Effect and mechanism of wedelolactone as antioxidant-coumestan on OH-treated mesenchymal stem cells

Published on Jan 1, 2020in Arabian Journal of Chemistry4.762
· DOI :10.1016/J.ARABJC.2017.03.008
Xican Li19
Estimated H-index: 19
(Guangzhou University of Chinese Medicine),
Tingting Wang13
Estimated H-index: 13
(Guangzhou University of Chinese Medicine)
+ 5 AuthorsDongfeng Chen22
Estimated H-index: 22
(Guangzhou University of Chinese Medicine)
Sources
Abstract
Abstract The antioxidant properties of coumestans have been investigated previously using inappropriate methods, which has resulted in misleading and inaccurate mechanisms being reported to account for their antioxidant behavior. In this study, the phenolic coumestan wedelolactone increased the viability of OH -treated mesenchymal stem cells (MSCs) in a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl assay. Mechanistic analysis in vitro suggested that wedelolactone could scavenge various radicals, including OH , O 2 - , 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) and 1,1-diphenyl-2-picrylhydrazyl ( DPPH ) radicals, as well as reducing Cu 2+ and chelating Fe 2+ . Configuration analysis based on a ball and stick model indicated that the 3′,4′-catechol moiety of wedelolactone was acting as an Fe 2+ -chelating site. The main product of the reaction between wedelolactone and DPPH was analyzed by ultra-performance liquid chromatography electrospray ionization quadrupole time-of-flight tandem mass spectrometry, which gave a mass ion with an m/z value of 709. This peak yielded several fragments with m/z values of 663, 543, 501 and 483. Quantitative evaluation revealed that the antioxidant activity of wedelolactone was 1.62 times higher than that of Trolox. Based on these results, we concluded that (i) wedelolactone can efficiently protect MSCs against OH -induced damage and that this protective effect provides preliminary evidence for the application of wedelolactone in transplantation of MSCs (especially for osteoporosis); (ii) the main antioxidant mechanism of wedelolactone involves direct radical-scavenging via a single electron transfer (SET) → radical adduct formation (RAF) pathway, whereas the Fe 2+ -chelating activity of wedelolactone represents a minor pathway; and (iii) the direct radical-scavenging and Fe 2+ -chelating pathways can both be attributed to the catechol moiety rather than the coumestan skeleton.
📖 Papers frequently viewed together
21 Citations
37 Citations
25 Citations
References35
Newest
#1Gulcin Gacar (Kocaeli University)H-Index: 12
#2Sema Yusufoğlu (Kocaeli University)H-Index: 1
Last. Tijen Utkan (Kocaeli University)H-Index: 18
view all 5 authors...
2 CitationsSource
#1Yuchen ZhangH-Index: 5
#2Wenjing Zhai (Academy of Medical Sciences, United Kingdom)H-Index: 1
Last. Aimin Meng (Peking Union Medical College)H-Index: 22
view all 13 authors...
Objective Using a mouse model, Iron Overload (IO) induced bone marrow microenvironment injury was investigated, focusing on the involvement of reactive oxygen species (ROS). Methods Mice were intraperitoneally injected with iron dextran (12.5, 25, or 50mg) every three days for two, four, and six week durations. Deferasirox(DFX)125mg/ml and N-acetyl-L-cysteine (NAC) 40mM were co-administered. Then, bone marrow derived mesenchymal stem cells (BM-MSCs) were isolated and assessed for proliferation a...
51 CitationsSource
#1Chia-Jung Hsieh (KMU: Kaohsiung Medical University)H-Index: 4
#2Po-Lin Kuo (KMU: Kaohsiung Medical University)H-Index: 33
Last. Ya-Ling Hsu (KMU: Kaohsiung Medical University)H-Index: 27
view all 9 authors...
The bone is the most common metastatic site of breast cancer. Bone metastasis causes pain, pathologic frac- tures, and severely reduces the quality of life. Breast cancer causes osteolytic bone metastasis, which is dependent on osteo - clast-mediated bone resorption. While current treatments rely on palliative anti-resorptive agents, there is a need to develop a drug based on potential alternative therapies. This study is the first to determine that wedelolactone (WDL), a natural coumarin isolat...
22 CitationsSource
#1Tereza NehybováH-Index: 3
#2Jan ŠmardaH-Index: 24
Last. Petr Beneš (Masaryk University)H-Index: 18
view all 3 authors...
Natural products are often used in drug development due to their ability to form unique and diverse chemical structures. Coumestans are polycyclic aromatic plant secondary metabolites containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. These natural compounds are known for large number of biological activities. Many of their biological effects can be attributed to their action as phytoestrogens and polyphenols. In the las...
25 CitationsSource
#1Yan-Qiu Liu (DICP: Dalian Institute of Chemical Physics)H-Index: 8
#2Libin Zhan (Dalian Medical University)H-Index: 11
Last. Hongbin Xiao (DICP: Dalian Institute of Chemical Physics)H-Index: 21
view all 6 authors...
Abstract Ethnopharmacological relevance Ecliptae herba, also known as “Mo-Han-Lian”, has long been used in China to nourish Kidney and thereafter strengthen bones. Accumulating evidence indicates that extracts of Ecliptae herba have antiosteoporotic effect. However, the effective compounds and cellular mode of action are still unclear. To investigate the effect of ethyl acetate extract of Ecliptae herba (EAE) and its component wedelolactone on proliferation and differentiation of preosteoclastic...
28 CitationsSource
#1Lu Han (Guangzhou University of Chinese Medicine)H-Index: 6
#2Chengjie Sun (Guangzhou University of Chinese Medicine)H-Index: 1
Last. Dongfeng Chen (Guangzhou University of Chinese Medicine)H-Index: 22
view all 10 authors...
Herba Ecliptae (HE) is a typical Chinese herbal medicine used in China for 1500 years. In the study, HE was extracted by various solvents to prepare five HE extracts. They were observed to possess a protective effect against ×OH-induced DNA damage, and scavenging effects on ×OH radical, ×O2− radical, DPPH×(1,1-diphenyl-2-picrylhydrazyl) radical, and ABTS×+ (2,2′-azino-bis(3-ethyl-benzothiazoline-6-sulfonic acid) radical, and reduce Cu2+ ion. The contents of total phenolics and wedelolactone in f...
3 CitationsSource
#1Defeng Xu (URMC: University of Rochester Medical Center)H-Index: 13
#2Tzuhua Lin (URMC: University of Rochester Medical Center)H-Index: 24
Last. Shuyuan Yeh (URMC: University of Rochester Medical Center)H-Index: 74
view all 7 authors...
Estrogen and estrogen receptor (ER)-mediated signaling pathways play important roles in the etiology and progression of human breast, endometrial, and ovarian cancers. Attenuating ER activities by natural products and their derivatives is a relatively practical strategy to control and reduce breast, endometrial, and ovarian cancer risk. Here, we found 3-butoxy-1,8,9-trihydroxy-6H-benzofuro[3,2-c]benzopyran-6-one (BTB), a new derivative of wedelolactone, could effectively inhibit the 17-estradiol...
13 CitationsSource
#1Xican Li (Guangzhou University of Chinese Medicine)H-Index: 19
#2Yaoxiang Gao (Guangzhou University of Chinese Medicine)H-Index: 4
Last. Dongfeng Chen (Guangzhou University of Chinese Medicine)H-Index: 3
view all 9 authors...
Abstract Maclurin, an exceptional member of phytophenol family, was found to effectively protect against mesenchymal stem cells (MSCs) oxidative damage induced by hydroxyl radical ( OH) at 62.1–310.5 μM. Antioxidant assays indicated that maclurin could efficiently protect DNA from OH-induced damage at 114.6–382.2 μM, and scavenge OH, DPPH (1,1-diphenyl-2-picrylhydrazyl radical), ABTS + (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid radical), and bind Cu2+ (IC50 values were respectively 1...
33 CitationsSource
#1Gao-Lei Xi (JLU: Jilin University)H-Index: 2
#2Zai-Qun LiuH-Index: 1
Last. Zai-Qun Liu (JLU: Jilin University)H-Index: 19
view all 2 authors...
Coumestan is a natural tetracycle with a C═C bond shared by a coumarin moiety and a benzofuran moiety. In addition to the function of the hydroxyl group on the antioxidant activity of coumestan, it is worth exploring the influence of the oxygen-abundant scaffold on the antioxidant activity as well. In this work, seven coumestans containing electron-withdrawing and electron-donating groups were synthesized to evaluate the abilities to trap 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationi...
21 CitationsSource
#1Xiyuan Liu (Sookmyung Women's University)H-Index: 4
#2Joo-Won Nam (Ewha Womans University)H-Index: 20
Last. Minsun Chang (Sookmyung Women's University)H-Index: 7
view all 10 authors...
Abstract A novel biological activity of psoralidin as an agonist for both estrogen receptor (ER)α and ERβ agonist has been demonstrated in our study. Psoralidin has been characterized as a full ER agonist, which activates the classical ER-signaling pathway in both ER-positive human breast and endometrial cell lines as well as non-human cultured cells transiently expressing either ERα or ERβ. The estrogenic activity was determined using the relative expression levels of either reporter or the end...
36 CitationsSource
Cited By20
Newest
This paper reviews the research data available in the literature on the chemistry of 4-chloro-3-formylcoumarins reported over the last two to three decades. It covers the synthetic applicability of 4-chloro-3-formylcoumarins in the development of 3,4-substituted coumarins as well as 5-, 6- and 7-membered ring fused coumarin derivatives via classical reaction protocols, microwave-mediated reactions, organo-catalyzed reactions, transition metal-catalyzed reactions, and green reaction protocols.
Source
#2Yangping LiuH-Index: 2
Last. Xican LiH-Index: 19
view all 9 authors...
The search for a safe and effective inhibitor of ferroptosis, a recently described cell death pathway, has attracted increasing interest from scientists. Two hydrolyzable tannins, chebulagic acid and chebulinic acid, were selected for the study. Their optimized conformations were calculated using computational chemistry at the B3LYP-D3(BJ)/6-31G and B3LYP-D3(BJ)/6-311 + G(d,p) levels. The results suggested that (1) chebulagic acid presented a chair conformation, while chebulinic acid presented a...
Source
Source
#1Yanbei Tu (UM: University of Macau)H-Index: 4
#2Ying Yang (UM: University of Macau)
Last. Chengwei He (UM: University of Macau)H-Index: 33
view all 4 authors...
Abstract Naturally occurring coumestans are known as a collection of plant-derived polycyclic aromatic secondary metabolites which are characterized by the presence of an oxygen heterocyclic four-ring system comprising a coumarin moiety and a benzofuran moiety sharing a C=C bond. Recently, there is an increasing attention in excavating the medicinal potential of coumestans, particularly coumestrol, wedelolactone, psoralidin and glycyrol, in a variety of diseases. This review is a comprehensive i...
Source
#1Yangping Liu (Guangzhou University of Chinese Medicine)H-Index: 2
#2Xican Li (Guangzhou University of Chinese Medicine)H-Index: 19
Last. Dongfeng Chen (Guangzhou University of Chinese Medicine)H-Index: 22
view all 7 authors...
Source
#1Ban Chen (Guangzhou University of Chinese Medicine)H-Index: 8
#2Xican Li (Guangzhou University of Chinese Medicine)H-Index: 19
Last. Dongfeng Chen (Guangzhou University of Chinese Medicine)H-Index: 22
view all 7 authors...
The search for safe and effective ferroptosis-inhibitors has become an important topic. Geraniin, an ellagitannin bearing hexahydroxydiphenoyl (HHDP) and dehydrohexahydroxydiphenoyl (DHHDP) groups, was observed to inhibit erastin-induced ferroptosis in bone marrow-derived mesenchymal stem cells (bmMSCs). To determine the mechanism, geraniin was further analyzed using UV-vis spectra and several colorimetric assays, where its IC50 values were always much lower than that of the Trolox positive cont...
1 CitationsSource
#1Fatemeh Salehian (Tehran University of Medical Sciences)H-Index: 5
#2Hamid NadriH-Index: 23
Last. Mehdi Khoobi (Tehran University of Medical Sciences)H-Index: 35
view all 9 authors...
The combination of heterocycles offers a new opportunity to create novel multicyclic compounds having improved biological activity. Coumarins are ubiquitous natural heterocycle widely adopted in the design of various biologically active compounds. Fusing different heterocycles with coumarin ring is one of the interesting approaches to generating novel hybrid molecules having highlighted biological activities. In the efforts to develop heterocyclic-fused coumarins, a wide range of 3,4-heterocycle...
6 CitationsSource
#1Sharise B.R. Berton (UTFPR: Federal University of Technology - Paraná)H-Index: 3
Last. Makoto MatsushitaH-Index: 33
view all 8 authors...
Abstract The chemical reaction involving phenolic antioxidants from plant´ extracts have not been adequately studied. In this study, we investigate a quick, accurate, and innovative strategy to elucidate the ferulic acid reaction employing a conclusive analytical tool (ultra-high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry, UHPLC-ESI-Q-TOF-MS/MS) used in pharmaceutical, cosmetic, food, and biomedical applications. The ...
5 CitationsSource
#1Xican Li (Guangzhou University of Chinese Medicine)H-Index: 19
#2Jie Liu (Guangzhou University of Chinese Medicine)H-Index: 3
Last. Meiling ZhuH-Index: 1
view all 7 authors...
The ellagitannin corilagin and its analogue 1,3,6-tri-O-galloyl-β-d-glucopyranose (TGG) were found to protect bone marrow-derived mesenchymal stem cells (bmMSCs) against erastin-induced ferroptosis...
4 CitationsSource
#1Suman Manandhar (Manipal University)H-Index: 2
#2Shama Prasada Kabekkodu (Manipal University)H-Index: 14
Last. K. Sreedhara Ranganath Pai (Manipal University)H-Index: 1
view all 3 authors...
Abstract Background Wnt signaling pathway plays a major role during development like gastrulation, axis formation, organ development and organization of body plan development. Wnt signaling aberration has been linked with various disease conditions like osteoporosis, colon cancer, hair follicle tumor, Leukemia, and Alzheimer's disease. Phytochemicals like flavonoid, glycosides, polyphenols, have been reported to directly target the markers of Wnt signaling in different disease models. Purpose Th...
2 CitationsSource