Study on Isolation, Identification and Bioactivity of Desferrioxamine E and Its Metal-Complexes from Streptacidiphilus jiangxiensis

doi:10.6023/cjoc202401038

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2377-2380.DOI: 10.6023/cjoc202401038 Previous Articles Next Articles

江西嗜酸链霉菌去铁胺E及金属络合物的分离鉴定与生物活性研究

李金达^a^,^b, 程伯涛^b, 黄积武^b^,^*(), 刘文^b^,^*()

a 上海师范大学化学与材料科学学院上海 200233
b 中国科学院上海有机化学研究所生命过程小分子调控全国重点实验室上海 200032

收稿日期:2024-01-30 修回日期:2024-03-11 发布日期:2024-04-09
基金资助:
科技部重大专项(2022YFC2303100); 国家自然科学基金(22193070); 国家自然科学基金(32030002)

Study on Isolation, Identification and Bioactivity of Desferrioxamine E and Its Metal-Complexes from Streptacidiphilus jiangxiensis

Jinda Li^a^,^b, Botao Cheng^b, Jiwu Huang^b(), Wen Liu^b()

a College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200233
b State Key Labratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2024-01-30 Revised:2024-03-11 Published:2024-04-09
Contact: * E-mail: huangjiwu@sioc.ac.cn;wliu@sioc.ac.cn
Supported by:
National Key Research and Development Program of China(2022YFC2303100); National Natural Science Foundation of China(22193070); National Natural Science Foundation of China(32030002)

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Abstract

Research on the genus Streptacidiphilus was mainly focused on the isolation and identification of new species, with relatively less emphasis on the study of secondary metabolites. A new aluminium-complex alumioxamine (3), and two known compounds desferrioxamine E (1) and ferrioxamine E (2) were isolated from the fermentation broth of Streptacidiphilus jiangxiensis CGMCC 4.1857. Their structures were elucidated by MS, IR, NMR and single crystal X-ray diffraction technologies. Structurally, compound 3 features aluminum(III) as the central atom, which is bonded to six oxygen atoms of the ligand, forming a hexadentate complex. Furthermore, in vitro cytotoxicity assays showed that compound 1 exhibited potential inhibitory activity against four human tumor cell lines (Hela, PANC1, A375 and MHCC-97H) at a concentration of 100 μmol/L with cell viability ranging from 4.8% to 66.4%.

Key words: Streptacidiphilus jiangxiensis, secondary metabolites, complexes, cytotoxic activity, crystal structure

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Jinda Li, Botao Cheng, Jiwu Huang, Wen Liu. Study on Isolation, Identification and Bioactivity of Desferrioxamine E and Its Metal-Complexes from Streptacidiphilus jiangxiensis[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2377-2380.

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References 14

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No.	δ_C, type	δ_H (J in Hz)
1/1'/1"	174.1, C	—
2/2'/2"	30.7, CH₂	3.01 (ddd, 15.0, 12.5, 3.0); 2.73 (dt, 15.0, 3.0)
3/3'/3"	24.8, CH₂	3.23 (ddd, 15.0, 12.5, 3.0); 2.67 (dt, 15.0, 3.0)
4/4'/4"	164.1, C	—
5/5'/5"	51.2, CH₂	4.24 (ddd, 13.5, 10.0, 3.0); 3.75 (overlap)
6/6'/6"	26.2, CH₂	2.03~2.13 (m); 1.61~1.68 (m)
7/7'/7"	22.1, CH₂	1.40~1.49 (m, 2H)
8/8'/8"	27.8, CH₂	1.75~1.82 (m, 2H)
9/9'/9"	38.1, CH₂	3.75 overlap; 3.15 dt (14.0, 4.5)

No.	δ_C, type	δ_H (J in Hz)
1/1'/1"	174.1, C	—
2/2'/2"	30.7, CH₂	3.01 (ddd, 15.0, 12.5, 3.0); 2.73 (dt, 15.0, 3.0)
3/3'/3"	24.8, CH₂	3.23 (ddd, 15.0, 12.5, 3.0); 2.67 (dt, 15.0, 3.0)
4/4'/4"	164.1, C	—
5/5'/5"	51.2, CH₂	4.24 (ddd, 13.5, 10.0, 3.0); 3.75 (overlap)
6/6'/6"	26.2, CH₂	2.03~2.13 (m); 1.61~1.68 (m)
7/7'/7"	22.1, CH₂	1.40~1.49 (m, 2H)
8/8'/8"	27.8, CH₂	1.75~1.82 (m, 2H)
9/9'/9"	38.1, CH₂	3.75 overlap; 3.15 dt (14.0, 4.5)

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江西嗜酸链霉菌去铁胺E及金属络合物的分离鉴定与生物活性研究

Study on Isolation, Identification and Bioactivity of Desferrioxamine E and Its Metal-Complexes from Streptacidiphilus jiangxiensis

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