Four new cucurbitane-type triterpenes were isolated from the fruit of Momordica charantia L. The structures of the new compounds were identified based on HR-ESI-MS and 1D- and 2D-NMR spectroscopic methods. The cytotoxicity of the isolated compounds was evaluated using three human cancer cell lines, HeLa, Caco2, and U87. Compound 3 exhibited significant cytotoxic activity against HeLa cells with an IC50 value of 11.18 μM. Additionally, the cytoprotective activity of these compounds was determined in vitro against H2O2-induced pancreatic injury. The results revealed that all the compounds obtained possess cytoprotective effects against H2O2-induced injury in MIN6 β-cells at a concentration of 10 μM.
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Jia S, Shen M, Zhang F, Xie J (2017) Recent advances in Momordica charantia: functional components and biological activities. Int J Mol Sci 18:E2555
Anilakumar KR, Kumar GP, Ilaiyaraja N (2015) Nutritional, pharmacological and medicinal properties of Momordica charantia. Int J Nutr Food Sci 4(1):75–83
Wang HY, Kan WC, Cheng TJ, Yu SH, Chang LH, Chuu JJ (2014) Differential anti-diabetic effects and mechanism of action of charantin-rich extract of Taiwanese Momordica charantia between type 1 and type 2 diabetic mice. Food Chem Toxicol 69:347–356
Lo HY, Ho TY, Li CC, Chen JC, Liu JJ, Hsiang CY (2014) A novel insulin receptor-binding protein from Momordica charantia enhances glucose uptake and glucose clearance in vitro and in vivo through triggering insulin receptor signaling pathway. J Agric Food Chem 62:8952–8961
Blum A, Loerz C, Martin HJ, Staab-Weijnitz CA, Maser E (2012) Momordica charantia extract, a herbal remedy for type 2 diabetes, contains a specific 11β-hydroxysteroid dehydrogenase type 1 inhibitor. J Steroid Biochem 128:51–55
Raina K, Kumar D, Agarwal R (2016) Promise of bitter melon (Momordica charantia) bioactives in cancer prevention and therapy. Semin Cancer Biol 40–41:116–129
Kwatra D, Subramaniam D, Ramamoorthy P, Standing D, Moran E, Velayutham R, Mitra A, Umar S, Anant S (2013) Methanolic extracts of bitter melon inhibit colon cancer stem cells by affecting energy homeostasis and autophagy. Evid Based Complement Altern Med 1:1–14
Manoharan G, Jaiswal SR, Singh J (2014) Effect of α, β momorcharin on viability, caspase activity, cytochrome c release and on cytosolic calcium levels in different cancer cell lines. Mol Cell Biochem 388:233–240
Fang EF, Zhang CZY, Wong JH, Shen JY, Li CH, Ng TB (2012) The MAP30 protein from bitter gourd Momordica charantia seeds promotes apoptosis in liver cancer cells in vitro and in vivo. Cancer Lett 324:66–74
Pongnikorn S, Fongmoon D, Kasinrerk W, Limtrakul PN (2003) Effect of bitter melon (Momordica charantia Linn) on level and function of natural killer cells in cervical cancer patients with radiotherapy. J Med Assoc Thai 86:61–68
Sun Y, Huang PL, Li JJ, Huang YQ, Zhang L, Lee-Huang S (2001) Anti-HIV agent MAP30 modulates the expression profile of viral and cellular genes for proliferation and apoptosis in AIDS-related lymphoma cells infected with Kaposi’s sarcoma-associated virus. Biochem Biophys Res Commun 287:983–994
Mwambete KD (2009) The in vitro antimicrobial activity of fruit and leaf crude extracts of Momordica charantia: a Tanzania medicinal plant. Afr Health Sci 9(1):34–39
Gupta S, Raychaudhuri B, Banerjee S, Das B, Mukhopadhaya S, Datta SC (2010) Momordicatin purified from fruits of Momordica charantia is effective to act as a potent antileishmania agent. Parasitol Int 59:192–197
Alessandra B, Tiziana S, Manuela DA, Maria PG (2008) Chemical composition and antimicrobial activity of Momordica charantia seed essential oil. Fitoterapia 79:123–125
Mulholland DA, Sewram V, Osborne R, Pegel KH, Connolly JD (1997) Cucurbitane triterpenoids from the leaves of Momordica foetida. Phytochemistry 45:391–395
Chen JC, Lu L, Zhang XM, Zhou L, Li ZR, Qiu MH (2008) Eight new cucurbitane glycosides, kuguaglycosides A-H, from the root of Momordica charantia L. Helv Chim Acta 91:920–928
Lin KW, Yang SC, Lin CN (2011) Antioxidant constituents from the stems and fruits of Momordica charantia. Food Chem 127:609–614
Hsiao PC, Liaw CC, Hwang SY, Cheng HL, Zhang LJ, Shen CC, Hsu FL, Kuo YH (2013) Antiproliferative and hypoglycemic cucurbitane-type glycosides from the fruits of Momordica charantia. J Agric Food Chem 61:2979–2986
Jiang Y, Peng XR, Yu MY, Wan LS, Zhu GL, Zhao GT, Zhou L, Qiu MH, Liu J (2016) Cucurbitane-type triterpenoids from the aerial parts of Momordica charantia L. Phytochem Lett 16:164–168
Yue JY, Xu J, Cao JQ, Zhang XS, Zhao YQ (2017) Cucurbitane triterpenoids from Momordica charantia L. and their inhibitory activity against α-glucosidase, α-amylase and protein tyrosine phosphatase 1B (PTP1B). J Func Foods 37:624–631
Akihisa T, Higo N, Tokuda H, Ukiya M, Akazawa H, Tochigi Y, Kimura Y, Suzuki T, Nishino H (2007) Cucurbitane-type triterpenoids from the fruits of Momordica charantia and their cancer chemopreventive effects. J Nat Prod 70:1233–1239
Wang XJ, Sun W, Cao JQ, Qu HY, Bi XL, Zhao YQ (2012) Structures of new triterpenoids and cytotoxicity activities of the isolated major compounds from the fruit of Momordica charantia L. J Agric Food Chem 60:3927–3933
Liao YW, Chen CR, Kuo YH, Hsu JL, Shih WL, Cheng HL, Huang TC, Chang CI (2012) Cucurbitane-type triterpenoids from the fruit pulp of Momordica charantia. Nat Prod Commun 7(12):1575–1578
Li QY, Chen HB, Liu ZM, Wang B, Zhao YY (2007) Cucurbitane triterpenoids from Momordica charantia. Magn Reson Chem 45(6):451–456
Zhang LJ, Liaw CC, Hsiao PC, Huang HC, Lin MJ, Lin ZH, Hsu FL, Kuo YH (2014) Cucurbitane-type glycosides from the fruits of Momordica charantia and their hypoglycaemic and cytotoxic activities. J Funct Foods 6:564–574
Liaw CC, Huang HC, Hsiao PC, Zhang LJ, Lin ZH, Hwang SY, Hsu FL, Kuo YH (2014) 5β,19-epoxycucurbitane triterpenoids from Momordica charantia and their anti-inflammatory and cytotoxic activity. Planta Medica 81:62–70
Tuan NQ, Lee DH, Oh J, Kim CS, Heo KS, Myung CS, Na M (2017) Inhibition of proliferation of vascular smooth muscle cells by cucurbitanes from Momordica charantia. J Nat Prod 80:2018–2025
Habtemariam S, Varghese GK (2017) Antioxidant, anti-alpha-glucosidase and pancreatic beta-cell protective effects of methanolic extract of Ensete superbum Cheesm seeds. Asian Pac J Trop Biomed 7:121–125
We are glad to acknowledge the Analytical Center of Shenyang Pharmaceutical University for NMR measurements. The research was supported by National Nature Science Foundation of China (Grant No. 81703389), Youth development support plan of Shenyang Pharmaceutical University (ZQN2016023), Liaoning E & T research center for industrial chromatographic preparation of Natural Products (No. 2008402021), Technology Platform of Industrialization Chromatographic Preparation for Standard Extract of Traditional Chinese Medicine (2010ZX09401-304), and Liaoning (FGW) Engineering Technology Research Center for industrial chromatographic preparation of natural innovative drugs materials (2017-1007).
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Yue, J., Sun, Y., Xu, J. et al. Four new cucurbitane-type triterpenes from Momordica charantia L. with their cytotoxic activities and protective effects on H2O2-damaged pancreatic cells. J Nat Med 74, 34–40 (2020). https://doi.org/10.1007/s11418-019-01336-1
- Momordica charantia L.
- Cucurbitane-type triterpenoid sapogenins
- Cytotoxic activity
- Protection of pancreatic cell oxidative injury