Steroids and alkaloids from the South China Sea sponge<i>Axinella</i>sp.

Marine indole alkaloids comprise a large and steadily growing group of secondary metabolites. Their diverse biological activities make many compounds of this class attractive starting points for pharmaceutical development. Several marine-derived indoles were found to possess cytotoxic, antineoplastic, antibacterial and antimicrobial activities, in addition to the action on human enzymes and receptors. The newly isolated indole alkaloids of marine origin since the last comprehensive review in 2003 are reported, and biological aspects will be discussed.

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“…1-(1 H -Indol-3-yl)-2,3-dihydroxy-5-methyl-hexane ( 75 ) was isolated from the South China Sea sponge Axinella sp. ( Figure 16 ) [ 64 ].…”

Section: Marine Indole Alkaloidsmentioning

confidence: 99%

Marine Indole Alkaloids

2015

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“…[21], Axinella sp. [22]. However, to our knowledge, it is the first time that such kind of steroid was found from marine sponge X. testudinaria.…”

Section: Resultsmentioning

confidence: 82%

“…The bioassay result indicated that compound 1 exhibit significant PTP1B inhibitory activity with an IC 50 value of 4.27^0.55 mM, when compared to the positive control oleanolic acid (IC 50 ¼ 2.63^0.22 mM). In addition, cytotoxic activities of 1 against the growth of human promyelocytic leukemia cells (HL60) and human lung adenocarcinoma cells (A549) have also been tested since literature survey revealed that many oxygenated steroids showed promising cytotoxicity against various tumor cell lines [18][19][20][21][22][23]. Unfortunately, the results indicated that 1 was inactive against the above cancer cell lines (50% effective dose of clonal inhibition ED 50 .…”

Section: Resultsmentioning

confidence: 99%

A new bioactive steroidal ketone from the South China Sea sponge Xestospongia testudinaria

Xue

Yao

et al. 2015

Journal of Asian Natural Products Research

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A new steroidal ketone (1), with an ergosta-22,25-diene side chain, was obtained from the South China Sea marine sponge Xestospongia testudinaria. The structure of 1 was determined on the basis of detailed spectroscopic analysis and by comparison with literature. Compound 1 exhibited significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a key target for the treatment of type II diabetes and obesity, with an IC50 value of 4.27 ± 0.55 μM, which is comparable with the positive control oleanolic acid (IC50 = 2.63 ± 0.22 μM).

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“…Since the first report of steroids from marine sponges by Bergman in 1949 [ 34 ], numerous reports have described conventional and unconventional steroids from demosponges with modifications on the tetracyclic nucleus or the side chain, including e.g., aminosteroids, sulfated polyhydroxysterols, side-chain-oxygenated sterols and sulfated steroid-amino acid conjugates [ 20 , 33 , 35 , 36 , 37 ]. Axinella sponges are known to have generally complex steroid profiles including steroids and nor-steroids [ 36 , 38 , 39 ]. The previous GC-MS study on A. sinoxea led to the identification of eight steroidal compounds: cholesta-5,22-dien-3β-ol, cholest-5-en-3β-ol, ergosta-5,22-dien-3β-ol, ergost-5-en-3β-ol, stigmasta-5,22-dien-3β-ol, γ-sitosterol, 33-norgorgosta-5,24(28)-dien-3β-ol and stigmasta-5,24(28)-dien-3β-ol [ 12 ].…”

Section: Discussionmentioning

confidence: 99%

Integrating Molecular Networking and 1H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge Axinella sinoxea

Kouchaksaraee

Farimani

et al. 2020

Marine Drugs

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The geographic position, highly fluctuating sea temperatures and hypersalinity make Persian Gulf an extreme environment. Although this unique environment has high biodiversity dominated by invertebrates, its potential in marine biodiscovery has largely remained untapped. Herein, we aimed at a detailed analysis of the metabolome and bioactivity profiles of the marine sponge Axinella sinoxea collected from the northeast coast of the Persian Gulf in Iran. The crude extract and its Kupchan subextracts were tested in multiple in-house bioassays, and the crude extract and its CHCl3-soluble portion showed in vitro antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) and Enterococcus faecium (Efm). A molecular networking (MN)-based dereplication strategy by UPLC-MS/MS revealed the presence of phospholipids and steroids, while 1H NMR spectroscopy indicated the presence of additional metabolites, such as diketopiperazines (DKPs). Integrated MN and 1H NMR analyses on both the crude and CHCl3 extracts combined with an antibacterial activity-guided isolation approach afforded eight metabolites: a new diketopiperazine, (-)-cyclo(L-trans-Hyp-L-Ile) (8); a known diketopiperazine, cyclo(L-trans-Hyp-L-Phe) (7); two known phospholipids, 1-O-hexadecyl-sn-glycero-3-phosphocholine (1) and 1-O-octadecanoyl-sn-glycero-3-phosphocholine (2); two known steroids, 3β-hydroxycholest-5-ene-7,24-dione (3) and (22E)-3β-hydroxycholesta-5,22-diene-7,24-dione (4); two known monoterpenes, loliolide (5) and 5-epi-loliolide (6). The chemical structures of the isolates were elucidated by a combination of NMR spectroscopy, HRMS and [α]D analyses. All compounds were tested against MRSA and Efm, and compound 3 showed moderate antibacterial activity against MRSA (IC50 value 70 μg/mL). This is the first study that has dealt with chemical and bioactivity profiling of A. sinoxea leading to isolation and characterization of pure sponge metabolites.

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Steroids and alkaloids from the South China Sea spongeAxinellasp.

Cited by 11 publications

References 9 publications

Marine Indole Alkaloids

Marine Indole Alkaloids

A new bioactive steroidal ketone from the South China Sea sponge Xestospongia testudinaria

Integrating Molecular Networking and 1H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge Axinella sinoxea

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