ChemInform Abstract: Novel Antioxidant neo‐Clerodane Diterpenoids from Scutellaria barbata

Abstract

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The NMR Spin Systems of Scutellaria 8β,13-Epoxy-neo-clerod-3-en-15,16-olides and Revision of 1H and 13C NMR Spectra Reported Data

“…Besides 13 C data, the assignment as C-11 vs C-1 substitution (a matter of structural revision as seen) in 1 unambiguously from the HMBC correlations of HC-1 with C-2, C-3, and/or C-5 or HC-11 with C-8, C-12, and/or C-13.…”

“…Apparently, there is no recommendation to save table space or improve data accuracy. Table 3 displays a selected set of 13 C NMR data to discuss some regular patterns whereas a compilation will be available as Supplemental Material (Supplemental Table SM1). When spectra were available with more than 1 decimal, reported data have been corrected to 2 or more, to point this fact.…”

“…Scutebata F (5) 12 was reported as possessing the same 1β,6α,7β-trihydroxy-structural framework as scutebata D, 13(S*)-1β-nicotinoyloxy-6α,7β-diacetoxy-8β,13-epoxy-3- 13 and the evident identity of scutebata F and barbatine C was concluded from the 1 H NMR spectra of both, available free in the respective Supplemental Materials. Scutebarbatine F was the third compound with the same structure, a conclusion of the revision by Wang et al 10 The 13 C data of all 3 are a remarkable supporting evidence.…”

Constituents from Scutellaria barbata Inhibiting Nitric Oxide Production in LPS‐Stimulated Microglial Cells

“…In our continuing search for active constituents of S. barbata inhibiting NO production from BV2 microglial cells, eight compounds including two flavonoids ( 1 and 5 ) and six neo‐clerodane diterpenoids ( 2 – 4 and 6 – 8 ) were isolated from chloroform‐soluble fraction. Eight known isolates were identified by the extensive analysis of spectroscopic data and comparison with the literature values as 6‐methoxynaringenin ( 1 ), scutebarbatine W ( 2 ), scutebatas B ( 3 ), scutebarbatine B ( 4 ), 6‐ O ‐methylscutellarein ( 5 ), scutebarbatine A ( 6 ), 6‐ O ‐nicotinoylscutebarbatine G ( 7 ), and scutebarbatine X ( 8 ) ( Fig. ).…”

Acylated neo -clerodanes and 19- nor - neo -clerodanes from the aerial parts of Scutellaria coleifolia (Lamiaceae)

“…More than 100 neo-clerodanes have been isolated from this genus, and have been classified into 8b-hydroxy-neo-clerod-13-en-15,16-olides (Cole et al, 1990;Miyaichi et al, 1994;de la Torre et al, 1997;Hussein et al, 1996;Malakov and Papanov, 1996;Kizu et al, 1997;Rodríguez et al, 1997;Esquivel et al, 2001;Nguyen et al, 2009;Shang et al, 2010;Raccuglia et al, 2010;Wang et al, 2012), 8b,13-epoxy-neo-clerodane-15,16-olides (Bozov et al, 1993;Malakov and Papanov, 1996;Kizu et al, 1997;Esquivel et al, 2001;Nguyen et al, 2009;Shang et al, 2010;Raccuglia et al, 2010;Lee and Shim, 2011;Wang et al, 2012) and 11,16;15,16-diepoxy-neo-clerodanes (Cole et al, 1990;de la Torre et al, 1995de la Torre et al, , 1997Rodríguez et al, 1997;Ohno et al, 1996Ohno et al, , 1997Kizu et al, 1998;Bruno et al, 2000;Wang et al, 2012), respectively. These neo-clerodanes have attracted interest of researchers for their biological activities, which include anti-feedant (Cole et al, 1990;Muñoz et al, 1997;Raccuglia et al, 2010), anti-oxidant (Nguyen et al, 2009) and anti-cancer activities (Wang et al, 2012).…”