively, the functions of amino
(Table 1), glutamic acid is the highest that is present both in grain and acids in vinegars are regulation of cell metabolism, antioxidant activity
fruit vinegars (Fan et al., 2011; Kim, Cho, & Shin, 2012; Wang et al., and improvement of immunity and brain nervous development.
2017). The concentration of glutamic acid in grain vinegars
(294.9 ± 17.1–887.5 ± 53.5 mg/100 g) is higher than that in fruit
vinegars (373.2 ± 0.6–390.5 ± 0.02 mg/L). Chen et al. (2013) re- 2.2. Sugars
ported that the concentration of alanine ranges from 1.59 to 3.51 mg/
mL, which is the highest in Shanxi aged vinegar. In addition, total The sugars in the different types of vinegars are shown in Table 2.
concentration of amino acids increased with the aging time. The find- Several studies have reported that the monosaccharides in vinegars
ings are in accordance with those of Xia et al. (2018). A study carried comprise glucose, fructose, xylose, mannitose, and arabinose (Li, Yu, &
out by Chinnici, Durán-Guerrero, and Riponi (2015) showed that total Fan, 2014; Pinu, Carvalho-Silva, Uetanabaro, & Villas-Boas, 2016; Sun,
of 24 amino acids have been detected by high performance liquid Shan, Li, & Sun, 2011). Fructose and glucose are both present in fruit
chromatography (HPLC) in traditional balsamic vinegar, balsamic vi- vinegars, which provide the sweet taste to them (Caligiani, Acquotti,
negar, and sherry vinegar. The contents of proline in the three vinegars Palla, & Bocchi, 2007; Pinu et al., 2016). In addition, disaccharides in
were 494.67, 98.8, and 308.56 mg/kg, respectively, which are the vinegars include sucrose, maltose and mycose (Koyama et al., 2017;
highest amount of amino acids in three types of vinegars. Li et al. Pinu et al., 2016). It was found that balsamic vinegar contains 9 sugars
(2018) reported that 13 peptides in vinegars were detected by multiple (galactose, glucose, fructose, mannose, ribose, sorbose, xylose, mycose
reaction monitoring (MRM). During fermentation, the gluten proteins and sucrose) and 4 sugar alcohols (mannitol, glycerol, erythritol and
are partially hydrolyzed into peptides. inositol) (Pinu et al., 2016). According to Li et al. (2014), there are 8
Amino acids are not only crucial nutrients that can regulate cellular monosaccharides (glucopyranose, fructose, xylose, galactopyranose,
metabolism, but also bioactive compounds that can play important ribose, arabinopyranose, mannopyranose and rhamnose) and 6 alditols
roles in improving immunity and promoting brain development (erythritol, ribitol, arabitol, sorbitol, inositol, and xylitol) in sorghum
(Massey, Blakeslee, & Pitkow, 1998; Ren et al., 2017). When these vinegar. Polysaccharides are macromolecules, which may account for a
amino acids in vinegars are absorbed by the human body, they exhibit relatively small amount in some vinegars. The structural and chemical
both biological and metabolic qualities similar to those of free amino properties of polysaccharides have not been investigated to the same
acids, and also form complex peptides such as immunoglobulins, carrier extent as those of smaller molecules, which should be further explored.
proteins, and neurotransmitters. In addition, some amino acids from Sugars are an essential source of carbon during microbial fermen-
vinegars have strong antioxidant activity, such as histidine, methionine, tation of the brewing process, and also a source of energy. Recent
cysteine, tryptophan and tyrosine (Brosnan & Brosnan, 2006; Morozova studies have demonstrated that the sugars in vinegars exhibit im-
& Yurkovskaya, 2015; Udenigwe & Aluko, 2011). Moreover, γ-amino- munoregulatory, antioxidant, and anticoagulant activities. In the study
butyric acid (GABA), a nonprotein amino acid, is produced during the conducted by Sun et al. (2011), the polysaccharides of buckwheat vi-
process of acetic acid fermentation during the synthesis of vinegars negar were mainly composed of arabinose, xylose, glucose, mannose,
(Tian, Chen, He, & Chen, 2017). GABA is an important inhibitory and galactose. Tartary buckwheat vinegar and its polysaccharide sub-
neurotransmitter in brain tissues, which improves cerebral blood flow stances showed good antioxidant capacities by 1-diphenyl-2-picrylhy-
and cell metabolism, and has anti-anxiety and tranquilizing effects drazyl (DPPH) radical scavenging, hydroxyl free radical scavenging and
the total reducing power methods. Kim et al. (2016) reported that
2
Table 1
Amino acids in various types of vinegars.
T. Xia, et al.
Vinegars Main materials Fermentation Country Detection method Amino acids References
techniques
Sorghum vinegar Sorghum, wheat bran, rice hull, Solid fermentation China Amino acid analyzer Asparagine, threonine, serine, glutamic acid, glycine, alanine, cysteine, valine, Fan et al. (2011)
great koji methionine, leucine, isoleucine, tyrosine, phenylalanine, histidine, lysine, arginine
and proline
Oat vinegar – – China Amino acid analyzer Asparagine, threonine, serine, glutamic acid, glycine, alanine, cysteine, valine, Fan et al. (2011)
methionine, leucine, isoleucine, tyrosine, phenylalanine, histidine, lysine, arginine
and proline
Tartary buckwheat vinegar – – China Amino acid analyzer Asparagine, threonine, serine, glutamic acid, glycine, alanine, cysteine, valine, Fan et al. (2011)
methionine, leucine, isoleucine, tyrosine, phenylalanine, histidine, lysine, arginine
and proline
Zhenjiang Hengshun Rice, wheat bran, rice hull, wheat Liquid fermentation China Amino acid analyzer asparagine, threonine, serine, glutamic acid, glycine, alanine, cysteine, valine, Fan et al. (2011)
vinegar koji methionine, leucine, isoleucine, tyrosine, phenylalanine, histidine, lysine, arginine
and proline
Liubiju rice vinegar Rice, starch, wheat bran, rice hull, Liquid fermentation China Amino acid analyzer Asparagine, threonine, serine, glutamic acid, glycine, alanine, cysteine, valine, Fan et al. (2011)
wheat koji, yeast powder methionine, leucine, isoleucine, tyrosine, phenylalanine, histidine, lysine, arginine
and proline
Pomegranate vinegar Pomegranate Liquid fermentation Korea Amino acid analyzer Aspartic acid, glutamic acid, serine, glycine, threonine, arginine, alanine, GABA, Kim et al. (2012)
valine, methionine, isoleucine, leucine, phenylalanine and lysine
Blackberry vinegar Blackberry Liquid fermentation Korea Amino acid analyzer Aspartic acid, glutamic acid, serine, glycine, threonine, arginine, alanine, GABA, Kim et al. (2012)
Blueberry vinegar Blueberry Liquid fermentation Korea Amino acid analyzer Aspartic acid, glutamic acid, serine, glycine, threonine, arginine, alanine, GABA, Kim et al. (2012)
Mulberry vinegar Mulberry Liquid fermentation Korea Amino acid analyzer Aspartic acid, glutamic acid, serine, glycine, threonine, arginine, alanine, GABA, Kim et al. (2012)
Cactus vinegar Cactus Liquid fermentation Korea Amino acid analyzer Aspartic acid, glutamic acid, serine, glycine, threonine, arginine, alanine, gaba, Kim et al. (2012)
3
Cherry vinegar Cherry Liquid fermentation Korea Amino acid analyzer Aspartic acid, glutamic acid, serine, glycine, threonine, arginine, alanine, GABA, Kim et al. (2012)
Red ginseng vinegar Red ginseng Liquid fermentation Korea Amino acid analyzer Aspartic acid, glutamic acid, serine, glycine, threonine, arginine, alanine, GABA, Kim et al. (2012)
Shanxi aged vinegar Sorghum Solid fermentation China Amino acid analyzer Lysine, valine, phenylalanine, leucine, isoleucine, threonine, methionine, tyrosine Chen et al. (2013)
aspartic acid, serine, glutamate, glycine, alanine, cysteine, arginine, proline,
histidine, ornithine, ammonia and taurine
Kurozu vinegar Steamed rice, koji Solid fermentation Japan HPLC Alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamate acid, Miyoshi et al.
glycine, histidine, isoleucine, allo-isoleucine, leucine, lysine, methionine, (2014)
phenylalanine, proline, serine, threonine, tryptophan, tyrosine and valine
Traditional balsamic Cooked must Liquid fermentation Italy HPLC Ammonium, aspartic acid, glutamic acid, hydroxyproline, serine, asparagine, Chinnici et al.
vinegar glutamine, glycine, histidine, threonine, alanine, arginine, proline, GABA, tyrosine, (2015)
valine, methionine, cysteine, isoleucine, tryptophan, leucine, phenylalanine,
ornithine and lysine
Balsamic vinegar Wine Liquid fermentation Italy HPLC Ammonium, aspartic acid, glutamic acid, hydroxyproline, serine, asparagine, Chinnici et al.
glutamine, glycine, histidine, threonine, alanine, arginine, proline, gaba, tyrosine, (2015)
Sherry vinegar Wine Liquid fermentation Spain HPLC Ammonium, aspartic acid, glutamic acid, hydroxyproline, serine, asparagine, Chinnici et al.
glutamine, glycine, histidine, threonine, alanine, arginine, proline, gaba, tyrosine, (2015)
Black vinegar – – China Amino acid analyzer Methionine, leucine, isoleucine, lysine, threonine, histidine, phenylalanine, valine, Chou et al. (2015)
tryptophan, cysteine, arginine, tyrosine, aspartic acid, glutamate acid, alanine,
glycine, serine and proline
(continued on next page)
Table 1 (continued)
Vinegars Main materials Fermentation Country Detection method Amino acids References
T. Xia, et al.
techniques
Balsamic vinegar Grape Liquid fermentation Italy GC–MS 2-Aminobutyric acid, 4-aminobutyric acid, 4-hydroxyproline, alanine, asparagine, Pinu et al. (2016)
aspartic acid, beta-alanine, glycine, glutamic acid, glutamine, histidine, isoleucine,
leucine, lysine, methionine, N-acetylglutamic acid, ornithine, phenylalanine,
proline, putrescine, pyroglutamic acid, serine, threonine, tyrosine and valine
Zhenjiang vinegar Sticky rice Solid fermentation China HPLC Aspartic acid, glutamate acid, valine, leucine, glycine, alanine, threonine, serine, Wang et al. (2017)
methionine, phenylalanine, proline, lysine, isoleucine, arginine, tyrosine, histidine
and tryptophan
Tomato vinegar Tomato Liquid fermentation Japan Ion exchange Pyroglutamic acid, glutamine, gaba, aspartic acid, alanine, asparagine, glutamate Koyama et al.
chromatography acid, phenylalanine, histidine, serine, cysteine, threonine, arginine, lysine, valine, (2017)
tyrosine, isoleucine, leucine, glycine, proline, methionine and tryptophan
Represents unknown main materials and fermentation techniques.
4
Table 2
Sugars in various types of vinegars.
Vinegars Main materials Fermentation techniques Country Detection method Sugars References
Balsamic vinegar Grape Liquid fermentation Italy NMR β-D-fructopyranose, β-D-fructofuranose, a-D-glucopyranose and β-D-glucopyranos Caligiani et al. (2007)
Tartary buckwheat vinegar Tartary buckwheat Solid fermentation China GC Arabinose, xylose, glucose, mannose and galactose Sun et al. (2011)
Sorghum vinegar Sorghum Solid fermentation China GC–MS Glucopyranose, fructose, xylose, galactopyranose, ribose, arabinopyranose, mannopyranose, rhamnose, Li et al. (2014)
erythritol, ribitol, arabitol, sorbitol, inositol and xylitol
Persimmon vinegar Persimmon Liquid fermentation Korean GC–MS Arabinose, mannose, galactose, rhamnose and galacturonic acid Kim et al. (2016)
Balsamic vinegar Grape Liquid fermentation Italy GC–MS Galactose, glucose, fructose, mannose, ribose, sorbose, xylose, mycose, sucrose, mannitol, glycerol, Pinu et al. (2016)
erythritol and inositol
Tomato vinegar Tomato Liquid fermentation Japan HPLC Sucrose and glucose Koyama et al. (2017)
Pomegranate vinegar Pomegranate Liquid fermentation Korean HPLC Glucose and fructose Kim et al. (2012)
Blackberry vinegar Blackberry Liquid fermentation Korean HPLC Glucose and fructose Kim et al. (2012)
Blueberry vinegar Blueberry Liquid fermentation Korean HPLC Glucose and fructose Kim et al. (2012)
Mulberry vinegar Mulberry Liquid fermentation Korean HPLC Glucose and fructose Kim et al. (2012)
Cactus vinegar Cactus Liquid fermentation Korean HPLC Glucose and fructose Kim et al. (2012)
Red ginseng vinegar Cherry Liquid fermentation Korean HPLC Glucose and fructose Kim et al. (2012)
Cherry vinegar Red ginseng Liquid fermentation Korean HPLC Glucose and fructose Kim et al. (2012)

T. Xia, et al.
Table 3
Vitamins and mineral elements in various types of vinegars.
Vinegars Main materials Fermentation techniques Country Detection method Vitamins and mineral elements References
Sorghum vinegar Sorghum, wheat bran, rice hull, great koji Solid fermentation China Fluorometer and colorimetric Thiamine, riboflavin, niacin acid and nicotinamide Fan et al. (2011)
method
Oat vinegar – – China Fluorometer and colorimetric Thiamine, riboflavin, niacin acid and nicotinamide Fan et al. (2011)
method
Tartary buckwheat vinegar – – China Fluorometer and colorimetric Thiamine, riboflavin, niacin acid and nicotinamide Fan et al. (2011)
method
Liubiju rice vinegar Rice, starch, wheat bran, rice hull, wheat Liquid fermentation China Fluorometer and colorimetric Thiamine and riboflavin Fan et al. (2011)
koji, yeast powder method
Palm vinegar Palm juice Liquid fermentation India HPLC VB3, VB5, ascorbic acid and folic acid Ghosh et al. (2015)
Balsamic vinegar Grape Liquid fermentation Italy GC–MS Nicotinic acid and nicotinamide Pinu et al. (2016)
5
Mature vinegar – – China SF-ICP-MS Na, Mg, K, Ca, Mn, Fe, Zn, Sr, As, Cr, Co, Ni, Cu, Se, Mo, Fu et al. (2013)
Cd, Sn, Sb, Ba and Pb
Spiced vinegar – – China SF-ICP-MS Na, Mg, K, Ca, Mn, Fe, Zn, Sr, As, Cr, Co, Ni, Cu, Se, Mo, Fu et al. (2013)
White vinegar – – China SF-ICP-MS Na, Mg, K, Ca, Mn, Fe, Zn, Sr, As, Cr, Co, Ni, Cu, Se, Mo, Fu et al. (2013)
Traditional home-made Turkish Grape/apple Liquid fermentation Turkey ICP-MS Se, Cr, Cu, Mg, Co, Zn, Na, K, Ca, Ni and Mn Ozturk et al. (2015)
vinegar
Palm vinegar Palm juice Liquid fermentation India HPLC Mg, Ca, Mn, Cu, Zn, Na, K and Fe Ghosh et al. (2015)
Black vinegar – – China ICP-OES K, Mg, Ca, Fe, Mn and Se Chou et al. (2015)
Andalusian wine vinegar Grape Liquid fermentation Spain ICP-OES Al, As, B, Ba, Ca, Cd, Co, Cr, Cu, Fe, K, Mg, Mn, Na, Ni, P, Paneque et al. (2016)
Pb, S, Sr, V and Zn
Tomato vinegar Tomato Liquid fermentation Japan AAS Ca, Na, K, Mg and Fe Koyama et al. (2017)

T. Xia, et al.
Table 4
Organic acids in various types of vinegars.
Vinegars Main materials Fermentation Country Detection Organic acids References
techniques method
Traditional balsamic Grape Liquid fermentation Italy HPLC Citric acid, tartaric acid, gluconic acid, malic acid, succinic acid, lactic acid and acetic acid Sanarico, Motta, Bertolini, and
vinegar Antonelli (2003)
Wine vinegar – – Spain NIR Tartaric acid, malic acid, lactic acid, acetic acid, citric acid and succinic acid Sáiz-Abajo et al. (2006)
Plum vinegar Plum Liquid fermentation China HPLC Acetic acid, tartaric acid and lactic acid Liu and He (2009)
Balsamic vinegar Grape Liquid fermentation Italy NMR Acetic acid, formic acid, citric acid, lactic acid, malic acid and succinic acid Lalou et al. (2015)
Balsamic vinegar Grape Liquid fermentation Italy NMR Acetic acid, formic acid, lactic acid, malic acid, succinic acid and tartaric acid Papotti et al. (2015)
Traditional balsamic Grape Liquid fermentation Italy NMR Acetic acid, formic acid, lactic acid, malic acid, succinic acid and tartaric acid Papotti et al. (2015)
vinegar
Persimmon vinegar Persimmon Liquid fermentation China HPLC Acetic acid, lactic acid, quinic acid, tartaric acid, propanedioic acid, malic acid, succinic acid Ren et al. (2016)
and citric acid
6
Apple vinegar Apple Liquid fermentation China HPLC Acetic acid, lactic acid, quinic acid, tartaric acid, propanedioic acid, malic acid, succinic acid Ren et al. (2016)
and citric acid
Kiwifruit vinegar Kiwifruit Liquid fermentation China HPLC Acetic acid, lactic acid, quinic acid, tartaric acid, propanedioic acid, malic acid, succinic acid Ren et al. (2016)
and citric acid
Shanxi aged vinegar Sorghum Solid fermentation China IC Acetic acid, propionic acid, butyric acid, 3-methyl butyric acid, pentanoic acid, hexanoic acid, Zhu et al. (2016)
lactic acid, succinic acid, tartaric acid and citric acid
Tomato vinegar Tomato Liquid fermentation Japan HPLC Acetic acid, citric acid, malic acid, succinic acid and lactic acid Koyama et al. (2017)
Baoning vinegar Wheat bran, Daqu Solid fermentation China HPLC Acetic acid, oxalic acid, citric acid, tartaric acid, L-malic acid, succinic acid, lactic acid, formic Zhang, Huang, and Zhou (2017)
acid and L-pyroglutamic acid
Zhenjiang vinegar Sticky rice Solid fermentation China GC–MS Acetic acid, 2-methyl propionate, 3-methylbutanoic acid, caproic acid, octanoic acid and Wang et al. (2017)
propionic acid
Balsamic vinegars Grape Liquid fermentation Italy GC-O Acetic acid, propanoic acid, 2-methylpropanoic acid, butanoic acid, 3-methylbutanoic acid, (E)- Corsini, Castro, Barroso, and
but-2-enoic acid, hexanoic acid, octanoic acid, 4-oxopentanoic acid, furan-2-carboxylic acid and Durán-Guerrero (2019)
2-phenylacetic acid

polysaccharides in Korean persimmon vinegar (KPV) were separated 2016). Organic acids in vinegars come from fermentation process and
into three different fractions (KPV-I, KPV-II and KPV-III). KPV-I en- raw materials. Acetic acid and lactic acid were the dominant organic
hanced the immunostimulatory activity by stimulating the production acids in vinegars, which mainly generated during the stage of acetic
of tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), interleukin-12 acid fermentation and alcohol fermentation, respectively (Nie, Huang,
(IL-12), and nitric oxide (NO) in macrophages. KPV-I was found to be et al. 2013; Nie, Zheng et al., 2013; Nie et al., 2017; Xu, Huang, et al.,
composed arabinose, mannose, galactose, rhamnose and galactonic acid 2011; Xu, Xu, et al., 2011). In addition, fruits contain organic acids such
using gas chromatography mass spectrometry (GC–MS) analysis. An- as malic acid, citric acid, artaric acid, lactic acid and succinic acid,
other study carried out by Li et al. (2014) indicates that alditols and which provide the source of organic acids in fruit vinegars (Bureau,
monosaccharides from sorghum vinegar can attenuate platelet ag- Scibisz, Le Bourvellec, & Renard, 2012; Soyer, Koca, & Karadeniz,
gregation by inhibiting cyclooxygenase-1 and thromboxane-A2 syn- 2003). The organic acids in the different types of vinegars are shown in
thase, which may be beneficial in the treatment of cardiovascular dis- Table 4.
eases. Therefore, recent studies demonstrate that sugars in vinegars By comparison of acetic acid in different types of vinegars, the
have the functions of immunoregulation, antioxidation and antic- content of acetic acid is the highest among organic acids, account for
oagulation. about 30–50% in total organic acids (Chen et al., 2013; Wang et al.,
2017). While acetic acid is the main volatile organic acid in the vinegar
2.3. Vitamins and minerals samples, lactic acid is the major nonvolatile organic acid (Fan et al.,
2011; Ren et al., 2016; Sáiz-Abajo, González-Sáiz, & Pizarro, 2006; Zhu
The vitamins and minerals in the different types of vinegars are et al., 2016). It was found that 10 organic acids in Shanxi aged vinegar
shown in Table 3. Recent studies reported that the vitamins in vinegars were identified by ion liquid chromatography (IC). Among them, the
are composed of vitamins B and C. By comparing the data from Ghosh, concentration of acetic acid (45945.9–87723.5 mg/L) was the highest
Chakraborty, Chatterjee, and Raychaudhuri (2015) and Fan et al. among volatile acids, and that of lactic acid (2575.7–30336.6 mg/L)
(2011), it was observed that grain vinegars mainly consisted of vitamin was the highest among nonvolatile acids (Zhu et al., 2016). However,
B including vitamins B1, B2, niacin acid, and nicotinamide of these, some studies have reported that the concentrations of tartaric acid and
niacin acid (29.24 ± 2.63 mg/100 g) showed the highest concentra- citric acid were higher than that of lactic acid (Koyama et al., 2017; Liu
tion. However, palm vinegar consisted of four water-soluble vitamins, & He, 2009; Liu et al., 2018; Sáiz-Abajo et al., 2006; Xu, Huang, et al.,
which included vitamins B3, B5, C, and folic acid, with the con- 2011; Xu, Xu, et al., 2011). Lalou et al. (2015) reported that, in bal-
centration of vitamin C (217 ± 6.3 mg/L) being the highest. A study samic vinegar, the presence of acetic acid, formic acid, citric acid, malic
by Paneque, Morales, Burgos, Ponce, and Callejón (2016) showed that acid, and succinic acid was identified by nuclear magnetic resonance
the 21 minerals (Al, As, B, Ba, Ca, Cd, Co, Cr, Cu, Fe, K, Mg, Mn, Na, Ni, (NMR), and that the concentration of acetic acid
P, Pb, S, Sr, V, and Zn) in Andalusian wine vinegars were determined (28.52 ± 2.14–63.57 ± 5.8 g/kg) was the highest among the organic
using the inductively coupled plasma optical-emission (ICP-OES) acids, followed by malic acid and citric acid. In addition, acetic acid
method. Fu, Nie, Xie, and Ferro (2013) reported that the 20 minerals was observed to contribute to the strong aroma and flavor of vinegars;
(Na, Mg, K, Ca, Cr, Mn, Fe, Co, Ni, Cu, Zn, As, Se, Sr, Mo, Cd, Sn, Sb, Ba, however, since lactic acid, tartaric acid, malic acid, and succinic acid
and Pb) found in mature vinegar, spiced vinegar, and white vinegar in could buffer the stimulation of acetic acid, it made the vinegars with a
China were detected using the sector field inductively coupled plasma mild flavor (Wang et al., 2017).
mass spectrometry (SF-ICP-MS). Organic acids in vinegars are not only considered as nutrients, but
Vitamins and minerals are essential nutrients for the human body bioactive components. Some organic acids in vinegars such as malic
(Nielsen, 1996; Zhang et al., 2018). As shown in Table S1, daily nu- acid, citric acid, succinic acid, and lactic acid can enter tricarboxylic
trition goals for adults based on dietary reference intakes and dietary acid cycle, which is the final metabolic pathway of three major nu-
guidelines recommendations from USDA. Niacin in vinegars plays a role trients (carbohydrate, lipid, amino acid) and produce energy. In addi-
in blood vessel expansion and cholesterol excretion (Ganji, Kamanna, & tion, organic acids in vinegars, especially acetic acid, can penetrate into
Kashyap, 2003). Vitamin C in the vinegars exhibits antioxidant activ- the cell membranes of microorganisms and cause bacterial cell death. It
ities by inhibiting lipid peroxidation and oxidative stress (Rodrigo, Prat, was demonstrated that acetic acid was the most effective organic acid
Passalacqua, Araya, & Bächler, 2008). In addition, many minerals such against Escherichia coli O157:H7, followed by lactic, citric, and malic
as K and Zn in vinegars can generate alkaline substances, which prevent acids (Entani, Asai, Tsujihata, Tsukamoto, & Ohta, 1998; Ryu, Deng, &
blood acidification and maintain an acid base balance. Taken together, Beuchant, 1999). Al-Rousan, Olaimat, et al. (2018) stated that the
vitamins and minerals in vinegars can provide daily nutritional needs to combination of acetic acid and citric acid exhibited a stronger anti-
human body, which are important to promote growth and development bacterial effect against bacteria (Salmonella Typhimurium, Escherichia
and regulate physiological functions. coli O157:H7, and Staphylococcus aureus) than acetic acid or citric acid
alone. Animal experiments have shown that administration of acetic
3. Bioactive components acid reduces serum cholesterol and triacylglycerols through inhibition
of lipogenesis in liver and increment in faecal bile acid excretion
The bioactive compounds in vinegars consist of organic acids, (Fushimi et al., 2006), and inhibits the accumulation of body fat by
polyphenols, melanoidins, and tetramethylpyrazine, which exhibit upregulation of genes for fatty acid oxidation enzymes in the liver
several health benefits, because of their antibacterial and antioxidant (Kondo, Kishi, Fushimi, & Kaga, 2009). Otherwise, feeding of acetic
activities, aiding in weight loss, blood pressure and glucose control, and acid and citrate in post-exercise rats enhance glycogen repletion in liver
expansion of blood vessels (Al-Rousan et al., 2018; Chen, Tian, et al., and skeletal muscle, which aid recovery from fatigue (Fushimi et al.,
2016; Kondo, Kishi, Fushimi, Ugajin, & Kaga, 2009). 2001). Shen et al. (2016) found that acetic acid (0.3% w/v) or vinegar
(5% v/v) alleviated dextran sulfate sodium (DSS)-induced colitis in
3.1. Organic acids mice by inhibition of Th1 and Th17 responses and NOD-like receptor
protein3 (NLRP3) inflammasome and activation of mitogen-activated
Organic acids in vinegars include volatile organic acids (such as protein kinase (MAPK) signal pathway. Other animal studies demon-
acetic acid, formic acid, propionic acid, butyric acid, and quinic acid) strated that vinegar and acetic acid decreased blood pressure in spon-
and nonvolatile organic acids (for example lactic acid, malic acid, taneously hypertensive rats by reducing renin activity and angiotensin
pyroglutamic acid, citric acid, and succinic acid) (Cocchi et al., 2006; Qi II (Kondo, Tayama, Tsukamoto, Ikeda, & Yamori, 2001) and down-
et al., 2013; Ren et al., 2016; Shi et al., 2013; Zhu, Zhu, Wang, & Li, regulating angiotensin II type 1 receptor expression via AMP-activated
7
protein kinase/PPARγ coactivator-1α/ peroxisome proliferator-acti- reported that there are 17 phenolic compounds in pomegranate vinegar
vated receptor γ (AMPK/PGC-1α/PPARγ) pathway (Na et al., 2016). determined by ultra-performance liquid chromatography-mass spec-
In studies from the 1960s, organic acids were proved to delay gas- trum (UPLC-MS), which is more than that in other vinegars. Among
tric emptying in dogs (Lin, Doty, Reedy, & Meyer, 1990). Moreover, these phenolic compounds in pomegranate vinegar, the content of
several studies have shown that organic acids and vinegars can lower protocatechuic acid (28.88 ± 0.02 mg/L) is the highest, followed by
gastric emptying in humans (Liljeberg & Björck, 1996, 1998). In a study that of gallic acid.
conducted by Kondo et al. (2009) in humans, daily intake of a drink It has been reported that the phenolic compounds in vinegars ex-
containing 15 mL vinegar (750 mg of acetic acid) for 12 weeks sig- hibit a high antioxidant activity, which is capable of reducing oxidative
nificantly decreased body weight in obese people, total cholesterol and stress in the body and aid in the regulation of lipid metabolism, blood
triglyceride in serum. This finding suggests that daily intake of vinegar pressure control, prevention of cardiovascular diseases, protection of
could be useful in prevention of obesity. Other studies demonstrated liver, and anti-aging. Many studies showed that the content of phenolic
that vinegar improved insulin sensitivity in humans with insulin re- compounds has a high correlation with the antioxidant activities of
sistance or type 2 diabetes (Johnston, Kim, & Buller, 2004), and en- vinegars (Verzelloni, Tagliazucchi, & Conte, 2007; Xie et al., 2017;
hanced muscle blood flow and glucose uptake in humans with impaired Yusoff et al., 2015). In the studies conducted by Bertelli et al. (2015)
glucose tolerance and hypertriglyceridaemia (Mitrou et al., 2015), and Xia et al. (2017), the antioxidant activities of traditional balsamic
suggesting that vinegar may be considered beneficial for improving vinegar from Modena and Shanxi aged vinegar increased with increase
insulin resistance and metabolic abnormalities. Generally, organic acids in the aging time. By comparison of different production technologies,
in vinegars were not only considered as nutrients but bioactive com- it was found that the antioxidant activity of the traditional vinegar was
pounds, which have benefit effects of antimicrobial, suppression of fat higher than that of the industrial vinegar (Budak & Guzel-Seydim,
accumulation and hyperlipemia, improvement of insulin resistance and 2010; Zhao et al., 2018). With respect to antioxidant activity results of
metabolic abnormalities reduction of hypertensive and anti-fatigue. different fruit vinegars, Hasim, Pınar, Nur, and Serkan (2017) reported
Further investigations to examine the efficacy of vinegar as prevention that the antioxidant activity of grape vinegars ranged from 5.39 to
and therapy are warranted. 14.43 mM Trolox/L (DPPH) and from 7.72 to 17.96 mM Trolox/L (2,2′-
azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS)), while anti-
3.2. Polyphenols oxidant activity of apple vinegars ranged from 2.65 to 14.69 mM
Trolox/L (DPPH) and from 4.05 to 20.19 mM Trolox/L (ABTS). These
Phenolic compounds in vinegars are chiefly derived from raw ma- findings suggest that grape vinegars exhibit a higher antioxidant ca-
terials. Several studies demonstrated that the raw materials of grain pacity than apple vinegars, which is in accordance with the results of
vinegars (such as sorghum, bran, barley, pea, and rice bran) contain an Bakir, Toydemir, Boyacioglu, Beekwilder, and Capanoglu (2016). In
amount of phenolic acids including gallic acid, ferulic acid, syringic addition, it has been demonstrated that the antioxidant activity of
acid, vanillic acids, protocatechuic acid, caffeic acid, chlorogenic acid, traditional balsamic vinegar was mainly due to the polyphenolic frac-
p-coumaric acid, p-hydroxybenzoic acid, sinapic acid, and salicylic acid tion (about 45%) and melanoidins (about 45%) (Tagliazucchi,
(Shimoji et al., 2002; Chen, Zhou, et al., 2016; Troszynska & Ciska, Verzelloni, & Conte, 2008). Moreover, cell culture and animal studies
2002; Dykes & Rooney, 2006). Other studies showed that the raw demonstrated that polyphenols in both grain vinegars and fruit vinegars
materials of fruit vinegars (such as apple, grape, pomegranate, pome- can reduce oxidative stress (Beh et al., 2016; Bertelli et al., 2015; Ubeda
granate, and blueberry) contain abundant phenolic acids including et al., 2013; Yun, Kim, & Koh, 2016), and protect the hepatocytes
catechin, syringic acid, gallic acid, chlorogenic acid, epicatechin, caf- against oxidative damage through the nuclear factor erythroid-2-re-
feic acid, ferulic acid, rutin, protocatechuic acid, and p-coumaric acid lated factor 2 (Nrf2) signaling pathway (Xia et al., 2017; Zou et al.,
(Aykın, Budak, & Guzel-Seydim, 2015; Budak & Guzel-Seydim, 2010; 2018). Recent animal experiments have shown that polyphenols of vi-
Plessi, Bertelli, & Miglietta, 2006; Veberic et al., 2010). They eliminate negars also decrease blood lipid levels (Budak et al., 2011), exhibit
hydroxyl radicals and superoxide anion free radicals via electron antihyperglycaemic activities (Yusoff et al., 2015), antithrombotic
transfer, subsequently terminating the chain reaction (Rice-Evans, ability (Fan et al., 2009), and antitumor (Shimoji et al., 2004). In
Miller, & Paganga, 1996). In addition, they chelate with metal ions to general, phenolic compounds in vinegars have functions of antioxidant
inhibit the oxidation reaction (Perron & Brumaghim, 2009). The phe- activity, regulation of lipid metabolism, blood pressure control, pre-
nolic acids in the different types of vinegars are shown in Table 5. vention cardiovascular disease, and protection of liver and antitumor.
By comparing the results from the phenolic compounds in vinegars
detected by the HPLC method, the amount of gallic acid 3.3. Melanoidins
(555.3 ± 2.32 mg/L) in Zhenjiang aromatic vinegar is the highest
phenolic compounds (Ren et al., 2016), whereas the content of caftaric Melanoidins are brown macromolecular compounds, which are
acid (176.61 ± 0.24 mg/L) in red wine vinegar is the highest (Cerezo formed between from sugars and nitrogenous compounds (amino acids,
et al., 2008). The findings suggest that the composition of phenolic peptides, and proteins) through the Maillard reaction (Wang, Qian, &
compounds depends on the vinegar samples and the production tech- Yao, 2011, Echavarría, Pagán, & Ibarz, 2012; Hodge, 1953). Melanoi-
nique employed. In addition, several studies have reported that the dins in vinegars are mainly produced during thermal and aging pro-
total concentration of polyphenols in vinegars increased with the aging cesses. Thermal processing is one of the solid-state fermentation pro-
time (Bertelli et al., 2015; Xia et al., 2017), indicating that the aging cesses in grain vinegars. During thermal processing, the residual starch,
process is an important factor impacting polyphenols in vinegars. hemicelluloses, protein and metabolites of microorganism are hydro-
Comparisons between the studies on phenolic compounds of vinegars, lyzed to reducing sugars and amino acids. Then, the reducing sugars
gallic acid, caffeic acid, and catechin are common phenolic compounds, and amino acids participate in the Maillard reaction are polymerized to
which can be detected in most types of vinegars. However, the number form melanoidins (Aili, Huanlu, Changzhong, & Zaigui, 2012). In ad-
of flavonoids in vinegars is still less. Chou et al. (2015) reported that dition, during the aging process, the decrease of the water content by
only one flavonoid compound (catechin) in lyophilized black vinegar evaporation (grain and fruit vinegars) and the extraction of some
powders is detected out of the flavonoid standards (catechin, epica- phenolic compounds from the wood (fruit vinegars) lead to the increase
techin, rutin, naringin, myricetin, hesperidin, quercitrin, neohesperidin, of phenolic compounds content (Alonso, Castro, Rodríguez, Guillén, &
eriodictyol, diosmin, morin, daidzein, quercetin, glycitein, naringenin, Barroso, 2004; Tesfaye, Lourdes Morales, García-Parílla, & Troncoso,
luteolin, genistein, hesperetin, kaempferol, apigenin, and isorhamnetin) 2002), which can link to melanoidins and become a part of their ske-
by HPLC analysis. It is worth mentioning that Kharchoufi et al. (2018) leton to increase the antioxidant capacity (Tagliazucchi, Verzelloni, &
8
T. Xia, et al.
Table 5
Phenolic acids and flavonoid in various types of vinegars.
Vinegars Main materials Fermentation Country Detection method Phenolic acids and flavonoid References
techniques
Traditional balsamic Grape Liquid fermentation Italy GC–MS 4-Hydroxybenzoic acid, vanillic acid, protocatecuic acid, syringic acid, isoferulic acid, p- Plessi et al. (2006)
vinegar coumaric acid, gallic acid, ferulic acid and caffeic acid
Balsamic vinegar Grape Liquid fermentation Italy GC–MS Protocatechuic acid, gallic acid, p-coumaric acid, syringic acid, caffeic acid, ferulic acid, Plessi et al. (2006)
vanillic acid and p-hydroxybenzoic acid
Red wine vinegar Red wines Liquid fermentation Spain HPLC Gallic acid, protocatechuic acid, caffeic acid, vanillic acid, catechin, caftaric acid, syringic Cerezo et al. (2008)
acid and ellagic acid
Tradition red wine Grape Liquid fermentation Turkey HPLC Gallic acid, catechin, caffeic acid, epicatechin, chlorogenic acid, syringic acid, p-coumaric Budak and Guzel-Seydim (2010)
vinegar acid and ferulic acid
Industry red wine Grape Liquid fermentation Turkey HPLC Gallic acid, catechin, caffeic acid, epicatechin, chlorogenic acid, syringic acid, p-coumaric Budak and Guzel-Seydim (2010)
vinegar acid and ferulic acid
Apple vinegar Apple Liquid fermentation Japan LC-MS Chlorogenic acid, 4-pcoumaroylquinic acid, isomer of chlorogenic acid, isomer of Nakamura et al. (2010)
pcoumaroylquinic acid, isomer of chlorogenic acid, p-hydroxybenzoic acid, p-hydroxybenzoic
acid and protocatechuic acid
Apple cider vinegar Apple Liquid fermentation Turkey HPLC Gallic acid, catechin, chlorogenic acid, caffeic acid, epicatechin and p-coumaric acid Budak et al. (2011)
Shanxi aged vinegar Sorghum Solid fermentation China UPLC-MS Protocatechuic acid, p-hydroxybenzoic acid, salicylic acid, dihydrosinapic acid, p-coumaric Chen, Zhou, et al. (2016)
acid, sinapic acid, dihydroferulic acid and ferulic acid
Black vinegar – – China HPLC Gallic acid, catechin, chlorogenic acid, p-hydroxybezoic acid, p-cumeric acid, ferulic acid, and Chou et al. (2015)
sinapic acid
Balsamic vinegar Grape Liquid fermentation Italy UHPLC–MS Gallic acid, protocatechuic acid, p-carboxyphenol acid, gentisic acid, hydroxytyrosol, vanillic Barnaba et al. (2015)
acid, syringic acid, caffeic acid, homovanillic acid, tyrosol, protocatechuic aldehyde,
pirocatecolo, p-coumaric acid, salicylic acid, phenol, catechin, ferulic acid, aesculetin,
9
sinapinic acid, homovanillic alcohol, epicatechin, vanillin, coniferyl alcohol, 4-
methylcatechol, syringaldehyde, isopropiovanillone, scopoletin, aceto-/isoacetovanillone,
isopropiosiringone, acetosyringone, isoacetosiringone, syringol, coniferylaldehyde,
sinapinaldehyde, tryptophol, o-vanillina, methyl vanillate, (m + p)-cresol, 4-ethylcatechol, o-
cresol, vanillyl ethyl ether, guaiacol, 4-methylsyringol, 4-vinylphenol, ethyl vanillate, 3,4-
xylenol, 4-vinylguaiacol, ellagic acid, 4-ethylphenol, 4-methylguaiacol, 4-ethylguaiacol, 4-
allylsyringol, eugenol and isoeugenol
Persimmon vinegar Persimmon Liquid fermentation China HPLC Gallic acid, catechin hydrate, chlorogenic acid, caffeic acid, p-coumaric acid, trans-ferulic Ren et al. (2016)
acid, (−)-epicatechin gallate and phloridzin
Apple vinegar Apple Liquid fermentation China HPLC Gallic acid, vanillic acid, chlorogenic acid, caffeic acid, p-coumaric acid, trans-ferulic acid, Ren et al. (2016)
(−)-epicatechin gallate and phloridzin
Kiwifruit vinegar Kiwifruit Liquid fermentation China HPLC Gallic acid, catechin hydrate, vanillic acid, chlorogenic acid, caffeic acid, p-coumaric acid, Ren et al. (2016)
trans-ferulic acid and phloridzin
Zhenjiang aromatic Sticky rice Solid fermentation China HPLC Gallic acid, catechin hydrate, vanillic acid, chlorogenic acid, epicatechin, p-coumaric acid and Ren et al. (2016)
vinegar trans-ferulic acid
Pomegranate vinegar Pomegranate Liquid fermentation America UPLC Gallic acid, galloylglucoside, protocatechuic acid, punicalagin, catechin, vanillic acid, syringic Kharchoufi et al. (2018)
acid, ethyl gallate, ellagic acid, chlorogenic acid, caffeic acid, p-coumaric acid, ferulic acid,
ferulic acid hexoside, tyrosol and trans-p-Coumaric derivate
Cornelian cherry vinegar Cornelian cherry Liquid fermentation France HPLC Ellagic acid, caffeoylquinic acid derivatives, p-coumaric acid derivatives, cyjanidin 3-o- Kawa-Rygielska, Adamenko,
galactoside, cyjanidin 3-o-robinobioside and pelargonidine 3-o-galactoside, pelargonidine 3- Kucharska, and Piórecki (2018)
o-robinobioside, aromadendrin 7-o-glucoside, quercetin 3-o-galactoside, quercetin 3-o-
glucuronide and kaempferol 3-o-galactoside
Persimmon vinegar Persimmon Liquid fermentation China LC-TOF-MS/MS, Hydroxycinnamic acids, caffeic acid, flavanols, gallocatechin, epigallocatechin, catechin, Zou et al. (2018)
HPLC epicatechin, epigallocatechin gallate, gallocatechin gallate, epicatechin gallate, procyanidin
A2 and rutin

Fig. 2. The possible structure of melanoidin in vinegars (Liu et al., 2017; Moreira, Nunes, Domingues, & Rosário, 2012).
Conte, 2010). Melanoidins whose molecular weight ranged from 10 to significant antibacterial activity to Escherichia coli, Staphylococcus
100 kDa are known as high molecular weight (HMW) compounds aureus and Bacillus subtilis, whereas the aqueous extract and low mo-
(Hofmann, 1998). Melanoidins have a strong ability to chelate with lecular weight (LMW) fraction had poor antibacterial activity. Briefly,
metal ions, thus effectively preventing the redox reaction of metal ions the functions of melanoidins in vinegars are antioxidant activity, pro-
(Pastoriza & Rufiãn-Henares, 2014). Additionally, phenolic acids in- tection of liver, and antibacterial activity.
corporated into melanoidins through non-covalent bonds, polymerize
with the melanoidins skeleton to further strengthen their antioxidant
properties (Liu et al., 2017; Tagliazucchi & Verzelloni, 2014). The 3.4. Tetramethylpyrazine
possible structure of melanoidins in vinegars is shown in Fig. 2.
Melanoidins in vinegars are mainly produced during thermal and Tetramethylpyrazine, also known as ligustrazine, is the common
aging processes, which influence the flavors of vinegar and its anti- product of Maillard reaction and microbial fermentation. Some studies
oxidant and antimicrobial activities (Rurián-Henares & Morales, 2008; were conducted to reveal the changes of tetramethylpyrazine during
Wang et al., 2011). In addition, some intermediates are generated the production process of vinegars. Li, Li, Liu, Luo, and Lin (2016) re-
during the process of Maillard reaction, such as reductone and het- ported that the relative content of tetramethylpyrazine was low
erocyclic compounds, which also exhibit antioxidant activities (0.12–0.63%) in the fermentation culture, which was obviously
(Echavarría et al., 2012). In vitro studies, HMW fractions in Zhenjiang changed during acetic acid fermentation of Shanxi aged vinegar. In
aromatic vinegar and traditional balsamic vinegar exhibited a strong addition, the content of tetramethylpyrazine of tartary buckwheat vi-
antioxidant activity (Tagliazucchi et al., 2008; Xu, Tao, & Ao, 2007). negar determined by GC–MS were increased in the first three days, and
The antioxidant activities of HMW melanoidins in traditional balsamic then gradually reduced from 4080.6 ± 258.5 to 1465.0 ± 92.8 μg/kg
vinegar determined by the ABTS and ferric reducing antioxidant power at the end of the thermal process, indicating a high content during
(FRAP) methods were 2750.3 ± 65.2 and 1286.2 ± 679.9 mg VC/kg, thermal processing (Wang, Zhang, & Li, 2012). Xu et al. (2011) reported
respectively, which contributed to 46.4 ± 1.1 and 43.6 ± 2.3% of the that the content of tetramethylpyrazine increased with storage time,
total antioxidant activity of the vinegar (Tagliazucchi et al., 2008). and that was 696.63 mg/L in 6-year-old Zhenjiang aromatic vinegar,
Meanwhile, melanoidins from vinegar reduced the reactive oxygen indicating that tetramethylpyrazine in vinegar is mainly formed during
species (ROS) in normal human liver cells and mouse livers through a the storage process, and the fermentation process was the accumulation
mitophagy-dependent pathway, which protected the liver from oxida- stage of precursors for the ligustrazine synthesis. A study conducted by
tive stress in vitro and in vivo (Yang, Wang, & Yang, 2014). Guo and Xiao, Zhao, Tian, Tian, and Zhao (2018) reported that tetra-
Yang (2016) reported that the HMW fractions in vinegar exhibit a methylpyrazine contents in 137 vinegar samples worldwide were de-
termined. The average tetramethylpyrazine contents were 24.483 and
10
Fig. 3. Proposed pathway for biosynthesis of tetramethylpyrazine (Shu, 1998; Larroche, Besson, & Gros, 1999).
11.905 mg/kg, respectively, from 96 vinegar samples brewed by solid microbial fermentation and brewing raw materials, which can reduce
fermentation in Shanxi province and other places of China, and tetra- blood lipid and blood pressure (Castaño et al., 2002). Baoning vinegar
methylpyrazine was not detected from 41 vinegar samples brewed by is a famous traditional vinegar in China, which is produced by the Daqu
liquid fermentation, which were in accordance with previous studies making, fermentation, decoction and filtering processes. Some tradi-
(Chen et al., 2010; Chinnici et al., 2009). These findings suggest that tional Chinese medicines are added into Daqu such as Amomum villosum
tetramenthylpyrazine present in vinegars from solid-state fermentation Lour., Elettaria cardamomum, Eucommia ulmoides and Angelica sinensis,
is likely due to thermal and aging processes. The proposed pathway for which provide the vinegar with novel health benefits, such as in-
the biosynthesis of tetramethylpyrazine is shown in Fig. 3. vigorating the spleen, nourishing the stomach, and building up the
Tetramethylpyrazine not only contributes to the flavor of vinegar, body. In addition, Cao, Song, Song, and Tian (2017) have demonstrated
but has beneficial effects on the inhibition of platelet aggregation, ex- that fluorescent nanoparticles (FNs) are present in Chinese mature vi-
pansion of blood vessels, reduction of blood lipids and antioxidation negar, which are about 1.40 ± 0.40 nm and mainly spherical. The
(Chen, Tian, et al., 2016; Wang, Guo, Han, Zhang, & Chen, 2009; Zhou, formation of FNs is possibly due to the denaturation of polysaccharides
Salganicoff, & Sevy, 1985). A cell culture study carried out by Chen, and protein at high temperatures, and the reassembly of the degraded
Tian, et al. (2016) reported that tetramethylpyrazine from Chinese oligosaccharide and amino acid during the production process. FNs
black vinegar has antioxidant and hypolipidemic activities in HepG2 from Chinese mature vinegar can interact with dopamine, which may
cells, which can improve lipid profiles by elevating the peroxisome add a new perspective to the potential health implications of food-
proliferator-activated receptors liver X receptors ATP binding cassette borne nanoparticles. However, further studies are needed to explore the
transporter (PPARγ-LXRa-ABCA1) pathway. This finding indicates that novel function of vinegars.
tetramethylpyrazine from vinegars has a therapeutic potential for car-
diovascular diseases. Tetramethylpyrazine not only contributes to the
flavor of vinegar, but has beneficial effects on inhibition of platelet 4. Actions of nutrients and bioactive compounds
aggregation, expansion of blood vessels, reduction of blood lipids and
antioxidation. Vinegars contain arrays of nutrients and bioactive compounds,
which are expecting to work together and exert as a total function to
modify the entire body system. There are few studies that reported the
3.5. Other bioactive compounds synergistic actions of nutrients and bioactive compounds in vinegars. A
study conducted by Chen, Zhou, et al. (2016) reported that there were 8
Some types of vinegars have more functions due to the special raw free phenolic acids in Shanxi aged vinegar. The results demonstrated
materials and brewing techniques used. For example, lovastatin, as a that sinapic acid reacted with protocatechuic acid, dihydro ferulic acid,
special ingredient of Monascus aged vinegar, is generated from p-coumaric acid or salicylic acid showed synergistic effect. Meanwhile,
11
ferulic acid reacted with dihydro ferulic acid, p-coumaric acid or sal- proliferation of human squamous cell carcinoma cells via necroptosis. Nutrition and
icylic acid also showed synergistic effect. However, salicylic acid or p- Cancer, 65, 1093–1097.
Bakir, S., Toydemir, G., Boyacioglu, D., Beekwilder, J., & Capanoglu, E. (2016). Fruit
hydroxybenzoic acid with protocatechuic acid or dihydro ferulic acid antioxidants during vinegar processing: Changes in content and in vitro bio-accessi-
exhibited antagonistic effect. In addition, we did some experiments to bility. International Journal of Molecular Sciences, 17, 1658.
investigate the interactions among organic acids, amino acids and Barnaba, C., Dellacassa, E., Nicolini, G., Nardin, T., Malacarne, M., & Larcher, R. (2015).
Identification and quantification of 56 targeted phenols in wines, spirits, and vinegars
phenolic compounds in Zhenjiang aromatic vinegar. The results suggest by online solid-phase extraction-ultrahigh-performance liquid chromatography-
that amino acids have a synergistic effect on the antioxidant activity of quadrupole-orbitrap mass spectrometry. Journal of Chromatography A, 1423,
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Ethics statement
of the main organic components of vinegars by high resolution 1H NMR spectroscopy.
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Constituents, sources, and formation mechanisms. Comprehensive Reviews in Food
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Journal of Functional Foods: Ting Xia, Bo Zhang, Wenhui Duan, Jin Zhang, Min Wang

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Journal of Functional Foods

Nutrients and bioactive components from vinegar: A fermented and

Fig. 1. The production progress of vinegars.

Represents unknown main materials and fermentation techniques.

Represents unknown main materials and fermentation techniques.

Represents unknown main materials and fermentation techniques.

Represents unknown main materials and fermentation techniques.

Represents unknown main materials and fermentation techniques.

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