Abstract
Patrinia scabiosaefolia is a medical and edible Chinese herb with high nutritional and medicinal value. The continuing study of its chemical constituents led to the discovery of nine unique iridoids and iridoid glycosides, including three new iridoids (1-3) and six previously unknown irioid glycosides (5-10), and one known compound (4). Among them, compound 1 was a deformed iridoid, while compounds 3, 5-7, and 10 formed a new ring in their skeletons which was uncommon in this genus. For compound 3, the new ring existed between C-3 and C-10, while a 1,3-dioxane appeared between C-7 and C-10 in compounds 5-7 and 10. Moreover, compound 10 was a bis-iridoid glycoside, which was the first reported in P. scabiosaefolia. And the sugar of irioid glycosides (5-10) was glucose at C-11, except in 9 which had a 5-deoxyglucose moiety. All their structures were confirmed based on the extensive spectroscopic analysis, including IR, UV, HR-ESI-MS, ECD, and 1D- and 2D-NMR experiments. Their cytotoxic activities against HL-60, A-549, SMMC-7721, MCF-7, SW480 were also tested.
Highlights
There are about 400 species in 13 genera of Valerianaceae, mostly distributed in northern temperate zones and the subtropics or frigid zones
We found a series of iridoids from ethyl acetate extract of P. scabiosaefolia, including three bis-iridoids which were first reported (Liu et al, 2017a,b; Liu et al, 2019)
Compound 1 was a deformed iridoid, compound 3 formed a cycle between C-3 and C-10, compounds 5-7 with a 1,3-dioxane between C-7 and C-10, and compound 10 was a bis-iridoid glycoside, which was the first reported in P. scabiosaefolia
Summary
There are about 400 species in 13 genera of Valerianaceae, mostly distributed in northern temperate zones and the subtropics or frigid zones. The n-butanol extract was subjected to silica gel column chromatography eluted with a gradient of CHCl3-MeOH (8:1→ 0:1, v/v) to obtain five fractions 1-5 by TLC plate analysis. Fraction 2 (22 g) was separated by silica gel column chromatography eluted with a gradient system of CHCl3-MeOH (6:1→ 1:1, v/v) to afford 4 subfractions (Fr. to Fr.). Fraction 3 (15 g) was subjected to silica gel column chromatography eluted with a gradient system of CHCl3-MeOH (5:1→ 1:1, v/v) to afford 6 subfractions (Fr. to Fr.). Patrinoside F (9): light yellow oil; [α]24 D-74.0 (c0.32, MeOH); UV (MeOH) λmax (log ε): 207 (4.18) nm; IR (KBr) νmax 3,441, 2,925, 2,860, 1,727, 1,639, 1,121, 1,065 cm−1; 1H and 13C NMR data, see Table 2; positive ESIMS m/z 467 [M + Na]+; HREIMS m/z 467.1889 [M + Na]+ (calcd for C26H40O11Na, 467.1888). The calculated ECD spectra were generated by the program SpecDis using a Gaussian band shape with 0.3eV exponential half-width from dipole-length dipolar and rotational strengths (Bruhn et al, 2013)
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