A Bioactive Secosterol with an Unusual A- and B-Ring Oxygenation Pattern Isolated from an Indonesian Soft Coral <i>Lobophytum </i>sp.

Morris, Linda A.; Christie, E M; Jaspars, Marcel; Ofwegen, L.P. van

doi:10.1021/np9705118

Cited by 47 publications

(42 citation statements)

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“…Since the first isolation of 9,11-secosterol from the gorgonian Pseudopterogorgia americana in 1972 [1], the members of this type of interesting sterol have increased very quickly and over scores of them have been discovered up to now, from a great variety of marine organisms involving acidians [2], sponges [3], gorgonians [4][5][6][7][8], and particularly soft corals [9][10][11][12][13][14][15][16][17]. Characterized by bond cleavage between C-9 and C-11, 9,11-secosterols have attracted much attention from chemists and pharmacologists due to their versatile biological effects such as antiviral, antimicrobial, cytotoxic, antiinflammatory activities [2,4,[7][8][9][10][14][15][16][17].…”

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confidence: 99%

9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa

et al. 2015

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Section: Introductionmentioning

confidence: 99%

9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa

et al. 2015

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“…Likewise, 13,14-secosteroids have been isolated from terrestrial plants (Bhandari et al 2006;Kirson et al 1976;Qiu et al 2008) and some of which have been demonstrated to possess anti-inflammatory activities (Qiu et al 2008). 9,11-Secosterols, the third group of secosteroids, are very rare in terrestrial organisms, and are instead of found primarily in marine invertebrates, mainly corals (Huang et al 2012;Cheng et al 2011;Chen et al 2011a, b;Ioannou et al 2009;Minh et al 2007;Epifanio et al 2007;Su et al 2006;Anta et al 2002;Aknin et al 1998;Morris et al 1998;He et al 1995;Lopp et al 1994;Koljak et al 1993;Ochi et al 1991;Fusetani et al 1989;Bonini et al 1983) and sponges (Van Altena et al 1999;De Rosa et al 1999;Rueda et al 1998;Lu and Faulkner 1997;Reddy et al 1997;Adinolfi et al 1994;Li et al 1994;Migliuolo et al 1992, Migliuolo et al 1991Capon and Faulkner 1985). In addition, 9,11-secosterols have been reported to display diverse bioactivities including cytotoxicity against cancer cell lines (Huang et al 2012;Cheng et al 2011;Chen et al 2011a, b;Su et al 2006;Morris et al 1998;Rueda et al 1998), anti-proliferative effects Inho Yang and Hyukjae Choi have contributed equally to this work.…”

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confidence: 99%

A new 9,11-secosterol with a 1,4-quinone from a Korean marine sponge Ircinia sp.

Yang

Choi

Nam³

et al. 2015

Arch. Pharm. Res.

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An intensive investigation of chemical components for Ircinia sp. led to the isolation of a new 9,11-secosterol. The chemical structure of this compound was elucidated based on the interpretation of NMR and MS spectroscopic data. The isolated compound exhibited antibacterial activities against Staphylococcus epidermidis and Bacillus subtilis with MIC values of 6.3 and 25 μg ml(-1), respectively.

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“…Earlier studies of the genus Lobophytum have led to the isolation of terpenoids, of which some have shown cytotoxic, [7][8][9][10] anti-HIV, 11) and antibacterial 12) activities. In this paper we report the isolation and structural elucidation of three new glycolipids 1-3 (Fig.…”

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Glycolipids from the Formosan Soft Coral Lobophytum crassum

Chao

Huang

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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During the course of our investigation on the bioactive chemical constituents from marine invertebrates, [1][2][3][4][5][6] we have investigated a soft coral Lobophytum crassum collected from Taiwanese waters. Earlier studies of the genus Lobophytum have led to the isolation of terpenoids, of which some have shown cytotoxic, [7][8][9][10] anti-HIV, 11) and antibacterial 12) activities. In this paper we report the isolation and structural elucidation of three new glycolipids 1-3 (Fig. 1) from this organism. The absolute configurations of 1-3 were determined by the comparison of specific optical rotations of sugar and aglycon moieties with known compounds, chemical conversions, and the application of Mosher's method. Cytotoxicity of metabolites 1-3 against the growth of a limited panel of cancer cells of HepG2, Hep3B (human liver carcinoma), MDA-MB-231 (human breast carcinoma), and Ca9-22 (human gingival carcinoma) is also discussed. Results and Discussion(2R)-1-Hydroxy-3-hexadecyloxy-propyl-b -D-arabinopyranoside (1) was isolated as amorphous white solid. Its HR-ESI-MS exhibited a pseudomolecular ion peak at m/z 471.3296 [MϩNa] ϩ (Calcd for C 24 H 48 O 7 Na, 471.3298), corresponding to the molecular formula C 24 H 48 O 7 , indicating one degree of unsaturation. The 1 : 2 ratio of carbon and proton atoms and high oxygen content in its molecular formula and strong absorption bands at n max 3391, 1142, 1075, and 1007 cm Ϫ1 in IR spectrum suggested that 1 might be a glycolipid. An anomeric glycoside proton resonance was observed at d 5.67 (1H, d, Jϭ3.3 Hz), corresponding to a carbon resonance at d 100.4 (d) in the HMQC spectrum. Except for the above carbon (C-1Ј), the 13 C-NMR spectrum of 1 exhibited eight oxygenated carbons, including four oxymethylenes at d C 71.7 (t), 71.1 (t), 64.5 (t), and 63.0 (t), and four oxymethines at d C 78.5 (d), 71.0 (d), 70.8 (d), and 70.1 (d) ( Table 1). Above data together with the methyl group resonanting at d H 0.85 (3H, t, Jϭ6.6 Hz) and methylenes at d H 1.26 (br s) revealed the structure of 1 to be a glycoside with a long aliphatic chain.The gross structure of metabolite 1 was further established by the 2D-NMR studies, particularly in 1 H-1 H COSY, HMQC and HMBC experiments. The correlations of 1 H-1 H COSY revealed proton-proton sequences, from H-1Ј to H-5Ј, H 2 -1 to H 2 -3, H 2 -1Љ to H 2 -2Љ, and H 2 -15Љ to H 3 -16Љ, as shown in Fig. 2. The HMBC correlations from H-1Ј to C-5Ј and C-2, as well as other correlations illustrated in Fig. 2, established a pyranose and a glycerol ether moiety. The pyranose was identified as b-arabinopyranose by analysis of coupling constants of the related protons (Table 1). HR-ESI mass spectrum and the above 2D-NMR spectroscopic analysis led to the establishment of the aglycon to be chimyl alcohol.The absolute configurations on the sugar portion and lipid aglycon were determined on the basis of methanolysis, chemical transformation and the application of the modified Mosher's method. As shown in Chart 1, methanolysis of 1 with 1 N HCl (aq) -MeOH...

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A Bioactive Secosterol with an Unusual A- and B-Ring Oxygenation Pattern Isolated from an Indonesian Soft Coral Lobophytum sp.

Cited by 47 publications

References 7 publications

9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa

9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa

A new 9,11-secosterol with a 1,4-quinone from a Korean marine sponge Ircinia sp.

Glycolipids from the Formosan Soft Coral Lobophytum crassum

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