- Marine Natural Products. XVIII. Four Lanostane-Type Triterpene Oligoglycosides, Bivittosides A, B, C, and D, from the Okinawan Sea Cucumber Bohadschia bivittata MITSUKURI
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A full account of the structure elucidation of four lanostane-type triterpene oligoglycosides, bivittosides A (6), B (8), C (9), and D (10), is presented.Bivittosides were isolated from body-walls and Cuvierian tubules of the Okinawan sea cucumber Bohadschia bivittata MITSUKURI, and among these four oligoglycosides, bivittoside D (10) showed significant antifungal activities.Acidic hydrolysis of bivittosides A (6), B (8), and D (10) provided three artifact sapogenols, among which a homoannular-dienic sapogenol named preseychellogenin (4), exhibiting characteristically red-shifted ultraviolet and circular dichroism spectra, was identified as the monoacetate (4a).Keywords: sea cucumber; Bohadschia bivittata; bivittoside; lanostane-type triterpene oligoglycoside; homoannular-diene strained; oligoglycoside 13C-NMR; oligoglycoside T1; Turbo cornutus glycosidase; deoxybivittogenin; preseychellogenin
- Kitagawa, Isao,Kobayashi, Motomasa,Hori, Manabu,Kyogoku, Yoshimasa
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- MARINE NATURAL PRODUCTS. XIX. PERVICOSIDES A, B, AND C, LANOSTANE-TYPE TRITERPENE-OLIGOGLYCOSIDE SULFATES FROM THE SEA CUCUMBER HOLOTHURIA PERVICAX
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Triterpene-oligoglycoside constituents, contained in the body walls and the Cuvierian tubules of the sea cucumber Holothuria pervicax (torafu-namako in Japanese), were investigated and purified in their desulfated forms.These desulfated lanostane-type triterpene tetraglycosides, designated DS-pervicoside A (7), DS-pervicoside B (8), and DS-pervicoside C (9), have antifungal activity, and their structures were determined on the basis of chemical and physicochemical evidence.The parent oligoglycosides of these desulfated tetraglycosides, named pervicosides A (10), B (11), and C (12), were shown to be the 4'-sulfates of DS-pervicosides A (7), B (8), and C (9), respectively.Keywords: sea cucumber; Holothuria pervicax; oligoglycoside antifungal; lanostane-type triterpene oligoglycoside; oligoglycoside 13C-NMR; pervicoside A; pervicoside B; pervicoside C
- Kitagawa, Isao,Kobayashi, Motomasa,Son, Byeng Wha,Suzuki, Shigeki,Kyogoku, Yoshimasa
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p. 1230 - 1234
(2007/10/02)
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