식용으로 쓰이는 국내외 연자육과 연근의 에탄올 추출물에 대해 항산화 효과 및 지방산과 식물성 스테롤 성분을 연구하였다. 항산화 효과를 측정하기 위해서 국내외 연자육과 연근을 70% 에탄올과 헥산으로 추출하여 분석하였다. DPPH 라디칼 소거 활성, ...
식용으로 쓰이는 국내외 연자육과 연근의 에탄올 추출물에 대해 항산화 효과 및 지방산과 식물성 스테롤 성분을 연구하였다. 항산화 효과를 측정하기 위해서 국내외 연자육과 연근을 70% 에탄올과 헥산으로 추출하여 분석하였다. DPPH 라디칼 소거 활성, 총 페놀, 총 플라보노이드를 측정하였다. 가장 좋은 항산화 효과를 갖는 연자육으로서 베트남 연자육은 비타민 C의 4.3%에 해당하는 항산화 효과를 갖고 있으며 가장 좋은 항산화 효과를 갖는 시흥 연근은 비타민 C의 12.0%에 해당하는 항산화 효과를 보였다. 연자육보다 연근이 더 좋은 항산화 효과를 갖다는 것을 확인하였다. 그리고 항산화 효과, 총 페놀 함량, 총 플라보노이드 함량은 연근과 연자육의 종류, 생산지에 따라서 다르게 나타났다. 시흥 연자육과 연근을 95% 에탄올로 추출하고 건조한 후에 다시 헥산으로 추출하여 추출엑을 말린 다음 가수분해를 하였다. 추출된 지방산과 식물성 스테롤 성분은 GC-MS로 분석하였다. 연에 가장 많이 들어있는 지방산은 linoleic acid이고 가장 많은 phytosterol은 β-sitosterol이었다. Total fatty acid와 total phytosterol은 연근보다 연자육에 더 많이 포함되어 있었다. 본 연구에서 phthalimide, maleic anhydride, tartaric anhydride and succinic anhydride룰 사용하여 2-Allyl-isoindole-1,3-dione, 1-Allylpyrrole-2,5-dione, N-Allyltartarimide와 1-Allylpyrrolidine-2,5- dione와 같은 cyclic allylimide를 합성하였다. 그 다음 zinc 을 매개로 Barbier-type propargylation 을 해서 1-Allyl-5-hydroxy-5- prop-2- ynyl-1,5-dihydropyrrol-2-one, 1-Allyl-5-hydroxy-5-prop-2-ynyl-1, 5-dihydropyrrol-2-one, 1-Allyl-5-hydroxy-5-prop-2-ynyl-pyrrolidin-2- one와 Acetic acid 4-acetoxy-1-allyl-5-hydroxy-2-oxo-5-prop-2-ynyl- pyrrolidin-3-yl ester와 같은 1-allyl-5-hydroxy-5- prop-2- ynylpyrrolidin-2-one analogue를 얻었다. 얻은 생성물을 가지고 Co2(CO)8를 촉매로 Paosun-Kand 반응해서 (4aR*)-1,2,4a,5-Tetrahydro-4H-3a-aza-s-indacene-3,6-dione,(4aR*, 8aR)- 4a-Hydroxy-4,4a,10,10a-tetrahydro-1H-9a-azacyclopenta[b]fluorene-2,9- dione와 (4aR*, 8aR)-Acetic acid 2-acetoxy-8a-hydroxy-3,6-dioxo-2,3, 4,4a,5,6,8,8a-octahydro-1H-3a-aza-s-indacen-1-yl ester와 같은 tricyclic hydroxy gama-lactam을 합성하였다. (4aR*, 8aR)-4a-Hydroxy-4,4a,10,10a-tetrahydro-1H-9a-azacyclopenta[b] luorene-2,9-dione와 (4aR*, 8aR)-Acetic acid 2-acetoxy-8a-hydroxy-3,6-dioxo-2,3,4,4a,5,6,8,8a-octahydro-1H-3a-aza-s-indacen-1-yl ester와 같은 hydroxy gama-lactam을 이용하여 촉매수소화 반응을 시킨 결과 (4aR*, 7aS,8aR)-4a-Hydroxy-3,3a,4,4a,10,10a-hexahydro-1H-9a-azacyclopenta[b] fluorene-2,9-dione와 (4aR*, 7aS, 8aR)-Acetic acid 1-acetoxy-8a-hydroxy- 3,6-dioxo-decahydro-3a-aza-s-indacen-2-yl ester를 얻었다. Hydroxy gama-lactam을 탈수 반응, 촉매 수소화 반응 순으로 시켰더니 (4aR*, 7aS, 8aS)-3,3a,4,4a,10,10a-Hexahydro-1H-9a-azacyclopenta[b]fluorene-2,9-dione 와 (4aR*, 7aS, 8aS)-Octahydro-3a-aza-s-indacene-3,6-dione를 합성하였다. 최종 생성물의 입체화학을 알기 위한 COSY, HETCOR, 1D-homodecoupling, NOE (Nuclear Overhauser Effect)와 같은 NMR spectroscopic technique을 사용하였고 계산 화학적 방법으로는 GAUSSIAN 09 프로그램도 이용하였다.
식용으로 쓰이는 국내외 연자육과 연근의 에탄올 추출물에 대해 항산화 효과 및 지방산과 식물성 스테롤 성분을 연구하였다. 항산화 효과를 측정하기 위해서 국내외 연자육과 연근을 70% 에탄올과 헥산으로 추출하여 분석하였다. DPPH 라디칼 소거 활성, 총 페놀, 총 플라보노이드를 측정하였다. 가장 좋은 항산화 효과를 갖는 연자육으로서 베트남 연자육은 비타민 C의 4.3%에 해당하는 항산화 효과를 갖고 있으며 가장 좋은 항산화 효과를 갖는 시흥 연근은 비타민 C의 12.0%에 해당하는 항산화 효과를 보였다. 연자육보다 연근이 더 좋은 항산화 효과를 갖다는 것을 확인하였다. 그리고 항산화 효과, 총 페놀 함량, 총 플라보노이드 함량은 연근과 연자육의 종류, 생산지에 따라서 다르게 나타났다. 시흥 연자육과 연근을 95% 에탄올로 추출하고 건조한 후에 다시 헥산으로 추출하여 추출엑을 말린 다음 가수분해를 하였다. 추출된 지방산과 식물성 스테롤 성분은 GC-MS로 분석하였다. 연에 가장 많이 들어있는 지방산은 linoleic acid이고 가장 많은 phytosterol은 β-sitosterol이었다. Total fatty acid와 total phytosterol은 연근보다 연자육에 더 많이 포함되어 있었다. 본 연구에서 phthalimide, maleic anhydride, tartaric anhydride and succinic anhydride룰 사용하여 2-Allyl-isoindole-1,3-dione, 1-Allylpyrrole-2,5-dione, N-Allyltartarimide와 1-Allylpyrrolidine-2,5- dione와 같은 cyclic allylimide를 합성하였다. 그 다음 zinc 을 매개로 Barbier-type propargylation 을 해서 1-Allyl-5-hydroxy-5- prop-2- ynyl-1,5-dihydropyrrol-2-one, 1-Allyl-5-hydroxy-5-prop-2-ynyl-1, 5-dihydropyrrol-2-one, 1-Allyl-5-hydroxy-5-prop-2-ynyl-pyrrolidin-2- one와 Acetic acid 4-acetoxy-1-allyl-5-hydroxy-2-oxo-5-prop-2-ynyl- pyrrolidin-3-yl ester와 같은 1-allyl-5-hydroxy-5- prop-2- ynylpyrrolidin-2-one analogue를 얻었다. 얻은 생성물을 가지고 Co2(CO)8를 촉매로 Paosun-Kand 반응해서 (4aR*)-1,2,4a,5-Tetrahydro-4H-3a-aza-s-indacene-3,6-dione,(4aR*, 8aR)- 4a-Hydroxy-4,4a,10,10a-tetrahydro-1H-9a-azacyclopenta[b]fluorene-2,9- dione와 (4aR*, 8aR)-Acetic acid 2-acetoxy-8a-hydroxy-3,6-dioxo-2,3, 4,4a,5,6,8,8a-octahydro-1H-3a-aza-s-indacen-1-yl ester와 같은 tricyclic hydroxy gama-lactam을 합성하였다. (4aR*, 8aR)-4a-Hydroxy-4,4a,10,10a-tetrahydro-1H-9a-azacyclopenta[b] luorene-2,9-dione와 (4aR*, 8aR)-Acetic acid 2-acetoxy-8a-hydroxy-3,6-dioxo-2,3,4,4a,5,6,8,8a-octahydro-1H-3a-aza-s-indacen-1-yl ester와 같은 hydroxy gama-lactam을 이용하여 촉매수소화 반응을 시킨 결과 (4aR*, 7aS,8aR)-4a-Hydroxy-3,3a,4,4a,10,10a-hexahydro-1H-9a-azacyclopenta[b] fluorene-2,9-dione와 (4aR*, 7aS, 8aR)-Acetic acid 1-acetoxy-8a-hydroxy- 3,6-dioxo-decahydro-3a-aza-s-indacen-2-yl ester를 얻었다. Hydroxy gama-lactam을 탈수 반응, 촉매 수소화 반응 순으로 시켰더니 (4aR*, 7aS, 8aS)-3,3a,4,4a,10,10a-Hexahydro-1H-9a-azacyclopenta[b]fluorene-2,9-dione 와 (4aR*, 7aS, 8aS)-Octahydro-3a-aza-s-indacene-3,6-dione를 합성하였다. 최종 생성물의 입체화학을 알기 위한 COSY, HETCOR, 1D-homodecoupling, NOE (Nuclear Overhauser Effect)와 같은 NMR spectroscopic technique을 사용하였고 계산 화학적 방법으로는 GAUSSIAN 09 프로그램도 이용하였다.
Part Ⅰ. The experiments were carried out to analyze the antioxidative components, fatty acids and phytosterols present in the ethanol extracts of lotus roots and seeds from various growing regions. First, we compared the antioxidant activity of the 70% ethanol extracts of lotus roots and seeds from ...
Part Ⅰ. The experiments were carried out to analyze the antioxidative components, fatty acids and phytosterols present in the ethanol extracts of lotus roots and seeds from various growing regions. First, we compared the antioxidant activity of the 70% ethanol extracts of lotus roots and seeds from various growing regions. The free radical scavenging activity, total phenolic and flavonoid content of the samples was measured. The best antioxidant activity of the samples was in roots from Siheung, seeds from Vietnam, respectively. And the roots showed better antioxidant activity than the seeds. The antioxidant activity, total phenolic and flavonoid content varied in lotus roots and seeds from different growing regions. Second, the fatty acids and phytosterols were extracted from the Siheung lotus roots and seeds with 95% ethanol followed by hexane. The hexane extracts were hydrolyzed, derivatized to TMS derivatives and then fatty acid and phytosterol contents were analyzed by GC-MS. Linoleic acid was the most abundant fatty acid, β-sitosterol was the main phytosterol in both lotus roots and seeds. Part Ⅱ. In this study the cyclic allylimides such as 2-Allyl-isoindole-1,3-dione, 1-Allylpyrrole-2,5-dione, N-Allyltartarimide and 1-Allylpyrrolidine-2,5- dione were prepared from phthalimide, maleic anhydride, tartaric anhydride and succinic anhydride, respectively. And then zinc-mediated Barbier-type propargylation were carried out to obtained 1-allyl 5- hydroxy-5-prop-2-ynylpyrrolidin-2-one analogues such as 1-Allyl-5- hydroxy-5-prop-2-ynyl-1,5-dihydropyrrol-2-one, 1-Allyl-5-hydroxy-5- prop-2-ynyl-1,5-dihydropyrrol-2-one, 1-Allyl-5-hydroxy-5-prop-2-ynyl- pyrrolidin-2-one and Acetic acid 4-acetoxy-1-allyl-5-hydroxy-2-oxo-5- prop-2-ynyl- pyrrolidin-3-yl ester subsequently. Pauson-Khand reaction of 1-allyl-5-hydroxy-5-prop-2-ynylpyrrolidin- 2-one analogues gave tricyclic hydroxy gama-lactams such as (4aR*)-1,2,4a,5-Tetrahydro-4H-3a-aza-s-indacene-3,6-dione,(4aR*, 8aR)- 4a-Hydroxy-4,4a,10,10a-tetrahydro-1H-9a-azacyclopenta[b]fluorene-2,9- dione, and (4aR*, 8aR)-Acetic acid 2-acetoxy-8a-hydroxy-3,6-dioxo-2,3, 4,4a,5,6,8,8a-octahydro-1H-3a-aza-s-indacen-1-yl ester in moderate yields. Catalytic hydrogenation of hydroxy gama-lactam such as (4aR*, 8aR)-4a-Hydroxy-4,4a,10,10a-tetrahydro-1H-9a-azacyclopenta[b]fluorene- 2,9-dione and (4aR*, 8aR)-Acetic acid 2-acetoxy-8a-hydroxy-3,6-dioxo- 2,3,4,4a,5,6,8,8a-octahydro-1H-3a-aza-s-indacen-1-yl ester gave (4aR*, 7aS,8aR)-4a-Hydroxy-3,3a,4,4a,10,10a-hexahydro-1H-9a- azacyclopenta[b]fluorene-2,9-dione and (4aR*, 7aS, 8aR)-Acetic acid 1- acetoxy-8a-hydroxy-3,6-dioxo-decahydro-3a-aza-s-indacen-2-yl ester. Dehydration followed by catalytic hydrogenation of hydroxy gama-lactam analogues gave (4aR*, 7aS, 8aS)-3,3a,4,4a,10,10a-Hexahydro-1H-9a- azacyclopenta[b]fluorene-2,9-dione and (4aR*, 7aS, 8aS)-Octahydro-3a- aza-s-indacene-3,6-dione. The conformation of the products were identified using the NMR spectroscopic techniques such as COSY, HETCOR, 1D-homodecoupling, NOE (Nuclear Overhauser Effect) experiment and confirmed by comparison with NMR calculation data using GAUSSIAN 09 program.
Part Ⅰ. The experiments were carried out to analyze the antioxidative components, fatty acids and phytosterols present in the ethanol extracts of lotus roots and seeds from various growing regions. First, we compared the antioxidant activity of the 70% ethanol extracts of lotus roots and seeds from various growing regions. The free radical scavenging activity, total phenolic and flavonoid content of the samples was measured. The best antioxidant activity of the samples was in roots from Siheung, seeds from Vietnam, respectively. And the roots showed better antioxidant activity than the seeds. The antioxidant activity, total phenolic and flavonoid content varied in lotus roots and seeds from different growing regions. Second, the fatty acids and phytosterols were extracted from the Siheung lotus roots and seeds with 95% ethanol followed by hexane. The hexane extracts were hydrolyzed, derivatized to TMS derivatives and then fatty acid and phytosterol contents were analyzed by GC-MS. Linoleic acid was the most abundant fatty acid, β-sitosterol was the main phytosterol in both lotus roots and seeds. Part Ⅱ. In this study the cyclic allylimides such as 2-Allyl-isoindole-1,3-dione, 1-Allylpyrrole-2,5-dione, N-Allyltartarimide and 1-Allylpyrrolidine-2,5- dione were prepared from phthalimide, maleic anhydride, tartaric anhydride and succinic anhydride, respectively. And then zinc-mediated Barbier-type propargylation were carried out to obtained 1-allyl 5- hydroxy-5-prop-2-ynylpyrrolidin-2-one analogues such as 1-Allyl-5- hydroxy-5-prop-2-ynyl-1,5-dihydropyrrol-2-one, 1-Allyl-5-hydroxy-5- prop-2-ynyl-1,5-dihydropyrrol-2-one, 1-Allyl-5-hydroxy-5-prop-2-ynyl- pyrrolidin-2-one and Acetic acid 4-acetoxy-1-allyl-5-hydroxy-2-oxo-5- prop-2-ynyl- pyrrolidin-3-yl ester subsequently. Pauson-Khand reaction of 1-allyl-5-hydroxy-5-prop-2-ynylpyrrolidin- 2-one analogues gave tricyclic hydroxy gama-lactams such as (4aR*)-1,2,4a,5-Tetrahydro-4H-3a-aza-s-indacene-3,6-dione,(4aR*, 8aR)- 4a-Hydroxy-4,4a,10,10a-tetrahydro-1H-9a-azacyclopenta[b]fluorene-2,9- dione, and (4aR*, 8aR)-Acetic acid 2-acetoxy-8a-hydroxy-3,6-dioxo-2,3, 4,4a,5,6,8,8a-octahydro-1H-3a-aza-s-indacen-1-yl ester in moderate yields. Catalytic hydrogenation of hydroxy gama-lactam such as (4aR*, 8aR)-4a-Hydroxy-4,4a,10,10a-tetrahydro-1H-9a-azacyclopenta[b]fluorene- 2,9-dione and (4aR*, 8aR)-Acetic acid 2-acetoxy-8a-hydroxy-3,6-dioxo- 2,3,4,4a,5,6,8,8a-octahydro-1H-3a-aza-s-indacen-1-yl ester gave (4aR*, 7aS,8aR)-4a-Hydroxy-3,3a,4,4a,10,10a-hexahydro-1H-9a- azacyclopenta[b]fluorene-2,9-dione and (4aR*, 7aS, 8aR)-Acetic acid 1- acetoxy-8a-hydroxy-3,6-dioxo-decahydro-3a-aza-s-indacen-2-yl ester. Dehydration followed by catalytic hydrogenation of hydroxy gama-lactam analogues gave (4aR*, 7aS, 8aS)-3,3a,4,4a,10,10a-Hexahydro-1H-9a- azacyclopenta[b]fluorene-2,9-dione and (4aR*, 7aS, 8aS)-Octahydro-3a- aza-s-indacene-3,6-dione. The conformation of the products were identified using the NMR spectroscopic techniques such as COSY, HETCOR, 1D-homodecoupling, NOE (Nuclear Overhauser Effect) experiment and confirmed by comparison with NMR calculation data using GAUSSIAN 09 program.
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#Pauson-Kkand 반응 다중 고리 락탐 유도체 입체 화학 GAUSSIAN 09 프로그램
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건국대학교 대학원
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2015
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Pauson-Kkand 반응 다중 고리 락탐 유도체 입체 화학 GAUSSIAN 09 프로그램
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