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.
Highlights
Diels-Alder-type adducts are unusual natural products occurring in plants
The evidence is believed to be helpful to explain the steric effects in other Diels-Alder-type adducts, and to design new cytoprotector for stem cell technology
The (Figure 3), the mesenchymal stem cells (MSCs) in the control, model, sanggenon C, and sanggenon D groups exhibited 4.37 ± 0.05%, results revealed that sanggenon C could effectively inhibit apoptosis of MSCs under oxidative stress
Summary
Diels-Alder-type adducts are unusual natural products occurring in plants. Two earliest-found Diels-Alder-type adducts sanggenons C and D are typical examples (Figure 1) [2,3]. To the best of our knowledge, no cutting-edge biotechnology, such as stem cell technology, has been used to study. Stem cell technology is undoubtedly one of the most attractive therapeutic tools in recent decades. This technology brings hope to the treatment of human diseases through tissue transplantation and regeneration. No relevant study has discussed the possible steric effect in Diels-Alder-type adducts (and other phenolics). The evidence is believed to be helpful to explain the steric effects in other Diels-Alder-type adducts, and to design new cytoprotector for stem cell technology
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