Diterpenoids with Rearranged 9(10→11)-abeo-10,12-Cyclojatrophane Skeleton and the First (15S)-Jatrophane from Euphorbia helioscopia: Structural Elucidation, Biomimetic Conversion, and Their Immunosuppressive Effects
Zhi Nan Xiang
1
,
Qi Lin Tong
1
,
Jun Cheng Su
2
,
Zhuo Fan Hu
1
,
Ning Zhao
3
,
Ru Feng Xia
1
,
Jia Le Wu
1
,
Chen Chen
1
,
Jiachun Chen
1
,
Luo Sheng Wan
1
Publication type: Journal Article
Publication date: 2021-12-29
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
34965138
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Two novel diterpenoids, one with a rearranged trans,trans-fused tricyclo[10.3.0.04,6]pentadecane framework (1) and the other with an unprecedented 15S configuration (2), were isolated from Euphorbia helioscopia. Their structures were elucidated by extensive analysis of HR-ESI-MS, NMR, quantum-chemical calculation, and X-ray crystallographic data. Biosynthetically, 1 has a unique "cyclopropane-shift-like" biogenesis involving an oxa-di-π-methane (ODPM) rearrangement, which inspired us to accomplish the biomimetic conversion of 3 to 1. Moreover, compound 1 displayed a potent immunosuppressive effect by inhibiting Kv1.3 voltage-gated channels.
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Total citations:
19
Citations from 2025:
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(15.79%)
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Xiang Z. N. et al. Diterpenoids with Rearranged 9(10→11)-abeo-10,12-Cyclojatrophane Skeleton and the First (15S)-Jatrophane from Euphorbia helioscopia: Structural Elucidation, Biomimetic Conversion, and Their Immunosuppressive Effects // Organic Letters. 2021. Vol. 24. No. 2. pp. 697-701.
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Xiang Z. N., Tong Q. L., Su J. C., Hu Z. F., Zhao N., Xia R. F., Wu J. L., Chen C., Chen J., Wan L. S. Diterpenoids with Rearranged 9(10→11)-abeo-10,12-Cyclojatrophane Skeleton and the First (15S)-Jatrophane from Euphorbia helioscopia: Structural Elucidation, Biomimetic Conversion, and Their Immunosuppressive Effects // Organic Letters. 2021. Vol. 24. No. 2. pp. 697-701.
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TY - JOUR
DO - 10.1021/acs.orglett.1c04145
UR - https://doi.org/10.1021/acs.orglett.1c04145
TI - Diterpenoids with Rearranged 9(10→11)-abeo-10,12-Cyclojatrophane Skeleton and the First (15S)-Jatrophane from Euphorbia helioscopia: Structural Elucidation, Biomimetic Conversion, and Their Immunosuppressive Effects
T2 - Organic Letters
AU - Xiang, Zhi Nan
AU - Tong, Qi Lin
AU - Su, Jun Cheng
AU - Hu, Zhuo Fan
AU - Zhao, Ning
AU - Xia, Ru Feng
AU - Wu, Jia Le
AU - Chen, Chen
AU - Chen, Jiachun
AU - Wan, Luo Sheng
PY - 2021
DA - 2021/12/29
PB - American Chemical Society (ACS)
SP - 697-701
IS - 2
VL - 24
PMID - 34965138
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2021_Xiang,
author = {Zhi Nan Xiang and Qi Lin Tong and Jun Cheng Su and Zhuo Fan Hu and Ning Zhao and Ru Feng Xia and Jia Le Wu and Chen Chen and Jiachun Chen and Luo Sheng Wan},
title = {Diterpenoids with Rearranged 9(10→11)-abeo-10,12-Cyclojatrophane Skeleton and the First (15S)-Jatrophane from Euphorbia helioscopia: Structural Elucidation, Biomimetic Conversion, and Their Immunosuppressive Effects},
journal = {Organic Letters},
year = {2021},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.orglett.1c04145},
number = {2},
pages = {697--701},
doi = {10.1021/acs.orglett.1c04145}
}
Cite this
MLA
Copy
Xiang, Zhi Nan, et al. “Diterpenoids with Rearranged 9(10→11)-abeo-10,12-Cyclojatrophane Skeleton and the First (15S)-Jatrophane from Euphorbia helioscopia: Structural Elucidation, Biomimetic Conversion, and Their Immunosuppressive Effects.” Organic Letters, vol. 24, no. 2, Dec. 2021, pp. 697-701. https://doi.org/10.1021/acs.orglett.1c04145.