Unlocking the phytochemicals in unopened pitcher fluids of Nepenthes khasiana -a GC–MS study

Abstract

Background: The pitcher plant, Nepenthes khasiana is utilized by several indigenous groups in Meghalaya, India owing to its medicinal properties. Due to their therapeutic qualities, a pioneer work was undertaken where the GC–MS technique was used to detect and identify the phytochemical substances present in the unopened pitcher fluids of N. khasiana.

Materials and methods: Sample preparation and extraction of the methanol fraction of N. khasiana pitcher fluid were done following standard methods and exposed to GC–MS for phytochemical profiling.

Results: The GC–MS study revealed 22 compounds in total, each of which had different phytochemical properties. The metabolites present were coronavirus inhibitors, antioxidants, antimicrobials, cure urolithiasis, hypocholesterolemic, and can cure cancer. Lipinski’s Rule of 5 also depicted that 19 compounds of 22 have the potential to make active oral drugs for humans.

Conclusion: The metabolites present in pitcher fluids could be used in drug formulation in pharmacology. Even, the fluids can be used as raw medicine for poor people owing to their medicinal properties as depicted in GC–MS however, further research on quantitative and qualitative investigation, its clinical trial on animals along with cytotoxic study are required for a concrete conclusion.

Keywords

Pitcher plant / Nepenthes khasiana / GC–MS / Phytochemical properties / Lipinski’s rule of 5 / Coronavirus inhibitor

References

[1] VedD, SahaD, HaridsanK, et al. Nepenthes Khasiana. SSC-IUCN Red List of Threatened Species. IUCN;2015. https://doi.org/10.2305/IUCN.UK.2015-2.RLTS.T48992883A49009685.en.

[2] MaoAA, Kharbuli P. Distribution and status of Nepenthes khasiana Hook. f., a rare endemic pitcher plant of Meghalaya, India. Phytotaxonomy. 2002;2:77–83.

[3] MominMA, BellahSF, RahmanSM, et al. Phytopharmacological evaluation of ethanol extract of Sida cordifolia L. roots. Asian Pac J Trop Biomed. 2014;4(1):18–24.

[4] DeviSP, Kumarian S, Sharma PhR, KhoyumthemP, et al. Nepenthes khasiana Hook f., an endangered tropical pitcher plant of India. Indian J Tradit Knowl. 2019;18(1):68–75.

[5] BordoloiRPM. The Pitcher Plant Nepenthes Khasiana. Guwahati, Assam: Sreeguru Press;1977.

[6] JosephJ, JosephKM. Insectivorous Plants of Khasi and Jaintia Hills, Meghalaya, India: A Preliminary Survey. Kolkata, India: Botanical Survey of India;1986.

[7] BeheraKK, SahooS, MohapatraPN. Medicinal plant resources for bioprospecting and drug development in tribal rich district of Orissa, India. Ethnobot Leafl. 2007;11:106–112.

[8] KumarYK, Haridasan S, RaoRR. Ethnobotanical notes on certain medicinal plants among some Garo people around Balphakram Sanctuary in Meghalaya. Bull Bot Surv India. 1980;22(1–4):161–165. https://doi.org/10.20324/nelumbo%2Fv22%2F1980%2F75417.

[9] KharkongorP, JosephJ. Folklore medicobotany of rural Khasi and Jaintia tribes in Meghalaya. In: Jain SK, ed. Glimpses of Indian Ethnobotany. New Delhi: Oxford and IBH;1981:115.

[10] SinghJN, MudgalV. Studies on habitat conditions of a few plants species of medicinal values of Nokrek Biosphere Reserve, Meghalaya. J Non-Timber Forest Prod. 1999;6(3/4):192–198.

[11] DeviR, Venugopal N. The status of insectivorous plants in North-East India: their uses and conservation. J Swamy Bot Club. 2006;23(1-4):75–80.

[12] ShilD, Mohanty J, DasT, et al. Protective role of pitcher of Nepenthes khasiana Hook against dexamethazone induced hyperlipidemia and insulin resistance in rats. Int J Res Pharm. 2010;1(2):195–198.

[13] GhoshD, GhoshS. India’s only pitcher plant in peril. Sci Rep. 2012;49(6):53–56.

[14] SanusiSB, Abu Bakar MF, MohamedM, et al. Ethnobotanical, phytochemical, and pharmacological properties of Nepenthes species: a review. Asian J Pharmaceut Clin Res. 2017;10(11):16–19.

[15] MahomoodallyMF. Traditional medicines in Africa: an appraisal of ten potent African medicinal plants. Evid Based Complementary Altern Med. 2013;617459.

[16] PatelDK. Plant as a source of medicine. Med Aromatic Plants. 2015;S3:1.

[17] AtanasovAG, Waltenberger B, Pferschy-WenzigEM, et al. Discovery and resupply of pharmacologically active plant-derived natural products: a review. Biotechnol Adv. 2015;33(8):1582–1614.

[18] FaridMM, Hussein SR, IbrahimLF, et al. Cytotoxic activity and phytochemical analysis of Arum palaestinum Boiss. Asian Pac J Trop Biomed. 2015;5(11):944–947.

[19] GuoF, FengL, HuangC, et al. Phenylflavone derivatives from Broussonetia papyrifera inhibit the growth of breast cancer cells in vitro and in vivo. Phytochem Lett. 2013;6(3):331–336.

[20] MominKC, MehraTS, DobhalS, et al. Status of Nephenthes khasiana Hook. f. (Pitcher plant) in Meghalaya: a review. J Pharmacogn Phytochem. 2018;7(3):353–358.

[21] UmaG, Balasubramaniam V. GC-MS analysis of Nothapodytes nimmoniana, Mabberly leaves. J Chem Pharm. 2012;4(9):4417–4419.

[22] HethelyiE, Tetenyi P, DabiE, et al. The role of mass spectrometry in medicinal plant research. Biomed Environ Mass Spectrom. 1987;14(11):627–632.

[23] RazackS, KumarKH, NallamuthuI, et al. Antioxidant, biomolecule oxidation protective activities of Nardostachys jatamansi DC and its phytochemical analysis by RP-HPLC and GC-MS. Antioxidants. 2015;4(1):185–203.

[24] BlighEG, DyerWJ. A rapid method of total lipid extraction and purification. Can J Biochem Physiol. 1959;37(8):911–917.

[25] ShyurLF, LiuCP, ChienSC. Metabolomics in herbal medicine research. Handbook Plant Metabolomics. 2013;155–174.

[26] RosliMAF, AzizanKA, BaharumSN, et al. Mass spectrometry data of metabolomics analysis of Nepenthes pitchers. Data Brief. 2017;14:295–297.

[27] MloziSH, Mmongoyo JA, ChachaM. GC-MS analysis of bioactive phytochemicals from methanolic leaf and root extracts of Tephrosia vogelii. Sci Afr. 2022;16:e01255.

[28] IrawanC, Foliatini H, SulistiawatyL, et al. Volatile compound analysis using GC-MS, phytochemical screening and antioxidant activities of the husk of Julang-jaling (Archidendron bubalinum (Jack) I.C Nielsen) from Lampung, Indonesia. Pharm J. 2018;10:92–98.

[29] LipinskiCA, Lombardo F, DominyBW, et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 1997;23:3–25.

[30] BaeshenNA, Almulaiky YQ, AfifiM, et al. GC-MS analysis of bioactive compounds extracted from plant Rhazya stricta using various solvents. Plants. 2023;12(4):960.

[31] KumarS, ArifM, JawaidT, et al. Antiplatelet and thrombolytic activity of phenolicinsistent fractions from the new-fangled stem of Ficus benghalensis with concurrent GC-MS analysis. Intell Pharm.2023.

[32] LiuY, ChenZ, LiA, et al. The phytochemical potential for brain disease therapy and the possible Nanodelivery solutions for brain access. Front Oncol. 2022;12:936054.

[33] BachhetiRK, WorkuLA, GonfaYH, et al. Prevention and treatment of cardiovascular diseases with plant phytochemicals: a review. Evid Based Complement Alternat Med. 2022:5741198.

[34] MazurakovaA, Koklesova L, SamecM, et al. Anti-breast cancer effects of phytochemicals: primary, secondary, and tertiary care. EPMA J. 2022;13(2):315–334.

[35] KhareT, AnandU, DeyA, et al. Exploring phytochemicals for combating antibiotic resistance in microbial pathogens. Front Pharmacol. 2021;12:720726.

[36] DewickPM. Medicinal natural products: a biosynthetic approach. In: Medicinal Natural Products: A Biosynthetic Approach. 3rd ed. 2009:1–539. https://doi.org/10.1002/9780470742761.

[37] BelloI, ShehuMW, MusaM, et al. Kigelia africana (Lam.) Benth. (Sausage tree): phytochemistry and pharmacological review of a quintessential African traditional medicinal plant. J Ethnopharmacol. 2016;189:253–276.

[38] IsmailN, Kamariah A, LimL, et al. Phytochemical and pharmacological evaluation of methanolic extracts of the leaves of Nepenthes bicalcarata Hook. f. Int. J Pharmacogn Phytochem. Res. 2015;7(6):1127–1138.

[39] RosliMAF, Mediani A, AzizanKA. UPLC-TOF-MS/MS-based metabolomics analysis reveals species-specific metabolite compositions in Pitchers of Nepenthes ampullaria, Nepenthes rafflesiana, and their hybrid Nepenthes × hookeriana. Front Plant Sci. 2021;12:655004.

[40] SaikiaS, Bordoloi M, BanikD. A preliminary study on anti-mycobacterium, anticandida activity and morphological clustering of fifteen folk medicinal plants of Assam, India. Indian J. Pharm. Sci. 2022;84(4):1051–1062.

[41] WojciakM, FeldoM, StolarczykP, et al. Carnivorous plants from Nepenthaceae and Droseraceae as a source of secondary metabolites. Molecules. 2023;28(5):2155.

[42] EilenbergH, Pnini-Cohen S, RahamimY, et al. Induced production of antifungal Naphthoquinones in the pitchers of the carnivorous plant Nepenthes khasiana. J Exp Bot. 2010;61:911–922.

[43] RajG, KurupR, HussainAA, et al. Distribution of naphthoquinones, plumbagin, droserone, and 5-O-methyl droserone in chitin-induced and uninduced Nepenthes khasiana: molecular events in prey capture. J Exp Bot. 2011;62:5429–5436.

[44] GasparriR, Capuano R, GuaglioA, et al. Volatolomic urinary profile analysis for diagnosis of the early stage of lung cancer. J Breath Res. 2022;16(4):046008.

[45] MadhavanSA, Vinotha P, UmaV. Phytochemical screening and comparative GC–MS analysis of bioactive compounds present in methanolic leaf and latex extract Calotropis gigantea (L). Asian J Adv Med Sci. 2020;2(2):1–13.

[46] ChoiD, KangW, ParkT. Anti-allergic and anti-inflammatory effects of undecane on mast cells and keratinocytes. Molecules. 2020;25(7):1554.

[47] KadomaY, Murakami Y, OgiwaraT, et al. Radical-scavenging activity and cytotoxicity of p-Methoxyphenol and p-Cresol Dimers. Molecules. 2010;15:1103–1112.

[48] IbrahimB, Wiranata A, MalikA. The effect of addition of antioxidant 1, 2-dihydro-2, 2, 4-trimethyl-quinoline on characteristics of Crepe Rubber modified asphalt in short term aging and long term aging conditions. Appl Sci. 2020;10:7236.

[49] Nieva-EchevarriaB, Manzanos MJ, GoicoecheaE, et al. 2, 6-Di-Tert-Butyl-Hydroxytoluene and its metabolites in foods. Compr Rev Food Sci Food Saf. 2015;14:67–80.

[50] TortosaV, Pietropaolo V, BrandiV, et al. Computational methods for the identification of molecular targets of toxic food additives. Butylated Hydroxytoluene as a case study. Molecules. 2020;25(9):2229.

[51] ChoiSJ, KimJK, KimHK, et al. 2, 4-Di-tert-butylphenol from sweet potato protects against oxidative stress in PC12 cells and in mice. J Med Food. 2013;16:977–983.

[52] VarshaKK, Devendra L, ShilpaG, et al. 2, 4-Di-tert-butyl phenol as the antifungal, antioxidant bioactive purified from a newly isolated Lactococcus sp. Int J Food Microbiol. 2015;211:44–50.

[53] PrakashP, SelvamK, GayathiriE, et al. Plant-based natural bioactive compounds 2, 4-Ditert-Butylphenolas: a potential candidates against SARS-Cov-2019. Energy Nexus. 2022;6:100080.

[54] PiaoMJ, AhnMJ, KangKA, et al. Phloroglucinol inhibits ultraviolet B radiation-induced oxidative stress in the mouse skin. Int J Radiat Biol. 2014;90(10):928–935.

[55] KimRK, UddinN, HyunJW, et al. Novel anticancer activity of phloroglucinol against breast cancer stem-like cells. Toxicol Appl Pharmacol. 2015;286(3):143–150.

[56] BlanchardC, Pouchain D, VanderkamP, et al. Efficacy of phloroglucinol for treatment of abdominal pain: a systematic review of literature and meta-analysis of randomised controlled trials versus placebo. Eur J Clin Pharmacol. 2018;74:541–548.

[57] WuF, ChenY, ZhengC. Efficacy of phloroglucinol for acceleration of labour: a systematic review and meta-analysis. Arch Gynecol Obstet. 2021;304(2):421–428.

[58] El OumariFE, Mammate N, ImtaraH, et al. Chemical composition, antioxidant potentials, and calcium oxalate Anticrystallization activity of polyphenol and saponin fractions from Argania spinosa L. Press Cake. Plants (Basel). 2022;11(14):1852.

[59] SelvamangaiG, Bhaskar A. GC-MS analysis of phytocomponents in the methanolic extract of Eupatorium triplinerve. Asian Pac J Trop Biomed. 2012:S1329–S1332.

[60] GeethaDH, Rajeswari M, IndhiramuthuJ. Chemical profiling of Elaeocarpus serratus L. by GC-MS. Asian Pac J Trop Biomed. 2013;3(12):985–987.

[61] BabuM, Johnson D, RajaA, et al. Chemical constituents and their biological activity of Ulva lactuca Linn. Int J Pharm Drug Anal. 2014;2:595–600.

[62] AbubakarMN, Majinda RRT. GC-MS analysis and preliminary antimicrobial activity of Albizia adianthifolia (Schumach) and Pterocarpus angolensis (DC). Medicines (Basel). 2016;3(1):3.

[63] VijayabaskarG, ElangoV. Determination of phytocompounds in Withania somnifera and Smilax china using GC-MS technique. J Pharmacogn Phytochem. 2018;7(6):554–557.

[64] JiaCY, LiJY, HaoGF, et al. A drug-likeness toolbox facilitates ADMET study in drug discovery. Drug Discov Today. 2020;25(1):248–258.

[65] FerreiraLLG, Andricopulo AD. ADMET modeling approaches in drug discovery. Drug Discov Today. 2019;24(5):1157–1165.

[66] Ntie-KangF, Onguene PA, LifongoLL, et al. The potential of anti-malarial compounds derived from African medicinal plants, part II: a pharmacological evaluation of nonalkaloids and non-terpenoids. Malar J. 2014;13:81.

[67] AbdullahA, BiswasP, SahabuddinM, et al. Molecular dynamics simulation and pharmacoinformatic integrated analysis of bioactive phytochemicals from Azadirachta indica (Neem) to treat diabetes mellitus. J Chem. 2023;4170703:1–19.

RIGHTS & PERMISSIONS

2023 2023 The Authors. Publishing services by Elsevier B.V. on behalf of KeAi Communications Co. Ltd.