臺灣博碩士論文加值系統

橄欖(Canarium album L.)具有多種生理功效，其所含之酚類化合物被認為可能是主
要的機能性成分，為瞭解橄欖中酚類化合物的組成、含量及其生理活性，實驗以固相萃
取匣純化分離酚類化合物後，利用LC/MSn 進行鑑定分析，並以體外試驗方式評估其生
理活性，以作為後續開發橄欖機能性產品之參考。結果顯示，橄欖以50%乙醇搭配超音
波輔助萃取三次，每次5 分鐘,可得的萃取率最高(52%)，總酚含量可達11195±484 mg
GAE/100 g dry fruit。
萃取液回溶於2.5%乙酸後，以C18 固相萃取匣劃分收集，析出液及2.5%乙酸沖提
合併為劃分液A，接續以20%甲醇及50%甲醇沖提，分別收集即為劃分液B 及C，利用
LC/MSn 定性，再以HPLC-PDA 定量，發現劃分液A 層析圖中之最大波峰，經LC-UV/MSn
鑑定特徵碎片並與文獻及標準品比對，確認為5-O-galloylquinic acid (5-GQA)，此為首次
在橄欖中被發現，其含量有3438 mg/100 g dry fruit，為橄欖中含量最高的酚類化合物；
另外每100 克橄欖粉末還含有gallic acid (89±3 mg)、4-O-galloylquinic acid (89±1 mg)及
monogalloyl-hexoside (61±4 mg equivalent of gallic acid (GAE))，而劃分液B 則鑑別出3
種digalloylquinic acid，含量分別為306±9、242±17 及76±5 mg equivalent of galloylquinic
acid (GQAE)，corilagin (211±21 mg)、chebulanin (87±19 mg equivalent of corilagin (CE))
及chebulagic acid (156±30 mg CE)等；劃分液C 則分析出含geraniin (537±34 mg CE)、
geraniin isomer (1109±124 mg CE)、ellagic acid (742±93 mg)、兩種ellagic acid-pentose (639
±179 mg equivalent of ellagic acid (EE))及chebulinic acid isomer (424±48 mg CE)等鞣花單
寧類和kaempferol-hexoside (69±20 mg equivalent of kaempferol)。整合上述，顯示橄欖之
酚類化合物中以沒食子奎寧酸衍生物含量最高，佔總含量之50.1%，其次為鞣花單寧類
佔總量的47.2%。
比較橄欖萃取液、劃分液A、B、C 及5-GQA 之生理活性，結果顯示DPPH 自由基
清除能力以5-GQA (SC50 = 15.4 g/mL)為最強，高達Trolox 的2.7 倍。另外，氧自由基
吸收能力則同樣以5-GQA (3.52 M Trolox E/mg dry extract)最強，約為Trolox 的1.2 倍，
顯然5-GQA 為橄欖中主要之抗氧化活性酚類化合物。澱粉酶抑制能力試驗中，以劃分
液C 之抑制能力(IC50 =108 g/mL)最佳，略低於acarbose (IC50 = 79g/mL)。劃分液B
及C 能有效抑制葡萄糖酶，兩者之抑制能力皆遠高於正對照組，其IC50 分別僅有0.16
和0.15 g/mL，劃分液B 及C 含有高量的鞣花單寧類，可能與其抑制能力有關。另外，
橄欖萃取液、劃分液A、B、C 及5-GQA 之黃嘌呤氧化酶抑制能力皆遠低於正對照組，
並無顯著之功效。

Olive (Canarium album L.) has broad spectrum of bioactivities, which is probably
because of high amount of phenolic compounds. In order to elucidate the compositions and
bioactivities of the phenolic compounds in C. album, the extract of C.album was subjected to
solid phase extraction and LC/MSn to identify the phenol compounds, which the bioactivities
were also evaluated in vitro. The obtained data can be used for the application of C.album.
The results indicated that the highest extraction yield (52%) could be obtained by 50%
ethanol ultrasonic extraction for 5 mins three times. The total phenol contents are 11195±484
mg GAE/100 g dry fruit.
The extract was dissolved in 2.5% acetic acid, and then subjected to C18 solid phase
cartridge. The eluate of the extracts and the eluate by 2.5% acetic acid were collected, which
was named fraction A. The collection of elute by 20% methanol was fraction B, and then
eluted by 50% methanol was as fraction C. The phenolic compounds of collected fractions
were qualtitatived by LC/MSn and the quantified by HPLC-PDA. The largest peak in fraction
A was identified as 5-O-galloylquinic acid (5-GQA), which was found in C. album for the
first time. The content of 5-GQA was 3438 mg/100 g dry fruit, which was the most abundant
phenolic compound in C. album. The fraction A from 100 g of C.album powder also
contained gallic acid (89±3 mg, 4-O-galloylquinic acid (89±1 mg) and monogalloyl-hexoside
(61±4 mg GAE). In fraction B, three kinds of digalloylquinic acid with concertrations of
306±9, 242±17, and 76±5 mg GQAE were found. Besides, corilagin (211±21 mg), chebulanin
(87±19 mg CE), and chebulagic acid (156±30 mg CE) were also observed in fraction B. In
fraction C, there were geraniin (537±34 mg CE), geraniin isomer (1109±124 mg CE), ellagic
acid (742±93 mg), two kinds of ellagic acid-pentose (639±179 mg EE), and chebulinic acid
isomer (424±48 mg CE), which were belongs to ellagitannins. Kaempferol-hexoside (69±20
mg kaempferol equivalent) was also found in fraction C. Collectively, the major phenolic
III
compounds of C. album are derivatives of galloylquinic acid, which is about 50.1% of total
phenolics. Ellagitannins are the other important phenolics about 47.2%.
5-GQA has shown the strongest DPPH free radical scavenging effect (SC50 = 15.4
g/mL), being 2.7 times stronger than Trolox. The highest oxygen radical absorbance
capacity of 5-GQA was observed with value of 3.52 M Trolox E/mg dry extract), which was
about 1.2 times higher than Trolox. It is obviously, 5-GQA is the main antioxidant phenolic
compound of C. album. Fraction C showed the highest -amylase inhibitory activity with IC50
=108 g/mL, which the inhibitory activity was slightly lower than acarbose (IC50 = 79
g/mL). Fraction B and C can effectively inhibited -glucosidase activity with IC50 = 0.16
and 0.15 g/mL, respectively. Their inhibitory ability was much higher than that of the
positive control. Therefore, it is suggested that ellagitannins might result in the -glucosidase
inhibitory activity, since high amount of ellagitannins were found in fraction B and C.
However, no significant xanthine oxidsae inhibitory ability of C. album was observed.

摘要.......................................................................................................................................I
Abstract.............................................................................................................. ...............................II
誌謝............................................................................................................................. .....................IV
目錄.................................................................................................................................................V
表目錄..............................................................................................................................................VIII
圖目錄..............................................................................................................................................IX
附表目錄..................................................................................................................................X
附圖目錄.................................................................................................................................XI
壹、 前言..................................................................................................................................1
貳、 文獻回顧...........................................................................................................................2
一、 橄欖............................................................................................................................2
(一) 品種及生長特性........................................................................................................2
(二) 產量及分布概況........................................................................................................2
(三) 橄欖的應用現況........................................................................................................2
二、 橄欖之酚類化合物....................................................................................................3
(一) 酚酸(phenolic acids) ..................................................................................................3
(二) 類黃酮(flavonoids) ....................................................................................................3
(三) 單寧類(tannins) .........................................................................................................4
(四) 木質素(lignin)............................................................................................................5
(五) 橄欖中酚類化合物含量分析..................................................................................6
三、 橄欖生理活性............................................................................................................6
(一) 抗氧化........................................................................................................................6
(二) 抑制脂肪累積............................................................................................................7
(三) 抗發炎........................................................................................................................7
(四) 抑制醣基化終產物生成............................................................................................7
(五) 抑制癌細胞增生........................................................................................................8
(六) 抑制黃嘌呤氧化酵素活性........................................................................................8
(七) 抗 HIV 病毒...............................................................................................................8
參、 實驗架構...........................................................................................................................9
一、 不同萃取方法之比較................................................................................................9
二、 橄欖萃取液劃分收集及生理活性之探討..............................................................10
三、 橄欖中5-O-galloylquinic acid 之劃分收集及生理活性.........................................11
肆、材料與方法.....................................................................................................................12
一、 實驗材料..................................................................................................................12
VI
二、 藥品與器材..............................................................................................................12
(一) 試驗藥品..................................................................................................................12
(二) 標準品......................................................................................................................12
(三) 層析管柱..................................................................................................................12
(四) 器材..........................................................................................................................12
三、 橄欖樣品粉末製備..................................................................................................13
四、 橄欖酚類化合物萃取條件之探討..........................................................................13
(一) 超音波萃取條件......................................................................................................13
(二) 震盪萃取條件..........................................................................................................14
五、 酚類化合物分析......................................................................................................14
(一) 總酚含量測定..........................................................................................................14
(二) 固相萃取純化條件..................................................................................................14
(三) 高效液相層析分析..................................................................................................15
(四) 橄欖中酚類化合物定性及定量分析......................................................................16
六、 橄欖 5-O-galloylquinic acid 之分析鑑定..................................................................17
(一) 5-O-galloylquinic acid 純化分離方法....................................................................17
(二) 橄欖中 5-O-galloylquinic acid 之質譜儀測定條件...............................................17
七、 抗氧化試驗..............................................................................................................18
(一) 清除 DPPH 自由基.................................................................................................18
(二) 氧自由基吸收能力試驗(ORAC)............................................................................18
八、 糖苷水解酶的抑制活性試驗..................................................................................19
(一) 抑制澱粉酶(-amylase)活性試驗..........................................................................19
(二) 抑制葡萄糖酶(-glucosidase)活性試驗................................................................19
九、 抑制黃嘌呤氧化酶活性測定..................................................................................20
十、 統計分析..................................................................................................................20
伍、 結果與討論.....................................................................................................................21
一、 橄欖中酚類化合物之萃取方法比較......................................................................21
二、 橄欖萃取物之酚類化合物組成分析......................................................................22
(一) 萃取物的劃分收集..................................................................................................22
(二) 萃取物劃分液的分析..............................................................................................23
1. 劃分液 A (Fraction A) .............................................................................................23
(1)酚類化合物組成分析..............................................................................................23
(2)Peak 4 的劃分收集..................................................................................................24
(3)Peak 4 (5-O-galloylquinic acid)之鑑定...................................................................25
2. 劃分液 B (Fraction B) .............................................................................................26
3. 劃分液 C 及D (Fraction C and D)..........................................................................27
(三) 萃取物酚類化合物的組成及定量..........................................................................29
三、 橄欖萃取物的生物活性評估..................................................................................30
VII
(一) 抗氧化活性..............................................................................................................30
1. DPPH 自由基清除能力..........................................................................................30
2. 氧自由基吸收能力(ORAC)....................................................................................31
(二) 糖苷水解酶抑制活性..............................................................................................31
1. 澱粉酶(-amylase) ..................................................................................................32
2. 葡萄糖酶(-glucosidase) ........................................................................................32
(三) 黃嘌呤氧化酶抑制活性..........................................................................................33
陸、 結論................................................................................................................................35
柒、 參考文獻.........................................................................................................................36
捌、 表....................................................................................................................................45
玖、 圖....................................................................................................................................55
拾、附表 .................................................................................................................................70
拾壹、附圖 ..............................................................................................................................72

丁伯平、陳國祥、楊介人、李文明。1999。止嗽青果丸的藥理研究。中成藥，21(1)，27-28。
行 政院農業委員會農糧署- 台灣農業知識入口網
(http://kmweb.coa.gov.tw/jigsaw2010/Detail.aspx?item=259932&kpi=0)。2019。農漁生
產地圖-橄欖。
行政院農業委員會農糧署(http://agr.afa.gov.tw/afa/afa_frame.jsp)。2019。農情報告資訊
網。
何志勇、夏文水。2007。橄榄多酚的提取研究。林產化學與工業，27(1)， 77-80。
林鈺郡。2016。橄欖中酚類化合物組成分佈及其生理活性。國立宜蘭大學食品科學系碩
士班碩士論文。宜蘭。
俞征宙、林求誠。2000。青橄欖利咽含片治療慢性咽炎臨床研究。福建中醫藥，31(2)，
1516。
陳崗、蔣和體、唐春紅。2009。橄欖多酚的保健功效及其應用。中國食品添加劑，(1)，
138142。
陳奕安。2012。利用細胞平台的評估進行中國橄欖萃取物中具抗發炎或抗腫瘤功效成分
的分析與分離。國立臺灣大學食品科技研究所碩士論文。台北。
郭少武、劉進、任大鵬、鄭曉春。2003。青果片治療急性咽炎的臨床觀察。遼寧中醫雜
誌，30(5)，370370。
賈敏、姚秀娟。2001。青橄欖利咽含片的抗炎鎮痛及抑菌作用。西北藥學雜誌，16(4)，
162164。
葉昱德。2013。中國橄欖之抗增生活性因子的純化及鑑定暨其生理活性之研究。國立臺
灣大學食品科技研究所碩士論文。台北。
戴延榮。2001。生嚼橄欖甘草治療咽喉疼痛。醫藥與保健，(8)，2020。
Ahmed, N. 2005. Advanced glycation endproducts—role in pathology of diabetic
complications. Diabetes research and clinical practice, 67(1), 321.
Al-Dabbas, M. M.; KITAHARA, K.; Suganuma; T.; Hashimoto, F.; Tadera, K. 2006.
Antioxidant and α-amylase inhibitory compounds from aerial parts of Varthemia
iphionoides Boiss. Bioscience, biotechnology, and biochemistry, 70(9), 21782184.
Alipour, G.; Dashti, S.; Hosseinzadeh, H. 2014. Review of pharmacological effects of Myrtus
communis L. and its active constituents. Phytotherapy research, 28(8), 11251136.
Arapitsas, P. 2012. Hydrolyzable tannin analysis in food. Food chemistry, 135(3),
17081717.
Atmaca, G. 2004. Antioxidant effects of sulfur-containing amino acids. Yonsei medical
journal, 45, 776788.
Baratto, M. C.; Tattini, M.; Galardi, C.; Pinelli, P.; Romani, A.; Visioli, F.; Pogni, R. 2003.
Antioxidant activity of galloyl quinic derivatives isolated from P. lentiscus leaves. Free
37
radical research, 37(4), 405412.
Bouchet, N.; Barrier, L.; Fauconneau, B. 1998. Radical scavenging activity and antioxidant
properties of tannins from Guiera senegalensis (Combretaceae). Phytotherapy research:
an international journal devoted to pharmacological and toxicological evaluation of
natural product derivatives, 12(3), 159162.
Cerdá, B.; Espín, J. C.; Parra, S.; Martínez, P.; Tomás-Barberán, F. A. 2004. The potent in
vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable
but poor antioxidant hydroxy-6H-dibenzopyran-6-one derivatives by the colonic
microflora of healthy humans. European journal of nutrition, 43(4), 205220.
Cerdá, B.; Tomás-Barberán, F. A.; Espín, J. C. 2005. Metabolism of antioxidant and
chemopreventive ellagitannins from strawberries, raspberries, walnuts, and oak-aged
wine in humans: identification of biomarkers and individual variability. Journal of
agricultural and food chemistry, 53(2), 227235.
Chang, C. W.; Lin, M. T.; Lee, S. S.; Liu, K. C. C.; Hsu, F. L.; Lin, J. Y. 1995. Differential
inhibition of reverse transcriptase and cellular DNA polymerase-α activities by lignans
isolated from Chinese herbs, Phyllanthus myrtifolius Moon, and tannins from Lonicera
japonica Thunb and Castanopsis hystrix. Antiviral research, 27(4), 367374.
Chang, Q.; Su, M. H.; Chen, Q. X.; Zeng, B. Y.; Li, H. H; Wang, W. 2017. Physicochemical
Properties and Antioxidant Capacity of Chinese Olive (Canarium album L.) Cultivars.
journal of food science, 82(6), 13691377.
Chandrasekhar, Y.; Ramya, E. M.; Navya, K.; Kumar, G. P.; Anilakumar, K. R. 2017.
Antidepressant like effects of hydrolysable tannins of Terminalia catappa leaf extract via
modulation of hippocampal plasticity and regulation of monoamine neurotransmitters
subjected to chronic mild stress (CMS). Biomedicine & pharmacotherapy, 86, 414425.
Chiva-Blanch, G.; Arranz, S.; Lamuela-Raventos, R. M.; Estruch, R. 2013. Effects of wine,
alcohol and polyphenols on cardiovascular disease risk factors: evidences from human
studies. Alcohol and alcoholism, 48(3), 270277.
Clifford, M. N.; Stoupi, S.; Kuhnert, N. 2007. Profiling and characterization by LC-MSn of
the galloylquinic acids of green tea, tara tannin, and tannic acid. Journal of agricultural
and food chemistry, 55(8), 27972807.
Dai, J.; Mumper, R. J. 2010. Plant phenolics: Extraction, analysis and their antioxidant and
anticancer properties. Molecules (Basel, Switzerland), 15(10), 7313–7352.
de Sousa Araújo, T. A.; Alencar, N. L.; de Amorim, E. L. C.; de Albuquerque, U. P. 2008. A
new approach to study medicinal plants with tannins and flavonoids contents from the
local knowledge. Journal of ethnopharmacology, 120(1), 7280.
de Sousa, L. R.; Ramalho, S. D.; Fernandes, J. B.; da Silva, M. F. D. G.; Iemma, M. R. D. C.;
Corrêa, C. J.; Vieira, P. C. 2014. Leishmanicidal galloylquinic acids are noncompetitive
inhibitors of arginase. Journal of the brazilian chemical society, 25(10), 18321838.
38
Díaz-de-Cerio, E.; Verardo, V.; Gómez-Caravaca, A. M.; Fernández-Gutiérrez, A.;
Segura-Carretero, A. 2015. Determination of polar compounds in guava leaves infusions
and ultrasound aqueous extract by HPLC-ESI-MS. Journal of chemistry, 2015.
Di Majo, D.; Giammanco, M.; La Guardia, M.; Tripoli, E.; Giammanco, S.; Finotti, E. 2005.
Flavanones in Citrus fruit: Structure - antioxidant activity relationships. Food research
international, 38(10), 11611166.
Downey, M. O.; Rochfort, S. 2008. Simultaneous separation by reversed-phase
high-performance liquid chromatography and mass spectral identification of
anthocyanins and flavonols in Shiraz grape skin. Journal of chromatography A, 1201(1),
4347.
Duan, W.; Tan, S.; Chen, J.; Liu, S.; Jiang, S.; Xiang, H.; Xie, Y. 2013. Isolation of anti-HIV
components from Canarium album fruits by high-speed counter-current
chromatography. Analytical letters, 46(7), 10571068.
Espín, J. C.; González-Barrio; R., Cerdá, B.; López-Bote, C.; Rey, A. I.; Tomás-Barberán, F.
A. 2007. Iberian pig as a model to clarify obscure points in the bioavailability and
metabolism of ellagitannins in humans. Journal of agricultural and food chemistry,
55(25), 1047610485.
Espín, J. C.; Larrosa, M.; García-Conesa, M. T.; Tomás-Barberán, F. 2013. Biological
significance of urolithins, the gut microbial ellagic acid-derived metabolites: the
evidence so far. Evidence-based complementary and alternative medicine, 2013.
Fogliani, B.; Raharivelomanana, P.; Bianchini, J. P.; Bouraı, S.; Hnawia, E. 2005. Bioactive
ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
Phytochemistry, 66(2), 241247.
García-Estévez, I.; Escribano-Bailón, M. T.; Rivas-Gonzalo, J. C.; Alcalde-Eon, C. 2010.
Development of a fractionation method for the detection and identification of oak
ellagitannins in red wines. Analytica chimica acta, 660(1-2), 171176.
Giménez‐Bastida, J. A.; González‐Sarrías, A.; Larrosa, M.; Tomás‐Barberán, F.; Espín, J. C.;
García‐Conesa, M. T. 2012. Ellagitannin metabolites, urolithin A glucuronide and its
aglycone urolithin A, ameliorate TNF‐α‐induced inflammation and associated molecular
markers in human aortic endothelial cells. Molecular nutrition & food research, 56(5),
784796.
González-Centeno, M. R.; Knoerzer, K.; Sabarez, H.; Simal, S.; Rosselló, C.; Femenia, A.
2014. Effect of acoustic frequency and power density on the aqueous ultrasonic-assisted
extraction of grape pomace (Vitis vinifera L.)-a response surface approach. Ultrasonics
sonochemistry, 21(6), 21762184.
Grivennikov, S. I.; Greten, F. R.; Karin, M. 2010. Immunity, inflammation, and
cancer. Cell, 140(6), 883899.
Guo D. J.; Cheng H. L.; Chan S. W.;Yu P. F. 2008. Antioxidative activities and the total
39
phenolic contents of tonic Chinese medicinal herbs. Inflammopharmacology 16(5):
201207.
Gunawan-Puteri, M. D.; Kawabata, J. 2010. Novel α-glucosidase inhibitors from Macaranga
tanarius leaves. Food chemistry, 123(2), 384389.
Hajji, M.; Hamdi, M.; Sellimi, S.; Ksouda, G.; Laouer, H., Li, S.; Nasri, M. 2019. Structural
characterization, antioxidant and antibacterial activities of a novel polysaccharide from
Periploca laevigata root barks. Carbohydrate polymers, 206, 380388.
He, Z.; Xia, W. 2007. Analysis of phenolic compounds in Chinese olive (Canarium album L.)
fruit by RPHPLC-DAD-ESI-MS. Food chemistry, 105(3), 13071311.
He Z.; Xia W.; Chen J. 2008. Isolation and structure elucidation of phenolic compounds in
Chinese olive (Canarium album L.) fruit. European food research and technology
226(5), 11911196.
He, Z.; Xia, W.; Liu, Q.; Chen, J. 2009. Identification of a new phenolic compound from
Chinese olive (Canarium album L.) fruit. European food research and technology,
228(3), 339343.
He, C. 2015. Canarium album (Lour.) Raeusch. 青果(Qingguo, Chinese Olive). In Dietary
Chinese Herbs, 307313.
Hossain, M. B.; Rai, D. K.; Brunton, N. P.; Martin-Diana, A. B.; Barry-Ryan, C. 2010.
Characterization of phenolic composition in Lamiaceae spices by LC-ESI-MS/MS.
Journal of agricultural and food chemistry, 58(19), 1057610581.
Huang, R. T.; Lu, J. F.; Inbaraj, B. S.; Chen, B. H. 2015. Determination of phenolic acids and
flavonoids in Rhinacanthus nasutus (L.) kurz by
high-performance-liquid-chromatography with photodiode-array detection and tandem
mass spectrometry. Journal of functional foods, 12, 498508.
Hussain, S.; Schönbichler, S. A.; Güzel, Y.; Sonderegger, H.; Abel, G.; Rainer, M.; Bonn, G.
K. 2013. Solid-phase extraction of galloyl-and caffeoylquinic acids from natural sources
(Galphimia glauca and Arnicae flos) using pure zirconium silicate and bismuth citrate
powders as sorbents inside micro spin columns. Journal of pharmaceutical and
biomedical analysis, 84, 148158.
Ines, S.; Ines, B.; Wissem, B.; Mohamed, B. S.; Nawel, H.; Dijoux‐Franca, M. G.; Leïla, C. G.
2012. In vitro antioxidant and antigenotoxic potentials of 3, 5‐O‐di‐galloylquinic acid
extracted from Myrtus communis leaves and modulation of cell gene expression by H2O2.
Journal of applied toxicology, 32(5), 333341.
Ismail, A.; Marjan, Z. M.; Foong, C. W. 2004. Total antioxidant activity and phenolic content
in selected vegetables. Food chemistry, 87(4), 581586.
Ito, M.; Shimura, H.; Watanabe, N.; Tamai, M.; Hanada, K.; Takahashi, A.; Tanaka, Y.; Arai,
K.; Zhang, P. L. and Chang, R. 1990. Hepatoproteetive compounds from Canariam
album and Euphorbia nematocypha. Chemical pharmaeeutics bulletin (Tokyo) 38(8),
40
22012203.
Karas, D.; Ulrichova, J.; Valentová, K. 2017. Galloylation of polyphenols alters their
biological activity. Food and chemical toxicology, 105, 223240.
Kumar, S.; Chandra, P.; Bajpai, V.; Singh, A.; Srivastava, M.; Mishra, D. K.; Kumar, B. 2015.
Rapid qualitative and quantitative analysis of bioactive compounds from Phyllanthus
amarus using LC/MS/MS techniques. Industrial crops and products, 69, 143152.
Kumazoe, M.; Fujimura, Y.; Hidaka, S.; Kim, Y.; Murayama, K.; Takai, M.; Wariishi, H.
2015. Metabolic profiling-based data-mining for an effective chemical combination to
induce apoptosis of cancer cells. Scientific reports, 5, 9474.
Kuo, C. T.; Liu, T. H.; Hsu, T. H.; Lin, F. Y.; Chen, H. Y. 2015. Antioxidant and
antiglycation properties of different solvent extracts from Chinese olive (Canarium
album L.) fruit. Asian Pacific journal of tropical medicine, 8(12), 10131021.
Kuo, C. T.; Liu, T. H.; Hsu, T. H.; Lin, F. Y.; Chen, H. Y. 2016. Protection of Chinese olive
fruit extract and its fractions against advanced glycation endproduct-induced oxidative
stress and pro-inflammatory factors in cultured vascular endothelial and human
monocytic cells. Journal of functional foods, 27, 526536.
Landete, J. M. 2011. Ellagitannins, ellagic acid and their derived metabolites: a review about
source, metabolism, functions and health. Food research international, 44(5),
11501160.
Larrosa, M.; Tomás-Barberán, F. A.; Espín, J. C. 2006. The dietary hydrolysable tannin
punicalagin releases ellagic acid that induces apoptosis in human colon adenocarcinoma
Caco-2 cells by using the mitochondrial pathway. The journal of nutritional biochemistry,
17(9), 611625.
Larrosa, M.; García-Conesa, M. T.; Espín, J. C.; Tomás-Barberán, F. A. 2010. Ellagitannins,
ellagic acid and vascular health. Molecular aspects of medicine, 31(6), 513539.
Leung, L. K.; Su, Y.; Chen, R.; Zhang, Z.; Huang, Y.; Chen, Z. Y. 2001. Theaflavins in black
tea and catechins in green tea are equally effective antioxidants. The journal of
nutrition, 131(9), 22482251.
Lipińska, L.; Klewicka, E.; Sójka, M. 2014. Structure, occurrence and biological activity of
ellagitannins: a general review. Acta scientiarum polonorum. Technologia alimentaria,
13(3).
Li, T.; Liu, J.; Zhang, X.; Ji, G. 2007. Antidiabetic activity of lipophilic (-)
-epigallocatechin-3-gallate derivative under its role of α-glucosidase inhibition.
Biomedicine & pharmacotherapy, 61(1), 9196.
Li, D. Q.; Zhao, J.; Xie, J.; Li, S. P. 2014. A novel sample preparation and on-line
HPLC-DAD-MS/MS-BCD analysis for rapid screening and characterization of specific
enzyme inhibitors in herbal extracts: Case study of α-glucosidase. Journal of
pharmaceutical and biomedical analysis, 88, 130135.
41
Liu, Q.; Zhou, M.; Zheng, M.; Chen, N.; Zheng, X., Zeng, S.; Zheng, B. 2016. Canarium
album extract restrains lipid excessive accumulation in hepatocarcinoma cells. Int. J.
Clin. Exp. Med, 9, 1750917518.
Loeb, J. N. 1972. The influence of temperature on the solubility of monosodium urate.
Arthritis & Rheumatism: Official journal of the american college of rheumatology, 15(2),
189192.
Määttä-Riihinen, K. R.; Kamal-Eldin, A.; Törrönen, A. R. 2004. Identification and
quantification of phenolic compounds in berries of Fragaria and Rubus species (family
Rosaceae). Journal of agricultural and food chemistry, 52(20), 61786187.
Maldini, M.;Montoro, P.; Pizza, C. 2011. Phenolic compounds from Byrsonima crassifolia L.
bark: Phytochemical investigation and quantitative analysis by LC-ESI MS/MS. Journal
of pharmaceutical and biomedical analysis, 56(1), 16.
Masuoka, N.; Kubo, I. 2018. Characterization of the xanthine oxidase inhibitory activity of
alk (en) yl phenols and related compounds. Phytochemistry.
Mcdougall, G. J.; Stewart, D. 2005. The inhibitory effects of berry polyphenols on digestive
enzymes. Biofactors, 23(4), 189195.
Mena, P.; Calani, L.; Dall'Asta, C.; Galaverna, G.; García-Viguera, C.; Bruni, R.;Del Rio, D.
2012. Rapid and comprehensive evaluation of (poly) phenolic compounds in
pomegranate (Punica granatum L.) juice by UHPLC-MSn. Molecules, 17(12),
1482114840.
Miliauskas, G.; van Beek, T. A.; Venskutonis, P. R.; Linssen, J. P.; de Waard, P. 2004.
Antioxidative activity of Geranium macrorrhizum. European food research and
technology, 218(3), 253261.
Moilanen, J.; Sinkkonen, J.; Salminen, J. P. 2013. Characterization of bioactive plant
ellagitannins by chromatographic, spectroscopic and mass spectrometric methods.
Chemoecology, 23(3), 165179.
Mogana R. and Wiart C. 2011. Canarium L.: A Phytochemical and Pharmacological Review.
Journal of pharmacy research, 4(8), 24822489.
Motta, E. V.; Lemos, M.; Costa, J. C.; Banderó-Filho, V. C.; Sasse, A., Sheridan, H.; Bastos,
J. K. 2017. Galloylquinic acid derivatives from Copaifera langsdorffii leaves display
gastroprotective activity. Chemico-biological interactions, 261, 145155.
Mohan, C. G.; Viswanatha, G. L.; Savinay, G.; Rajendra, C. E.; Halemani, P. D. 2013. 1, 2, 3,
4, 6 Penta-O-galloyl-β-D-glucose, a bioactivity guided isolated compound from
Mangifera indica inhibits 11β-HSD-1 and ameliorates high fat diet-induced diabetes in
C57BL/6 mice. Phytomedicine, 20(5), 417426.
Mudnic, I.; Modun, D.; Rastija, V.; Vukovic, J.; Brizic, I.; Katalinic, V.; Boban, M. 2010.
Antioxidative and vasodilatory effects of phenolic acids in wine. Food chemistry, 119(3),
12051210.
42
Núñez-Sánchez, M. Á .; Karmokar, A.; González-Sarrías, A.; García-Villalba, R.;
Tomás-Barberán, F. A.; García-Conesa, M. T.; Espín, J. C. 2016. In vivo relevant mixed
urolithins and ellagic acid inhibit phenotypic and molecular colon cancer stem cell
features: A new potentiality for ellagitannin metabolites against cancer. Food and
chemical toxicology, 92, 816.
Okuda, T.; Yoshida, T.; Hatano, T. 1989. Ellagitannins as active constituents of medicinal
plants. Planta medica, 55(02), 117122.
Ou B.; Hampsch-Woodill M.;Prior R. L. 2001. Development and validation of an improved
oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe.
Journal of agricultural and food chemistry 49(10), 46194626.
Palanisamy, U. D.; Ling, L. T.; Manaharan, T.; Appleton, D. 2011. Rapid isolation of geraniin
from Nephelium lappaceum rind waste and its anti-hyperglycemic activity. Food
chemistry, 127(1), 2127.
Pandey, K. B.; Rizvi, S. I. 2009. Plant polyphenols as dietary antioxidants in human health
and disease. Oxidative medicine and cellular longevity, 2(5), 270278.
Peng, L. Q.; Li, Q.; Chang, Y. X.; An, M.; Yang, R.; Tan, Z.; Hu, S. S. 2016. Determination
of natural phenols in olive fruits by chitosan assisted matrix solid-phase dispersion
microextraction and ultrahigh performance liquid chromatography with quadrupole
time-of-flight tandem mass spectrometry. Journal of chromatography A, 1456, 6876.
Perera, A.; Appleton, D.; Ying, L. H.; Elendran, S.; Palanisamy, U. D. 2012. Large scale
purification of geraniin from Nephelium lappaceum rind waste using reverse-phase
chromatography. Separation and purification technology, 98, 145149.
Petigny, L.; Périno-Issartier, S.; Wajsman, J.; Chemat, F. 2013. Batch and continuous
ultrasound assisted extraction of boldo leaves (Peumus boldus Mol.). International
journal of molecular sciences, 14(3), 57505764.
Pietta, P. G. 2000. Flavonoids as antioxidants. Journal of natural products, 63(7), 10351042.
Pittman, J. R.; Bross, M. H. 1999. Diagnosis and management of gout. American family
physician, 59(7), 1799806.
Pfundstein, B.; El Desouky, S. K.; Hull, W. E.; Haubner, R.; Erben, G.; Owen, R. W. 2010.
Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica,
Terminalia chebula and Terminalia horrida): characterization, quantitation and
determination of antioxidant capacities. Phytochemistry, 71(10), 11321148.
Quideau, S.; Feldman, K. S. 1996. Ellagitannin chemistry. Chemical reviews, 96(1), 475504.
Reuter, S.; Gupta, S. C.; Chaturvedi, M. M.; Aggarwal, B. B. 2010. Oxidative stress,
inflammation, and cancer: how are they linked?. Free radical biology and medicine,
49(11), 16031616.
Rezende Jr, C. O.; Rigotto, C.; Caneschi, W.; Rezende, C. A.; Le Hyaric, M.; Couri, M. R.; de
Almeida, M. V. 2014. Anti-HSV-1 and antioxidant activities of dicaffeoyl and digalloyl
43
esters of quinic acid. Biomedicine & preventive nutrition, 4(1), 3538.
Romani, A.; Pinelli, P.; Galardi, C.; Mulinacci, N.; Tattini, M. 2002. Identification and
quantification of galloyl derivatives, flavonoid glycosides and anthocyanins in leaves of
Pistacia lentiscus L. Phytochemical Analysis: An international journal of plant chemical
and biochemical techniques, 13(2), 7986.
Roowi, S.; Stalmach, A.; Mullen, W.; Lean, M. E.; Edwards, C. A.; Crozier, A. 2009. Green
tea flavan-3-ols: colonic degradation and urinary excretion of catabolites by
humans. Journal of agricultural and food chemistry, 58(2), 12961304.
Sang, S.; Lee, M. J.; Yang, I.; Buckley, B.; Yang, C. S. 2008. Human urinary metabolite
profile of tea polyphenols analyzed by liquid chromatography/electrospray ionization
tandem mass spectrometry with data‐dependent acquisition. Rapid Communications in
Mass Spectrometry: An International Journal Devoted to the Rapid Dissemination of
Up‐to‐the‐Minute Research in Mass Spectrometry, 22(10), 15671578.
Schofield, P.; Mbugua, D. M.; Pell, A. N. 2001. Analysis of condensed tannins: a
review. Animal feed science and technology, 91(12), 2140.
Seeram, N. P.; Aronson, W. J.; Zhang, Y.; Henning, S. M.; Moro, A.; Lee, R. P.; Pantuck, A.
J. 2007. Pomegranate ellagitannin-derived metabolites inhibit prostate cancer growth and
localize to the mouse prostate gland. Journal. of Agricultural and food chemistry, 55(19),
77327737.
Taga, M. S.; Miller, E. E.; Pratt, D. E. 1984. Chia seeds as a source of natural lipid
antioxidants. Journal of the american oil chemists’ society, 61(5), 928931.
Törrönen, R. 2009. Sources and health effects of dietary ellagitannins. In Chemistry and
Biology of Ellagitannins: An Underestimated Class of Bioactive Plant Polyphenols,
298319 (edited by Stéphane Quideau); World scientific:Clementi,Republic of
Singapore
Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmidt, D. D.; Wingender, W. 1981.
Chemistry and biochemistry of microbial α‐glucosidase inhibitors. Angewandte chemie
international edition in english, 20(9), 744761.
Vicinanza, R.; Zhang, Y.; Henning, S. M.; Ma, J.; Heber, D. 2012. Pomegranate ellagitannin
metabolite, Urolithin A, inhibits prostate cancer cell proliferation via inhibition of IGF-1
signaling pathway.
Verzelloni, E.; Pellacani, C.; Tagliazucchi, D.; Tagliaferri, S.; Calani, L.; Costa, L. G.; Del
Rio, D. 2011. Antiglycative and neuroprotective activity of colon‐derived polyphenol
catabolites. Molecular nutrition & food research, 55(S1), S35S43.
Wolfe, K. L.; Liu, R. H. 2008. Structure - activity relationships of flavonoids in the cellular
antioxidant activity assay. Journal of agricultural and food chemistry, 56(18),
84048411.
Wu, H. C.; Chen, H. M.; Shiau, C. Y. 2003. Free amino acids and peptides as related to
44
antioxidant properties in protein hydrolysates of mackerel (Scomber austriasicus). Food
research international, 36(910), 949957.
Xiang, Z. B.; Chen, H. S.; Jin, Y. S.; Wang G. L.; Xiang, L. X. ;Chen, W. 2010. Phenolic
constituents of Canarium album. Chemistry of natural compounds. 46(1), 119120.
Yamaguchi, T.; Takamura, H.; Matoba, T.; Terao, J. 1998. HPLC method for evaluation of
the free radical-scavenging activity of foods by using 1,
1-diphenyl-2-picrylhydrazyl. Bioscience, biotechnology, and biochemistry, 62(6),
12011204.
Yang, B.; Kortesniemi, M.; Liu, P.; Karonen, M.; Salminen, J. P. 2012. Analysis of
hydrolyzable tannins and other phenolic compounds in emblic leafflower (Phyllanthus
emblica L.) fruits by high performance liquid chromatography–electrospray ionization
mass spectrometry. Journal of agricultural and food chemistry, 60(35), 86728683.
Yang, W. W.; Wang, L. M.; Gong, L. L.; Lu, Y. M.; Pan, W. J.; Wang, Y.; Chen, Y. 2018.
Structural characterization and antioxidant activities of a novel polysaccharide fraction
from the fruiting bodies of Craterellus cornucopioides. International journal of
biological macromolecules.
Yeh, Y. T.; Chiang, A. N.; Hsieh, S. C. 2017. Chinese Olive (Canarium album L.) Fruit
extract attenuates metabolic dysfunction in diabetic rats. Nutrients, 9(10), 1123.
Yokozawa, T.; Chen, C. P.; Dong, E.; Tanaka, T.; Nonaka, G. I.; Nishioka, I. 1998. Study on
the inhibitory effect of tannins and flavonoids against the 1, 1-diphenyl-2-picrylhydrazyl
radical. Biochemical pharmacology, 56(2), 213222.
Yu, K. H.; Luo, S. F. 2003. Younger age of onset of gout in Taiwan. Rheumatology, 42(1),
166170.
Zafar, H.; M Saad, S.; Perveen, S.; Malik, R.; Khan, A.; M Khan, K.; I Choudhary, M. 2016.
2-Arylquinazolin-4 (3H)-ones: inhibitory activities against xanthine oxidase. Medicinal
Chemistry, 12(1), 5462.
Zhang, Y.; Yang, N. D.; Zhou, F.; Shen, T.; Duan, T.; Zhou, J.; Shen, H. M. 2012.
(−)-Epigallocatechin-3-gallate induces non-apoptotic cell death in human cancer cells via
ROS-mediated lysosomal membrane permeabilization. PloS one, 7(10), e46749.
Zhou, B.; Wang, J.; Zheng, G.; Qiu, Z. 2016. Methylated urolithin A, the modified
ellagitannin-derived metabolite, suppresses cell viability of DU145 human prostate
cancer cells via targeting miR-21. Food and Chemical Toxicology, 97, 375384.