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
Тип публикации: Journal Article
Дата публикации: 2021-12-29
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 1.007
CiteScore: 8.7
Impact factor: 5
ISSN: 15237060, 15237052
PubMed ID:
34965138
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
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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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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@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}
}
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MLA
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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.
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