NO inhibitory constituents from Glycosmis craibii var. glabra

Abstract

Six novel compounds, comprising three quinolones (1a, 1b, and 2) and three flavanones (3-5), along with seven known analogs (6-13), were isolated from the 95% EtOH extract of the stems and leaves of Glycosmis craibii var. glabra. The structures of the new compounds were elucidated using HR-ESI-MS, UV, and 1D and 2D nuclear magnetic resonance (NMR) data analysis. The absolute configurations were determined through Mosher ester and electronic circular dichroism (ECD) spectral analysis. Compounds 2, 6, 9, and 10 demonstrated inhibition of nitric oxide (NO) production stimulated by lipopolysaccharide in BV-2 microglial cells, with IC₅₀ values ranging from 13.5 to 20.1 μmol·L⁻¹, comparable to the positive control, dexamethasone.

Keywords

Glycosmis craibii var. glabra / Quinolone / Flavanone / NO inhibition

References

[1] Shoja MH, Reddy ND, Nayak PG, et al. Glycosmis pentaphylla (Retz. ) DC arrests cell cycle and induces apoptosis via caspase-3/7 activation in breast cancer cells[J]. J Ethnopharmacol, 2015, 168: 50-60.

[2] Liu ZL, Yang K, Bai PH, et al. Gas chromatography-mass spectrometric analysis of essential oil of aerial parts of Glycosmis parviflora (Sims) Little (Rutaceae)[J]. Trop J Pharm Res, 2014, 13(2): 275-280.

[3] Silambujanaki P, Bala Tejo Chandra C, Anil Kumar K, et al. Wound healing activity of Glycosmis arborea leaf extract in rats[J]. J Ethnopharmacol, 2011, 134(1): 198-201.

[4] Khan MF, Negi N, Sharma R, et al. Bioactive flavanoids from Glycosmis arborea[J]. Org Med Chem Lett, 2013, 3(1): 4.

[5] Yang G, Wu Y, Chen Y. Alkaloids from the stems of Glycosmis pentaphylla[J]. Helv Chim Acta, 2012, 95(8): 1449-1454.

[6] Yahayu MA, Rahmani M, Hashim NM, et al. Two new acridone alkaloids from Glycosmis macrantha[J]. Molecules, 2011, 16(6): 4401-4407.

[7] Sharma RK, Semwal S, Negi DS. A new flavone C-glucoside from Glycosmis arborea (Rutaceae)[J]. Chin Chem Lett, 2010, 21(12): 1443-1445.

[8] Lukaseder B, Vajrodaya S, Hehenberger T, et al. Prenylated flavanones and flavanonols as chemical markers in Glycosmis species (Rutaceae)[J]. Phytochemistry, 2009, 70(8): 1030-1037.

[9] Ito C, Kondo Y, Wu TS, et al. Chemical constituents of Glycosmis citrifolia (Willd. ) Lindl. Structures of four new acridones and three new quinolone alkaloids[J]. Chem Pharm Bull, 2000, 48(1): 65-70.

[10] Nian H, Xiong H, Zhong F, et al. Anti-inflammatory and antiproliferative prenylated sulphur-containing amides from the leaves of Glycosmis pentaphylla[J]. Fitoterapia, 2020, 146: 104693.

[11] Editorial Committee of Flora of China. Flora of China[M]. Beijing: Science Press, 1997: 121.

[12] Chen H, Zhu S, Tu P, et al. Chemical constituents from the stems and leaves of Glycosmis craibii var. glabra (Craib) Tanaka and their chemotaxonomic significance [J]. Biochem Syst Ecol, 2022, 105: 104492.

[13] Chen H, Lin J, Zhu S, et al. Anti-inflammatory constituents from the stems and leaves of Glycosmis ovoidea Pierre[J]. Phytochemistry, 2022, 203: 113369.

[14] Li C, Zhou Y, Tu P, et al. Natural carbazole alkaloid murrayafoline A displays potent anti-neuroinflammatory effect by directly targeting transcription factor Sp1 in LPS-induced microglial cells[J]. Bioorg Chem, 2022, 129: 106178.

[15] Lv H, Wang S, Zeng K, et al. Anti-inflammatory coumarin and benzocoumarin derivatives from Murraya alata[J]. J Nat Prod, 2015, 78(2): 279-85.

[16] Choi Y, Seo C, Jeong W, et al. Glycopentanolones A-D, four new geranylated quinolone alkaloids from Glycosmis pentaphylla[J]. Bioorg Chem, 2019, 87: 714-719.

[17] Tanjung M, Saputri R, Wahjoedi R, et al. 4-Methoxy-3-(3-methylbut-2-en-1-yl)-7-[(3-methylbut-2-en-1-yl)oxy]quinolin-2(1H)-one from Melicope Moluccana T. G. Hartley[J]. Molbank, 2017, 2017(2): M939.

[18] Park J, Chung B, Lee W, et al. Sortase A-inhibitory coumarins from the folk medicinal plant Poncirus trifoliata[J]. J Nat Prod, 2020, 83(10): 3004-3011.

[19] Rashid MA, Gray AI, Waterman PG, et al. Coumarins from Phebalium tuberculosum ssp. megaphyllum and Phebalium filifolium[J]. J Nat Prod, 1992, 55(7): 851-858.

[20] Slade D, Ferreira D, Marais JPJ. Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids[J]. Phytochemistry, 2005, 66(18): 2177-215.

[21] Gaffield W. Circular dichroism, optical rotatory dispersion and absolute configuration of flavanones, 3-hydroxyflavanones and their glycosides: determination of aglycone chirality in flavanone glycosides[J]. Tetrahedron, 1970, 26(17): 4093-4108.

[22] Gupta RK, Krishnamurti M. Ovalichalcone A and its synthetic analogs[J]. Indian J Chem, Sect B: Org Chem Incl Med Chem, 1979, 17B(3): 291.

[23] De Moura NF, Ribeiro HB, Machado ECS, et al. Benzophenanthridine alkaloids from Zanthoxylum rhoifolium[J]. Phytochemistry, 1997, 46(8): 1443-1446.

Funding

National Natural Science Foundation of China(81973199)

National Natural Science Foundation of China(82173949)

National Natural Science Foundation of China(81773864)

Key Research and Development Project of Shandong Province(2021CXGC010507)