Steroid compounds of marine sponges. III. 24-Ethyl-25-methylcholesta-5,22-dien-3β-OL — A new marine sterol from the spongeHalichondria sp.

Shubina, Larisa K.; Makar’eva, T. N.; Stonik, V. A.

doi:10.1007/bf00574330

Cited by 5 publications

(7 citation statements)

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“…These data show that 1 possessed a cholesta skeleton having two double bonds, one hydroxyl and one methoxyl. Two double bonds were assigned to be located between C-5 and C-6, as well as C-23 and C-24, by comparison of chemical shifts and coupling constants of three olefinic proton signals with that of a related compound [12,13]. The assignment was further confirmed by HMBC experiment (Fig.…”

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confidence: 55%

Steroids from the marine bryozoan Bugula neritina

et al. 2010

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Keywords: marine bryozoan, Bugula neritina, 3E-hydroxy-25-methoxy-(23E)-cholesta-5,23-dien, sterols.The marine bryozoan Bugula neritina L. is one of the most prominent bryozoans among the common fouling organisms, with a broad geographic range in the Atlantic, Pacific, and other areas. Since the discovery of their medical potential in 1968, a series of macrocyclic lactones termed bryostatins 1-20 and neristatins 1-2 [1-11] have been isolated from this bryozoan, while only a few reports on the steroids exist.We previously reported the isolation of bryostatins from this animal and discovered a new antineoplastic macrolide, bryostatin 19 [10]. A further investigation on the steroids from the petroleum ether extract is reported in this paper.The petroleum ether extract was repeatedly chromatographed over SiO 2 and Sephadex LH-20 using different solvent systems. A new steroid (1) and five known compounds, cholesteryl myristate (2), cholest-4-en-3-one (3), cholesterol (4), 3E,5D,9D-trihydroxy-(22E, 24R)-ergosta-7,22-dien-6-one (5), and 3E,5D,6E-trihydroxy-(22E,24R)-ergosta-7,22-diene (6) were isolated. The structures were identified using spectral methods, including 1D, 2D NMR spectroscopies and mass spectrometry.Compound 1 was isolated as a white crystal. The 1 H and 13 C NMR spectra exhibited the presence of six methyls (four of which were tertiary methyls, one of which was oxygenated), nine methylenes, six methines (one of which was oxygenated), three characterstics quaternary carbons at G C 42.40, 36.53, and 74.88, and four olefinic carbons with corresponding proton signals at G H 5.53 (m), 5.41 (d, J = 16.1 Hz), and 5.35 (t). These data show that 1 possessed a cholesta skeleton having two double bonds, one hydroxyl and one methoxyl. Two double bonds were assigned to be located between C-5 and C-6, as well as C-23 and C-24, by comparison of chemical shifts and coupling constants of three olefinic proton signals with that of a related compound [12,13]. The assignment was further confirmed by HMBC experiment (Fig. 1), in which long-range coupling

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confidence: 55%

Steroids from the marine bryozoan Bugula neritina

et al. 2010

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“…(3β,22E,24ξ)-28,28-Dimethyl-stigmasta-5,22,25-trien-3-ol acetate (116) and (3β,22E)-25-methyl-stigmasta-5,22-dien-3-ol (117) were obtained from an EtOH extract of the sponge Halichondria sp. (152,153), and compound 117 was also found in specimens of the sponge Trachyopsis aplysinoides from Sri Lanka inshore waters (154).…”

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confidence: 88%

“…2,2-Dimethylundecane (151) was extracted with a mixture of n-pentane, methylene chloride and diethyl ether from samples of Cuban sugarcane molasses (176). Two neo alkanes, 2,2dimethyldodecane (152) and 2,2-dimethyl-ridecane (153), were present in alcohol extracts of the fruits of Averrhoa carambola; and 2,2-dimethyltetradecane (158) was isolated from essential oil of Plectranthus coleoides (177,178). The highly branched alkane 2,2,4,6,6-pentamethylheptane (156) was identified in ginseng root oils; it also was found among volatiles from litter and soil associated with Ceratiola ericoides, and in the essential oil of Anthemis montana (Asteraceae) (179)(180)(181).…”

Section: Occurrence Of Neo Alkanes and Derivatives In Naturementioning

confidence: 99%

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Natural neo acids and neo alkanes: Their analogs and derivatives

Dembitsky

2006

Lipids

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This review presents more than 260 naturally occurring (as well as 47 synthesized) neo fatty (carboxylic) acids, neo alkanes, and their analogs and derivatives, isolated and identified from plants, algae, fungi, marine invertebrates, and microorganisms, that demonstrate different biological activities. These natural metabolites are good prospects for future chemical preparations as antioxidants, and also as anticancer, antimicrobial, and antibacterial agents. Described also are some synthetic bioactive compounds containing a tertiary butyl group(s) that have shown high anticancer, antifungal, and other activities. Applications of some neo fatty (carboxylic) acid derivatives in cosmetic, agronomic, and pharmaceutical industries also are considered. This is the first review to consider naturally occurring neo fatty (carboxylic) acids, neo alkanes, and other metabolites containing a tertiary butyl group(s) [or tert-butyl unit(s)].

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“…This same substance has already been identified on the marine sponge Halichondria sp. [23,28] The substance 24α-ethylcholesta-5,22-dien-3β-ol (12) was the only substance evaluated by both mass spectrometry ionization source ESI (positive ion mode) and APCI (negative ion mode), and properly isolated and identified. It was characterized by the quasi-molecular ion at m/z 413 [M + H] + , with the presence of the main fragments at m/z 409, 395, 383, 311 and 255.…”

Section: Chemical Compositionmentioning

confidence: 99%

Chemical Composition and Biological Activities of Metania and Drulia (Metaniidae) Freshwater Sponges from Amazonia

Bolson

Barros

Volkmer‐Ribeiro

et al. 2019

Chemistry & Biodiversity

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Sponges from freshwater environments, unlike marine's, are poorly known producers of natural compounds with medicinal purposes. Amazonian sponges produce massive large specimens and are widely spread, taxonomically diverse and their metabolites could represent a new frontier on unusual natural products to treat diseases such as Alzheimer's and Malaria. Species of Metania and Drulia (Metaniidae) genera are major contributors to the fauna of Amazonian freshwater sponges. Methanolic extracts from several species from these genera had their inhibitory activities evaluated in vitro, for parasite Plasmodium falciparum and acetyl and butyrylcholinesterase enzymes (AChE and BChE). All extracts were able to inhibit AChE, although no activity was observed towards BChE. Drulia uruguayensis extract was the most potent, inhibiting AChE with IC50=1.04 mg/mL. For antiplasmodial activity, all species showed inhibition to P. falciparum, but Metania reticulata being the most efficient with IC50=2.7 μg/mL. Mass spectrometry analyses evidenced the presence of fatty acids and sterols in active extracts.

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Steroid compounds of marine sponges. III. 24-Ethyl-25-methylcholesta-5,22-dien-3β-OL — A new marine sterol from the spongeHalichondria sp.

Cited by 5 publications

References 4 publications

Steroids from the marine bryozoan Bugula neritina

Steroids from the marine bryozoan Bugula neritina

Natural neo acids and neo alkanes: Their analogs and derivatives

Chemical Composition and Biological Activities of Metania and Drulia (Metaniidae) Freshwater Sponges from Amazonia

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