Accepted Manuscript

Jackfruit (Artocarpus heterophyllus Lam.) peel: A better source of antioxidants

and a-glucosidase inhibitors than pulp, flake and seed, and phytochemical pro-
file by HPLC-QTOF-MS/MS

Lu Zhang, Zong-cai Tu, Xing Xie, Hui Wang, Hao Wang, Zhen-xing Wang,
Xiao-mei Sha, Yu Lu

PII: S0308-8146(17)30778-1
DOI: http://dx.doi.org/10.1016/j.foodchem.2017.05.003
Reference: FOCH 21063

To appear in: Food Chemistry

Received Date: 21 January 2017

Revised Date: 28 April 2017
Accepted Date: 1 May 2017

Please cite this article as: Zhang, L., Tu, Z-c., Xie, X., Wang, H., Wang, H., Wang, Z-x., Sha, X-m., Lu, Y., Jackfruit
(Artocarpus heterophyllus Lam.) peel: A better source of antioxidants and a-glucosidase inhibitors than pulp, flake
and seed, and phytochemical profile by HPLC-QTOF-MS/MS, Food Chemistry (2017), doi: http://dx.doi.org/
10.1016/j.foodchem.2017.05.003

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 Jackfruit (Artocarpus heterophyllus Lam.) peel: A better source of

antioxidants and a-glucosidase inhibitors than pulp, flake and seed,

and phytochemical profile by HPLC-QTOF-MS/MS

Running tittle: Bio-activities and phytochemical identification of jackfruit peel

Lu Zhang a, Zong-cai Tu a,b,*, Xing Xie b , Hui Wang b,*, Hao Wang a, Zhen-xing Wang a,

Xiao-mei Sha a, Yu Lu a

a
Key Laboratory of Functional Small Organic Molecule, Ministry of Education and College of

Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, China

b
State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang

330047, China

*Corresponding authors:

Prof. Zong-cai Tu

99 Ziyang Road, New and High-tech Development Zone, Nanchang, Jiangxi, China

Fax: +86-791-8812-1868

Phone number: +86-791-8830-5938

E-mail: [email protected] (Zong-cai Tu)

1
ABSTRACT

Jackfruit (Artocarpus heterophyllus Lam.) peel is an underutilized by-product in both, the

production and processing of jackfruit. This research compared the antioxidant and hypoglycemic

potential of jackfruit peel with jackfruit pulp, flake and seed for the first time. The phytochemical

profile of peel extract was characterized with HPLC-QTOF-MS/MS. Results revealed that peel extract

exhibited the highest total phenolic and total flavonoid content, and the phenolics was 4.65, 4.12 and

4.95 times higher than that of pulp, flake and seed extract, respectively. The strongest DPPH· and

ABTS+· scavenging ability, α-glucosidase inhibition were also found in peel extract, and the

α-glucosidase inhibition was about 11.8 fold of that of acarbose. The HPLC-QTOF-MS/MS analysis

led to the tentative identification of 53 compounds, prenylflavonoids, hydroxycinnamic acids and

glycosides are the predominant bioactive compounds. Above results reveal promising potential of

jackfruit peel as a new source of natural antioxidants and hypoglycemic agents.

Keywords: Jackfruit peel, antioxidant, a-glucosidase inhibition, phytochemical identification,

HPLC-QTOF-MS/MS

1. Introduction

Diabetes mellitus is a metabolize disease characterized by high blood glucose level, which has been

one of the major causes of death in people younger than 60 years. It is predicted that over 552 million

people will suffer from diabetes by the year 2030 (Whiting, Guariguata, Weil, & Shaw, 2011).

Individuals with diabetes are more easy to suffer from many chronic diseases, such as atherosclerosis,

retinopathy, kidney disease, alzheimer’s disease, vascular dementia and congestive heart failure

(Kaneto, Katakami, Matsuhisa, & Matsuoka, 2010; Peila, Rodriguez, & Launer, 2002; Stratton, et al.,

2000 and Wanner, et al., 2016).

2
 Reactive oxygen species (ROS) are normal metabolites of human body, but over production of

ROS will cause the damage of protein, DNA, and other macro-molecules of living cells. Sometimes, it

will induce a series of chronic diseases, such as cardiovascular disease, immune-system decline,

diabetes, aging, cancer and brain dysfunction (Ames, Shigenaga, & Hagen, 1993 and Halliwell, 1991).

In addition, it can contribute to the development of diabetic complication (Kaneto, et al., 2010).

Therefore, exploration of effectively natural antioxidants without side-effects has been a hotspot in the

area of cosmetic, pharmaceutical and natural food supplements markets.

Artocarpus heterophyllus L. (Jackfruit) is a large evergreen tree belonging to Moraceae. It is

indigenous to India and widely grows in Malaysia, Sri Lanka, India, Philippines, Burma, Indonesia,

Pakistan and China, et al. It is a high yielding crop bearing fruit all year round with peak production

on June and December. Its leaf and root have been used for wound healing, treating dermatosis,

anemia, diarrhea and asthma (Baliga, Shivashankara, Haniadka, Dsouza, & Bhat, 2011 and Cardozo

Junior & Morand, 2016). Until now, some phytochemical and pharmacological studies have been

performed on jackfruit pulp, leaf, root and bark (Baliga, et al., 2011). Extracts of jackfruit pulp show

considerable anti-inflammatory activity by suppressing the production of nitric oxide (NO) and

prostaglandin E2 (PGE2) (Fang, Hsu, & Yen, 2008), its leaf extracts also give remarkable antioxidant

activity and exhibit attenuation on hyperglycemia and hyperlipidemia (Omar, El-Beshbishy, Moussa, Taha,

& Singab, 2011). Its wood was reported to be used as antioxidant, anti-aging, anti-inflammatory and

skin-care agents (Nguyen, Nguyen, Nguyen, Bui, & Nguyen, 2012). The leaf, root, bark and fresh fruit of

this plant have been certified to contain various compounds like flavonoids, phenolic acids, organic

acids, carotenoids, stilbenes, triterpenes, and sterols, especially for prenylflavonoids (Arung, Yoshikawa,

Shimizu, & Kondo, 2010; Baliga, et al., 2011 and de Faria, de Rosso, & Mercadante, 2009).

3
 The whole jackfruit is consisted of fruit axis (core of the fruit), pulp (the middle fleshy edible bulb),

flake (the outer packaged silk-like part of pulps) and peel (the outer horny and non-edible part).

Expect for the fruit axis and peel, jackfruit is not only consumed as a fresh fruit when ripe but also

used as a vegetable in the unripe stage (Ong, et al., 2006). The pulps are also processed into fruit

snack, fruit juice and fruit wine, et al. Whereas, the peel which forms about 46% of the fruit is

underutilized, and is mainly discarded as waste or fertilizer (Ding & Ming, 2009). In addition, research on

the phytochemical constituents and bio-activity of jackfruit peel is also unavailable. To clarify the

application potential and developmental value, it is of paramount importance to understand the

phytochemical constituents and biological activity of jackfruit peel.

In this work, the content of polyphenols, antioxidant and hypoglycemic activity of jackfruit peel

extract were evaluated by comparing with that of jackfruit pulp, flake and seed. The antioxidant

activity was investigated by DPPH and ABTS radical scavenging ability assay, the hypoglycemic

activity was studied through the inhibition on the activity of a-glucosidase. A comprehensively

qualitative characterization of the phytochemical profile in jackfruit peel extract was performed

through high performance liquid chromatography electrospray ionization quadruple time-of-flight

tandem mass spectrometry (HPLC-ESI-QTOF-MS/MS).

2. Materials and Methods

2.1. Materials and chemicals

Three fresh Malaysia No.1 jackfruits (about 10 kg for each) were purchased from Sanya, Hainan on

29th Aug. 2015. The peel, pulp, flake and seed were manually separated from fresh ripe jackfruits. All

parts were then freeze-dried, pulverized into fine powder and stored at -4 oC.

4
 p-Nitrophenyl-α-D-glucopyranoside, α-glucosidase (yeast, EC 3.2.1.20) and acarbose, 1,1-dipheny

-l,2-picryl hydrazyl (DPPH), 2,2’-azino-bis (3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) were

purchased from Sigma-Aldrich (St. Louis, MO, USA). Acetonitrile and formic acid were HPLC grade

and purchased from Merck (New York, USA). Ultra-pure water was prepared with Millipore water

purification system (Massachusetts, USA). All other used reagents were analytical grade and

purchased from Aladdin (Shanghai, China).

2.2. Extraction of phytochemical compounds

The pulverized jackfruit samples (2.0 g) were dispersed in 60 mL of 90% methanol at a solid/liquid

ratio of 1:30 (g/mL), and extracted at room temperature for 6 h in a shaker at 100 rpm, following by

centrifugation at 4000 rpm for 8 min. The residues were re-extracted under the same conditions twice,

then the supernatants were combined, filtered, evaporated in vacuum and made to 50 mL with 90%

methanol.

2.3. Analysis of total phenolic and total flavonoid content

The total phenolic content in jackfruit extracts was tested by the Folin-Ciocalteau method as

previously reported (Zhang, Tu, Yuan, Wang, Xie, & Fu, 2016). Gallic acid was used as standard, total

phenolic content was expressed as mg of gallic acid equivalents per gram of dry materials (mg GAE/g

DM). Experiments were done in triplicate.

Total flavonoid content was determined using the AlCl3 colorimetric method following the same

procedures described in Zhang, et al. (2016). The total flavonoid content was calculated from a

calibration curve plotted with quercetin as standard, and expressed as mg of quercetin equivalents per

gram of dry materials (mg QuE/g DM). Experiments were done in triplicate.

5
2.4. Antioxidant activities

The DPPH· and ABTS+· scavenging abilities were performed to compare the antioxidant activity of

jackfruit peel, flesh, flake and seed. The DPPH· scavenging ability was evaluated by mixing 50 µL of

sample (156.25 µg/mL~10 mg/mL) with 200 µL of 0.15 mM DPPH methanol solution in a 96-well

micro-plate following the procedures described previously (Zhang, et al., 2016). In case of

ABTS+· scavenging ability, ABTS+· stocking solution containing 7 mM ABTS and 2.45 mM

potassium persulfate was prepared with distilled water, it was then allowed to react for 12 ~ 16 h in

darkness. Before use, the stocking solution was diluted with methanol to an absorbance of 0.7 ± 0.2 at

734 nm. Then, the ABTS+· scavenging ability was measured by mixing 50 µL sample solutions

(156.25 µg/mL~10 mg/mL) with 200 µL diluted ABTS+· solution in a 96-well micro-plate (Zhang, et

al., 2015). Finally, absorbance at 734 nm was measured after 6 min of incubation at room temperature.

BHT was used as positive control. The IC50 value, the sample concentration required to scavenge 50%

of free radical, was calculated by nonlinear curve fitting with Origin 8.0 (OriginLab Co., US), and

expressed as milligram of dried materials per milliliter (mg DM/mL). All tests were performed in

triplicate.

2.5. a-glucosidase inhibitory activity

a-Glucosidase inhibitors are generally recommended as effective approaches for managing the

fasting and postprandial blood glucose levels (Kalra, 2014). Therefore, a-glucosidase inhibitory assay

was carried out to compare the anti-hyperglycemic effect of different parts of jackfruit (Zhang, et al.,

2016). Diluted samples or acarbose at various concentrations (50 µL) were mixed with 50 µL of PBS

(0.1 M, pH 6.9) and 100 µL of 0.1 U/mL α-glucosidase solution (in 0.1 M, pH 6.9 PBS). After 10 min

of reaction at 25 oC in 96-well micro-plate, 50 µL of 5 mM pNPG solution (in 0.1 M, pH 6.9 PBS)

6
was added. The mixture was allowed to incubate at 25 oC for 5 min, following by the measurement of

absorbance at 405 nm using a Synerg H1 micro-plate reader (Biotek, Vermont, USA). Control group

with 50 µL of methanol replace samples or standard and blank group with 100 µL of PBS replace

α-glucosidase solution were run in parallel.

2.6. Identification of phytochemical profiles

2.6.1 Liquid chromatographic analysis

Chromatographic separation of compounds in jackfruit peel extract was performed on an Agilent

1290 UPLC system coupled to an auto-sampler, a DAD detector and an Agilent ZORBAX SB-C18

column (250 mm × 4.6 mm, 5 µm) (Agilent Technologies, Santa Clara, USA). Ultra-pure water

containing 0.1% formic acid and acetonitrile were used as mobile phases A and B, respectively, at a

flow rate of 0.8 mL/min. The extract was eluted with an optimum gradient program as following: 0

min, 8% B; 10 min, 12% B; 22 min, 19% B; 35 min, 30% B; 38 min, 40% B; 40 min, 72% B; 45 min,

75% B; 48 min, 90% B, following by washing with 100% B for 6 min. The column was then

re-equilibrated with 8% B for 15 min prior to next injection. All extracts were filtered through 0.22

µm PTFE filter before analysis. The injection volume was 10 µL.

2.6.2. HPLC-QTOF-MS/MS analysis

Phytochemical profile was identified using an Agilent Technologies 6530 OHD Accurate-Mass

Q-TOF MS/MS system (Agilent Technologies, CA, Santa Clara, USA) equipped with an Agilent 1290

UPLC system and an ESI source. Full automatic acquisition fragmentation pattern under negative

mode was performed following the same operation parameters given in Zhang et al. (2016). The

parameters for chromatographic separation was the same as that described in section 2.6.1. Automatic

MS/MS experiment was performed by adjusting the collision energy as follows: m/z < 200, 10, 20 eV;

7
m/z 200 ~ 400, 20, 30 eV; m/z 400 ~ 600, 30, 40 eV; m/z > 600, 40, 50 eV; m/z > 700, 40, 50, 60 eV.

The MS data were processed with MassHunter software (Agilent Technologies, CA, Santa Clara,

USA), possible molecular formula of each precursor and product ion was calculated by using the

Generate Molecular Formula™ editor. Identification of each compounds was carried out by analyzing

the precursor ion, molecular weight, fragmentation pattern, retention time, and by matching these data

with that reported in available references.

2.7. Statistical analysis

All experiments were carried out in triplicate, results were presented as mean value ± standard

deviation. Statistical analysis of the results was done with the SPSS 13.0 (Chicago, IL) at a level of p

< 0.05 on one-way analysis of variance and Duncan’s multiple range analysis. Pearson correlation was

carried out to analyze the correlation coefficients between the content of polyphenols and

bio-activities. The IC50 values for antioxidant activity and enzyme inhibition were calculated with

Origin 8.0 (OriginLab Co., USA) through nonlinear polynomial fit of the curve plotted with sample

concentration versus percentage inhibition.

3. Results and discussion

3.1. Determination of total phenolic and total flavonoid content

Polyphenols are the major bio-active constituents present in plant materials. Thus, the total phenolic

and total flavonoid content in extracts from different parts of jackfruit were determined. As shown in

Table 1, peel extract exhibited the highest total phenolic content, extract from fruit flake ranked to the

second, with the values of 48.04 and 11.57 mg GAE/g DM, respectively. Whereas, the lowest total

phenolic content was detected in pulp and seed extracts, which was only about 20.2% of that of peel

8
extract, and no significant difference was observed (p > 0.05).

The total flavonoid content was also varied in different extracts. The highest total flavonoid content

of 2.79 mg QuE/g DM was found in peel extract, followed by pulp and flake extracts (p > 0.05).

Similarly, seed extract gave the lowest total flavonoid content (1.62 mg QuE/g DM). Above results

indicated that the peel of jackfruit is a better source of polyphenols than jackfruit pulp, flake and seed

since it is richer in polyphenols. This could be that the peel is exposed to the external environment,

which is more prone to undergo abiotic stressful conditions that may promote the synthetic and

accumulation of polyphenols, such as sun light, ultraviolet radiation, high temperature, insect and

desiccation, et al. (Feng, Luo, Zhang, Zhong, & Lu, 2014 and Lopes, et al., 2016). Richer content in

phenolics and flavonoids in the rind or peel of fruits or vegetables has also been found by many other

researches. The rind of sugarcane give the highest total phenolic and total flavonoid content, and they

were about 2.95~1.65 and 3.88~2.10 fold higher than that of pith, node and tip, respectively (Feng, et

al., 2014). Alessandra Masci et al. (2016) found that the extract of pomegranate peel exhibited much

higher total phenolic and total flavonoid content than whole fruit extracts. Silva et al. (2004) also

indicated that quince fruit peel gave much higher phenolics and flavonoids than pulp and seed. The

detected content of phenolics and flavonoids in jackfruit pulp extract are much higher than what

reported by Jagtap et al. (2010), but the total flavonoid content found in seed extract is far below the

value measured by Gupta et al. (2011). These could be due to the difference in determination method,

variety and growth environment of jackfruit, as well as in the method of sample preparation.

3.2. In vitro antioxidant activity

The antioxidant activity of extracts from jackfruit peel, pulp, flake and seed was tested by

DPPH· and ABTS+· scavenging ability assays. The results are shown in Fig.1, the IC50 values of

9
samples expressed as mg dry matter per milliliter of extract solution (mg DM/mL) were given in

Table 1. In case of ABTS+· scavenging ability (Fig.1A), all samples exhibited an obvious

dose-dependent relationship. But peel extract yielded much higher ABTS+· scavenging ability than

pulp, flake and seed extracts, with the IC50 values of 0.23, 5.7, 8.21 and 7.62 mg DM/mL, respectively.

Therefore, the total antioxidant ability of jackfruit peel extract was about 24.8 and 33.1 fold of that of

pulp and seed extract, respectively, when compared with the IC50 values. However, the total

antioxidant ability of peel extract was significantly lower than positive control BHT (IC50 value of

0.02 mg/mL).

For DPPH· scavenging ability, only peel extract yielded a dose-dependent response with the

increasing of sample concentration, the percentage inhibition was improved from 16.7% at 0.16 mg

DM/mL to 69.4% at 2.5 mg DM/mL. But, the other extracts gave ignorable DPPH· scavenging ability

with the inhibition from 2.57% to 22.35% at the concentration range of 0.16 ~ 10 mg DM/mL.

Obviously, peel extract presented the highest DPPH· scavenging ability with the IC50 value of 1.25

mg DM/mL, whereas the activity was lower than synthetic antioxidant BHT (IC50 value of 0.3 mg/mL)

when compared in term of the mass of dry material but not extract. Silva et al. (2004) found that the

methanol extract of quince peel showed the strongest antioxidant activity, followed by pulp and seed

extracts. The DPPH· scavenging ability and ferric reducing antioxidant power of bambangan peel is

about 2 times of that of flesh (Abu Bakar, Mohamed, Rahmat, & Fry, 2009). The rind extracts of red

and green sugarcane both exhibit the strongest antioxidant activity, which were about 2.19 ~ 5.47 and

2.60 ~ 7.82 times of that of pith, node and tip extracts from red and sugar sugarcane, respectively

(Feng, et al., 2014).

Correlation analysis revealed the correlation coefficients between ABTS+· scavenging ability and

10
total phenolic and total flavonoid content of -0.942 and -0.732, respectively, indicating that both

phenolics and flavonoids are major antioxidant compounds presented in jackfruit, and phenolics

contribute more to the observed antioxidant activity. But correlation between the DPPH· scavenging

ability and content of phenolics and flavonoids was not detected due to the lack of IC50 value. High

correlation with phenolics was also found by Silva et al. (2004) and Abu Bakar et al. (2009) with

quince and bambangan as material, respectively. Therefore, the strongest in vitro antioxidant activity

detected in jackfruit peel extract can be explained by its highest total phenolic and total flavonoid

content (Table 1).

3.3. a-Glucosidase inhibitory activity

a-Glucosidase inhibitors (AGIs) is an effective approach for controlling the postprandial and

fasting blood glucose levels (Kumar, Narwal, Kumar, & Prakash, 2011), but randomized controlled

trials revealed that the clinical glucosidase inhibitors, acarbose and miglitol, possess many

gastrointestinal side effects on diabetics, producing flatulence, diarrhoea, borborygmus, abdominal

pain and distension (Chiasson, Josse, Gomis, Hanefeld, Karasik, & Laakso, 2002). So, plant based

natural AGIs are becoming growing attractive to researchers and consumers due to their low cost and

relatively higher safety. The a-glucosidase inhibition of jackfruit peel, pulp, fruit flake and seed are

shown in Fig.1C and Table 1, all extracts were capable of inhibiting the activity of a-glucosidase in a

concentration-dependent manner, and the inhibition followed the pattern of peel extract > seed

extract > pulp extract > flake extract. It is interesting to find that the highest inhibition was observed

in peel extract with the lowest IC50 value of 0.05 mg DM/mL, which was 10.8 times higher than

positive control acarbose ( IC50 = 0.59 mg DM/mL). This indicated that jackfruit peel can be a

promising source of effectively natural AGIs. Contrary to the in vitro antioxidant activities, correlation

11
analysis revealed that the a-glucosidase inhibition was moderately correlated with total phenolics

content (r = -0.621), however, no correlation was observed between a-glucosidase inhibition and total

flavonoids content (r = -0.28). It could be speculated that phenolics are one of the major AGIs

presented in jackfruit peel, and there are other class of compounds contribute to the detected activity

of pulp and seed.

3.4. HPLC-QTOF-MS/MS identification

The phytochemical profile of jackfruit peel extract was characterized by using

HPLC-QTOF-MS/MS to explore the possible functional compounds present in jackfruit peel. The

total ion chromatogram of peel extract obtained by full scan mode under negative ion is shown in

Fig.2. The targeted analytes were identified or tentatively identified mainly by interpreting their

elution order, accurate mass, fragmentation patterns, and the molecular formula of deprotonated

molecule and predominant product ions. Comparison of obtained MS and MS/MS data with

compounds previously identified in literatures or that recorded in Metlin and Massbank provided a

tentatively identification. Meanwhile, reported phytochemical information from other parts of

jackfruit and Artocarpus genus were used as an indicative information to assist the identification of

compounds due to the analogue of compound composition of plant belonging to the same species and

genus. All information needed for compounds assignment was summarized in Table 2, a total of 53

compounds belonging to different classes were tentatively identified, including 8 organic acids, 8

glycosides, 12 phenolic acids, 18 flavonoids, 3 oxylipins and 4 other compounds.

3.4.1. Organic acids

The fragmentation patterns of organic acids generated mainly fragments of [M-CO2]-, [M-H2O]-,

12
[M-H2O-CO2]- and [M-H2O-CO]-. A neutral loss of 162 Da and132 Da can also be detected when the

organic acid is glycosylated with hexose or pentose. In this research, 8 organic acids were found in

jackfruit peel extract. Peaks 2 ~ 5 was identified as quinic acid, malic acid, quinic acid isomers and

citric acid, respectively, by matching their deprotonated molecular ion, molecular formula and

fragments with that reported in references (Morales-Soto, Gómez-Caravaca, García-Salas,

Segura-Carretero, & Fernández-Gutiérrez, 2013; Sun, et al., 2015). Peaks 1, 7 and 21 was tentatively

identified as naphthalenedicarboxylic acid-O-hexose, resorcylic acid-O-hexose and hydroxycaproic

acid-O-hexose, respectively. Characteristic product ions at 215.0331 (C12H8O4), 153.0193 (C7H6O4),

and 131.0711 (C6H12O3) corresponded to the moiety of naphthalenedicarboxylic acid, resorcylic acid

and hydroxycaproic acid, respectively, resulting from the neutral loss of a hexose (162 Da). Peak 6

yielded [M-H]- at m/z 368.1001 (C16H19NO9), MS/MS fragmentation ion at m/z 144.0455 (C9H6NO)

resulted from the successive loss of a hexose (180 Da) and a CO2 (44 Da) unit. Product ions at

119.0346 (C4H8O4 ), 89.0245 (C3H6O3) and 71.0149 (C3H4O2) presented the typical fragmentation

pattern of hexose. Thus, peak 6 was tentatively proposed as [5-glucopyranosyloxy-2-oxo-2,3-dihydro

-1H-indol-3-yl] acetic acid, the possible fragmentation pattern was given in Fig.3A.

3.4.2. Glycosides

Interesting, eight glycosides were tentatively identified, including digitoxosylhexoside (8), three

pentyl-pentosylhexosides (30, 31, and 32), benzyl-pentosylhexoside (26), benzyl-acetylpentosyl

-hexoside (33), pentyl-dipentosylglucuronide-hexoside (35) and pentyl-acetylpentosylhexoside (36).

The MS/MS spectra of alcohol glycosides were characterized by the presence of diagnostic

fragmentation pattern of hexose and the neutral loss of 132 Da, which produced common or similar

MS/MS ions at 161.05 [hexosyl-H]-, 131.04 [pentosyl-H]- or [hexosyl-CH2O-H]-, 113.02

13
[hexosyl-CH2O-H2 O-H]- or [pentosyl-H2 O-H]- and 101.02 [hexosyl-2CH2O-H]-. Acetylpentosyl

-hexoside showed typical connective breakage of acetyl and pentosyl, giving a loss of molecular

weight of 42 Da and 42+132 Da, respectively. For, example, diagnostic ions at m/z 269.1041

(C13H18O6) and 161.0456 (C6H10O5) were observed in peak 26 (401.1460, C18H26O10), indicating the

loss of pentosyl (132 Da) and further loss of benzyl (C5H8O, 108 Da), then peak 26 was tentatively

identified as benzyl-pentosylhexoside. Peak 33 ( [M-H]-, 443.1575) was proposed as

benzyl-acetylpentosylhexoside, product ions at 401.1439 [M-C2H2 O-H]- and 269.1023

[M-C2H2O-pentosyl-H]- suggested the presence of acetyl, pentosyl and benzylhexoside units in parent

ion. Peaks 30, 31 and 32 presented the same [M-H]- (m/z 381.1780), molecular formula (C20H28O11)

and fragmentation pattern, MS/MS ions at 249.1332 and 161.0452 corresponded to the loss of

pentosyl (132 Da) and further breakage of pentyl group (88 Da), then they were tentatively assigned

as pentyl-pentosylhexosides. The detected fragmentation pattern of benzyl-pentosylhexoside is shown

in Fig.3B with benzyl 2-O-β-D-xylopyranosyl-β-D-glucopyranoside as example. Peak 8 showed

[M-H]- ion at 309.1191 and fragment ion at 161.0453 [hexosyl-H]- due to the loss of digitoxose (148

Da) was tentatively identified as digitoxosylhexoside.

3.4.3. Phenolic acids

A total of 9 hydroxycinnamic acids and 3 hydroxycoumarins were detected in sample, including 6

caffeoylquinic acid (CQA) isomers (9, 10, 20, 23, 24 and 27), a 3,4-dihydroxybenzoic acid methyl

ester-C-dihexoside (15), a feruloylglucose (17), a caffeoylglucose (22) and 3 esculetin glycosides (12,

14 and 16). The MS/MS spectra of caffeoylquinic acids (CQAs) under negative mode generally

produced characteristic product ions at m/z 191.06 (C7H12O6), 173.05 (C7H10O5), 179.0342 (C9H8O4)

and 135.0049 (C8H8O2), corresponding the fragments of [quinic acid-H]-, [quinic acid-H2O-H]-,

14
[caffeic acid-H]-, [caffeic acid-CO2-H]-, respectively (Ammar, del Mar Contreras, Belguith-Hadrich,

Segura-Carretero, & Bouaziz, 2015; Regos, Urbanella, & Treutter, 2009). According to the results of

Lin et al. (2008) and Regos et al. (2009), the elution order of CQAs on Agilent Zorbax column

follows the sequence of 1-CQA>3-CQA>5-CQA>4-CQA, and the retention time of cis structure is

shorter than that of trans structure. In addition, it was reported that the MS/MS spectra of CQAs with

m/z at 173 as base peak suggested the linkage of acyl groups to the 4-OH position, base peak at m/z

191 indicated that the acyl group is connected to the 3-OH or 5-OH position, but the simultaneous

occurrence of major ion at m/z 179 is more pronounced for 3-OH compounds (Gu, Yang, Abdulla, &

Aisa, 2012). On the basis of the elution behavior and hierarchical key of CQAs, peaks 9, 10, 20, 23,

24 and 27 were tentatively identified as cis 3-CQA, trans 3-CQA, cis 4-CQA, cis 5-CQA, trans

5-CQA and trans 4-CQA, respectively. Peaks 17 and 22 shared similar fragmentation behavior,

including neutral loss of glucosyl moiety and CO2 . They were proposed as feruloylglucose and

caffeoylglucose, respectively, due to their diagnostic fragment ions at 193.0504 [ferulic acid-H]- and

179.0342 [caffeic acid-H]-, which were in accordance with previous results of Jiménez-Sánchez et al.

(2016).

Diagnostic ions at m/z 177.02 and 133.03 were observed in peaks 12, 14 and 16, indicating the loss

of a hexosyl, a hexosyl and a hexosylpentose moiety, respectively, as well as further decarbonation. In

terms of peak 14, characteristic fragmentation pattern of C-glycoside was observed with MS/MS ions

at 219.0276 [M-120 Da-H]- and 189.0181 [M-150 Da-H]- (Waridel, Wolfender, Ndjoko, Hobby,

Major, & Hostettmann, 2001). Thus, peaks 12, 14 and 16 were individually proposed as

esculetin-O-hexoside, esculetin-C-hexoside and esculetin-O-hexoylpentoside (Abu-Reidah,

Ali-Shtayeh, Jamous, Arráez-Román, & Segura-Carretero, 2015 and Ammar, et al., 2015). The

15
fragmentation pattern of peak 14 was given in Fig. 3C with esculetin-5-C-glucoside as example.

Similar, peak 15 was assigned as 3,4-dihydroxybenzoic acid methyl ester-C-dihexoside due to the

characteristic fragmentation pattern of C-diglycoside and loss of methoxyl, two aldehyde groups and

decarbonation.

3.4.4. Flavonoids

Flavonoids were the dominant compounds presented in jackfruit peel extract, in this research, 18

flavonoids were found. Peaks 28, 29 and 37 were identified as aglycone of flavonoid, which generally

0,3
gave typical Ret-Diels-Alder (RDA) fragmentation yielding fragments at A-, 1,3A- , 1,4
A-, 2,4A-, 0,3 B-,

1,2
B- and 1,3
B-, meanwhile, dehydration and decarbonation of aglycone was also observed (Fabre,

Rustan, de Hoffmann, & Quetin-Leclercq, 2001). Peak 29 presented precursor ion at m/z 289.0728,

MS/MS ions at 245.0790, 205.0503 and 161.0595 corresponded to the connective loss of CO2, C3H4,

and CO2, respectively. Diagnostic ions at 137.0247, 125.0253, 121.0309 and 109.0303 corresponded

0,2
to the fragment of B-, 1,4
A-, 0,3
A-, and [B-ring-H]-, respectively. Then, peak 29 was tentatively

identified as (epi)catechin (Abu-Reidah, et al., 2015). The detailed fragmentation pattern of

(epi)catechin is shown in Fig.3D. Similarly, peaks 28 and 37 were assigned as dihydromyricetin and

dihydroquercetin (Ammar, et al., 2015), respectively. The fragmentation pattern of dihydromyricetin

is shown in Fig.4A. Peak 25 ([M-H]-, 435.1300, C21H24O10) produced a diagnostic ion at 271.0565

[M-rhamnose-H]-, suggesting the existence of a aglycone (Y0) with molecular formula of C15H14 O6

(289 Da) and the linkage of O-rhamnoside. The MS/MS spectrum of peak 13 presented a base peak at

289.0704 (C15 H14O6), then peaks 25 and 13 were tentatively identified as (epi)catechin-O-rhamnoside

and procyanidin B (Yan, Zhang, & Feng, 2016), respectively, due to the similar fragmentation pattern

of aglycone with peak 29.

16
 A typical MS/MS spectra of C-diglycoside was observed in peak 34, product ions at 417.1200,

387.1092, 357.0977, 345.0967 and 315.0882 corresponded to the fragment of [M-hexose-H]-,

[M-hexose-CH2O-H]-, [M-hexose-2CH2O-H]-, [M-hexosyl-3CH2O-H]-, and [M-hexosyl-4CH2O-H]-,

indicating the linkage of C-dihexoside, as well as the presence of aglycone (Y0) with molecular

weight at 273 Da [M-hexosyl-3CH2O-42 Da-H]- (Gu, et al., 2012 and Vukics & Guttman, 2010). Then

peak 34 was proposed as phloretin-C-dihexoside (Morales-Soto, et al., 2013), the fragmentation

pattern was given in Fig.3E.

Many prenylated flavonoids have been found from the root, leaf and wood of Artocarpus

heterophyllus Lam (Gupta, et al., 2011 and Nguyen, et al., 2012). In this research, eight

prenylflavonoids (44 ~ 47, 50 ~ 52 and 55), three pentenyl flavonoids (54, 56 and 62) and one

hexenylflavonoids (58) were found, which produced typical fragments resulted from the loss of C5H10,

whereas the co-existence of ions resulted from the loss of C2 H6 and C4H10 moiety is more pronounced

for pentenylflavonoids, and loss of C5 H10O indicated that the alkyl group locates on hydroxy. Peak 50

was characterized as Morachalcone A, which has been identified in the wood of Artocarpus

heterophyllus (Nguyen, et al., 2012), the fragmentation was given in Fig.4B. Whereas peak 51 was

assigned as Morachalcone A isomer due to the same parent ion and major fragmentation pattern with

peak 50. The molecular weight of peaks 54 and 62 ([M-H]-, 323.1289] showed 16 Da less than

Morachalcone A, but the MS/MS spectra both presented fragments resulting from the loss of C2H6,

C4H10, C5H10 and C5H10+CO, and peak 54 presented diagnostic ions at 203.0713 and 119.0504

corresponding to the cleavage of C7-C8 bond. Thus, peak 54 was tentatively identified as

pentenylisoliquiritigenin, and 62 was assigned to pentenyl-O-isoliquiritigenin due to the loss of

C5H10O. The fragmentation pattern of peak 54 was given in Fig.4C. By the same way, peaks 46 and

17
56 was proposed as prenyl-O-naringenin and pentenylnaringenin, respectively, peak 58 showed parent

ions at 339.1601 with corresponding molecular at C21H24O4 was tentatively proposed as

hexenyl-5,7,4'-trihydroxyflavan due to the RDA fragmentation pattern and loss of hexenyl unit

(135.0447, [1,3B-C6H12]-). The fragmentation pattern of peaks 46, 56 and 58 were given in Fig.4D, 4E

and Fig.4F, respectively. Peak 55 with parent ion at m/z 337.1082 was tentatively identified as

prenylgenistein according to reference (Ammar, et al., 2015). Other alkyl flavonoids were tentatively

identified by analysis the fragmentation pattern and by matching the product ions, molecular formula

and corresponding structures with that reported in references and recorded in Metlin, Scifinder and

Chemspider, the detailed fragmentation patterns were listed in Table 2.

3.4.5. Oxylipins

Peak 41 with parent ion [M-H]- at m/z 327.2192 was assigned as 9,12,13-trihydroxy

-octadecadienoic acid due to the similar fragmentation pattern with that reported in references

(Rodríguez-Pérez, Quirantes-Piné, Fernández-Gutiérrez, & Segura-Carretero, 2013 and Zhang, et al.,

2014). Peak 57 presented precursor ion at 293.2119, MS/MS ions at 171.1019 (C9H16O3) and

121.1016 (C9H14) resulted from the breakage of C9-C10 bond, indicating the location of three oxygen

atoms and the absence of C=C bond at C1-C9, as well as the presence of two or three C=C bonds on

C10-C18. It was then tentatively identified as 9-hydroxy-10,12,15-octadecatrienoic acid (Zhang, et

al., 2014), the detected fragmentation pattern was given in Fig.4G. Analogously, peak 60 (295.2280,

C18H32O3 ) was proposed as 9-hydroxy-10,12-octadecadienoic acid.

3.4.6. Other compounds

Peak 11 was assigned as tryptophan by comparing the MS and MS/MS ions with that recorded in

18
reference (Jiménez-Sánchez, et al., 2016). Peak 18 with [M-H]- at m/z 216.0872 yielded base peak at

198.0764 and 172.0976 resulting from the dehydration and decarbonation of parent ion, respectively.

Product ions at 115.0029 (C4H4O4) and 100.0769 (C5H11NO) were formed from the breakage of amide

bond. Then, peak 18 was proposed as [2-Oxo-2-[(tetrahydro-2-furanylmethyl)amino]ethoxy]acetic

acid by comparing the molecular formula of C9H15NO5 with the data documented in database, the

detected fragmentation pattern and MS/MS spectra are shown in Fig.4H. Peak 19 showed a

characteristic fragment at 144.0451 [M-diglucuronic acid-H]- was tentatively identified as hydroxy-1

-isoquinolinone-diglucuronide. Peak 53 presented m/z at 194.0827 (C10 H13NO3) was proposed as

damascenine, fragment ions at m/z 179.0583, 164.0840 and 149.0608 indicated the loss of CH4, 2CH3

and CH4 +CH2 O, respectively.

Conclusion

This research constitutes the first assessment of antioxidant and hypoglycemic potential along with

the comprehensive identification of phytochemical compounds of jackfruit peel. Comparing with

jackfruit pulp, flack and seed, peel extract gave the highest total phenolic and total flavonoid content

with the value of 48.04 mg GAE/g DM and 2.79 mg QuE/g DM, respectively. The strongest radical

scavenging ability and a-glucosidase inhibition were also detected in jackfruit peel extract, and the

later was about 11.8 fold of that of acarbose. Fifty three compounds were tentatively characterized

with HPLC-QTOF-MS/MS, including 8 organic acids, 8 glycosides, 12 phenolic acids, 18 flavonoids,

3 oxylipins and 4 other compounds. In addition, the MS/MS fragmentation pattern of 11 compounds

such as morachalcone A, phloretin-C-dihexoside and hexenyl-5,7,4'-trihydroxyflavan were firstly

described in details. This research indicated that jackfruit peel could be a promising source of

a-glucosidase inhibitors, the results can also provide useful information for the further functional

19
research of jackfruit peel and rapid identification of bio-active compounds from other plant materials.

But further researches are needed to elucidate the delicate structure of which contribute to the tested

bio-activities, along with the in vivo antioxidant and hypoglycemic activity.

Acknowledgment

All authors thanks to the financial support of Education Department of Jiangxi Province

(GJJ150331) and National Natural Science Foundation of China (No. 21276118) .

Conflict of interest statement

All authors have no conflict of interest on the publication of this manuscript.

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26
Figure captions

Fig.1. The ABTS+· scavenging ability (A), DPPH· scavenging ability (B) and a-glucosidase inhibition

of jackfruit peel, pulp, fruit flake and seed extract.

Fig.2. Total ion chromatogram of jackfruit peel extract under negative ion mode

Fig.3. The fragmentation pattern of [5-glucopyranosyloxy-2-oxo-2,3-dihydro-1H-indol-3-yl] acetic

acid (A), benzyl 2-O-β-D-xylopyranosyl-β-D-glucopyranoside (B), esculetin-5-C-glucoside (C),

(Epi)catechin (D), and phloretin-C-dihexoside (E).

Fig.4. The fragmentation pattern of dihydromyricetin (A), Morachalcone A (B),

pentenyl-C-isoliquiritigenin (C), pentenyl-O-naringenin (D), prenylnaringenin (E),

hexenyl-5,7,4'-trihydroxyflavan (F), [2-Oxo-2-[(tetrahydro-2-furanylmethyl)amino]ethoxy]acetic acid

(G) and 9-hydroxy-10,12,15 -octadecatrienoic acid (H).

27
 A
100 100 B

ABTS+· scavenging ability

DPPH· scavenging ability

80 Peel 80
Pulp
Fruit flake Peel
60 60 Pulp
Seed
Fruit flake
40 Seed
40

20
20
0
0
0 2 4 6 8 10 0 1 2 3 4 5 6 7 8 9 10
Concentration (mg/mL) Sample concentration (mg/mL)

C
100
α-Glucosidase inhibition (%)

80

60
Peel
40 Pulp
Fruit flake
20 Seed

0 5 10 15 20
Sample concentration (mg/mL)

Fig.1. The ABTS+· scavenging ability (A), DPPH· scavenging ability (B) and a-glucosidase inhibition of

jackfruit peel, pulp, flake and seed extracts.

6
10 ×10
5
15 ×10
4

8 10
3 19
15 17 18
13 20 21
5 10 11 14 16 24
49
Response

8 9 12 22
20 5
×10 45 53
6 50
0
8.0 8.5 9.0 9.5 10.0 10.5 11.0 11.5 12.0 12.5 13.0 13.5 14.0 14.5 15
Retention time (min) 46 51 56 57
4748 52 62
10 55
43 54 58
44
4 42
59 61
5 41 60
2

23 0
40 41 42 43 44 45 46 47 48 49 50
1 Retention time (min)
2 27
29
26 35 36
5 6 7 24 28 3031 32 33 34 37 38 39
25 40

4 8 12 16 20 24 28 32 36 40 44 48
Retention time (min)

Fig.2. Total ion chromatogram of jackfruit peel extract under negative ion mode

28
 OH OH
A B HO OH
OH -H2O
O 131.0338 113.0243
HO O 144.0455 269.1041 -CO
O O
89.0245 O 85.0301
O N HO O
HO H
119.0346
71.0149 O
HO HO
401.1460
[5-glucopyranosyloxy-2-oxo-2,3-dihydro
OH
-1H-indol-3-yl]acetic acid
-C7H 8O
C 131.0338
-O O O 101.0243 OH
189.0181 HO
-O O O
HO
HO 71.0140 HO O
O HO 133.0274
219.0276
159.0443 161.0456
-CO HO
OH O-
177.0187
191.0327 Benzyl 2-O-β-D-xylopyranosyl
OH
-β-D-glucopyranoside
Esculetin-5-C-glucoside 339.0724

3
. 030
D 109 OH O-
E
OH O-
0,3 A- 1,4A-
O
HO O O
0,2B- HO OH 387.1092
OH HO OH
HO O
OH 289.0728
HO O
Electron OH
rearrangement -CO2 O O OH
HO OH
OH OH
357.0977 417.1200
HO OH OH
HO O
OH O-
205.0503
597.1838 O-
O-
O
OH 245.0790
-CO2 O
HO OH
HO HO OH 209.0458
HO O
167.0358
OH
HO OH
O- 161.0595 OH
OH OH 315.0882
-C7H8O
(Epi)catechin 345.0967 239.0567
Phloretin-C-dihexoside

Fig. 3. The fragmentation pattern of [5-glucopyranosyloxy-2-oxo-2,3-dihydro-1H-indol-3-yl] acetic

acid (A), benzyl 2-O-β-D-xylopyranosyl-β-D-glucopyranoside (B), esculetin-5-C-glucoside (C),

(Epi)catechin (D), and phloretin-C-dihexoside (E).

29
 OH
A 193.0145 OH B 203.0722
0,2A-
HO O-
324.1028 161.0237
-O O
OH

OH
269.0809
OH O OH
OH O -H2O 135.0454
1,4A- 301.0340 177.0926
Dihydromyricetin 319.0462 Morachalcone A 339.1246

296.0687 OH
C 203.0722 D 269.0460
O- 253.0495
293.0826 O O

324.1003 0,3 -
281.0465 B 137.0248

265.0590 OH O OH O
119.0504
253.0500 225.0556 Prenyl-O-naringenin 339.1249
Pentenyl-C-isoliquiritigenin 323.1291
-H 2O
183.0123
O-
119.0504 F
E 121.0229
HO O HO O

225.0556 253.0500 OH O 217.1243 135.0447

-CO OH -C 6H12
203.0713 91.0053 109.0292
-H 2O
Pentenylnaringenin 339.1238
Hexenyl-5,7,4'-trihydroxyflavan 339.1601
G
198.0764
115.0029 172.0976 H 121.1016 OH O
H 183.1385
N O-
O O O-
275.2023
100.0769 O O 211.1330 171.1019
[2-Oxo-2-[(tetrahydro-2-furanylmethyl) 9-Hydroxy-10,12,15-octadecatrienoic acid 293.2119
amino]ethoxy]acetic acid 216.0872

Fig. 4. The fragmentation pattern of dihydromyricetin (A), morachalcone A (B),

pentenyl-C-isoliquiritigenin (C), pentenyl-O-naringenin (D), prenylnaringenin (E),

hexenyl-5,7,4'-trihydroxyflavan (F), [2-Oxo-2-[(tetrahydro-2-furanylmethyl)amino]ethoxy]acetic acid

(G) and 9-hydroxy-10,12,15 -octadecatrienoic acid (H).

30
 Table 1

Total phenolic and total flavonoid content, antioxidant activities and α-glucosidase inhibition

of extracts from jackfruit peel, seed, flesh and flake

IC 50 value (mg DM/mL)
Total phenolics Total flavonoids
DPPH· scaveng ABTS+· scaveng α-glucosidase
(mg GAE/g DM) (mg QuE/g DM)
ing ability ing ability inhibition
c c b b
Peel 48.04± 4.57 2.79 ± 0.04 1.25 ± 0.14 0.23 ± 0.02 0.05 ± 0.00 a
a b c
Pulp 10.34 ± 0.16 2.27 ± 0.31 N.D. 5.70 ± 0.37 6.81 ±0.52 d
Flake 11.57 ± 0.06 b 2.29 ± 0.03 b N.D. 8.21 ± 0.25 e 10.52 ± 0.73 e
Seed 9.71 ± 0.06 a 1.62 ± 0.10 a N.D. 7.62 ± 0.13 d 1.79 ± 0.15 c
B, a B, a
Standard 0.30 ± 0.04 0.02 ± 0.00 0.59 ± 0.04 A, b

Note: N.D. means the IC50 value is over 10 mg/mL. B: butylated hydroxytoluene (BHT) was used as positive control.

A: acarbose was used as positive control. Different letters (a, b, c, et al.) on the same column indicated significantly

difference (p < 0.05).

31
Table 2

Identified or tentatively identified compounds from the extract of jackfruit peel by HPLC-QTOF-MS/MS under negative ion mode.
Rt MS Molecular Molecular Error
No. -
MS/MS fragments Proposed compounds
(min) [M-H] formula weight (ppm)
Organic acid
1 2.89 377.0876 C 18H 18O 9 387.0949 0.54 341.1098(100) [M-2H2O-H]-, 215.0331(16) [M-hexosyl-H] -, 179.0563(51) Naphthalenedicarboxylic acid
[hexose-H]-, 119.0352 (35) [hexose-2CH2O-H]- -hexose
- -
2 2.99 191.0583 C7H12O6 192.0634 -3.16 127.0402(16) [M-2H2O-CO-H] , 85.0299 (90) [M-C3H6O4-H] Quinic acid
3 3.21 133.0150 C4H6O5 134.0223 1.84 115.0038(100) [M-H2O-H]-, 71.0144 [M-H2O-CO2-H]- Malic acid
- -
4 3.30 191.0571 C7H12O6 192.0634 -4.15 127.0397(17) [M-2H2O-CO-H] , 85.0298(100) [M-C3H6O4-H] Quinic acid isomers
- -
5 3.99 191.0206 C6H8O7 192.0270 -4.55 111.0089(83) [M-CO2-2H2O-H] , 87.0091(100) [M-C 3H4O4-H] Citric acid
- -
6 5.71 368.1001 C 16H 19NO9 369.1060 -3.78 144.0455(100) [M-CO2-C6H12O6-H] , 119.0346(32) [C 4H8O4-H] , 89.0245(53) [5-glucopyranosyloxy-2-oxo-2,3-di
[C3H 6O3-H]-, 71.0149 (21) [C3H4O2-H]- hydro-1H-indol-3-yl]acetic acid
- -
7 5.92 315.0737 C 13H 16O 9 316.0794 -4.89 153.0193(79) [resorcylic acid-H] , 135.0073(54)[resorcylic acid-H2O-H] , Resorcylic acid-O-hexoside
-
109.0276(100) [resorcylic acid-CO2-H]
21 12.14 293.1242 C 12H 22O 8 294.1315 -0.03 173.0840 (12) [M-C 4H8O4-H]-, 131.0711(100) [M-hexose-H]-, 101.0237(31) Hydroxycaproic acid-O-hexoside
- -
[C4H 6O3-H] , 85.0662(85) [C 4H6O3-H]
Glycosides
8 8.21 309.1191 C 12H 22O 9 310.1264 0.02 161.0453(52) [hexosyl-H] -, 101.0585(79) [hexosyl-2CH2O-H]-C5H9O2, Digitoxosylhexoside
-
129.0575(39) [digitoxosyl-H]
26 16.70 401.1460 C18H26O10 402.1526 -1.69 269.1041(25) [M-pentosyl-H]-, 161.0456(33) [hexosyl-H]-, 113.0243(44) Benzyl-pentosylhexoside
[pentosyl-H2O-H]-, 101.0243(44) [hexosyl-2CH2O-H]-, 85.0301(98)
[pentosyl-H2O-CO-H]-, 71.0140(100) [hexosyl-3CH2OH-H]-
30 18.16 381.1780 C16H30H10 382.1839 -3.61 249.1332(91) [M-pentosyl-H]-, 161.0442(67) [hexosyl-H] -, 113.0235(70) Pentyl-pentosylhexoside
[pentoysl-H 2O-H] , 101.0236(85) [hexosyl-2CH2O-H]-
-

32
Table 2 (continued)
Rt MS Molecular Molecular Error
No. MS/MS fragments Proposed compounds
(min) [M-H]- formula weight (ppm)
31 19.21 381.1775 C16H30H10 382.1839 -2.3 249.1334(84) [M-pentosyl-H]-, 161.0452(21) [hexosyl-H]-, 113.0241(40) Pentyl-pentosylhexoside isomer I
- -
[pentosyl-H 2O-H] , 101.0242(100) [hexosyl-2CH 2O-H]
32 19.63 381.1781 C16H30H10 382.1839 -3.87 249.1334(100) [M-pentosyl-H]-, 161.0442(43) [hexosyl-H]-, 129.0187(20) Pentyl-pentosylhexoside isomer II
- -
[M-pentosyl-4CH2O-H] , 113.0256(36) [pentosyl-H 2O-H] , 101.0236(95)
[hexosyl-2CH2O-H]-
33 24.92 443.1575 C20H28O11 444.1632 -3.64 401.1439(28) [M-C2H2O-H]-, 269.1023(50) [M-C2H2O-pentosyl-H]-, Benzyl-acetylpentosylhexoside
- -
161.0454(76) [hexosyl-H] , 131.0338(24) [hexosyl-H] , 113.0238(100)
[pentosyl-H 2O-H]-, 101.0242(31) [hexosyl-2CH2O-H]-
35 27.17 671.2780 C28H48O18 672.2841 -1.8 249.1346(100)[M-C 17H 26O 12-H]-, 161.0426(14) [hexosyl-H]-, 101.0249(12) Pentyl-dipentosylglucuronide-hexo
-
[hexosyl-2CH2O-H] side
- -
36 27.34 423.1875 C18H32O11 424.1945 -0.74 381.1757(26) [M-C2H2O-H] , 249.1335 (100) [M-C2H2O-pentosyl-H] , Pentyl-acetylpentosylhexoside
161.0454(17) [hexosyl-H] -, 113.0243(21)[pentosyl-H2O-H]-, 101.0249(80)
[hexosyl-2CH2O-H]-
Oxylipins
41 41.32 327.2192 C 18H 32O 5 328.2250 -4.58 229.1441(52) [M-C6H10O-H]-, 211.1337(100) [M-C6H12O2-H]-, 197.1154(22) 9,12,13-Trihydroxy-octadecadienoi
- - -
[M-C7H14O2-H] , 183.1406(32) [M-C7H12O3-H] , 171.1022(67) [M-C 9H16O2-H] , c acid
-
157.0687(20) [M-C7H22O4-H]
57 46.05 293.2119 C 18H 30O 3 294.2195 1.08 275.2023(95) [M-H2O-H]-, 211.1330(22) [M-C6H10-H]-, 183.1385(100) 9-Hydroxy-10,12,15-octadecatrien
- - -
[M-C7H10O-H] , 171.1019(36) [M-C9H14-H] , 121.1016(41) [M-C 9H16O3-H] oic acid
- -
60 47.70 295.2280 C 18H 32O 3 296.2353 -0.44 277.2180(96) [M-H2O-H] , 205.1250(19) [M-C5H14O-H] , 195.1412(42) 9-Hydroxy-10,12-octadecadienoic
[M-C6H12O-H]-, 171.1028(100) [M-C9H 16-H]-, 153.1258(14) [M-C 8H14O2-H]-, acid
-
113.0974(28)[M-C11H18O-H]
Phenolic acids
Table 2 (continued)

33
 Rt MS Molecular Molecular Error
No. -
MS/MS fragments Proposed compounds
(min) [M-H] formula weight (ppm)
9 8.44 353.0885 C 16H 18O 9 354.0951 -1.96 191.0559(100) [quinic acid-H] -, 179.0342(67) [caffeic acid-H]--, 135.0049(30) Cis 3-Caffeoylquinic acid
-
[caffeic acid-CO2-H]
10 8.82 353.0885 C 16H 18O 9 354.0951 -1.96 191.0558(100) [quinic acid-H] -, 179.0342(46) [caffeic acid-H]-, 135.0450(98) Trans 3-Caffeoylquinic acid
[caffeic acid-CO2-H]-
12 10.21 339.0724 C 15H 16O 9 340.0794 -0.72 177.0191(100) [esculetin-H] -, 133.0295(43) [esculetin-CO2-H] -, 105.0345(32) Esculetin-O-hexoside
-
[esculetin-CO 2-CO-H]
14 10.66 339.0715 C 15H 16O 9 340.0794 1.93 219.0276(60) [M-C4H8O4-H]-, 203.0361(54) [M-C4H8O 5-H]-, 191.0327(100) Esculetin-C-hexoside
- - -
[M-C4H8O4-CO-H] , 189.0181(82)[M-C 5H10O5-H] , 177.0187(100) [esculetin-H] ,
159.0443(52)[esculetin-H2O-H]-, 133.0274(61) [esculetin-CO2-H] -
15 10.74 491.1404 C20H28O14 492.1479 0.47 311.0774(8)[M-hexose-H]-, 281.0655(56)[M-hexose-CH2O-H]-, 251.0554(100) 3,4-dihydroxybenzoic acid methyl
- -
[M-hexose-2CH2O-H] , 239.0559(38)[M-hexosyl-3CH2O-H] , 209.0442(100) ester-C-dihexoside
- -
[M-hexosyl-4CH 2O-H] , 167.0342(60)[M-dihexosyl-H] , 137.0268(35)
[M-dihexosyl-CH2O-H] -, 123.0452(28))[M-dihexosyl-CO2-H]-,
111.0444(18)[M-dihexosyl-2CO-H]-
16 10.89 471.1151 C20H24O13 472.1217 -1.45 177.0197(100) [esculetin-H] -, 133.0271(28) [esculetin-CO2-H] -, Esculetin-hexoylpentoside
17 11.04 355.1033 C 16H 20O 9 356.1107 0.44 193.0504(100)[ferulic acid-H]-, 175.0397(18) [ferulic acid-H2O-H]-, 149.0620(45) Feruloylglucoside
-
[ferulic acid-CO2-H]
20 12.09 353.0877 C 16H 18O 9 354.0951 0.3 191.0558(66) [quinic acid-H]-, 179.0342(100) [caffeic acid-H]-, 173.0453(100) Cis 4-Caffeoylquinic acid
[quinic acid-H2O-H] -
22 12.38 341.0873 C 15H 18O 9 342.0951 1.48 179.0349(100) [caffeic acid-H]-, 135.0446(38) [caffeic acid-CO 2-H]- Caffeoylglucoside
-
23 13.13 353.0879 C 16H 18O 9 354.0951 -0.27 191.0560(100) [quinic acid-H] Cis 5-Caffeoylquinic acid
24 14.13 353.0881 C 16H 18O 9 354.0951 -0.81 191.0565(100) [quinic acid-H] - Trans 5-Caffeoylquinic acid

Table 2 (continued)
No. Rt MS Molecular Molecular Error MS/MS fragments Proposed compounds

34
 (min) [M-H]- formula weight (ppm)
27 17.26 353.0882 C 16H 18O 9 354.0951 -1.11 191.0562(79) [quinic acid-H]-, 179.0350(80) [caffeic acid-H]-, 173.0458(100) Trans 4-Caffeoylquinic acid
[quinic acid-H2O-H] -, 135.0452(48) [caffeic acid-CO2-H]-
Flavonoids
13 10.38 577.1356 C30H26O12 578.1424 -0.78 407.0771(35) [M-C8H10O4-H]-, 337.0727 (15) [M-C11H12O6-H]-, 289.0704(100) Procyanidin B
[catechin-H]-, 245.0807(85) [catechin-CO2-H]-, 205.0504(32) [M-CO 2-C3H 4-H]-,
165.0183(25) [2,4B]-, 125.0239(21) [1,4A]-
25 15.88 435.1300 C21H24O10 436.1369 -0.76 271.0565(6) [M-rhamnose-H]-, 151.0408(26) [1,3B]-, 150.0314(27) [1,3B-H]-, (Epi)catechin-O-rhamnoside
137.0246(100)[0,2B]-, 125.0246(38) [1,4A]-
28 17.65 319.0462 C 15H 12O 8 320.0532 -0.81 301.0340(8) [M-H2O-H]-, 193.0145(56) [M-B-ring-H]-, 165.0194(37) [0,2A]-, Dihydromyricetin
1,4 -
125.0246 (100) [ A]
29 18.06 289.0728 C 15H 14O 6 290.0790 -3.58 245.0790(100) [M-CO2-H]-, 205.0503(54) [M-CO2-C3H 4-H]-, 161.0595(44) (Epi)catechin
- 0,2 - 1,4 -
[M-2CO2-C3H4-H] , 137.0247(54)[ B] , 125.0253(100) [ A] , 121.0309(66)
[0,3A]-, 109.0303(72) [B-ring-H]-
34 26.44 597.1838 C27H34O15 598.1898 -2.18 417.1200(21)[M-hexose-H]-, 387.1092(72)[M-hexose-CH2O-H]- , Phloretin-C-dihexoside
- -
357.0977(100)[M-hexose-2CH2O-H] , 345.0967(29) [M-hexosyl-3CH 2O-H] ,
315.0882(38) [M-hexosyl-4CH2O-H]-, 239.0567(18)
[M-hexosyl-3CH 2O-C7H8O-H]-, 209.0458(40) [M-hexosyl-4CH2O-C 7H6O-H]-,
167.0358(34)[M-hexosyl-4CH 2O-C 9H8O2-H]-
37 28.32 303.0516 C 15H 12O 7 304.0583 -1.89 217.0505(58) [M-C3H2O3-H]-, 189.0570(38) [M-C3H2O 3-CO-H]-, 177.0166(63) Dihydroquercetin
[1,4B--H2O-H] -, 151.0045(45)[1,3A]-, 125.0238(100) [ 1,4A]-, 123.0467(60) [1,2B]-
44 42.00 325.1091 C19H18O5 326.1154 -2.92 283.0600(16) [M-C3H6-H]-, 269.0437(50) [M-C4H8-H]-, 256.0378(100) Prenylmethylfluorone
- - -
[M-C5H9-H] , 255.0316(42) [M-C 5H10-H] (Y0), 227.0363(25)[Y 0-CO] ,
211.0413(54) [Y0-CO2]-, 183.0107(66) [M-C 8H4O2-H]-
Table 2 (continued)
Rt MS Molecular Molecular Error
No. -
MS/MS fragments Proposed compounds
(min) [M-H] formula weight (ppm)

35
45 42.70 311.1299 C 19H 20O 4 312.1362 -3.26 293.1207(17) [M-CH2O-H]-, 267.0671(64)[M-C3H8-H]-, 241.0506(94) Prenyl-O-tetrahydroxy-9,10-dihydr
[M-C5H10-H]-, 225.0568(31) [M-C5H10O-H]-, 201.0555(42) [M-C 7H10O-H]-, ophenanthrene
- -
189.0924(56)[M-C7H6O2-H] , 183.0124(100) [M-C7H 12O2-H] , 173.0609(56)
[M-C8H10O2-H]-, 159.0454(82) [M-C9H12O2-H]-
46 42.96 339.1249 C 20H 20O 5 340.1311 -3.24 324.1003(10) [M-CH2-H]-, 296.0687(26) [M-C 3H7-H]-, 281.0465(100) Prenyl-O-naringenin
- - -
[M-C4H10-H] , 269.0460(43) [M-C5H10-H] , 253.0495(21) [M-C5H10O-H] ,
197.0607(29) [M-C7H10O3-H]-, 137.0248(67) [0,3A]-
47 43.05 393.1716 C 24H 26O 5 394.1780 -2.16 339.1258(56)[M-C4H6-H]-, 281.0467(59) [M-C4H6-C4H 10-H]-, Butenylprenylnaringenin
- -
269.0458(61)[M-C4H6-C5H10-H] , 255.0649(52)[M-C 4H6-C5H8O-H]
50 43.65 339.1246 C 20H 20O 5 340.1311 -2.36 324.1028(29) [M-CH2-H]-, 269.0479(20) [M-C 5H10-H]-, Morachalcone A
203.0722(30)[M-C8H8O2-H]-, 177.0926(100) [M-C9H 8O3-H]-,
161.0237(71)[M-C11H14O2-H]-, 135.0454(87) [M-C12H12O3-H]-
51 43.95 339.1246 C 20H 20O 5 340.1311 -2.36 324.0976(20) [M-CH2-H]-, 283.0632(26) [M-C 4H8-H]-, 203.0699(27) Morachalcone A isome r
[M-C8H8O2-H]-, 177.0914(56) [M-C9H8O3-H]-, 161.0235(25) [M-C11H14O2-H]-,
135.0456(81) [M-C12H12O3-H]-, 119.0504(53) [M-C12H12O 4-H]-
52 44.53 379.1920 C 24H 28O 4 379.1915 -1.36 361.1786(8) [M-H2O-H]-, 335.2022(27) [M-CO2-H]-, Chlorophorin
311.2018(13) [M-C 3O2-H]-, 255.0662(32) [M-C 9H16-H]-, 241.0505(100)
[M-C10H18-H]-, 211.0752(14) [M-C10H16O2-H]-, 159.0461(21) [M-C 14H 18O2-H]-
54 45.25 323.1291 C 20H 20O 4 342.1362 -0.67 293.0826(17) [M-C2H6-H]-, 265.0509(100) [M-C 4H10-H]-, 253.0500(76) Pentenylisoliquiritigenin
[M-C5H10-H]-, 225.0556(71) [M-C5H10-CO-H]-, 203.0713(10) [M-C 8H8O2-H]-,
119.0504(73) [M-C 12H12O3-H]-
55 45.46 337.1082 C 20H 18O 5 338.1151 -0.16 293.0454(15) [M-C3H8-H]-, 203.0714(86) [M-C8H6O2-H]-, 175.0763(12) Prenylgenistein
[M-C9H6O3-H]-, 159.0813(62) [M-C9H6O4-H]-, 133.0297(100) [M-C12H12O3-H]-
Table 2 (continued)
Rt MS Molecular Molecular Error
No. -
MS/MS fragments Proposed compounds
(min) [M-H] formula weight (ppm)
56 45.88 339.1238 C20H20O5 340.1311 -0.01 324.0981(12) [M-CH2-H]-, 309.0767(7) [M-C 2H6-H]-, 281.0455(100) Pentenylnaringenin

36
 [M-C4H10-H]-, 269.0454(88)[M-C5H10-H]-, 241.0502(68)[M-C 5H10-CO-H]-,
203.0704(11) [M-C 8H8O2-H]-, 159.0816(11)[M-C9H8O3-H2O-H]-
58 46.17 339.1601 C 21H 24O 4 340.1675 0.24 217.1243(15)[0,3B]-, 183.0123(15) [1,3B-H2O]-, 135.0447(100) [1,3B-C6H12]-, Hexenyl-5,7,4'-Trihydroxyflavan
0,3 - 0,4 - 0,4 -
121.0229(11)[ A] , 109.0292(19)[ A] , 91.0053(24) [ A-H2O]
62 49.82 323.1289 C 20H 20O 4 324.1362 -0.05 308.1043(9) [M-CH2-H]-, 293.0808(10) [M-C 2H6-H]-, Pentenyl-O-isoliquiritigenin
- -
265.0504(99)[M-C4H10-H] , 253.0505(94) [M-C5H10-H] ,
237.0554(9)[M-C5H 10O-H] -, 225.0552(100) [M-C5H 10-CO-H]-
Amino acids, peptides and derivatives
11 9.91 203.0825 C11H12N2O2 204.0899 0.5 159.0926(10) [M-CO2-H]-, 142.0656(21) [M-CO2-NH3-H]-, 116.0501(100) Tryptophan
- -
[M-C3H5NO2-H] , 74.0246(93) [C2H5NO2-H]
18 11.48 216.0872 C9H15NO5 217.0950 2.52 198.0764(15)[M-H2O-H]-, 172.0976 (36) [M-CO2-H]-, 115.0029(16) [2-Oxo-2-[(tetrahydro-2-furanylme
- -
[M-C5H11NO-H] , 100.0769(35) [M-C4H4O4-H] , 88.0405(42) thyl)amino]ethoxy]acetic acid
[M-CO 2-C 5H8O-H]-
19 11.78 512.1411 C22H27NO13 513.1482 -0.27 161.0451(16) [glucosyl-H]-, 144.0451(100) [M-diglucuronic acid-H]-, Hydroxy-1-isoquinolinone-diglucu
- -
101.0242(43) [glucosyl-2CH2O-H] , 99.0249(43) [C8H4-H] , ronide
-
73.0297(56)[glucosyl-2CH 2O-CO-H]
53 44.78 194.0827 C 10H 13NO3 195.0895 -2.22 179.0583(41)[M-CH4-H]-, 164.0540(12)[M-2CH3-H]-, Damascenine
- -
149.0608(65)[M-CH4-CH2O-H] , 121.0665[M-CH 4-C 2H2O2-H]
Unknown
38 29.75 723.5029 C36H72N 2O1 724.5085 -2.28 677.4985(43), 563.4274(14), 451.3352(14), 433.3171(23), 338.2456(33), unknown
2 225.1613(100), 130.0870(54)
39 31.57 836.5872 C43H79N 7O9 837.5939 -0.66 790.5818(100), 772.5716(31), 451.3303(16), 338.2460(26), 225.1609(100), unknown
130.0874(27)
Table 2 (continued)
Rt MS Molecular Molecular Error
No. -
MS/MS fragments Proposed compounds
(min) [M-H] formula weight (ppm)
40 32.97 949.6714 C53H94N 2O1 950.6807 2.1 904.6666(40), 903.6656(100), 564.4134(6), 451.3296(11), 338.2439(12) , unknown

37
 2 225.1605(32), 130.0874(8)
42 41.75 242.1772 C 13H 25NO3 243.1834 -4.25 225.1507(98), 181.1595(100) unknown
43 41.82 327.1251 C 19H 20O 5 328.1311 -3.97 unknown
48 43.38 353.1039 C 20H 18O 6 354.1103 -2.37 - unknown
49 43.55 293.1765 C 17H 26O 4 294.1831 -2.27 - unknown
59 46.67 452.2782 C23H39N 3O6 453.2839 -3.51 255.2329(100), 196.0385(14), 140.0112(20), 78.9592(35) unknown
61 48.12 221.1543 C 14H 22O 2 222.1547 1.82 206.1298(22), 205.1225(54) unknown
Note：Rt: retention time; MS: parent ion under negative ion mode.

：
Highlights：

1. The bioactivities of jackfruit peel were firstly compared with that of pulp, flake and seed.

2. Peel extract gave the highest total phenolic and total flavonoid content.

3. The best antioxidant activities and α-glucosidase inhibition were found in peel extract.

4. 53 compounds were tentatively identified with HPLC-QTOF-MS/MS

5. Detailed fragmentation pattern of 11 compounds under negative mode were firstly described.

38