IDENTIFICATION OF ANTHRAQUINONES FROM CASSIA TORA L. SEEDS AND ANTIFUNGAL ACTIVITY

Main Article Content

Laksana Charoenchai
Natawat Chankana

Abstract

Anthraquinones are a major group of active compounds found in Cassia plants. Cassia tora L. was a medicinal plant and its seeds and leaves have been used as laxative. C. tora seed extracts have been reported for antibacterial and antifungal activities. This study aimed to identify anthraquinones from C. tora seeds and determined antifungal activity. C. tora seeds were extracted with 80%ethanol and partial purified with column chromatography. HPLC with RP C18 column and mobile phase composition of 0.01% phosphoric acid in water and methanol were used for analysis. The antifungal activity was tested against Trichophyton mentagrophytes using broth microdilution assay. Results showed that four anthraquinone compounds were identified including aloe-emodin, emodin, chrysophanol and physcion. Total anthraquionone of crude 80% ethanolic extract was 55.60 %w/w and those of 95% ethanolic and acetone subfractions were 10.10-51.77% w/w and 54.88-70.57 %w/w, respectively. The 95%ethanolic subfraction inhibited T. mentagrophytes with a minimal concentration (MIC) of 125 and a minimal fungicidal concentration (MFC) of 1,000 μg/mL, respectively compared with ketoconazole (MIC and MFC = 20 μg/mL). Partial purified acetone fraction contained main anthraquinones including chrysophanol, physcion and emodin while 1-desmethylaurantio-obtusin and aurantio-obtusin were major compounds in ethanolic subfraction. These subfractions inhibited T. mentagrophyte about 4 to 8-folded higher than the crude extract. This extract would be useful for development of antifungal product.

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How to Cite
1.
Charoenchai L, Chankana N. IDENTIFICATION OF ANTHRAQUINONES FROM CASSIA TORA L. SEEDS AND ANTIFUNGAL ACTIVITY. Interprof J Health Sci [Internet]. 2023 Oct. 5 [cited 2024 Nov. 22];16(1):60-9. Available from: https://li05.tci-thaijo.org/index.php/IJHS/article/view/185
Section
Research Articles

References

Acharya TK, Chatterjee, IB. 1975. Isolation of chrysophanic acid-9-anthrone, the major antifungal principle of Cassia tora. Lloydia. 38(3): 218-220.

Agarwal SK, Singh SS, Verma S, Kumar S. 2000. Antifungal activity of anthraquinone derivatives from Rheum emodi. J Ethnopharmacology. 72: 43-46.

Choudhary M, Gulia Y, Nitesh. 2011. Cassia tora: Its chemistry, medicinal uses and pharmacology. Pharmacologyonline. 3: 78-96.

Dave H, Ledwani L. 2012. A review on anthraquinones isolated from Cassia species and their applications. Indian Journal of Natural Products and Resources. 3(3): 291-319.

DiaionTM Technical Manual: Synthetic adsorbents DiaionTM & SepabeadsTM.

Hatano T, Uebayashi H, Ito H, Shiota S, Tsuchiya T, Yoshida T. 1999. Phenolic constituents of cassis seeds and antibacterial effect of some naphthalenes and anthraquinones on methicillin-resistant Staphylococcus aureus. Chem. Pharm. Bull. 47(8): 1121-1127.

Jia-li Z, Zhi-yong X, Xiao-fei J, Xin-xia C, Mei-cun Y. 2008. Determination of anthraquinones in different compatibility of Dahuang Huanglian Xiexin decoction by HPLC. Mode Tradit Chin Med Mater Med. 10(4): 61-64.

Lee N-H, Lee S-M, Song D-H, Yang J-Y, Lee H-S. 2013. Antimicrobial effect of emodin isolated from Cassia tora Linn. seeds against food-borne bacteria. J. Appl. Biol. Chem. 187-189.

Ministry of Public Health. 2016. Thai Herbal Pharmacopoeia. Chumhet Thai. The Agricultural Co-operative Federation of Thailand. Ltd. Bangkok, Thailand. 77-84.

Mukherjee PK, Saha K, Saha BP, Pal M. 1996. Antifungal activities of the leaf extract of Cassia tora Linn. (Fam. Leguminosae). Phytotherapy Research. 10: 521-522.

Panichayupakaranant P, Sakunpak A, Sakunphueak A. 2009. Quantitative HPLC determination and extraction of anthraquinones in Senna alata leaves. J Chromatographic Science. 47. 197-200.

Patil UK, Jain S. 2010. Phytochemical and pharmacological profile of Cassia tora Linn – An overview. Indian J of Natural Products and Resources. 1(4): 430-437.

Pawar HA, D’mello PM. 2011. Cassia tora Linn.: An overview. International Journal of Pharmaceutical Sciences and Research. 2(9): 2286-2291.

Pongpaichit S, Pujenjob N, Rukachaisirikul V, Ongsakul M. Antifungal activity from leaf extracts of Cassia alata L., Cassia fistula L. and Cassia tora L. Songklanakarin J. Sci. Technol. 26(5): 741-748.

Sakunpak A, Sirikatitham A, Panichayupakaranant P. 2009. Preparation of anthraquinone high yielding Senna alata extract and its stability. Pharmaceutical Biology. 47(3): 236-241.

Sakunphueak A, Panichyupakkaranant P, Kaewnam W. 2012. Simultaneous determination of anthraquinone distribution in Cassia tora using high performance liquid chromatography. Planta Medica.

Sakulpanich A, Kritsanapan W. 2008. Extraction method for high content of anthraquinones from Cassia fistula pods. J Health Research. 22(4): 167-172.

Sakulpanich A, Kritsanapan W. 2009. Determination of anthraquinone glycoside content in Cassia fistula leaf extracts for alternative source of laxative drug. Int. J. Biomed and Pharm Sci. 3(1): 42-45.

Wuthi-udomlert M, Kupittayanant P, Gritsanapan W. 2010. In vitro evaluation of antifungal activity of anthraquinone derivatives of Senna alata. J Health Research. 24(3): 117-122.

Zhu L, Yu S, Zeng X, Fu X, Zhao M. 2008. Preaparative separation and purification of five anthraquinones from Cassia tora L. by high-speed counter-current chromatography. Separation and Purification Technology. 63: 665-669.