# Chemical Constituents, Neuroprotective and Antioxidant Potential of _Klasea centauroides_ Leaves
## 3 Results
### LC-MS Profiling of K. centauroides Leaf Extract
centauroides_ compounds of integristerone A (**9**), 20-hydroxycedysone (**14**), and 2-desoxy-20-hydroxyecdysone (**20**) found in herb [9], and the newly detected 20-hydroxycedysone 3-\(O\)-glucoside (**6**), turkesterone (**10**), polyodine B (**15**), cedysone (**19**), 20-hydroxyecdysone 3-\(O\)-acetate (**21**), and 2-deoxyecdysone (**22**). Previously, turkesterone was found in _Serratula coronata_ subsp. _coronata_[59]; polyodine B in _K. chinensis_[60] and _K. quinquefolia_[61]; cedysone in _K. radiata_[62]; 20-hydroxycedysone 3-\(O\)-acetate in _K. chinensis_[63]; and 20-hydroxyecdysone 3-\(O\)-glucose, ecdysone, and 2-deoxyecdysone in the _Klasea_ genus for the first time. Compound **5** was tentatively described as 20-hydroxyecdysone \(O\)-hexoside for its similarity to 20-hydroxyecdysone 3-\(O\)-glucoside (**6**). Two compounds, **7** and **8**, showed the loss of a pentose fragment (\(m/z\) 132), and compounds **11-13** lost the desoxyhexoside fragment (\(m/z\) 146) with a similar aglycone fragmentation close to 20-hydroxycedysone, allowing annotation of the compounds as 20-hydroxyecdysone \(O\)-pentosides (**7**, **8**) and 20-hydroxyecdysone \(O\)-desoxyhexosides (**11-13**). The structures of 16, 17, and 18 were described as 2-deoxy-20-hydroxyecdysone \(O\)-hexoside, 20-hydroxyecdysone \(O\)-acetyl-\(O\)-hexoside, and 2-deoxyecdysone \(O\)-hexoside, respectively, based on the same rules. The natural glycosylated 20-hydroxyecdysones with pentosyl and desoxyhexosyl fragments are still unknown, in contrast to 2-deoxy-20-hydroxyecdysone 3-\(O\)-glucose from _Paratinospora sagittata_ (Oliv.) [PERSON] (syn. _Tinospora capillipes_ Gagnep., Menispermaceae) [64] and 2-deoxy-20-hydroxyecdysone 25-\(O\)-glucose from _Silene gigantea_ (L.) L. (Caryophyllaceae) [65], which are close to **16**; 20-hydroxyecdysone 3-\(O\)-acetate 2-\(O\)-glucose and 2-\(O\)-galactosidase from _K. chinensis_[66] are close to **17**; and 2-deoxyecdysone 22-\(O\)-glucose from _Silene praemixta_ [PERSON] [67] is close to **18**. \begin{table}
\begin{tabular}{c c c c c} \hline \hline
**No.** & **t, min** & **Negative Ionization, \(m/z\)** & **Positive Ionization, \(m/z\)** & **Compound [Ref.]** & **IL*** \\ \hline
**38** & 10.83 & \
\begin{tabular}{c} 477 [M-H]\({}^{*}\), \\ 301 [(M-H)-GlcNAc]\({}^{*}\) \\ \end{tabular} & 479 [M+H]\({}^{+}\), 303 [(M+H)-GlcNAc]\({}^{*}\) &
\begin{tabular}{c} Diosmetin \\ 7-\(O\)-glucuronide [19] \\ \end{tabular} & 1 \\ \hline
**39** & 11.12 & \begin{tabular}{c} 785 [M-H]\({}^{*}\), \\ 623 [(M-H)-Caf]\({}^{*}\), \\ 261 [(M-H)-Caf-Hex]\({}^{*}\), \\ 287 [(M+H)-Caf-Hex-HexA]\({}^{*}\) \\ \end{tabular} & \
\begin{tabular}{c} 787 [M+H]\({}^{+}\), 625 [(M+H)-Caf]\({}^{+}\), \\ 287 [(M+H)-Caf-Hex-HexA]\({}^{*}\) \\ \end{tabular} &
\begin{tabular}{c} Luteolin \\ \(O\)-hexuromide-\(O\)-ex-tetrae [54] \\ \end{tabular} & 2 \\ \hline
**40** & 12.48 & \begin{tabular}{c} 769 [M-H]\({}^{*}\), \\ 607 [(M-H)-Caf]\({}^{*}\), \\ 445 [(M-H)-Caf-Hex]\({}^{*}\), \\ 269 [(M-H)-Caf-Hex-HexA]\({}^{*}\) \\ HexA]\({}^{*}\) \\ \end{tabular} & \
\begin{tabular}{c} Apigenin \\ 771 [M+H]\({}^{+}\), 609 [(M+H)-Caf]\({}^{+}\), \\ 271 [(M+H)-Caf-Hex-HexA]\({}^{*}\) \\ \end{tabular} &
\begin{tabular}{c} Apigenin \\ 70-hexuromide-\(O\)- \\ hexoside-\(O\)- \\ acfatee [54] \\ \end{tabular} & 2 \\ \hline
**41** & 12.76 & \
\begin{tabular}{c} 799 [M-H]\({}^{*}\), \\ 637 [(M-H)-Caf]\({}^{*}\), \\ 475 [(M-H)-Caf-Hex]\({}^{*}\), \\ 299 [(M-H)-Caf-Hex-HexA]\({}^{*}\) \\ HexA]\({}^{*}\) \\ \end{tabular} &
\begin{tabular}{c} Chrysoeriol \\ \(O\)-hexuromide-\(O\)- \\ hexoside-\(O\)- \\ caffee [54] \\ \end{tabular} & 2 \\ \hline \hline \end{tabular}  
* Identification levels: (1) identified compounds after comparison of UV, mass-spectral data, and retention time with reference standards; (2) putatively annotated compounds after comparison of UV and mass-spectral data with literature data.  
\end{table} 
Table 1: Cont.