Free sterol compositions from the sea cucumbers Pseudostichopus trachus, Holothuria (Microtele) nobilis, Holothuria scabra, Trochostoma orientale and Bathyplotes natans

Stonik, V. A.; Ponomarenko, L. P.; Makarieva, Tatiana N.; Boguslavsky, Valentine M; Dmitrenok, A. S.; Fedorov, Sergey N.; Strobikin, Sergei A

doi:10.1016/s0305-0491(98)10023-8

Cited by 36 publications

(32 citation statements)

References 31 publications

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“…El análisis estructural de los esteroles identificados a partir de M. quinquiesperforata, permitió establecer que el núcleo predominante en este tipo de estructuras es el núcleo Δ 5 mono y diinsaturado con un porcentaje de abundancia de 87,5%, este tipo de núcleos ya han sido establecidos como núcleos predominantes en equinodermos (Kanazawa 2001, Pérez et al 1996, Stonik et al 1998. Asimismo, se observó otra característica marcada del filum equinodermata, como lo es alto contenido de esteroles con sustituciones en C 24 de la cadena lateral (Iorizzi 1995, Kanazawa 2001, el cual fue del 50% para M. quinquiesperforata.…”

Section: Discussionunclassified

Actividad antioxidante del erizo de mar Mellita quinquiesperforata (Leske) e identificación de sus compuestos lipídicos mayoritarios

2016

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Section: Discussionunclassified

Actividad antioxidante del erizo de mar Mellita quinquiesperforata (Leske) e identificación de sus compuestos lipídicos mayoritarios

2016

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“…Only some echinoderms (Holuthurians) contain significant amounts of these sterols [19,20]. For example, in Holothuria scabra, 4␣,14␣-dimethyl-5␣-cholest-9(11)-en-3␤-ol and 4␣,14␣-dimethyl-5␣-cholest-7-en-3␤-ol were identified as major components of the sterol fraction [21]. However, at this stage of investigation, it would be premature to conclude that 4,14-dimethylcholestane is a specific biomarker for echinoderms.…”

Section: Origins Of 414-dimethylcholestanementioning

confidence: 99%

Combination of gas chromatography–mass spectrometry and mass spectral deconvolution for structural elucidation of an unusual C29-steroid detected in a complex sedimentary matrix

Finck

Aydin

Pellaton

et al. 2004

Journal of Chromatography A

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A complex sedimentary sample from the Monterey Formation (CA, USA) has been submitted to GC-MS analysis followed by mass spectral deconvolution using Automated Mass Spectral Deconvolution and Identification System (AMDIS). Adjusting the parameters of the software allowed for the extraction of the spectrum of an unusual steroidal hydrocarbon coeluting with the major compound of the chromatogram. Following a careful interpretation of the "extracted" mass spectrum, the structure of the unknown has been postulated to be the 4,14-dimethylcholestane (DMC). Possible origins of this rare steroid are briefly discussed. Thus, application of AMDIS appears to be particularly suitable for the GC-MS analysis of natural complex mixtures characterized by a high number of analytes present in low amounts.

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“…They differ from cholesterol either by the position of the double bond in the steroid core (sometimes its absence) [2][3][4] or by the presence of highly alkylated side chains [5,6]. According to a hypothesis proposed by us, the unusual sterols protect the biomembranes of toxin-producing marine invertebrates from the lytic action of their own toxins as a result of sterol-toxin biochemical coordination occurring in such instances [7].…”

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confidence: 99%

“…A part (0.215 g) of this total was chromatographed over a column of silica gel (KSK, 50-160 Pm) using a hexaneoEtOAc gradient (4:1) to afford the total sterol fraction (57 mg, 0.92% of dry wt) that was separated using HPLC into three subfractions consisting of ' 5 -(1.3 mg) and ' 7 -sterols (24.3 mg), and stanols (21 mg). These were analyzed using PMR as described before [2,3,9,10].The structures of the free sterols as the acetylated derivatives were identified using GC and comparison with the relative retention times (RRT) of standard sterols and using GC-MS as before [2,3,9,10]. Table 1 presents the results.…”

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confidence: 99%

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Sterols from the toxin-containing far-east sponge Monanchora pulchra

2012

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It was shown earlier that toxin-containing marine invertebrates, in particular sponges (phylum Porifera) and sea cucumbers (phylum Echinodermata, class Holothurioidea), often contain unusual sterols instead of cholesterol and other ' 5 -sterols, in contrast with other animals [1]. They differ from cholesterol either by the position of the double bond in the steroid core (sometimes its absence) [2][3][4] or by the presence of highly alkylated side chains [5,6]. According to a hypothesis proposed by us, the unusual sterols protect the biomembranes of toxin-producing marine invertebrates from the lytic action of their own toxins as a result of sterol-toxin biochemical coordination occurring in such instances [7].In continuation of the search for new sources of biologically active compounds among invertebrates of Far-East seas, we recently found that EtOH extracts of the sponge Monanchora pulchra exhibited high cytotoxic activity. It was shown that this sponge contained a new cytotoxic polycyclic guanidine alkaloid that we called monanchocidin [8]. We investigated the sterol fraction from this sponge collected near the shores of Urup Is. (Kuril Islands, 46°07.0 N, 150°02 E) in August 2008 in order to test further this hypothesis.The sponge for chemical investigation was stored at -20°C. Thawed ground biological material (18.9 g dry wt.) was extracted (3u) with EtOH. The combined extracts were concentrated to dryness in vacuo and distributed between H 2 O and BuOH. The evaporated BuOH layer (2.14 g) was dissolved in EtOH (90%) and extracted (3u) with hexane. The combined hexane layers were concentrated to afford total nonpolar substances (0.69 g). A part (0.215 g) of this total was chromatographed over a column of silica gel (KSK, 50-160 Pm) using a hexaneoEtOAc gradient (4:1) to afford the total sterol fraction (57 mg, 0.92% of dry wt) that was separated using HPLC into three subfractions consisting of ' 5 -(1.3 mg) and ' 7 -sterols (24.3 mg), and stanols (21 mg). These were analyzed using PMR as described before [2,3,9,10].The structures of the free sterols as the acetylated derivatives were identified using GC and comparison with the relative retention times (RRT) of standard sterols and using GC-MS as before [2,3,9,10]. Table 1 presents the results. Table 1 shows that the sterol fraction from the studied sponge contained 29 previously known C 26 , C 27 , C 28 , C 29 , and C 30 compounds that had double bonds in the ' 7 , ' 7,22 , ' 7,24(28) , ' 0 , ' 22 , ' 5 , ' 5,22 , and ' 5,24(28) positions. Sterols of the ' 7 series were basic and made up 52.1% of the total sterol fraction. The stanol content was 45.1% whereas ' 5 -sterols were a minor fraction with a content of 2.8%. The principal components of the fraction were identified as 5-D-cholestan-3E-ol and 5D-cholest-7-en-3E-ol. Thus, yet another instance of toxin-(unusual sterols) biochemical coordination was found.

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Free sterol compositions from the sea cucumbers Pseudostichopus trachus, Holothuria (Microtele) nobilis, Holothuria scabra, Trochostoma orientale and Bathyplotes natans

Cited by 36 publications

References 31 publications

Actividad antioxidante del erizo de mar Mellita quinquiesperforata (Leske) e identificación de sus compuestos lipídicos mayoritarios

Actividad antioxidante del erizo de mar Mellita quinquiesperforata (Leske) e identificación de sus compuestos lipídicos mayoritarios

Combination of gas chromatography–mass spectrometry and mass spectral deconvolution for structural elucidation of an unusual C29-steroid detected in a complex sedimentary matrix

Sterols from the toxin-containing far-east sponge Monanchora pulchra

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