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Article ; Online: Oxysterols are potential physiological regulators of ageing.

de Medina, Philippe / Silvente-Poirot, Sandrine / Poirot, Marc

2022 Volume 77, Page(s) 101615

Abstract: Delaying and even reversing ageing is a major public health challenge with a tremendous potential to postpone a plethora of diseases including cancer, metabolic syndromes and neurodegenerative disorders. A better understanding of ageing as well as the ... ...

Abstract	Delaying and even reversing ageing is a major public health challenge with a tremendous potential to postpone a plethora of diseases including cancer, metabolic syndromes and neurodegenerative disorders. A better understanding of ageing as well as the development of innovative anti-ageing strategies are therefore an increasingly important field of research. Several biological processes including inflammation, proteostasis, epigenetic, oxidative stress, stem cell exhaustion, senescence and stress adaptive response have been reported for their key role in ageing. In this review, we describe the relationships that have been established between cholesterol homeostasis, in particular at the level of oxysterols, and ageing. Initially considered as harmful pro-inflammatory and cytotoxic metabolites, oxysterols are currently emerging as an expanding family of fine regulators of various biological processes involved in ageing. Indeed, depending of their chemical structure and their concentration, oxysterols exhibit deleterious or beneficial effects on inflammation, oxidative stress and cell survival. In addition, stem cell differentiation, epigenetics, cellular senescence and proteostasis are also modulated by oxysterols. Altogether, these data support the fact that ageing is influenced by an oxysterol profile. Further studies are thus required to explore more deeply the impact of the "oxysterome" on ageing and therefore this cholesterol metabolic pathway constitutes a promising target for future anti-ageing interventions.
MeSH term(s)	Aging/metabolism ; Cholesterol ; Humans ; Inflammation ; Oxidative Stress ; Oxysterols/metabolism
Chemical Substances	Oxysterols ; Cholesterol (97C5T2UQ7J)
Language	English
Publishing date	2022-03-26
Publishing country	England
Document type	Journal Article ; Review ; Research Support, Non-U.S. Gov't
ZDB-ID	2075672-0
ISSN	1872-9649 ; 1568-1637
ISSN (online)	1872-9649
ISSN	1568-1637
DOI	10.1016/j.arr.2022.101615
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Zs.A 5579: Show issues

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Article ; Online: Oxysterols: An expanding family of structurally diversified bioactive steroids.

Poirot, Marc / Silvente-Poirot, Sandrine

The Journal of steroid biochemistry and molecular biology

2019 Volume 194, Page(s) 105443

MeSH term(s)	Molecular Structure ; Oxysterols/chemistry ; Oxysterols/metabolism
Chemical Substances	Oxysterols
Language	English
Publishing date	2019-07-31
Publishing country	England
Document type	Editorial
ZDB-ID	1049188-0
ISSN	1879-1220 ; 0960-0760
ISSN (online)	1879-1220
ISSN	0960-0760
DOI	10.1016/j.jsbmb.2019.105443
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Article ; Online: The tumor-suppressor cholesterol metabolite, dendrogenin A, is a new class of LXR modulator activating lethal autophagy in cancers.

Poirot, Marc / Silvente-Poirot, Sandrine

Biochemical pharmacology

2018 Volume 153, Page(s) 75–81

Abstract: Dendrogenin A (DDA) is a mammalian cholesterol metabolite recently identified that displays tumor suppressor properties. The discovery of DDA has revealed the existence in mammals of a new metabolic branch in the cholesterol pathway centered on 5,6α- ... ...

Abstract	Dendrogenin A (DDA) is a mammalian cholesterol metabolite recently identified that displays tumor suppressor properties. The discovery of DDA has revealed the existence in mammals of a new metabolic branch in the cholesterol pathway centered on 5,6α-epoxycholesterol and bridging cholesterol metabolism with histamine metabolism. Metabolic studies showed a drop in DDA levels in cancer cells and tumors compared to normal cells, suggesting a link between DDA metabolism deregulation and oncogenesis. Importantly, complementation of cancer cells with DDA induced 1) cancer cell re-differentiation, 2) blockade of 6-oxo-cholestan-3β,5α-diol (OCDO) production, an endogenous tumor promoter and 3) lethal autophagy in tumors. Importantly, by binding the liver X receptor (LXR), DDA activates the expression of genes controlling autophagy. These genes include NR4A1, NR4A3, LC3 and TFEB. The canonical LXR ligands 22(R)hydroxycholesterol, TO901317 and GW3965 did not induce these effects indicating that DDA delineates a new class of selective LXR modulator (SLiM). The induction of lethal autophagy by DDA was associated with the accumulation in cancer cells of lysosomes and of the pro-lysosomal cholesterol precursor zymostenol due to the inhibition of the 3β-hydroxysteroid-Δ
MeSH term(s)	Animals ; Antineoplastic Agents/metabolism ; Antineoplastic Agents/pharmacology ; Antineoplastic Agents/therapeutic use ; Autophagy/drug effects ; Autophagy/physiology ; Cell Line, Tumor ; Cholestanols/metabolism ; Cholestanols/pharmacology ; Cholestanols/therapeutic use ; Cholesterol/metabolism ; Cholesterol/pharmacology ; Cholesterol/therapeutic use ; Humans ; Imidazoles/metabolism ; Imidazoles/pharmacology ; Imidazoles/therapeutic use ; Liver X Receptors/metabolism ; Neoplasms/drug therapy ; Neoplasms/metabolism
Chemical Substances	5-hydroxy-6-(2-(1H-imidazol-4-yl)ethylamino)cholestan-3-ol ; Antineoplastic Agents ; Cholestanols ; Imidazoles ; Liver X Receptors ; Cholesterol (97C5T2UQ7J)
Language	English
Publishing date	2018-02-01
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Review
ZDB-ID	208787-x
ISSN	1873-2968 ; 0006-2952
ISSN (online)	1873-2968
ISSN	0006-2952
DOI	10.1016/j.bcp.2018.01.046
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Zs.A 19: Show issues

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Article ; Online: Targeting NR1H/liver X receptor with dendrogenin A differentiates tumor cells to activate a new secretory pathway releasing immunogenic anti-tumor vesicles enriched in LC3-II-associated exosomes.

de Medina, Philippe / Bunay, Julio / Poirot, Marc / Record, Michel / Silvente-Poirot, Sandrine

Autophagy

2022 Volume 19, Issue 3, Page(s) 1036–1038

Abstract: Normal cells secrete small extracellular vesicles (sEV), containing exosomes and/or ectosomes, which play a beneficial role in monitoring tissue integrity and immune response, whereas cancer cells constitutively secrete sEV, which contribute to inhibit ... ...

Abstract	Normal cells secrete small extracellular vesicles (sEV), containing exosomes and/or ectosomes, which play a beneficial role in monitoring tissue integrity and immune response, whereas cancer cells constitutively secrete sEV, which contribute to inhibit the immune defenses and promote tumor progression and aggressiveness. Therefore, there is a great interest in reprograming tumor sEV functions toward normal ones. We hypothesized that this could be realized by inducing tumor cell re-differentiation with dendrogenin A (DDA), an endogenous oxysterol and a ligand of NR1 H/LXR (nuclear receptor subfamily 1 group H). At low doses, DDA induces tumor cell differentiation, tumor growth inhibition and immune cell infiltration into tumors. At high doses, DDA induces lethal macroautophagy/autophagy in tumors by increasing LC3 expression at the mRNA and protein level, through NR1H2/LXRβ. In the present study, we showed that low doses of DDA re-differentiate tumor cells by interacting with NR1H2. This results in an increased formation of multivesicular bodies (MVB) in tumor cells and an enhanced secretion of LC3-II-associated exosome-enriched sEV, with immune and anticancer properties. This study highlights the original LC3-II-associated exosome secretory pathway driven by the DDA-NR1H2 complex and paves the way to the development of new therapeutic strategies against pro-tumor exosomes.
MeSH term(s)	Humans ; Liver X Receptors/metabolism ; Exosomes/metabolism ; Secretory Pathway ; Autophagy ; Neoplasms/metabolism
Chemical Substances	5-hydroxy-6-(2-(1H-imidazol-4-yl)ethylamino)cholestan-3-ol ; Liver X Receptors
Language	English
Publishing date	2022-09-05
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2454135-7
ISSN	1554-8635 ; 1554-8627
ISSN (online)	1554-8635
ISSN	1554-8627
DOI	10.1080/15548627.2022.2116175
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Zs.A 6741: Show issues

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Article ; Online: Chemical synthesis and biochemical properties of cholestane-5α,6β-diol-3-sulfonate: A non-hydrolysable analogue of cholestane-5α,6β-diol-3β-sulfate.

de Médina, Philippe / Ayadi, Silia / Soulès, Régis / Payre, Bruno / Rup-Jacques, Sandrine / Silvente-Poirot, Sandrine / Samadi, Mohammad / Poirot, Marc

The Journal of steroid biochemistry and molecular biology

2023 Volume 234, Page(s) 106396

Abstract: Cholestane-3β,5α,6β-triol (CT) is a primary metabolite of 5,6-epoxycholesterols (5,6-EC) that is catalyzed by the cholesterol-5,6-epoxide hydrolase (ChEH). CT is a well-known biomarker for Niemann-Pick disease type C (NP-C), a progressive inherited ... ...

Abstract	Cholestane-3β,5α,6β-triol (CT) is a primary metabolite of 5,6-epoxycholesterols (5,6-EC) that is catalyzed by the cholesterol-5,6-epoxide hydrolase (ChEH). CT is a well-known biomarker for Niemann-Pick disease type C (NP-C), a progressive inherited neurodegenerative disease. On the other hand, CT is known to be metabolized by the 11β-hydroxysteroid-dehydrogenase of type 2 (11β-HSD2) into a tumor promoter named oncosterone that stimulates the growth of breast cancer tumors. Sulfation is a major metabolic transformation leading to the production of sulfated oxysterols. The production of cholestane-5α,6β-diol-3β-O-sulfate (CDS) has been reported in breast cancer cells. However, no data related to CDS biological properties have been reported so far. These studies have been hampered because sulfate esters of sterols and steroids are rapidly hydrolyzed by steroid sulfatase to give free steroids and sterols. In order to get insight into the biological properties of CDS, we report herein the synthesis and the characterization of cholestane-5α,6β-diol-3β-sulfonate (CDSN), a non-hydrolysable analogue of CDS. We show that CDSN is a potent inhibitor of 11β-HSD2 that blocks oncosterone production on cell lysate. The inhibition of oncosterone biosynthesis of a whole cell assay was observed but results from the blockage by CDSN of the uptake of CT in MCF-7 cells. While CDSN inhibits MCF-7 cell proliferation, we found that it potentiates the cytotoxic activity of post-lanosterol cholesterol biosynthesis inhibitors such as tamoxifen and PBPE. This effect was associated with an increase of free sterols accumulation and the appearance of giant multilamellar bodies, a structural feature reminiscent of Type C Niemann-Pick disease cells and consistent with a possible inhibition by CDSN of NPC1. Altogether, our data showed that CDSN is biologically active and that it is a valuable tool to study the biological properties of CDS and more specifically its impact on immunity and viral infection.
MeSH term(s)	Humans ; Female ; Sulfates ; 11-beta-Hydroxysteroid Dehydrogenase Type 2 ; Neurodegenerative Diseases ; Cholesterol/metabolism ; Sterols ; Breast Neoplasms
Chemical Substances	Sulfates ; 11-beta-Hydroxysteroid Dehydrogenase Type 2 (EC 1.1.1.146) ; Cholesterol (97C5T2UQ7J) ; Sterols
Language	English
Publishing date	2023-09-06
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1049188-0
ISSN	1879-1220 ; 0960-0760
ISSN (online)	1879-1220
ISSN	0960-0760
DOI	10.1016/j.jsbmb.2023.106396
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Article ; Online: Is cholesterol a risk factor for breast cancer incidence and outcome?

Ben Hassen, Céline / Goupille, Caroline / Vigor, Claire / Durand, Thierry / Guéraud, Françoise / Silvente-Poirot, Sandrine / Poirot, Marc / Frank, Philippe G

The Journal of steroid biochemistry and molecular biology

2023 Volume 232, Page(s) 106346

Abstract: Cholesterol plays important roles in many physiological processes, including cell membrane structure and function, hormone synthesis, and the regulation of cellular homeostasis. The role of cholesterol in breast cancer is complex, and some studies have ... ...

Abstract	Cholesterol plays important roles in many physiological processes, including cell membrane structure and function, hormone synthesis, and the regulation of cellular homeostasis. The role of cholesterol in breast cancer is complex, and some studies have suggested that elevated cholesterol levels may be associated with an increased risk of developing breast cancer, while others have found no significant association. On the other hand, other studies have shown that, for total cholesterol and plasma HDL-associated cholesterol levels, there was inverse association with breast cancer risk. One possible mechanism by which cholesterol may contribute to breast cancer risk is as a key precursor of estrogen. Other potential mechanisms by which cholesterol may contribute to breast cancer risk include its role in inflammation and oxidative stress, which have been linked to cancer progression. Cholesterol has also been shown to play a role in signaling pathways regulating the growth and proliferation of cancer cells. In addition, recent studies have shown that cholesterol metabolism can generate tumor promoters such as cholesteryl esters, oncosterone, 27-hydroxycholesterol but also tumor suppressor metabolites such as dendrogenin A. This review summarizes some of the most important clinical studies that have evaluated the role of cholesterol or its derivatives in breast cancer. It also addresses the role of cholesterol and its derivatives at the cellular level.
MeSH term(s)	Humans ; Female ; Breast Neoplasms/metabolism ; Incidence ; Cholesterol/metabolism ; Cholesterol Esters/metabolism ; Risk Factors
Chemical Substances	Cholesterol (97C5T2UQ7J) ; Cholesterol Esters
Language	English
Publishing date	2023-06-13
Publishing country	England
Document type	Review ; Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1049188-0
ISSN	1879-1220 ; 0960-0760
ISSN (online)	1879-1220
ISSN	0960-0760
DOI	10.1016/j.jsbmb.2023.106346
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Article ; Online: 27-Hydroxylation of oncosterone by CYP27A1 switches its activity from pro-tumor to anti-tumor.

Ayadi, Silia / Friedrichs, Silvia / Soulès, Regis / Pucheu, Laly / Lütjohann, Dieter / Silvente-Poirot, Sandrine / Poirot, Marc / de Medina, Philippe

Journal of lipid research

2023 Volume 64, Issue 12, Page(s) 100479

Abstract: Oncosterone (6-oxo-cholestane-3β,5α-diol; OCDO) is an oncometabolite and a tumor promoter on estrogen receptor alpha-positive breast cancer (ER(+) BC) and triple-negative breast cancers (TN BC). OCDO is an oxysterol formed in three steps from cholesterol: ...

Abstract	Oncosterone (6-oxo-cholestane-3β,5α-diol; OCDO) is an oncometabolite and a tumor promoter on estrogen receptor alpha-positive breast cancer (ER(+) BC) and triple-negative breast cancers (TN BC). OCDO is an oxysterol formed in three steps from cholesterol: 1) oxygen addition at the double bond to give α- or β- isomers of 5,6-epoxycholestanols (5,6-EC), 2) hydrolyses of the epoxide ring of 5,6-ECs to give cholestane-3β,5α,6β-triol (CT), and 3) oxidation of the C6 hydroxyl of CT to give OCDO. On the other hand, cholesterol can be hydroxylated by CYP27A1 at the ultimate methyl carbon of its side chain to give 27-hydroxycholesterol ((25R)-Cholest-5-ene-3beta,26-diol, 27HC), which is a tumor promoter for ER(+) BC. It is currently unknown whether OCDO and its precursors can be hydroxylated at position C27 by CYP27A1, as is the impact of such modification on the proliferation of ER(+) and TN BC cells. We investigated, herein, whether 27H-5,6-ECs ((25R)-5,6-epoxycholestan-3β,26-diol), 27H-CT ((25R)-cholestane-3β,5α,6β,26-tetrol) and 27H-OCDO ((25R)-cholestane-6-oxo-3β,5α,26-triol) exist as metabolites and can be produced by cells expressing CYP27A1. We report, for the first time, that these compounds exist as metabolites in humans. We give pharmacological and genetic evidence that CYP27A1 is responsible for their production. Importantly, we found that 27-hydroxy-OCDO (27H-OCDO) inhibits BC cell proliferation and blocks OCDO and 27-HC-induced proliferation in BC cells, showing that this metabolic conversion commutes the proliferative properties of OCDO into antiproliferative ones. These data suggest an unprecedented role of CYP27A1 in the control of breast carcinogenesis by inhibiting the tumor promoter activities of oncosterone and 27-HC.
MeSH term(s)	Humans ; Female ; Hydroxylation ; Cholesterol/metabolism ; Breast Neoplasms/drug therapy ; Breast Neoplasms/metabolism ; Oxysterols ; Cytochrome P-450 Enzyme System/metabolism ; Carcinogens/metabolism ; Cholestanetriol 26-Monooxygenase
Chemical Substances	Cholesterol (97C5T2UQ7J) ; Oxysterols ; Cytochrome P-450 Enzyme System (9035-51-2) ; Carcinogens ; CYP27A1 protein, human (EC 1.14.15.15) ; Cholestanetriol 26-Monooxygenase (EC 1.14.15.15)
Language	English
Publishing date	2023-11-20
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	80154-9
ISSN	1539-7262 ; 0022-2275
ISSN (online)	1539-7262
ISSN	0022-2275
DOI	10.1016/j.jlr.2023.100479
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Article ; Online: In vitro and In vivo oxidation and cleavage products of tocols: From chemical tuners to “VitaminEome” therapeutics. A narrative review

Khallouki, Farid / Saber, Somayya / Bouddine, Toufik / Hajji, Lhoussain / Elbouhali, Bachir / Silvente-Poirot, Sandrine / Poirot, Marc

Food Bioscience. 2022 Oct., v. 49 p.101839-

2022

Abstract: Vitamin E components and vitamin E oxidation products (VEOP) define the “vitaminEome”. VEOP are produced through biological and chemical processes. They are found at low concentrations in vivo and may play particular biological functions linked with ... ...

Abstract	Vitamin E components and vitamin E oxidation products (VEOP) define the “vitaminEome”. VEOP are produced through biological and chemical processes. They are found at low concentrations in vivo and may play particular biological functions linked with chemoprevention and inflammatory processes. Much data have been reported leading to more insight into VEOP. VEOP are generated through peroxy-radical generating systems and via reactive oxygen and nitrogen species as well as enzymatically by a variety of enzymes. In vivo, VEOP and their catabolites may reach the blood circulation and display physiological properties. This narrative review expands upon parent vitamin E chemistry as well as VEOP chemical concepts. The in vitro and in vivo routes by which they can be generated are exhaustively approached. Finally, we will discuss therapeutic and chemopreventive opportunities that VEOP offer with a special focus on their cytotoxic and anti-inflammatory functions.
Keywords	blood circulation ; chemoprevention ; cytotoxicity ; metabolites ; nitrogen ; oxidation ; oxygen ; therapeutics ; vitamin E ; Vitamin E oxidation products ; Chemistry ; Tocopherylquinones ; 5-Nitro-γ- tocopherol ; Vitamin E long chain metabolites ; Anti-inflammatory activities
Language	English
Dates of publication	2022-10
Publishing place	Elsevier Ltd
Document type	Article ; Online
ISSN	2212-4292
DOI	10.1016/j.fbio.2022.101839
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Article ; Online: When cholesterol meets histamine, it gives rise to dendrogenin A: a tumour suppressor metabolite.

Poirot, Marc / Silvente-Poirot, Sandrine

Biochemical Society transactions

2016 Volume 44, Issue 2, Page(s) 631–637

Abstract: Dendrogenin A (DDA) is the first steroidal alkaloid (SA) to be identified in human tissues to date and arises from the stereoselective enzymatic conjugation of 5,6α-epoxycholesterol (5,6α-EC) with histamine (HA). DDA induces the re-differentiation of ... ...

Abstract	Dendrogenin A (DDA) is the first steroidal alkaloid (SA) to be identified in human tissues to date and arises from the stereoselective enzymatic conjugation of 5,6α-epoxycholesterol (5,6α-EC) with histamine (HA). DDA induces the re-differentiation of cancer cellsin vitroandin vivoand prevents breast cancer (BC) and melanoma development in mice, evidencing its protective role against oncogenesis. In addition, DDA production is lower in BCs compared with normal tissues, suggesting a deregulation of its biosynthesis during carcinogenesis. The discovery of DDA reveals the existence of a new metabolic pathway in mammals which lies at the crossroads of cholesterol and HA metabolism and which leads to the production of this metabolic tumour suppressor.
MeSH term(s)	Animals ; Anticarcinogenic Agents/pharmacology ; Cell Line, Tumor ; Cholestanols/pharmacology ; Cholesterol/metabolism ; Histamine/metabolism ; Humans ; Imidazoles/pharmacology ; Mice
Chemical Substances	5-hydroxy-6-(2-(1H-imidazol-4-yl)ethylamino)cholestan-3-ol ; Anticarcinogenic Agents ; Cholestanols ; Imidazoles ; Histamine (820484N8I3) ; Cholesterol (97C5T2UQ7J)
Language	English
Publishing date	2016-04-15
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Review
ZDB-ID	184237-7
ISSN	1470-8752 ; 0300-5127
ISSN (online)	1470-8752
ISSN	0300-5127
DOI	10.1042/BST20150232
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Article ; Online: The Effects of Cholesterol-Derived Oncometabolites on Nuclear Receptor Function in Cancer.

Silvente-Poirot, Sandrine / Dalenc, Florence / Poirot, Marc

Cancer research

2018 Volume 78, Issue 17, Page(s) 4803–4808

Abstract: Epidemiologic studies are controversial concerning the roles played by cholesterol in cancer risk and development, possibly as it is not cholesterol per se that is pathologic in cancers. Indeed, recent data reveal that the cholesterol metabolism in ... ...

Abstract	Epidemiologic studies are controversial concerning the roles played by cholesterol in cancer risk and development, possibly as it is not cholesterol per se that is pathologic in cancers. Indeed, recent data reveal that the cholesterol metabolism in cancer cells can generate endogenous oncopromoter metabolites at higher levels compared with normal tissues and/or can be deregulated in the production of endogenous oncosuppressor metabolites in an opposite way. These metabolites are oxysterols, which are cholesterol oxygenation products generated by enzymatic and/or autoxidation processes. All these oxysterols are new classes of estrogen, glucocorticoid, or liver X nuclear receptor ligands, and their protumor action on their cognate receptors could explain some drug resistance, while treatment with antitumor metabolites could complement their deficiency in cancers and restore their action on their nuclear receptor. Given that hypercholesterolemia and high intakes of cholesterol-rich foods or processed foods can generate these oxysterols, their importance in cancer risk or development in overweight and obese people is to be considered. The discovery of these cholesterol-derived metabolites and the identification of the nuclear receptors mediating their pro- or antitumor activities are important findings, which should have major implications in the diagnosis, prevention, and treatment of different cancers and open new areas of research.
MeSH term(s)	Cholesterol/metabolism ; Diet, High-Fat/adverse effects ; Humans ; Ligands ; Lipid Peroxidation/genetics ; Metabolome/genetics ; Neoplasms/epidemiology ; Neoplasms/etiology ; Neoplasms/metabolism ; Obesity/complications ; Obesity/epidemiology ; Obesity/metabolism ; Overweight/complications ; Overweight/epidemiology ; Overweight/metabolism ; Oxysterols/metabolism ; Risk Factors
Chemical Substances	Ligands ; Oxysterols ; Cholesterol (97C5T2UQ7J)
Language	English
Publishing date	2018-08-17
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Review
ZDB-ID	1432-1
ISSN	1538-7445 ; 0008-5472
ISSN (online)	1538-7445
ISSN	0008-5472
DOI	10.1158/0008-5472.CAN-18-1487
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