Biological Activities of Extracts and Isolated Calotropin from Gomphocarpus purpurascens Leaves: A Computational and Experimental Study

Yıl 2024, Cilt: 11 Sayı: 4, 1377 - 1386

Tsegu Kiros , Seid Mohammed , Aman Dekebo , Yadessa Melaku

https://doi.org/10.18596/jotcsa.1393500

Öz

Gomphocarpus purpurascens A.Richs. (sub-family: Asclepiadaceae, family: Apocynaceae) is an endemic plant in Ethiopia and Eritrea. The chromatographic fractionation of the chloroform:methanol (1:1) leaf extract resulted in the isolation of a cardenolide-type compound named calotropin. Its structure was confirmed based on the 1D-NMR (1H, 13C, and DEPT-135) spectral data along with reported work. This is the first report on the isolation of calotropin from the leaves of G. purpurascens. The n-hexane extract displayed better antibacterial activity against E. coli and P. aeruginosa (8.1 ± 0.0 to 10.8 ± 0.1 mm) up to 12,500 μg/mL concentration. Generally, all the extracts and the isolated compound, calotropin, showed better antibacterial activity against the P. aeruginosa strain than chloramphenicol (7.1 ± 0.2 to 7.3 ± 0.5 mm). The tested chloroform: methanol (1:1) extract indicated a weak antifungal activity against C. albicans compared to ketoconazole 10 µg/disc (17.67 ± 2.52 mm). On the contrary, all the extracts were found to have a good DPPH radical scavenging activity (IC50 values, 1.1-2.7 µg/mL) comparable to ascorbic acid (1.0 µg/mL). The isolated calotropin exhibited a stronger binding capacity (-10.3 kcal/mol) against the P. aeruginosa PqsA (5OE3) protein model than chloramphenicol (-7.0 kcal/mol). This compound was also found to violate Lipinski’s rules of five (with a molecular weight > 500 g/mol) and showed immunotoxicity and cytotoxicity properties. Given that this is a preliminary report, further biochemical investigations would be needed on this G. purpurascens plant to identify additional phytoconstituents with superior efficacy.

Anahtar Kelimeler

Gomphocarpus purpurascens, Asclepiadaceae, Apocynaceae, calotropin, biological activities, docking analysis

Kaynakça

• 1. Hedberg I. Flora of ethiopia and eritrea. In: The Biodiversity of african plants [Internet]. Dordrecht: Springer Netherlands; 1996. p. 802–4. Available from: <URL>.
• 2. Belayneh A, Bussa NF. Ethnomedicinal plants used to treat human ailments in the prehistoric place of Harla and Dengego valleys, eastern Ethiopia. J Ethnobiol Ethnomed [Internet]. 2014 Dec 5;10(1):18. Available from: <URL>.
• 3. Deng L, Costa F, Blake KJ, Choi S, Chandrabalan A, Yousuf MS, et al. S. aureus drives itch and scratch-induced skin damage through a V8 protease-PAR1 axis. Cell [Internet]. 2023 Nov 22;186(24):5375-5393.e25. Available from: <URL>.
• 4. Asfaw M, Mulaw A. Evaluation of topical antifungal activity of Gomphocarpus purpurascens A. rich leaves and stems extracts against epizootic lymphangitis. Int J Microbiol Res [Internet]. 2018;9(2):19–25. Available from: <URL>.
• 5. Ayanaw MA, Yesuf JS, Birru EM. Evaluation of analgesic and anti-inflammatory activities of methanolic leaf and root extracts of Gomphocarpus purpurascens A. Rich (Asclepiadaceae) in mice. J Exp Pharmacol [Internet]. 2023 Jan 1;Volume 15:1–11. Available from: <URL>.
• 6. Miseganaw D, Sahile Samuel, Negash W. In vitro antimicrobial effects of Gomphocarpus purpurascens a. rich against standard and clinically isolatedmicroorganisms. Glob Sci Journals [Internet]. 2019;7(6):121–36. Available from: <URL>.
• 7. Asfaw M, Mitku F, Mulaw A. Laboratory evaluation of antibacterial activity of Gomphocarpus purpurascens A. Rich leaves and stems extracts against Escherichia coli. Int J Microbiol Res [Internet]. 2018;9(1):16–8. Available from: <URL>.
• 8. Gammatantrawet N, Nguyễn CT, Susawaengsup C, Ramli ANM, Tongkoom K, Chatsungnoen T, et al. Phytochemistry of medicinal herbs belongs to asclepiadaceae family for therapeutic applications: A critical review. Mol Biotechnol [Internet]. 2024 Mar 20;Article in Press:1–25. Available from: <URL>.
• 9. Marzouk AM, Osman SM, Gohar AA. A new pregnane glycoside from Gomphocarpus fruticosus growing in Egypt. Nat Prod Res [Internet]. 2016 May 2;30(9):1060–7. Available from: <URL>.
• 10. Green PWC, Veitch NC, Stevenson PC, Simmonds MSJ. Cardenolides from Gomphocarpus sinaicus and Pergularia tomentosa (Apocynaceae: Asclepiadoideae) deter the feeding of Spodoptera littoralis. Arthropod Plant Interact [Internet]. 2011 Sep 6;5(3):219–25. Available from: <URL>.
• 11. Latif Z, Gray A. Natural products isolation. Second edition. Totowa, New Jersey: Humana Press inc.; 2006.
• 12. Singh VK. Selected Indian Folk medicinal claims and their relevance in primary health care programme. Glimpses Plant Res. 1993;10:147–52.
• 13. Kunert O, Rao BVA, Babu GS, Padmavathi M, Kumar BR, Alex RM, et al. Novel steroidal glycosides from two Indian Caralluma species, C. stalagmifera and C. indica. Helv Chim Acta [Internet]. 2006 Feb 21;89(2):201–9. Available from: <URL>.
• 14. McCartney JE, Collee JG, Mackie TJ. Practical medical microbiology. Charchil Livingstone; 1989.
• 15. Kiros T, Eswaramoorthy R, Mohammed S, Dekebo A, Melaku Y. Compounds with antibacterial and antioxidant activities from Cadia purpurea. Nat Prod Res [Internet]. 2023 Aug 18;37(16):2672–80. Available from: <URL>.
• 16. Kiros T, Eswaramoorthy R, Melaku Y, Dekebo A. In vitro antibacterial and antioxidant activities and molecular docking analysis of phytochemicals from Cadia purpurea roots. Mu J, editor. J Trop Med [Internet]. 2022 Feb 24;2022(1):1–13. Available from: <URL>.
• 17. Khorasani Esmaeili A, Mat Taha R, Mohajer S, Banisalam B. Antioxidant activity and total phenolic and flavonoid content of various solvent extracts from in vivo and in vitro grown Trifolium pratense L. (Red Clover). Biomed Res Int [Internet]. 2015 Jan 1;2015(1):1–11. Available from: <URL>.