植物内生真菌Leptosphaeria sp.中两个新氧杂蒽酮类化合物leptosphaerins H和I的分离及抗炎活性

doi:10.6040/j.issn.1671-7554.0.2017.142

山东大学学报（医学版） ›› 2017, Vol. 55 ›› Issue (11): 27-31.doi: 10.6040/j.issn.1671-7554.0.2017.142

植物内生真菌Leptosphaeria sp.中两个新氧杂蒽酮类化合物leptosphaerins H和I的分离及抗炎活性

张鹏亮,张龙腾,李爱玲,沈涛,娄红祥,王小宁

山东大学药学院天然产物化学生物学教育部重点实验室, 山东济南 250012

收稿日期:2017-02-15 出版日期:2017-11-10 发布日期:2017-11-10
通讯作者: 王小宁. E-mail:wangxn@sdu.edu.cn E-mail:wangxn@sdu.edu.cn
基金资助:
国家自然科学基金(21472113);山东省科技发展计划(2014GSF118023)

Isolation of Leptosphaerins H and I, two new xanthones from the endophytic fungus Leptosphaeria sp. and their anti-inflammatory activity

ZHANG Pengliang, ZHANG Longteng, LI Ailing, SHEN Tao, LOU Hongxiang, WANG Xiaoning

Key Laboratory of Chemical Biology(Ministry of Education), Department of Natural Product Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, Shandong, China

Received:2017-02-15 Online:2017-11-10 Published:2017-11-10

摘要/Abstract

摘要： 目的对分离自脚骨脆正常植物组织中的内生真菌Leptosphaeria sp. L1201的代谢产物及其生物活性进行研究。方法采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、高效液相色谱等技术对内生真菌Leptosphaeria sp. L1201的代谢产物进行分离,采用核磁共振、高分辨率质谱、X-射线单晶衍射等技术确证化合物的结构;采用一氧化氮(NO)生成抑制试验评价化合物的抗炎活性,并测定化合物对小鼠RAW264.7巨噬细胞的细胞毒性。结果从该株内生真菌培养物的乙酸乙酯提取物中获得2个新的氧杂蒽酮类化合物,并鉴定为leptosphaerins H(1)和I(2);化合物1和2能够抑制小鼠RAW264.7巨噬细胞中NO形成,IC₅₀值分别为126.7 μmol/L和72.6 μmol/L。结论 Leptosphaerins H(1)和I(2)为新化合物,并在RAW264.7细胞中具有一定的抗炎活性。

关键词: 氧杂蒽酮, 内生真菌, 抗炎活性

Abstract: Objective To study the metabolites from the strain of the fungus Leptosphaeria sp. L1201 which was isolated from healthy tissues of the plant Casearia balansae(Flacourtiaceae). Methods The compounds were isolated by different chromatographic methods, including silica gel and Sephadex LH-20 column chromatography as well as high performance liquid chromatography, and the structures of the compounds were determined on the basis of extensive spectroscopic techniques including HRMS, 1D and 2D NMR experiments and single-crystal X-ray diffraction analysis. Anti-inflammatory effects of isolated compounds were evaluated using nitric oxide(NO)inhibitory assay in murine RAW 264.7 macrophages. Results Two new xanthones were isolated from the EtOAc extract of the culture of the fungus Leptosphaeria sp. L1201 and their structures were identified as leptosphaerins H(1)and I(2). Compounds 1 and 2 inhibited the NO formation with IC₅₀ values being 126.7 and 72.6 μmol/L, respectively. Conclusion Leptosphaerins H and I are new xanthones, which show anti-inflammatory activity in RAW264.7 cells.

Key words: Endophytic fungi, Xanthone, Anti-inflammatory activity

中图分类号:

R914

张鹏亮,张龙腾,李爱玲,沈涛,娄红祥,王小宁. 植物内生真菌Leptosphaeria sp.中两个新氧杂蒽酮类化合物leptosphaerins H和I的分离及抗炎活性[J]. 山东大学学报（医学版）, 2017, 55(11): 27-31.

ZHANG Pengliang, ZHANG Longteng, LI Ailing, SHEN Tao, LOU Hongxiang, WANG Xiaoning. Isolation of Leptosphaerins H and I, two new xanthones from the endophytic fungus Leptosphaeria sp. and their anti-inflammatory activity[J]. JOURNAL OF SHANDONG UNIVERSITY (HEALTH SCIENCES), 2017, 55(11): 27-31.

参考文献 25

[1]	郭良栋. 内生真菌研究进展[J]. 菌物系统, 2001, 20(1): 148-152. GUO Liangdong. Advances of researches on endophytic fungi[J]. Mycosystema, 2001, 20(1): 148-152.
[2]	Gao XX, Zhou H, Qu LH, et al. High diversity of endophytic fungi from the pharmaceutical plant, Heterosmilax japonica Kunth revealed by cultivation-independent approach[J]. FEMS Microbiology Lett, 2005, 249(2): 255-266.
[3]	Strobel G, Daisy B. Bioprospecting for microbial endophytes and their natural products[J]. Microbiol Mol Biol Rev, 2003, 67(4): 491-502.
[4]	Gunatilaka AAL. Natural products from plant-associated microorganisms: distribution, structural diversity, bioactivity, and implications of their occurrence[J]. J Nat Prod, 2006, 69(3): 509-526.
[5]	Wang XN, Bashyal BP, Gunatilaka AAL, et al. Smar-daesidins A—G, isopimarane and 20-nor-isopimarane diterpenoids from smardaea sp., a fungal endophyte of the moss Ceratodon purpureus[J]. J Nat Prod, 2011, 74(10): 2052-2061.
[6]	Li W, Lee C, Shim SH, et al. Isochromans and related constituents from the endophytic fungus Annulohypoxylon truncatum of Zizania caduciflora and their antiInflammatory effects[J]. J Nat Prod, 2017, 80(1): 205-209.
[7]	Zhang M, Zhao JL, Dai JG, et al. Neural anti-inflammatory sesquiterpenoids from the endophytic fungus trichoderma sp. Xy24[J]. J Asian Nat Prod Res, 2016, 18(11): 1-9.
[8]	Evidente A, Sparapano L, Motta A, et al. A phytotoxic pimarane diterpene of Sphaeropsis sapinea f. sp. cupressi, the pathogen of a canker disease of cypress[J]. Phytochemistry, 1996, 42(6): 1541-1546.
[9]	Evidente A, Venturi V, Masi M, et al. In vitro antibacterial activity of sphaeropsidins and chemical derivatives toward Xanthomonas oryzae pv. oryzae, the causal agent of rice bacterial blight[J]. J Nat Prod, 2011, 74(12): 2520-2525.
[10]	Zhang HW, Song YC, Tan RX. Biology and chemistry of endophytes[J]. Nat Prod Rep, 2006, 23(5): 753-771.
[11]	Tan RX, Zou WX. Endophytes-a rich source of functional metabolites[J]. Nat Prod Rep, 2001, 18(4): 448-459.
[12]	Sushanto G, Gitshree D, Kumar PJ, et al. Endophytes: a treasure house of bioactive compounds of medicinal importance[J]. Front Microbiol, 2016, 7(148): 1538-1550.
[13]	Ruba AA, Mohan VR. Anti-inflammatory activity of whole plant extract of Andrographis echioides against carrageenan induced paw edema[J]. J Pharm Sci Rev Res, 2016, 37(2): 110-113.
[14]	魏伟. 炎症免疫反应软调节[J].中国药理学通报, 2016, 32(3): 297-303.
[15]	Kiem PV, Huyen LT, Hang DT, et al. Sesquiterpene derivatives from marine sponge Smenospongia cerebriformis and their anti-inflammatory activity[J]. Bioorg Med Chem Lett, 2017, 27(7): 1525-1529.
[16]	Choi SY, Choi JY, Lee JM, et al. Tartary buckwheat on nitric oxide-induced inflammation in RAW264.7 macrophage cells[J]. Food Funct, 2015, 6(8): 2664-2670.
[17]	Zhou MX, Xuan W, Li AL, et al. Screening of traditional Chinese medicines with therapeutic potential on chronic obstructive pulmonary disease through inhibiting oxidative stress and inflammatory response[J]. BMC Complement Altern Med, 2016, 16(1): 1-11.
[18]	Wang XL, Di XX, Shen T, et al. Chemical constituents from Cicuta virosa Linnaeus and their reversal effects on doxorubicin-resistant human myelogenous leukemia(K562/A02)cells[J]. Chin Chem Lett, 2016, 27(7): 1013-1016.
[19]	Lin J, Liu SC, Sun BD, et al. Polyketides from the ascomycete fungus Leptosphaeria sp.[J]. J Nat Prod, 2010, 73(5): 905-910.
[20]	马翠苓, 潘旭东, 马爱军, 等. 趋化因子CXCL16与动脉粥样硬化性卒中[J]. 国际脑血管病杂志, 2012, 20(3): 223-226. MA Cuiling, PAN Xudong, MA Aijun, et al. Chemotatic factor CXCL16 and atherosclerotic stroke[J]. Int J Cerebrovasc Dis, 2012, 20(3): 223-226.
[21]	于水莲, 陶怡, 王羿升, 等. 炎症因素与早期类风湿关节炎心血管病变相关性研究[J]. 中华风湿病学杂志, 2016, 20(11): 739-745. YU Shuilian, TAO Yi, WANG Yisheng, et al. The correlation between inflammatory burden with cardiovascular disease in patient with early rheumatoid arthritis[J]. Chin J Rheumatol, 2001, 18(4): 448-459.
[22]	刘俊田. 动脉粥样硬化发病的炎症机制的研究进展[J].西安交通大学学报(医学版), 2015, 36(2): 141-152. LIU Juntian. Progress in inflammatory pathogenesis of atherosclerosis[J]. Journal of Xi’an Jiaotong University(Medical Sciences), 2015, 36(2): 141-152.
[23]	Shai SS, David F, Brian AK, et al. Defective signaling in the JAK-STAT pathway tracks with chronic inflammation and cardiovascular risk in aging humans[J]. Cell Press, 2016, 3(4): 374-384.
[24]	Moncada S. Nitric oxide: discovery and impact on clinical medicine[J]. J Roy Soc Med, 1999, 92(4): 164-169.
[25]	叶翎, 孙国燕, 孙玉瑶, 等. 慢性低度炎症与糖尿病关系的研究进展[J].医学综述, 2014, 20(21): 3846-3848. YE Ling, SUN Guoyan, SUN Yuyao, et al. Advancement in studies on vascular endothelial growth factor in ischemic stroke[J]. Medical Recapitulate, 2014, 20(21): 3846-3848.

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植物内生真菌Leptosphaeria sp.中两个新氧杂蒽酮类化合物leptosphaerins H和I的分离及抗炎活性

Isolation of Leptosphaerins H and I, two new xanthones from the endophytic fungus Leptosphaeria sp. and their anti-inflammatory activity

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