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]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  Chunlei Dai , Liying Wang , Xinru You , Yi Zhao , Zhong Cao , Jun Wu . Coffee-derived self-anti-inflammatory polymer as drug nanocarrier for enhanced rheumatoid arthritis treatment. Chinese Chemical Letters, 2025, 36(3): 109869-. doi: 10.1016/j.cclet.2024.109869
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  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
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]
  Hao-Fei Ni , Jia-He Lin , Gele Teri , Qiang-Qiang Jia , Pei-Zhi Huang , Hai-Feng Lu , Chang-Feng Wang , Zhi-Xu Zhang , Da-Wei Fu , Yi Zhang . B-site ion regulation strategy enables performance optimization and multifunctional integration of hybrid perovskite ferroelectrics. Chinese Chemical Letters, 2025, 36(3): 109690-. doi: 10.1016/j.cclet.2024.109690

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(769)
HTML views(33)

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