腾冲重楼根茎的化学成分及抗菌活性研究

Studies on chemical constituents and antimicrobial activities of rhizomes of Paris tengchongensis

目的研究藜芦科植物腾冲重楼Paris tengchongensis根茎的化学成分及抗菌活性。方法采用HPD100大孔吸附树脂、正相硅胶、RPC_(18)硅胶和Sephadex LH-20凝胶色谱,以及半制备高效液相色谱等方法进行分离和纯化,利用NMR和MS等波谱数据对化合物的化学结构进行鉴定。对分离到的化合物用微量稀释法进行抗细菌和真菌活性评价。结果从腾冲重楼根茎70%乙醇提取物中分离并鉴定了16个化合物,分别为parisvanioside A(1)、kingianoside K(2)、7-氧薯蓣皂苷(3)、pariposide A(4)、parisvanioside B(5)、parisrugoside H(6)、(25R)-17α-羟基螺甾-5-烯-3β-基O-β-D-吡喃葡萄糖基-(1→4)-O-[α-L-吡喃鼠李糖基-(1→2)]-β-D-吡喃葡萄糖苷(7)、麦冬皂苷Cʹ(8)、纤细薯蓣皂苷(9)、重楼皂苷Ⅰ(10)、重楼皂苷Ⅱ(11)、重楼皂苷Ⅵ(12)、pennogenin 3-O-β-chacotrioside(13)、重楼皂苷H(14)、重楼皂苷Ⅶ(15)和β-蜕皮激素(16)。化合物3、5~15对絮状表皮癣菌有较强抑制作用,50%最低抑菌浓度(50%minimun inhibitory concentration,MIC50)为0.07~93.60μmol/L;化合物5~15对红色毛癣菌有较强抑制作用,MIC50为0.06~73.08μmol/L;化合物3、5~8、10~15对石膏样小孢子菌有很强的抑制作用,MIC50为0.04~69.92μmol/L。结论化合物1~7为首次从腾冲重楼中分离得到;化合物7、12~15对白色念珠菌氟康唑耐药株抑制率可达100%。化合物11对絮状表皮癣菌抑菌效果最好,MIC50为(0.07±0.004)μmol/L;化合物11对红色毛癣菌抑菌效果最好,MIC50为(0.06±0.003)μmol/L;化合物11对石膏样小孢子菌抑菌效果最好,MIC50为(0.04±0.001)μmol/L。腾冲重楼中含有的甾体皂苷有治疗皮肤及深部真菌感染的潜力。

Objective To investigate the chemical constituents from the rhizomes of Paris tengchongensis Y.H.Ji,C.J.Yang&Y.L.Huan(Melanthiaceae)and their antibacterial and antifungal activities.Methods The separations and purifications were taken by HPD100 macroporous resin,normal phase silica gel,reversed-phase(RP)C_(18) silica gel,Sephadex LH-20 gel chromatography,and semi-preparative high-performance liquid chromatography(HPLC).The chemical structures of the isolated compounds were determined by combining spectroscopic data of nuclear magnetic resonance(NMR),mass spectrum(MS),etc.These isolates were tested for antibacterial and antifungal activities by microdilution method.Results A total of 16 compounds were isolated and identified from 70%ethanol extract of the rhizomes of P.tengchongensis,which were identified to be parisvanioside A(1),kingianoside K(2),7-oxodioscin(3),pariposide A(4),parisvanioside B(5),parisrugoside H(6),(25R)-17α-hydroxyspirost-5-en-3β-yl O-β-Dglucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside(7),ophiopogonin Cʹ(8),gracillin(9),paris saponinⅠ(10),paris saponin II(11),paris saponinⅥ(12),pennogenin 3-O-β-chacotrioside(13),paris saponin H(14),paris saponinⅦ(15),andβ-ecdysterone(16).Compound 3 and 5—15 exhibited strong inhibitory effects against Epidermophyton floccosum,with MIC50(50%minimun inhibitory concentration)values ranging from 0.07 to 93.60μmol/L;Compound 5—15 exhibited strong inhibitory effects against Trichophyton rubrum,with MIC50 values ranging from 0.06 to 73.08μmol/L;Compounds 3,5—8 and 10—15 exhibited very strong inhibitory effects against Microsporum gypseum,with MIC50 values ranging from 0.04 to 69.92μmol/L.Conclusion Compounds 1—7 are isolated from P.tengchongensis for the first time.Compounds 7,and 12—15 can inhibit 100%the fluconazoleresistant strain of Candida albicans.Compound 11 has the best antifungal effect on Epidermophyton floccosum,MIC50=(0.07±0.004)μmol/L.Compound 11 has the best antifungal effect on Trichophyton rubrum,MIC50=(0.06±0.003)μmol/L.Compound 11 has the best antifungal effect on Microsporum gypseum,MIC50=(0.04±0.001)μmol/L.The steroidal saponins in this plant have the potential to treat skin and invasive fungal infections.