臺灣博碩士論文加值系統

本研究建立一種由芝麻油中分離純化sesamin及sesamolin之簡易方法。首先以n-Hexane稀釋芝麻油，然後通入矽膠管柱，接著依序以n-Hexane、n-Hexane-EtOAc (9:1)及EtOAc流洗。HPLC分析結果顯示n-Hexane-EtOAc (9:1)可以區分出sesamolin，回收率達80.9%，減壓濃縮去除溶劑後，以n-Hexane洗淨得sesamolin結晶。EtOAc 區分層含高濃度之sesamin，回收率達96.3%，減壓濃縮後以少量EtOAc回溶靜置而得sesamin結晶析出。將兩種結晶以n-Hexane洗淨後再使用不同溶劑進行再結晶。

脫脂芝麻粕以80%甲醇水溶液萃取，過濾後減壓濃縮去除溶劑得lignan glycosides粗萃物。利用不同管柱層析法(Amberlite XAD-16、Diaion HP-20、cellulose及silica gel)分離純化sesaminol triglucoside。結果以Diaion HP-20區分sesaminol triglucoside回收率達94.5%，純化倍數則可以提升為80%甲醇粗萃物之9.3倍。以cellulose管柱搭配Diaion HP-20管柱進行純化，純化倍數則可提高18.9倍，回收率達87.2%。

以HPLC分析不同品種芝麻之lignans含量，分析結果顯示每克芝麻平均含3.03 mg sesamin，含量範圍為1.42~6.42 mg。Sesamolin平均含量為1.76 mg，含量範圍為0.92~3.34 mg。Sesaminol triglucoside平均含量為1.21 mg，含量範圍為0.20~2.02 mg。各種芝麻之粗脂肪平均含量為44.8%，含量範圍為40%~48%。

使用芝麻粕(含蛋白質40~50%)來釀造芝麻醬油，經過180天室溫發酵熟成後，醬油製造之相關分析值為：總氮(TN) 1.55%、甲醛態氮(FN) 0.72%、胺基態氮(AN) 0.58%、水解率(DH) 46.5%、TNUR(%) 71.2%、pH值4.9及氯化鈉(NaCl) 17.1%。出麴料之蛋白酶活性為211±7 units/g of koji，澱粉酶活性為67±1 units/g of koji。

Sesamin, esamolin and sesaminol triglucoside in sesame seeds are major lignans that display an abundance of biological activities such as cholesterol-lowering, anticancer, antihypertensive, inhibits lipid peroxidation, antioxidant, enhancement of vitamin E level, protect liver and improve liver function.

In this study, we developed a simple and rapid method for isolation and purification of sesamin and sesamolin from sesame oil by silica gel column chromatography. First of all, sesame oil was diluted with n-Hexane, after that load into silica gel column，stepwise eluted with n-Hexane、n-Hexane-Ethyl acetate (9:1)、Ethyl acetate and Acetone。The n-Hexane-Ethyl acetate (9:1) fraction content high concentration of sesamolin, this separated process could be recover 80.9% of sesamolin. The Ethyl acetate fraction content high concentration of sesamin, that could be recover 96.3% of sesamin. Solvent was removed under vacuum with a rotary evaporator, sesamin and sesamolin crystal were washed with n-Hexane. Sesamin and sesamolin were recrystal with various of solvents.

Defatted sesame meal was extracted with 80% methanol to obtain a crude extract containing sesaminol glucosides. Isolation and purification of sesaminol triglucoside by various column chromatography such as Amberlite XAD-16、Diaion HP-20、cellulose and silica gel column。As a result，isolation and purification of sesaminol triglucoside by Diaion HP-20 column chromatography will increased 9.3 fold of sesaminol triglucoside compared with 80% MeOH crude extract, that could be recover 94.5% of sesaminol triglucoside. Cellulose column combined with Diaion HP-20 column chromatography will increased 18.9 fold and recovered 87.2% of sesaminol triglucoside.

A quantitative analysis of lignans in 10 varieties of sesame seeds by HPLC. The content of sesamin in 1 g sesame seeds ranged from 1.42 to 6.42 mg with an average value of 3.03 mg; Sesamolin ranged from 0.92 to 3.34 mg with an average value of 1.76 mg; Sesaminol triglucoside ranged from 0.20 to 2.02 mg with an average value of 1.21 mg。Crude fat ranged from 40 to 48%with an average value of 44.8%.

The sesame meal is the main by-product during sesame oil manufacturing. Although sesame meal content 40~50% protein and lignan glycosides, it seldom use in food processing, mainly used as a fertilizer and feeds. The purpose of this research is to produce sesame soy sauce products from the sesame meal, after 180 day fermentation and aging at room temperature, the general compositions of sesame soy sauces were respectively described as following total nitrogen 1.55%, formol nitrogen 0.72%, amino nitrogen 0.58%, degree of hydrolysis 46.5%, total nitrogen ultilization ratio 71.2% and sodium chloride 17.1%. The content of protease and amylase activity in 1 g koji were 211±7 units and 67±1 units.

目 次 頁 次
目次……………………………………………………………………i
圖次………………………………………………………………………v
表次………………………………………………………………………vi
中文摘要……………………………………………………………………1
英文摘要(Abstract)………………………………………………………………2
第一章、 研究動機……………………………………………………………………4
第二章、 文獻整理………………………………………………………………………5
壹、 芝麻簡介………………………………………………………………………5
一、 芝麻之栽培環境與植物型態…………………………………………5
二、 芝麻一般組成分及特性……………………………………………………7
1. 油脂……………………………………………………………7
A. 芝麻油之一般特性…………………………………………………7
B. 芝麻油之脂肪酸組成及不皂化物…………………………………………7
C. 芝麻油之香氣成分…………………………………………………………7
D. 芝麻油之氧化安定性 ……………………………………………………8
2. 蛋白質………………………………………………………………8
3. 碳水化合物…………………………………………………………………8
4. 維生素及礦物質……………………………………………………………8
5. 木酚素(Lignans)……………………………………………………………9
貳、 Lignans及lignan glycosides之化學性質………………16
一、 Lignans之含量及化學性質………………………………16
二、 Lignan glycosides之含量及化學性質…………………16
參、 Lignans之分離純化………………………………………20
一、 Sesamin…………………………………………………20
二、 Sesaminol………………………………………………20
三、 Sesaminol triglucoside……………………………………………………21
四、 Sesaminol diglucoside…………………………………………………………22
五、 Sesamolinol diglucoside………………………………………………………22
肆、 芝麻之生理機能…………………………………………………………………26
一、 抗氧化活性………………………………………………………………………26
A. Lignans之抗氧化活性……………………………………………26
B. Lignan glycosides之抗氧化活性……………………………………27
二、 降低膽固醇……………………………………………………………………30
三、 調節脂肪酸之代謝…………………………………………………………30
四、 提升維生素E (tocopherol)含量………………………………………………33
五、 增強肝功能及促進酒精代謝………………………………………………33
六、 預防癌症…………………………………………………………………34
七、 防止高血壓………………………………………………………………34
八、 對老化之影響……………………………………………………………35
伍、 醬油簡介…………………………………………………………………36
一、 濃口(Koikuchi)醬油………………………………………………………36
二、 淡口(Usukuchi)醬油………………………………………………………36
三、 玉溜(Tamari)醬油……………………………………………………………36
四、 甘露(Saishikomi)醬油………………………………………………………37
五、 白露(Shiro)醬油………………………………………………………………37
第三章、 材料與方法…………………………………………………41
壹、 實驗架構……………………………………………………41
貳、 實驗材料與器材…………………………………………………………42
參、 實驗方法……………………………………………………………………44
一、 芝麻油中sesamin及sesamolin含量分析……………………………………44
二、 Sesamin及sesamolin檢量線製作……………………………………………44
三、 分離純化芝麻油中之sesamin及sesamolin………………………………44
四、 Sesaminol triglucoside標準品之製備…………………45
五、 Sesaminol triglucoside檢量線之製作…………………45
六、 不同溶劑對脫脂芝麻中sesaminol triglucoside之萃取效果……………46
七、 不同管柱層析法分離純化脫脂芝麻中之sesaminol triglucoside…………46
1. Lignan glycosides粗萃出物之製備………………………………………46
2. Diaion HP-20疏水性管柱層析…………………………………………46
3. Amberlite XAD-16疏水性管柱層析………………………………………46
4. Silica gel親水性管柱層析……………………………………………47
5. Silica gel管柱搭配Diaion HP-20管柱層析…………………………47
6. Cellulose管柱搭配Diaion HP-20管柱層析……………………………47
八、 不同品種芝麻之lignans及粗脂肪含量分析………………………………50
九、 芝麻粕一般成分分析………………………………………………………50
十、 芝麻醬油之釀造……………………………………………………50
十一、 醬油製造之相關分析…………………………………………………………52
1. 總氮(Total nitrogen，TN) ……………………………………………………52
2. 氨態氮(Ammonium nitrogen，Am-N) ……………………………………52
3. 甲醛態氮(Formol nitrogen，FN) ……………………………………………53
4. 胺基態氮(Amino nitrogen，AN) …………………………………………53
5. 蛋白質水解率(Degree of hydrolysis，DH) ………………………………53
6. 總氮利用率(Total nitrogen ultilization ratio，TNUR) ……………………53
7. 胺基態氮/總氮百分比………………………………………………………54
8. 氯化鈉之定量………………………………………………………………54
9. pH值……………………………………………………………………54
10. 蛋白酶活性之測定………………………………………………………54
11. 澱粉酶活性之測定………………………………………………………56
第四章、 結果與討論………………………………………58
一、 Sesamin、sesamolin及sesaminol triglucoside檢量線之製作……58
二、 利用矽膠管柱層析對芝麻油中sesamin及sesamolin之純化結果…58
三、 不同品種芝麻之lignans及粗脂肪含量………………59
四、 不同溶劑對脫脂芝麻中sesaminol triglucoside之萃取效果………60
五、 利用不同管柱層析法分離純化sesaminol triglucoside之效果…………60
六、 芝麻粕一般成分分析……………………………60
七、 芝麻醬油出麴料之酵素活性………………………………70
八、 芝麻醬油釀造期間一般組成之變化………………………71
第五章、 結論…………………………………………………………73
第六章、 參考文獻……………………………………………………74

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