美花石斛化学成分及其护肤活性研究
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摘要
本文研究美花石斛(Dendrobium loddigesii)的化学成分及其护肤活性。采用色谱法从美花石斛粗提物中分离得到12个化合物,利用波谱学方法分别鉴定为拖鞋状石斛素(1)、2,4,7-三羟基-9,10-二氢菲(2)、3,6,9-三羟基-3,4-二氢蒽-1(2H)-酮(3)、3,5′-二甲氧基-3′,4,9′-三羟基-7′,9-环氧-8,8′-木酚素(4)、5-(4-羟基-3-甲氧基苯乙基)-2-(4-羟基-3-甲氧基苯基)苯并二氢呋喃-3,7-二醇(5)、5-(4′′-羟基-3′′-甲氧基苯乙基)-2-(4′-羟基-5′-甲氧基苯基)-7-甲氧基苯并二氢吡喃-3-醇(6)、丁香脂素(7)、异香草醛(8)、松柏醛(9)、2-甲氧基-5-羟甲基苯酚(10)、二氢松柏醇(11)、4-羟基-3-甲氧基苯乙醇(12)。其中化合物3～5、7～12为首次从美花石斛中分离得到;化合物1、2、6(100μg/mL)有一定的自由基清除活性(>80%);化合物2(10μg/mL)有一定促胶原蛋白分泌活性(>20%)。结果显示从美花石斛的茎中分离得到了12个化合物,3个表现出良好的护肤活性。
To study the chemical constituents and explore the skin caring activity of Dendrobium loddigesii,all compounds were isolated by chromatography with silica gel,Sephadex LH-20,MCI gel and Lichroprep RP-18 gel and identified by NMR and MS;Twelve compounds were isolated from D.loddigesii,which were moscatin(1),2,4,7-trihydroxyl-9.10-dihydrophenanthrene(2),3,6,9-trihydroxy-3,4-dihydroanthracen-1(2 H)-one(3),3,5′-dimethoxy-3′,4,9′-trihydroxy-7′,9-epoxy-8,8′-lignan(4),trigonopol B(5),crepidatuol B(6),syringaresinol(7),isovanillin(8),coniferyl aldehyde(9),2-methoxyphenol-5-hydroxymethyl(10),dihydroconiferyl alcohol(11),4-hydroxy-3-methoxyphenylethanol(12).And compound 3-5,7-12 were isolated from this plant for the first time.Compound 1,2,6 could scavenge almost 80% DPPH radical at 100 μg/mL,compound 2 could promote 25.6% secretion of collagen at 10 μg/mL.
To study the chemical constituents and explore the skin caring activity of Dendrobium loddigesii,all compounds were isolated by chromatography with silica gel,Sephadex LH-20,MCI gel and Lichroprep RP-18 gel and identified by NMR and MS;Twelve compounds were isolated from D.loddigesii,which were moscatin(1),2,4,7-trihydroxyl-9.10-dihydrophenanthrene(2),3,6,9-trihydroxy-3,4-dihydroanthracen-1(2 H)-one(3),3,5′-dimethoxy-3′,4,9′-trihydroxy-7′,9-epoxy-8,8′-lignan(4),trigonopol B(5),crepidatuol B(6),syringaresinol(7),isovanillin(8),coniferyl aldehyde(9),2-methoxyphenol-5-hydroxymethyl(10),dihydroconiferyl alcohol(11),4-hydroxy-3-methoxyphenylethanol(12).And compound 3-5,7-12 were isolated from this plant for the first time.Compound 1,2,6 could scavenge almost 80% DPPH radical at 100 μg/mL,compound 2 could promote 25.6% secretion of collagen at 10 μg/mL.
引文
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2 Itom,Matsuzaki K,Wang J,et al.New phenanthrenes and stilbenes from Dendrobium loddigesii[J].Chem Pharm Bull,2010,58:628-633.
3 Lu Y,Kuang M,Hu GP,et al.Loddigesiinols G-J:alpha-glucosidase inhibitors from Dendrobium loddigesii[J].Molecules,2014,19:8544-8555.
4 Chen HP,Li XW,Xu YL,et al.Study on the polar extracts of Dendrobium nobile,D.officinale,D.loddigesii,and Flickingeria fimbriata:metabolite identification,content evaluation,and bioactivity assay[J].Molecules,2018,23:1185-1195.
5 Geng XY,Li ZS.Sterile seeding and breeding technology of dendrobium seed[J].Chin Trop Agric(中国热带农业),2012,4:36-36.
6 Zhu H,Zhang M,Li L,et al.Extraction process optimization and content determination of dendrobium polysaccharide[J].Asia-Pacific Trad Med(亚太传统医药),2017,13(2):21-23.
7 Li XW,Chen HP,He YY,et al.Effects of rich-polyphenols extract of Dendrobium loddigesii on anti-diabetic,anti-inflammatory,anti-oxidant,and gut microbiota modulation in db/db mice[J].Molecules,2018,23:3245-3265.
8 Chen YP,Liang CH,Wu HT,et al.Antioxidant and anti-inflammatory capacities of collagen peptides from milkfish(Chanos chanos) scales[J].J Food Sci Technol,2018,55:2310–2317.
9 Elizabeth GJ,Anita R,Stephen B,et al.Development of an in silico model of DPPH free radical scavenging capacity:prediction of antioxidant activity of coumarin type compounds[J].Int J Mol Sci,2016,17:881-891.
10 Li C,Lu Y,Chen Y,et al.Chemical components of Dendrobium loddigesii[J].Acta Sci Natur Univ Sunyatseni,2013,52:73-76.
11 Hu JM,Zhao YX,Miao ZH,et al.Chemical components of dendrobium polyanthum[J].Bull Korean Chem Soc,2009,30:2098-2100.
12 Wang WS,Lan XC,Wu HB,et al.Lignans from the flower buds of Magnolia liliflora Desr[J].Planta Med,2012,78:141-147.
13 Hu JM,Chen JJ,Yu H,et al.Two novel bibenzyls from Dendrobium trigonopus[J].J Asian Nat Prod Res,2008,10:647-651.
14 Li CB,Wang C,Fan WW,et al.Chemical components of Dendrobium crepidatum and their neurite outgrowth enhancing activities[J].Nat Prod Bioprosp,2013,3:70-73.
15 Chang FR,Chao YC,Teng CM,et al.Chemical constituents from Cassytha filiformis II[J].J Nat Prod,1998,61:863-863.
16 Bao K,Fan A,Dai Y,et al.Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products[J].Org Biomol Chem,2009,7:5084-5090.
17 Shao TM,Song XP,Chen GY,et al.Chemical constituents from stems of Ficus auriculata[J].Chin Tradit Herb Drugs,2013,44:2208-2212.
18 Lai A,Monduzzi M,Saba G.Carbon‐13 NMR studies on catechol,phenol and benzene derivatives of biological relevance[J].Magn Reson Chem,2011,23:379-383.
19 Sun ZC,Zheng QX,Wu HF,et al.Study on water soluble chemical constituents of Whisker Grass[J].Chin Pharm J(中国药学杂志),2014,49:22-25.
20 Feng WS,Su FY,Zheng XK,et al.Chemical constituents of north China columbine[J].Chin Pharm J(中国药学杂志),2011,46:496-499.
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