茅苍术根茎中的2个新的多烯炔苷类化合物

Two new polyacetylene glycosides from rhizomes of Atractylodes lancea

目的对茅苍术Atractylodes lancea根茎的化学成分进行分离和鉴定,并评价所得化合物对脂多糖(LPS)诱导小胶质细胞BV2分泌NO的抑制作用。方法茅苍术根茎的80%乙醇提取物经萃取后,得正定醇亚部位;再依次经大孔吸附树脂柱、凝胶柱以及制备型高效液相色谱柱进行系统分离;采用HRESIMS、NMR、ECD等技术鉴定化合物的结构。结果从茅苍术根茎正丁醇亚部位中分离并鉴定了10个化合物,分别鉴定为(2E,8R)-癸烯-4,6-二炔-1,8-二醇-1-O-β-D-呋喃芹糖基-(1→6)-β-D-吡喃葡萄糖苷(1)、(8S)-癸烷-4,6-二炔-1,8-二醇-8-O-β-D-吡喃葡萄糖苷(2)、(2E,8R)-癸烯-4,6-二炔-1,8-二醇-8-O-β-D-吡喃葡萄糖苷(3)、(2E,8S)-癸烯-4,6-二炔-1,8-二醇-8-O-β-D-吡喃葡萄糖苷(4)、(2E,8E)-2,8-癸二烯-4,6-二炔-1,10-二醇-1-O-β-D-吡喃葡萄糖苷(5)、(7R,8S)-3',9,9'-三羟基-3-甲氧基-1'-丙醇基-7,8-苯并二氢呋喃木脂素-4-O-β-D-吡喃葡萄糖苷(6)、(7'R*,8S*,8'S*)-南烛木树脂酚9'-O-β-D-吡喃葡萄糖苷(7)、(7S,8R)-4,9,9'-三羟基-3'-甲氧基-8-O-4'-新木脂素7-O-β-D-吡喃葡萄糖苷(8)、水杨酸甲酯2-O-α-L-吡喃木糖基-(1→6)-β-D-吡喃葡萄糖苷(9)、苯乙醇7-O-α-L-吡喃鼠李糖基-(1→6)-β-D-吡喃葡萄糖苷(10)。结论化合物1和2为2个新的C10骨架类型的多烯炔苷,分别命名为苍术烯炔苷A和苍术烯炔苷B;化合物6、8~10为首次从从茅苍术中分离得到;在10μmol/L浓度下,化合物10对小胶质细胞分泌NO的抑制率最高,为31.18%;而1及2和4的混合物对小胶质细胞分泌NO的抑制率分别为22.01%和14.09%,仅具有较弱的体外抗炎活性。

Objective To investigate the chemical components from the 80%EtOH extract of Atractylodes lancea,as well as the inhibitory activities of the isolated compounds on LPS-induced NO production of microglia BV2 cells.Methods The n-BuOH-soluble fraction of the crude extract was successively chromatographed with Diaion HP-20,Sephadex LH-20,and preparative HPLC C18-column.At last,the planar and stereochemical structures of these obtained compounds were established on the basis of extensive spectroscopic data(HRESIMS,NMR,and ECD,etc).Results Ten glycosides were isolated from the n-BuOH-soluble fraction of the 80%EtOH extract of A.lancea,including(2E,8R)-decene-4,6-diyne-1,8-diol-1-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside(1),(8S)-decane-4,6-diyne-1,8-diol-8-O-β-D-glucopyranoside(2),(2E,8R)-decene-4,6-diyne-1,8-diol-8-O-β-D-glucopyranoside(3),(2E,8S)-decene-4,6-diyne-1,8-diol-8-O-β-D-glucopyranoside(4),(2E,8E)-2,8-decadiene-4,6-diyne-1,10-diol-1-O-β-D-glucopyranoside(5),(7R,8S)-3',9,9'-trihydroxyl-3-methoxyl-1'-propanol-7,8-dihydrobenzo-funanneoligan-4-O-β-D-glucopyranoside(6),(7'R*,8S*,8'S*)-lyoniresinol 9'-O-β-D-glucopyranoside(7),(7S,8R)-4,9,9'-trihydroxy-3'-methoxy-8-O-4'-neolignan 7-O-β-D-glucopyranoside(8),methyl salicylate 2-O-α-L-xylopyranosyl-(1→6)-β-D-glucopyranoside(9),and phenylmethanol 7-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside(10).Conclusion Compounds 1 and 2 are named atractyeneyneglycoside A and atractyeneyneglycoside B,while compounds 6,8-10 are first isolated from the rhizomes of A.lancea.At the concentration of 10μmol/L,compound 10 exhibited the strongest inhibitory effects on LPS-induced NO production of microglia BV2 cells with the value of 31.18%,while compounds 1 and 2 just showed weaker inhibitory effects with values of 22.01%and 14.09%,respectively.