Methanol extraction revealed anticancer compounds Quinic Acid, 2(5H)‑Furanone and Phytol in Andrographis paniculata
- Authors:
- Pawan Kumar Anoor
- A Nichita Yadav
- Karthik Rajkumar
- Ramesh Kande
- Chaturvedula Tripura
- K Srinivas Naik
- Sandeepta Burgula
-
Affiliations: Department of Microbiology, University College of Science, Osmania University, Hyderabad, Telangana 500007, India, CSIR‑Centre for Cellular and Molecular Biology Annexe‑II, Medical Biotechnology Campus, Annexe‑II, Hyderabad, Telangana 500007, India, Centre for Plant Molecular Biology, Osmania University, Hyderabad, Telangana 500007, India - Published online on: September 13, 2022 https://doi.org/10.3892/mco.2022.2584
- Article Number: 151
-
Copyright: © Anoor et al. This is an open access article distributed under the terms of Creative Commons Attribution License.
This article is mentioned in:
Abstract
Ouhtit A, Gaur RL, Abdraboh M, Ireland SK, Rao PN, Raj SG, Al-Riyami H, Shanmuganathan S, Gupta I, Murthy SN, et al: Simultaneous inhibition of cell-cycle, proliferation, survival, metastatic pathways and induction of apoptosis in breast cancer cells by a phytochemical super-cocktail: Genes that underpin its mode of action. J Cancer. 4:703–715. 2013.PubMed/NCBI View Article : Google Scholar | |
Sukanya SL, Sudisha J, Hariprasad P, Niranjana SR, Prakash HS and Fathima SK: Antimicrobial activity of leaf extracts of Indian medicinal plants against clinical and phytopathogenic bacteria. Afr J Biotechnol. 8:6677–6682. 2009. | |
Abutbul S, Golan-Goldhirsh A, Barazani O, Ofir R and Zilberg D: Screening of desert plants for use against bacterial pathogens in fish. Isr J Aquacult-Bamid. 57:71–80. 2005. | |
Pandey G and Madhuri S: Significance of fruits and vegetables in malnutrition cancer. Plant Arch. 10:517–22. 2010. | |
Pandey G, Madhuri S and Mandloi AK: Medicinal plants useful in fish diseases. Plant Arch. 12:1–4. 2012. | |
Ravikumar S, Selvan GP and Gracelin AA: Antimicrobial activity of medicinal plants along Kanyakumari coast, Tamil Nadu, India. Afr J Basic Appl Sci. 2:153–157. 2010. | |
Umamaheswari S and Mainzen Prince PS: Antihyperglycaemic effect of ‘ilogen-excel’, an ayurvedic herbal formulation in streptozotocin-induced diabetes mellitus. Acta Pol Pharm. 64:53–61. 2007.PubMed/NCBI | |
Misra P, Pal NL, Guru PY, Katiyar JC, Srivastava V and Tandon JS: Antimalarial activity of Andrographis paniculata (Kalmegh) against plasmodium berghei NK 65 in mastomys natalensis. Int J Pharmacogn. 30:263–274. 1992. | |
Singha PK, Roy S and Dey S: Antimicrobial activity of Andrographis paniculata. Fitoterapia. 74:692–694. 2003.PubMed/NCBI View Article : Google Scholar | |
Ernst E and Cassileth BR: The prevalence of complementary/alternative medicine in cancer: A systematic review. Cancer. 83:777–782. 1998.PubMed/NCBI View Article : Google Scholar | |
Newman DJ and Cragg GM: Natural products as sources of new drugs from 1981 to 2014. J Nat Prod. 79:629–661. 2016.PubMed/NCBI View Article : Google Scholar | |
Newman DJ and Cragg GM: Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J Nat Prod. 83:770–803. 2020.PubMed/NCBI View Article : Google Scholar | |
See D, Mason S and Roshan R: Increased tumor necrosis factor alpha (TNF-alpha) and natural killer cell (NK) function using an integrative approach in late stage cancers. Immunol Invest. 31:137–153. 2002.PubMed/NCBI View Article : Google Scholar | |
Ahilan B, Nithiyapriyatharshini A and Ravaneshwaran K: Influence of certain herbal additives on the growth, survival and disease resistance of goldfish, carassius auratus (Linnaeus). Tamilnadu J Vet Ani Sci. 6:5–11. 2010. | |
Zilberberg MD, Shorr AF, Micek ST, Vazquez-Guillamet C and Kollef MH: Multi-drug resistance, inappropriate initial antibiotic therapy and mortality in Gram-negative severe sepsis and septic shock: A retrospective cohort study. Crit Care. 18(596)2014.PubMed/NCBI View Article : Google Scholar | |
Runyoro DK, Matee MI, Ngassapa OD, Joseph CC and Mbwambo ZH: Screening of Tanzanian medicinal plants for anti-Candida activity. BMC Complement Altern Med. 6(11)2006.PubMed/NCBI View Article : Google Scholar | |
Shukla B, Visen PKS, Patnaik GK and Dhawan BN: Choleretic effect of andrographolide in rats and guinea pigs1. Planta Med. 58:146–149. 1992.PubMed/NCBI View Article : Google Scholar | |
Srinivasa Reddy P, Jamil K, Madhusudhan P, Anjani G and Das B: Antibacterial activity of isolates from piper longum and taxus baccata. Pharm Biol. 39:236–238. 2001. | |
Prajapati ND, Purohit SS, Sharma AK and Kumar T: A handbook of medicinal plants: A complete source book. Agrobios, Rajasthan, p554, 2003. | |
Chang HM and But PP: Pharmacology and Applications of Chinese Materia Medica. Vol 1. World Scientific, Singapore, p304, 1986. | |
Liu J, Wang ZT and Ji LL: In vivo and in vitro anti-inflammatory activities of neoandrographolide. Am J Chin Med. 35:317–328. 2007.PubMed/NCBI View Article : Google Scholar | |
Islam MT, Ali ES, Uddin SJ, Shaw S, Islam MA, Ahmed MI, Chandra Shill M, Karmakar UK, Yarla NS, Khan IN, et al: Phytol: A review of biomedical activities. Food Chem Toxicol. 121:82–94. 2018.PubMed/NCBI View Article : Google Scholar | |
Suriyo T, Pholphana N, Rangkadilok N, Thiantanawat A, Watcharasit P and Satayavivad J: Andrographis paniculata extracts and major constituent diterpenoids inhibit growth of intrahepatic cholangiocarcinoma cells by inducing cell cycle arrest and apoptosis. Planta Med. 80:533–543. 2014.PubMed/NCBI View Article : Google Scholar | |
Fulda S: Modulation of apoptosis by natural products for cancer therapy. Planta Med. 76:1075–1079. 2010.PubMed/NCBI View Article : Google Scholar | |
Mishra T: Ethno-botanical and therapeutic importance of sacred plants of Terai region of Gorakhpur division. Eur J Pharm Med Res. 3:534–540. 2016. | |
Plubrukarn A, Pinsuwan S, Ingkatawornwong S and Supavita T: Stability of andrographolide in powdered Andrographis herb under accelerated conditions. Planta Med. 72:954–956. 2006.PubMed/NCBI View Article : Google Scholar | |
Kumar RA, Sridevi K, Kumar NV, Nanduri S and Rajagopal S: Anticancer and immunostimulatory compounds from Andrographis paniculata. J Ethnopharmacol. 92:291–295. 2004.PubMed/NCBI View Article : Google Scholar | |
Li L, Yue GG, Lee JK, Wong EC, Fung KP, Yu J, Lau CB and Chiu PW: The adjuvant value of Andrographis paniculata in metastatic esophageal cancer treatment-from preclinical perspectives. Sci Rep. 7(854)2017.PubMed/NCBI View Article : Google Scholar | |
Chiou WF, Chen CF and Lin JJ: Mechanisms of suppression of inducible nitric oxide synthase (iNOS) expression in RAW 264.7 cells by andrographolide. Br J Pharmacol. 129:1553–1560. 2000.PubMed/NCBI View Article : Google Scholar | |
Rajagopal S, Kumar RA, Deevi DS, Satyanarayana C and Rajagopalan R: Andrographolide, a potential cancer therapeutic agent isolated from Andrographis paniculata. J Exp Ther Oncol. 3:147–158. 2003.PubMed/NCBI View Article : Google Scholar | |
Nanduri S, Nyavanandi VK, Thunuguntla SS, Kasu S, Pallerla MK, Ram PS, Rajagopal S, Kumar RA, Ramanujam R, Babu JM, et al: Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents. Bioorg Med Chem Lett. 14:4711–4717. 2004.PubMed/NCBI View Article : Google Scholar | |
Khandelwal KR: Practical Pharmacognosy. Pragati Books Pvt. Ltd., Pune, 2008. | |
Razack S, Kumar KH, Nallamuthu I, Naika M and Khanum F: Antioxidant, biomolecule oxidation protective activities of Nardostachys jatamansi DC and its phytochemical analysis by RP-HPLC and GC-MS. Antioxidants (Basel). 4:185–203. 2015.PubMed/NCBI View Article : Google Scholar | |
Konappa N, Udayashankar AC, Krishnamurthy S, Pradeep CK, Chowdappa S and Jogaiah S: GC-MS analysis of phytoconstituents from Amomum nilgiricum and molecular docking interactions of bioactive serverogenin acetate with target proteins. Sci Rep. 10(16438)2020.PubMed/NCBI View Article : Google Scholar | |
Tsai HC, Li YC, Hsu SH, Young TH and Chen MH: Inhibition of growth and migration of oral and cervical cancer cells by citrus polyphenol. J Formos Med Assoc. 115:171–185. 2016.PubMed/NCBI View Article : Google Scholar | |
Ganguly A, Yang H, Sharma R, Patel KD and Cabral F: The role of microtubules and their dynamics in cell migration. J Biol Chem. 287:43359–43369. 2012.PubMed/NCBI View Article : Google Scholar | |
Nikolova I, Marinov L, Georgieva A, Toshkova R, Malchev M, Voynikov Y and Kostadinova I: Metamizole (dipyrone)-cytotoxic and antiproliferative effects on HeLa, HT-29 and MCF-7 cancer cell lines. Biotechnol Biotechnol Equip. 32:1327–1337. 2018. | |
American Veterinary Medical Association (AVMA): AVMA Guidelines for the Euthanasia of Animals: 2020 Edition. AVMA, Schaumburg, IL, 2020. | |
Okhuarobo A, Falodun JE, Erharuyi O, Imieje V, Falodun A and Langer P: Harnessing the medicinal properties of Andrographis paniculata for diseases and beyond: A review of its phytochemistry and pharmacology. Asian Pac J Trop Dis. 4:213–222. 2014. | |
Oskoueian E, Abdullah N, Ahmad S, Saad WZ, Omar AR and Ho YW: Bioactive compounds and biological activities of Jatropha curcas L. kernel meal extract. Int J Mol Sci. 12:5955–5970. 2011.PubMed/NCBI View Article : Google Scholar | |
Özçelik B, Kartal M and Orhan I: Cytotoxicity, antiviral and antimicrobial activities of alkaloids, flavonoids, and phenolic acids. Pharm Biol. 49:396–402. 2011.PubMed/NCBI View Article : Google Scholar | |
Pejin B, Savic A, Sokovic M, Tesevic V, Savic A, Radotic K and Mojovic M: Further in vitro evaluation of antiradical and antimicrobial activities of phytol. Nat Prod Res. 28:372–376. 2014.PubMed/NCBI View Article : Google Scholar | |
Sareer O, Ahmad S and Umar S: Andrographis paniculata: A critical appraisal of extraction, isolation and quantification of andrographolide and other active constituents. Nat Prod Res. 28:2081–2101. 2014.PubMed/NCBI View Article : Google Scholar | |
Rajani M, Shrivastava N and Ravishankara MN: A rapid method for isolation of andrographolide from Andrographis paniculata nees (Kalmegh). Pharm Biol. 38:204–209. 2000.PubMed/NCBI View Article : Google Scholar | |
Redza-Dutordoir M and Averill-Bates DA: Activation of apoptosis signalling pathways by reactive oxygen species. Biochim Biophys Acta. 1863:2977–2992. 2016.PubMed/NCBI View Article : Google Scholar | |
Wang CZ, Calway T and Yuan CS: Herbal medicines as adjuvants for cancer therapeutics. Am J Chin Med. 40:657–669. 2012.PubMed/NCBI View Article : Google Scholar | |
Wu YC, Luo SH, Mei WJ, Cao L, Wu HQ and Wang ZY: Synthesis and biological evaluation of 4-biphenylamino-5-halo-2(5H)-furanones as potential anticancer agents. Eur J Med Chem. 139:84–94. 2017.PubMed/NCBI View Article : Google Scholar | |
Lattmann E, Sattayasai N, Schwalbe CS, Niamsanit S, Billington DC, Lattmann P, Langley CA, Singh H and Dunn S: Novel anti-bacterials against MRSA: Synthesis of focussed combinatorial libraries of tri-substituted 2(5H)-furanones. Curr Drug Discov Technol. 3:125–134. 2006.PubMed/NCBI View Article : Google Scholar | |
Zapf S, Anke T and Sterner O: Incrustoporin, a new antibiotic from Incrustoporia carneola (Bres.) Ryv. (Basidiomycetes). Acta Chem Scand (Cph). 49:233–234. 1995.PubMed/NCBI View Article : Google Scholar | |
Hashem AI, Youssef AS, Kandeel KA and Abou-Elmagd WS: Conversion of some 2(3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activity. Eur J Med Chem. 42:934–939. 2007.PubMed/NCBI View Article : Google Scholar | |
Weber V, Coudert P, Rubat C, Duroux E, Vallée-Goyet D, Gardette D, Bria M, Albuisson E, Leal F, Gramain JC, et al: Novel 4,5-diaryl-3-hydroxy-2(5H)-furanones as anti-oxidants and anti-inflammatory agents. Bioorg Med Chem. 10:1647–1658. 2002.PubMed/NCBI View Article : Google Scholar | |
Cinkilic N, Cetintas SK, Zorlu T, Vatan O, Yilmaz D, Cavas T, Tunc S, Ozkan L and Bilaloglu R: Radioprotection by two phenolic compounds: Chlorogenic and quinic acid, on X-ray induced DNA damage in human blood lymphocytes in vitro. Food Chem Toxicol. 53:359–363. 2013.PubMed/NCBI View Article : Google Scholar | |
Pero RW, Lund H and Leanderson T: Antioxidant metabolism induced by quinic acid. Increased urinary excretion of tryptophan and nicotinamide. Phytother Res. 23:335–346. 2009.PubMed/NCBI View Article : Google Scholar | |
Inbathamizh L and Padmini E: Quinic acid as a potent drug candidate for prostate cancer-a comparative pharmacokinetic approach. Asian J Pharm Clin Res. 6:106–112. 2013. | |
Jang SA, Park DW, Kwon JE, Song HS, Park B, Jeon H, Sohn EH, Koo HJ and Kang SC: Quinic acid inhibits vascular inflammation in TNF-α-stimulated vascular smooth muscle cells. Biomed Pharmacother. 96:563–571. 2017.PubMed/NCBI View Article : Google Scholar | |
Zhang W, Zhu XL, Ding W and Shi XX: A novel stereoselective synthesis of (-)-quinic acid starting from the naturally abundant (-)-shikimic acid. Tetrahedron Asymmetry. 26:1375–1381. 2015. | |
Soh Y, Kim JA, Sohn NW, Lee KR and Kim SY: Protective effects of quinic acid derivatives on tetrahydropapaveroline-induced cell death in C6 glioma cells. Biol Pharm Bull. 26:803–807. 2003.PubMed/NCBI View Article : Google Scholar | |
de Moraes J, de Oliveira RN, Costa JP, Junior AL, de Sousa DP, Freitas RM, Allegretti SM and Pinto PL: Phytol, a diterpene alcohol from chlorophyll, as a drug against neglected tropical disease Schistosomiasis mansoni. PLoS Negl Trop Dis. 8(e2617)2014.PubMed/NCBI View Article : Google Scholar | |
Guo J, Yuan Y, Lu D, Du B, Xiong L, Shi J, Yang L, Liu W, Yuan X, Zhang G and Wang F: Two natural products, trans-phytol and (22E)-ergosta-6,9,22-triene-3β,5α,8α-triol, inhibit the biosynthesis of estrogen in human ovarian granulosa cells by aromatase (CYP19). Toxicol Appl Pharmacol. 279:23–32. 2014.PubMed/NCBI View Article : Google Scholar | |
Takahashi N, Kawada T, Goto T, Yamamoto T, Taimatsu A, Matsui N, Kimura K, Saito M, Hosokawa M, Miyashita K and Fushiki T: Dual action of isoprenols from herbal medicines on both PPARgamma and PPARalpha in 3T3-L1 adipocytes and HepG2 hepatocytes. FEBS Lett. 514:315–322. 2002.PubMed/NCBI View Article : Google Scholar | |
Costa JP, de Oliveira GA, de Almeida AA, Islam MT, de Sousa DP and de Freitas RM: Anxiolytic-like effects of phytol: Possible involvement of GABAergic transmission. Brain Res. 1547:34–42. 2014.PubMed/NCBI View Article : Google Scholar | |
Santos CC, Salvadori MS, Mota VG, Costa LM, de Almeida AA, de Oliveira GA, Costa JP, de Sousa DP, de Freitas RM and de Almeida RN: Antinociceptive and antioxidant activities of phytol in vivo and in vitro models. Neurosci J. 2013(949452)2013.PubMed/NCBI View Article : Google Scholar | |
Arnhold T, Elmazar MM and Nau H: Prevention of vitamin A teratogenesis by phytol or phytanic acid results from reduced metabolism of retinol to the teratogenic metabolite, all-trans-retinoic acid. Toxicol Sci. 66:274–282. 2002.PubMed/NCBI View Article : Google Scholar | |
Ryu KR, Choi JY, Chung S and Kim DH: Anti-scratching behavioral effect of the essential oil and phytol isolated from Artemisia princeps Pamp. in mice. Planta Med. 77:22–26. 2011.PubMed/NCBI View Article : Google Scholar | |
Chowdhury RR and Ghosh SK: Phytol-derived novel isoprenoid immunostimulants. Front Immunol. 3(49)2012.PubMed/NCBI View Article : Google Scholar | |
Rajab MS, Cantrell CL, Franzblau SG and Fischer NH: Antimycobacterial activity of (E)-phytol and derivatives: A preliminary structure-activity study. Planta Med. 64:2–4. 1998.PubMed/NCBI View Article : Google Scholar | |
Saikia D, Parihar S, Chanda D, Ojha S, Kumar JK, Chanotiya CS, Shanker K and Negi AS: Antitubercular potential of some semisynthetic analogues of phytol. Bioorg Med Chem Lett. 20:508–512. 2010.PubMed/NCBI View Article : Google Scholar | |
Inoue Y, Hada T, Shiraishi A, Hirose K, Hamashima H and Kobayashi S: Biphasic effects of geranylgeraniol, teprenone, and phytol on the growth of Staphylococcus aureus. Antimicrob Agents Chemother. 49:1770–1774. 2005.PubMed/NCBI View Article : Google Scholar | |
Sakthivel R, Malar DS and Devi KP: Phytol shows anti-angiogenic activity and induces apoptosis in A549 cells by depolarizing the mitochondrial membrane potential. Biomed Pharmacother. 105:742–752. 2018.PubMed/NCBI View Article : Google Scholar | |
Zhao Q, Ou J, Huang C, Qiu R, Wang Y, Liu F, Zheng J and Ou S: Absorption of 1-dicysteinethioacetal-5-hydroxymethylfurfural in rats and its effect on oxidative stress and gut microbiota. J Agric Food Chem. 66:11451–11458. 2018.PubMed/NCBI View Article : Google Scholar | |
Silva Ferreira AC, Rodrigues P, Hogg T and Guedes de Pinho P: Influence of some technological parameters on the formation of dimethyl sulfide, 2-mercaptoethanol, methionol, and dimethyl sulfone in port wines. J Agric Food Chem. 51:727–732. 2003.PubMed/NCBI View Article : Google Scholar | |
Yoshiki Y and Okubo K: Active oxygen scavenging activity of DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4 H-pyran-4-one) saponin in soybean seed. Biosci Biotechnol Biochem. 59:1556–1557. 1995. | |
Nair SC, Kurumboor SK and Hasegawa JH: Saffron chemoprevention in biology and medicine: A review. Cancer Biother. 10:257–264. 1995.PubMed/NCBI View Article : Google Scholar | |
Begum SFMM, Priya S, Sundararajan R and Hemalatha S: Novel anticancerous compounds from Sargassum wightii: In silico and in vitro approaches to test the antiproliferative efficacy. J Adv Pharm Educ Res. 7:272–276. 2017. | |
Mujeeb F, Bajpai P and Pathak N: Phytochemical evaluation, antimicrobial activity, and determination of bioactive components from leaves of Aegle marmelos. Biomed Res In. 2014(497606)2014.PubMed/NCBI View Article : Google Scholar | |
Inagaki M, Jyoyama H, Ono T, Yamada K, Kobayashi M, Baba T, Touchi A, Iwatani K, Ohkawa T, Matsumoto S and Tsuri T: Synthesis and activities of oxidative metabolites of the anti-arthritic drug candidate S-2474. Bioorg Med Chem. 11:2415–2419. 2003.PubMed/NCBI View Article : Google Scholar | |
Abdullah BM, Mehdi MAH, Khan AR and Pathan JM: Gas chromatography-mass spectrometry (GC-MS) analysis of ajwain (Trachyspermum ammi) seed extract. Int J Pharm Qual Assur. 11:228–231. 2020. | |
Rahbar N, Shafaghat A and Salimi F: Antimicrobial activity and constituents of the hexane extracts from leaf and stem of Origanum vulgare L. ssp. Viride (Boiss.) Hayek. growing wild in Northwest Iran. J Med Plants Res. 6:2681–2685. 2012. | |
Zekeya N, Chacha M, Shahada F and Kidukuli A: Analysis of phytochemical composition of Bersama abyssinica by gas chromatography-mass spectrometry. J Pharmacogn Phytochem. 3:246–252. 2014. | |
Huang CB and Ebersole JL: A novel bioactivity of omega-3 polyunsaturated fatty acids and their ester derivatives. Mol Oral Microbiol. 25:75–80. 2010.PubMed/NCBI View Article : Google Scholar | |
Ahmad B, Khan I, Bashir S and Azam S: Chemical composition and antifungal, phytotoxic, brine shrimp cytotoxicity, insecticidal and antibacterial activities of the essential oils of Acacia modesta. J Med Plants Res. 6:4653–4659. 2012. | |
Roy RN, Laskar S and Sen SK: Dibutyl phthalate, the bioactive compound produced by Streptomyces albidoflavus 321.2. Microbiol Res. 161:121–126. 2006.PubMed/NCBI View Article : Google Scholar | |
Sunita A, Ganesh K and Sonam M: Screening and evaluation of bioactive components of Cenchrus ciliaris L. by GC-MS analysis. Int Res J Pharm. 8:69–76. 2017. | |
Yu FR, Lian XZ, Guo HY, McGuire PM, Li RD, Wang R and Yu FH: Isolation and characterization of methyl esters and derivatives from euphorbia kansui (euphorbiaceae) and their inhibitory effects on the human SGC-7901 cells. J Pharm Pharm Sci. 8:528–535. 2005.PubMed/NCBI | |
Siyumbwa SN, Ekeuku SO, Amini F, Emerald NM, Sharma D and Okechukwu PN: Wound healing and antibacterial activities of 2-Pentadecanone in streptozotocin-induced Type 2 diabetic rats. Pharmacogn Mag. 15:71–77. 2019. | |
Gupta S, Afaq F and Mukhtar H: Involvement of nuclear factor-kappa B, Bax and Bcl-2 in induction of cell cycle arrest and apoptosis by apigenin in human prostate carcinoma cells. Oncogene. 21:3727–3738. 2002.PubMed/NCBI View Article : Google Scholar | |
Tian Z, Shen J, Moseman AP, Yang Q, Yang J, Xiao P, Wu E and Kohane IS: Dulxanthone A induces cell cycle arrest and apoptosis via up-regulation of p53 through mitochondrial pathway in HepG2 cells. Int J Cancer. 122:31–38. 2008.PubMed/NCBI View Article : Google Scholar | |
Yue GG, Lee JK, Kwok HF, Cheng L, Wong EC, Jiang L, Yu H, Leung HW, Wong YL, Leung PC, et al: Novel PI3K/AKT targeting anti-angiogenic activities of 4-vinylphenol, a new therapeutic potential of a well-known styrene metabolite. Sci Rep. 5(11149)2015.PubMed/NCBI View Article : Google Scholar | |
Cimmino A, Scafato P, Mathieu V, Ingels A, D'Amico W, Pisani L, Maddau L, Superchi S, Kiss R and Evidente A: Natural and synthetic furanones with anticancer activity. Nat Prod Commun. 11:1471–1474. 2016.PubMed/NCBI | |
Ma F, Zhang J, Li M, Yu J, Luo W, Li X and Wei M: Synthesis of novel matrine derivatives containing furanone skeleton and preliminary evaluation of their anticancer activity in vitro. Chin J Org Chem. 38:2633–2638. 2018. | |
de Alencar MVOB, Islam MT, de Lima RMT, Paz MFCJ, Dos Reis AC, da Mata AMOF, Filho JWGO, Cerqueira GS, Ferreira PMP, E Sousa JMC, et al: Phytol as an anticarcinogenic and antitumoral agent: An in vivo study in swiss mice with DMBA-Induced breast cancer. IUBMB Life. 71:200–212. 2019.PubMed/NCBI View Article : Google Scholar | |
Murugesan A, Holmstedt S, Brown KC, Koivuporras A, Macedo AS, Nguyen N, Fonte P, Rijo P, Yli-Harja O, Candeias NR and Kandhavelu M: Design and synthesis of novel quinic acid derivatives: In vitro cytotoxicity and anticancer effect on glioblastoma. Future Med Chem. 12:1891–1910. 2020.PubMed/NCBI View Article : Google Scholar | |
Singh A, Chauhan SS and Tripathi V: Quinic acid attenuates oral cancer cell proliferation by downregulating cyclin D1 Expression and Akt signaling. Pharmacogn Mag. 14:14–19. 2018. |