Phytochemical analysis of Holothuria leucospilota, a sea cucumber from Persian Gulf

Sea cucumbers are widely consumed in traditional medicine and food. These animals have a considerable secondary metabolite and also several potential biological activities. This study investigated the phytochemical and cytotoxic evaluation of Holothuria leucospilota (H. leucospilota), a sea cucumber from Persian Gulf. The saponin composition of H. leucospilota was studied by different partitioning and chromatography methods such as thin layer chromatography (TLC), medium pressure liquid chromatography (MPLC) and high performance LC (HPLC). The marine sea cucumber Holostane-type triterpenoids (1-3) were characterized by physical and spectroscopic examination (1 and 2 dimensional neuclear magnetic resonance and mass experiments) with data analysis. The structure of compounds 1-3 identified as echinoside A, holothurine A, and 24-dehydroechinoside A, showed moderate cytotoxic activity with IC50 values of 1.9 ± 0.07, 6.8 ± 0.23, and 2.57 ± 0.18 μ/mL against HeLa and 10.4 ± 0.32, 8.9 ± 0.24, and 4.4 ± 0.13 on HUVEC cell line, respectively. In conclusion, the holostane-type triterpenoids showed moderate cytotoxic activity against HeLa cell line and have a prosperous future to be introduced as a lead structure.

[1]  V. Lanzotti,et al.  Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber Holothuria atra , 2019, Marine drugs.

[2]  W. Xia,et al.  Anticancer effects of echinacoside in hepatocellular carcinoma mouse model and HepG2 cells , 2018, Journal of cellular physiology.

[3]  Tiantian Zhang,et al.  Saponins from Sea Cucumber and Their Biological Activities. , 2018, Journal of agricultural and food chemistry.

[4]  Jiajing Niu,et al.  Echinacoside Induces Apoptosis in Human SW480 Colorectal Cancer Cells by Induction of Oxidative DNA Damages , 2015, International journal of molecular sciences.

[5]  M. Diederich,et al.  A Survey of Marine Natural Compounds and Their Derivatives with Anti-Cancer Activity Reported in 2012 , 2015, Molecules.

[6]  C. Xue,et al.  Effects of two sulfated triterpene saponins echinoside A and holothurin A on the inhibition of dietary fat absorption and obesity reduction , 2014, Bioscience, biotechnology, and biochemistry.

[7]  P. Gerbaux,et al.  When a repellent becomes an attractant: harmful saponins are kairomones attracting the symbiotic Harlequin crab , 2013, Scientific Reports.

[8]  Y. Jeon,et al.  Anticancer activity and mediation of apoptosis in human HL-60 leukaemia cells by edible sea cucumber (Holothuria edulis) extract. , 2013, Food chemistry.

[9]  M. Vazzana,et al.  Immune mediators of sea-cucumber Holothuria tubulosa (Echinodermata) as source of novel antimicrobial and anti-staphylococcal biofilm agents , 2013, AMB Express.

[10]  Yong Xue,et al.  In vitro and in vivo anti-tumour activities of echinoside A and ds-echinoside A from Pearsonothuria graeffei. , 2012, Journal of the science of food and agriculture.

[11]  Jinhua Zhao,et al.  Structure and effect of sulfated fucose branches on anticoagulant activity of the fucosylated chondroitin sulfate from sea cucumber Thelenata ananas. , 2012, Carbohydrate polymers.

[12]  Farooq Anwar,et al.  High-Value Components and Bioactives from Sea Cucumbers for Functional Foods—A Review , 2011, Marine drugs.

[13]  Yong Xue,et al.  Ds-echinoside A, a new triterpene glycoside derived from sea cucumber, exhibits antimetastatic activity via the inhibition of NF-κB-dependent MMP-9 and VEGF expressions , 2011, Journal of Zhejiang University SCIENCE B.

[14]  I. Fournier,et al.  The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish , 2011, Journal of Experimental Biology.

[15]  Yong Xue,et al.  Differential effects of sulfated triterpene glycosides, holothurin A1, and 24-dehydroechinoside A, on antimetastasic activity via regulation of the MMP-9 signal pathway. , 2010, Journal of food science.

[16]  Zhong‐Ji Qian,et al.  Sea cucumber, Stichopus japonicus ethyl acetate fraction modulates the lipopolysaccharide induced iNOS and COX-2 via MAPK signaling pathway in murine macrophages. , 2010, Environmental toxicology and pharmacology.

[17]  Wen Zhang,et al.  A Novel Sulfated Holostane Glycoside from Sea Cucumber Holothuria leucospilota , 2010, Chemistry & biodiversity.

[18]  Z. Miao,et al.  Echinoside A, a new marine-derived anticancer saponin, targets topoisomerase2alpha by unique interference with its DNA binding and catalytic cycle. , 2010, Annals of oncology : official journal of the European Society for Medical Oncology.

[19]  P. Gerbaux,et al.  Qualitative and Quantitative Saponin Contents in Five Sea Cucumbers from the Indian Ocean , 2010, Marine drugs.

[20]  P. Boiron,et al.  Antifungal activity of aqueous and methanolic extracts from the Mediterranean sea cucumber, Holothuria polii , 2008 .

[21]  M. Zeng,et al.  Antihypertensive effect and purification of an ACE inhibitory peptide from sea cucumber gelatin hydrolysate , 2007 .

[22]  V. Sepe,et al.  Isolation and Structural Elucidation of Callipeltins J—M: Antifungal Peptides from the Marine Sponge Latrunculia sp. , 2007 .

[23]  E. Pelletier,et al.  Quantification of phenolic contents and antioxidant capacity of Atlantic sea cucumber, Cucumaria frondosa , 2007 .

[24]  Paul R Jensen,et al.  Developing a new resource for drug discovery: marine actinomycete bacteria , 2006, Nature chemical biology.

[25]  Jian Ding,et al.  PE, a new sulfated saponin from sea cucumber, Exhibits anti-angiogenic and anti-tumor activities in vitro and in vivo , 2005, Cancer biology & therapy.

[26]  V. Kalinin.  System-theoretical (Holistic) approach to the modelling of structural-functional relationships of biomolecules and their evolution: an example of triterpene glycosides from sea cucumbers (Echinodermata, holothurioidea). , 2000, Journal of theoretical biology.

[27]  H. Wang,et al.  Basic and clinical study on the antithrombotic mechanism of glycosaminoglycan extracted from sea cucumber. , 2000, Chinese medical journal.

[28]  R. Lill,et al.  The discovery and development of marine compounds with pharmaceutical potential. , 1999, Journal of biotechnology.

[29]  D. Faulkner.  Marine natural products: metabolites of marine invertebrates , 1984 .