Citation: Juan He, Jiao-Xian Du, Meng Wang, Xiao-Dong Luo, Tao Feng. Irpexlactones A and B, a pair of ring-rearranged tremulane sesquiterpenoids from the basidiomycete Irpex lacteus and their anti-inflammatory activity[J]. Chinese Chemical Letters, ;2025, 36(10): 110769. doi: 10.1016/j.cclet.2024.110769 shu

Irpexlactones A and B, a pair of ring-rearranged tremulane sesquiterpenoids from the basidiomycete Irpex lacteus and their anti-inflammatory activity

Juan He ^{a, 1} ,
Jiao-Xian Du ^{a, b, 1} ,
Meng Wang ^a ,
Xiao-Dong Luo ^{b, *,} ,
Tao Feng ^{a, b, c, *,}

a.
School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China
b.
Yunnan Characteristic Plant Extraction Laboratory, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650500, China
c.
State Key Laboratory of Applied Microbiology Southern China, Institute of Microbiology, Guandong Academy of Sciences, Guangzhou 510070, China

xdluo@ynu.edu.cn

tfeng@mail.scuec.edu.cn

Received Date: 30 September 2024
Revised Date: 12 December 2024
Accepted Date: 17 December 2024
Available Online: 19 December 2024

Figures(7)

Two unusual sesquiterpenoids, irpexlactones A (1) and B (2), were isolated from cultures of the basidiomycete Irpex lacteus. Their structures were established by means of spectroscopic methods, the single crystal X-ray diffraction, as well as electronic circular dichroism (ECD) calculations. They possess a novel carbon skeleton with a 5/6/3-fused ring system that may derive from tremulane type sesquiterpenoids with ring-rearrangement. Both compounds show significant inhibitory activities against nitric oxide production with half maximal inhibitory concentration (IC₅₀) values of 2.2 and 1.4 µmol/L, respectively. Their anti-inflammatory effects were further evaluated by enzyme-linked immunosorbent assay (ELISA) and Western blot.
- Irpex lacteus,
- Natural sesquiterpenoids,
- Irpexlactones A and B,
- X-ray diffraction,
- NO production inhibition,
- Anti-inflammatory activity
1. [1]
  J.E. Galagan, M.R. Henn, L.J. Ma, et al., Genome Res. 15 (2015) 1620–1631.
2. [2]
  R.J. Cox, T.A.M. Gulder, Nat. Prod. Rep. 40 (2023) 7–8. doi: 10.1039/d2np90047e
3. [3]
  A. Schueffler, T. Anke, Nat. Prod. Rep. 31 (2014) 1425–1448. doi: 10.1039/C4NP00060A
4. [4]
  M. Blackwell, Am. J. Bot. 98 (2011) 426–438. doi: 10.3732/ajb.1000298
5. [5]
  D. Bass, T.A. Richards, Fungal Biol. Rev. 25 (2011) 159–164. doi: 10.1016/j.fbr.2011.10.003
6. [6]
  B.M. Fraga, Nat. Prod. Rep. 27 (2010) 1681–1708. doi: 10.1039/c0np00007h
7. [7]
  J. Li, Z. Cui, Y. Li, et al., Chin. Chem. Lett. 33 (2022) 4257–4260. doi: 10.1016/j.cclet.2022.01.084
8. [8]
  X.J. Wang, J.L. Xin, H. Xiang, et al., Chin. Chem. Lett. 35 (2024) 109682. doi: 10.1016/j.cclet.2024.109682
9. [9]
  D. Chen, J. Li, X. Xu, et al., Chin. Chem. Lett. 35 (2024) 109451. doi: 10.1016/j.cclet.2023.109451
10. [10]
  M.B. Quin, C.M. Flynn, C. Schmidt-Dannert, Nat. Prod. Rep. 31 (2014) 1449–1473. doi: 10.1039/C4NP00075G
11. [11]
  Q. Dai, F.L. Zhang, T. Feng, J. Fungi 7 (2021) 1026. doi: 10.3390/jof7121026
12. [12]
  X.Y. Yang, T. Feng, Z.H. Li, et al., Org. Lett. 14 (2012) 5382–5384. doi: 10.1021/ol302468a
13. [13]
  W. Li, J. He, T. Feng, et al., Org. Lett. 20 (2018) 8019–8021. doi: 10.1021/acs.orglett.8b03595
14. [14]
  H.X. Yang, H.L. Ai, T. Feng, et al., Org. Lett. 20 (2018) 8069–8072. doi: 10.1021/acs.orglett.8b03735
15. [15]
  H.L. Ai, B.B. Shi, W. Li, et al., Org. Chem. Front. 9 (2022) 1814–1819. doi: 10.1039/d1qo01887f
16. [16]
  J. He, W.W. Yu, M. Isaka, et al., Org. Biomol. Chem. 20 (2022) 7278–7283. doi: 10.1039/d2ob01443b
17. [17]
  X.M. Dong, X.H. Song, K.B. Liu, et al., Mycosystema 36 (2017) 28–34. doi: 10.1117/12.2252600
18. [18]
  J.H. Ding, T. Feng, BK, et al., Tetrahedron Lett. 54 (2013) 2651–2654. doi: 10.1016/j.tetlet.2013.03.038
19. [19]
  J.H. Ding, Z.H. Li, T. Feng, et al., Fitoterapia 125 (2018) 245–248. doi: 10.1016/j.fitote.2017.12.001
20. [20]
  H.P. Chen, Z.Z. Zhao, Z.H. Li, et al., Nat. Prod. Bioprospect. 8 (2018) 113–119. doi: 10.1007/s13659-018-0157-y
21. [21]
  R. Chen, T. Feng, M. Li, et al., Org. Lett. 24 (2022) 5669–5673. doi: 10.1021/acs.orglett.2c01975
22. [22]
  C. Chatgilialoglu, C. Ferreri, M. Guerra, et al., J. Am. Chem. Soc. 124 (2002) 10765–10772. doi: 10.1021/ja0261731
23. [23]
  T. Feng, X.Q. Gan, Y.L. Zhao, et al., J. Nat. Prod. 82 (2019) 45–50. doi: 10.1021/acs.jnatprod.8b00460
24. [24]
  X.F. Zhang, H.F. Li, H. Liu, et al., Bioorg. Chem. 151 (2024) 107684. doi: 10.1016/j.bioorg.2024.107684
1. [1]
  Jinyan Zhang , Fen Liu , Qian Jin , Xueyi Li , Qiong Zhan , Mu Chen , Sisi Wang , Zhenlong Wu , Wencai Ye , Lei Wang . Discovery of unusual phloroglucinol–triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking. Chinese Chemical Letters, 2024, 35(6): 108881-. doi: 10.1016/j.cclet.2023.108881
2. [2]
  Wei Li , Guoqiang Feng , Ze Chang . Teaching Reform of X-ray Diffraction Using Synchrotron Radiation in Materials Chemistry. University Chemistry, 2024, 39(3): 29-35. doi: 10.3866/PKU.DXHX202308060
3. [3]
  Yan-Jiang Li , Shu-Lei Chou , Yao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389
4. [4]
  Jingqi Ma , Huangjie Lu , Junpu Yang , Liangwei Yang , Jian-Qiang Wang , Xianlong Du , Jian Lin . Rational design and synthesis of a uranyl-organic hybrid for X-ray scintillation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100275-100275. doi: 10.1016/j.cjsc.2024.100275
5. [5]
  Xin Dong , Jing Liang , Zhijin Xu , Huajie Wu , Lei Wang , Shihai You , Junhua Luo , Lina Li . Exploring centimeter-sized crystals of bismuth-iodide perovskite toward highly sensitive X-ray detection. Chinese Chemical Letters, 2024, 35(6): 108708-. doi: 10.1016/j.cclet.2023.108708
6. [6]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
7. [7]
  Mengyu Chen , Qinglin Zhou , Tianyun Qin , Ningyao Sun , Yuxi Chen , Yuwei Gong , Xingyi Li , Jinsong Liu . An ionic liquid-reinforced gelatin hydrogel with strong adhesion, antibacterial and anti-inflammatory properties for treating oral ulcers. Chinese Chemical Letters, 2025, 36(7): 110441-. doi: 10.1016/j.cclet.2024.110441
8. [8]
  Chenshi Lin , Chao Teng , Bingbing Li , Wei He . Anti-inflammatory drug-assisted microRNA gene therapy for effectively improving pulmonary hemodynamics. Chinese Chemical Letters, 2025, 36(7): 110450-. doi: 10.1016/j.cclet.2024.110450
9. [9]
  Hong-Jin Liao , Zhu Zhuo , Qing Li , Yoshihito Shiota , Jonathan P. Hill , Katsuhiko Ariga , Zi-Xiu Lu , Lu-Yao Liu , Zi-Ang Nan , Wei Wang , You-Gui Huang . A new class of crystalline X-ray induced photochromic materials assembled from anion-directed folding of a flexible cation. Chinese Chemical Letters, 2024, 35(8): 109052-. doi: 10.1016/j.cclet.2023.109052
10. [10]
  Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
11. [11]
  Xin Dong , Tianqi Chen , Jing Liang , Lei Wang , Huajie Wu , Zhijin Xu , Junhua Luo , Li-Na Li . Structure design of lead-free chiral-polar perovskites for sensitive self-powered X-ray detection. Chinese Journal of Structural Chemistry, 2024, 43(6): 100256-100256. doi: 10.1016/j.cjsc.2024.100256
12. [12]
  Xiaoyao Ma , Jinling Zhang , Ge Fang , He Gao , Jie Gao , Li Fu , Yuanyuan Hou , Gang Bai . Förster resonance energy transfer reveals phillygenin and swertiamarin concurrently target AKT on different binding domains to increase the anti-inflammatory effect. Chinese Chemical Letters, 2024, 35(5): 108823-. doi: 10.1016/j.cclet.2023.108823
13. [13]
  Wenjia Wang , Xingyue He , Xiaojie Wang , Tiantian Zhao , Osamu Muraoka , Genzoh Tanabe , Weijia Xie , Tianjiao Zhou , Lei Xing , Qingri Jin , Hulin Jiang . Glutathione-depleted cyclodextrin pseudo-polyrotaxane nanoparticles for anti-inflammatory oxaliplatin (Ⅳ) prodrug delivery and enhanced colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108656-. doi: 10.1016/j.cclet.2023.108656
14. [14]
  Xiongbo Song , Jinwen Xiao , Juan Wu , Li Sun , Long Chen . Decellularized amniotic membrane promotes the anti-inflammatory response of macrophages via PI3K/AKT/HIF-1α pathway. Chinese Chemical Letters, 2025, 36(1): 109844-. doi: 10.1016/j.cclet.2024.109844
15. [15]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
16. [16]
  Huijuan Zhang , Chenglin Liang , Xinyi Ding , Meng Zhang , Siyu Lu , Lin Hou . Manganese-based nano-delivery system for sensitized anti-tumor immunotherapy via combined autophagy inhibition. Chinese Chemical Letters, 2025, 36(7): 110525-. doi: 10.1016/j.cclet.2024.110525
17. [17]
  Zhexin Chen , Yuqing Shi , Fang Zhong , Kai Zhang , Furong Zhang , Shenghong Xie , Zhongbin Cheng , Qian Zhou , Yi-You Huang , Hai-Bin Luo . Discovery of amentoflavone as a natural PDE4 inhibitor with anti-fibrotic effects. Chinese Chemical Letters, 2025, 36(4): 109956-. doi: 10.1016/j.cclet.2024.109956
18. [18]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
19. [19]
  Xiaoning Li , Quanyu Shi , Meng Li , Ningxin Song , Yumeng Xiao , Huining Xiao , Tony D. James , Lei Feng . Functionalization of cellulose carbon dots with different elements (N, B and S) for mercury ion detection and anti-counterfeit applications. Chinese Chemical Letters, 2024, 35(7): 109021-. doi: 10.1016/j.cclet.2023.109021
20. [20]
  Xue-Jiao Wang , Jun-Li Xin , Hong Xiang , Ze-Yu Zhao , Yu-Hang He , Haibo Wang , Guangyao Mei , Yi-Cheng Mao , Juan Xiong , Jin-Feng Hu . Holotrichones A and B, potent anti-leukemic lindenane-type sesquiterpene trimers with unprecedented complex carbon skeletons from a rare Chloranthus species. Chinese Chemical Letters, 2024, 35(12): 109682-. doi: 10.1016/j.cclet.2024.109682

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(75)
HTML views(0)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142