深海链霉菌Streptomyces sp. PKU-MA01297中发现的两个葡萄糖苷化角环素

doi:10.5246/jcps.2019.12.079

中国药学(英文版) ›› 2019, Vol. 28 ›› Issue (12): 835-842.DOI: 10.5246/jcps.2019.12.079

深海链霉菌Streptomyces sp. PKU-MA01297中发现的两个葡萄糖苷化角环素

马学洋¹, 王贵阳¹, 张中义¹, 耿彤彤¹, 孙晓旭¹, 杨东辉¹, 汤熙祥^2*, 马明^1*

1. 北京大学医学部药学院天然药物及仿生药物国家重点实验室, 北京 100191
2. 自然资源部第三海洋研究所海洋生物遗传资源重点实验室, 福建厦门 361005

收稿日期:2019-06-24 修回日期:2019-08-19 出版日期:2019-12-28 发布日期:2019-12-25
通讯作者: E-mail: tangxixiang@tio.org.cn, Tel.: +86-592-2195365; E-mail: mma@bjmu.edu.cn, Tel.: +86-10-82805794
基金资助:
National Natural Science Foundation of China (Grant No. 81741148, 81573326, 81673332, 21877002), COMRA Project of China (Grant No. DY135-B2-08) and China Postdoctoral Science Foundation (Grant No. 2018M641123).

Two glucosylated angucyclines from deep-sea-derived Streptomyces sp. PKU-MA01297

Xueyang Ma¹, Guiyang Wang¹, Zhongyi Zhang¹, Tongtong Geng¹, Xiaoxu Sun¹, Donghui Yang¹, Xixiang Tang^2*, Ming Ma^1*

1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China
2. Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China

Received:2019-06-24 Revised:2019-08-19 Online:2019-12-28 Published:2019-12-25
Contact: E-mail: tangxixiang@tio.org.cn, Tel.: +86-592-2195365; E-mail: mma@bjmu.edu.cn, Tel.: +86-10-82805794
Supported by:
National Natural Science Foundation of China (Grant No. 81741148, 81573326, 81673332, 21877002), COMRA Project of China (Grant No. DY135-B2-08) and China Postdoctoral Science Foundation (Grant No. 2018M641123).

摘要/Abstract

摘要：

角环素类天然产物是由放线菌中发现的由II型聚酮合酶(PKS)产生的芳香聚酮化合物。它们的结构中不同位置的糖基团取代扩展了它们的结构多样性。本文报道了从一株深海链霉菌Streptomyces sp. PKU01297中发现的两个新的角环素类化合物(化合物1和2)。链霉菌Streptomyces sp. PKU01297分离自印度洋3202米深的海底沉积物。化合物1和2的结构通过综合分析NMR, MS和CD等实验数据得到解析,它们结构中的1-O-β-d-吡喃葡萄糖基团为首次在角环素类化合物中发现,丰富了深海天然产物的结构类型。针对化合物1和2开展了抗菌、抗肿瘤细胞毒和抗炎活性筛选,未发现两个化合物具有相关生物活性。本文的工作为将来开展化合物1和2的生物合成研究和更多的生物活性测试打下了基础。

关键词: 角环素, 深海链霉菌, 葡萄糖基团

Abstract:

Angucyclines are aromatic polyketides produced by type II polyketide synthase (PKS) exclusively from actinomycetes. These natural products contain hydrolyzable sugar moieties that attach to various positions of the polyketide skeleton and expand the structural diversity. We here report the isolation of two new angucyclines (1 and 2) from the deep-sea-derived Streptomycessp. PKU-MA01297, which was isolated from a sediment sample collected at a depth of 3202 meters from the Indian Ocean. The structures of the two new compounds were elucidated based on comprehensive methods, including NMR, MS and CD analysis. Compounds 1 and 2 featured a 1-O-β-d-glucopyranosyl moiety that has not been reported for angucyclines. Several biological activity assays, including antibacterial, cytotoxicity and anti-inflammatory assays, were carried out, and compounds 1 and 2 showed no activities. These results set the stage for biosynthetic research and more biological activity assays in the future.

Key words: Angucyclines, Deep-sea-derived Streptomyces, Glucopyranosyl moiety

中图分类号:

R284

Supporting:

马学洋, 王贵阳, 张中义, 耿彤彤, 孙晓旭, 杨东辉, 汤熙祥, 马明. 深海链霉菌Streptomyces sp. PKU-MA01297中发现的两个葡萄糖苷化角环素[J]. 中国药学(英文版), 2019, 28(12): 835-842.

Xueyang Ma, Guiyang Wang, Zhongyi Zhang, Tongtong Geng, Xiaoxu Sun, Donghui Yang, Xixiang Tang, Ming Ma. Two glucosylated angucyclines from deep-sea-derived Streptomyces sp. PKU-MA01297[J]. Journal of Chinese Pharmaceutical Sciences, 2019, 28(12): 835-842.

参考文献

[1] Kharel, M.K.; Pahari, P.; Shepherd, M.D.; Tibrewal, N.; Nybo, S.E.; Shaaban, K.A.; Rohr, J. Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis. Nat. Prod. Rep. 2012, 29, 264-325.

[2] Ma, M.; Rateb, M.E.; Teng, Q.H.; Yang, D.; Rudolf, J.D.; Zhu, X.C.; Huang, Y.; Zhao, L.X.; Jiang, Y.; Li, X.L.; Rader, C.; Duan, Y.W.; Shen, B. Angucyclines and angucyclinones from streptomyces sp. CB01913 featuring C-ring cleavage and expansion. J. Nat. Prod. 2015, 78, 2471-2480.

[3] Jin, J.; Yang, X.Y.; Liu, T.; Xiao, H.; Wang, G.Y.; Zhou, M.J.; Liu, F.W.; Zhang, Y.T.; Liu, D.; Chen, M.H.; Cheng, W.; Yang, D.H.; Ma, M. Fluostatins M-Q featuring a 6-5-6-6 ring skeleton and high oxidized A-rings from marine streptomyces sp. PKU-MA00045. Mar. Drugs. 2018, 16, E87.

[4] Carr, G.; Derbyshire, E.R.; Caldera, E.; Currie, C.R.; Clardy, J. Antibiotic and antimalarial quinones from fungus-growing ant-associated Pseudonocardia sp. J. Nat. Prod. 2012, 75, 1806-1809.

[5] Guo, F.; Xiang, S.H.; Li, L.Y.; Wang, B.; Rajasärkkä, J.; Gröndahl-Yli-hannuksela, K.; Ai, G.M.; Metsä-Ketelä, M.; Yang, K.Q. Targeted activation of silent natural product biosynthesis pathways by reporter-guided mutant selection. Metab. Eng. 2015, 28, 134-142.

[6] Sasaki, E.; Ogasawara, Y.; Liu, H.W. A biosynthetic pathway for BE-7585A, a 2-thiosugar-containing angucycline-type natural product. J. Am. Chem. Soc. 2010, 132, 7405-7417.

[7] Faust, B.; Hoffmeister, D.; Weitnauer, G.; Westrich, L.; Haag, S.; Schneider, P.; Decker, H.; Künzel, E.; Rohr, J.; Bechthold, A. Two new tailoring enzymes, a glycosyl-transferase and an oxygenase, involved in biosynthesis of the angucycline antibiotic urdamycin A in Streptomyces fradiae Tü2717. Microbiology. (Reading, Engl.) 2000, 146, 147-154.

[8] Dashti, Y.; Grkovic, T.; Abdelmohsen, U.R.; Hentschel, U.; Quinn, R.J. Actinomycete metabolome induction/suppression with N-acetylglucosamine. J. Nat. Prod. 2017, 80, 828-836.

[9] Guo, Z.K.; Liu, S.B.; Jiao, R.H.; Wang, T.; Tan, R.X.; Ge, H.M. Angucyclines from an insect-derived actinobacterium Amycolatopsis sp. HCa1 and their cytotoxic activity. Bioorg. Med. Chem. Lett. 2012, 22, 7490-7493.

[10] Brötz, E.; Bilyk, O.; Kröger, S.; Paululat, T.; Bechthold, A.; Luzhetskyy, A. Amycomycins C and D, new angucyclines from Kitasatospora sp. Tetrahedron Lett. 2014, 55, 5771-5773.

[11] Rasmussen, R.R.; Nuss, M.E.; Scherr, M.H.; Mueller, S.L.; McAlpine, J.B.; Mitscher, L.A. Benzanthrins A and B, a new class of quinone antibiotics. II. Isolation, elucidation of structure and potential antitumor activity. J. Antibiot. 1986, 39, 1515-1526.

[12] Uesato, S.; Tokunaga, T.; Takeuchi, K. Novel angucycline compound with both antigastrin- and gastric mucosal protective-activities. Bioorg. Med. Chem. Lett. 1998, 8, 1969-1972.

[13] Zhang, Y.L.; Gan, M.L.; Lin, S.; Liu, M.T.; Song, W.X.; Zi, J.C.; Wang, S.J.; Li, S.; Yang, Y.C.; Shi, J.G. Glycosides from the bark of Adina polycephala. J. Nat. Prod. 2008, 71, 905-909.

[14] Ding, Y.Q.; Li, X.C.; Ferreira, D. Theoretical calculation of electronic circular dichroism of a hexahydroxydiphenoyl-containing flavanone glycoside. J. Nat. Prod. 2009, 72, 327-335.

[15] Liu, Y.; Ding, S.Y.; Dietrich, R.; Märtlbauer, E.; Zhu, K. Corrigendum: A biosurfactant-inspired heptapeptide with improved specificity to kill MRSA. Angew. Chem. Int. Ed. Engl. 2017, 56, 5651.

[16] Xi, L.J.; Ruan, J.S.; Huang, Y. Diversity and biosynthetic potential of culturable actinomycetes associated with marine sponges in the China Seas. Int. J. Mol. Sci. 2012, 13, 5917-5932.

[17] Heuer, H.; Krsek, M.; Baker, P.; Smalla, K.; Wellington, E.M. Analysis of actinomycete communities by specific amplification of genes encoding 16S rRNA and gel-electrophoretic separation in denaturing gradients. Appl. Environ. Microbiol. 1997, 63, 3233-3241.

[18] Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.P.; Izmaylov, A.F.; Bloino, J.; Zheng, G.; Sonnenberg, J.L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J.A.; Peralta, J.E.; Ogliaro, F.; Bearpark, M.; Heyd, J.J.; Brothers, E.; Kudin, K.N.; Staroverov, V.N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J.C.; Iyengar, S.S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J.M.; Klene, M.; Knox, J.E.; Cross, J.B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Martin, R.L.; Morokuma, K.; Zakrzewski, V.G.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Dapprich, S.; Daniels, A.D.; Farkas, O.; Foresman, J.B.; Ortiz, J.V.; Cioslowski, J.; Fox, D.J. Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT. 2009.

[19] Bruhn, T.; Schaumlöffel, A.; Hemberger, Y.; Bringmann, G. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality. 2013, 25, 243-249.

深海链霉菌Streptomyces sp. PKU-MA01297中发现的两个葡萄糖苷化角环素

Two glucosylated angucyclines from deep-sea-derived Streptomyces sp. PKU-MA01297

RichHTML

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	石金徽, 李睿悦, 杨思雨, 张红梅. 川芎的植物化学、生物活性及质量评价研究综述[J]. 中国药学(英文版), 2020, 29(11): 755-779.
[2]	王亚文, 段晓峰, 程晓晓, 张邈鑫, 李丽, 赵丁. 桑叶及其提取物对肠道功能的调节作用[J]. 中国药学(英文版), 2020, 29(11): 780-792.
[3]	徐露露, 尚展鹏, 柴跃, 张扬, 余蓉, 叶敏, 乔雪. 正向×反相离线二维液相色谱-轨道质谱联用检测通脉颗粒中的微量成分[J]. 中国药学(英文版), 2020, 29(11): 793-803.
[4]	徐方方, 孙彪, 张晓琦, 刘博. 北枳椇子中的黄酮碳苷类成分[J]. 中国药学(英文版), 2020, 29(11): 813-818.
[5]	Eric Wei Chiang Chan, Oi Yoon Michelle Soo, Yong Hui Tan, Siu Kuin Wong, Hung Tuck Chan. Nobiletin and tangeretin (citrus polymethoxyflavones): an overview on their chemistry, pharmacology and cytotoxic activities against breast cancer[J]. 中国药学(英文版), 2020, 29(7): 443-454.
[6]	王慧楠, 张景珍, 崔曰新, 王思雨, 高慧, 张瑶, 王新杰, 杨子烨, 陈梦雨, 王佩华, 张桂梅, 王英姿, 张超. 千金子制霜前后UPLC-Q-TOF/MS化学成分分析研究[J]. 中国药学(英文版), 2020, 29(7): 470-479.
[7]	徐云玲, 王昱霁, 江石平, 蔡婷婷, 王楠楠, 刘霞, 朱婉萍. 北五味子化学成分的研究[J]. 中国药学(英文版), 2020, 29(7): 480-486.
[8]	陈静, 程丽, 王富乾, 汪选斌, 张勇慧, 郝新才. 王瓜化学成分研究[J]. 中国药学(英文版), 2020, 29(6): 431-438.
[9]	范靖然, 董泽源, 匡易, 周艳霞, 乔雪, 叶敏. 乌拉尔甘草地上部分的化学成分及其PTP1B与α-葡萄糖苷酶抑制活性研究[J]. 中国药学(英文版), 2020, 29(5): 305-313.
[10]	吴翠, 徐靓, 徐博, 李卓俊, 巢志茂. 生地黄和熟地黄中5-羟甲基糠醛的含量与色泽的相关性研究[J]. 中国药学(英文版), 2020, 29(5): 314-321.
[11]	Makhmur Ahmad, Mohammad Rashid, Babar Ali, Shamshir Khan, Naseem Akhtar, Mohd Faiyaz Khan, Bibhu Prasad Panda. Immobilization of β-glucuronidase: biocatalysis of glycyrrhizin to 18β-glycyrrhetinic acid and in-silico lead finding[J]. 中国药学(英文版), 2020, 29(5): 333-340.
[12]	黄晋, 杨玲馨, 杨宁, 袁博文, 张浩, 王梦月. 荨麻抑制前列腺增生药理作用研究[J]. 中国药学(英文版), 2020, 29(4): 236-243.
[13]	刘继梅, 陈明华, 陈日道, 解可波, 陈大伟, 司书毅, 戴均贵. 内生真菌Periconia sp. F-31中的三个新化合物[J]. 中国药学(英文版), 2020, 29(4): 244-251.
[14]	杨红帅, 刘秋怡, 殷卫东, 解满江, 吉翔, 邵双宇, 梁鸿, 屠鹏飞, 张庆英. 酸枣仁和滇枣仁的HPLC指纹图谱分析及鉴别[J]. 中国药学(英文版), 2020, 29(4): 252-259.
[15]	梁晓霞, 熊城, 高迎迎, 范巧佳. 天麻内生真菌提取物抗氧化活性及天麻素的测定[J]. 中国药学(英文版), 2020, 29(3): 206-213.