Structure of a novel steroidal saponin, pachastrelloside A, obtained from a marine sponge of the genus pachastrella

Harada, Hiroshi; Takayama, Seiji; Miyashiro, Shigeyoshi; Ozaki, Yoshihiro; Ikegami, Susumu

doi:10.1016/s0040-4039(00)89054-1

Cited by 31 publications

(26 citation statements)

References 10 publications

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“…Hence, the isolation of the 7α-glycoside 7 (paschastrelloside A) from Paschastrella sp . confirms a biotic origin of the 7α oxygen [21]. The novel feature of 7 is its 2α-OH; the sterol inhibits cell division of fertilized starfish eggs.…”

Section: General Biosynthetic Reactions In Marine Spongesmentioning

confidence: 88%

Sterol Ring System Oxidation Pattern in Marine Sponges

2005

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Abstract:The marine sponges (Porifera) are a unique group of sedentary organisms from which several novel natural products are reported, many of which have useful biological activities. In producing unusual sterols, they occupy a preeminent position among the various groups of organisms. The polar sterols of sponges reported as at the end of the year 2002 number about 250; their ring structure changing a hundred times. The oxidation pattern in the sterol ring system, from the point of view of biogenesis seems to be mainly of four types. Each sponge species is able to produce sterols fitting into one of the four main biogenetic pathways viz., (i) 3β-hydroxy-∆ 5 -sterol pathway, (ii) 3β-hydroxy-∆ 7 -sterol pathway, (iii) 3β-hydroxy-∆ 5,7 -sterol pathway, and (iv) 3α-hydroxy sterol pathway.

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Section: General Biosynthetic Reactions In Marine Spongesmentioning

confidence: 88%

Sterol Ring System Oxidation Pattern in Marine Sponges

2005

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“…Pachastrelloside A ( 139 ) inhibited cell division of fertilized starfish ( Asterina pectinifera ) eggs at 35 μM [134]. …”

Section: Triterpenes (C30)mentioning

confidence: 99%

“…To the best of our knowledge, around 80 sponge triterpenoidal glycosides have been reported to date, including erylosides [ 107 – 114 ], formosides [ 115 , 116 ], nobiloside [ 117 ], and sokodosides [ 118 ] from different sponge species of the genus Erylus ; sarasinosides from the marine sponges Asteropus sarasinosum [ 120 – 123 ], Melophlus isis [ 124 ], and M. sarassinorum [ 125 ]; mycalosides from Mycale laxissima [ 126 – 128 ]; ectyoplasides and feroxosides from the Caribbean marine sponge Ectyoplasia ferox [ 129 , 130 ]; ulososides from Ulosa sp. [ 131 , 132 ]; wondosterols from a two-sponge association [ 133 ]; and pachastrelloside A from a marine sponge of the genus Pachastrella [ 134 ]. The majority of these glycosides belong to norlanostane-triterpenoidal saponins, derived from lanosterol or related triterpenes as a result of oxidative elimination of one or two methyl groups.…”

Section: Triterpenes (C 30 )mentioning

confidence: 99%

“…Pachastrelloside A ( 139 ) was obtained from the marine sponge Pachastrella sp. (Kagami Bay, Japan) and revealed the presence of a cholest-5,24-diene-2 α ,3 β ,4 β ,7 α -tetraol aglycone that was glycosylated at the C-4 and C-7 positions with β -D-xylopyranose and β -D-galactopyranose moieties, respectively [ 134 ].…”

Section: Triterpenes (C 30 )mentioning

confidence: 99%

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Bioactive Sesterterpenes and Triterpenes from Marine Sponges: Occurrence and Pharmacological Significance

2010

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Marine ecosystems (>70% of the planet’s surface) comprise a continuous resource of immeasurable biological activities and immense chemical entities. This diversity has provided a unique source of chemical compounds with potential bioactivities that could lead to potential new drug candidates. Many marine-living organisms are soft bodied and/or sessile. Consequently, they have developed toxic secondary metabolites or obtained them from microorganisms to defend themselves against predators [1]. For the last 30–40 years, marine invertebrates have been an attractive research topic for scientists all over the world. A relatively small number of marine plants, animals and microbes have yielded more than 15,000 natural products including numerous compounds with potential pharmaceutical potential. Some of these have already been launched on the pharmaceutical market such as Prialt® (ziconotide; potent analgesic) and Yondelis® (trabectedin or ET-743; antitumor) while others have entered clinical trials, e.g., alpidin and kahalalide F. Amongst the vast array of marine natural products, the terpenoids are one of the more commonly reported and discovered to date. Sesterterpenoids (C25) and triterpenoids (C30) are of frequent occurrence, particularly in marine sponges, and they show prominent bioactivities. In this review, we survey sesterterpenoids and triterpenoids obtained from marine sponges and highlight their bioactivities.

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“…However, a number of these compounds have been recently isolated from sponges. [3][4][5][6][7][8][9][10][11][12][13][14][15][16] Of the sponge derived saponins, those possessing the lanostane-based penasterol or structurally related aglycones are mainly found in animals of the genus Erylus (order Choristida, family Geodiidae). 12…”

Section: Introductionmentioning

confidence: 99%

Bioactive Metabolites from Sponges -New Triterpenoid Saponins from the Sponge <i>Erylus nobilis</i>

2002

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Four new triterpenoid saponins, erylosides G-J (1-4), were isolated from the sponge Erylus nobilis collected from Jaeju Island, Korea. Based upon the results of combined chemical and spectral analyses, the structures of the aglycones were determined to be lanostane-based, modified penasterols. The oligosaccharide portions were composed of one unit each of L-arabinose, o-galactose, and 2-N-acetyl-o-glucosamine (1 and 3) or two units of L-arabinose and one unit of 2-N-acetyl-D-glucosamine (2 and 4). These compounds exhibited moderate cytotoxicity against a human leukemia cell-line K562.

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Structure of a novel steroidal saponin, pachastrelloside A, obtained from a marine sponge of the genus pachastrella

Cited by 31 publications

References 10 publications

Sterol Ring System Oxidation Pattern in Marine Sponges

Sterol Ring System Oxidation Pattern in Marine Sponges

Bioactive Sesterterpenes and Triterpenes from Marine Sponges: Occurrence and Pharmacological Significance

Bioactive Metabolites from Sponges -New Triterpenoid Saponins from the Sponge <i>Erylus nobilis</i>

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