| Item type |
学術雑誌論文 / Journal Article(1) |
| 公開日 |
2023-11-21 |
| タイトル |
|
|
タイトル |
Isolation, Synthesis, and Structure-Activity Relationship Study on Daphnane and Tigliane Diterpenes as HIV Latency-Reversing Agents |
|
言語 |
en |
| 言語 |
|
|
言語 |
eng |
| 資源タイプ |
|
|
資源タイプ |
journal article |
| 著者 |
Ahmed, H. H. El-Desoky
Keisuke, Eguchi
Naoki, Kishimoto
Toshifumi, Asano
Hikaru, Kato
Yuki, Hitora
Shunsuke, Kotani
Teruya, Nakamura
Soken, Tsuchiya
Teppei, Kawahara
Masato, Watanabe
Mikiyo, Wada
Makoto, Nakajima
Takashi, Watanabe
Shogo, Misumi
塚本, 佐知子
|
| 内容記述 |
|
|
内容記述 |
Three new diterpenes, stellejasmins A (1) and B (2) and 12-O-benzoylphorbol-13-heptanoate (3), were isolated from the roots of Stellera chamaejasme L. The structures of 1–3 were elucidated by extensive NMR and mass spectroscopic analyses. Compounds 1 and 2 are the first derivatives containing a hydroxy group at C-2 in the family of daphnane and tigliane diterpenes. The presence of a chlorine atom in 1 is unique in the plant metabolite. Compound 3 has an odd-number acyl group, which is biosynthetically notable. Human immunodeficiency virus (HIV) LTR-driven transcription activity was tested with 1–3 and 17 known diterpenes isolated from S. chamaejasme L. and Wikstroemia retusa A.Gray. Among these, gnidimacrin (4), stelleralide A (5), and wikstroelide A (20) were highly potent, with EC50 values of 0.14, 0.33, and 0.39 nM, respectively. The structure–activity relationship (SAR) was investigated using 20 natural and eight synthetic diterpenes. This is the first SAR study on natural daphnane and tigliane diterpenes. |
| 書誌情報 |
en : Journal of Medicinal Chemistry
巻 65,
号 4,
p. 3460-3472,
発行年 2022-02-24
|
| ISSN |
|
|
収録物識別子 |
0022-2623 |
| DOI |
|
|
関連タイプ |
isVersionOf |
|
|
関連識別子 |
https://doi.org/10.1021/acs.jmedchem.1c01973 |
| 権利 |
|
|
権利情報 |
(C)2022 American Chemical Society |
| 権利 |
|
|
権利情報 |
This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in [Journal of Medicinal Chemistry], copyright (C)2022 American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.jmedchem.1c01973 |
| 著者版フラグ |
|
|
出版タイプ |
AM |
acs_jmedchem_1c01973.pdf (3.1 MB)
