Alnus속 식물은 우리나라에 널리 자생하는 중요한 의약 자원 식물이며 이들 식물들의 주요성분으로 판단되는 diarylheptanoid 화합물들은 항산화 및 암예방효과 이외에도 직접적인 항암활성이 있는 것으로 추정된다. 본 연구에서는 국내 주요한 Alnus속 식물의 자생종인 오리나무 A. japonica 수피로부터 Diarylheptanoid 화합물을 분리하고 그 ...
Alnus속 식물은 우리나라에 널리 자생하는 중요한 의약 자원 식물이며 이들 식물들의 주요성분으로 판단되는 diarylheptanoid 화합물들은 항산화 및 암예방효과 이외에도 직접적인 항암활성이 있는 것으로 추정된다. 본 연구에서는 국내 주요한 Alnus속 식물의 자생종인 오리나무 A. japonica 수피로부터 Diarylheptanoid 화합물을 분리하고 그 화학 구조를 결정하여 이들 화합물에 대한 각종 cancer cell line에 대한 cytotoxic activity를 연구 하였으며 의약품 자원으로서의 가능성을 판단하기 위해 국내에 자생하는 주요 Alnus속 식물에 대한 diarylheptanoid 화합물의 함유량을 검토하였다. 먼저, 오리나무 A. japonica 수피로부터 Diarylheptanoid 화합물의 분리 및 구조결정 (제 1 장)을 시도하여 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-β-D-glucopyranosyl (1→3)-β-D-xylopyranoside(1), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-β-D-apiofuranosyl(1→6)-β-D-glucopyranoside(2) ,1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-β-D-glucopyranoside (3), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane (4), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-β-D-glucopyranoside (5), oregonin (6), hirsutanonol (7), hirsutenone (8), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-O-β-D-xylopyranoside (9) and platyphylloside (10) 로 그 구조를 결정 하였으며 그중 compound 1 과 9는 신물질로 확인되었다. 또한, 오리나무 A. japonica 수피에서 분리한 diarylheptanoid의 항암활성 (제 2 장)을 연구하여 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyl-2H-tetrazalium bromide (MTT)를 이용한 방법으로 A. japonica 수피에서 분리한 10종의 diarylheptanoid 화합물들의 mouse melanoma 및 3종의 cancer cell line에 대한 세포독성을 검색하였으며 그 결과 이들 10종의 화합물이 murine B16 melanoma cell 및 human SNU-1 gastric cancer cell line에 대하여 강력한 항암활성을 나타내었으며 human SNU-354 hepatoma cell과 human SNU-C4 colorectal cell line에 대해서는 화합물 7 및 10 만이 강력한 효과를 나타내었다. 한편, 오리나무 Aluns속 식물의 diarylheptanoid 화합물의 함량분석 (제 3 장)을 시도하여 Alnus속 식물의 주요 생리활성성분으로 판단되는 diarylheptanoid 배당체인 oregonin과 그의 aglycone인 hirsutanonol에 대하여 국내 자생주요 오리나무속 식물인 오리나무 A. japonica, 물오리나무 A. hirsuta, 물갬나무 A. hirsuta var. sibirica의 수피중의 함량을 HPLC를 통해 측정하였으며 그 결과 3종의 모든 Alnus속 식물의 수피는 diarylheptanoid의 풍부한 자원이며 특히 물오리나무 A. hirsuta의 수피에는 oregonin이 물갬나무 A.hirsuta var sibirica의 수피에서는 hirsutanonol이 많이 함유된 것을 확인하였다.
Alnus속 식물은 우리나라에 널리 자생하는 중요한 의약 자원 식물이며 이들 식물들의 주요성분으로 판단되는 diarylheptanoid 화합물들은 항산화 및 암예방효과 이외에도 직접적인 항암활성이 있는 것으로 추정된다. 본 연구에서는 국내 주요한 Alnus속 식물의 자생종인 오리나무 A. japonica 수피로부터 Diarylheptanoid 화합물을 분리하고 그 화학 구조를 결정하여 이들 화합물에 대한 각종 cancer cell line에 대한 cytotoxic activity를 연구 하였으며 의약품 자원으로서의 가능성을 판단하기 위해 국내에 자생하는 주요 Alnus속 식물에 대한 diarylheptanoid 화합물의 함유량을 검토하였다. 먼저, 오리나무 A. japonica 수피로부터 Diarylheptanoid 화합물의 분리 및 구조결정 (제 1 장)을 시도하여 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-β-D-glucopyranosyl (1→3)-β-D-xylopyranoside(1), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-β-D-apiofuranosyl(1→6)-β-D-glucopyranoside(2) ,1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-β-D-glucopyranoside (3), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane (4), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-β-D-glucopyranoside (5), oregonin (6), hirsutanonol (7), hirsutenone (8), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-O-β-D-xylopyranoside (9) and platyphylloside (10) 로 그 구조를 결정 하였으며 그중 compound 1 과 9는 신물질로 확인되었다. 또한, 오리나무 A. japonica 수피에서 분리한 diarylheptanoid의 항암활성 (제 2 장)을 연구하여 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyl-2H-tetrazalium bromide (MTT)를 이용한 방법으로 A. japonica 수피에서 분리한 10종의 diarylheptanoid 화합물들의 mouse melanoma 및 3종의 cancer cell line에 대한 세포독성을 검색하였으며 그 결과 이들 10종의 화합물이 murine B16 melanoma cell 및 human SNU-1 gastric cancer cell line에 대하여 강력한 항암활성을 나타내었으며 human SNU-354 hepatoma cell과 human SNU-C4 colorectal cell line에 대해서는 화합물 7 및 10 만이 강력한 효과를 나타내었다. 한편, 오리나무 Aluns속 식물의 diarylheptanoid 화합물의 함량분석 (제 3 장)을 시도하여 Alnus속 식물의 주요 생리활성성분으로 판단되는 diarylheptanoid 배당체인 oregonin과 그의 aglycone인 hirsutanonol에 대하여 국내 자생주요 오리나무속 식물인 오리나무 A. japonica, 물오리나무 A. hirsuta, 물갬나무 A. hirsuta var. sibirica의 수피중의 함량을 HPLC를 통해 측정하였으며 그 결과 3종의 모든 Alnus속 식물의 수피는 diarylheptanoid의 풍부한 자원이며 특히 물오리나무 A. hirsuta의 수피에는 oregonin이 물갬나무 A.hirsuta var sibirica의 수피에서는 hirsutanonol이 많이 함유된 것을 확인하였다.
Diarylheptanoids from the Bark of Alnus japonica Steudel and Their Anticancer Activities Alnus species are deciduous board-leaved trees or shrubs found in the damp place and mountain and more than 17 species are growing in Korea. The bark of Alnus japonica has been used of fever, hemorrhage and diar...
Diarylheptanoids from the Bark of Alnus japonica Steudel and Their Anticancer Activities Alnus species are deciduous board-leaved trees or shrubs found in the damp place and mountain and more than 17 species are growing in Korea. The bark of Alnus japonica has been used of fever, hemorrhage and diarrehea in oriental traditional medicine. This research was focused on the diarylheptanoid from the bark of A. japonica and its anticancer activities on various cancer cell line. Besides, the quantitive analysis of diarylheptanoid was conducted in the Alnus species to evaluate its values as phamaceutical resources. In chapter 1, phytochemical examination of the leaves of Alnus japonica Steudel, one of the indigenous Alnus species growing in Korea has led to the isolation of ten diarylheptanoids. Structures of these diarylheptanoids are elucidated as 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-β-D-glucopyranosyl(1→3)-β-D-xylopyranoside(1),1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-β-D-apiofuranosyl(1→6)-β-D-glucopyranoside(2) ,1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-β-D-glucopyranoside (3), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane (4), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-β-D-glucopyranoside (5), oregonin (6), hirsutanonol (7), hirsutenone (8), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-O-β-D-xylopyranoside (9) and platyphylloside (10) on the basis of physico-chemical and instrumental analysis. Among them, Compounds 1 and 9 were found to be novel diarylheptanoids. In chapter 2, antitumor activities of these ten compounds were evaluated against murine B16 melanoma cell, human SNU-1 gastric cancer cell, human SNU-354 hepatoma cancer cell and human SNU-C4 colorectal cell line. All ten diarylheptanoids showed potent cytotoxic activities against murine B16 melanoma cell and human SNU-C1 gastric cancer cell when measured the cell viabilities by MTT assay. However, antitumor activities were exerted only by compound 7 and 10 against human SNU-354 hepatoma cancer cell and human SNU-C4 colorectal cell line. These results suggest that diarylheptanoids from the bark of A. japonica could be a potent anticancer agent and further developed as anticancer drugs. In chapter 3, quantitative analysis of diarylheptanoids(oregonin and hirsutanonol), which were characteristic components of Alnus species (A. japonica, A. hirsuta and A. hirsuta var. sibirica), has been conducted by HPLC. The results showed that these Alnus species were rich source of those compounds and the amount of oregonin and hirsutanonol showed seasonal variation.
Diarylheptanoids from the Bark of Alnus japonica Steudel and Their Anticancer Activities Alnus species are deciduous board-leaved trees or shrubs found in the damp place and mountain and more than 17 species are growing in Korea. The bark of Alnus japonica has been used of fever, hemorrhage and diarrehea in oriental traditional medicine. This research was focused on the diarylheptanoid from the bark of A. japonica and its anticancer activities on various cancer cell line. Besides, the quantitive analysis of diarylheptanoid was conducted in the Alnus species to evaluate its values as phamaceutical resources. In chapter 1, phytochemical examination of the leaves of Alnus japonica Steudel, one of the indigenous Alnus species growing in Korea has led to the isolation of ten diarylheptanoids. Structures of these diarylheptanoids are elucidated as 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-β-D-glucopyranosyl(1→3)-β-D-xylopyranoside(1),1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-β-D-apiofuranosyl(1→6)-β-D-glucopyranoside(2) ,1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-β-D-glucopyranoside (3), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane (4), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-β-D-glucopyranoside (5), oregonin (6), hirsutanonol (7), hirsutenone (8), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-O-β-D-xylopyranoside (9) and platyphylloside (10) on the basis of physico-chemical and instrumental analysis. Among them, Compounds 1 and 9 were found to be novel diarylheptanoids. In chapter 2, antitumor activities of these ten compounds were evaluated against murine B16 melanoma cell, human SNU-1 gastric cancer cell, human SNU-354 hepatoma cancer cell and human SNU-C4 colorectal cell line. All ten diarylheptanoids showed potent cytotoxic activities against murine B16 melanoma cell and human SNU-C1 gastric cancer cell when measured the cell viabilities by MTT assay. However, antitumor activities were exerted only by compound 7 and 10 against human SNU-354 hepatoma cancer cell and human SNU-C4 colorectal cell line. These results suggest that diarylheptanoids from the bark of A. japonica could be a potent anticancer agent and further developed as anticancer drugs. In chapter 3, quantitative analysis of diarylheptanoids(oregonin and hirsutanonol), which were characteristic components of Alnus species (A. japonica, A. hirsuta and A. hirsuta var. sibirica), has been conducted by HPLC. The results showed that these Alnus species were rich source of those compounds and the amount of oregonin and hirsutanonol showed seasonal variation.
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