櫸抽出成分延緩老化及阿茲海默症之功效

顏佩翎

doi:10.6342/NTU201703100

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榉抽出成分延缓老化及阿兹海默症之功效

Extractives from Zelkova serrata Delay the Aging Process and Alzheimer’s Disease

颜佩翎 , 博士　　导师：张上镇　　

繁体中文 DOI： 10.6342/NTU201703100

阿兹海默症；抗发炎活性；抗氧化活性；类淀粉β胜肽；乙醇抽出物；精油；榉； Alzheimer’s disease ； amyloid β-peptide ； antiinflammatory activity ； antioxidant activity ； ethanolic extracts ； essential oils ； Zelkova serrata

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摘要 │ 参考文献 (247) │ 国际计量

摘要〈TOP〉

榉 (Zelkova serrata (Thunb.) Makino) 为台湾阔叶树五木之一，且为传统药用植物。本研究目的为评估榉心材、边材及树皮等3部位精油及乙醇抽出物之抗氧化及抗发炎活性，并利用模式生物－秀丽隐杆线虫 (Caenorhabditis elegans (Maupas) Dougherty) 评估其延缓老化及减缓阿兹海默症之功效。
体外试验结果显示，心材精油具有良好的捕捉自由基活性及含有酚类化合物 (161.4 mg of GAE/g)。树皮抽出物之总酚类化合物含量高 (288.1 mg of GAE/g) 且具有良好自由基捕捉能力及还原力，却不具抗发炎活性。心材抽出物的总酚类 (234.8 mg of GAE/g) 及黄酮类化合物含量 (348.5 mg of RE/g) 皆高，不但具有高自由基捕捉能力，且具高抗发炎活性。因此，乃进一步评估心材抽出物各可溶部之抗氧化及抗发炎活性。结果显示，乙酸乙酯可溶部的收率高且抗氧化活性佳，但不具抗发炎活性；正己烷可溶部的收率次之，兼具抗氧化及抗发炎活性。体内试验结果显示，心材精油能显着降低胡桃醌及高温诱导野生型C. elegans (N2 strain) 所产生氧化压力；心材抽出物、其各可溶部及E10次分离部亦能显着提高野生型C. elegans对胡桃醌及高温的压力耐受性。
以生物活性为导向，由榉心材精油及抽出物共获得17个成分，包含15个萜类及2个黄酮类化合物，其中，7-Methoxyzelkoserratone (4)、3-Hydroxy-7-methoxy-3(4H)-isocadalen-4-one (5)、4-Methoxymansonone G (6)、6-Hydroxy-5-isopropyl-2,8-dimethyl-2,3-dihydro-[1,4]naphthoquinone (8)、4,7-Dihydroxy-calamenen-3-one (10)、3-Methoxy-7-hydroxy-3(4H)-isocadalen-4-one (11)、1α-Hydroxy-7-methoxy-1(4H)-isocadalen-4-one (12) 为首次在天然物中发现之成分，7-Hydrxycalamenene (1)、7-Hydroxycadalene (2)、7-Hydroxy-calamenen-3-one (9)、3,7-Dihydroxy-3(4H)-isocadalen-4-one (13) 及Mansonone G (15) 则首次由榉分离而得。
由体外试验结果得知，7-Hydroxycalamenene (1)、7-Hydroxy-3-methoxycadalene (3) 及Kaempferol-6-C-glucoside (17) 之抗氧化活性较佳；7-Hydroxy-3-methoxycadalene (3)、7-Hydroxy-calamenen-3-one (9) 及3,7-Dihydroxy-3(4H)-isocadalen-4-one (13) 之抗发炎活性较佳。心材精油主成分7-Hydroxycalamenene (1) 为体内抗氧化活性来源，且能减缓基因转殖C. elegans (CL4176 strain) 因类淀粉β胜肽累积所造成的瘫痪，推论其有潜力成为减缓阿兹海默症之药剂或保健产品。心材抽出物E10次分离部之主成分－Kaempferol-6-C-glucoside (17) 在正常环境能些微提高野生型C. elegans寿命期，却无延缓老化之功效；然而，在胡桃醌诱导氧化压力及高温环境中，Kaempferol-6-C-glucoside (17) 可显着提升野生型C. elegans寿命期。进一步研究结果显示，在胡桃醌氧化压力下，Kaempferol-6-C-glucoside (17) 可能透过增加转录因子DAF-16 (Dauer formation-16) 及SKN-1 (Skinhead-1) 进入细胞核之比例，分别提高下游压力反应蛋白SOD-3 (Superoxide dismutase-3) 及GST-4 (Glutathione S-transferase-4) 之基因表现量，进而提升C. elegans之压力耐受性。
本研究结果证实榉心材精油及抽出物具有体内及体外抗氧化活性，并具有潜力治疗阿兹海默症，显示榉心材抽出成分极具潜力开发为抗氧化及减缓阿兹海默症之保健食品或药物。

并列摘要〈TOP〉

Taiwan zelkova (Zelkova serrata (Thunb.) Makino) is one of the five most precious hardwood trees in Taiwan, and is also a medical plant based on traditional knowledge. The aim of this study was to evaluate antioxidant and antiinflammatoy activities of essential oils and ethanolic extracts from three plant parts (heartwood, sapwood, and bark) of Z. serrata. In addition, the potential to delay the ageing process and to protect against amyloid-β toxicity of essential oils and ethanolic extracts from Z. serrata were investigated in the model organism Caenorhabditis elegans. 
Results obtained from in vitro assays demonstrated that the essential oil of Z. serrata heartwood exhibited good radical scavenging activities and high total phenolic content (161.4 mg of GAE/g). The bark extract contained the highest level of total phenolic content (288.1 mg of GAE/g), and possessed excellent free radical scavenging activities and reducing power, but bark extract did not exhibit antiinflammatoy activity. The heartwood extract contained high levels of total phenolic (234.8 mg of GAE/g) and total flavonoid contents (348.5 mg of RE/g), and had both antioxidant and antiinflammatoy activities. The antioxidant and antiinflammatoy activities of 4 soluble fractions from heartwood extract were further examined. Results showed that the ethyl acetate soluble fraction had the highest yield and good antioxidant activities, but no antiinflammatoy potential. The n-hexane soluble fraction had high yield as well as good antioxidant and antiinflammatory activities. In vivo assays showed the essential oil of heartwood significantly inhibited oxidative damage in wild-type C. elegans (N2 strain) under juglone-induced oxidative stress and heat shock. The heartwood extract, its soluble fractions and subfraction E10 also significantly increased stress resistance to juglone and heat stress in wild-type C. elegans. 
17 compounds, including 15 sesquiterpenes and 2 flavonoids, were obtained from essential oil and extract of heartwood after a bio-guided fractionation. 7-Methoxyzelkoserratone (4), 3-hydroxy-7-methoxy-3(4H)-isocadalen-4-one (5), 4-methoxymansonone G (6), 6-hydroxy-5-isopropyl-2,8-dimethyl-2,3-dihydro-[1,4] naphthoquinone (8), 4,7-dihydroxy-calamenen-3-one (10), 3-methoxy-7-hydroxy- 3(4H)-isocadalen-4-one (11), and 1α-hydroxy-7-methoxy-1(4H)-isocadalen-4-one (12) were firstly isolated from nature. 7-Hydrxycalamenene (1), 7-hydroxycadalene (2), 7-hydroxy-calamenen-3-one (9), 3,7-dihydroxy-3(4H)-isocadalen-4-one (13), and mansonone G (15) were isolated from Z. serrata for the first time.
In vitro assays showed that 7-hydroxycalamenene (1), 7-hydroxy- 3-methoxycadalene (3), and kaempferol-6-C-glucoside (17) exhibited antioxidant activities; 7-hydroxy-3-methoxycadalene (3), 7-hydroxy-calamenen-3-one (9), and 3,7-dihydroxy-3(4H)-isocadalen-4-one (13) had anti-inflammatory activities. Additionally, the major compound in essential oil of heartwood, 7-hydroxycalamenene, may contribute significantly to the observed antioxidant activity. Further evidence showed that 7-hydroxycalamenene (1) significantly delayed the paralysis phenotype in amyloid beta-expressing transgenic C. elegans (CL4176 strain), revealing that the potential for drugs dietary supplements to slow progress of Alzheimer’s disease. The major compound in subfraction E10 of heartwood extract, kaempferol-6-C-glucoside (17), slightly extended the lifespan of wild-type C. elegans but did not affect the aging behaviors under normal condition. However, kaempferol-6-C-glucoside (17) significantly increased the longevity of wild-type C. elegans under juglone-induced oxidative and thermal stresses. Furthermore, results revealed that kaempferol-6-C-glucoside (17) enhanced the translocations of the transcription factors DAF-16 (dauer formation-16) and SKN-1 (skinhead-1), thereby up-regulating the downstream gene expression of stress response proteins SOD-3 (superoxide dismutase-3) and GST-4 (glutathione S-transferase-4), respectively, to enhance the stress resistance in C. elegans.
The study demonstrated the essential oils and extracts of Z. serrata exhibited in vitro and in vivo antioxidant activities, and has potential to be used as a source for treatment of Alzheimer’s disease. These findings suggest that the extractives from Z. serrata heartwood has potential to be used as health-care food or drug for antioxidant or Alzheimer’s disease treatment.

参考文献 ( 247 ) 〈TOP〉

Abbas, S. and M. Wink (2009) Epigallocatechin gallate from green tea (Camellia sinensis) increases lifespan and stress resistance in Caenorhabditis elegans. Planta Medica 75(3): 216-221.
连结：
Abbas, S. and M. Wink (2010) Epigallocatechin gallate inhibits beta amyloid oligomerization in Caenorhabditis elegans and affects the daf-2/insulin-like signaling pathway. Phytomedicine 17(11): 902-909.
连结：
Aisen, P. S. (2002) The potential of anti-inflammatory drugs for the treatment of Alzheimer's disease. The Lancet Neurology 1(5): 279-284.
连结：
Alexander, A. G., V. Marfil and C. Li (2014) Use of Caenorhabditis elegans as a model to study Alzheimer’s disease and other neurodegenerative diseases. Frontiers in Genetics 5: 279.
连结：
Alvarez, X. A., A. Franco, L. Fernandez-Novoa and R. Cacabelos (1996) Blood levels of histamine, IL-1 beta, and TNF-alpha in patients with mild to moderate Alzheimer disease. Molecular and Chemical Neuropathology 29(2-3): 237-252.
连结：

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