南海软珊瑚共附生真菌Aspergillus sp. EGF15-0-3苯甲醛类化合物研究*

doi:10.11978/2020085

热带海洋学报 ›› 2021, Vol. 40 ›› Issue (4): 63-69.doi: 10.11978/2020085CSTR: 32234.14.2020085

南海软珊瑚共附生真菌Aspergillus sp. EGF15-0-3苯甲醛类化合物研究^*

刘炳新^1,²(), 韦霞¹, 肖细姬¹, 张琪¹, 张翠仙¹()

1.广州中医药大学中药学院, 广东广州 510006
2.康美药业股份有限公司, 广东广州 510627

收稿日期:2020-08-01 修回日期:2020-10-16 出版日期:2021-07-10 发布日期:2020-12-24
通讯作者: 张翠仙
作者简介:刘炳新(1991—), 男, 执业药师, 主要从事中药与天然药物化学研究。email: 414040589@qq.com
基金资助:
广东省自然资源厅广东省海洋经济发展(海洋六大产业)专项资金(粤自然资合)([2020]039);广东省科技计划(2017A020217008);广东省科技计划(2015A020216017);广州中医药大学薪火计划重点项目(XH20170110);国家自然科学基金(81741160);广东省自然科学基金(2014A030313411)

Research on benzaldehydes from the soft coral-associated symbiotic fungus Aspergillus sp. EGF15-0-3

LIU Bingxin^1,²(), WEI Xia¹, XIAO Xiji¹, ZHANG Qi¹, ZHANG Cuixian¹()

1. School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
2. Kangmei Pharmaceutical Co., Ltd, Guangzhou 510627, China

Received:2020-08-01 Revised:2020-10-16 Online:2021-07-10 Published:2020-12-24
Contact: ZHANG Cuixian
Supported by:
Special Project for Marine Economic Development (Six Major Marine Industries) of Guangdong Province Department of Natural Resources of Guangdong Province([2020]039);Science and Technology Planning Project of Guangdong Province(2017A020217008);Science and Technology Planning Project of Guangdong Province(2015A020216017);Fire Plan Project of the Guangzhou University of Chinese Medicine(XH20170110);National Natural Science Foundation of China(81741160);Natural Science Foundation of Guangdong Province(2014A030313411)

摘要/Abstract

摘要：

本文研究了具有克服肿瘤耐药活性的软珊瑚共附生真菌Aspergillus sp. EGF 15-0-3苯甲醛类化学成分。采用硅胶柱层析、十八烷基硅烷键合硅胶层析、Sephadex LH-20层析、高效液相色谱(high performance liquid chromatography, HPLC)等多种方法进行分离纯化; 通过核磁共振波谱(nuclear magnetic resonance, NMR)、质谱(mass spectrometry, MS)等现代波谱分析及物理常数对照等方法进行结构鉴定; 采用MTT法对苯甲醛部位和单体化合物进行克服肿瘤耐药活性研究。从EGF15-0-3的苯甲醛部位共得到9个苯甲醛类化合物, 结构依次为flavoglaucin (1)、tetrahydroauroglaucin (2)、isoaspergin (3)、 isotetrahydroauro-glaucin (4)、dihydroauroglaucin (5)、isodihydroauroglaucin (6)、2-(1',5'-heptadienyl)-3, 6-dihydroxy-5-(3''-methyl-2''-butenyl) benzaldehyde (7)、auro-glaucin (8)和2-(2',3-epoxy-1'-heptenyl)-6-hydroxy-5- (3''methyl-2''-butenyl) benzaldehyde (9)。体外克服肿瘤耐药活性研究表明, 苯甲醛类化合物9具有较强的克服肿瘤耐药活性, 可能是由于其结构2位烷基侧链与3羟基形成吡喃环所致。

关键词: 软珊瑚共附生真菌, Aspergillus sp.EGF15-0-3, 苯甲醛, 克服肿瘤耐药活性

Abstract:

To research the benzaldehydes of the soft coral-associated symbiotic fungus Aspergillus sp. EGF 15-0-3 with the activity of overcoming tumor resistance, the secondary metabolites were isolated by silica gel column chromatography, ODS, Sephadex LH-20, thin layer chromatography, and high performance liquid chromatography (HPLC). The structures of compounds were identified by nuclear magnetic resonance (NMR), mass spectrometry(MS), and literature analysis. Nine benzaldehydes were obtained and elucidated as follows: flavoglaucin (1), tetrahydroauroglaucin (2), isoaspergin (3), isotetrahydroauroglaucin (4), dihydroauroglaucin (5), isodihydroauroglaucin (6), 2-(1',5'-heptadienyl)-3,6-dihydroxy-5- (3''-methyl-2''-butenyl) benzaldehyde (7), auro- glaucin (8), and 2-(2',3-epoxy-1'-heptenyl)-6- hydroxy-5-(3''methyl-2''-butenyl) benzal-dehyde (9). Using the MTT [3-(4, 5)-dimethylthiahiazo (-z-y1)-3, 5-di-phenytetrazoliumromide] method, compound 9 showed strong activity to drug-resistant tumor cell lines H1975/GR. This may be due to the structure of a pyran ring between the 2-position side chain and 3-hydroxyl group.

Key words: Soft coral-associated symbiotic epiphytic fungus, Aspergillus sp. EGF15-0-3, benzaldehydes, overcoming tumor resistance activity

中图分类号:

P735.51

刘炳新, 韦霞, 肖细姬, 张琪, 张翠仙. 南海软珊瑚共附生真菌Aspergillus sp. EGF15-0-3苯甲醛类化合物研究^*[J]. 热带海洋学报, 2021, 40(4): 63-69.

LIU Bingxin, WEI Xia, XIAO Xiji, ZHANG Qi, ZHANG Cuixian. Research on benzaldehydes from the soft coral-associated symbiotic fungus Aspergillus sp. EGF15-0-3[J]. Journal of Tropical Oceanography, 2021, 40(4): 63-69.

图/表 2

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南海软珊瑚共附生真菌Aspergillus sp. EGF15-0-3苯甲醛类化合物研究^*

Research on benzaldehydes from the soft coral-associated symbiotic fungus Aspergillus sp. EGF15-0-3

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