Synthesis and biological evaluation of moscatilin analogs as anti-inflammatory agents

GUAN Li; WANG Chunyang; ZHAO Huiru; LI Weize; FENG Feng

doi:10.11665/j.issn.1000-5048.20210205

Journal of China Pharmaceutical University > 2021 > 52(2): 171-176. > DOI: 10.11665/j.issn.1000-5048.20210205

GUAN Li, WANG Chunyang, ZHAO Huiru, LI Weize, FENG Feng. Synthesis and biological evaluation of moscatilin analogs as anti-inflammatory agents[J]. Journal of China Pharmaceutical University, 2021, 52(2): 171-176. DOI: 10.11665/j.issn.1000-5048.20210205

Citation:

PDF (579 KB)

Synthesis and biological evaluation of moscatilin analogs as anti-inflammatory agents

1.
College of Pharmacy, Xi'an Medical University, Xi'an 710021
2.
School of Clinical Medicine, Xi'an Medical University, Xi'an 710021
3.
Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 211198, China

Funds: This study was supported by the Special Scientific Research Project of Shaanxi Provincial Department of Education (No. 20JK0895)

More Information

Received Date: September 13, 2020
Revised Date: March 03, 2021

Graphical Abstract

Abstract

Abstract

Using syringaldehyde as raw material, the phosphine ylide intermediate was efficiently synthesized through acetylated hydroxyl protection, aldehyde group reduction, chlorination and reaction with triphenylphosphine. On this basis, moscatilin (MST) and its 12 analogs (MST-1-MST-12) were synthesized by wittig reaction, deacetylation and double bond reduction. All the structures were confirmed by ¹H NMR, ¹³C NMR and ESI-MS. Bacterial lipopolysaccharide-induced mouse macrophage RAW264.7 inflammation model was used to conduct preliminary anti-inflammatory activity tests in vitro for the target compounds. Results showed that all compounds could inhibit the production of inflammatory factor NO, and that MST-5 exhibited the strongest anti-inflammatory activity (IC₅₀= 0.428 μmol/L).Further exploration is expected for the study of the anti-inflammatory mechanism of MST-5.
- moscatilin,
- bibenzyl,
- synthesis,
- anti-inflammatory activity

FullText(HTML)

References (13)

References

[1]	. Cell， 2003， 112（5）： 645-657.
[2]	Lu YC， Yeh WC， Ohashi PS. LPS/TLR4 signal transduction pathway［J］. Cytokine， 2008， 42（2）： 145-151.
[3]	Guan L， Hao YF， Chen L， et al. Synthesis and evaluation of neuroprotective 4-O-substituted chrysotoxine derivatives as potential multifunctional agents for the treatment of Alzheimer''s disease［J］. RSC Adv， 2016， 6（27）： 22827-22838.
[4]	Ho CK， Chen CC. Moscatilin from the orchid Dendrobrium loddigesii is a potential anticancer agent［J］. Cancer Invest， 2003， 21（5）： 729-736.
[5]	Tsai AC， Pan SL， Liao CH， et al. Moscatilin， a bibenzyl derivative from the India orchid Dendrobrium loddigesii， suppresses tumor angiogenesis and growth in vitro and in vivo［J］. Cancer Lett， 2010， 292（2）： 163-170.
[6]	Chen CA， Chen CC， Shen CC， et al. Moscatilin induces apoptosis and mitotic catastrophe in human esophageal cancer cells［J］. J Med Food， 2013， 16（10）： 869-877.
[7]	Zhang L， Fang Y， Xu XF， et al. Moscatilin induces apoptosis of pancreatic cancer cells via reactive oxygen species and the JNK/SAPK pathway［J］. Mol Med Rep， 2017， 15（3）： 1195-1203.
[8]	Kowitdamrong A， Chanvorachote P， Sritularak B， et al. Moscatilin inhibits lung cancer cell motility and invasion via suppression of endogenous reactive oxygen species［J］. Biomed Res Int， 2013， 2013， 765894.
[9]	Pai HC， Chang LH， Peng CY， et al. Moscatilin inhibits migration and metastasis of human breast cancer MDA-MB-231 cells through inhibition of Akt and Twist signaling pathway［J］. J Mol Med （Berl）， 2013， 91（3）： 347-356.
[10]	Guan L， Zhou JT， Lin QH， et al. Design， synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives［J］. Bioorg Med Chem， 2019， 27（12）： 2657-2665.
[11]	Miyazawa M， Shimamura H， Nakamura S， et al. Moscatilin from Dendrobium nobile， a naturally occurring bibenzyl compound with potential antimutagenic activity［J］. J Agric Food Chem， 1999， 47（5）： 2163-2167.
[12]	Liu YN， Pan SL， Peng CY， et al. Moscatilin repressed lipopolysaccharide-induced HIF-1α accumulation and NF-κB activation in murine RAW264.7 cells［J］. Shock， 2010， 33（1）： 70-75.
[13]	Tang YL， Zhang X， Yang XB， et al. Synthesis and preliminary anti-inflammatory activities of novel thienylchalcone derivatives ［J］. Chin J Syn Chem （合成化学）， 2020， 28（1）： 36 -40.

[1]	ZHAO Xiujuan, YANG Hengli, WU Jinye, ZHENG Xiaoqi, ZHANG Yaoping, LIN Yuping, HU Chunyan. Synthesis and anti-inflammatory activity of three series of coumarin-based derivatives[J]. Journal of China Pharmaceutical University, 2025, 56(1): 40-48. DOI: 10.11665/j.issn.1000-5048.2024072101
[2]	ZHU Hong, WEI Xiaopeng, JIN Meihua, QIN Nan. Synthesis and inhibition of NO production activities of 1, 6-O, O-diacylbritannilactone derivatives[J]. Journal of China Pharmaceutical University, 2017, 48(4): 440-444. DOI: 10.11665/j.issn.1000-5048.20170408
[3]	MOU Yi, CHEN Tong, HUANG Zhangjian, LAI Yisheng, PENG Sixun, JI Hui, ZHANG Yihua. Design, synthesis and anti-inflammatory evaluation of CDDO-Me ester prodrugs[J]. Journal of China Pharmaceutical University, 2016, 47(6): 661-665. DOI: 10.11665/j.issn.1000-5048.20160605
[4]	XU Guijun, LI Zhijun, WANG Qi, TAN Jiejun, SHI Guoshan, QI Wei, LI Di, WANG Youpeng. Isolation and identification of anti-inflammatory constituents from Houttuynia cordata[J]. Journal of China Pharmaceutical University, 2016, 47(3): 294-298. DOI: 10.11665/j.issn.1000-5048.20160308
[5]	WU Mingming, FANG Lei, GOU Shaohua, CHEN Li. 以2-甲基-2-取代苯氧基丙酸为离去基团的铂(Ⅱ)配合物的合成、表征及细胞毒活性[J]. Journal of China Pharmaceutical University, 2013, 44(4): 303-306. DOI: 10.11665/j.issn.1000-5048.20130403
[6]	HUANG Wen-xing, LAI Yi-sheng, ZHANG Yi-hua, WANG Zhen-guo, ZHANG Zhi-hao, MA Lin, JI Hui. Synthesis and anti-inflammatory activity of p-(sulfamyl)benzylidene-linked heterocyclic ketone derivatives[J]. Journal of China Pharmaceutical University, 2009, 40(6): 497-502.
[7]	AO Gui-zhen, ZHENG Li-ling, XU Guang-lin, LI Jing. Synthesis and anti-inflammatory activity of α-aryl-3，5-dimethoxyphenylpropenamides[J]. Journal of China Pharmaceutical University, 2009, 40(4): 302-305.
[8]	Synthesis and anti-inflammatory activities of aryl alkyl acid NSAIDs tetraacetylated glucoside derivatives[J]. Journal of China Pharmaceutical University, 2009, 40(1): 26-30.
[9]	Synthesis and anti-inflammatory activities of imidazo[1,2-a] pyrimidine derivatives[J]. Journal of China Pharmaceutical University, 2009, 40(1): 16-20.
[10]	Synthesis and Anti-inflammatory Activity of Nitric Oxidedonating α-Substituted p-(Methanesulfonyl)phenylpropenoic Acid Esters[J]. Journal of China Pharmaceutical University, 2004, (3): 6-10.

Cited By

Cited by

Periodical cited type(3)

1.	王苗苗，秦嘉泽，郭佳琪，于天成. 杓唇石斛开花特性与繁育系统研究. 浙江农业学报. 2025(01): 103-114 .
2.	关丽，赵惠茹，高璐，唐潇潇，李伟泽，赵宁，冯锋. 4-羟基-3, 5, 2′-三甲氧基联苄的合成及抑制血管新生活性研究. 化学与生物工程. 2022(10): 16-19 .
3.	刘鹏飞，范蓓，刘湘丹，杨洋，卢聪，佟立涛，孙晶，王凤忠. 铁皮石斛枫斗加工前后差异成分比较. 核农学报. 2022(12): 2412-2418 .

Other cited types(1)

Get Citation

PDF

XML

Article views (391) PDF downloads (604) Cited by(4)

Turn off MathJax

Article Contents

Abstract

References

Synthesis and biological evaluation of moscatilin analogs as anti-inflammatory agents

Abstract

References

Related Articles

Cited by

Periodical cited type(3)

Other cited types(1)

Catalog

Synthesis and biological evaluation of moscatilin analogs as anti-inflammatory agents

Abstract

References

Related Articles

Cited by

Periodical cited type(3)

Other cited types(1)

Catalog

Export File

Citation

Format

Content