Antileukemic ancistrobenomine B and related 5,1′-coupled naphthylisoquinoline alkaloids from the Chinese liana Ancistrocladus tectorius

Taylor, 2005, Revision of Ancistrocladus Wall. (Ancistrocladaceae), Ann. Mo. Bot. Gard., 92, 360 Keng, 1967, Observations on Ancistrocladus tectorius, Gard. Bull. Singapore, 22, 113 Keng, 1970, Further observations on Ancistrocladus tectorius, Gard. Bull. Singapore, 25, 235 Said, 2001, Biological activity studies of Ancistrocladus tectorius, Pharm. Biol., 39, 357, 10.1076/phbi.39.5.357.5897 Siti Munirah, 2007, Ancistrocladus tectorius (Malaysia), 12, 5 Wiart, 2004, Antimicrobial screening of plants used for traditional medicine in the state of Perak, Peninsular Malaysia, Fitoterapia, 75, 68, 10.1016/j.fitote.2003.07.013 Ruangrungsi, 1985, Traditional medicinal plants of Thailand, V. Ancistrotectorine, a new naphthalene-isoquinoline alkaloid from Ancistrocladus tectorius, J. Nat. Prod., 48, 529, 10.1021/np50040a003 Zheng, 2009, Ethnobotanical study on medicinal plants around Mt. Yinggeling, Hainan Island, China, J. Ethnopharmacol., 124, 197, 10.1016/j.jep.2009.04.042 Zheng, 2013, Ethnobotanical study on medicinal plants around Limu Mountains of Hainan Island, China, J. Ethnopharmacol., 148, 964, 10.1016/j.jep.2013.05.051 François, 1997, Growth inhibition of asexual erythrocytic forms of Plasmodium falciparum and P. berghei in vitro by naphthylisoquinoline alkaloid-containing extracts of Ancistrocladus and Triphyophyllum species, Int. J. Pharmacogn., 35, 55, 10.1076/phbi.35.1.55.13272 François, 1997, Retarded development of exoerythrocytic stages of the rodent malaria parasite Plasmodium berghei in human hepatoma cells by extracts from Dioncophyllaceae and Ancistrocladaceae species, Int. J. Parasitol., 27, 29, 10.1016/S0020-7519(96)00171-3 Tanaka, 2001, Potential immunosuppressive and antiinflammatory activities of Malaysian medicinal plants characterized by reduced cell surface expression of cell adhesion molecules, Phytother. Res., 15, 681, 10.1002/ptr.778 Spelman, 2011, Traditional herbal remedies that influence cell adhesion molecule activity, Phytother. Res., 25, 473, 10.1002/ptr.3350 Chen, 1981, Isolation and identification of the alkaloids from Ancistrocladus tectorius, XaoXue XueBao (Acta Pharm. Sinica), 16, 519 Kawami, 2010, Effect of Thai plant extracts on P-glycoprotein function and viability in paclitaxel-resistant HepG2 cells, Drug Metab. Pharmacokinet., 25, 155, 10.2133/dmpk.25.155 Meksuriyen, 1990, NMR spectroscopic analysis of ancistrocladidine, Phytochemistry, 29, 2750, 10.1016/0031-9422(90)85241-7 Bringmann, 1992, (+)-Ancistrocline, a naphthylisoquinoline alkaloid from Ancistrocladus tectorius, Phytochemistry, 31, 3297, 10.1016/0031-9422(92)83505-S Montagnac, 1995, Isoquinoline alkaloids from Ancistrocladus tectorius, Phytochemistry, 39, 701, 10.1016/0031-9422(94)00936-N Manfredi, 1996, Three new naphthyldihydroisoquinoline alkaloids from Ancistrocladus tectorius, J. Nat. Prod., 59, 854, 10.1021/np960410u Tang, 2000, Four new naphthylisoquinoline alkaloids from Ancistrocladus tectorius, J. Nat. Prod., 63, 1384, 10.1021/np000091d Liu, 2008, Studies on constituents of the stems and branches of Ancistrocladus tectorius, Zhongguo Yaoxue Zazhi (Chin. Pharm. J.), 43, 1060 Tang, 2010, Two new naphthylisoquinoline alkaloids from stems and leaves of Ancistrocladus tectorius, Nat. Prod. Res., 24, 989, 10.1080/14786410902836727 Xu, 2010, Shuangancistrotectorines A-E, dimeric naphthylisoquinoline alkaloids with three chiral biaryl axes, from the Chinese plant Ancistrocladus tectorius, Chem. Eur. J., 16, 4206, 10.1002/chem.200903247 Bringmann, 2013, Highly selective antiplasmodial naphthylisoquinoline alkaloids from Ancistrocladus tectorius, Phytochemistry, 91, 220, 10.1016/j.phytochem.2012.02.017 Jiang, 2013, Five novel naphthylisoquinoline alkaloids with growth inhibitory activities against human leukemia cells HL-60, K562 and U937 from stems and leaves of Ancistrocladus tectorius, Fitoterapia, 91, 305, 10.1016/j.fitote.2013.09.010 Bringmann, 2016, Ancistrotectoquinones A and B, the first quinoid naphthylisoquinoline alkaloids, from the Chinese liana Ancistrocladus tectorius, Nat. Prod. Commun., 11, 971 Bringmann, 2016, Ancistectorine D, a naphthylisoquinoline alkaloid with antiprotozoal and antileukemic activities, and further 5,8′- and 7,1′-linked metabolites from the Chinese liana Ancistrocladus tectorius, Fitoterapia, 115, 1, 10.1016/j.fitote.2016.09.009 Bringmann, 2004, Ancistrobenomine A, the first naphthylisoquinoline oxygenated at Me-3, and related 5,1′-coupled alkaloids, from the “new” plant species Ancistrocladus benomensis, J. Nat. Prod., 67, 2058, 10.1021/np0497651 Bringmann, 2011, Phenolic analogs of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A, from Ancistrocladus cochinchinensis (Ancistrocladaceae), with improved antiprotozoal activities, Phytochemistry, 72, 89, 10.1016/j.phytochem.2010.10.006 Anh, 1997, Naphthylisoquinoline alkaloids from Ancistrocladus cochinchinensis, Phytochemistry, 45, 1287, 10.1016/S0031-9422(97)00110-6 Bringmann, 1995, The naphthylisoquinoline alkaloids, 46, 127 Ibrahim, 2015, Naphthylisoquinoline alkaloids potential drug leads, Fitoterapia, 106, 194, 10.1016/j.fitote.2015.09.014 Desai, 1976, Chemical investigation of some Indian plants: part IX, Indian J. Chem., 14B, 473 Gunatilaka, 1978, Alkaloids of some plants of Sri Lanka – chemistry and pharmacology, Natn. Sci. Coun. Sri Lanka, 6, 39 Unger, 2004, Analytical characterization of crude extracts from an African Ancistrocladus species using high-performance liquid chromatography and capillary electrophoresis coupled to ion trap mass spectrometry, Phytochem. Anal., 15, 21, 10.1002/pca.737 Bringmann, 2016, HIV-inhibitory michellamine-type dimeric naphthylisoquinoline alkaloids from the Central African liana Ancistrocladus congolensis, Phytochemistry, 128, 71, 10.1016/j.phytochem.2016.04.005 Bringmann, 2008, Six naphthylisoquinoline alkaloids and a related benzopyranone from a Congolese Ancistrocladus species related to Ancistrocladus congolensis, Phytochemistry, 69, 1065, 10.1016/j.phytochem.2007.10.027 Bringmann, 2005, ent-Dioncophylleine A and related dehydrogenated naphthylisoquinoline alkaloids, the first Asian Dioncophyllaceae-type alkaloids, from the “new” plant species Ancistrocladus benomensis, J. Nat. Prod., 68, 686, 10.1021/np049626j Govindachari, 1971, Ancistrocladine, a new type of isoquinoline alkaloid from Ancistrocladus heyneanus, Tetrahedron, 27, 1013, 10.1016/S0040-4020(01)92503-7 Govindachari, 1975, Hamatine, a new isoquinoline alkaloid from Ancistrocladus hamatus (Vahl) Gilg, Indian J. Chem., 13, 641 Bringmann, 1996, An improved degradation procedure for determination of the absolute configuration in chiral isoquinoline and β-carboline derivatives, Phytochemistry, 43, 1393, 10.1016/S0031-9422(96)00357-3 Orhan, 2010, Inhibitory activity of marine sponge-derived natural products against parasitic protozoa, Mar. Drugs, 8, 47, 10.3390/md8010047 Kimmig, 1990, Susceptibility of multidrug-resistant human leukemia cell lines to human interleukin 2-activated killer cells, Cancer Res., 50, 6793 Efferth, 2003, Molecular modes of action of artesunate in tumor cell lines, Mol. Pharmacol., 64, 382, 10.1124/mol.64.2.382 Gillet, 2004, Microarray-based detection of multidrug resistance in human tumor cells by expressing profiling of ATP-binding cassette transporter genes, Cancer Res., 64, 8987, 10.1158/0008-5472.CAN-04-1978 O'Brien, 2000, Investigation of the Alamar blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity, Eur. J. Biochem., 267, 5421, 10.1046/j.1432-1327.2000.01606.x Kuete, 2013, Cytotoxicity and modes of action of four naturally occurring benzophenones, Phytomedicine, 20, 528, 10.1016/j.phymed.2013.02.003 Kuete, 2011, Anticancer activities of six selected natural compounds of some Cameroonian medicinal plants, PLoS One, 6, 10.1371/journal.pone.0021762 Dzoyem, 2012, Cytotoxicity and antimicrobial activity of the methanol extract and compounds from Polygonum limbatum, Planta Med., 78, 787, 10.1055/s-0031-1298431 Yang, 2003, Ancisheynine, a novel naphthylisoquinoline alkaloid from Ancistrocladus heyneanus, Tetrahedron Lett., 44, 5827, 10.1016/S0040-4039(03)01397-2 Bringmann, 2006, Ancisheynine, the first N,C-coupled naphthylisoquinoline alkaloid: total synthesis and stereochemical analysis, Org. Lett., 8, 1037, 10.1021/ol052946p Bringmann, 1992, (±)-Dioncophyllacine A, a naphthylisoquinoline alkaloid with a 4-methoxy substituent from the leaves of Triphyophyllum peltatum, Phytochemistry, 31, 4015, 10.1016/S0031-9422(00)97575-7 Bringmann, 1992, Dioncophyllacine B: a new 4-methoxylated naphthylisoquinoline alkaloid from the leaves of Triphyophyllum peltatum, Planta Med., 58, A701, 10.1055/s-2006-961726 Govindachari, 1971, Ancistrocladinine, a minor alkaloid from Ancistrocladus heyneanus Wall, Indian J. Chem., 9, 1421 Govindachari, 1974, Absolute stereochemistry of ancistrocladine and ancistrocladinine, J. Chem. Soc., Perkin Trans. 1, 1413, 10.1039/p19740001413 Bringmann, 2004, Ancistrotanzanine C and related 5,1′- and 7,3′-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis, J. Nat. Prod., 67, 743, 10.1021/np0340549 Dlugosz, 2016, ABC transporters in the development of multidrug resistance in cancer therapy, Curr. Pharm. Des., 22, 4705, 10.2174/1381612822666160302103646 Syed, 2016, P-glycoprotein mediated multidrug resistance reversal by phytochemicals: a review of SAR & future perspectives for drug design, Curr. Top. Med. Chem., 16, 2484, 10.2174/1568026616666160212123814 Li, 2017, Dioncophyllines C2, D2, and F, and related naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus ileboensis with potent activities against Plasmodium falciparum, and against multiple myeloma and leukemia cell lines, J. Nat. Prod., 80, 443, 10.1021/acs.jnatprod.6b00967