(±)-Bicoryanhunine A, dimeric benzylisoquinoline alkaloid atropo-enantiomers from Corydalis yanhusuo

Biao Bing Xiao; Gui Yang Xia; Ling Yan Wang; Bo Lin Qiu; Huan Xia; Wan Chao Zhong; Gui Hua Tian; Sheng Lin

doi:10.1016/j.tetlet.2020.151890

(±)-Bicoryanhunine A, dimeric benzylisoquinoline alkaloid atropo-enantiomers from Corydalis yanhusuo

Biao Bing Xiao, Gui Yang Xia, Ling Yan Wang, Bo Lin Qiu, Huan Xia, Wan Chao Zhong, Gui Hua Tian^*, Sheng Lin

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

Bicoryanhunine A (1), isolated from the dried tubers of Corydalis yanhusuo, is the first novel dimeric benzylisoquinoline alkaloid with a 4,7′-coupled biaryl axis. This novel C-4-C-7′ linkage lead to the highest steric hindrance at the biaryl axis, giving rise to a pair of atropo-enantiomers that are well resolved into the anticipated enantiomers, (+)-bicoryanhunine A (1) and (−)-bicoryanhunine A (1), with the help of chiral-phase HPLC. Their structures including the axial configurations were elucidated by spectroscopic methods and experimental and calculated ECD investigations. Bicoryanhunine A (1) was a moderate PD-1/PD-L1 interaction inhibitor with an IC₅₀ value of 14.3 ± 0.67 μM.

Original language	English
Article number	151890
Journal	Tetrahedron Letters
Volume	61
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2020.151890
Publication status	Published - 21 May 2020
Externally published	Yes

Keywords

Bicoryanhunine A
Corydalis yanhusuo
Dimeric benzylisoquinoline alkaloid
PD-1/PD-L1 interaction inhibitor

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10.1016/j.tetlet.2020.151890

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title = "(±)-Bicoryanhunine A, dimeric benzylisoquinoline alkaloid atropo-enantiomers from Corydalis yanhusuo",

abstract = "Bicoryanhunine A (1), isolated from the dried tubers of Corydalis yanhusuo, is the first novel dimeric benzylisoquinoline alkaloid with a 4,7′-coupled biaryl axis. This novel C-4-C-7′ linkage lead to the highest steric hindrance at the biaryl axis, giving rise to a pair of atropo-enantiomers that are well resolved into the anticipated enantiomers, (+)-bicoryanhunine A (1) and (−)-bicoryanhunine A (1), with the help of chiral-phase HPLC. Their structures including the axial configurations were elucidated by spectroscopic methods and experimental and calculated ECD investigations. Bicoryanhunine A (1) was a moderate PD-1/PD-L1 interaction inhibitor with an IC50 value of 14.3 ± 0.67 μM.",

keywords = "Bicoryanhunine A, Corydalis yanhusuo, Dimeric benzylisoquinoline alkaloid, PD-1/PD-L1 interaction inhibitor",

author = "Xiao, {Biao Bing} and Xia, {Gui Yang} and Wang, {Ling Yan} and Qiu, {Bo Lin} and Huan Xia and Zhong, {Wan Chao} and Tian, {Gui Hua} and Sheng Lin",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

year = "2020",

month = may,

day = "21",

doi = "10.1016/j.tetlet.2020.151890",

language = "English",

volume = "61",

journal = "Tetrahedron Letters",

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T1 - (±)-Bicoryanhunine A, dimeric benzylisoquinoline alkaloid atropo-enantiomers from Corydalis yanhusuo

AU - Xiao, Biao Bing

AU - Xia, Gui Yang

AU - Wang, Ling Yan

AU - Qiu, Bo Lin

AU - Xia, Huan

AU - Zhong, Wan Chao

AU - Tian, Gui Hua

AU - Lin, Sheng

PY - 2020/5/21

Y1 - 2020/5/21

N2 - Bicoryanhunine A (1), isolated from the dried tubers of Corydalis yanhusuo, is the first novel dimeric benzylisoquinoline alkaloid with a 4,7′-coupled biaryl axis. This novel C-4-C-7′ linkage lead to the highest steric hindrance at the biaryl axis, giving rise to a pair of atropo-enantiomers that are well resolved into the anticipated enantiomers, (+)-bicoryanhunine A (1) and (−)-bicoryanhunine A (1), with the help of chiral-phase HPLC. Their structures including the axial configurations were elucidated by spectroscopic methods and experimental and calculated ECD investigations. Bicoryanhunine A (1) was a moderate PD-1/PD-L1 interaction inhibitor with an IC50 value of 14.3 ± 0.67 μM.

AB - Bicoryanhunine A (1), isolated from the dried tubers of Corydalis yanhusuo, is the first novel dimeric benzylisoquinoline alkaloid with a 4,7′-coupled biaryl axis. This novel C-4-C-7′ linkage lead to the highest steric hindrance at the biaryl axis, giving rise to a pair of atropo-enantiomers that are well resolved into the anticipated enantiomers, (+)-bicoryanhunine A (1) and (−)-bicoryanhunine A (1), with the help of chiral-phase HPLC. Their structures including the axial configurations were elucidated by spectroscopic methods and experimental and calculated ECD investigations. Bicoryanhunine A (1) was a moderate PD-1/PD-L1 interaction inhibitor with an IC50 value of 14.3 ± 0.67 μM.

KW - Bicoryanhunine A

KW - Corydalis yanhusuo

KW - Dimeric benzylisoquinoline alkaloid

KW - PD-1/PD-L1 interaction inhibitor

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U2 - 10.1016/j.tetlet.2020.151890

DO - 10.1016/j.tetlet.2020.151890

M3 - Article

AN - SCOPUS:85083184550

SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

M1 - 151890

ER -

(±)-Bicoryanhunine A, dimeric benzylisoquinoline alkaloid atropo-enantiomers from Corydalis yanhusuo

Abstract

Keywords

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