研究简报

1株红树来源真菌 Penicillium janthinellum XLN32122 次级代谢产物与生物活性研究

  • Shi ,
  • Jueying ,
  • Qiu ,
  • Yikang ,
  • Lan ,
  • Jing ,
  • Xu ,
  • Zhenyang ,
  • Wang ,
  • Yi ,
  • Li ,
  • Jiaxiang ,
  • Luo ,
  • Youping ,
  • Huang ,
  • Guolei ,
  • Zheng ,
  • Caijuan
展开
  • a海南师范大学热带药用资源化学教育部重点实验室 海口 571158
    b海南师范大学化学与化工学院 热带药用植物化学海南省重点实验室 海口 571158

收稿日期: 2025-06-18

  修回日期: 2025-09-18

  网络出版日期: 2025-10-30

基金资助

国家自然科学基金(No. 32160108)、海南省重点研发计划项目(No. ZDYF2024SHFZ116)、海南省院士创新平台专项 (No. YSPTZX202309)、海南省高等学校科学研究项目 (No. Hnky2022ZD-6 ) 、海南师范大学“大学生创新训练项目” (No. 202411658006 ) 资助

Research on Secondary Metabolites from a Mangrove-Derived Fungus Penicillium janthinellum XLN32122 and their Biological Activities

  • 石珏莹 ,
  • 仇毅康 ,
  • 兰晶 ,
  • 徐振洋 ,
  • 王熠 ,
  • 李嘉祥 ,
  • 罗由萍 ,
  • 黄国雷 ,
  • 郑彩娟
Expand
  • aKey Laboratory of Tropical Medicinal Resources Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158
    bKey Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158

Received date: 2025-06-18

  Revised date: 2025-09-18

  Online published: 2025-10-30

Supported by

National Natural Science Foundation of China (No. 32160108), Hainan Province Science and Technology Special Fund (No. ZDYF2024SHFZ116), Innovation Center for Academicians of Hainan Province, and the Specific Research Fund of the Innovation Center for Academicians of Hainan Province (No. YSPTZX202309), the Natural Science Foundation of the Hainan Higher Education Institutions of China (No. Hnky2022ZD-6 ), Hainan Normal University National College Student Innovation Training Program (No. 202411658006 ).

摘要

本研究对1株红树来源真菌 Penicillium janthinellum XLN32122的次级代谢产物进行研究,从中分离得到1个新的含有1,2-氧杂十二环的杂环二肽化合物 trichodermamide H (1)和3个类似物 (2~4),以及3个已知的聚酮类化合物 (5~7)。综合运用一维、二维核磁共振波谱、高分辨质谱和电子圆二色性 (ECD) 光谱确定了化合物1的平面结构和绝对构型。体外抗炎活性结果显示,化合物3对LPS诱导的RAW 264.7细胞中NO的产生具有显著的抑制活性,IC50值为13.13 ± 0.005 μM,强于阳性对照药物地塞米松,IC50值为136.84 ± 1.33 μM。体外抗菌活性测试表明,化合物3对耐甲氧西林金黄色葡萄球菌具有一定的抑制活性,其IC50值为12.5 μg/mL,阳性对照万古霉素的IC50值为1.56 μg/mL。

本文引用格式

Shi , Jueying , Qiu , Yikang , Lan , Jing , Xu , Zhenyang , Wang , Yi , Li , Jiaxiang , Luo , Youping , Huang , Guolei , Zheng , Caijuan . 1株红树来源真菌 Penicillium janthinellum XLN32122 次级代谢产物与生物活性研究[J]. 有机化学, 0 : 0 . DOI: 10.6023/cjoc202506026

Abstract

A new heterocyclic dipeptide with a highly functionalized 1,2-oxazadecaline core, named trichodermamide H (1), and three known analogues (2-4), along with three known polyketides (5-7), were isolated from the fermentation extract of the mangrove-derived fungus Penicillium janthinellum XLN32122. The structure of 1 was elucidated on the basis of extensive 1D and 2D NMR spectra data analysis, HR-ESI-MS, electronic circular dichroism (ECD) calculations. Compound 3 demonstrated better inhibitory effects on nitric oxide (NO) production in LPS-induced RAW 264.7 cells, with an IC50 value of 13.13±0.005 μM than that of the positive control dexamethasone (IC50=136.84±1.33 μM). Compound 3 exhibited antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA), with an IC50 value of 12.5 μg/mL, positive control vancomycin (IC50=1.563 μg/mL).

参考文献

[1] Koul M.; Singh S. Anticancer Drugs 2017, 28, 11-30.
[2] Li H.; Fu Y.; Song F.; Xu X. Chem.Biodivers. 2023, 20, e202301278.
[3] de Carvalho, A.C.; Ogawa, C.Y.; Rodrigues, L.D.; de Medeiros, L.S.; Veiga, T.A.M. Lymphoma 2021, 62, 2079-2093.
[4] Matsukuma S.; Nishizuka Y.; Watanabe J.; Okuda T. Mycoscience 1994, 35, 183-186.
[5] Zheng C.-J.; Xu L.-L.; Li Y.-Y.; Han T.; Zhang Q.-Y.; Ming Q.-L.; Rahman K.; Qin, L.-P. Appl. Microbiol. Biotechnol. 2013, 97, 7617-7625.
[6] Marinho A.M.D.; Rodrigues, E.; Moitinho, M.D.R.; Santos, L.S. B. J. Braz. Chem. Soc. 2005, 16, 280-283.
[7] Tapfuma K.I.; Sebola T.E.; Uche-Okereafor, N.; Koopman, J.; Hussan, R.; Makatini, M.M.; Mekuto, L.; Mavumengwana, V. Data Brief 2020, 28, 104959.
[8] Widden P.; Parkinson, A.D. Can. J. Microbiol. 1978, 24, 415-421.
[9] Sun T.-T.; Yang J.-K.; Zhu H.-J.; Pan L.; Cao F. Chem. Nat. Compd. 2020, 56, 968-970.
[10] Cui H.; Li X.-D.; Li M.-Q.; Lu F.-M.; Wang Y.-H.; Liu D.; Kang, J.-G. Chin. J. Mar. Drugs 2017, 36, 41-46.
[11] Smetanina O.F.; Kalinovsky A.I.; Khudyakova Y.V.; Pivkin M.V.; Dmitrenok P.S.; Fedorov S.N.; Ji H.; Kwak J.Y.; Kuznetsova T.A.J. Nat. Prod. 2007, 70, 906-909.
[12] Yang L.-J.; Lv L.; Han Z.; Gu Y.-C.; Li X.; Shao C.-L.; Liu Z.-Q.; Wang, C.-Y. Chin. J. Chem. 2025, 43, 268-274.
[13] Zeng F.-R.; Chen C.-M.; Al Chnani, A.A.; Zhou, Q.; Tong, Q.-Y.; Wang, W.-J.; Zang, Y.; Gong, J.-J.; Wu, Z.-D.; Liu, J.-J.; Wang, J.-P.; Zhu, H.-C.; Zhang, Y.-H. Bioorg. Chem. 2019, 86, 176-182.
[14] Zhu M.-L.; Zhang X.-M.; Feng H.-M.; Dai J.-J.; Li J.; Che Q.; Gu Q.-Q.; Zhu T.-J.; Li D.-H.J. Nat. Prod. 2017, 80, 71-75.
[15] Wang W.-J.; Liao L.-X.; Huang Z.-D.; Wei F.-T.; Yang X.-L. ACS Omega 2022, 7, 35280-35287.
[16] Zeng F.-R.; Chen C.-M.; Al Chnani, A.A.; Zhou, Q.; Tong, Q.-Y.; Wang, W.-J.; Zang, Y.; Gong, J.-J.; Wu, Z.-D.; Liu, J.-J.; Wang, J.-P.; Zhu, H.-C.; Zhang, Y.-H. Bioorg. Chem. 2019, 86, 176-182.
[17] Ye X.; Anjum K.; Song T.; Wang W.; Yu S.; Huang H.; Lian X.-Y.; Zhang Z. Nat. Prod. Res. 2015, 30, 1156-1161.
[18] Aoki Y.; Yamazaki T.; Kondoh M.; Sudoh Y.; Nakayama N.; Sekine Y.; Shimada H.; Arisawa M. J.Antibiot. 1992, 45, 160-170.
[19] Cui H.; Li X.-D.; Li M.-Q.; Lu F.-M.; Wang Y.-H.; Liu D.; Kang, J.-G. Chin. J. Mar. Drugs 2017, 36, 41-46.
[20] Wang H.; Li Y.-J.; Wang Y.-F.; Shi, T.; Wang, B. Fermentation 2024, 10, 157.
[21] Qiao S.-J.; Zhai L.; Huang S.-H.; Hong R. J.Fujian Normal Univ. 2020, 36, 1-16.
[22] Yan L.-H.; Li X.; Wang, B.-G. Nat. Prod. Rep. 2023, 40, 1874-1900.
[23] Liu J.-Y.; Jiang Y.-Y.; Li P.-J.; Yao B.; Song Y.-J.; Gao J.-X.; Said G.; Gao Y.; Lai J.-Y.; Shao, C.-L. Mar. Life Sci.Technol. 2024, 6, 502-514.
[24] Liao H.-X.; Zheng C.-J.; Huang G.-L.; Mei R.-Q.; Nong X.-H.; Shao T.-M.; Chen G.-Y.; Wang C.-Y.J. Nat. Prod. 2019, 82, 2211-2219.
[25] Wang B.; Zeng W.-N.; Li G.-Y.; Xiao M.; Wei F.-F.; Luo Y.-P.; Niu Z.-G.; Huang G.-L.; Zheng, C.-J. Chin. J. Org.Chem. 2023, 43, 332-337. (in Chinese)
[王斌, 曾尾女, 李杲钰, 肖媚, 韦方芳, 罗由萍, 钮智刚, 黄国雷, 郑彩娟. 有机化学, 2023, 43, 332-337.]
[26] Bai M.; Huang G.-L.; Mei R.-Q.; Wang B.; Luo Y.-P.; Nong X.-H.; Chen G.-Y.; Zheng C.-J. Mar. Drugs. 2019, 17, 433.
[27] Bai M.; Zheng C.-J.; Chen G.-Y.J. Nat. Prod. 2021, 84, 2104-2110.
[28] Bai M.; Zheng C.-J.; Huang G.-L.; Mei R.-Q.; Wang B.; Luo Y.-P.; Zheng C.; Niu Z.-G.; Chen G.-Y.J. Nat. Prod. 2019, 82, 1155-1164.
[29] Zeng W.-N.; Cai J.; Wang B.; Chen L.-Y.; Pan C.-X.; Chen S.-J.; Huang G.-L.; Zheng C.-J.J. Asian Nat. Prod. Res. 2022, 24, 679.
[30] Garo, E; Starks C.M.; Jensen P.R.; Fenical W.; Lobkovsky E.; Clardy J. J. Nat. Prod. 2003, 66, 423-426.
[31] Zhu M.-L.; Yang, Z., Feng H.-M.; Gan Q.; Che Q.; Zhu T.-J.; Gu Q.-Q.; Han B.-N.; Li D.-H. RSC Advances 2017, 7, 48019-48024.
[32] Kimura Y.; Shiojima K.; Nakajima H.; Hamasaki T. Biosci. Biotechnol. Biochem. 1992, 56, 1138-1139.
[33] Huang H.; Cao Y.; Tian L.; Lin W.; Zhang K. Chem. Nat. Compd. 2014, 50, 402-404.
[34] Stewart M.; Capon R.J.; Lacey E.; Tennant S.; Gill J.H.J. Nat. Prod. 2005, 68, 581-584.
[35] Zhu M.-L.; Zhang X.-M.; Feng H.-M.; Dai J.-J.; Li J.; Che Q.; Gu Q.-Q.; Zhu T.-J.; Li D.-H.J. Nat. Prod. 2017, 80, 71-75.
[36] Jans P.E.; Mfuh A.M.; Arman H.D.; Shaffer C.V.; Larionov O.V.; Mooberry S.L.J. Nat. Prod., 2017, 80, 676-683.
[37] Sirimangkalakitti N.; Lin J.-Y.; Harada K.; Setiawan A.; Arisawa M.; Arai M. Molecules, 2024, 29, 2048.
[38] Gaussian 09 [computer program], Gaussian, Inc.,Gaussian 09 [computer program], Gaussian, Inc., Wallingford CT, 2013.
[39] Pescitelli G.; Bruhn T. Chirality 2016, 28, 466-474.
[40] Bruhn T.; Schaumloffel A.; Hemberger Y.; Bringmann G. Chirality 2013, 25, 243-249.
[41] Dirsch V.; Stuppner H.; Vollmar A.Planta Med. 1998, 64, 423.
[42] Wang J.-F.; Cong Z.-W.; Huang X.-L.; Hou C.-X.; Chen W.-H.; Tu Z.-C.; Huang D.-Y.; Liu Y.-H. Org. Lett. 2018, 20, 1371-1374.
文章导航

/