Citation: Guiyang Xia, Biaobing Xiao, Lingyan Wang, Huan Xia, Yuzhuo Wu, Yanan Wang, Hongcai Shang, Sheng Lin. (+)/(−)-Yanhusuosines A and B, two dimeric benzylisoquinoline-protoberberine alkaloid atropo-enantiomers featuring polycyclic skeletons from Corydalis yanhusuo[J]. Chinese Chemical Letters, ;2023, 34(7): 108073. doi: 10.1016/j.cclet.2022.108073 shu

(+)/(−)-Yanhusuosines A and B, two dimeric benzylisoquinoline-protoberberine alkaloid atropo-enantiomers featuring polycyclic skeletons from Corydalis yanhusuo

Guiyang Xia ^a ,
Biaobing Xiao ^b ,
Lingyan Wang ^a ,
Huan Xia ^a ,
Yuzhuo Wu ^a ,
Yanan Wang ^b ,
Hongcai Shang ^a ,
Sheng Lin ^{a, *,}

a.
Key Laboratory of Chinese Internal Medicine of Ministry of Education and Beijing, Dongzhimen Hospital, Beijing University of Chinese Medicine, Beijing 100700, China
b.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

lsznn@bucm.edu.cn

Received Date: 12 September 2022
Revised Date: 18 November 2022
Accepted Date: 12 December 2022
Available Online: 11 January 2023

Figures(5)

(+)/(−)-Yanhusuosines A (1) and B (2), two pairs of trace benzylisoquinoline-protoberberine atropo-enantiomeric homodimers featuring an unprecedented 6/7/6/6/6/6 hexacyclic skeleton, were isolated from the tubers of Corydalis yanhusuo. The structures of (+)/(−)-1 and (+)/(−)-2 were elucidated using spectroscopic and quantum-chemical calculation approaches. (+)/(−)-Yanhusuosines A (1) and B (2) represent a new class of alkaloid dimers biogenetically constructed by a molecule of benzylisoquinoline with a unit of protoberberine via an intermolecular [4 + 3] cycloaddition. Their plausible biosynthetic pathways are discussed, and compound 2 exerted moderate inhibitory activity of NO formation in LPS induced RAW264.7 macrophages.
- (+)/(−)-Yanhusuosine A,
- (+)/(−)-Yanhusuosine B,
- Bisbenzylisoquinoline alkaloids,
- Atropo-enantiomeric homodimers,
- Anti-inflammatory,
- Corydalis yanhusuo
1. [1]
  H. Guinaudeau, A.J. Freyer, M. Shamma, Nat. Prod. Rep. 3 (1986) 477–488. doi: 10.1039/np9860300477
2. [2]
  P.L. Schiff, J. Nat. Prod. 50 (1987) 529–599. doi: 10.1021/np50052a001
3. [3]
  P.L. Schiff, J. Nat. Prod. 54 (1991) 645–749. doi: 10.1021/np50075a001
4. [4]
  P.L. Schiff, J. Nat. Prod. 60 (1997) 934–953. doi: 10.1021/np9700174
5. [5]
  V.K. Nguyen, K.G.M. Kou, Org. Biomol. Chem. 19 (2021) 7535–7543. doi: 10.1039/D1OB00812A
6. [6]
  C. Weber, T. Opatz, Alkaloids Chem. Biol. 81 (2019) 1–114.
7. [7]
  J.Q. Qian, Acta Pharmacol. Sin. 23 (2002) 1086–1092.
8. [8]
  I. Galindo, U. Garaigorta, F. Lasala, et al., Antiviral Res. 186 (2021) 104990. doi: 10.1016/j.antiviral.2020.104990
9. [9]
  S. Zhang, W. Huang, L. Ren, et al., Cell Res. 32 (2022) 9–23. doi: 10.1038/s41422-021-00581-y
10. [10]
  L.Y. Wang, B.L. Qiu, H. Xia, et al., J. Nat. Prod. 83 (2020) 489–496. doi: 10.1021/acs.jnatprod.9b01155
11. [11]
  L. Alhassen, T. Dabbous, A. Ha, et al., Molecules 26 (2021) 7498. doi: 10.3390/molecules26247498
12. [12]
  B. Tian, M. Tian, S.M. Huang, Pharm. Biol. 58 (2020) 265–275. doi: 10.1080/13880209.2020.1741651
13. [13]
  J. Zhang, S. He, J. Wang, et al., Nat. Prod. Commun. 15 (2020) 1–19.
14. [14]
  D. Xu, H. Lin, Y. Tang, et al., Hortic. Res. 8 (2021) 16. doi: 10.1038/s41438-020-00450-6
15. [15]
  N. Cabedo, I. Berenguer, B. Figadere, et al., Curr. Med. Chem. 16 (2009) 2441–2467. doi: 10.2174/092986709788682100
16. [16]
  C.M. Sai, D.H. Li, C.M. Xue, et al., Org. Lett. 17 (2015) 4102–4105. doi: 10.1021/acs.orglett.5b02044
17. [17]
  G.Y. Xia, B.B. Xiao, L.Y. Wang, et al., Acta Pharm. Sin. 56 (2021) 553–556.
18. [18]
  B.B. Xiao, G.Y. Xia, L.Y. Wang, et al., Tetrahedron Lett. 61 (2020) 151890. doi: 10.1016/j.tetlet.2020.151890
19. [19]
  S. Fayez, J. Li, D. Feineis, et al., J. Nat. Prod. 82 (2019) 3033–3046. doi: 10.1021/acs.jnatprod.9b00589
20. [20]
  B.K. Lombe, T. Bruhn, D. Feineis, et al., Org. Lett. 19 (2017) 1342–1345. doi: 10.1021/acs.orglett.7b00209
21. [21]
  B.K. Lombe, T. Bruhn, D. Feineis, et al., Org. Lett. 19 (2017) 6740–6743. doi: 10.1021/acs.orglett.7b03473
22. [22]
  M. Xu, T. Bruhn, B. Hertlein, et al., Chemistry 16 (2010) 4206–4216. doi: 10.1002/chem.200903247
23. [23]
  G.J. Mei, W.L. Koay, C.Y. Guan, et al., Chem 8 (2022) 1855–1893. doi: 10.1016/j.chempr.2022.04.011
24. [24]
  J.E. Smyth, N.M. Butler, P.A. Keller, Nat. Prod. Rep. 32 (2015) 1562–1583. doi: 10.1039/C4NP00121D
25. [25]
  X.L. Min, X.L. Zhang, R. Shen, et al., Org. Chem. Front. 9 (2022) 2280–2292. doi: 10.1039/D1QO01699G
26. [26]
  B.K. Lombe, D. Feineis, G. Bringmann, Nat. Prod. Rep. 36 (2019) 1513–1545. doi: 10.1039/C9NP00024K
27. [27]
  Z. Yin, Y. He, P. Chiu, Chem. Soc. Rev. 47 (2018) 8881–8924. doi: 10.1039/C8CS00532J
28. [28]
  Z. Xu, Z. Li, F. Ren, et al., Plant J. 111 (2022) 217–230. doi: 10.1111/tpj.15788
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]
  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
3. [3]
  Ji Zhang , Tong Zhang , Qiao An , Peng Zhang , Cai-Yan Tian , Chun-Mao Yuan , Ping Yi , Zhan-Xing Hu , Xiao-Jiang Hao . Five quinolizidine alkaloids with anti-tobacco mosaic virus activities from two species of Sophora. Chinese Chemical Letters, 2024, 35(6): 108927-. doi: 10.1016/j.cclet.2023.108927
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]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  Feifei Wang , Hang Yao , Xinyue Wu , Yijian Tang , Yang Bai , Hui Chong , Huan Pang . Metal–organic framework and its composites modulate macrophage polarization in the treatment of inflammatory diseases. Chinese Chemical Letters, 2024, 35(5): 108821-. doi: 10.1016/j.cclet.2023.108821
16. [16]
  Jingting Wang , Yuanyuan Chen , Linlin Han , Shasha Xia , Xingyao Zhang , Peng Xue , Yuejun Kang , Jian Ming , Zhigang Xu . Microenvironment responsive pod-structured astaxanthin nanocarrier for ameliorating inflammatory bowel disease. Chinese Chemical Letters, 2024, 35(7): 109029-. doi: 10.1016/j.cclet.2023.109029
17. [17]
  Weijian Zhang , Xianyu Deng , Liying Wang , Jian Wang , Xiuting Guo , Lianggui Huang , Xinyi Wang , Jun Wu , Linjia Jiang . Poly(ferulic acid) nanocarrier enhances chemotherapy sensitivity of acute myeloid leukemia by selectively targeting inflammatory macrophages. Chinese Chemical Letters, 2024, 35(9): 109422-. doi: 10.1016/j.cclet.2023.109422
18. [18]
  Xiao Xiao , Biao Chen , Jia-Wei Li , Jun-Bo Zheng , Xu Wang , Hang Zhao , Fen-Er Chen . Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow. Chinese Chemical Letters, 2024, 35(7): 109280-. doi: 10.1016/j.cclet.2023.109280
19. [19]
  Luyan Shi , Ke Zhu , Yuting Yang , Qinrui Liang , Qimin Peng , Shuqing Zhou , Tayirjan Taylor Isimjan , Xiulin Yang . Phytic acid-derivative Co₂B-CoPO_x coralloidal structure with delicate boron vacancy for enhanced hydrogen generation from sodium borohydride. Chinese Chemical Letters, 2024, 35(4): 109222-. doi: 10.1016/j.cclet.2023.109222
20. [20]
  Guangchang Yang , Shenglong Yang , Jinlian Yu , Yishun Xie , Chunlei Tan , Feiyan Lai , Qianqian Jin , Hongqiang Wang , Xiaohui Zhang . Regulating local chemical environment in O3-type layered sodium oxides by dual-site Mg²⁺/B³⁺ substitution achieves durable and high-rate cathode. Chinese Chemical Letters, 2024, 35(9): 109722-. doi: 10.1016/j.cclet.2024.109722

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(409)
HTML views(19)

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