杜英内生真菌Aspergillus versicolor倍半萜类次级代谢产物及(8S)-hydroxysydonic acid的含量测定研究
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摘要
从植物杜英的叶片中分离得到一株内生真菌,经分子生物学方法鉴定为Aspergillus versicolor,在实验室中以大米麸皮培养基固体培养,40 d后经乙酸乙酯萃取,浓缩得浸膏,经正相硅胶柱,Sephadex LH-20及半制备高效液相色谱分离得到8个次级代谢产物,经核磁共振,质谱等光谱学方法鉴定其结构,分别为(-)-hydroxysydonic acid(1),12-acetoxysydonic acid (2),10-hydroxysydowic acid (3), sydowic acid(4),sydonic acid(5),(S)-(+)-11-dehydrosydonic acid (6),sydonol 1b (7),(R)-hydroxyboivinianic acid (8).化合物1-8中,化合物1的量最大,通过HPLC测定了(-)-hydroxysydonic acid(1)的含量,在固体培养条件下其含量达11.4%.为进一步的开发没药烷类倍半萜类化合物的应用提供了物质保障.
An endophytic fungus was isolated from the leaf of Elaeocarpus decipiens Hemsl., and identified as Aspergillus versicolor, then fermented on the rice solid medium. After 40 days, the solid medium was extracted by ester acetate, and the crude was subjected to silicon gel column, Sephadex LH-20 and semi-HPLC chromatography and nine secondary metabolites were obtained, and their structures were identified as(-)-hydroxysydonic acid(1),12-acetoxysydonic acid(2),10-hydroxysydowic acid(3), sydowic acid(4),sydonic acid(5),(S)-(+)-11-dehydrosydonic acid(6),sydonol 1 b(7),(R)-hydroxyboivinianic acid(8) by NMR and MS spectra. Finally, the content of compound 1 was tested by HPLC chromatography, the content of compound 1 was 11.4% under the solid medium cultural condition.
An endophytic fungus was isolated from the leaf of Elaeocarpus decipiens Hemsl., and identified as Aspergillus versicolor, then fermented on the rice solid medium. After 40 days, the solid medium was extracted by ester acetate, and the crude was subjected to silicon gel column, Sephadex LH-20 and semi-HPLC chromatography and nine secondary metabolites were obtained, and their structures were identified as(-)-hydroxysydonic acid(1),12-acetoxysydonic acid(2),10-hydroxysydowic acid(3), sydowic acid(4),sydonic acid(5),(S)-(+)-11-dehydrosydonic acid(6),sydonol 1 b(7),(R)-hydroxyboivinianic acid(8) by NMR and MS spectra. Finally, the content of compound 1 was tested by HPLC chromatography, the content of compound 1 was 11.4% under the solid medium cultural condition.
引文
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[2] Hugenholtz J.Population dynamics of mixed starter cultures[J].Neth.Milk Dairy J.,1986,40:129-140.
[3] Boucher D H,James S,Keeler K H.The ecology of mutualism[J].Ann.Rev.Ecol.Syst.,1982,13:315-347.
[4] 李强,刘军,周东坡,等.植物内生菌的开发与研究进展[J].生物技术通报,2006,25(3):33-37.
[5] Hamasaki T,Nagayama K Z,Hatsuda Y C.Two new metabolites,sydonic acid and hydroxysydonic acid,from Aspergillus sydowi[J].Agricultural and Biological Chemistry,1978,42(1):37-40.
[6] Lu Z,Zhu H,Fu P,et al.Cytotoxic polyphenols from the marine-derived fungus Penicillium expansum[J].Journal of Natural Products,2010,73(5):911-914.
[7] Li X.B,Zhou Y H,Zhu R X,et al.Identification and biological evaluation of secondary metabolites from the endolichenic fungus Aspergillus versicolor[J].Chemistry & Biodiversity,2015,12(4):575-592.
[8] Bunbamrung N,Intaraudom C,Supothina S,et al.Antibacterial and anti-phytopathogenic substances from the insect pathogenic fungus Gibellula sp.BCC36964[J].Phytochemistry Letters,2015,3(11):142-147.
[9] Serra S,Cominetti A A.A divergent and stereoselective approach to phenolic 1,7-dihydroxy- bisabolane sesquiterpenes:asymmetric total synthesis of (+)-curcutetraol,(+)-sydonol,(+)-sydonic acid,and (+)-7-O-methylsydonic acid[J].Tetrahedron Asymmetry,2013,24(18):1110-1116.
[10] Elnaggar M S,Liu Z,Proksch P,et al.Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp.[J].Tetrahedron,2016,72(19):2411-2419.
[11] Wang J F,Lin X P,Qin C,et al.Antimicrobial and antiviral sesquiterpenoids from sponge-associated fungus,Aspergillus sydowii ZSDS1-F6[J].The Journal of Antibiotics,2014,67(8):581-583.
[12] Chung Y M,Wei C K,Chuang D W,et al.An epigenetic modifier enhances the production of anti-diabetic and anti-inflammatory sesquiterenoids from Aspergillus sydowii[J].Bioorganic & Medicinal Chemistry,2013,21(15):3866-3872.