Phytochemical Analysis of Volatile and Non-volatile Fractions, Antioxidant, and Anti-Cancer Activities of Dracocephalum polychaetum and Dracocephalum kotschyi

Document Type : Research Articles

Authors

• Marzieh Taghizadeh ¹
• Sara Soltanian ²
• Nahid Nasibi ²

¹ Department of Plant and Animal Biology, Faculty of Biological Science and Technology, University of Isfahan, Isfahan, Iran

² Department of Biology, Faculty of Science, Shahid Bahonar University of Kerman, Kerman, Iran

https://doi.org/10.22067/jcmr.2022.75035.1031

Abstract

The present study was conducted to determine the volatile and non-volatile fractions and the antioxidant and anti-cancer activities of ethanolic extracts of Dracocephalum polychaetum and D. kotschyi. The volatile and non-volatile fractions were investigated by gas chromatography-mass spectrometry (GC-MS) and high-performance liquid chromatography (HPLC). The cytotoxicity effect of two ethanol extracts and the major phenolic components has been evaluated on breast and colon cancer cells by the MMT assay. GC-MS of the essential oils identified about 50 compounds, and perillylaldehyde and D-limonene were the main constituents in the essential oils of the two species. Moreover, high-performance liquid chromatography- Diode array detector analysis demonstrated that the ethanolic extract of  D. polychaetum and D. kotschyi were the source of phenolic compounds such as rosmarinic acid, protocatechuic acid, naringin, apigenin, syringic acid, epicatechin, chlorogenic acid, thymol, carvacrol, rutin, p-coumaric acid, gallic acid, benzoic acid, cinnamic acid, resorcinol, quercetin, salicylic acid, 4-hydroxybenzoic acid, and ferulic acid. Rosmarinic acid and thymol were the main predominant phenolic constituents in D. kotschyi and D. polychaetum ethanolic extracts. The cytotoxicity effect of D. kotschyi and D. polychaetum ethanol extracts and the major phenolic components including rosmarinic acid, thymol, apigenin, quercetin, and nariginin has been evaluated on breast and colon cancer cells by MMT assay and results indicated IC₅₀ values in the range of 90 to 140 (µg.ml^-1) after 48 hours of treatment with ethanol extracts. Among phenolic components, thymol caused the lowest cell viability and Narengin showed the lowest anti-proliferative activity. Both extracts also showed antioxidant activity using DPPH assay. The findings of this research suggest that the Dracocephalum have precious bioactive and natural compounds with significant antioxidant and in vitro anti-cancer activities.
 

Keywords

• Anti-cancer activity
• Antioxidant activity
• Essential oil
• Phenolic compounds

20.1001.1.20089147.2022.14.1.2.2

References

Adams RP. (2007) Identification of Essential Oil Components by Gas Chromatography/mass Spectrometry: Allured Publishing Corporation Carol Stream, IL

Apostolou A., Stagos D., Galitsiou E., Spyrou A., Haroutounian S., Portesis N., et al. (2013). Assessment of polyphenolic content, antioxidant activity, protection against ROS-induced DNA damage and anti-cancer activity of Vitis vinifera stem extracts. Food and chemical toxicology 61:60-68.

Burits M. and Bucar F. (2000) Antioxidant activity of Nigella sativa essential oil. Phytotherapy research 14:323-328.

Dias M. I., Sousa M. J., Alves R. C. and Ferreira I. C. (2016) Exploring plant tissue culture to improve the production of phenolic compounds: A review. Industrial crops and products 82:9-22.

Dong J., Ma X., Wei Q., Peng S. and Zhang S. (2011) Effects of growing location on the contents of secondary metabolites in the leaves of four selected superior clones of Eucommia ulmoides. Industrial Crops and Products 34:1607-1614.

Doosti M. H., Ahmadi K. and Fasihi-Ramandi M. (2018) The effect of ethanolic extract of Thymus kotschyanus on cancer cell growth in vitro and depression-like behavior in the mouse. Journal of traditional and complementary medicine 8:89-94.

Faghihinia L., Monajjemi R. and Ranjbar M. (2015) Cytotoxic and antioxidant effects of methanol, hexane, chloroform and aqueous extracts of Dracocephalum kotschyi aerial parts on MDAMB-231 cell line. Journal of Biodiversity and Environmental Sciences 6:334-340.

Falcone Ferreyra ML, Rius, S., Casati, P. 2012. Flavonoids: biosynthesis, biological functions, and biotechnological applications. Frontiers in Plant Science, 3:222

Fallah A. and Hosseini Cici S. (2020) Alteration in essential oil yield and compositions of multi-cut Dracocephalum polychaetum grown under different fertilization methods. International Journal of Horticultural Science and Technology 7:13-26.

Fallah S., Mouguee S., Rostaei M., Adavi Z. and Lorigooini Z. (2020) Chemical compositions and antioxidant activity of essential oil of wild and cultivated Dracocephalum kotschyi grown in different ecosystems: A comparative study. Industrial Crops and Products 143:111885.

Fattahi M., Bonfill M., Fattahi B., Torras-Claveria L., Sefidkon F., Cusido R. M. and Palazon J. (2016) Secondary metabolites profiling of Dracocephalum kotschyi Boiss at three phenological stages using uni-and multivariate methods. Journal of Applied Research on Medicinal and Aromatic Plants 3:177-185.

Fattahi M., Nazeri V., Torras-Claveria L., Sefidkon F., Cusido R. M., Zamani Z. and Palazon J. (2013) Identification and quantification of leaf surface flavonoids in wild-growing populations of Dracocephalum kotschyi by LC–DAD–ESI-MS. Food chemistry 141:139-146.

Golkar P. and Moattar F. (2019) Essential Oil Composition, Bioactive Compounds, and Antioxidant Activities in Iberis amara L. Natural Product Communications DOI: 10.1177/1934578X19846355.

Golkar P., Taghizadeh M. and Jalali S. A. H. (2019) Determination of phenolic compounds, antioxidant and anti-cancer activity of Chrozophora tinctoria accessions collected from different regions of Iran. Journal of food biochemistry 43:e13036.

Hara M., Oki K., Hoshino K.and Kuboi T. (2003) Enhancement of anthocyanin biosynthesis by sugar in radish (Raphanus sativus) hypocotyl. Plant Science 164:259-265.

Jaakola L. and Hohtola A. (2010) Effect of latitude on flavonoid biosynthesis in plants. Plant, cell & environment 33:1239-1247.

Jahaniani F., Ebrahimi S. A., Rahbar-Roshandel N, and Mahmoudian M. (2005) Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent. Phytochemistry 66:1581-1592.

Kamali M., Khosroyar S., Kamali H., Sani T. A and Mohammadi A. (2016) Phytochemical screening and evaluation of antioxidant activities of Dracocephalum kotschyi and determination of its luteolin content. Avicenna journal of phytomedicine 6:425.

Kchaou W., Abbès F., Mansour R. B., Blecker C., Attia H. and Besbes S. (2016) Phenolic profile, antibacterial and cytotoxic properties of second grade date extract from Tunisian cultivars (Phoenix dactylifera L.). Food chemistry 194:1048-1055.

Khodaei M., Amanzadeh Y., Faramarzi M. A. and Hamedani M. P. (2018) Chemical analysis and anti-bacterial effect of essential oils from three different species of Dracocephalum in Iran. American Journal of Essential Oils and Natural Products 6:31-34.

Miliauskas G., Venskutonis P. and Van Beek T. (2004) Screening of radical scavenging activity of some medicinal and aromatic plant extracts. Food chemistry 85:231-237.

Mirzania F. and Farimani M. M. (2018) Biochemical evaluation of antioxidant activity, phenol and flavonoid contents of Dracocephalum kotschyi Boiss extracts obtained with different solvents. Avicenna Journal of Phytomedicine 6(4): 425–433.

Penuelas J. and Llusià J. (1997) Effects of carbon dioxide, water supply, and seasonality on terpene content and emission by Rosmarinus officinalis. Journal of Chemical Ecology 23:979-993.

Pouraboli I., Nazari S., Sabet N., Sharififar F. and Jafari M. (2016) Antidiabetic, antioxidant, and antilipid peroxidative activities of Dracocephalum polychaetum shoot extract in streptozotocin-induced diabetic rats: In vivo and in vitro studies. Pharmaceutical biology 54:272-278.

Sani T. A., Mohammadpour E., Mohammadi A., Memariani T., Yazdi M. V., Rezaee R., et al. (2017) Cytotoxic and apoptogenic properties of Dracocephalum kotschyi aerial part different fractions on calu-6 and mehr-80 lung cancer cell lines. Farmacia 65:189-199.

Sharifi B., Goli S. A. H. and Maghsoudlou Y. (2017) Antioxidant activity and chemical composition of the methanolic extract and related fractions of Dracocephalum kotschyi leaves using liquid chromatography–tandem mass spectrometry. Industrial crops and products 104:111-119.

Sobral M. V., Xavier A. L., Lima T. C., de Sousa D. P. (2014) Antitumor activity of monoterpenes found in essential oils. The Scientific World Journal doi.org/10.1155/2014/953451.

Zhang Y., Hu M., Liu L., Cheng X-L., Cai J., Zhou J., Wang T. (2018) Anti-cancer effects of Rosmarinic acid in OVCAR-3 ovarian cancer cells are mediated via induction of apoptosis, suppression of cell migration and modulation of lncRNA MALAT-1 expression. J BUON 23:763-768.