4. Chiết Xuất Và Tính Chất Dược Lý Của Các Hợp Chất Có Hoạt Tính Sinh Học Từ Quả Nhãn (Dimocarpus Longan Lour.) - Tổng Quan

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Food Research International 44 (2011) 1837–1842

Contents lists available at ScienceDirect

Food Research International


j o u r n a l h o m e p a g e : w w w. e l s ev i e r. c o m / l o c a t e / f o o d r e s

Review

Extraction and pharmacological properties of bioactive compounds from longan


(Dimocarpus longan Lour.) fruit — A review
Bao Yang a, Yueming Jiang a,⁎, John Shi b, Feng Chen c, Muhammad Ashraf d
a
Key Laboratory of Plant Resource Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, People's Republic of China
b
Guelph Food Research Center, Agriculture and Agri-Food Canada, 93 Stone Road West, Guelph, Ontario, Canada N1G 5C9
c
Department of Food Science and Human Nutrition, Clemson University, Clemson, SC 29634, USA
d
Department of Botany, Faculty of Sciences, University of Agriculture, Faisalabad 38040, Pakistan

a r t i c l e i n f o a b s t r a c t

Article history: Mature longan (Dimocarpus longan Lour.) fruit has a succulent, edible and white aril, which has gained popularity
Received 1 September 2010 as an exotic fruit in temperate regions. It is prized on the international market resulting in an increased production
Accepted 10 October 2010 with significant contributions to local economic development. Longan fruit contains significant amounts of
bioactive compounds such as corilagin, ellagic acid and its conjugates, 4-O-methylgallic acid, flavone glycosides,
Keywords:
glycosides of quercetin and kaempferol, ethyl gallate 1-β-O-galloyl-D-glucopyranose, grevifolin and 4-O-α-L-
Longan
Dimocarpus longan Lour.
rhamnopyranosyl-ellagic acid. The fruit has been used in the traditional Chinese medicinal formulation, serving as
Fruit an agent in relief of neural pain and swelling. The application of ultrasonic-assisted extraction or high pressure-
Extraction assisted extraction greatly increases the yield from longan pericarp or seeds. In recent years, some
Bioactive compound pharmacological activities such as anti-tyrosinase, anti-glycated and anticancer activities, and memory-
Pharmacological activities enhancing effects of longan aril, pericarp or seed extract have been found, implicating a significant contribution
to human health. Regarding the increasing cultivation area and increasing quantity of longan fruit in the world,
further utilization of this fruit is expected in an effort to use more efficiently the inherent bioactive compounds.
The paper reviews the recent advances in the extraction and pharmacological activities of bioactive compounds
from longan fruit. Some novel pharmacological potential of longan fruit is also discussed in this paper.
© 2010 Elsevier Ltd. All rights reserved.

Contents

1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1838
2. Extraction of bioactive compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1838
2.1. Conventional extraction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1838
2.2. Ultrasonic-assisted extraction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1838
2.3. High pressure-assisted extraction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1838
3. Nutritional and phytochemical compositions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1839
3.1. Nutrients . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1839
3.2. Phytochemicals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1839
4. Pharmacological properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1839
4.1. Antioxidant activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1839
4.2. Anti-tyrosinase activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1840
4.3. Anti-glycated activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1840
4.4. Potential anticancer activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1840
5. Other beneficial effects . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1840
6. Prospects . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1841
Acknowledgements . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1841
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1841

⁎ Corresponding author. Tel.: + 86 20 37252525; fax: + 86 20 37252831.


E-mail address: ymjiang@scbg.ac.cn (Y. Jiang).

0963-9969/$ – see front matter © 2010 Elsevier Ltd. All rights reserved.
doi:10.1016/j.foodres.2010.10.019
1838 B. Yang et al. / Food Research International 44 (2011) 1837–1842

1. Introduction drying methods: lyophilization N microwave radiation N solar


radiation. Although gallic acid was not detected in either fresh or
Longan (Dimocarpus longan Lour.) is a subtropical evergreen tree lyophilized pericarp tissues, it was found that longan pericarp dried
belonging to the family Sapindaceae (Huang, 1995; Tindall, 1994). by microwave radiation have a higher content than by solar radiation.
Longan fruit has a thin, leathery and indehiscent pericarp surrounding Furthermore, Zheng et al. (2009) identified eight polyphenols, i.e.,
a succulent edible aril with a large dark brown seed. Longan fruit has ethyl gallate 1-β-O-galloyl-D-glucopyranose, methyl brevifolin car-
gained popularity as an exotic fruit in temperate regions, and is prized boxylate, grevifolinand 4-O-α-L-rhamnopyranosyl-ellagic acid, gallic
on world markets with strong demand for its desirable flavour and acid, corilagin and ellagic acid present in longan seed. The conven-
semi-translucent to white aril (Jiang, Zhang, Joyce, & Ketsa, 2002). The tional extraction of polysaccharides from longan pericarp was also
fruit is grown commercially in many countries, including China and investigated using hot water (Yang, Zhao, & Jiang, 2009). It is noted
Thailand, which account for most commercial longan production that the conventional extraction method to use different solvents to
(Huang, Huang, & Zeng, 2005). Longan production has increased over extract fruit compounds should be considered, due to a large number
recent decades because of great improvements in agronomic practices of longan cultivars available.
and other aspects of crop management (Huang et al., 2005; Jiang et al.,
2002). Increasing production of longan fruit raises prospects for 2.2. Ultrasonic-assisted extraction
further utilization for this crop.
Longan fruit is rich in carbohydrates, protein, fiber, fat, vitamin C, The ultrasonic-assisted extraction of oils from chickpea (Lou,
amino acids, and minerals. The fruit has been used traditionally in Wang, Zhang, & Wang, 2010), saponins from ginseng (Engelberth,
Chinese medicinal formulation, serving as a common agent in relief of Clausen, & Carrier, 2010), polysaccharides (Yang, Jiang, Zhao, Shi, &
neural pain and swelling. In recent years, the extract from longan fruit Wang, 2008) and phenolic compounds such as corilagin from longan
including aril, pericarp and seed, has exhibited excellent antioxidant pericarp (Prasad et al., 2009; Yang, Zhao, & Jiang, 2008a) were
ability and good anti-tyrosinase and anticancer activities (Chung, Lin, reported. Under the optimal conditions, 85% acidified ethanol with aid
Chou, & Hsu, 2010; de Assis et al., 2009; Park et al., 2010; Prasad et al., of ultrasonication has been demonstrated to obtain a higher
2009; Rangkadilok et al., 2007; Soong & Barlow, 2004; Yang, Zhao, & extraction yield from longan pericarp, as compared with the
Jiang, 2009; Yang, Zhao, Shi, Yang, & Jiang, 2008c). Thus, longan fruit conventional extraction (Prasad, Yang, Yi, Zhao, & Jiang, 2009).
can be used as a readily accessible source of natural antioxidants and/ Likewise, Zhong and Wang (2010) optimized ultrasonic-assisted
or a possible supplement in the food or pharmaceutical industries. To extraction technology to obtain polysaccharides from dried longan
better utilize the longan fruit, the paper reviews the recent advances pulp using response surface methodology. These results demonstrate
in the extraction of bioactive compounds present in the fruit and their that the ultrasonic-assisted extraction is more effective than the
corresponding biological activities. Some novel pharmacological conventional extraction in extracting bioactive compounds from
potential of longan fruit is also discussed in the paper. The paper longan pericarp.
will give the interested readers more insights of longan fruit, and help
relevant farmers and industries to better utilize this fruit in the future. 2.3. High pressure-assisted extraction

2. Extraction of bioactive compounds The high pressure-assisted extraction (HPE) method, which works
under a very high pressure ranging from 100 to 1000 MPa, has been
Extraction is the most important step in isolating different types of recognized as an environment-friendly technology by the Food and
bioactive compounds from fruits and vegetables. The ideal extraction Drug Administration, and is being extensively applied in pharmaceu-
method should be quantitative, non-destructive and time-saving. tical, metallurgical and food industries. Various researchers have
There are different extraction methods. Recently, use of green successfully used the HPE technique for the extraction of bioactive
technology like ultrasonic-assisted extraction or high pressure- compounds from some fruits such as longan (Prasad, Yang, Yi, et al.,
assisted extraction has been reported for efficient extraction of 2009; Prasad et al., 2010) and grapes (Corrales et al., 2008).
bioactive compounds from longan fruit. Optimization to obtain high corilagin yield from longan pericarp
was investigated under different high pressures (200–500 MPa),
2.1. Conventional extraction times (2.5–30 min), and temperature (30–90 °C) (Prasad, Hao, Shi,
et al., 2009). The content of corilagin obtained by HPE (9.65 mg/g dry
It is the traditional way of extracting bioactive compounds from matter) was significantly higher than that from the ultrasonic-
plant tissues, using soxhlet extractor, magnetic stirrer, boiling, assisted extraction (7.91 mg/g dry matter) or conventional extraction
maceration, grinding and heat reflux (Yang et al., 2008d). The (2.35 mg/g dry matter). In addition, the yields of water-soluble
extraction technique depends largely on the type of solvents, energy polysaccharides, alkali-soluble polysaccharides and cellulose from
input, and agitation to improve the chemical solubility and efficiency longan pericarp were comparatively analysed before and after ultra-
of mass transfer. Usually, the conventional extraction requires long high pressure treatment (Yang, Jiang, Wang, Zhao, & Sun, 2009). It
extraction time with low extraction yield but high energy consump- was found that a negative relationship was observed between
tion. The method is still popular and widely used because it has been pressure and water-soluble polysaccharide yield. However, ultra-
well established and is easy to perform and cheap to operate. high pressure treatment significantly (P b 0.05) increased the degrees
He et al. (2009) reported the phenol contents of 12 Chinese longan of hydrolysis of polysaccharides and lignins from longan pericarp.
cultivars. Polyphenols (52.9 mg/g dry matter) were obtained from the Thus, the efficacy of high pressure to extract different types and yields
pericarp of cultivar ‘Wulongling’ fruit by extraction with aqueous of bioactive compounds from longan fruit needs to be further
acetone. Based on the conventional extraction, Yang et al. (2008d) investigated due to their different stabilities and diffusion rates.
found a great variation in the contents of water-soluble polysacchar- With the recent advances in extraction technologies, bioactive
ides, water-soluble total saccharides, gallic acid and total phenols in compounds from longan fruit or its by-products can be obtained
the pericarp of longan among the three cultivars and drying methods efficiently. It should be noted that application of high pressure-
tested. The longan pericarp tissues contained a large amount of assisted extraction can increase significantly the extraction yield from
phenolic compounds and “Shixia” fruit had the highest content longan pericarp. Furthermore, fewer impurities of the extract are
(49.4 mg gallic acid equivalents/g dry matter) of total phenols. The noticed in the HPE extraction as compared to the conventional
contents of total phenolics exhibited a decreasing order for the three extraction (Jiang, Y.M, unpublished data). Thus, the high pressure-
B. Yang et al. / Food Research International 44 (2011) 1837–1842 1839

assisted extraction technology will exhibit great potential for the membrane lipid-related enzymes and may purportedly enhance
extraction of bioactive compounds from longan fruit. immune function in human consumers. In addition, longan pericarp
contains significant amounts of polysaccharides (Jiang et al., 2009).
3. Nutritional and phytochemical compositions The polysaccharides are mainly composed of L-arabinofuranose
(32.8%), D-glucopyranose (17.6%), D-galactopyranose (33.7%) and
3.1. Nutrients D-galacturonic acid (15.9%) (Yang et al., 2009).

Table 1 presents the principal nutritional components of longan


aril. Furthermore, the different nutritional components for longan 4. Pharmacological properties
fruit may occur across cultivars. The different nutritional components
for longan fruit may occur across cultivars. Among these 16 cultivars, Phenolic compounds present in fruits and vegetables have
‘Zhuliang’ exhibits the highest single fruit weight (10.3 g) and edible attracted great attention due to their beneficial effects to human
portion (65.9%) (Wen et al., 2010b). health (Jacob, Hakimuddin, Paliyath, & Fisher, 2008; Lampila, Van
The concentrations of total sugars in longan aril increase during Lieshout, Gremmen, & Lahteenmaki, 2009). As longan fruit contains
ripening, with absolute sugar content varying with stage of maturity significant amounts of polyphenolic compounds, the longan aril,
and cultivar. The major sugars are sucrose, fructose and glucose (Li, pericarp or seed extract exhibits great antioxidant, anti-tyrosinase,
Miao, & Jiang, 2009). Longan aril also contains malic and tartaric acids anti-glycated and anticancer activities (Prasad, Hao, Shi, et al., 2009;
(Li, Liu, & Wu, 2004). Other organic acids, including oxalic, citric and Rangkadilok et al., 2007; Soong & Barlow, 2004; Yang et al., 2008c).
succinic acids, have also been identified. Malic acid and citric acids are Furthermore, a combination of longan extract with some commercial
the highest at the intermediate maturity stage, and gradually decrease drugs can improve treatment efficacy and facilitate the recovery of the
thereafter. Longan fruit also contains significant amount of amino patients. In addition, longan pericarp and seed as by-products account
acids (Wang et al., 2009), especially γ-aminobutyric acid. The content for 16–40% of the whole fruit by weight, and, thus, they can
of γ-aminobutyric acid in longan aril ranged from 51 to 180 mg/100 g potentially be utilized as a readily accessible source of natural
fresh matter (Zheng et al., 2008). antioxidants and a possible pharmaceutical supplement.
About 28 major volatile compounds from fresh longan aril have
been identified to date. The major volatiles include β-ocimene, 3,4-
dimethyl-2,4,6-octatriene, ethyl acetate, allo-ocimene and 1-ethyl-6- 4.1. Antioxidant activity
ethylidene-cyclohexene (Zhang, Zeng, & Li, 2008; Zhang, Gao, Zhang,
Shi, & Xu, 2009). Different extraction methods influence the volatile There is some direct evidence for the antioxidant potential with
constituents (Chang, Yu, Chang, & Liu, 2008). Thus, the different phenolic compounds in longan fruit (de Assis et al., 2009; Wen, Li,
volatile profile characteristics for longan fruit may occur across Mao, & Zhang, 2010a). Guo et al. (2003) compared the antioxidant
cultivars, environments and cultural practices. activities of peel, pulp and seed fractions of longan fruit using the
FRAP assay, while Prasad, Yang, Shi, et al. (2010) found that
3.2. Phytochemicals polyphenol-rich longan extract can strongly inhibit linoleic acid
oxidation and exhibit a dose-dependent free-radical scavenging
Significant amounts of phenolics, fatty acids and proteins exist in activity against DPPH radicals, superoxide anion and hydroxyl radicals
longan fruit. Phenolic compounds including gallic acid, corilagin, (Figs. 1–5). The different total antioxidant capacities were reported in
ellagic acid and their conjugates, (−)-epicatechin, 4-O-methylgallic longan arils of various cultivars (Table 2). Among these 16 cultivars,
acid, flavone glycosides, glycosides of quercetin and kaempferol from ‘Kusan’ exhibits the lowest FRAP value of 4.19 mmol/L (Yamaguchi,
longan fruit pericarp (Jaitrong, Rattanapanone, & Manthey, 2006; Ariga, Yoshimura, & Nakazawa, 2000). Furthermore, longan poly-
Rangkadilok, Worasuttayangkurn, Bennett, & Satayavivad, 2005; Shi saccharides showed a good antioxidant activity in vitro (Jiang et al.,
et al., 2008; Sun, Shi, Jiang, Xue, & Wei, 2007), and ethyl gallate 1-β-O- 2009; Yang, Jiang, Zhao, et al., 2009). However, methylation of
galloyl-D-glucopyranose, methyl brevifolin carboxylate, grevifolinand polysaccharides from longan pericarp reduced radical scavenging
4-O-α-L-rhamnopyranosyl-ellagic acid, gallic acid, corilagin and activity (Yang, Zhao, Prasad, Jiang, & Jiang, 2010). In addition,
ellagic acid from longan seed (Zheng et al., 2009) have been identified. phenolics from longan pericarp have also found to have excellent
Longan aril contains lysophosphatidyl choline, phosphatidyl choline, reducing power (Duan et al., 2007).
phosphatidyl inositol, phosphatidyl serine, phosphatidyl ethanol-
amine, phosphatidate and phosphatidic acid glycerol (Sheng & Wang,
2010). Such phospholipids can be metabolized by a variety of 100
DPPH Radical Scavenging activity

a a a
80 a a b
Table 1
Nutritional composition per 100 g of fresh longan fruit aril.
Li et al. (2004) and Wall (2006).
60 b c
a
(%)

Moisture (%) 81.4


40
Total carbohydrate 12.38–22.55
Carotene (μg/100 g) 20
Vitamin K (mg/100 g) 196.5 b
20
Reducing sugar (%) 3.85–10.16 c
Retinol (μg/100 g) 3 d
Protein (g/100 g) 1.2 0
Riboflavin (mg/100 g) 0.14 10 50 100
Fiber (g/100 g) 0.4 Concentration (µg/mL)
Ascorbic acid (mg/100 g) 43.12–163.7
HPE UL C BHT
Fat (%) 0.1
Nicotinic acid (mg/100 g) 1.3
Fig. 1. Comparison of DPPH radical scavenging activity from longan fruit pericarp after
Ash (g/100 g) 0.7
application of HPE, UE and CE. For each treatment, the means in a row followed by
Thiamine (mg/100 g) 0.01
different letters were significantly different at the 5% level.
1840 B. Yang et al. / Food Research International 44 (2011) 1837–1842

3.5 a ab 1.2
a
3
ab b b a
c ab 1 a

Absorbance ( 695 nm)


Absorbance (700 nm)

2.5 b c
0.8 d
b
2 a
b 0.6 c c
1.5
c c
0.4 a
1
b
0.5 0.2 c d

0 0
10 50 100 10 50 100
Concentration (µg/mL) Concentration (µg/mL)
HPE UL C BHT HPE UL C BHT

Fig. 2. Comparison of reducing power from longan fruit pericarp after application of Fig. 4. Comparison of total antioxidant activity from longan fruit pericarp after
HPE, UE and CE. For each treatment, the means in a row followed by different letters application of HPE, UE and CE. For each treatment, the means in a row followed by
were significantly different at the 5% level. different letters were significantly different at the 5% level.

4.2. Anti-tyrosinase activity polysaccharides in preventing diabetics and normal aging is worth
further evaluation.
Tyrosinase (EC 1.14.18.1) is a multifunctional enzyme that
catalyzes both the hydroxylation of monophenols such as tyrosine 4.4. Potential anticancer activity
to o-diphenols and the oxidation of o-diphenols to o-quinones.
Meanwhile, the enzyme is widely distributed in organisms and plays Polyphenol-rich longan seed extract is a free-radical scavenger
an important role in melanin production. Tyrosinase inhibitors may be that possesses known pharmacological properties and is used by
clinically useful for the treatment of skin cancer and some dermato- humans for therapeutic purposes. Prasad, Hao, Shi, et al. (2009c)
logical disorders associated with melanin hyperpigmentation and are reported the anticancer activity of pericarp extract of longan fruit
important in cosmetics for whitening and depigmentation after against the HepG2, A549, and SGC7901 cancer cell lines (Table 3). The
sunburn (Shaheen et al., 2005). Rangkadilok et al. (2007) determined extract from longan pericarp obtained by the high pressure-assisted
standardized longan fruit extract. Furthermore, Yang et al. (2008a) extraction showed higher anticancer activity than the conventional
found that polysaccharides from longan fruit pericarp can strongly extraction. Furthermore, polyphenol-rich longan seed extract also
inhibit the tyrosinase activity and act as a noncompetitive inhibitor of inhibited the proliferation of Colo 320DM, SW480 and HT-29 by
the enzyme. The inhibition of tyrosinase activity by the major blocking cell cycle progression during the DNA synthesis phase and
constitutes of longan polysaccharides needs to be investigated further. inducing apoptotic death, reduced the expression of cyclin A and
cyclin D1, activated caspase 3 and increased the Bax/Bcl-2 ratio
4.3. Anti-glycated activity (Chung et al., 2010). It was suggested that a polyphenol-rich longan
extract can be employed as a potential novel treatment agent for
Glycation has been confirmed to have a significant role in diabetic cancer.
complications and normal aging (Yamaguchi et al., 2000). Poly-
saccharides from longan pericarp showed a good and stable anti- 5. Other beneficial effects
glycated activity (Yang, Zhao, & Jiang, 2009). Ultrasonic-assisted
extraction technique can increase the anti-glycated activity of Longan fruit has been used for the traditional Chinese medicine
polysaccharides obtained from longan pericarp. The role of longan formulation to decrease the neural pain and swelling. Besides the

a a
100
70
a a b
b b
Lipid peroxidation inhibitory

b
Superoxide anion scavengng

60 80
a b
a
50 a b
activity (%)

60
activity (%)

40 c
a a
30 ab b c 40
b
20 bc c c
20
c
10

0 0
10 50 100 10 50 100
Concentration (µg/mL) Concentration (µg/mL)
HPE UL C BHT HPE UL C BHT

Fig. 3. Comparison of superoxide anion radical scavenging activity from longan fruit Fig. 5. Comparison of lipid peroxidation inhibitory activity from longan fruit pericarp
pericarp after application of HPE, UE and CE. For each treatment, the means in a row after application of HPE, UE and CE. For each treatment, the means in a row followed by
followed by different letters were significantly different at the 5% level. different letters were significantly different at the 5% level.
B. Yang et al. / Food Research International 44 (2011) 1837–1842 1841

Table 2 Acknowledgements
Total antioxidant capacities and total phenolic contents of arils of different longan
cultivars.
Wen, Xu, et al. (2010b).
This work was supported by the National Natural Science
Foundation of China (Grant Nos. 30928017, U0631004 and
Cultivar Antioxidant activity Total phenolics 31071638), the CAS/SAFEA international partnership program for
(FRAP value, mmol/L) (gallic acid equivalents, mg/L juice)
creative research teams and the Natural Science Foundation of
Shixia 15.82 629.12 Guangdong Province (Grant No. 06200670).
Qingkebaoyuan 3.73 396.65
Kusan No. 2 4.19 179.25
Zhuliang 11.18 401.64
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