珍贵束丝放线菌产生的新代谢产物1-羟基-4-O-鼠李糖-2-萘甲酸甲酯
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摘要
目的发现珍贵束丝放线菌ATCC31565产生的新代谢产物。方法 TLC和LC-MS等分析珍贵束丝放线菌ATCC31565培养物的乙酸乙酯提取物,发现目标化合物。采用MCI色谱柱和半制备HPLC等分离纯化目标化合物。对目标化合物的NMR等数据进行分析,确定其化学结构。结果从珍贵束丝放线菌ATCC31565中发现了一个化学结构为1-羟基-4-O-鼠李糖-2-萘甲酸甲酯的新化合物,并将其命名为珍贵酚。结论推测珍贵酚是1,4-二羟基-2-萘甲酸(甲萘醌的生物合成前体物)和L-鼠李糖这两个初级代谢产物的脱水缩合产物再经过甲酯化形成的。
Objective To discover novel metabolite(s) from Actinosynnema pretiosum ATCC 31565.Methods TLC and LC-MS were used to analyze the EtOAc extract of fermentation culture of ATCC 31565. MCI column chromatography and HPLC were employed for the isolation of novel metabolite. The structure of the metabolite was elucidated by NMR.Results A new metabolite, designated as pretiphenol, was discovered from Actinosynnema pretiosum ATCC 31565. The structure of pretiphenol was determined as methyl 1-hydroxy-4-O-rhamnosyl-2-naphthoate.Conclusion Pretiphenol might be the dehydration product of 1,4-dihydroxy-2-naphthoate(an intermediate in menaquinone biosynthesis) and L-rhamnose, followed by esterification with methanol.
Objective To discover novel metabolite(s) from Actinosynnema pretiosum ATCC 31565.Methods TLC and LC-MS were used to analyze the EtOAc extract of fermentation culture of ATCC 31565. MCI column chromatography and HPLC were employed for the isolation of novel metabolite. The structure of the metabolite was elucidated by NMR.Results A new metabolite, designated as pretiphenol, was discovered from Actinosynnema pretiosum ATCC 31565. The structure of pretiphenol was determined as methyl 1-hydroxy-4-O-rhamnosyl-2-naphthoate.Conclusion Pretiphenol might be the dehydration product of 1,4-dihydroxy-2-naphthoate(an intermediate in menaquinone biosynthesis) and L-rhamnose, followed by esterification with methanol.
引文
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[11]Matsubara M,Yamachika E,Tsujigiwa H,et al.Suppressive effects of1,4-dihydroxy-2-naphthoic acid administration on bone resorption.Osteoporos Int,2010,21(8):1437-1447.
[12]Chen JC.A new synthetic method for 1,4-dihydroxy-2-naphthoic acid.Fine Chem,1996,5(16):47-49.(in Chinese)陈建村.新法合成1,4-二羟基-2-萘甲酸.精细化工,1996,5(16):47-49.
[13]Zhang JY,Jin H,Wang GF,et al.Methyl-1-hydroxy-2-naphthoate,a novel naphthol derivative,inhibits lipopolysaccharide-induced inflammatory response in macrophages via suppression of NF-κB,JNK and p38 MAPK pathways.Inflamm Res,2011,60(9):851-859.
[2]Tanida S,Izawa M,Hasegawa T,et al.Ansamitocin analogs from a mutant strain of Nocardia.I.Isolation of the mutant,fermentation and antimicrobial properties.J Antibiot(Tokyo),1981,34(5):489-495.
[3]Lu C,Xie F,Shan C,et al.Two novel cyclic hexapeptides from the genetically engineered Actinosynnema pretiosum.Appl Microbiol Biotechnol,2017,101(6):2273-2279.
[4]Lu C,Bai L,Shen Y.Five unusual natural carbohydrates from Actinosynnema pretiosum.Chem Nat Comp,2017,44(5):594-597.
[5]Yan J,Guo XQ,Li XG,et al.TLC to fleetly analyze monosaccharide composition of polysaccharide.Food Sci,2006,27(12):603-607.(in Chinese)颜军,郭晓强,李晓光,等.TLC快速分析多糖的单糖组成.食品科学,2006,27(12):603-607.
[6]Zhao PP,Li BM,He LY.Studies on the method of determination of combined sugars in glycosides.Acta Pharmaceutica Sinica,1987,22(1):70-74.(in Chinese)赵萍萍,李宝明,何丽一.甙中结合糖测定方法的研究.药学学报,1987,22(1):70-74.
[7]Livingston MJ,Ding HF,Huang S,et al.Persistent activation of autophagy in kidney tubular cells promotes renal interstitial fibrosis during unilateral ureteral obstruction.Autophagy,2016,12(6):976-998.
[8]Ma J,Zhao PJ,Shen YM.A novel vanillic amide rhamnoside from actinosynnema pretiosum.Nat Product Res Dev,2006,18(5):721-722.(in Chinese)马娟,赵沛基,沈月毛.珍贵橙色束丝放线菌中新颖香草酰氨鼠李糖糖苷化合物.天然产物研究与开发,2006,18(5):721-722.
[9]Fan JT,Kuang B,Zeng GZ,et al.Biologically active arborinane-type triterpenoids and anthraquinones from Rubia yunnanensis.J Nat Prod,2011,74(10):2069-2080.
[10]Zhou Y,Yang B,Jiang Y,et al.Studies on cytotoxic activity against HepG-2 cells of naphthoquinones from green walnut husks of Juglans mandshurica maxim.Molecules,2015,20(9):15572-15588.
[11]Matsubara M,Yamachika E,Tsujigiwa H,et al.Suppressive effects of1,4-dihydroxy-2-naphthoic acid administration on bone resorption.Osteoporos Int,2010,21(8):1437-1447.
[12]Chen JC.A new synthetic method for 1,4-dihydroxy-2-naphthoic acid.Fine Chem,1996,5(16):47-49.(in Chinese)陈建村.新法合成1,4-二羟基-2-萘甲酸.精细化工,1996,5(16):47-49.
[13]Zhang JY,Jin H,Wang GF,et al.Methyl-1-hydroxy-2-naphthoate,a novel naphthol derivative,inhibits lipopolysaccharide-induced inflammatory response in macrophages via suppression of NF-κB,JNK and p38 MAPK pathways.Inflamm Res,2011,60(9):851-859.