Eleven lignans (1-11) were isolated from the seed of Hernandia nymphaeifolia. Most of the lignans exhibited strong to moderate cytotoxicity against cholangiocarcinoma KKU-M156 and HepG2 cell lines. Compounds 4 and 8 showed cytotoxicity against the KKU-M156 cell line with IC50 values of 5.2 μM (Emax 96%) and 5.4 (Emax 59%) μM, respectively. In the cases of cytotoxicity against the HepG2 cell line, compounds 2, 3, 4, and 8 showed cytotoxicity with IC50 values of 1.7 M (Emax 84%), 4.1 μM (Emax 74%), 4.5 μM (Emax 68%), and 5.2 μM (Emax 78%), respectively.
ChenJJ, ChangYL, TengCM, ChenTS. (2000) Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia. Planta Medica, 66, 251–256.
5.
FangJM, LeeCK, ChengYS. (1992) Lignans from leaves of Juniperus chinensis. Phytochemistry, 31, 3659–3661.
6.
WickramaratneDB, MarE, ChaiH, CastilloJJ, FarnsworthNR, SoejartoDD, CordellGA, PezzutoJM, KinghomAD. (1995) Cytotoxic constituents of Bursera permollis. Planta Medica, 61, 80–81.
7.
IkedaR, NagaoT, OkabeH, NakanoY, MatsunagaH, KatanoM, MoriM. (1998) Antiproliferative constituents in umbelliferae plants. III. Constituents in the root and the ground part of Anthriscus sylvestris Hoffm. Chemical & Pharmaceutical Bulletin, 46, 871–874.
8.
LimYH, LeemMJ, ShinDH, ChangHB, HongSW, MoonEY, LeeDK, YoonSJ, WooWS. (1999) Cytotoxic constituents from the roots of Anthriscus sylvestris. Archives of Pharmacal Research, 22, 208–212.
9.
JiangRW, ZhouJR, HonPM, LiSL, ZhouY, LiLL, YeWC, XuHX, ShawPC, But P PH. (2007) Lignans from Dysosma versipellis with inhibitory effects on prostate cancer cell lines. Journal of Natural Products, 70, 283–286.
10.
YongY, ShinSY, LeeYH, LimY. (2009) Antitumor activity of deoxypodophyllotoxin isolated from Anthriscus sylvestris: Induction of G2/M cell cycle arrest and caspase-dependent apoptosis. Bioorganic & Medicinal Chemistry Letters, 19, 4367–4371.
11.
WuM, JiangZ, DuanH, SunL, ZhangS, ChenM, WangY, GaoQ, SongY, ZhuX, ZhangL. (2013) Deoxypodophyllotoxin triggers neocrotosis in human non-small cell lung cancer NCI-H460 cells. Biomedicine & Pharmacotherapy, 67, 701–706.
12.
ChangLC, SongLL, ParkEJ, LuyengiL, LeeKJ, FarnsworthNR, PezzutoJM, KinghornAD. (2000) Bioactive constituents of Thuja occidentalis. Journal of Natural Products, 63, 1235–1238.
13.
ItoC, ItoigawaM, OgataM, MouXY, TokudaH, NishinoH, FurakawaH. (2001) Lignans as anti-tumor-promoter from the seeds of Hernandia ovigera. Planta Medica, 67, 166–168.
14.
GuJQ, ParkEJ, ToturaS, RiswanS, FongHHS, PezzutoJM, KinghornAD. (2002) Constituents of the twigs of Hernandia ovigera that inhibit the transformation of JB6 murine epidermal cells. Journal of Natural Products, 65, 1065–1068.
15.
SripaB, PairojkulC. (2008) Cholangiocarcinoma: lessons from Thailand. Current Opinion in Gastroenterology, 24, 349–356.
16.
McGlynnKA, TaroneRE, El-SeragHB. (2006) A comparison of trends in the incidence of hepatocellular carcinoma and intrahepatic cholangiocarcinoma in the United States. Cancer Epidemiology Biomarkers & Prevention, 15, 1198–1203.
17.
DicksonRA, HoughtonPJ, HylandsPJ. (2007) Antibacterial and antioxidant cassane diterpenoids from Caesalpinia benthamiana. Phytochemistry, 68, 1436–1441.
18.
LaneAL, KubanekJ. (2006) Structure–activity relationship of chemical defenses from the freshwater plant Micranthemum umbrosum. Phytochemistry, 67, 1224–1231.
19.
KofodH, JorgensenC. (1954) Dehydropodophyllotoxin, a new compound isolated from Podophyllum peltatum. Acta Chemica Scandinavica, 8, 1296–1297.
20.
KuoYC, KuoYH, LinYL, TsaiWJ. (2006) Yatein from Chamaecyparis obtusa suppresses herpes simplex virus type 1 replication in HeLa cells by interruption the immediate-early gene expression. Antiviral Research, 70, 112–120.
21.
RichommeP, BrunetonJ, CabalionP, DebrayMM. (1984) Study of Hernandiaceae. IX. Lignans from two Melanesian Hernandia. Journal of Natural Products, 47, 879–881.
22.
San FelicianoA, MedardeM, LopezJL, PueblaP, Miguel del CorralJM, BarreroAF. (1989) Lignans from Juniperus thurifera. Phytochemistry, 28, 2863–2866.
23.
GonzalezAG, Estevez-ReyesR, MatoC, Estevez-BraunAM. (1990) Three lignans from Bupleurum salicifolium. Phytochemistry, 29, 1981–1983.
24.
TakaokaD, ImookaM, HiroiM. (1977) Studies of lignoids in Lauraceae. III. A new lignan from the heart wood of Cinnamomum Camphora Siep. Bulletin of the Chemical Society of Japan, 50, 2821–2822.
25.
PettitGR, MengY, GearingRP, HeraldDL, PettitRK, DoubekDL, ChapuisJC, TackettLP. (2004) Antineoplastic agents. 522. Hernandia peltata (Malaysia) and Hernandia nymphaeifolia (Republic of Maldives). Journal of Natural Products, 67, 214–220.
26.
TusskornO, PrawanA, SenggunpraiL, KukongviriyapanU, KukongviriyapanV. (2013) Phenethyl isothiocyanate induces apoptosis of cholangiocarcinoma cells through interruption of glutathione and mitochondrial pathway. Naunyn-Schmiedeberg's Archives of Pharmacology, 386, 1009–1016.
