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Molecules 2018, 23(10), 2610; https://doi.org/10.3390/molecules23102610

Steric Effect of Antioxidant Diels-Alder-Type Adducts: A Comparison of Sanggenon C with Sanggenon D

1,2,†,* , 3,4,†
,
3,4
,
3,4
,
1
,
1
,
5
and
3,4,*
1
School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
2
Innovative Research & Development Laboratory of TCM, Guangzhou 510006, China
3
School of Basic Medical Science, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
4
The Research Center of Basic Integrative Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
5
School of Biomedical Sciences, Faculty of Medicine, The Chinese University of Hong Kong, Sha Tin, Hong Kong 999077, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 18 July 2018 / Revised: 8 October 2018 / Accepted: 10 October 2018 / Published: 11 October 2018
(This article belongs to the Special Issue Antioxidants Chemistry and Applications)
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Abstract

Sanggenons C and D are two Diels-Alder-type adducts from Chinese crude drug Sang-bai-pi. Structurally, both sanggenons construct stereoisomers. In the study, they were comparatively determined using four antioxidant assays, including ferric ion reducing antioxidant power (FRAP) assay, Cu2+-reducing assay, 1,1-diphenyl-2-picryl-hydrazl (DPPH•)-scavenging assay, and 2,2′-azino-bis (3-ethylbenzo-thiazoline-6-sulfonic acid radical (ABTS•+)-scavenging assay. Their Fe2+-binding reactions were explored using UV-Vis spectra. Finally, their cytoprotective effects were evaluated using flow cytometry. In electron transfer (ET)-based FRAP and Cu2+-reducing assays, sanggenon D was found to have lower IC50 values than sanggenon C; however, in multi-pathway-based DPPH•-scavenging and ABTS•+-scavenging assays, sanggenon C possessed lower IC50 values than sanggenon D. UV-Vis spectra suggested that sanggenon C generated a bathochromic-shift (286 nm → 302 nm) and displayed stronger UV absorption than sanggenon D. In flow cytometry, sanggenon C and sanggenon D, respectively, exhibited 31.1% and 42.0% early apoptosis-percentages towards oxidative-stressed mesenchymal stem cells (MSCs). In conclusion, both sanggenons may undergo multiple pathways (e.g., ET and Fe2+-binding) to protect MSCs against oxidative stress. In the mere ET aspect, sanggenon D possesses a higher level than sanggenon C, while in multi-pathway-based radical-scavenging, Fe2+-binding, and cytoprotection aspects, sanggenon C is more active than sanggenon D. These discrepancies can conclusively be attributed to the steric effect. View Full-Text
Keywords: antioxidant; Diels-Alder-type adduct; sanggenon C; sanggenon D; steric effect antioxidant; Diels-Alder-type adduct; sanggenon C; sanggenon D; steric effect
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Li, X.; Ren, Z.; Wu, Z.; Fu, Z.; Xie, H.; Deng, L.; Jiang, X.; Chen, D. Steric Effect of Antioxidant Diels-Alder-Type Adducts: A Comparison of Sanggenon C with Sanggenon D. Molecules 2018, 23, 2610.

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