Marine Sterols. Side-Chain-Oxygenated Sterols, Possibly of Abiotic Origin, from the New Caledonian Sponge Stelodoryx chlorophylla

Riccardis, Francesco De; Minale, L.; Iorizzi, Maria; Debitus, Cécile; Lévi, Claude

doi:10.1021/np50092a016

Cited by 45 publications

(46 citation statements)

References 8 publications

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“…Compounds 1, 35,36) 32) were prepared by the reported methods. Compound 9 39) was synthesized by reaction of (C 6 H 5 ) 3 AsCH 2 COCH(CH 3 ) 2 Br 40) with the aldehyde 15 41) (Chart 2) followed by aqueous acid treatment. 42) Compound 11 43) was prepared from the aldehyde 15 by reaction with (C 6 H 5 ) 3 PϭCHCOOCH 3 to afford the a,b-unsaturated ester, followed by aqueous acid treatment.…”

Section: Methodsmentioning

confidence: 99%

Coordination of Sodium Cation to an Oxygen Function and Olefinic Double Bond to Form Molecular Adduct Ion in Fast Atom Bombardment Mass Spectrometry.

Morisaki

Kobayashi

Yamamura

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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One of the most important uses of mass spectrometry in organic chemistry is in the determination of molecular weight (MW: M). In fast atom bombardment (FAB) mass spectrometry, 1-3) molecular-related ion peaks of organic compounds are generally observed as [MϩH] ϩ , [M] ϩ , [MϪH] ϩ or [Mϩ2H] ϩ (for positive ion), depending on the structures. However, compounds which decompose during the analyses show only very weak or no molecular-related ion peaks. In such cases, addition of an alkali metal salt to the compounds sometimes helps to induce adduct ion peaks [MϩA] ϩ (A: atomic weight of alkali metal), and these peaks have also been used for molecular weight determination in FAB mass spectrometry. 4-7)Alkali metal adduct ions of organic compounds are observed in FAB mass analyses of various compounds, especially polyoxygenated compounds such as saccharides [8][9][10][11] and polyethers, [12][13][14][15] and polyfunctional compounds such as peptides. [16][17][18][19] We previously reported the structural requirements of oxygen functional groups for stabilization of the adduct ions in FAB mass spectra of a variety of diols and related compounds with the addition of NaCl. 7) Compounds with two proximal oxygens efficiently coordinated to Na ϩ , and afforded the adduct ion peaks [MϩNa] ϩ [Chart 1a]. However, compounds with an isolated hydroxyl group or ether oxygen hardly formed a complex with Na ϩ , and the intensities of the Na ϩ adduct ion peaks were negligible compared to those of diols, including n-hexadecane-1,2-diol (12), which formed stable Na ϩ adduct ions.7)The affinity of alkali metal cations to p-electrons has been extensively investigated on the basis of cation p-interactions. [20][21][22][23][24][25][26][27][28] Experiments to determine the binding energies of alkali metal cations with benzene and ethylene in the gas phase have been carried out by mass analyses of ion-molecule binding under solvent-free conditions and without counter ion influence. [22][23][24] Theoretical studies have also been carried out to calculate the binding energies of alkali metal cations to aromatic compounds.25-27) As described above, our previous studies showed that compounds with an isolated hydroxyl group hardly formed a complex with Na ϩ under FAB mass spectrometric conditions. 7) However, if an olefinic double bond and Na ϩ could interact, allylic alcohols might form a complex with Na ϩ by the participation of both the hydroxyl group and the olefinic double bond to yield [MϩNa] ϩ ion peaks effectively [Chart 1b]. Allylic alcohols are susceptible to dehydroxylation (protonation followed by dehydration to form the allylic cation) under FAB mass spectrometric conditions, but if the hydroxyl group and olefinic double bond were coordinated to Na ϩ , the complex might not readily undergo dehydroxylation, as in the case of 1,2-diols. 7)This paper reports the interactions of Na ϩ with allylic alcohols in FAB mass spectrometry. Steroidal allylic alcohols, in which a,b-unsaturated hydroxyl groups were located in ring A ...

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Section: Methodsmentioning

confidence: 99%

Coordination of Sodium Cation to an Oxygen Function and Olefinic Double Bond to Form Molecular Adduct Ion in Fast Atom Bombardment Mass Spectrometry.

Morisaki

Kobayashi

Yamamura

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Thirteen sterols were isolated from the cheilostome Cryptosula pallasiana (Cryptosulidae) collected off Huang Island (Qingdao, China) [92]. Three of these sterols were also isolated from the sponge Cliona viridis (copiosa) (Schmidt, 1862) (Clionaidae), collected in the Bay of Naples (Italy) at a depth of 15 m [93] and the deep-water sponge Stelodoryx chlorophylla Lévi, 1993 (Myxillidae), collected south of New Caledonia at a depth of 600-540 m [94]. Among the sterols, seven of them ((23E)-25methoxycholesta-5,23-dien-3β-ol, (22E)-7β-methoxy-cholesta-5,22-dien-3β-ol, 7β-methoxy-cholest-5en-3β-ol, (23E)-3β-hydroxy-27-norcholesta-5,23-dien-25-one, (23Z)-cholesta-5,23-diene-3β,25-diol, (22E)-3β-hydroxycholesta-5,22-dien-7-one and (22E)-3β-hydroxy-24-norcholesta-5,22-dien-7-one) exhibited moderate cytotoxic effects against human myeloid leukaemia HL-60 cells.…”

Section: Sterolsmentioning

confidence: 99%

The Understudied Phylum Bryozoa as a Promising Source of Anticancer Drugs

Figuerola¹,

Ávila²

2019

Preprint

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Recent advances in sampling and novel techniques in drug synthesis and isolation have promoted the discovery of anticancer agents from marine organisms to combat this major threat to public health worldwide. Bryozoans, filter-feeding, sessile aquatic invertebrates often characterized by a calcified skeleton, are an excellent source of pharmacologically interesting compounds including well-known chemical classes such as alkaloids and polyketides. This review covers the literature for secondary metabolites isolated from marine cheilostome and ctenostome bryozoans that have shown potential as cancer drugs. Moreover, we highlight examples such as bryostatins, the most known class of marine-derived compounds from this animal phylum, which is advancing through anticancer clinical trials due to their low toxicity and antineoplastic activity. The bryozoan antitumour compounds discovered until now show a wide range of chemical diversity and biological activities. Therefore, more research focusing on the isolation of secondary metabolites with potential anticancer properties from bryozoans and other overlooked taxa covering wider geographic areas is needed for an efficient bioprospecting of natural products.

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“…Twenty-two steroid components present in the deepwater sponge Stelodoryx chlorophylla, from New Caledonia, have been identified; among them, seven products (114 -120) were new compounds [71]. With the exception of 119 and 120, they are steroids with oxygenated or short oxygenated side-chains.…”

Section: Steroids With Unconventional Side-chainmentioning

confidence: 99%