Phytochemical composition profile of Scutellaria bornmuelleri methanolic extract using GC-MS analysiss

Document Type : Original Article


1 Department of Plant Production and Genetics, Faculty of Agriculture, University of Zanjan, Zanjan, Iran

2 Department of Soil Science, Faculty of Agriculture, University of Zanjan, Zanjan, Iran

3 School of Pharmacy, Zanjan University of Medical Sciences, Zanjan, Iran Zanjan Pharmaceutical Biotechnology Research Center, Zanjan University of Medical Sciences, Zanjan, Iran


Background and aims: Scutellaria bornmuelleri Hausskn. ex Bornm. ssp. mianensis Rech.f is one of the species of Scutellaria genus, Lamiaceae, that have long been used in traditional medicine. The aim of this study was to analyze the methanol extract of aerial parts of the plant.
Methods: Chemical composition of methanol extract of S. bornmuelleri aerial parts was determined using gas chromatography/mass spectrometry (GC/MS).
Results: A total of 113 compounds were identified in the methanol extract of S. bornmuelleri shoot. The main compounds were organic acids (23.649%), aldehydes (14.516%), ketones (11.353%), alcohols (5.439%), carbohydrates (3.85%), methyl esters (3.713%), sugars (1.953%), acetates (1.933%), terpenes (2.522%), metal related compounds (1.229%), amides (1.169%) and other compounds (9.423%). Pentacosane (1.021%) was identified as the main carbohydrate, n-hexadecanoic acid (4.1%) as the major acid, 5-hydroxymethylfurfural (10.063%) as the main aldehyde, 4H-Pyran-4-one, 2,3-dihydro-3,5-di hydroxy-6-methyl- (2.289%) as the main ketone, syringol (2.395) as the main alcohol, phytol (0.66%) as the main terpene, isopropyl acetate (0.728%) as the main acetate, propanoic acid, 2-oxo-, methyl ester (1.298%) as the main methyl ester, 9-octadecenamide, (Z)- (0.685%) as the main amide, d-glycero-d-ido-heptose (0.532%) as the main sugar, and (4H)1,3,2-dioxaborin, 4-ethenyl-4, 6-diethyl-5-(1-methylethyl)- (0.514%) as the main metal related compound.
Conclusion: The presence of different compounds with known bioactivities can make this plant a suitable medicinal plant for supplementary medication for various diseases. Keywords: Gas chromatography/mass spectrometry, Scutellaria bornmuelleri, Methanol extract, n-Hexadecanoic acid


1.Paton A. A global taxonomic investigation of Scutellaria (Labiatae). Kew Bulletin. 1990:399-450.
2.Shen J, Li P, Liu S, Liu Q, Li Y, Sun Y, et al. Traditional uses, ten-years research progress on phytochemistry and pharmacology, and clinical studies of the genus Scutellaria. Journal of Ethnopharmacology. 2021;265:113198.
3.Gharari Z, Bagheri K, Sharafi A. Fractional analysis of dichloromethane extract of Scutellaria araxensis Grossh root and shoot by HPLC-PDA-ESI-MSn. Natural Product Research. 2021:1-5.
4.Gharari Z, Bagheri K, Derakhshani B, Sharafi A. HPLC-DAD-ESI/MSn analysis of phenolic components of Scutellaria araxensis, S. bornmuelleri and S. orientalis. Natural Product Research. 2020:1-6.
5.Gharari Z, Bagheri K, Danafar H, Sharafi A. Enhanced flavonoid production in hairy root cultures of Scutellaria bornmuelleri by elicitor induced over-expression of MYB7 and FNSП2 genes. Plant Physiology and Biochemistry. 2020;148:35-44.
6.Wang L, Chen W, Li M, Zhang F, Chen K, Chen W. A review of the ethnopharmacology, phytochemistry, pharmacology, and quality control of Scutellaria barbata D. Don. Journal of ethnopharmacology. 2020;254:112260.
7.Li-Weber M. New therapeutic aspects of flavones: the anticancer properties of Scutellaria and its main active constituents Wogonin, Baicalein and Baicalin. Cancer treatment reviews. 2009;35(1):57-68.
8.Yang B, Bai H, Sa Y, Zhu P, Liu P. Inhibiting EMT, stemness and cell cycle involved in baicalin-induced growth inhibition and apoptosis in colorectal cancer cells. Journal of Cancer. 2020;11(8):2303.
9.Singh S, Meena A, Luqman S. Baicalin mediated regulation of key signaling pathways in cancer. Pharmacological Research. 2020:105387.
10.Lu H-F, Hsueh S-C, Ho Y-T, Kao M-C, Yang J-S, Chiu T-H, et al. ROS mediates baicalin-induced apoptosis in human promyelocytic leukemia HL-60 cells through the expression of the Gadd153 and mitochondrial-dependent pathway. Anticancer research. 2007;27(1A):117-25.
11.Shieh D-E, Cheng H-Y, Yen M-H, Chiang L-C, Lin C-C. Baicalin-induced apoptosis is mediated by Bcl-2-dependent, but not p53-dependent, pathway in human leukemia cell lines. The American journal of Chinese medicine. 2006;34(02):245-61.
12.Chao J-I, Su W-C, Liu H-F. Baicalein induces cancer cell death and proliferation retardation by the inhibition of CDC2 kinase and survivin associated with opposite role of p38 mitogen-activated protein kinase and AKT. Molecular cancer therapeutics. 2007;6(11):3039-48.
13.Gharari Z, Bagheri K, Khodaeiaminjan M, Sharafi A. Potential therapeutic effects and bioavailability of wogonin, the flavone of baikal skullcap. J Nutri Med Diet Care. 2019;5(039).
14.Chen X-m, Bai Y, Zhong Y-j, Xie X-l, Long H-w, Yang Y-y, et al. Wogonin has multiple anti-cancer effects by regulating c-Myc/SKP2/Fbw7α and HDAC1/HDAC2 pathways and inducing apoptosis in human lung adenocarcinoma cell line A549. PLoS One. 2013;8(11):e79201.
15.Feng Q, Wang H, Pang J, Ji L, Han J, Wang Y, et al. Prevention of wogonin on colorectal cancer tumorigenesis by regulating p53 nuclear translocation. Frontiers in pharmacology. 2018;9:1356.
16.Wang W, Guo Q-L, You Q-D, Zhang K, Yang Y, Yu J, et al. The anticancer activities of wogonin in murine sarcoma S180 both in vitro and in vivo. Biological and Pharmaceutical Bulletin. 2006;29(6):1132-7.
17.Chen J, Cao Y, Li Y, Tang L, Yu X, Xia J. Wogonoside exerts potential anti-tumor activity against bladder cancer in vivo and in vitro via regulation of GSK3β/ERK/AKT signaling pathway. Tropical Journal of Pharmaceutical Research. 2019;18(7):1385-90.
18.Wei C, Jing J, Zhang Y, Fang L. Wogonoside inhibits prostate cancer cell growth and metastasis via regulating Wnt/β-Catenin pathway and epithelial-mesenchymal transition. Pharmacology. 2019;104(5-6):312-9.
19.Ghahreman A, Attar F. Biodiversity of plant species in Iran: Central Herbarium of Tehran University. Faculty of Science. 1999:379.
20.Zargari A. Medicinal plants: Tehran University of Medical Sciences; 1997.
21.Gharari Z, Bagheri K, Danafar H, Sharafi A. Essential oil composition of two Scutellaria species from Iran. Journal of Traditional Chinese Medical Sciences. 2019;6(3):244-53.
22.Gharari Z, Aghajanzadeh M, Sharafi A. Scutellaria orientalis subsp. Bornmuelleri: phytochemical composition and biological activities. Natural Product Research. 2021; 36:1385-1390.
23.Gharari Z, Bagheri K, Danafar H, Sharafi A. Simultaneous determination of baicalein, chrysin and wogonin in four Iranian Scutellaria species by high performance liquid chromatography. Journal of Applied Research on Medicinal and Aromatic Plants. 2020;16:100232.
24.Shapla UM, Solayman M, Alam N, Khalil MI, Gan SH. 5-Hydroxymethylfurfural (HMF) levels in honey and other food products: effects on bees and human health. Chemistry Central Journal. 2018;12(1):1-18.
25.Aparna V, Dileep KV, Mandal PK, Karthe P, Sadasivan C, Haridas M. Anti‐inflammatory property of n‐hexadecanoic acid: structural evidence and kinetic assessment. Chemical biology & drug design. 2012;80(3):434-9.
26.Patra JK, Das G, Baek K-H. Chemical composition and antioxidant and antibacterial activities of an essential oil extracted from an edible seaweed, Laminaria japonica L. Molecules. 2015;20(7):12093-113.
27.Azar AWP, Rosleine D, Faizal A, editors. Secondary metabolite profiles in the methanolic extract of Leucobryum javense isolated from tropical montane forest in West Java, Indonesia. AIP Conference Proceedings; 2019: AIP Publishing LLC.
28.Rajendrasozhan S, Moll HE, Snoussi M, Romeilah RM, Shalaby EA, Younes KM, et al. Phytochemical Screening and Antimicrobial Activity of Various Extracts of Aerial Parts of Rhanterium epapposum. Processes. 2021;9(8):1351.
29.Othman AR, Abdullah N, Ahmad S, Ismail IS, Zakaria MP. Elucidation of in-vitro anti-inflammatory bioactive compounds isolated from Jatropha curcas L. plant root. BMC complementary and alternative medicine. 2015;15(1):1-10.
30.Abubakar MN, Majinda RR. GC-MS analysis and preliminary antimicrobial activity of Albizia adianthifolia (Schumach) and Pterocarpus angolensis (DC). Medicines. 2016;3(1):3.
31.Islam MT, Ali ES, Uddin SJ, Shaw S, Islam MA, Ahmed MI, et al. Phytol: A review of biomedical activities. Food and chemical toxicology. 2018;121:82-94.
32.Swamy MK, Arumugam G, Kaur R, Ghasemzadeh A, Yusoff MM, Sinniah UR. GC-MS based metabolite profiling, antioxidant and antimicrobial properties of different solvent extracts of Malaysian Plectranthus amboinicus leaves. Evidence-Based Complementary and Alternative Medicine. 2017; 2017.
33.Fernandez M, Saenz M, Garcia M. Anti-inflammatory activity in rats and mice of phenolic acids isolated from Scrophularia frutescens. Journal of Pharmacy and Pharmacology. 1998;50(10):1183-6.
34.Rossellia S, Maggio A, Formisano C, Napolitano F, Senatore F, Spadaro V, et al. Chemical Composition and Antibacterial Activity of Extracts of Helleborus bocconei Ten. subsp. intermedius. Natural Product Communications. 2007;2(6):1934578X0700200611.
35.Dilika F, Bremner P, Meyer J. Antibacterial activity of linoleic and oleic acids isolated from Helichrysum pedunculatum: a plant used during circumcision rites. Fitoterapia. 2000;71(4):450-2.
36.McGaw L, Jäger A, Van Staden J. Isolation of antibacterial fatty acids from Schotia brachypetala. Fitoterapia. 2002;73(5):431-3.
37.Zheng CJ, Yoo J-S, Lee T-G, Cho H-Y, Kim Y-H, Kim W-G. Fatty acid synthesis is a target for antibacterial activity of unsaturated fatty acids. FEBS letters. 2005;579(23):5157-62.
38.Bortolomeazzi R, Sebastianutto N, Toniolo R, Pizzariello A. Comparative evaluation of the antioxidant capacity of smoke flavouring phenols by crocin bleaching inhibition, DPPH radical scavenging and oxidation potential. Food Chemistry. 2007;100(4):1481-9.
39.Kelly C, Jones O, Barnhart C, Lajoie C. Effect of furfural, vanillin and syringaldehyde on Candida guilliermondii growth and xylitol biosynthesis.  Biotechnology for Fuels and Chemicals: Springer; 2008. p. 615-26.
40.Fillat A, Gallardo O, Vidal T, Pastor F, Díaz P, Roncero M. Enzymatic grafting of natural phenols to flax fibres: Development of antimicrobial properties. Carbohydrate Polymers. 2012;87(1):146-52.
41.González-Sarrías A, Li L, Seeram NP. Anticancer effects of maple syrup phenolics and extracts on proliferation, apoptosis, and cell cycle arrest of human colon cells. Journal of Functional Foods. 2012;4(1):185-96.
42.Satar R, Husain Q. Applications of Celite-adsorbed white radish (Raphanus sativus) peroxidase in batch process and continuous reactor for the degradation of reactive dyes. Biochemical Engineering Journal. 2009;46(2):96-104.
43.Singh G, Capalash N, Goel R, Sharma P. A pH-stable laccase from alkali-tolerant γ-proteobacterium JB: Purification, characterization and indigo carmine degradation. Enzyme and Microbial Technology. 2007;41(6-7):794-9.
44.Lattmann E, Dunn S, Niamsanit S, Sattayasai N. Synthesis and antibacterial activities of 5-hydroxy-4-amino-2 (5H)-furanones. Bioorganic & medicinal chemistry letters. 2005;15(4):919-21.
45.Byczek-Wyrostek A, Kitel R, Rumak K, Skonieczna M, Kasprzycka A, Walczak K. Simple 2 (5H)-furanone derivatives with selective cytotoxicity towards non-small cell lung cancer cell line A549–Synthesis, structure-activity relationship and biological evaluation. European journal of medicinal chemistry. 2018;150:687-97.
46.Wu Y-C, Luo S-H, Mei W-J, Cao L, Wu H-Q, Wang Z-Y. Synthesis and biological evaluation of 4-biphenylamino-5-halo-2 (5H)-furanones as potential anticancer agents. European journal of medicinal chemistry. 2017;139:84-94.
47.Steenackers HP, Levin J, Janssens JC, De Weerdt A, Balzarini J, Vanderleyden J, et al. Structure–activity relationship of brominated 3-alkyl-5-methylene-2 (5H)-furanones and alkylmaleic anhydrides as inhibitors of Salmonella biofilm formation and quorum sensing regulated bioluminescence in Vibrio harveyi. Bioorganic & medicinal chemistry. 2010;18(14):5224-33.
48.Gondela E, Walczak KZ. Synthesis and preliminary bioactivity assays of 3, 4-dichloro-5-(ω-hydroxyalkylamino)-2 (5H)-furanones. European journal of medicinal chemistry. 2010;45(9):3993-7.
49.Hashem AI, Youssef AS, Kandeel KA, Abou-Elmagd WS. Conversion of some 2 (3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activity. European journal of medicinal chemistry. 2007;42(7):934-9.
50.Zapf S, Anke T, Sterner O. Incrustoporin, a new antibiotic from Incrustoporia carneola (Bres.) Ryv.(Basidiomycetes). Acta chemica Scandinavica (Copenhagen, Denmark: 1989). 1995;49(3):233-4.
51.Uddin MJ, Crews BC, Ghebreselasie K, Tantawy MN, Marnett LJ. [123I]-Celecoxib analogues as SPECT tracers of cyclooxygenase-2 in inflammation. ACS medicinal chemistry letters. 2011;2(2):160-4.
52.Weber V, Coudert P, Rubat C, Duroux E, Vallée-Goyet D, Gardette D, et al. Novel 4, 5-diaryl-3-hydroxy-2 (5H)-furanones as anti-oxidants and anti-inflammatory agents. Bioorganic & medicinal chemistry. 2002;10(6):1647-58.