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

Zhang,Jia-Jia; Zhu,Ke-Qi

doi:10.3892/etm.2017.4656

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

Authors:
- Jia-Jia Zhang
- Ke-Qi Zhu
View Affiliations

Affiliations: School of Pharmacy, Zhejiang Pharmaceutical College, Ningbo, Zhejiang 315100, P.R. China, Department of Traditional Chinese Internal Medicine, Ningbo No. 1 Hospital, Ningbo, Zhejiang 315010, P.R. China
Published online on: June 23, 2017 https://doi.org/10.3892/etm.2017.4656
Pages: 1653-1658

Metrics: Total Views: 0 (Spandidos Publications: | PMC Statistics: )

Metrics: Total PDF Downloads: 0 (Spandidos Publications: | PMC Statistics: )

Cited By (CrossRef): 0 citations Loading Articles...

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 C40H61O17SNa and chemical name 3‑O‑[‑β-D-pyranosyl (1-2)‑4'-O-sulfon-ate-β‑D‑xylopyranosyl]‑alkoxy‑9‑ene‑3β, 12α, 17α, 25β‑4 alcohol. 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 IC50 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.

View Figures

View References

1	Aminin DL, Menchinskaya ES, Pisliagin EA, Silchenko AS, Avilov SA and Kalinin VI: Anticancer activity of sea cucumber triterpene glycosides. Mar Drugs. 13:1202–1223. 2015. View Article : Google Scholar : PubMed/NCBI
2	Sun P, Liu BS, Yi YH, Li L, Gui M, Tang HF, Zhang DZ and Zhang SL: A new cytotoxic lanostane-type triterpene glycoside from the sea cucumber Holothuria impatiens. Chem Biodivers. 4:450–457. 2007. View Article : Google Scholar : PubMed/NCBI
3	Zou Z, Yi Y, Wu H, Yao X, Du L, Jiuhong W, Liaw CC and Lee KH: Intercedensides D-I, cytotoxic triterpene glycosides from the sea cucumber Mensamaria intercedens Lampert. J Nat Prod. 68:540–546. 2005. View Article : Google Scholar : PubMed/NCBI
4	Tong Y, Zhang X, Tian F, Yi Y, Xu Q, Li L, Tong L, Lin L and Ding J: Philinopside A, a novel marine-derived compound possessing dual anti-angiogenic and anti-tumor effects. Int J Cancer. 114:843–853. 2005. View Article : Google Scholar : PubMed/NCBI
5	Yu S, Ye X, Chen L, Xie X, Zhou Q, Lian XY and Zhang Z: Cytotoxic and anti-colorectal tumor effects of sulfated saponins from sea cucumber Holothuria moebii. Phytomedicine. 22:1112–1119. 2015. View Article : Google Scholar : PubMed/NCBI
6	Yu S, Ye X, Huang H, Peng R, Su Z, Lian XY and Zhang Z: Bioactive sulfated saponins from sea cucumber Holothuria moebii. Planta Med. 81:152–159. 2015. View Article : Google Scholar : PubMed/NCBI
7	Wu J, Yi YH, Tang HF, Wu HM, Zou ZR and Lin HW: Nobilisides A-C, three new triterpene glycosides from the sea cucumber Holothuria nobilis. Planta Med. 72:932–935. 2006. View Article : Google Scholar : PubMed/NCBI
8	Mona MH, Omran NE, Mansoor MA and El-Fakharany ZM: Antischistosomal effect of holothurin extracted from some Egyptian sea cucumbers. Pharm Biol. 50:1144–1150. 2012. View Article : Google Scholar : PubMed/NCBI
9	Shanskij YD, Ershov YA and Pechennikov VM: A method for evaluation of therapeutic dose of doxorubicin hydrochloride using breast tumor cell culture MCF-7. Bull Exp Biol Med. 148:464–467. 2009.(In English, Russian). View Article : Google Scholar : PubMed/NCBI
10	Liu X, Ye W, Mo Z, Yu B, Zhao S, Wu H, Che C, Jiang R, Mak TC and Hsiao WL: Five new Ocotillone-type saponins from Gynostemma pentaphyllum. J Nat Prod. 67:1147–1151. 2004. View Article : Google Scholar : PubMed/NCBI
11	Honey-Escandón M, Arreguín-Espinosa R, Solís-Marín FA and Samyn Y: Biological and taxonomic perspective of triterpenoid glycosides of sea cucumbers of the family Holothuriidae (Echinodermata, Holothuroidea). Comp Biochem Physiol B Biochem Mol Biol. 180:16–39. 2015. View Article : Google Scholar : PubMed/NCBI
12	Imir N, Aydemir E, Simsek E, Gokturk RS, Yesilada E and Fiskin K: Cytotoxic and immunomodulatory effects of Ebenus boissieri Barbey on breast cancer cells. Genet Mol Res. 15:2016. View Article : Google Scholar : PubMed/NCBI
13	Man S, Chai H, Qiu P, Liu Z, Fan W, Wang J and Gao W: Turmeric enhancing anti-tumor effect of Rhizoma paridis saponins by influencing their metabolic profiling in tumors of H22 hepatocarcinoma mice. Pathol Res Pract. 211:948–954. 2015. View Article : Google Scholar : PubMed/NCBI
14	Weng A, Thakur M, Beceren-Braun F, Bachran D, Bachran C, Riese SB, Jenett-Siems K, Gilabert-Oriol R, Melzig MF and Fuchs H: The toxin component of targeted anti-tumor toxins determines their efficacy increase by saponins. Mol Oncol. 6:323–332. 2012. View Article : Google Scholar : PubMed/NCBI
15	Bahrami Y and Franco CM: Structure elucidation of new acetylated saponins, Lessoniosides A B, C, D and E and non-acetylated saponins, Lessoniosides F and G, from the viscera of the sea cucumber Holothuria lessoni. Mar Drugs. 13:597–617. 2015. View Article : Google Scholar : PubMed/NCBI
16	Bahrami Y, Zhang W, Chataway T and Franco C: Structure elucidation of five novel isomeric saponins from the viscera of the sea cucumber Holothuria lessoni. Mar Drugs. 12:4439–4473. 2014. View Article : Google Scholar : PubMed/NCBI
17	Cui C, Cui N, Wang P, Song S, Liang H and Ji A: Sulfated polysaccharide isolated from the sea cucumber Stichopus Japonicus against PC12 hypoxia/reoxygenation injury by inhibition of the MAPK signaling pathway. Cell Mol Neurobiol. 35:1081–1092. 2015. View Article : Google Scholar : PubMed/NCBI
18	Yang Z, Sun J and Xu Z: Beneficial effects of rhodotorula sp. C11 on growth and disease resistance of juvenile japanese spiky sea cucumber Apostichopus Japonicus. J Aquat Anim Health. 27:71–76. 2015. View Article : Google Scholar : PubMed/NCBI
19	Nguyen TH and Kim SM: Alpha-Glucosidase inhibitory activities of fatty acids purified from the internal organ of sea cucumber Stichopus japonicas. J Food Sci. 80:H841–H847. 2015. View Article : Google Scholar : PubMed/NCBI
20	Guo Y, Ding Y, Xu F, Liu B, Kou Z, Xiao W and Zhu J: Systems pharmacology-based drug discovery for marine resources: An example using sea cucumber (Holothurians). J Ethnopharmacol. 165:61–72. 2015. View Article : Google Scholar : PubMed/NCBI