Antifungal Triterpene Glycosides from the Sea Cucumber Bohadschia marmorata

Abstract

Four new holostan-type triterpene glycosides, marmoratoside A (1), 17α-hydroxy impatienside A (2), marmoratoside B (3), 25-acetoxy bivittoside D (4), together with two known triterpene glycosides, impatienside A (5) and bivittoside D (6), were isolated from the sea cucumber Bohadschia marmorata Jaeger. On the basis of spectroscopic analyses, including two-dimensional NMR techniques, and chemical reactions, the structures of the new triterpene glycosides were elucidated. Compounds 1, 2, 5, and 6 exhibited significant antifungal activity against six strains (0.70 ≤ MIC₈₀ ≤ 2.81 μM).

Key words

sea cucumber - Bohadschia marmorata - triterpene glycoside - antifungal

References

• 1 Kitagawa I, Kobayashi M, Hori M, Kyogoku Y. Marine natural products. VIII. Four lanostane-type triterpene oligoglycosides, bivittosides A, B, C, and D, from the okinawan sea cucumber Bohadschia bivittata Mitsukuri.  Chem Pharm Bull. 1989;  37 61-7
• 2 Zou Z R, Yi Y H, Wu H M, Yao X S, Du L J, Wu J H. et al . Intercedensides D-I, cytotoxic triterpene glycosides from the sea cucumber Mensamaria intercedens Lampert.  J Nat Prod. 2005;  68 540-6
• 3 Stonik V A, Elyakov G B. Bioorganic marine chemisty. Berlin; Springer 1988: 43
• 4 Sun P, Liu B S, Yi Y H, Li L, Gui M, Tang H F. et al . A new cytotoxic lanostane-type triterpene glycosides from the sea cucumber Holothuria impatiens. .  Chem Biodivers. 2007;  4 450-7
• 5 Zhang S Y, Tang H F, Yi Y H. Cytotoxic triterpene glycosides from the sea cucumber Pseudocolochirus violaceus. .  Fitoterapia. 2007;  78 283-7
• 6 Han H, Yi Y H, Li L, Wang X H, Liu B S, Sun P. et al . A new triterpene glycosides from the sea cucumber Holothuria leucospilota. .  Chin Chem Lett. 2007;  18 161-4
• 7 Zhang S Y, Yi Y H, Tang H F. Bioactive triterpene glycosides from the sea cucumber Holothuria fuscocinerea. .  J Nat Prod. 2006;  69 1492-5
• 8 Zou Z R, Yi Y H, Wu H M, Wu J H, Liaw C C, Lee K H. Intercedensides A-C, three new cytotoxic triterpene glycosides from the sea cucumber Mensamaria intercedens Lampert.  J Nat Prod. 2003;  66 1055-60
• 9 Zhang J D, Xu Z, Cao Y B, Chen H S, Yan L, An M M. et al . Antifungal activities and action mechanisms of compounds from Tribulus terrestris L.  J Ethnopharmacol. 2006;  103 76-84
• 10 Ohta T, Hikino H. Structures of four new triterpenoidal oligoglycosides, bivittosides A, B, C, and D, from sea cucumber Bohadschia bivittata Mitsukuri.  Chem Pharm Bull. 1981;  29 282-5
• 11 Kitagawa I, Kobayashi M, Inamoto T, Fuchida M, Kyogoku Y. Marine natural products. XIV.  Structures of echinosides A and B, antifungal lanostane-oligosides from the sea cucumber Actinopyga echinites (Jaeger). Chem Pharm Bull. 1985;  33 5214-24
• 12 Murray A P, Muniain C, Seldes A M, Maier M S. Patagonicoside A: a novel antifungal disulfated triterpene glycoside from the sea cucumber Psolus patagonicus. .  Tetrahedron. 2001;  57 9563-8