Structure Elucidation of Two New Norlignans from Anemone vitifolia and Their Anti‐Inflammatory Activities

Abstract

Two new norlignans together with two known phenylpropanoids were isolated from the whole herb of Anemone vitifolia. All compounds were reported from this plant for the first time. The structures of these compounds were identified by comprehensive HR‐ESI‐MS, 1D and 2D NMR spectroscopic data analysis and comparison with literature data. Additionally, bioactivity study results showed that two new compounds have potential anti‐inflammatory activity. The plausible biosynthetic pathway for these compounds were also speculated in this article.

Antiviral and Antioxidant Components from the Fruits of Illicium verum Hook.f. (Chinese Star Anise)

“…The NMR spectroscopic data (Tables 1 and 2) of 1 resembled those of a norlignan (9). 31 The main differences were the presence of an additional E-configured double bond group [δ H 6.81 (d, J = 16.3 Hz), 6.22 (dd, J = 16.3, 5.0 Hz); δ C 130.3, 123.6] in 1. It was verified by the 1 H− 1 H correlation spectroscopy (COSY) correlations (Figure 2) between H-2 (δ H 5.52) and H-8 (δ H 6.…”

“…The investigation of the constituents from the fruits of I. verum led to the isolation of 6 new compounds, illiciumiones A–F ( 1 – 6 ), and 14 known compounds, which were identified as (−)-bornyl p -coumarate ( 7 ), anemonenorin B ( 8 ), anemonenorin A ( 9 ), harmandianone ( 10 ), verimol A ( 11 ), verimol D ( 12 ), 3-methylbut-2-enyl-4-hydroxybenzoate ( 13 ), anisic acid ( 14 ), 4-hydroxy-3-(3-methyl-2-buten-1-yl) benzaldehyde ( 15 ), ( R )-2-(4-methylcyclohex-3-en-1-yl) propan-2-yl ( E )-3-(4-hydroxyphenyl) acrylate ( 16 ), ( E )-methyl p -coumarate ( 17 ), ( E )-3-(4-methoxyphenyl) acrylaldehyde ( 18 ), (1′ S ,2′ S )-1′-(1-methoxyphenyl)-propane-1′,2′-diol ( 19 ), and (1 S ,2 R )-1-ethoxy-1-(4-methoxyphenyl) propan-2-ol ( 20 ) using spectroscopic methods and comparison with related literatures. Among the known compounds, compounds 7 – 10 , 13 , 15 – 18 , and 20 were first reported to be isolated from the fruits of I.…”

“…The 1 H NMR spectrum (Table ) showed characteristic signals for three aromatic AB spin systems [δ H 7.36 (d, J = 8.7 Hz, 2H), 6.84 (d, J = 8.7 Hz, 2H); 7.05 (d, J = 8.6 Hz, 2H), 6.70 (d, J = 8.6 Hz, 2H); 6.89 (d, J = 8.1 Hz, 2H), 6.73 (d, J = 8.1 Hz, 2H)] and three methoxyls [δ H 3.80 (s, 3H), 3.74 (s, 3H), 3.72 (s, 3H)]. The NMR spectroscopic data (Tables and ) of 1 resembled those of a norlignan ( 9 ) . The main differences were the presence of an additional E -configured double bond group [δ H 6.81 (d, J = 16.3 Hz), 6.22 (dd, J = 16.3, 5.0 Hz); δ C 130.3, 123.6] in 1 .…”

Three Pairs of Enantiomeric Sesquiterpenoids from Syringa pinnatifolia

“…After 24 h of treatment, the plates were immediately removed from the incubators; 50 μL of the supernatant in each well was collected, and 100 μL of the Griess reagent (reagent A and reagent B, Applygen Technologies Inc., P. R. China) was added to each well to assess the NO production. Their OD values were read at 540 nm. , …”

(+/−)‐Alashanoid N, Two Enantiomeric Sesquiterpenes from Syringa pinnatifolia

“…NO production inhibition assay was performed as previously reported [16,17] . Briefly, RAW 264.7 cells were seeded at concentration of 8×10 4 cells/well in a 96‐well plate, and incubated at 37 °C in a humidified atmosphere of 5 % CO 2 at for 24 h. The cells were treated with a volume of 50 μL serum containing medium containing positive control and test compounds.…”