Abstract
The edible portion of sea cucumber, body walls, is a source of natural bioactive compounds. Triterpene saponins are the main chemical constituents in sea cucumber that have potential interest for the body health and food industry. Twenty-one lanostane-type non-sulphated triterpene glycosides were isolated from the methanol/methylene chloride extract of the body walls of Bohadschia cousteaui. Ten new saponins called coustesides A (1), B (3), C (9), D (10), E (11), F (12), G (15), H (16), I (17) and J (18), including two pentasaccharide and eight hexasaccharide saponins, together with eleven known triterpene glycosides, were isolated by reversed-phase semi-preparative HPLC. Their structures were mainly determined by 1D- and 2D-NMR (1H, 13C, COSY, TOCSY, HSQC, HMBC and ROESY) as well as MS experiments and acid hydrolysis. Most of the isolated compounds showed good antifungal activity against Candida albicans. Moreover, sea cucumber B. cousteaui is a rich source of biologically active saponins. Therefore, sea cucumbers are eaten for their therapeutic values as a functional food than for their seafood taste.
Similar content being viewed by others
References
Webb GP (2006) An overview of dietary supplements and functional food. In dietary supplements and functional foods, 1st edn. Blackwell Publishing, Oxford, UK, pp 1–35
Shahidi F (2009) Nutraceuticals and functional foods: whole versus processed foods. Trends Food Sci Tech 20:376–387
Hu SY (2005) Food plants of China. Chinese University Press, Hong Kong, China, p 3–11, 275–278
Venugopal V (2009) Marine habitat and resources. In: Venugopal V (ed) Marine products for healthcare: functional and bioactive nutraceutical compounds from the ocean. CRC Press Taylor & Francis Group, Boca Raton, FL, pp 23–50
Lawrence AJ (2006) Darwin initiative for the sustainable use of sea cucumber in Egypt. Darwin Final Report Part 4 Oct 04
Chen J (2003) Overview of sea cucumber farming and sea ranching practices in China. SPC Beche-de-mer Inform Bull 18:18–23
Jiaxin C (2003) Overview of sea cucumber farming and sea ranching practices in China. SPC Beche-de-mer Inform Bull 18:1–6
Zhong Y, Khan MA, Shahidi F (2007) Compositional characteristics and antioxidant properties of fresh and processed sea cucumber (Cucumaria frondosa). J Agri Food Chem 55:1188–1192
Bordbar S, Anwar F, Saari N (2001) High-value components and bioactives from sea cucumbers for functional foods–A Review. Mar Drugs 9:1761–1805
Gurfinkel DM, Rao AV (2003) Soysaponins: the relationship between chemical structure and colon anticarcinogenic activity. Nutr Cancer 47:24–33
Kim SW, Park SK, Kang SI, Kang HC, Oh HJ, Bae CY, Bae DH (2003) Hypocholesterolemic property of Yucca schidigera and Quillaja saponaria extracts in human body. Arch Pharmacol Res 26:1042–1046
Özlem GÜ, Giuseppe M (2007) Saponins: properties, applications and processing. Crit Rev Food Sci Nutr 47:231–258
Elbandy M, Kang OH, Kwon DY, Rho JR (2009) Two new anti-inflammatory triterpene saponins from the Egyptian medicinal food black cumin (seeds of Nigella sativa). Bull Korean Chem Soc 30:1811–1816
Elbandy M, Ashoush I (2012) Phytochemicals in pomegranate seeds and their effect as hypolipidemic agent in hypercholesterolemic rats. World J Dairy Food Sci 7(1):85–92
Elbandy M, Rho JR, Afifi R. (2011) Analysis of triterpene saponins of the nutraceutical foods sea cucumber, (Bohadschia cousteaui) by using nuclear magnetic resonance and mass spectrometry. In Proceeding of ICFST‒ China 2011, 9th International Conference Food Science Technology, China: Hangzhou
Elbandy M, Miyamoto T, Delaude C, Lacaille-Dubois MA (2002) Five new medicagenic acid saponins from Muraltia ononidifolia. Helv Chim Acta 85:2721–2728
Naoki SA, Atsuko TB, Takako SC, Kazunori AD (2010) Development of an absolute quantification method for organic compounds using quantitative NMR (qNMR) and improvement of the reliability of food analysis. Tetrahedron 57:9563–9568
Xue RN, Fan L, Rieser MJ, El-Shourbagy TA (2007) Recent advances in high throughput quantitative bioanalysis by LC-MS/MS. J Pharmaceut Biomed Anal 44:342–355
NCCLS (2004) Method for antifungal disk diffusion susceptibility testing of yeasts; approved guideline. NCCLS document M44-A (ISBN 1-56238-532-1). NCCLS, 940 West Valley Road, Suite 1400, Wayne, Pennsylvania 19087-1898, USA
Van Rossum JMV (1963) The relation between chemical structure and biological activity–A Review. J Pharml Pharmacol 15(1):285–316
Kitagawa I, Kobayashi M, Inamoto T, Fuchida M, Kyogoku Y (1989) Marine natural products. XIV. Structures of echinosides A and B, antifungal lanostane oligosides from the sea cucumber Actinopyga echinities (Jaeger). Chem Pharma Bull 33:5214–5224
Kitagawa I, Kobayashi M, Hori M, Kyogoku Y (1985) Marine natural products. VIII. Four lanostane-type triterpene oligoglycosides, bivittosides A, B, C, and D, from the okinawan sea cucumber Bohadschia bivittata Mitsukuri. Chem Pharma Bull 37:61–67
Sun P, Liu BS, Yi YH, Li L, Gui M, Tang HF, Zhang DZ, Zhang SL (2007) A new cytotoxic lanostane-type triterpene glycoside from the sea cucumber Holothuria impatiens. Chem Biodivers 4:450–457
Stonik VA, Kalinin VI, Avilov SA (1999) Toxins from sea cucumbers (Holothuroids): chemical structures, properties, taxonomic distribution, biosynthesis and evolution. J Nat Toxins 8:235–248
Avilov SA, Kalinin VI, Smirnov AV (2004) Use of triterpene glycosides for resolving taxonomic problems in the sea cucumber genus Cucumaria (Holothurioidea, Echinodermata). Biochem Syst Ecol 32:715–733
Breitmaier E, Voelter W (1987) Carbon-13 NMR Spectroscopy. VCH, Weinheim
Liu BS, Yi YH, Li L, Sun P, Yuan WH, Sun GQ, Han H, Xue M (2008) Argusides B and C, two new cytotoxic triterpene glycosides from the sea cucumber Bohadschia argus Jaeger. Chem Biodivers 5:1228–1297
Kalinin VI, Silchenko AS, Avilov SA, Stonic VA, Smirnov AV (2005) Sea cucumber triterpene glycosides, the recent progress in structural elucidation and chemotaxonomy. Phytochem Rev 4:221–236
Wu J, Yi YH, Tang HF, Wu HM, Zhou ZR (2007) Hillasides A and B, two new cytotoxic triterpene glycosides from the sea cucumber Holothuria hilla Lesson. J Asian Nat Prod Res 9:609–615
Murray AP, Muniain C, Seldes AM, Maier MS (2001) Patagonicoside A: a novel antifungal disulfated triterpene glycoside from the sea cucumber Psolus patagonicus. Tetrahedron 57:9563–9568
Yuan WH, Yi YH, Tang HF, Liu BS, Wang ZL, Sun GQ, Zhang W, Li L, Sun P (2009) Antifungal triterpene glycosides from the sea cucumber Bohadschia marmorata. Planta Med 75:168–173
Sun GQ, Li L, Yi YH, Yuan WH, Liu BS, Weng YY, Zhang SL, Sun P, Wang ZL (2008) Two new cytotoxic nonsulfated pentasaccharide holostane (= 20-hydroxylanostan-18-oic acid γ-lactone) glycosides from the sea cucumber Holothuria grisea. Helv Chim Acta 91:145–1460
Yuan WH, Yi YH, Tan RX, Wang ZL, Sun GQ, Xue M, Zhang HW, Tang HF (2009) Antifungal triterpene glycosides from the sea cucumber Holothuria (Microthele) axiloga. Planta Med 75:647–653
Ohta T, Hikino H (1981) Structures of four new triterpenoidal oligoglycosides, bivittoside A, B, C and D from the sea cucumber Bohadschia bivittata Mitsukuri. Chem Pharma Bull 29:282–285
Dyck SV, Gerbaux P, Flammang P (2009) Elucidation of molecular diversity and body distribution of saponins in the sea cucumber Holothuria forskali (Echinodermata) by mass spectrometry. Comparative Biochem Physiol Part B 152:124–134
Conflict of interest
None.
Compliance with Ethics Requirements
This article does not contain any studies with human or animal subjects.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Elbandy, M., Rho, J.R. & Afifi, R. Analysis of saponins as bioactive zoochemicals from the marine functional food sea cucumber Bohadschia cousteaui . Eur Food Res Technol 238, 937–955 (2014). https://doi.org/10.1007/s00217-014-2171-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00217-014-2171-6