Natural Product Research

Formerly Natural Product Letters

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Comparative studies of bioactive organosulphur

compounds and antioxidant activities in garlic
(Allium sativum L.), elephant garlic (Allium
ampeloprasum L.) and onion (Allium cepa L.)

Sunyoung Kim, Dan-Bi Kim, Wenjie Jin, Junghyuck Park, Wonjin Yoon,
Yunyeol Lee, Soyoung Kim, Sanghee Lee, Sungsoo Kim, Ok-Hwan Lee,
Dongbin Shin & Miyoung Yoo

To cite this article: Sunyoung Kim, Dan-Bi Kim, Wenjie Jin, Junghyuck Park, Wonjin Yoon,
Yunyeol Lee, Soyoung Kim, Sanghee Lee, Sungsoo Kim, Ok-Hwan Lee, Dongbin Shin & Miyoung
Yoo (2018) Comparative studies of bioactive organosulphur compounds and antioxidant activities
in garlic (Allium sativum L.), elephant garlic (Allium ampeloprasum L.) and onion (Allium cepa L.),
Natural Product Research, 32:10, 1193-1197, DOI: 10.1080/14786419.2017.1323211

To link to this article: https://doi.org/10.1080/14786419.2017.1323211

View supplementary material Published online: 05 May 2017.

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Natural Product Research, 2018
VOL. 32, NO. 10, 1193–1197
https://doi.org/10.1080/14786419.2017.1323211

SHORT COMMUNICATION

Comparative studies of bioactive organosulphur compounds

and antioxidant activities in garlic (Allium sativum L.),
elephant garlic (Allium ampeloprasum L.) and onion (Allium
cepa L.)
Sunyoung Kima1, Dan-Bi Kima1, Wenjie Jina, Junghyuck Parka, Wonjin Yoona,
Yunyeol Leea, Soyoung Kima, Sanghee Leea, Sungsoo Kima, Ok-Hwan Leeb,
Dongbin Shina and Miyoung Yooa
a
Food Analysis Center, Korea Food Research Institute, Seongnam, Republic of Korea; bDepartment of Food
Science of Biotechnology, Kangwon National University, Chuncheon, Republic of Korea

ABSTRACT ARTICLE HISTORY

We evaluated organosulphur compounds in Allium vegetables, Received 10 February 2017
including garlic, elephant garlic and onion, using high-performance Accepted 18 April 2017
liquid chromatography. Among organosulphur compounds, elephant
KEYWORDS
garlic had considerable γ-glutamyl peptides, and garlic had the highest Allium vegetable;
alliin content. Onion had low level of organosulphur compounds than organosulphur compounds;
did elephant garlic and garlic. In addition, antioxidant capacities antioxidant activity
were evaluated by oxygen radical absorbance capacity (ORAC)
values and 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis(3-
ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical scavenging
assay. The results showed that garlic had the highest antioxidant
capacity, followed by elephant garlic and onion. Furthermore, a
positive correlation was observed between antioxidant activities and
organosulphur compounds (R > 0.77). Therefore, our results indicate
that there was a close relationship between antioxidant capacity and
organosulphur compounds in Allium vegetables.

CONTACT  Miyoung Yoo  myyoo@kfri.re.kr

1
These authors contributed equally to this work.
 Supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2017.1323211.
© 2017 Informa UK Limited, trading as Taylor & Francis Group
1194   S. KIM ET AL.

1. Introduction
Oxidative stress, arising as a result of an imbalance between free radicals and antioxidant
defence, plays an important role in health (Halliwell & Gutteridge 1999). Abundant evidence
suggesting an association between oxidative stress in aging and the pathogenesis of various
diseases has facilitated additional studies of the roles of antioxidants in the treatment and
prevention of human disease (Prior & Cao 2000; Fang et al. 2002).
Allium vegetables impact health through lipid-lowering, anti-asthmatic, antidiabetic,
anticancer, antiplatelet and anti-atherosclerotic activities (Keusgen 2002). The many
biological effects of Allium vegetables are mainly associated with organosulphur compounds.
These compounds include four γ-glutamyl peptides: γ-l-glutamyl-S-allyl-l-cysteine (GSAC),
γ-l-glutamyl-S-(trans-1-propenyl)-l-cysteine (GSPC), γ-l-glutamyl-S-methyl-l-cysteine
(GSMC) and γ-glutamyl phenylalanine (γGPA). In addition, intermediate compounds in the
biosynthesis of S-alk(en)yl-l-cysteine sulphoxides (ACSOs) from γ-glutamyl peptides consist
of S-alk(en)yl-cysteines such as (+)-S-allyl-l-cysteine (SAC) and (+)-S-(trans-1-propenyl)-l-
cysteine (SPC). The corresponding ACSOs produced are (+)-S-allyl-l-cysteine sulphoxide
(alliin), (+)-S-(trans-1-propenyl)-l-cysteine sulphoxide (isoalliin) and (+)-S-methyl-l-cysteine
sulphoxide (methiin) (Iciek et al. 2009; Beato et al. 2012).
Previous studies have reported the quantification of bioactive sulphur compounds and
their physicochemical characteristics in Allium vegetables. For example, Fang et al. (2017)
reported a new phenylpropanoid glucoside and a chain compound from the roots of Allium
tuberosum. Additionally, Tan et al. (2015) investigated the structural properties of γ-­glutamyl-
S-allyl-cysteine peptide isolated from fresh garlic scales (Allium sativum L.). Also, Kim
et al. (2016) reported profiling of organosulfur compounds and antioxidant activities in
Allium hookeri. In addition, many studies have evaluated the antioxidant effects of Allium
vegetables using radical scavenging assays (Chu et al. 2000; Tepe et al. 2005). Although some
studies have assessed correlations between the antioxidant activities and bioactive com-
pounds, these studies have focused mainly on polyphenol (Yin et al. 2002; Prakash et al.
2007; Bozin et al. 2008; Santas et al. 2008). Moreover, although some researchers have shown
that organosulphur compounds are responsible for the antioxidant activities (Kourounakis
& Rekka 1991; Rekka & Kourounakis 1994; Prasad et al. 1995), few studies have evaluated
the relationship between antioxidant and organosulphur compounds in Allium vegetables.
Therefore, additional studies are needed to determine the effects of organosulphur com-
pounds on antioxidant activities in Allium vegetables.
Accordingly, the objective of this study was to assess organosulphur compounds in dif-
ferent three Allium vegetables, including garlic, elephant garlic, and onion, and to evaluate
their antioxidant activities using radical scavenging assays. Furthermore, we determined the
correlations between antioxidant activities and organosulphur compounds in Allium
vegetables.

2.  Results and discussion

2.1.  Determination of bioactive organosulphur compounds
The biological effects of Allium vegetables are thought to be associated to the presence of
organosulphur compounds. Therefore, we examined organosulphur compounds contents
of the three Allium vegetables (Table S1). Both garlic and elephant garlic had significantly
 NATURAL PRODUCT RESEARCH   1195

high level of γ-glutamyl peptides. In particular, the elephant garlic had higher GSPC content
than the other species. Some of the most important organosulphur compounds are ACSOs,
which are responsible for the pungent aroma and taste of vegetables (Rahman 2003). Alliin
and allicin, which are characteristic organosulphur compounds in garlic, were present at
concentrations of 23.63 and 5.58 mg/g dw, respectively. Elephant garlic also contained alliin
(2.61 mg/g dw) and allicin (0.43 mg/g dw), but at levels lower than those of garlic. Among
ACSOs, the isoalliin content ranged from 8.42 to 0.18 mg/g dw, and the highest level was
found in onion followed by those in garlic and elephant garlic. The levels of methiin and
cycloalliin were 0.32–1.27 and 1.32–2.21 mg/g dw, respectively. Thus, these results showed
the contents of organosulphur compounds varied among the three Allium vegetables. These
differences may be related to variations in cultivation and storage conditions (Lawson et al.
1991). Furthermore, when Allium vegetables are cut or crushed for organosulphur com-
pounds analysis, ACSOs are cleaved by cysteine sulphoxidelyase to produce corresponding
alk(en)ylsulphenic acid, which is then transformed into thiosulphinates (Stoll & Seebeck
1951). Thus, the sample conditions during the experiment will also affect the contents of
organosulphur compounds.

2.2.  Antioxidant activities

Antioxidant potentials of the three Allium vegetables were determined by oxygen radical
absorbance capacity (ORAC) values and 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azin-
obis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical scavenging activities. As shown
in Figure S1, garlic had markedly higher DPPH and ABTS radical scavenging activities than
elephant garlic and onion. Conversely, the ORAC value of elephant garlic was much higher
than those of the other Allium vegetables; specifically, elephant garlic had an ORAC value
that was approximately four times higher than that of onion. In a similar study by Moreno
et al. (2006), garlic was found to have a higher ORAC value than onion. Onion was shown to
be more effective than elephant garlic with regard to ABTS radical scavenging activity. The
reaction mechanism of antioxidant activity differed for ORAC, DPPH and ABTS assays. In
addition, the efficacy of scavenging free radicals for the same antioxidants differed (Niki
2010). Our findings are in agreement with those of Dudonne et al. (2009), who reported that
30 plant extracts of industrial interest showed different antioxidant activities with various
reaction mechanisms. Therefore, antioxidant profiles must be based on a variety of types of
antioxidant activities because reactive oxygen species are formed by a number of different
mechanisms and can be determined by a variety of techniques.

2.3.  Correlation between antioxidant activities and bioactive organosulphur

compounds
Many researches have evaluated the relationships between antioxidant activities and bio-
active compounds in Allium vegetables. In particular, phenolic and flavonoid compounds
are responsible for antioxidant activities (Fei et al. 2015; Onyeoziri et al. 2016). In this study,
we investigated whether organosulphur compounds were correlated with antioxidant activ-
ities, using ORAC, DPPH and ABTS assays. Our results showed that organosulphur compounds
were positive correlated with antioxidant activities by ORAC (R = 0.89) and DPPH (R = 0.77)
assay (Figure S2). Several studies have been reported the antioxidant activities of organo-
1196   S. KIM ET AL.

sulphur compounds in Allium vegetables (Yin & Cheng 1998; Wu et al. 2001; Yin
et al. 2002), including those of alliin and allicin (Chung 2006). Therefore, garlic has a relatively
higher antioxidant activity than elephant garlic and onion. Although onion was found to
have considerably lower concentrations of organosulphur compounds than elephant garlic
and garlic, antioxidant activity was still observed. This result could be explained by the high
contents of ascorbic acid, which has been shown to have antioxidant activity in onion
(Pantelidis et al. 2007). Therefore, the results of our study explain the positive relationship
between antioxidant activity and organosulphur compounds in different Allium vegetables.
However, further studies are needed to assess the antioxidant activities of individual orga-
nosulphur compounds using various radical scavenging assays.

3. Conclusion
This study was intended to assess and compare organosulphur compounds and antioxidant
activities of three Allium vegetables. Eleven organosulphur compounds were simultaneously
analysed using an HPLC-PDA system, and their contents were found to be significantly dif-
ferent among the three Allium vegetables. In addition, the antioxidant activities were eval-
uated by ORAC, DPPH and ABTS assay. As a result, we found that the antioxidant activity of
garlic was the highest when measured by ABTS and DPPH assays, whereas that of elephant
garlic was the highest when measured by ORAC assay. Taken together, our findings demon-
strated that there was a positive correlation between antioxidant activity and organosulphur
compounds. These results could be used to elucidate the relationships between organosul-
phur compounds and antioxidant content and for the development of Allium vegetable-
derived functional foods.

Disclosure statement
No potential conflicts of interest were reported by the authors.

Funding
This work was supported by the Korea Food Research Institute [grant number E0133101], [grant
number E0156500-02].

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