A novel antitumor compound nobiliside D isolated from sea cucumber (Holothuria nobilis Selenka)

Abstract

Abstract. An anticancer compound, triterpene glycoside, was isolated from Holothuria nobilis Selenka. Its chemical structure and configuration were determined by two-dimensional nuclear magnetic resonance spectroscopy and electrospray ionization mass spectrometry. The novel active compound was identified as nobiliside D, with the molecular formula C 40 H 61 O 17 SNa and chemical name 3alcohol. An antitumor test was performed using xCELLigence Real-Time Cell Analysis. Nobiliside D exhibited inhibitory effects on human leukemic cell line K562, human leukemia cell line U937, human lung cancer cell line A-549, human cervix carcinoma cell line HeLa, human breast cancer cell line MCF-7 and human liver carcinoma cell line HepG2. Nobiliside exhibited the greatest inhibitory effect on K562 and MCF-7 cells with an IC 50 of 0.83±0.14 and 0.82±0.11 µg/ml, respectively. When human tumor cell lines K562 and MCF-7 were treated by nobiliside D (0.5 µg/ml) for 24 h, 45.8% of K562 cells and 58.7% of MCF-7 cells were apoptotic, whereas only 0.5% of un-treated control cells were apoptotic. These data indicate the compound should offer potential as a novel drug for the treatment of a range of cancers.

Sea Cucumber (Stichopus japonicas) F2 Enhanced TRAIL-Induced Apoptosis via XIAP Ubiquitination and ER Stress in Colorectal Cancer Cells

“…Many studies have reported that sea cucumber extract contains several compounds, including mono sulfated tritepenoid glycoside Frondoside A, disulfated glycoside Frondoside B, trisulfated glycoside Frondoside C, eicosapentaenoic acid, fucosylated chondroitin sulfate, nobiliside D, 12-methyltetradecanoic acid, sphingoid and canthaxanthin/astaxanthin, that have induced apoptosis in solid cancers, including breast, liver, renal, cervical, lung, and colorectal cancer cells [15,24,25,26]. Amidi et al reported that (Z)-2,3-diphenylacrylonitrile molecules isolated from Persian Gulf SC were identified as potential anti-cancer agents [27].…”

Marine natural products

“…The remaining metabolites reported from echinoderms included steroidal glycosides pentacerosides A 1461 and B 1462 (Pentaceraster gracilis), 694 regulusosides S1 1463 and S2 1464 (P. regulus), 695 pentaregulosides A-G 1465-1471 (P. regulus), 696 and granulatoside C 1472 (Choriaster granulatus), 697 all isolated from starsh, as well as sea cucumbersourced triterpene glycosides nobiliside D 1473 (Holothuria nobilis), 698 stichorrenosides A-D 1474-1477 (Stichopus horrens), 699 magnumosides A 1 -A 4 , B 1 -B 4 , C 1 -C 4 1478-1489 (Neothyonidium (¼Massinium) magnum), 700,701 and fallaxosides B 1 and D 3 1490, 1491 (Cucumaria fallax). 702 Nobiliside D 1473 showed strong cytotoxicity towards a panel of six HTCLs, 698 while magnumoside C 4 1489 enhanced the antiproliferative effects of g-radiation on DLD-1 human colorectal adenocarcinoma cells. 700 Biological evaluation of carbohydrate conjugates of the sea urchin quinonoid ethylmompain identied analogues with enhanced cytotoxicity and the ability to inhibit urchin spermatozoids.…”

Distribution of Saponins in the Sea Cucumber Holothuria lessoni; the Body Wall Versus the Viscera, and Their Biological Activities

“…Triterpene glycosides of sea cucumber are known to possess a broad range of medicinal and physiological activities [ 10 , 11 ]. The medical potency of sea cucumber saponins exhibits plentiful health benefits due to their cardiovascular, ant-diabetic, hypoglycaemia, anti-oxidant, anti-asthma, anti-eczema, anti-inflammatory, anti-arthritic, anti-diabetics, cholesterol-lowering effect, immunomodulator, cytotoxic, anti-parasitic, anti-viral, antifungal [ 7 , 12 ], anticancer [ 13 , 14 ], anti-angiogenesis, anti-proliferative [ 15 ], and anti-dementia activities [ 2 ]. According to the literature, saponins also possess neuroprotective effects on the diminution of central nervous system disorders, namely Alzheimer’s disease, Huntington’s disease, Parkinson’s disease, and strokes [ 16 ].…”