环草石斛多酚成份及其生物活性
|
摘要
为了研究环草石斛酚类成分及其生物活性,采用多种色谱技术对环草石斛丙酮(φ=80%)提取物进行了分离,所得化合物采用质谱、核磁等波谱技术进行了结构解析,并评价了各化合物的抗氧化、α-葡萄糖苷酶抑制及抗炎等活性。结果共分离鉴定了15个酚类物质,分别是chrysotoxol A(1)、neoechinulin A(2)、3,6,9-三羟基-3,4-二氢蒽-1(2H)-酮(3)、4,4′-二羟基-3,5-二甲氧基联苄(4)、柚皮素(5)、5,4′-二羟基-7,3′,5′-三甲氧基黄烷酮(6)、5,7,4′-三羟基-3′,5′-二甲氧基黄烷酮(7)、batatasin-III(8)、3,3′,5-三羟基联苄(9)、trigonopol B(10)、丁香脂素(11)、2,4,7-三羟基-9,10-二氢菲(12)、loddigesiinol B(13)、loddigesiinol I(14)、loddigesiinol J(15);其中化合物1-11为首次分自环草石斛的多酚。在所选实验条件下,化合物1-4、6、7、12的生物活性为首次评价;化合物1、3、12的强抗氧化活性,1、9的强α-葡萄糖苷酶抑制活性,1、12、14、15的强抗炎活性为首次报道。
To study the polyphenols from Dendrobium loddigesii and their biological activities, the 80% acetone extract from D. loddigesii was isolated and purified by chromatography techniques; the structures of obtained compounds were identified with spectroscopic techniques; the antioxidative, α-glucosidase inhibitory and anti-inflammatory activities of compounds were evaluated. Fifteen compounds were isolated and identified as chrysotoxol A(1), neoechinulin A(2), 3,6,9-trihydroxy-3,4-dihydroanthracen-1(2 H)-one(3), 4,4′-dihydroxyl-3,5-dimethoxylbibenzyl(4), naringenin(5), 5,4′-dihydroxy-7,3′,5′-trimethoxyflavanone(6), 5,7,4′-trihydroxy-3′,5′-dimethoxyflavanone(7), batatasin-III(8), 3,3′,5-trihydroxybibenzyl(9), trigonopol B(10), syringaresinol(11), 2,4,7-trihydroxyl-9,10-dihydrophenanthrene(12), loddigesiinol B(13), loddigesiinol I(14), loddigesiinol J(15),respectively. Compounds 1-11 among them were isolated from D. loddigesii for the first time. The biological activities of compounds 1-4, 6, 7 and 12 were evaluated for the first time under trial conditions. It was reported for the first time that compounds 1, 3 and 12 had a strong antioxidant activity, compounds 1 and 9 showed a strong α-glucosidase inhibitory activity, and compounds 1, 12, 14 and 15 had a strong anti-inflammatory activity.
To study the polyphenols from Dendrobium loddigesii and their biological activities, the 80% acetone extract from D. loddigesii was isolated and purified by chromatography techniques; the structures of obtained compounds were identified with spectroscopic techniques; the antioxidative, α-glucosidase inhibitory and anti-inflammatory activities of compounds were evaluated. Fifteen compounds were isolated and identified as chrysotoxol A(1), neoechinulin A(2), 3,6,9-trihydroxy-3,4-dihydroanthracen-1(2 H)-one(3), 4,4′-dihydroxyl-3,5-dimethoxylbibenzyl(4), naringenin(5), 5,4′-dihydroxy-7,3′,5′-trimethoxyflavanone(6), 5,7,4′-trihydroxy-3′,5′-dimethoxyflavanone(7), batatasin-III(8), 3,3′,5-trihydroxybibenzyl(9), trigonopol B(10), syringaresinol(11), 2,4,7-trihydroxyl-9,10-dihydrophenanthrene(12), loddigesiinol B(13), loddigesiinol I(14), loddigesiinol J(15),respectively. Compounds 1-11 among them were isolated from D. loddigesii for the first time. The biological activities of compounds 1-4, 6, 7 and 12 were evaluated for the first time under trial conditions. It was reported for the first time that compounds 1, 3 and 12 had a strong antioxidant activity, compounds 1 and 9 showed a strong α-glucosidase inhibitory activity, and compounds 1, 12, 14 and 15 had a strong anti-inflammatory activity.
引文
[1] 陶沙,吴锦丹,朱剑.2型糖尿病的抗炎治疗[J].国际内分泌代谢杂志,2012,32(3):169-172.TAO S,WU J D,ZHU J.Anti-inflammatory treatment for type 2 diabetes mellitus[J].International Journal of Endocrinology and Metabolism,2012,32(3):169-172.
[2] 朱玲,赵晋华,李祖长.糖尿病低度炎症机制的中医实验及临床研究进展[J].医学综述,2012,18(13):2090-2092.ZHU L,ZHAO J H,LI Z C.Traditional Chinese medicine experimental and clinical research progress of diabetes mellitus low-grade inflammation mechanism[J].Medical Recapitulate,2012,18(13):2090-2092.
[3] 常洁,姜宗培,余学清.氧化应激及其在糖尿病肾病中的作用[J].国际内科学杂志,2007,34(2):105-108.CHANG J,JIANG Z P,YU X Q.Oxidative stress and its role in diabetic nephropathy[J].International Journal of Internal Medicine,2007,34(2):105-108.
[4] 张慧娟,刘晓民.氧化应激与糖尿病[J].生物磁学,2006,6(1):72-74.ZHANG H J,LIU X M.Oxidative stress and diabetes[J].Biomagnetism,2006,6(1):72 74.
[5] 张捷平,郑晓玲,洪佳祝,等.复方石斛合剂治疗II型糖尿病90例[J].福建中医药大学学报,2011,21(5):6-10.ZHANG J P,ZHENG X L,HONG J Z,et al.Dendrobium compound in treating 90 case of type 2 diabetes memtus[J].Journal of Fujian College of Traditional Chinese Medicine,2011,21(5):6-10.
[6] 张捷平,施红.石斛合剂及其各组分对α-葡萄糖苷酶的抑制作用[J].福建中医学院学报,2004,14(5):37-38.ZHANG J P,SHI H.The depressant effect of Dendrobium mixture and its components on α-glucosidase[J].Journal of Fujian College of Traditional Chinese Medicine,2004,14(5):37-38.
[7] GONG C Y,YU Z Y,LU B,et al.Ethanol extract of Dendrobium chrysotoxum Lindl ameliorates diabetic retinopathy and its mechanism[J].Vascular Pharmacology,2014,62:134-142.
[8] LU Y,KUANG M,HU G P,et al.Loddigesiinols G-J:α-glucosidase inhibitors from Dendrobium loddigesii[J].Molecules,2014,19:8544-8555.
[9] HU J M,FAN W W,DONG F W,et al.Chemical components of Dendrobium chrysotoxum[J].Chinese Journal of Chemistry,2012,30(6):1327-1330.
[10] YAN X L,ZHOU Y F,TANG J J,et al.Diketopiperazine indole alkaloids from hemp seed[J].Phytochemistry Letters,2016,18:77-82.
[11] HU J M,ZHAO Y X,MIAO Z H,et al.Chemical components of Dendrobium polyanthum[J].Bulletin of the Korean Chemical Society,2009,30(9):2098-2100.
[12] 周佳,周先丽,梁成钦,等.铁皮石斛化学成分研究[J].中草药,2015,46(9):1292-1295.ZHOU J,ZHOU X L,LIANG C Q,et al.Chemical constituents of Dendrobium officinale[J].Chinese Traditional and Herbal Drugs,2015,46(9):1292-1295.
[13] MAJEKODUNMI O F,SUAD K S A B,JOHN O O,et al.Muscanone:a 3-O-(1″,8″,14″-trimethylhexadecanyl)naringenin from Commiphora wightii[J].Phytochemistry,2003,62(8):1251-1255.
[14] 张兴,梅文莉,曾艳波,等.槟榔果实的酚类化学成分与抗菌活性的初步研究[J].热带亚热带植物学报,2009,17(1):74-76.ZHANG X,MEI W L,ZENG Y B,et al.Phenolic constituents from the fruits of Areca catechu and their anti-bacterial activities[J].Journal of Tropical and Subtropical Botany,2009,17(1):74-76.
[15] 师彦平,李瑜.铁杆蒿化学成分研究[J].高等学校化学学报,1992,13(10):1258-1261.SHI Y P,LI Y.Chemical constituents of Artemisia subdigitata Mattf[J].Chemical Journal of Chinese Universities,1992,13(10):1258-1261.
[16] MAJUMDER P L,GUHA S,SEN S.Bibenzyl derivatives from the orchid Dendrobium amoenum[J].Phytochemistry,1999,52:1365-1369.
[17] 郭晓宇,王珏,王乃利,等.云南石仙桃的化学成分及其抑制NO生成的作用[J].中草药,2006,37(4):492-496.GUO X Y,WANG J,WANG N L,et al.Constituents from Pholidota yunnanensis and their inhibitory effects on nitric oxide production[J].Chinese Traditional and Herbal Drugs,2006,37(4):492-496.
[18] HUA J M,CHEN J J,YU H,et al.Two novel bibenzyls from Dendrobium trigonopus[J].Journal of Asian Natural Products Research,2008,10:647-651.
[19] 丁林芬,王海垠,王扣,等.香果树化学成分的研究[J].中成药,2016,38(12):2610-2614.DING L F,WANG H Y,WANG K,et al.Chemical constituents from Emmenopterys henryi[J].Chinese Traditional Patent Medicine,2016,38(12):2610-2614.
[20] 李春燕,陆羽,陈烨,等.环草石斛化学成分研究[J].中山大学学报(自然科学版),2013,52(3):73-76.LI C Y,LU Y,CHEN Y,et al.Chemical components of Dendrobium loddigesii[J].Acta Scientiarum Naturalium Universitatis Sunyatseni,2013,52(3):73-76.
[21] ITO M,MATSUZAKI K,Wang J,et al.New phenanthrenes and stilbenes from Dendrobium loddigesii[J].Chemical & Pharmaceutical Bulletin,2010,58:628-633.
[22] SHIMADA K,FUJIKAWA K,YAHARA K,et al.Antioxidative properties of xanthin on autoxidation of soybean oil in cyclodextrin emulsion[J].Journal of Agricultural and Food Chemistry,1992,40:945-948.
[23] 李海斌,蓝雄,刘婷,等.阳江红树林内生真菌Aspergillus sp.5Y次级代谢产物及其活性的研究[J].中山大学学报(自然科学版),2017,56(3):100-104.LI H B,LAN X,LIU T,et al.The secondary metabolites and bioactivities of mangrove endophytic fungus Aspergillus sp.5Y in Yangjiang[J].Acta Scientiarum Naturalium Universitatis Sunyatseni,2017,56(3):100-104.
[24] KHLIFI D,SGHAIER R M,LAOUNI D,et al.Anti-inflammatory and acetylcholinesterase inhibition activities of Globularia alypum[J].Journal of Medical and Bioengineering,2013,2:232-237.
[2] 朱玲,赵晋华,李祖长.糖尿病低度炎症机制的中医实验及临床研究进展[J].医学综述,2012,18(13):2090-2092.ZHU L,ZHAO J H,LI Z C.Traditional Chinese medicine experimental and clinical research progress of diabetes mellitus low-grade inflammation mechanism[J].Medical Recapitulate,2012,18(13):2090-2092.
[3] 常洁,姜宗培,余学清.氧化应激及其在糖尿病肾病中的作用[J].国际内科学杂志,2007,34(2):105-108.CHANG J,JIANG Z P,YU X Q.Oxidative stress and its role in diabetic nephropathy[J].International Journal of Internal Medicine,2007,34(2):105-108.
[4] 张慧娟,刘晓民.氧化应激与糖尿病[J].生物磁学,2006,6(1):72-74.ZHANG H J,LIU X M.Oxidative stress and diabetes[J].Biomagnetism,2006,6(1):72 74.
[5] 张捷平,郑晓玲,洪佳祝,等.复方石斛合剂治疗II型糖尿病90例[J].福建中医药大学学报,2011,21(5):6-10.ZHANG J P,ZHENG X L,HONG J Z,et al.Dendrobium compound in treating 90 case of type 2 diabetes memtus[J].Journal of Fujian College of Traditional Chinese Medicine,2011,21(5):6-10.
[6] 张捷平,施红.石斛合剂及其各组分对α-葡萄糖苷酶的抑制作用[J].福建中医学院学报,2004,14(5):37-38.ZHANG J P,SHI H.The depressant effect of Dendrobium mixture and its components on α-glucosidase[J].Journal of Fujian College of Traditional Chinese Medicine,2004,14(5):37-38.
[7] GONG C Y,YU Z Y,LU B,et al.Ethanol extract of Dendrobium chrysotoxum Lindl ameliorates diabetic retinopathy and its mechanism[J].Vascular Pharmacology,2014,62:134-142.
[8] LU Y,KUANG M,HU G P,et al.Loddigesiinols G-J:α-glucosidase inhibitors from Dendrobium loddigesii[J].Molecules,2014,19:8544-8555.
[9] HU J M,FAN W W,DONG F W,et al.Chemical components of Dendrobium chrysotoxum[J].Chinese Journal of Chemistry,2012,30(6):1327-1330.
[10] YAN X L,ZHOU Y F,TANG J J,et al.Diketopiperazine indole alkaloids from hemp seed[J].Phytochemistry Letters,2016,18:77-82.
[11] HU J M,ZHAO Y X,MIAO Z H,et al.Chemical components of Dendrobium polyanthum[J].Bulletin of the Korean Chemical Society,2009,30(9):2098-2100.
[12] 周佳,周先丽,梁成钦,等.铁皮石斛化学成分研究[J].中草药,2015,46(9):1292-1295.ZHOU J,ZHOU X L,LIANG C Q,et al.Chemical constituents of Dendrobium officinale[J].Chinese Traditional and Herbal Drugs,2015,46(9):1292-1295.
[13] MAJEKODUNMI O F,SUAD K S A B,JOHN O O,et al.Muscanone:a 3-O-(1″,8″,14″-trimethylhexadecanyl)naringenin from Commiphora wightii[J].Phytochemistry,2003,62(8):1251-1255.
[14] 张兴,梅文莉,曾艳波,等.槟榔果实的酚类化学成分与抗菌活性的初步研究[J].热带亚热带植物学报,2009,17(1):74-76.ZHANG X,MEI W L,ZENG Y B,et al.Phenolic constituents from the fruits of Areca catechu and their anti-bacterial activities[J].Journal of Tropical and Subtropical Botany,2009,17(1):74-76.
[15] 师彦平,李瑜.铁杆蒿化学成分研究[J].高等学校化学学报,1992,13(10):1258-1261.SHI Y P,LI Y.Chemical constituents of Artemisia subdigitata Mattf[J].Chemical Journal of Chinese Universities,1992,13(10):1258-1261.
[16] MAJUMDER P L,GUHA S,SEN S.Bibenzyl derivatives from the orchid Dendrobium amoenum[J].Phytochemistry,1999,52:1365-1369.
[17] 郭晓宇,王珏,王乃利,等.云南石仙桃的化学成分及其抑制NO生成的作用[J].中草药,2006,37(4):492-496.GUO X Y,WANG J,WANG N L,et al.Constituents from Pholidota yunnanensis and their inhibitory effects on nitric oxide production[J].Chinese Traditional and Herbal Drugs,2006,37(4):492-496.
[18] HUA J M,CHEN J J,YU H,et al.Two novel bibenzyls from Dendrobium trigonopus[J].Journal of Asian Natural Products Research,2008,10:647-651.
[19] 丁林芬,王海垠,王扣,等.香果树化学成分的研究[J].中成药,2016,38(12):2610-2614.DING L F,WANG H Y,WANG K,et al.Chemical constituents from Emmenopterys henryi[J].Chinese Traditional Patent Medicine,2016,38(12):2610-2614.
[20] 李春燕,陆羽,陈烨,等.环草石斛化学成分研究[J].中山大学学报(自然科学版),2013,52(3):73-76.LI C Y,LU Y,CHEN Y,et al.Chemical components of Dendrobium loddigesii[J].Acta Scientiarum Naturalium Universitatis Sunyatseni,2013,52(3):73-76.
[21] ITO M,MATSUZAKI K,Wang J,et al.New phenanthrenes and stilbenes from Dendrobium loddigesii[J].Chemical & Pharmaceutical Bulletin,2010,58:628-633.
[22] SHIMADA K,FUJIKAWA K,YAHARA K,et al.Antioxidative properties of xanthin on autoxidation of soybean oil in cyclodextrin emulsion[J].Journal of Agricultural and Food Chemistry,1992,40:945-948.
[23] 李海斌,蓝雄,刘婷,等.阳江红树林内生真菌Aspergillus sp.5Y次级代谢产物及其活性的研究[J].中山大学学报(自然科学版),2017,56(3):100-104.LI H B,LAN X,LIU T,et al.The secondary metabolites and bioactivities of mangrove endophytic fungus Aspergillus sp.5Y in Yangjiang[J].Acta Scientiarum Naturalium Universitatis Sunyatseni,2017,56(3):100-104.
[24] KHLIFI D,SGHAIER R M,LAOUNI D,et al.Anti-inflammatory and acetylcholinesterase inhibition activities of Globularia alypum[J].Journal of Medical and Bioengineering,2013,2:232-237.