Citation: Yunshao Xu, Tian Zhang, Lu Feng, Zheling Feng, Qingwen Zhang, Yang Ye, Lishe Gan, Ligen Lin. Biscaesalmins A and B from Caesalpinia minax, highly oxidized dimeric cassane diterpenoids as interleukin-1β inhibitors[J]. Chinese Chemical Letters, ;2021, 32(4): 1475-1479. doi: 10.1016/j.cclet.2020.09.048 shu

Biscaesalmins A and B from Caesalpinia minax, highly oxidized dimeric cassane diterpenoids as interleukin-1β inhibitors

Yunshao Xu ^{a, 1} ,
Tian Zhang ^{a, 1} ,
Lu Feng ^b ,
Zheling Feng ^a ,
Qingwen Zhang ^a ,
Yang Ye ^{b, c} ,
Lishe Gan ^{d, *,} ,
Ligen Lin ^{a, *,}

a.
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Avenida da Universidade, Taipa, Macau 999078, China
b.
State Key Laboratory of Drug Research, & Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
c.
School of Life Science and Technology, Shanghai Tech University, Shanghai 201203, China
d.
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, China

ganlishe@126.com

ligenl@um.edu.mo

Received Date: 17 July 2020
Revised Date: 1 September 2020
Accepted Date: 25 September 2020
Available Online: 28 September 2020

Figures(4)

To search naturally occurring interleukin-1β (IL-1β) inhibitors, biscaesalmins A (1) and B (2), two highly oxidized dimeric cassane diterpenoids with a newly formed alicyclic skeleton, have been isolated from the traditional Chinese medicine Kushilian (Caesalpinia minax). Their full structures were determined by comprehensive spectroscopic analysis and quantum chemical TD-DFT (time-dependent density functional theory) calculation. Biosynthetically, 1 and 2 were formed via an intermolecular [4+2] Diels-Alder cycloaddition of two monomers, affording an additional six-membered carbon ring linkage. Compounds 1 and 2 inhibited nitric oxide production on lipopolysaccharide-stimulated THP-1 macrophages, with IC₅₀ values being at 1.20±0.23 and 2.30±0.15 μmol/L, respectively. Furthermore, compound 1 inhibited NLRP3 (NOD-, LRR- and pyrin domain-containing protein 3) inflammasome-mediated IL-1β production and blocked the migration of macrophages towards adipocyte conditioned medium. Biscaesalmins A and B might be candidates for treating inflammation-related metabolic diseases.
- Caesalpinia minax,
- IL-1β,
- Dimeric cassane diterpenoids,
- NLRP3,
- TD-DFT
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