Chemical Constituents and their Antifungal Activity from the Branch Extracts of Plumbago indica L.
Keywords:
Plumbago indica, Plumbaginaceae, Plumbagin, Antifungal Activity, Medicinal PlantAbstract
Background: Plumbago indica L. produces bioactive compounds with anti-inflammatory, antifungal, antibacterial, antiparasitic, antifertility, anti-oxidant, wound healing, anticancer and antiviral activities. The study aimed to isolate, separate and evaluate compounds’ antifungal activities from the branches of P. indica.
Methods: The crude dichloromethane and ethyl acetate extracts of branches of P. indica were individually separated and purified by various column chromatographic techniques. The structures were elucidated using spectroscopic techniques. The isolated compounds were evaluated for antifungal activity against Aspergillus flavus and Talaromyces marneffei.
Results: Plumbagin (1), β-sitosterol (2), maritinone (3) and –7´ - biplumbagin (4) were isolated from dichloromethane extract, while cis-isoshinanolone (5) and trans-isoshinanolone (6) were isolated from the ethyl acetate extract of the branches of P. indica. Compound 1 antifungal activity against A. flavus and T. marneffei with zones of inhibition of 40.0 and 70.0 mm (at 1.0 mg/disc). Compound 5 exhibited antifungal activity against A. flavus and T. marneffei with zones of inhibition of 7.0 and 12.0 mm, respectively (at concentrations of 1.0 and 0.25 mg/ disc), and compound 6 showed activity against A. flavus and T. marneffei with zones of inhibition of 7.0 and 10.0 mm, respectively (at concentrations of 1.0 and 0.25 mg/disc). Compounds 3, 4 and 6 were obtained from this plant for the first time.
Conclusions: Six constituents, plumbagin (1), β-sitosterol (2), maritinone (3), 7–7´-biplumbagin (4), cis-isoshinanolone (5) and trans-isoshinanolone (6), were isolated from the branches of P. indica. From these results, plumbagin can be considered the active chemical constituent responsible for the antifungal activity against A. flavus and T. marneffei. This study is the first to report the isolation of compounds 3, 4 and 6 from P. indica and the antifungal activity of compounds 1, 5 and 6 against A. flavus and T. marneffei.
References
Priyanjani HASA, Senarath RMUS, Senarath WTPSK, Munasinghe MLAMS. Propagation,Phytochemistry and Pharmacology of Plumbago indica - A Review. J. Pharm. Res. Int., 2021;33(42B):188-202. https://doi.org/10.9734/jpri/2021/v33i42B32439
Thitiorul S, Ratanavalachai T, Tanuchit S, Itharat A, Sakpakdeejaroen I. Genotoxicity and interference with cell cycle activities by an ethanolic extract from Thai Plumbago indica roots in human lymphocytes in vitro. Asian Pac. J. of Cancer Prev. 2013;14(4): 2487- 2490. https://doi.org/10.7314/APJCP.2013.14.4.2487 PMid:23725161
Ittiyavirah SP, Jobin KV, Jissa MS, Jomy M, Josmi TJ, Littin B. Anti-inflammatory and analgesic activities of Plumbago capensis and Plumbago indica. Adv. Pharmacol. Toxicol. 2012;13(1): 47-52.
Rondeau G, Abedinpour P, Chrastina A, Pelayo J, Borgstrom P, Welsh J. Differential gene expression induced by anti-cancer agent plumbagin is mediated by androgen receptor in prostate cancer cells. Sci. Rep. 2018; 8(1):2694. https://doi.org/10.1038/s41598-018-20451-9 PMid:29426892 PMCid:PMC5807367
Cao Y, Yin X, Jia Y, Liu B, Wu S, Shang M. Plumbagin, a natural naphthoquinone, inhibits the growth of esophageal squamous cell carcinoma cells through inactivation of STAT3. Int. J. Mol. Med. 2018;42(3): 1569- 1576. https://doi.org/10.3892/ijmm.2018.3722
Malaiyandia J, Anandapadmanabanb G, Perumalsamyc H, Kilankajaed A, Chellappanf DK, Duag K, et al. Plumbagin from two Plumbago species inhibits the growth of stomach and breast cancer cell lines. Ind. Crops. Prod. 2020;146: 112147. https://doi.org/10.1016/j.indcrop.2020.112332
Dissanayake DMIH, Perera DDBD, Keerthirathna LR, Heendeniya S, Anderson RJ, Williams DE, et al. Antimicrobial activity of Plumbago indica and ligand screening of plumbagin against methicillin-resistant Staphylococcus aureus. J Biomol. Struct. Dyn. 2022;40(7): 3273-3284. https://doi.org/10.1080/07391102.2020.1846622 PMid:33213303
Sil SK. A review on pharmacological profiles of Plumbago indica L. and P. zeylanica L. Ind. J. Physiol. Allied Sci. 2015;69(3): 83-89.
Panyaphu K, Sirisa-ard P, Ubol PN, Nathakarnkitkul S, Chansakaow S, On TV. Phytochemical, antioxidant and antibacterial activities of medicinal plants used in Northern Thailand as postpartum herbal bath recipes by the Mien (Yao) community. Phytopharmacology. 2012;2(1): 92-105.
Eldhose B, Notario V, Latha MS. Evaluation of phytochemical constituents and In vitro antioxidant activities of Plumbago indica root extract. J. Pharmacogn. Phytochem. 2013;2(4): 157-161.
Ibrahim M, Baura J, Islam T, Homa Z, Chowdhury M, Hossain A, et al. Preliminary phytochemical and pharmacological investigations of Alpinia conchigera Griff. and Plumbago indica L. Bangla. Pharma. J. 2012;15(2):153-157. https://doi.org/10.3329/bpj.v15i2.12581
Yu B, Zhu X, Yang X, Jin L, Xu J, Ma T, et al. Plumbagin prevents secretory diarrhea by inhibiting CaCC and CFTR channel activities. Front. Pharmacol. 2019;10: 1181. https://doi.org/10.3389/fphar.2019.01181 PMid:31649543 PMCid:PMC6795057
Savadi RV, Alagawadi KR. Antifertility activity of ethanolic extracts of Plumbago indica and Aerva lanata on albino rats. Int. J. Green Pharm. 2009;3: 230-233. https://doi.org/10.4103/0973-8258.56281
Dasgupta GM, Thangamani D, Thapliyal M, Yasodha R, Gurumurthi K. Purification of a 20 KDa antifungal protein from Plumbago capensis a medicinal plant. J. Med. Aromat. Plant Sci. 2002;24: 16-18.
Saraswathy A, Chandran RVP, Manohar BM, Vairamuthu S. Wound healing activity of the chloroform extract of Plumbago rosea Linn. and Plumbagin. Nat. Prod. Sci. 2006;12(1): 50-54.
Sujin JKT, Balavigneswaran CK, Prakash S, Natheer HY, Srinivasakumar KP. Excision wound healing and antioxidant activity of different root extracts of Plumbago indica. Med. Plant Res. 2013;3(3): 13-19. https://doi.org/10.5376/mpr.2013.03.0003
Rafa ZT, Ashrafudoulla M, Fuad F, Islam R, Hasan M, Kafi MAH, et al. Phytochemical and pharmacological investigation of Plumbago indica L. J. Med. Plants Stud. 2016;4(2): 115-118.
Bansod S, Rai M. Antifungal activity of essential oils from Indian medicinal plants against human pathogenic Aspergillus fumigatus and A. niger. World J. Med. Sci. 2008;3(2):81-88.
Liu Y, Cai Y, He C, Chen M, Li H. Anticancer properties and pharmaceutical applications of plumbagin: A review. Am. J. Chin. Med. 2017;45(3): 423-441. https://doi.org/10.1142/S0192415X17500264 PMid:28359198
Guan HH, Huang YH, Lin ES, Chen CJ, Huang CY. Plumbagin, a natural product with potent anticancer activities, binds to and inhibits dihydroorotase, a key enzyme in pyrimidine biosynthesis. Int. J. Mol. Sci. 2021;22(13): 6861. https://doi.org/10.3390/ijms22136861 PMid:34202294 PMCid:PMC8267945
Gu JQ, Graf TN, Lee D, Chai HB, Mi Q, Kardono LBS, et al. Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima Collected in two geographical locations in Indonesia. J. Nat. Prod., 2004; 67(7): 1156-1161. https://doi.org/10.1021/np040027m PMid:15270571
Salae AW, Karalai C, Ponglimanont C, KanjanaOpas AK, Yuenyongsawad S. Naphthalene derivatives from Diospyros wallichii. Can. J. Chem. 2010;88: 922-927. https://doi.org/10.1139/V10-084
Bringmann G, Münchbach M, Messer K, Koppler D, Michel M, Schupp O, et al. Cis- and trans-isoshinanolone from Dioncophyllum thollonii: absolute configuration of two 'known', wide-spread natural products. Phytochemistry. 1999; 51(5): 693-699. https://doi.org/10.1016/S0031-9422(99)00080-1
Jetty A, Subhakar C, Rajagopal D, Jetty M, Subramanyam M, Murthy MM. Antimicrobial activities of neo- and 1-epineoisoshinanolones from Plumbago zeylanica roots. Pharm. Biol. 2010;48(9): 1007-1011. https://doi.org/10.3109/13880200903433760 PMid:20731552
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2022 Chulabhorn Royal Academy
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
บทความที่ได้รับการตีพิมพ์เป็นลิขสิทธิ์ของราชวิทยาลัยจุฬาภรณ์
ข้อความที่ปรากฏในบทความแต่ละเรื่องในวารสารวิชาการเล่มนี้เป็นความคิดเห็นส่วนตัวของผู้เขียนแต่ละท่านไม่เกี่ยวข้องกับราชวิทยาลัยจุฬาภรณ์ และคณาจารย์ท่านอื่น ในราชวิทยาลัยฯ แต่อย่างใด ความรับผิดชอบองค์ประกอบทั้งหมดของบทความแต่ละเรื่องเป็นของผู้เขียนแต่ละท่าน หากมีความผิดพลาดใด ๆ ผู้เขียนแต่ละท่านจะรับผิดชอบบทความของตนเองแต่ผู้เดียว
