5α,8α-Epidioxysterols from the gorgonian Eunicella cavolini and the ascidian Trididemnum inarmatum: Isolation and evaluation of their antiproliferative activity

Iοannou, Efstathia; Abdel-Razik, Ayman F.; Zervou, Maria; Christofidis, Dimitrios; Alexi, Xanthippi; Vagias, Constantinos; Alexis, Μichael N.; Roussis, Vassilios

doi:10.1016/j.steroids.2008.09.007

Cited by 78 publications

(70 citation statements)

References 26 publications

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“…381 Eunicella cavolini (Lichadonissia Is., Greece) provided another group of 5α,8α-epidioxysterols 610-612. 382 Three epoxysteroids 613, 614 383 and 615 384 were obtained from Helianthus tuberosus and Lentinus edodes, respectively. An undescribed endophytic Phomopsis species from Maytenus hookeri provided a new sterol 616.…”

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confidence: 99%

Peroxy natural products

Liu

2013

Nat. Prod. Bioprospect.

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confidence: 99%

Peroxy natural products

Liu

2013

Nat. Prod. Bioprospect.

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“…Compounds 5 and 6 were obtained from the gorgonian D. gemmacea and identified as 5a,8a-epidioxy-ergosta-6,22-dien-3b-ol and 3b-hydroxycholest-5-en-25-acetoxy-19-oate, respectively. Compound 5 was determined by comparing the 1 H and 13 C NMR data with those reported in the literature (Ioannou et al, 2009). Compound 6 was found for the first time by Wang's group (Changyun Wang, Ocean University of China) in the same gorgonian and was reported only in the master's degree dissertation of Liu (2008).…”

Section: Resultsmentioning

confidence: 99%

“…5a,8a-Epidioxysterols, which are proposed to be formed by the photooxidation reaction of conjugated D 5,7 -sterols (Aknin et al, 2010), reportedly inhibit the growth of many human and murine cancer cell lines (Ioannou et al, 2009). The IC 50 values (4.9-6.8 mg/mL) of the inhibitory activities against HMGCR-GFP showed that 5a,8a-epidioxysterols 3-5 may be effective for cholesterol metabolism disorder.…”

Section: Resultsmentioning

confidence: 99%

Bioactivities of six sterols isolated from marine invertebrates

Zhou

Sun

et al. 2013

Pharmaceutical Biology

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Context: Epidioxy sterols and sterols with special side chains, such as hydroperoxyl sterols, usually obtained from marine natural products, are attractive for bioactivities. Objective: To isolate and screen bioactive and special sterols from China Sea invertebrates. Materials and methods: Two hydroperoxyl sterols (1 and 2) from the sponge Xestospongia testudinaria Lamarck (Petrosiidae), three epidioxy sterols (3-5) from the sea urchin Glyptocidaris crenularis A. Agassiz (Glyptocidaridae), sponge Mycale sp. (Mycalidae) and gorgonian Dichotella gemmacea Milne Edwards and Haime (Ellisellidae) and an unusual sterol with 25-acetoxy-19-oate (6) also from D. gemmacea were obtained and identified. Using high-throughput screening, their bioactivities were tested toward Forkhead box O 3a (Foxo3a), 3-hydroxy-3-methylglutaryl CoA reductase gene fluorescent protein (HMGCR-GFP), nuclear factor kappa B (NF-kB) luciferase, peroxisome proliferator-activated receptor-g co-activator 1a (PGC-1a), protein-tyrosine phosphatase 1B (PTP1B), mitochondrial membrane permeabilization (MMP) and adenosine monophosphate-activated protein kinase. Results: Their structures were determined by comparing their nuclear magnetic resonance data with those reported in the literature. Three epidioxy sterols (3-5) showed inhibitory activities toward Foxo3a, HMGCR-GFP and NF-kB-luciferase with the IC 50 values 4.9-6.8 mg/mL. The hydroperoxyl sterol 29-hydroperoxystigmasta-5,24(28)-dien-3-ol (2) had diverse inhibitory activities against Foxo3a, HMGCR-GFP, NF-kB-luciferase, PGC-1a, PTP1B and MMP, with IC 50 values of 3.8-19.1 mg/mL. Discussion and conclusion: The bioactivities of 3-5 showed that 5a,8a-epidioxy is the active group. Otherwise, the most plausible biosynthesis pathway for 1 and 2 in sponge involves the abstraction of an allylic proton by an activated oxygen, such as O 2 , along with migration of carbon-carbon double bond. Therefore, the bioactive and unstable steroid should be biosynthesized in sponge under a special ecological environment to act as a defensive strategy against invaders.

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“…24 Thus, the structure of 2 was established as 6β-carboxyl-24(R)-(8→6) abeo-ergostan-3β,5β-diol. In addition to the new compounds 1 and 2, seven known sterols have also been isolated: 7α-hydroxycampesterol (3), 19 5α,8α-epi-dioxycampesterol (4), 25 campesterol (5), 26 24(R)-ergost-7-en-3β,5α,6β-triol (6), 27 20-hydroxyecdysone (7), (Table S2 and Figure S20).Orostanal, an abeo-sterol isolated from a marine sponge, and its derivatives, are known to have moderated cytotoxic effects. 28 The scanty literature attributes the cytotoxic activity of these class of compounds to apoptosis induction.…”

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Steroids from the Brazilian Zoanthids Palythoa caribaeorum and Palythoa variabilis

Pinto¹,

Almeida²,

Silveira³

et al. 2016

J. Braz. Chem. Soc.

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Two unreported ergostane-type sterols 24(R)-7α-hydroperoxy-ergost-5-en-3β-ol and 6β-carboxyl-24(R)-(8→6)-abeo-ergostan-3β,5β-diol, along with seven known ones were isolated from the hexane and alcohol extracts from the zoanthids Palythoa caribaeorum and Palythoa variabilis. The structures of the new compounds were determined using spectroscopic techniques, including 1D and 2D nuclear magnetic resonance (NMR), high-resolution electrospray ionization mass spectrometry (HRESIMS), and comparison with data previously published. 6β-Carboxyl-24(R)-(8→6)-abeo-ergostan-3β,5β-diol showed moderate cytotoxicity against colon cancer cells (HCT-116) as previously described for others abeo-sterol derivatives. Keywords: Palythoa caribaeorum, Palythoa variabilis, ergostane sterols, cytotoxic activity IntroductionZoanthids are cnidarians found in most marine environments, from temperate to tropical areas and from the intertidal zone to the deep sea below 5000 m, but are particularly common in tropical and subtropical seas. The colonial zoanthid genus Palythoa (order Zoantharia) is represented by ca. 92 species.2 It has been the subject of constant taxonomy investigations due to an incomplete understanding of their diversity. lipidic α-amino acids, 13 and pyrazines. 14 Lipids and steroids represent the commonest classes of compounds isolated from Palythoa spp. (Figure 1). The most potent toxic nonprotein known, palytoxin, has been isolated from Palythoa species. 15 The first natural lipid α-amino acids (C 30 and C 31 ) have been isolated from Protopalythoa variabilis, and exhibited cytotoxic effects against human cancer cell lines.13 Protopalythoa taxonomy previously assigned 4,13 is under revision based on mitochondrial DNA analysis, indicating that Protopalythoa and Palythoa are indeed congeneric designations. 16The present investigation reports on the steroidal composition of P. caribaeorum and P. variabilis. Both species are abundant in shallow waters along the Brazilian Northeast coastline. ExperimentalGeneral Infrared (IR) spectra were obtained on a PerkinElmer FT-IR spectrum 1000 spectrometer. Optical rotations were measured on a PerkinElmer 341 digital polarimeter at 25 °C.Steroids from the Brazilian Zoanthids Palythoa caribaeorum and Palythoa variabilis J. Braz. Chem. Soc. 486 Melting points, not corrected, were determined on a digital MQAPF-302 melting point apparatus (Microquimica), with a heating rate of 2 °C min -1 . 1 H (500 or 300 MHz) and 13 C (125 or 75 MHz) nuclear magnetic resonance (NMR) spectra were performed either on a Bruker Avance DRX-500 or Avance DPX-300 spectrometer. High resolution electrospray ionization mass spectrometry (HRESIMS) was acquired using a liquid chromatography-mass spectrometry ion trap and time-of-flight (LCMS-IT-TOF, Shimadzu) spectrometer, consisting of an UFLC (ultra fast liquid chromatography) system coupled to an IT-TOF mass spectrometer equipped with electrospray ionization (ESI) source operating either in positive or negative mode. The mass spectra were recorded in the range ...

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5α,8α-Epidioxysterols from the gorgonian Eunicella cavolini and the ascidian Trididemnum inarmatum: Isolation and evaluation of their antiproliferative activity

Cited by 78 publications

References 26 publications

Peroxy natural products

Peroxy natural products

Bioactivities of six sterols isolated from marine invertebrates

Steroids from the Brazilian Zoanthids Palythoa caribaeorum and Palythoa variabilis

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