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To study the chemical constituents of Pteris ensiformis, silica gel, gel, MCI, C18 and other column chromatography were used for separation and purification, and their structures were identified by 1H-NMR, 13C-NMR, MS, IR and othe spectral data; the anti-tumor and anti-coagulation activities of some monomers were screened by MTS, APTT, PT and TT. The results were as follows: (1) A total of 15 compounds were isolated from P. ensiformis, the compounds were 2-hydroxy-acetylpyrrole (1), N-(3-carboxypropyl)-2-acetylpyrrole (2), 3-hydroxy-2-methylpyridine (3), N-methylhydroxylamine (4), pterosin S 13-O-glucoside (5), obtupterosin C (6), ent-11α-hydroxy-15-oxokauran-19-oic acid (7), ent-11α-hydroxy-15-oxokaur-16-en-19-oic acid (8), β-sitosterol (9), ent-11α-hydroxy-15-oxokaur-16-en-19-oic acid-O-glucopyranoside (10), 5, 5′-dibutoxy-2, 2′-bifuran (11), 5, 5′-di (2-ethyl-hexyloxy)-2, 2′-bifuran (12), (-)-loliolide (13), succinic acid (14), fumaric acid (15). Compound 1 is a new natural product of pyrrole alkaloids. Compounds 1-7, 10-15 were isolated from P. ensiformis for the first time, and compounds 1, 3, 4 were isolated from Pteris for the first time. (2) The results of activity test showed that compounds 1, 2, 3, 5, 6 and 10 inhibited the growth of tumor cells HL-60, A549, SMMC-7721, MDA-MB-231 and SW480 in vitro at a concentration of 40 μmol·L-1, At the concentration of 2.0 mmol·L-1, compounds 1, 2, 3 and 6 shortened APTT and compounds 1, 5 and 6 prolonged PT. The study enriches the chemical constituents of P. ensiformis from Guizhou and provides a material basis for the development of anti-tumor drugs.

C30H27NO5S, monoclinic, P21 (no. 4), a = 10.4329(16) Å, b = 11.6208(18) Å, c = 11.8268(18) Å, β = 114.257(5)°, V = 1307.3(4) Å3, Z = 2, Rgt(F) = 0.0685, wRref (F2) = 0.1547, T = 273(2) K.

C20H26O3, orthorhombic, P21212 (no. 18), a = 10.0361(11) Å, b = 18.542(2) Å, c = 9.7357(12) Å, V = 1811.7(4) Å3, Z = 4, Rgt(F) = 0.0535, wRref(F2) = 0.1553, T = 273(2) K.

C18H16O8, monoclinic, P21/n (no. 14), a = 14.5762(6) Å, b = 6.6791(3) Å, c = 17.4240(7) Å, β = 103.5820(10)°, V = 1648.89(12) Å3, Z = 4, R gt(F) = 0.0436, wR ref(F 2) = 0.1218, T = 293(2) K.

C37H34NO2P, monoclinic, P21/c (no. 14), a = 9.3479(3) Å, b = 23.0805(8) Å, c = 13.7819(5) Å, β = 102.462(10)°, V = 2903.44(17) Å3, Z = 4, Rgt(F) = 0.0458, wRref(F2) = 0.1309, T = 300(2) K.

C18H18N3O4S, monoclinic, Cc (no. 9), a = 10.8839(14) Å, b = 14.2825(18) Å, c = 13.0717(16) Å, β = 108.618(3)°, V = 1925.6(4) Å3, Z = 4, Rgt(F) = 0.0359, wRref(F2) = 0.0812, Flack parameter = 0.009(6), T = 298(2) K.

C23H19F2NO2S, orthorhombic, Pna21 (no. 33), a = 13.8754(8) Å, b = 7.7354(5) Å, c = 18.4616(11) Å, V = 1981.5(2) Å3, Z = 4, Rgt(F) = 0.0449, wRref(F2) = 0.1066, T = 300(2) K.

C30H27NO5S, monoclinic, P21 (no. 4), a = 10.4329(16) Å, b = 11.6208(18) Å, c = 11.8268(18) Å, β = 114.257(5)°, V = 1307.3(4) Å3, Z = 2, Rgt(F) = 0.0685, wRref (F2) = 0.1547, T = 273(2) K. [ABSTRACT FROM AUTHOR]

C20H26O3, orthorhombic, P21212 (no. 18), a = 10.0361(11) Å, b = 18.542(2) Å, c = 9.7357(12) Å, V = 1811.7(4) Å3, Z = 4, Rgt(F) = 0.0535, wRref(F2) = 0.1553, T = 273(2) K. [ABSTRACT FROM AUTHOR]

Detailed analysis of its crystal structure revealed that the methoxyl groups located at C-3 and C-6 are turned out from the plane of chromone skeleton, which is in accordance with that of casticin, the methyl etherified derivative at 4'-OH of the title compound [[11], [13]]. The title compound (131.8 mg) was obtained from the E4 fraction I via i repeated silica gel column chromatography. The ethyl acetate fraction (0.219 kg) was then separated over silica gel column chromatography eluted with petroleum ether/ethyl acetate and dichloromethane/methanol in gradient, affording six fractions of E1-E6. [Extracted from the article]

C37H34NO2P, monoclinic, P21/c (no. 14), a = 9.3479(3) Å, b = 23.0805(8) Å, c = 13.7819(5) Å, β = 102.462(10)°, V = 2903.44(17) Å3, Z = 4, Rgt(F) = 0.0458, wRref(F2) = 0.1309, T = 300(2) K. [ABSTRACT FROM AUTHOR]

In addition to the basic pyrazolone skeleton, the title compound contains a I i -diketone moiety, and a 4-(4-bromophenyl)thiazol-2-yl group. Dehydroacetic acid has also been employed as the starting material to obtain pyrazolone derivatives containing a -diketone moiety [[7]]. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters. [Extracted from the article]

C23H19F2NO2S, orthorhombic, Pna21 (no. 33), a = 13.8754(8) Å, b = 7.7354(5) Å, c = 18.4616(11) Å, V = 1981.5(2) Å3, Z = 4, Rgt(F) = 0.0449, wRref(F2) = 0.1066, T = 300(2) K. [ABSTRACT FROM AUTHOR]

C20H26O3, orthorhombic, P21212 (no. 18), a = 10.0361(11) Å, b = 18.542(2) Å, c = 9.7357(12) Å, V = 1811.7(4) Å3, Z = 4, Rgt(F) = 0.0535, wRref(F2) = 0.1553, T = 273(2) K. [ABSTRACT FROM AUTHOR]

Detailed analysis of its crystal structure revealed that the methoxyl groups located at C-3 and C-6 are turned out from the plane of chromone skeleton, which is in accordance with that of casticin, the methyl etherified derivative at 4'-OH of the title compound [[11], [13]]. The title compound (131.8 mg) was obtained from the E4 fraction I via i repeated silica gel column chromatography. The ethyl acetate fraction (0.219 kg) was then separated over silica gel column chromatography eluted with petroleum ether/ethyl acetate and dichloromethane/methanol in gradient, affording six fractions of E1-E6. [Extracted from the article]

Background: Excessive inflammation poses significant risks to human physical and mental health. Astilbe grandis , a traditional Miao medicine, is renowned for its anti-inflammatory properties. However, the specific anti-inflammatory effects and mechanisms of many compounds within this plant remain unclear. This study aims to investigate the anti-inflammatory effects and mechanisms of two characteristic oleanane triterpenoids, 3 α -acetoxyolean-12-en-27-oic acid ( 1 ) and 3 β -acetoxyolean-12-en-27-oic acid ( 2 ), isolated from Astilbe grandis , using lipopolysaccharide (LPS)-induced Macrophages., Methods: The anti-inflammatory effects and mechanisms of compounds 1 and 2 were investigated by establishing an LPS-induced inflammation model in RAW 264.7 cells and THP-1 cells. Nitric oxide (NO) levels were assessed using the Griess method. The concentrations of tumor necrosis factor-alpha (TNF- α ), interleukin-6 (IL-6), and interleukin-1beta (IL-1 β ) were measured via enzyme-linked immunosorbent assay (ELISA). The expression of cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) was determined using western blotting and quantitative real-time PCR (qRT-PCR). Additionally, the phosphorylation level of p65 in nuclear factor-kappa B (NF- κ B) was assessed through western blotting. The nuclear translocation of NF- κ B p65 was assessed through immunofluorescence staining. Finally, the binding affinity of the compounds to NF- κ B p65 target was validated through molecular docking., Results: Compounds 1 and 2 significantly inhibited the expression of NO, TNF- α , IL-6, IL-1 β , COX-2, and iNOS in LPS-induced Macrophages. Mechanistically, they attenuated the activation of the NF- κ B signaling pathway by downregulating the phosphorylation level and nuclear translocation of p65., Conclusion: This study elucidates the anti-inflammatory activities and potential mechanism of the characteristic oleanane triterpenoids with C-14 carboxyl group, compounds 1 and 2 , in LPS-induced Macrophages by inhibiting the NF- κ B signaling pathway for the first time. These findings suggest that these two compounds hold promise as potential candidates for anti-inflammatory interventions in the future., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2024 Yue, Luo, Zhao, Zhao, Ye, He and Zou.)