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The chemical composition of Pinus morrisonicola Hayata, Pinus taiwanensis Hayata and their endophyte-fermented liquor and the identification of voltage-operated calcium channel blockers form the needle of Pinus morrisonicola Hayata through the calcium fluorescent signal in rat vascular smooth muscle cell
|關鍵字:||台灣五葉松;台灣二葉松;鈣離子螢光;電位控制鈣離子通道;高血壓;P. morrisonicola Hayata;P. taiwanensis Hayata;calcium fluorescent;voltage-operated calcium channel;hypertension||引用:||Research background  Wilson JP, Knoll AH, Holbrook NM, Marshall CR. Modeling fluid flow in Medullosa, an anatomically unusual Carboniferous seed plant. Paleobiology 2008;34:472-93.  Missouri Botanical Garden, 2017. Available at http://www.missouribotanicalgarden.org/2017 Accessed May 22, 2017.  McCormick JA, John W. A subdioecioius population of Pinus cembroides in southeast Arizona. Ohio Sci 1963;63:159-63.  Flores-Renteria L, Molina-Freaner F, Whipple AV, Gehring CA, Dominguez CA. Sexual stability in the nearly dioecious Pinus Johannis (Pinaceae). Am J Bot 2013;100:602-12.  Li B, Shen YH, He YR, Zhang WD. Chemical constituents and biological activities of Pinus species. Chem Biodivers 2013;10:2133-60.  Packer L, Rimbach G, Virgili F. 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松為松科植物的總稱，屬於常綠喬木，少部分為矮小灌木，葉部常成針狀。松樹的藥用功效不管在東方或是西方典籍中皆早有記載。台灣地區也分布了許多不同種類的松樹，其中台灣五葉松(Pinus morrisonicola Hayata)以及台灣二葉松(Pinus taiwanensis Hayata)廣泛分布於台灣山區並且皆屬於台灣特有種。台灣五葉松及台灣二葉松長久以來被民間作為保健食品，傳統使用上常直接將松葉製成松葉茶或是額外加入砂糖製成松發酵液或是松醋。本論文研究主題第一部分主要目的在研究台灣五葉松及台灣二葉松以及其內生菌發酵液的化學二次代謝物成分，期望對這兩種台灣特有種的二次代謝物背景以及其經過長時間發酵後的化學變化有所了解，以利未來對於發酵物活性功效的開發。第二部分主要研究台灣五葉松松針萃取物對於降血壓效果的開發，並鑑定具有降血壓活性的二次代謝物。
在第一部分研究中，我們利用液相層析質譜儀從兩種松葉中鑑定出了27種多酚類化合物，主要由兒茶素類、原花青素類、黃酮類、木質素所構成，某些結構上還接有不同糖基化或酚酸醯化修飾；而透過氣相層析質譜儀中，我們發現了60種揮發性成分，主要包含有機酸、酯類、萜類、醯胺類及醇類化合物。在經過長時間的內生菌發酵轉換後，主要多酚類化合物下降為12種，包含黃酮類糖苷及木質素糖苷；而揮發性成分部分也下降為29種，主要是有機酸類及醇類化合物，並生成出萜二醇 (terpin) 此一具有緩解咳嗽效果的活性成分。透過對於其二次代謝物的了解，未來能夠對於發酵液在發酵過程中有所調控，有利於其未來活性的開發。
在第二部分研究中，由於長久以來台灣五葉松松葉常應用於緩解高血壓所產生的症狀，因此利用大鼠主動脈平滑肌細胞株(A7r5)的鈣離子螢光平台，來觀察松葉萃取物對於細胞內鈣離子濃度的影響。透過螢光實驗、質譜及NMR發現到五葉松中的icariside E4，(7'R, 8'S)-7'-(3',4'-dimethoxyphenyl)-3-hydroxy-8'-hydroxymethyl- 7',8'-dihydrobenzofuran-1-propanol 9'-O-α-L-arabinofuranoside及kaempferol coumaroyl-glucose-rhamnoside具有抑制電位控制鈣離子通道的開啟，來抑制鈣離子進入血管平滑肌細胞中。這些多酚類化合物具有潛力成為新一代的鈣離子通道抑制劑，用於治療高血壓的症狀。
Pine plant belongs to the genus Pinus. It is an evergreen ligneous plant with many pharmacological effects. In Taiwan, P. morrisonicola Hayata and P. taiwanensis Hayata are endemic species and widely distributed around mountain area. Both of their needles and branches served as functional food for local people for decades and the traditional way to prepared them are directly extract with hot water or fermented with sugar through long period process to produce alcoholic drinks or vinegar. This thesis consists of two parts: I. Identification and comparison of phenolic and aromatic constituents in needles of two pine species and their endophyte-fermented liquor. II. Isolation of neolignans and acylated flavonoid glucoside from the needle of P. morrisonicola Hayata and the inhibition of cytoplasmic Ca2+ concentrate in A7r5 vascular smooth muscle cell.
In the first part, there are 27 phenolic and 60 aromatic compounds were identified in the fresh young needles. The phenolic compounds were mainly composed of catechins, procyandins, flavonoids, and lignans attached with glycoside or acylated glycoside. Organic acids, esters, terpenes, amides, and alcohols were the major aromatic compounds. In contrast, 12 phenolic and 29 aromatic compounds were identified in the endophyte-fermented liquor and found to be drastic different from those compounds in the original young needles; the main phenolic compounds were aglycones of flavonoids and lignin while the major aromatic compounds were organic acids and alcohols. High content of terpin were also discovered in the endophyte-fermented liquor.
In the second part, two dihydrobenzofuran lignan, icariside E4 and (7'R, 8'S)-7'-(3',4'-dimethoxyphenyl)-3-hydroxy-8'-hydroxymethyl- 7',8'-dihydrobenzofuran-1-propanol 9'-O-α-L-arabinofuranoside and one acylated flavonoid glucoside, Kaempferol coumaroyl-glucose-rhamnoside were isolated and identified from the needle of P. morrisonicola Hayata. All of the compounds inhibit cytosolic calcium increase (calcium fluorescent) through blocking the voltage-operated calcium channel (VOCC) in A7r5 cell (a Rattus norvegicus aorta smooth muscle cell). These compounds could be promising candidates for further application as a VOCC inhibitor for the new treatment of hypertension.
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