Citation: Jia Xinyu, Wu Yongmei, Lei Chun, Yu Yanyan, Li Jianqi, Li Jingya, Hou Aijun. Hyperinoids A and B, two polycyclic meroterpenoids from Hypericum patulum[J]. Chinese Chemical Letters, ;2020, 31(5): 1263-1266. doi: 10.1016/j.cclet.2019.10.014 shu

Hyperinoids A and B, two polycyclic meroterpenoids from Hypericum patulum

Jia Xinyu ^a,c ,
Wu Yongmei ^b ,
Lei Chun ^a ,
Yu Yanyan ^b ,
Li Jianqi ^c,*, ,
Li Jingya ^b,*, ,
Hou Aijun ^a,*,

a.
School of Pharmacy, State Key Laboratory of Medical Neurobiology, Fudan University, Shanghai 201203, China
b.
National Center for Drug Screening, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
c.
Shanghai Institute of Pharmaceutical Industry, Shanghai 201203, China

lijianqb@126.com

jyli@simm.ac.cn

ajhou@shmu.edu.cn

Received Date: 21 August 2019
Revised Date: 13 October 2019
Accepted Date: 14 October 2019
Available Online: 30 October 2019

Figures(7)

Hyperinoids A (1) and B (2), two prenylated acylphloroglucinol related meroterpenoids, were isolated from Hypericum patulum. Compound 1 incorporates an unprecedented 11, 12-dioxatetracyclo[5.4.3.0^{1, 7}.0^{4, 14}]tetradecane system, while 2 possesses a unique 10, 11-dioxatetracyclo[5.3.3.0^{1, 7}.0^{4, 13}] tridecane system. Their structures were established by spectroscopic analysis and X-ray crystallographic data. Compounds 1 and 2 were identified as potent NF-κB inhibitors and suppressed the LPS-induced inflammatory responses in RAW 246.7 macrophages and primary mouse BMDM cells
- Meroterpenoids,
- Hyperinoids A and B,
- Anti-inflammation,
- Hypericum patulum,
- Guttiferae
1. [1]
  X. Li, N.K.B. Robson, Flora of China, Vol. 13, Science Press, Beijing, 2007, pp. 2-35.
2. [2]
  State Administration of Traditional Chinese Medicine of the People's Republic of China, Chinese Materia Medica, Vol. 9, Shanghai Scientific and Technical Publishers, Shanghai, 1999, pp. 594-608.
3. [3]
  X.W. Yang, R.B. Grossman, G. Xu, Chem. Rev. 118(2018) 3508-3558. doi: 10.1021/acs.chemrev.7b00551
4. [4]
  H. Bridi, G.C. Meirelles, G.L. von Poser, Phytochemistry 155(2018) 203-232. doi: 10.1016/j.phytochem.2018.08.002
5. [5]
  Y.L. Hu, K. Hu, L.M. Kong, et al., Org. Lett. 21(2019) 1007-1010. doi: 10.1021/acs.orglett.8b04022
6. [6]
  X.T. Yan, Z. An, Y. Huangfu, et al., Phytochemistry 159(2019) 65-74. doi: 10.1016/j.phytochem.2018.12.011
7. [7]
  N. Tanaka, Y. Yano, Y. Tatano, et al., Org. Lett. 18(2016) 5360-5363. doi: 10.1021/acs.orglett.6b02725
8. [8]
  Y.Y. Liu, Z. Ao, G.M. Xue, et al., Org. Lett. 20(2018) 7953-7956. doi: 10.1021/acs.orglett.8b03523
9. [9]
  Z.N. Wu, Q.W. Niu, Y.B. Zhang, et al., RSC Adv. 9(2019) 7961-7966. doi: 10.1039/C9RA00277D
10. [10]
  H.B. Liao, C. Lei, L.X. Gao, et al., Org. Lett. 17(2015) 5040-5043. doi: 10.1021/acs.orglett.5b02515
11. [11]
  H.B. Liao, G.H. Huang, M.H. Yu, et al., J. Org. Chem. 82(2017) 1632-1637. doi: 10.1021/acs.joc.6b02800
12. [12]
  G.H. Huang, Z. Hu, C. Lei, et al., J. Nat. Prod. 81(2018) 1810-1818. doi: 10.1021/acs.jnatprod.8b00273
13. [13]
  R.G. Baker, M.S. Hayden, S. Ghosh, Cell Metab. 13(2011) 11-22.. doi: 10.1016/j.cmet.2010.12.008
14. [14]
  J.C. McNelis, J.M. Olefsky, Immunity 41(2014) 36-48. doi: 10.1016/j.immuni.2014.05.010
1. [1]
  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
2. [2]
  Xiaoliu Liang , Chunliu Huang , Hui Liu , Hu Chen , Jiabao Shou , Hongwei Cheng , Gang Liu . Natural hydrogel dressings in wound care: Design, advances, and perspectives. Chinese Chemical Letters, 2024, 35(10): 109442-. doi: 10.1016/j.cclet.2023.109442
3. [3]
  Chuan Li , Yangyang Han , Yanan Zhai , Ke Li , Xingzhong Liu , Zhuan Zhang , Cai Jia , Yongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019
4. [4]
  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
5. [5]
  Wei-Yu Zhou , Zi-Han Xi , Ning-Ning Du , Li Ye , Ming-Hao Jiang , Jin-Le Hao , Bin Lin , Guo-Dong Yao , Xiao-Xiao Huang , Shao-Jiang Song . Rapid discovery of two unprecedented meroterpenoids from Daphne altaica Pall. using molecular networking integrated with MolNetEnhancer and Network Annotation Propagation. Chinese Chemical Letters, 2024, 35(8): 109030-. doi: 10.1016/j.cclet.2023.109030
6. [6]
  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
7. [7]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
8. [8]
  Tengfei Xuan , Xinyu Zhang , Wei Han , Yidong Huang , Weiwu Ren . Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B. Chinese Chemical Letters, 2025, 36(2): 109816-. doi: 10.1016/j.cclet.2024.109816
9. [9]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
10. [10]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
11. [11]
  Yu Yan , Jiawei Song , Dongdong Liu , Zihan Liu , Jialing Cheng , Zhiyang Chen , Yanfang Yang , Weizhe Jiang , Hongliang Wang , Jun Ye , Yuling Liu . Simple and versatile in situ thermo-sensitive hydrogel for rectal administration of SZ-A to alleviate inflammation and repair mucosal barrier in ulcerative colitis. Chinese Chemical Letters, 2024, 35(6): 109736-. doi: 10.1016/j.cclet.2024.109736
12. [12]
  Haiyang Gu , Xiang Xu . Multicolor hybrid metal halides and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(9): 100352-100352. doi: 10.1016/j.cjsc.2024.100352
13. [13]
  Jiao CHEN , Yi LI , Yi XIE , Dandan DIAO , Qiang XIAO . Vapor-phase transport of MFI nanosheets for the fabrication of ultrathin b-axis oriented zeolite membranes. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 507-514. doi: 10.11862/CJIC.20230403
14. [14]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
15. [15]
  Jia-Li Xie , Tian-Jin Xie , Yu-Jie Luo , Kai Mao , Cheng-Zhi Huang , Yuan-Fang Li , Shu-Jun Zhen . Octopus-like DNA nanostructure coupled with graphene oxide enhanced fluorescence anisotropy for hepatitis B virus DNA detection. Chinese Chemical Letters, 2024, 35(6): 109137-. doi: 10.1016/j.cclet.2023.109137
16. [16]
  Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
17. [17]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
18. [18]
  Yuan CONG , Yunhao WANG , Wanping LI , Zhicheng ZHANG , Shuo LIU , Huiyuan GUO , Hongyu YUAN , Zhiping ZHOU . Construction and photocatalytic properties toward rhodamine B of CdS/Fe₃O₄ heterojunction. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2241-2249. doi: 10.11862/CJIC.20240219
19. [19]
  Xinyu Tian , Jiaxiang Guo , Zeyi Li , Shihou Sheng , Tianyu Zhang , Xianfei Li , Chuandong Dou . Control over electronic structures of organic diradicaloids via precise B/O-heterocycle fusion. Chinese Chemical Letters, 2025, 36(1): 110174-. doi: 10.1016/j.cclet.2024.110174
20. [20]
  Wenhao Yan , Shuaiya Xue , Xuerui Zhao , Wei Zhang , Jian Li . Hexagonal boron nitride based slippery liquid infused porous surface with anti-corrosion, anti-contaminant and anti-icing properties for protecting magnesium alloy. Chinese Chemical Letters, 2024, 35(4): 109224-. doi: 10.1016/j.cclet.2023.109224

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(716)
HTML views(43)

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