Two new pregnane glycosides from soft coral <i>Cladiella</i> <i>krempfi</i>

Huang, Xincheng; Deng, Zhiwei; Ofwegen, Leen van; Li, J.; Fu, Hongzheng; Zhu, Xiaobin; Lin, Wenhan

doi:10.1080/10286020500034782

Cited by 17 publications

(11 citation statements)

References 12 publications

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“…Steroidal metabolites of this group usually contain E-D-fucose [1-6]. However, D-L-fucopyranose was found earlier in steroidal glycosides from other marine organisms such as soft coral and marine sponges [15][16][17]. Therefore, we assumed by analogy with these compounds that the D-fucopyranose in plancisides B and D also had the L-form.…”

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Minor Steroidal Triglycoside Planciside D from the Tropical Starfish Acanthaster planci

et al. 2014

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A new steroidal glycoside called planciside D was isolated from the tropical starfish Acanthaster planci and assigned the structure (. Planciside D was a triglycoside containing two carbohydrate chains, which are rarely found in starfish. Its structure was established using 2D NMR spectroscopy and tandem mass spectrometry with electrospray ionization (ESI).Keywords: starfish, Acanthaster planci, glycoside, steroidal aglycon, NMR spectroscopy.Glycosides of polyhydroxysteroids and asterosaponins are the most common structural groups of starfish steroidal metabolites [1-6]. Glycosides of polyhydroxysteroids contain a highly oxidized aglycon with 3-10 hydroxyls and one, two, or rarely three monosaccharide residues located on C-3 (or C-15) of the steroid core and/or in the C-24 or C-26, C-28, and C-29 positions of the aglycon side chain. Asterosaponins are oligoglycosides containing, as a rule, a 3-O-sulfated ' 9(11) -3E,6D-dihydroxysteroidal aglycon and a carbohydrate chain of 5-6 monosaccharide residues located on C-6 of the aglycon. Starfish steroidal glycosides are usually found in extracts as complicated mixtures that are difficult to separate into the pure compounds. The majority of the minor components of these fractions are unstudied although certain biosynthesis features of them or other metabolites are related to their formation. Starfish steroidal glycosides are interesting not only because of their unusual chemical structures but also because of their broad spectra of biological properties, including embryotoxic, antifungal, antiviral, antibacterial, neuroprotective, and other types of activity [1-6].The starfish Acanthaster planci L. 1758 (Order Valvatida, Family Acanthasteridae) is distributed in tropical waters of the Indian and Pacific Oceans and preys primarily on reef-forming coral polyps. A. planci is one of the largest starfish and is known also by the name "crown of thorns" because its body is covered with numerous long sharp needles. The toxic properties of needles from this starfish are often associated with the presence of polar steroidal glycosides, mainly asterosaponins, in its tissues [1]. Polar steroidal compounds from A. planci were studied earlier by Japanese and Italian researchers.

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Minor Steroidal Triglycoside Planciside D from the Tropical Starfish Acanthaster planci

et al. 2014

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“…[6,7,8,9,10,11,12,13,14]. The soft coral Cladiella krempfi has been found to produce several types of metabolites including eunicellin-type diterpenoids [15,16,17] and pregnane-type steroids [18,19]. Our previous chemical investigation of the Formosan soft coral Cladiella krempfi also resulted in the isolation of a series of new eunicellin-type diterpenoids, krempfielins A–M [20,21,22].…”

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confidence: 99%

Krempfielins N–P, New Anti-Inflammatory Eunicellins from a Taiwanese Soft Coral Cladiella krempfi

et al. 2014

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Three new eunicellin-type diterpenoids, krempfielins N–P (1–3), were isolated from a Taiwanese soft coral Cladiella krempfi. The structures of the new metabolites were elucidated by extensive spectroscopic analysis and by comparison with spectroscopic data of related known compounds. Compound 3 exhibited activity to inhibit superoxide anion generation. Both 1 and3, in particular 1, were shown to display significant anti-inflammatory activity by inhibiting the elastase release in FMLP/CB-induced human neutrophils.

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“…The soft coral Cladiella krempfi has been found to generate several types of metabolites including eunicellin-type diterpenoids [15] and pregnane-type steroids [16,17,18]. Our previous chemical investigation of C. krempfi had led to the isolation of four new eunicellin-based diterpenoids, krempfielins A–D [19].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic and Anti-Inflammatory Eunicellin-Based Diterpenoids from the Soft Coral Cladiella krempfi

Tai

Huang

et al. 2013

Marine Drugs

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Five new eunicellin-based diterpenoids, krempfielins E–I (1–5) and seven known compounds (6–12) were isolated from the organic extract of a Taiwanese soft coral Cladiella krempfi. The structures of the new metabolites were elucidated on the basis of extensive spectroscopic analysis. Metabolites 5, 6, 10 and 12 were shown to exhibit cytotoxicity against a limited panel of cancer cell lines. Furthermore, compounds 6 and 10 could potently inhibit the accumulation of the pro-inflammatory iNOS protein, and 6 and 12 could significantly reduce the expression of COX-2 protein in LPS-stimulated RAW264.7 macrophage cells.

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Two new pregnane glycosides from soft coral Cladiella krempfi

Cited by 17 publications

References 12 publications

Minor Steroidal Triglycoside Planciside D from the Tropical Starfish Acanthaster planci

Minor Steroidal Triglycoside Planciside D from the Tropical Starfish Acanthaster planci

Krempfielins N–P, New Anti-Inflammatory Eunicellins from a Taiwanese Soft Coral Cladiella krempfi

Cytotoxic and Anti-Inflammatory Eunicellin-Based Diterpenoids from the Soft Coral Cladiella krempfi

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