{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,17]],"date-time":"2026-09-17T09:13:40Z","timestamp":1789636420902,"version":"4.0.0"},"reference-count":202,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2023,7,20]],"date-time":"2023-07-20T00:00:00Z","timestamp":1689811200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This review delves into the investigation of the biological activity and structural diversity of steroids and related isoprenoid lipids. The study encompasses various natural compounds, such as steroids with aromatic ring(s), steroid phosphate esters derived from marine invertebrates, and steroids incorporating halogen atoms (I, Br, or Cl). These compounds are either produced by fungi or fungal endophytes or found in extracts of plants, algae, or marine invertebrates. To assess the biological activity of these natural compounds, an extensive examination of referenced literature sources was conducted. The evaluation encompassed in vivo and in vitro studies, as well as the utilization of the QSAR method. Numerous compounds exhibited notable properties such as strong anti-inflammatory, anti-neoplastic, anti-proliferative, anti-hypercholesterolemic, anti-Parkinsonian, diuretic, anti-eczematic, anti-psoriatic, and various other activities. Throughout the review, 3D graphs illustrating the activity of individual steroids are presented alongside images of selected terrestrial or marine organisms. Additionally, the review provides explanations for specific types of biological activity associated with these compounds. The data presented in this review hold scientific interest for academic science as well as practical implications in the fields of pharmacology and practical medicine. The analysis of the biological activity and structural diversity of steroids and related isoprenoid lipids provides valuable insights that can contribute to advancements in both theoretical understanding and applied research.<\/jats:p>","DOI":"10.3390\/molecules28145549","type":"journal-article","created":{"date-parts":[[2023,7,21]],"date-time":"2023-07-21T01:58:38Z","timestamp":1689904718000},"page":"5549","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":47,"title":["Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4603-8704","authenticated-orcid":false,"given":"Valery M.","family":"Dembitsky","sequence":"first","affiliation":[{"name":"Centre for Applied Research, Innovation and Entrepreneurship, Lethbridge College, 3000 College Drive South, Lethbridge, AB T1K 1L6, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,7,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"637","DOI":"10.1016\/j.bbalip.2011.06.009","article-title":"Lipid classification, structures, and tools","volume":"1811","author":"Fahy","year":"2011","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1007\/s12013-020-00947-w","article-title":"Lipids composition in plant membranes","volume":"78","author":"Hanaka","year":"2020","journal-title":"Cell Biochem. Biophys."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"S97","DOI":"10.1105\/tpc.001461","article-title":"Brassinosteroids and plant steroid hormone signaling","volume":"14","author":"Bishop","year":"2002","journal-title":"Plant Cell"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1016\/j.jsbmb.2010.12.009","article-title":"Biosynthesis and metabolism of steroids in molluscs","volume":"127","author":"Fernandes","year":"2011","journal-title":"J. Steroid Biochem. Mol. Biol."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1016\/j.steroids.2012.03.015","article-title":"Steroid biosynthesis and prostate cancer","volume":"77","author":"Sharifi","year":"2012","journal-title":"Steroids"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/j.steroids.2015.03.016","article-title":"Steroid biosynthesis in adipose tissue","volume":"103","author":"Li","year":"2015","journal-title":"Steroids"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1783","DOI":"10.1351\/pac198961101783","article-title":"Nomenclature of steroids","volume":"61","author":"Moss","year":"1989","journal-title":"Pure Appl. Chem."},{"key":"ref_8","unstructured":"Russell, C.A., and Roberts, G.K. (2005). Chemical History: Reviews of the Recent Literature, RSC Publ."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Makin, H.L.J., Gower, D.B., and Kirk, D.N. (1995). Steroid Analysis, Springer.","DOI":"10.1007\/978-94-017-3078-5"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"e1700452","DOI":"10.1002\/cbdv.201700452","article-title":"Protostane-type triterpenoids from Alisma orientale","volume":"14","author":"Li","year":"2017","journal-title":"Chem. Biodivers."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"4044","DOI":"10.3390\/md13074044","article-title":"Biological activity of recently discovered halogenated marine natural products","volume":"13","author":"Gribble","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2301","DOI":"10.3390\/md8082301","article-title":"Halogenated compounds from marine algae","volume":"8","author":"Cabrita","year":"2010","journal-title":"Mar. Drugs"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Ermolenko, E.V., Imbs, A.B., Gloriozova, T.A., Poroikov, V.V., Sikorskaya, T.V., and Dembitsky, V.M. (2020). Chemical diversity of soft coral steroids and their pharmacological activities. Mar. Drugs, 18.","DOI":"10.3390\/md18120613"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"137000","DOI":"10.1016\/j.scitotenv.2020.137000","article-title":"Halogenated natural products in birds associated with the marine environment: A review","volume":"717","author":"Mello","year":"2020","journal-title":"Sci. Total Environ."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Morais, T., Cotas, J., Pacheco, D., and Pereira, L. (2021). Seaweeds compounds: An ecosustainable source of cosmetic ingredients?. Cosmetics, 8.","DOI":"10.3390\/cosmetics8010008"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"37","DOI":"10.31665\/JFB.2018.2139","article-title":"Edible brown seaweeds: A review","volume":"2","author":"Sanjeewa","year":"2018","journal-title":"J. Food Bioact."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Sohn, S.-I., Rathinapriya, P., Balaji, S., Jaya Balan, D., Swetha, T.K., Durgadevi, R., Alagulakshmi, S., Singaraj, P., and Pandian, S. (2021). Phytosterols in seaweeds: An overview on biosynthesis to biomedical applications. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms222312691"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.aquaculture.2019.04.004","article-title":"Aquaculture: An overview of chemical ecology of seaweeds (food species) in natural products","volume":"507","author":"Gnanavel","year":"2019","journal-title":"Aquaculture"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1186\/s43014-022-00103-2","article-title":"Global seaweed farming and processing in the past 20 years","volume":"4","author":"Zhang","year":"2022","journal-title":"Food Prod. Process. Nutr."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/B978-0-12-817901-7.00005-8","article-title":"Antioxidant, anti-inflammatory and anticancer potential of natural bioactive compounds from seaweeds","volume":"63","author":"Sakthivel","year":"2019","journal-title":"Stud. Nat. Prod. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"4663","DOI":"10.1007\/s00253-018-8968-7","article-title":"Naturally occurring aromatic steroids and their biological activities","volume":"102","author":"Dembitsky","year":"2018","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_22","unstructured":"Kadis, B.M. (1957). Synthesis of Steroid Precursors. [Ph.D. Thesis, Iowa State University]."},{"key":"ref_23","unstructured":"Taub, D. (1973). Total Synthesis of Natural Products, John Wiley & Sons, Inc."},{"key":"ref_24","unstructured":"Rutherford, F.J. (1972). Ceric Oxidations of Aromatic Steroids and Related Compounds. [Ph.D. Thesis, University of Edinburgh]."},{"key":"ref_25","unstructured":"Niven, S.J. (1999). The Origins and Occurrence of Estrogenic A-Ring Aromatic Steroids in U.K. Sewage Treatment Works Effluents. [Ph.D. Thesis, University of Plymouth]."},{"key":"ref_26","unstructured":"Gupta, R.R., and Jain, M. (2000). Aliphatic and Aromatic Hydrocarbons, Steroids, Carbohydrates, Springer."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"117366","DOI":"10.1016\/j.fuel.2020.117366","article-title":"Novel parameters derived from alkylchrysenes to differentiate severe biodegradation influence on molecular compositions in crude oils","volume":"268","author":"Huang","year":"2020","journal-title":"Fuel"},{"key":"ref_28","first-page":"376","article-title":"Aromatic steroids as a tool in geochemical interpretation","volume":"71","author":"Matyasik","year":"2015","journal-title":"Nafta-Gaz"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"278","DOI":"10.1080\/15275922.2013.843617","article-title":"Aromatic steroids in crude oils and petroleum products and their applications in forensic oil spill identification","volume":"14","author":"Yang","year":"2013","journal-title":"Environ. Forensics"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1016\/j.orggeochem.2011.02.007","article-title":"New aromatic steroids distinguish Paleozoic from Mesozoic oil","volume":"42","author":"Barbanti","year":"2011","journal-title":"Org. Geochem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"105111","DOI":"10.1016\/j.marpetgeo.2021.105111","article-title":"Aromatic compounds in lacustrine sediments from the Lower Cretaceous Jiufotang formation, Chaoyang basin (NE China)","volume":"129","author":"Li","year":"2021","journal-title":"Mar. Pet. Geol."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Lednicer, D. (2010). Steroid Chemistry at a Glance, John Wiley & Sons, Inc.","DOI":"10.1002\/9780470973639"},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Gianguzza, A., Pelizetti, E., and Sammartano, S. (2000). Chemical Processes in Marine Environments, Springer.","DOI":"10.1007\/978-3-662-04207-6"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Killops, S., and Killops, V. (2004). Front Matter, in Introduction to Organic Geochemistry, Blackwell Publishing Ltd.","DOI":"10.1002\/9781118697214"},{"key":"ref_35","first-page":"362","article-title":"Estrogenic hormones: Their clinical usage","volume":"49","author":"Fluhmann","year":"1938","journal-title":"Calif. West. Med."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"819","DOI":"10.1001\/jama.1923.02650100027012","article-title":"An ovarian hormone: Preliminary report on its localization, extraction and partial purification, and action in test animals","volume":"81","author":"Edgar","year":"1923","journal-title":"J. Am. Med. Assoc."},{"key":"ref_37","first-page":"329","article-title":"Folliculin from urine of pregnant women","volume":"90","author":"Doisy","year":"1929","journal-title":"Am. J. Phys."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"879","DOI":"10.1007\/BF01506919","article-title":"\u00dcber \u201cProgynon\u201d ein krystallisiertes weibliches Sexualhormon","volume":"17","author":"Butenandt","year":"1929","journal-title":"Naturwissenschaften"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1515\/bchm2.1930.191.3-4.140","article-title":"\u00dcber physikalische und chemische Eigenschaften des krystallisierten Follikelhormons. Untersuchungen \u00fcber das weibliche Sexualhormon","volume":"191","author":"Butenandt","year":"1930","journal-title":"Hoppe-Seyler\u2019s Zeit. Physiol. Chem."},{"key":"ref_40","first-page":"1417","article-title":"Tokokinine, Stoff mit sexualhormonartiger Wirkung aus Pflanzenzellen","volume":"22","author":"Dohrn","year":"1926","journal-title":"Med. Klin."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1515\/bchm2.1933.218.1-2.104","article-title":"\u00dcber die Darstellung eines krystallisierten pflanzlichen Tokokinins (Thelykinins) und seine Identifizierung mit dem \u03b1-Follikelhormon. Untersuchungen \u00fcber das weibliche Sexualhormon","volume":"218","author":"Butenandt","year":"1933","journal-title":"Hoppe Seyler\u2019s Z. Physiol. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"766","DOI":"10.1038\/131766b0","article-title":"An oestrogenic substance from plant material","volume":"131","author":"Skarzynski","year":"1933","journal-title":"Nature"},{"key":"ref_43","first-page":"71","article-title":"Mammalian sex hormones in plants","volume":"43","author":"Janeczko","year":"2005","journal-title":"Folia Histochem. Cytobiol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1007\/BF00190004","article-title":"The occurrence of estrogens in relation to reproductive processes in flowering plants","volume":"4","author":"Zhang","year":"1991","journal-title":"Sex. Plant Reprod."},{"key":"ref_45","first-page":"215","article-title":"The changes of steroidal sex hormone\u2014Testosterone contents in reproductive organs of Lilium davidii Duch","volume":"36","author":"Yin","year":"1994","journal-title":"Acta Bot. Sin."},{"key":"ref_46","first-page":"733","article-title":"Steroid alkaloids. LXVI. New alkaloids from the husks of Holarrhena floribunda (G. Don) Dur. and Schinz: Holarrheline, holadienine, holaromine and holaline","volume":"25","author":"Janot","year":"1967","journal-title":"Ann. Pharm. Fr."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"774","DOI":"10.1038\/188774a0","article-title":"Miroestrol\u2014An estrogen fromthe plant Pueraria mirifica","volume":"188","author":"Cain","year":"1960","journal-title":"Nature"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1045","DOI":"10.1016\/S0031-9422(97)00046-0","article-title":"Withanolides from Jaborosa leucotricha","volume":"45","author":"Misico","year":"1997","journal-title":"Phytochemistry"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1644","DOI":"10.1021\/np070197+","article-title":"Withanolides from Jaborosa laciniata","volume":"70","author":"Cirigliano","year":"2007","journal-title":"J. Nat. Prod."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1772","DOI":"10.1021\/np50100a017","article-title":"New norcucurbitacin and heptanorcucurbitacin glucosides from Fevillea trilobata","volume":"56","author":"Valente","year":"1993","journal-title":"J. Nat. Prod."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"722","DOI":"10.1248\/cpb.9.722","article-title":"Studies on the steroidal components of domestic plants. XXXV. Structure of meteogenin","volume":"9","author":"Igarashi","year":"1961","journal-title":"Chem. Pharm. Bull."},{"key":"ref_52","first-page":"729","article-title":"Studies on the steroidal components of domestic plants. XLII. Narthogenin, isonarthogenin and neonogiragenin, three new sapogenins of metanarthecium luteoviride MAXIM","volume":"9","author":"Minato","year":"1961","journal-title":"Chem. Pharm. Bull."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"376","DOI":"10.1007\/BF00630337","article-title":"Luvigenin and hecogenin from the leaves of Yucca gloriosa","volume":"27","author":"Pkheidze","year":"1991","journal-title":"Chem. Nat. Compd."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s11101-014-9381-1","article-title":"Steroidal saponins from the genus Allium","volume":"15","author":"Sobolewska","year":"2016","journal-title":"Phytochem. Rev."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"2885","DOI":"10.1248\/cpb.40.2885","article-title":"Structures of cayaponosides A, B, C and D, glucosides of new norcucurbitacins in the roots of Cayaponia tayuya","volume":"40","author":"Himeno","year":"1992","journal-title":"Chem. Pharm. Bull."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2295","DOI":"10.1248\/cpb.42.2295","article-title":"Studies on the constituents of the root of Cayaponia tayuya (Vell) Cogn. I. Structures of cayaponosides, new 29-Nor-1,2,3,4,5,10-hexadehydro-cucurbitacin glucosides","volume":"42","author":"Himeno","year":"1994","journal-title":"Chem. Pharm. Bull."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"284","DOI":"10.1248\/bpb.18.284","article-title":"Inhibitory effects of cucurbitane triterpenoids on Epstein-Barr virus activation and two stage carcinogenesis of skin tumor. II","volume":"18","author":"Konoshima","year":"1995","journal-title":"Biol. Pharm. Bull."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1148","DOI":"10.1248\/cpb.52.1148","article-title":"Two cangorosin A type triterpene dimers from Maytenus chuchuhuasca","volume":"52","author":"Shirota","year":"2004","journal-title":"Chem. Pharm. Bull."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1251","DOI":"10.1177\/1535370213494563","article-title":"Maytenus ilicifolia dry extract protects normal cells, induces apoptosis, and regulates Bcl-2 in human cancer cells","volume":"238","author":"Oliveira","year":"2013","journal-title":"Exp. Biol. Med."},{"key":"ref_60","first-page":"285","article-title":"Etnobotanica no Rio Grande do Sul: Analise comparative entre o conhecimento original eatual sobre as plantas medicinais nativas","volume":"56","author":"Vendruscolo","year":"2005","journal-title":"Pesqui. Bot."},{"key":"ref_61","first-page":"56","article-title":"Plantas medicinais usadas pela populacao do municipio de Santo Antonio de Leverger, Mato Grosso, Brasil","volume":"79","author":"Goncalves","year":"1998","journal-title":"Rev. Bras. Farm."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.bse.2004.06.014","article-title":"C-32 triterpenes from Taxodium ascendens","volume":"33","author":"Si","year":"2005","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1543","DOI":"10.1126\/science.1074225","article-title":"Natural product terpenoids in Eocene and Miocene conifer fossils","volume":"297","author":"Otto","year":"2012","journal-title":"Science"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"317","DOI":"10.21273\/HORTSCI17045-22","article-title":"Research status and trends of Taxodium distichum","volume":"58","author":"Guo","year":"2023","journal-title":"HortScience"},{"key":"ref_65","first-page":"1571","article-title":"Two ring-A aromatized bile acids from the marine sponge Sollasella moretonensis","volume":"5","author":"Lu","year":"2010","journal-title":"Nat. Prod. Commun."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1113","DOI":"10.1042\/bst0011113","article-title":"The dehydrogenation of the steroid nucleus by human-gut bacteria","volume":"1","author":"Goddard","year":"1973","journal-title":"Biochem. Soc. Trans."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"12593","DOI":"10.1016\/S0040-4020(01)89392-3","article-title":"Hapaioside: A 19-norpregnane glycoside from the sponge Cribrochalina olemda","volume":"50","author":"Yeung","year":"1994","journal-title":"Tetrahedron"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"1524","DOI":"10.1021\/np900177m","article-title":"Reversal of fluconazole resistance by sulfated sterols from the marine sponge Topsentia sp.","volume":"72","author":"Li","year":"2009","journal-title":"J. Nat. Prod."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1021\/np100562n","article-title":"Steroids with aromatic A rings from the Hainan soft coral Dendronephthya studeri Ridley","volume":"74","author":"Yan","year":"2011","journal-title":"J. Nat. Prod."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"7978","DOI":"10.1021\/jo801198u","article-title":"Isolation, biological significance, synthesis, and cytotoxic evaluation of new natural parathiosteroids A-C and analogues from the soft coral Paragorgia sp.","volume":"73","author":"Poza","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"1491","DOI":"10.1021\/np980199h","article-title":"Phycomysterols and other sterols from the fungus Phycomyces blakesleeanus","volume":"61","author":"Barrero","year":"1998","journal-title":"J. Nat. Prod."},{"key":"ref_72","first-page":"1243","article-title":"A new pyrrolidine derivative and steroids from an algicolous Gibberella zeae strain","volume":"6","author":"Liu","year":"2011","journal-title":"Nat. Prod. Commun."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"10954","DOI":"10.1021\/acs.joc.0c02049","article-title":"Asperfloketals A and B, the first two ergostanes with rearranged A and D rings: From the sponge-associated Aspergillus flocculosus","volume":"86","author":"Jiao","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1760","DOI":"10.1021\/np0604026","article-title":"26,27-Cyclosterols and other polyoxygenated sterols from a marine sponge Topsentia sp.","volume":"69","author":"Luo","year":"2006","journal-title":"J. Nat. Prod."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"2803","DOI":"10.1016\/j.tetlet.2016.05.050","article-title":"An unusual 1(10\u219219)abeo steroid from a jellyfish-derived fungus","volume":"57","author":"Kim","year":"2016","journal-title":"Tetrahedron Lett."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"2128","DOI":"10.1021\/acs.jnatprod.5b00170","article-title":"Endophytic Diaporthe sp. LG23 produces a potent antibacterial tetracyclic triterpenoid","volume":"78","author":"Li","year":"2015","journal-title":"J. Nat. Prod."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"9806","DOI":"10.1021\/es202606d","article-title":"Steroidal aromatic \u2018naphthenic acids\u2019 in oil sands process affected water: Structural comparisons with environmental estrogens","volume":"45","author":"Rowland","year":"2011","journal-title":"Environ. Sci. Technol."},{"key":"ref_78","doi-asserted-by":"crossref","unstructured":"Pounina, T.A., Gloriozova, T.A., Savidov, N., and Dembitsky, V.M. (2021). Sulfated and sulfur-containing steroids and their pharmacological profile. Mar. Drugs, 19.","DOI":"10.3390\/md19050240"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"4486","DOI":"10.1021\/ol3019874","article-title":"Phorone A and isophorbasone A, sesterterpenoids isolated from the marine sponge Phorbas sp.","volume":"14","author":"Wang","year":"2012","journal-title":"Org. Lett."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"371","DOI":"10.1021\/ja908626k","article-title":"Chemical, and biological studies of nakiterpiosin and nakiterpiosinone","volume":"132","author":"Gao","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"686","DOI":"10.1021\/np0205506","article-title":"New sesquiterpene quinols from a Micronesian sponge, Aka sp.","volume":"66","author":"Venugopal","year":"2003","journal-title":"J. Nat. Prod."},{"key":"ref_82","first-page":"127","article-title":"Withanolides and related steroids","volume":"94","author":"Misico","year":"2011","journal-title":"Prog. Chem. Org. Nat. Prod."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"9039","DOI":"10.1016\/S0040-4020(00)00758-4","article-title":"New triterpene-ketides (Merotriterpenes), haliclotriol A and B, from an Indo\u2013Pacific Haliclona sponge","volume":"56","author":"Crews","year":"2000","journal-title":"Tetrahedron"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"1451","DOI":"10.1021\/np300345j","article-title":"Halicloic acids A and B isolated from the marine sponge Haliclona sp. collected in the Philippines inhibit indoleamine 2,3-dioxygenase","volume":"75","author":"Williams","year":"2012","journal-title":"J. Nat. Prod."},{"key":"ref_85","doi-asserted-by":"crossref","unstructured":"Kinghorn, A., Falk, H., Gibbons, S., and Kobayashi, J. (2017). Progress in the Chemistry of Organic Natural Products, Springer.","DOI":"10.1007\/978-3-319-49712-9"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/j.orggeochem.2012.06.008","article-title":"Characterization of aromatic steroids and hopanoids in marine and lacustrine crude oils using comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry (GCxGC-TOFMS)","volume":"53","author":"Oliveira","year":"2012","journal-title":"Org. Geochem."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1016\/j.orggeochem.2006.10.007","article-title":"Contrasted distributions of triterpene derivatives in the sediments of Lake Ca\u00e7\u00f3 reflect paleoenvironmental changes during the last 20,000 yrs in NE Brazil","volume":"38","author":"Jacob","year":"2007","journal-title":"Org. Geochem."},{"key":"ref_88","unstructured":"Nakanishi, K., Goto, T., It\u00f4, S., Natori, S., and Nozoe, S. (1974). Natural Products Chemistry, Academic Press."},{"key":"ref_89","unstructured":"Zuhrotun, A., Suganda, A.G., and Nawawi, A. (2010, January 21\u201322). Phytochemical study of ketapang bark (Terminalia catappa L.). Proceedings of the International Conference on Medicinal Plants, Surabaya, Indonesia."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"577","DOI":"10.1042\/bj0300577","article-title":"Some notes on the isolation of oestrone and equilin from the urine of pregnant mares","volume":"30","author":"Beall","year":"1936","journal-title":"Biochem. J."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1016\/S0021-9258(18)73874-X","article-title":"Pregnant mares\u2019 sulfate from the urine of the isolation of estrone","volume":"126","author":"Schachter","year":"1938","journal-title":"J. Biol. Chem."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"974","DOI":"10.1021\/ja01873a513","article-title":"The total synthesis of the sex hormone equilenin","volume":"61","author":"Bachmann","year":"1939","journal-title":"J. Am. Chem. Soc."},{"key":"ref_93","unstructured":"Fritz, M.A., and Speroff, L. (2012). Clinical Gynecologic Endocrinology and Infertility, Lippincott Williams & Wilkin."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"146","DOI":"10.1016\/j.sajb.2016.12.021","article-title":"Enzymatic activity of endophytic fungi from the medicinal plants Terminalia catappa, Terminalia mantaly and Cananga odorata","volume":"109","author":"Toghueo","year":"2017","journal-title":"S. Afr. J. Bot."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"1264","DOI":"10.20546\/ijcmas.2017.602.142","article-title":"Production of cellulolytic enzymes by endophytic fungi isolated from Cameroonian medicinal plants","volume":"6","author":"Toghueo","year":"2017","journal-title":"Int. J. Curr. Microbiol. Appl. Sci."},{"key":"ref_96","first-page":"S1","article-title":"New diterpene isolated from a sponge of genus Strongylophora","volume":"82","author":"Parrish","year":"2016","journal-title":"Planta Med."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"2133","DOI":"10.1021\/np049793j","article-title":"Natural aromatic steroids as potential molecular fossils from the fruiting bodies of the ascomycete Daldinia concentrica","volume":"67","author":"Qin","year":"2004","journal-title":"J. Nat. Prod."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"575","DOI":"10.1042\/bst0110575","article-title":"The geochemistry of terpenoids and steroids","volume":"11","author":"Brassell","year":"1983","journal-title":"Biochem. Soc. Trans."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1007\/BF02641087","article-title":"Geochemistry of lipids","volume":"43","author":"Breger","year":"1966","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1016\/j.orggeochem.2016.01.008","article-title":"Palaeozoic oil\u2013source correlation in the Tarim Basin, NW China: A review","volume":"94","author":"Huang","year":"2016","journal-title":"Org. Geochem."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"8823","DOI":"10.1021\/acs.energyfuels.7b00454","article-title":"Geochemical evolution of occluded hydrocarbons inside geomacromolecules: A review","volume":"31","author":"Cheng","year":"2017","journal-title":"Energy Fuel"},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"1539","DOI":"10.1021\/ol5000023","article-title":"Cinanthrenol A, an estrogenic steroid containing phenanthrene nucleus, from a marine sponge Cinachyrella sp.","volume":"16","author":"Machida","year":"2014","journal-title":"Org. Lett."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"3313","DOI":"10.1016\/S0040-4039(01)81893-1","article-title":"C26-C29 triaromatic steroid derivatives in sediments and petroleum","volume":"22","author":"Ludwig","year":"1981","journal-title":"Tetrahedron Lett."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"491","DOI":"10.1126\/science.217.4559.491","article-title":"Chemical fossils: The geological fate of steroids","volume":"217","author":"Mackenzie","year":"1982","journal-title":"Science"},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"8276","DOI":"10.1039\/c2ob26191j","article-title":"Triterpenoids functionalized at C-2 as diagenetic transformation products of 2,3-dioxygenated triterpenoids from higher plants in buried wood","volume":"10","author":"Schnell","year":"2012","journal-title":"Org. Biomol. Chem."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"1504","DOI":"10.1021\/ol100144t","article-title":"Aromatized C-2 oxygenated triterpenoids as indicators for a new transformation pathway in the environment","volume":"12","author":"Schaeffer","year":"2010","journal-title":"Org. Lett."},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"1","DOI":"10.2174\/2210290601304010001","article-title":"Ethnobotany, phytochemistry, and biological activities of Taxodium rich","volume":"4","author":"Su","year":"2013","journal-title":"Pharm. Crops"},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1130\/0016-7606(1961)72[175:DOTEIS]2.0.CO;2","article-title":"Distribution of the elements in some major units of the Earth\u2019s crust","volume":"72","author":"Turekian","year":"1961","journal-title":"GSA Bull."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1016\/j.aca.2016.02.047","article-title":"Determination of phosphorus in natural waters: A historical review","volume":"918","author":"Worsfold","year":"2016","journal-title":"Anal. Chim. Acta"},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"552","DOI":"10.1038\/ngeo2466","article-title":"Emergence of modern continental crust about 3 billion years ago","volume":"8","author":"Dhuime","year":"2015","journal-title":"Nat. Geosci."},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"660","DOI":"10.1002\/anie.196906601","article-title":"Phosphorus: From elemental light to chemical element","volume":"8","author":"Krafft","year":"1969","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"927","DOI":"10.1021\/cr950243n","article-title":"Comparison of phosphorus and silicon: Hypervalency, stereochemistry, and reactivity","volume":"96","author":"Holmes","year":"1996","journal-title":"Chem. Rev."},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"981","DOI":"10.1080\/00206814.2016.1240049","article-title":"Apatite fission track geochronology of the Southern Hunan province across the Shi-Hang Belt: Insights into the Cenozoic dynamic topography of South China","volume":"59","author":"Su","year":"2017","journal-title":"Int. Geol. Rev."},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"121","DOI":"10.4161\/biom.18790","article-title":"Calcium orthophosphates: Occurrence, properties, biomineralization, pathological calcification and biomimetic applications","volume":"1","author":"Dorozhkin","year":"2011","journal-title":"Biomatter"},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"113","DOI":"10.2113\/GSELEMENTS.4.2.113","article-title":"Phosphates, and nuclear waste storage","volume":"4","author":"Oelkers","year":"2008","journal-title":"Elements"},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"67399","DOI":"10.2138\/rmg.2002.48.18","article-title":"Phosphates as nuclear waste forms","volume":"48","author":"Ewing","year":"2002","journal-title":"Rev. Mineral. Geochem."},{"key":"ref_117","first-page":"110","article-title":"Luminescence of apatite from different rock types","volume":"184","author":"Portnov","year":"1969","journal-title":"Dokl. Akad. Nauk SSSR"},{"key":"ref_118","doi-asserted-by":"crossref","first-page":"3028","DOI":"10.1007\/s10853-008-2527-z","article-title":"Calcium orthophosphate cements for biomedical application","volume":"43","author":"Dorozhkin","year":"2008","journal-title":"J. Mater. Sci."},{"key":"ref_119","doi-asserted-by":"crossref","first-page":"1465","DOI":"10.1016\/j.biomaterials.2009.11.050","article-title":"Bioceramics of calcium orthophosphates","volume":"31","author":"Dorozhkin","year":"2010","journal-title":"Biomaterials"},{"key":"ref_120","doi-asserted-by":"crossref","unstructured":"Yeagle, P.L. (2016). The Membranes of Cells, Academic Press.","DOI":"10.1016\/B978-0-12-800047-2.00005-X"},{"key":"ref_121","doi-asserted-by":"crossref","first-page":"3130","DOI":"10.1002\/1521-3773(20020902)41:17<3130::AID-ANIE3130>3.0.CO;2-1","article-title":"Biological and medical significance of calcium phosphates","volume":"41","author":"Dorozhkin","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_122","first-page":"79","article-title":"Phosphated and sulfated marine polyhydroxylated steroids from the starfish Tremaster novaecaledoniae","volume":"123","author":"Minale","year":"1993","journal-title":"Gazz. Chim. Ital."},{"key":"ref_123","doi-asserted-by":"crossref","first-page":"3885","DOI":"10.1016\/S0040-4020(01)00259-9","article-title":"Isolation and structure elucidation of two phosphorylated sterol sulfates, MT1-MMP inhibitors from a marine sponge Cribrochalina sp.: Revision of the structures of haplosamates A and B","volume":"57","author":"Fujita","year":"2001","journal-title":"Tetrahedron"},{"key":"ref_124","doi-asserted-by":"crossref","first-page":"998","DOI":"10.1016\/j.steroids.2011.03.013","article-title":"Desulfohaplosamate, a new phosphate-containing steroid from Dasychalina sp., is a selective cannabinoid CB2 receptor ligand","volume":"76","author":"Chianese","year":"2011","journal-title":"Steroids"},{"key":"ref_125","doi-asserted-by":"crossref","unstructured":"Tytgat, G.N.J., and Mulder, C.J.J. (1997). Procedures in Hepatogastroenterology, Springer.","DOI":"10.1007\/978-94-011-5702-5"},{"key":"ref_126","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/0005-2760(70)90151-7","article-title":"Testosterone 17-phosphate and 19-nortestosterone 17-phosphate as substrate for rabbit prostate phosphatases","volume":"218","author":"Delrio","year":"1970","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_127","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1016\/S0003-2670(96)00400-X","article-title":"Chemiluminescence assay of alkaline phosphatase using cortisol-21-phosphate as substrate and its application to enzyme immunoassays","volume":"337","author":"Kokado","year":"1997","journal-title":"Anal. Chim. Acta"},{"key":"ref_128","doi-asserted-by":"crossref","first-page":"310","DOI":"10.1016\/j.atherosclerosis.2011.09.002","article-title":"Phosphate: The new cholesterol? The role of the phosphate axis in non-uremic vascular disease","volume":"220","author":"Ellam","year":"2012","journal-title":"Atherosclerosis"},{"key":"ref_129","doi-asserted-by":"crossref","first-page":"783","DOI":"10.1021\/bc980047y","article-title":"Cholesterol phosphate derivatives: Synthesis and incorporation into a phosphatase and calcium-sensitive triggered release liposome","volume":"9","author":"Davis","year":"1998","journal-title":"Bioconjug. Chem."},{"key":"ref_130","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1186\/1476-511X-13-153","article-title":"The effect of two novel cholesterol-lowering agents, disodium ascorbyl phytostanol phosphate and nanostructured aluminosilicate on the expression and activity of P-glycoprotein within Caco-2 cells","volume":"13","author":"Darlington","year":"2014","journal-title":"Lipids Health Dis."},{"key":"ref_131","unstructured":"Kutney, J.P., Pritchard, H.P., and Lukic, T. (2003). Novel Compounds and Compositions Comprising Sterols and\/or Stanols and Cholesterol Biosynthesis Inhibitors and Use Thereof in Treating or Preventing a Variety of Diseases and Conditions. (EP1644399A2), Japan Patent."},{"key":"ref_132","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/S0378-5173(98)00025-8","article-title":"Targeted drug delivery to the brain via phosphonate derivatives I Design, synthesis and evaluation of an anionic chemical delivery system for testosterone","volume":"166","author":"Somogyi","year":"1998","journal-title":"Int. J. Pharm."},{"key":"ref_133","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1002\/pros.2990130405","article-title":"Clinical pharmacology of polyestradiol phosphate","volume":"13","author":"Gunnarsson","year":"1988","journal-title":"Prostate"},{"key":"ref_134","doi-asserted-by":"crossref","first-page":"824","DOI":"10.1016\/j.colsurfa.2017.06.063","article-title":"Preparation and characterization of betamethasone sodium phosphate intercalated layered double hydroxide liposome nanocomposites","volume":"529","author":"Zhang","year":"2017","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_135","doi-asserted-by":"crossref","first-page":"459","DOI":"10.1042\/bj2210459","article-title":"Isolation, and identification of ecdysteroid phosphates and acetylecdysteroid phosphates from developing eggs of the locust, Schistocerca gregaria","volume":"221","author":"Isaac","year":"1984","journal-title":"Biochem. J."},{"key":"ref_136","first-page":"75","article-title":"Ayurvedic medicine: Core concept, therapeutic principles, and current relevance","volume":"86","author":"Chopra","year":"2002","journal-title":"Med. Clin."},{"key":"ref_137","doi-asserted-by":"crossref","first-page":"465","DOI":"10.1093\/ecam\/neh140","article-title":"Ayurveda, and traditional Chinese medicine: A comparative overview","volume":"2","author":"Patwardhan","year":"2005","journal-title":"Evid.-Based Complement. Altern. Med."},{"key":"ref_138","doi-asserted-by":"crossref","first-page":"14","DOI":"10.1186\/s42779-019-0016-4","article-title":"Traditional methods of food habits and dietary preparations in Ayurveda\u2014The Indian system of medicine","volume":"6","author":"Mishra","year":"2019","journal-title":"J. Ethn. Foods"},{"key":"ref_139","doi-asserted-by":"crossref","first-page":"R117","DOI":"10.1111\/j.1750-3841.2008.00966.x","article-title":"Functional properties of honey, propolis, and royal jelly","volume":"73","year":"2008","journal-title":"J. Food Sci."},{"key":"ref_140","doi-asserted-by":"crossref","unstructured":"Dembitsky, V.M. (2021). In silico prediction of steroids and triterpenoids as potential regulators of lipid metabolism. Mar. Drugs, 19.","DOI":"10.3390\/md19110650"},{"key":"ref_141","first-page":"039","article-title":"QSAR study of some natural and synthetic platelet aggregation inhibitors and their pharmacological profile","volume":"12","author":"Dembitsky","year":"2022","journal-title":"J. Appl. Pharm. Sci."},{"key":"ref_142","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.jff.2011.12.007","article-title":"Bioactive compounds and health-promoting properties of royal jelly: A review","volume":"4","author":"Ramadan","year":"2012","journal-title":"J. Funct. Foods"},{"key":"ref_143","first-page":"1","article-title":"Naturally occurring organohalogen compounds\u2014A comprehensive survey","volume":"68","author":"Gribble","year":"1996","journal-title":"Prog. Chem. Org. Nat. Prod."},{"key":"ref_144","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1021\/ar9701777","article-title":"Naturally occurring organohalogen compounds","volume":"31","author":"Gribble","year":"1998","journal-title":"Acc. Chem. Res."},{"key":"ref_145","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1039\/a900201d","article-title":"The diversity of naturally occurring organobromine compounds","volume":"28","author":"Gribble","year":"1999","journal-title":"Chem. Soc. Rev."},{"key":"ref_146","first-page":"1","article-title":"Naturally occurring organohalogen compounds\u2014A comprehensive update","volume":"91","author":"Gribble","year":"2010","journal-title":"Prog. Chem. Org. Nat. Prod."},{"key":"ref_147","doi-asserted-by":"crossref","unstructured":"Wang, C., Du, W., Lu, H., Lan, J., Liang, K., and Cao, S. (2021). A Review: Halogenated compounds from marine Actinomycetes. Molecules, 26.","DOI":"10.3390\/molecules26092754"},{"key":"ref_148","doi-asserted-by":"crossref","unstructured":"Wang, C., Lu, H., Lan, J., Ahammad Zaman, K.H., and Cao, S. (2021). A Review: Halogenated compounds from marine fungi. Molecules, 26.","DOI":"10.3390\/molecules26020458"},{"key":"ref_149","first-page":"363","article-title":"Chlorine containing sesquiterpenes of higher plants","volume":"10","author":"Dembitsky","year":"2002","journal-title":"Chem. Sustain. Dev."},{"key":"ref_150","unstructured":"Dembitsky, V.M., and Tolstikov, G.A. (2003). Natural Organic Halogenated Compounds, Geo-Science."},{"key":"ref_151","first-page":"803","article-title":"Natural halogenated alkanes, cycloalkanes, and their derivatives","volume":"11","author":"Dembitsky","year":"2003","journal-title":"Chem. Sustain. Dev."},{"key":"ref_152","first-page":"451","article-title":"Natural halogenated alkaloids","volume":"11","author":"Dembitsky","year":"2003","journal-title":"Chem. Sustain. Dev."},{"key":"ref_153","first-page":"697","article-title":"Natural halogenated furanones, higher terpenes and steroids","volume":"11","author":"Dembitsky","year":"2003","journal-title":"Chem. Sustain. Dev."},{"key":"ref_154","first-page":"329","article-title":"Natural halogenated non-terpenic C15-acetogenins of sea organisms","volume":"11","author":"Dembitsky","year":"2003","journal-title":"Chem. Sustain. Dev."},{"key":"ref_155","first-page":"557","article-title":"Halogenated phenol compounds in lichens and fungi","volume":"11","author":"Dembitsky","year":"2003","journal-title":"Chem. Sustain. Dev."},{"key":"ref_156","first-page":"567","article-title":"Natural halogenated mononuclear phenol compounds and their derivatives","volume":"11","author":"Dembitsky","year":"2003","journal-title":"Chem. Sustain. Dev."},{"key":"ref_157","doi-asserted-by":"crossref","first-page":"70","DOI":"10.20546\/ijcrbp.2017.411.009","article-title":"Chlorinated plant steroids and their biological activities","volume":"4","author":"Dembitsky","year":"2017","journal-title":"Int. J. Curr. Res. Biosci. Plant Biol."},{"key":"ref_158","doi-asserted-by":"crossref","first-page":"5169","DOI":"10.1016\/S0040-4020(01)88428-3","article-title":"Weitere inhaltsstoffe aus Jaborosa integrifolia Lam. III: Zur Struktur der Jaborosalactone C, D, und E","volume":"24","author":"Tschesche","year":"1968","journal-title":"Tetrahedron"},{"key":"ref_159","doi-asserted-by":"crossref","first-page":"705","DOI":"10.1039\/c0np00045k","article-title":"Natural withanolides: An overview","volume":"28","author":"Chen","year":"2011","journal-title":"Nat. Prod. Rep."},{"key":"ref_160","doi-asserted-by":"crossref","first-page":"648","DOI":"10.1021\/np50034a013","article-title":"Physalolactone C, a new withanolide from Physalis peruviana","volume":"47","author":"Ali","year":"1984","journal-title":"J. Nat. Prod."},{"key":"ref_161","doi-asserted-by":"crossref","first-page":"1029","DOI":"10.1039\/p19810001029","article-title":"Withaperuvin and 4-deoxy-physalolactone, two new ergostane-type steroids from Physalis peruviana (Solanaceae)","volume":"112","author":"Frolow","year":"1981","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_162","doi-asserted-by":"crossref","first-page":"2448","DOI":"10.1248\/cpb.40.2448","article-title":"Three new withanolides, physagulins E, F and G from Physalis angulata L.","volume":"40","author":"Shingu","year":"1992","journal-title":"Chem. Pharm. Bull."},{"key":"ref_163","doi-asserted-by":"crossref","first-page":"2547","DOI":"10.1016\/0031-9422(81)83091-9","article-title":"Chlorinated withanolides from Withania somnifera and Acnistus breviflorus","volume":"20","author":"Nittala","year":"1981","journal-title":"Phytochemistry"},{"key":"ref_164","doi-asserted-by":"crossref","first-page":"3648","DOI":"10.1016\/0031-9422(92)83749-O","article-title":"Withanolide C, A chlorinated withanolide from Withania somnifera","volume":"31","author":"Bessalle","year":"1992","journal-title":"Phytochemistry"},{"key":"ref_165","doi-asserted-by":"crossref","first-page":"633","DOI":"10.1021\/np50018a001","article-title":"Recent Developments in naturally occurring ergostane-type steroids. A Review","volume":"44","author":"Kirson","year":"1981","journal-title":"J. Nat. Prod."},{"key":"ref_166","doi-asserted-by":"crossref","first-page":"554","DOI":"10.1021\/np50074a031","article-title":"New withanolides from Jaborosa magellanica","volume":"54","author":"Fajardo","year":"1991","journal-title":"J. Nat. Prod."},{"key":"ref_167","doi-asserted-by":"crossref","first-page":"12895","DOI":"10.3390\/molecules171112895","article-title":"Secondary metabolites from two species of Tolpis and their biological activities","volume":"17","author":"Triana","year":"2012","journal-title":"Molecules"},{"key":"ref_168","doi-asserted-by":"crossref","first-page":"1745","DOI":"10.1055\/s-2008-1081357","article-title":"Withanolide Z, new chlorinated withanolide from Withania somnifera","volume":"74","author":"Pramanick","year":"2008","journal-title":"Planta Med."},{"key":"ref_169","doi-asserted-by":"crossref","first-page":"509","DOI":"10.1016\/S0031-9422(96)00553-5","article-title":"28-Hydroxywithanolide E from Physalis peruviana","volume":"44","author":"Dinan","year":"1997","journal-title":"Phytochemistry"},{"key":"ref_170","doi-asserted-by":"crossref","first-page":"462","DOI":"10.1016\/j.foodchem.2009.02.061","article-title":"New cytotoxic withanolides from Physalis peruviana","volume":"116","author":"Lan","year":"2009","journal-title":"Food Chem."},{"key":"ref_171","doi-asserted-by":"crossref","first-page":"747","DOI":"10.1021\/np0605541","article-title":"Cytotoxic withanolides from Tubocapsicum anomalum","volume":"70","author":"Hsieh","year":"2007","journal-title":"J. Nat. Prod."},{"key":"ref_172","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1248\/bpb.27.193","article-title":"Trypanocidal constituents in plants. 4. Withanolides from the aerial parts of Physalis angulata","volume":"27","author":"Nagafuji","year":"2004","journal-title":"Biol. Pharm. Bull."},{"key":"ref_173","doi-asserted-by":"crossref","first-page":"1471","DOI":"10.1021\/np030248c","article-title":"15,21-Cyclowithanolides from Jaborosa bergii","volume":"66","author":"Nicotra","year":"2003","journal-title":"J. Nat. Prod."},{"key":"ref_174","doi-asserted-by":"crossref","first-page":"808","DOI":"10.1021\/np070030g","article-title":"Withanolides with phytotoxic activity from Jaborosa caulescens var. caulescens and J. caulescens var. bipinnatifida","volume":"70","author":"Nicotra","year":"2007","journal-title":"J. Nat. Prod."},{"key":"ref_175","doi-asserted-by":"crossref","first-page":"705","DOI":"10.1021\/np50119a008","article-title":"Novel withanolides from Jaborosa sativa","volume":"58","author":"Bonetto","year":"1995","journal-title":"J. Nat. Prod."},{"key":"ref_176","doi-asserted-by":"crossref","first-page":"34","DOI":"10.1248\/cpb.55.34","article-title":"New C28 steroidal glycosides from Tubocapsicum anomalum","volume":"55","author":"Kiyota","year":"2007","journal-title":"Chem. Pharm. Bull."},{"key":"ref_177","doi-asserted-by":"crossref","first-page":"1038","DOI":"10.1248\/cpb.56.1038","article-title":"New C28 steroidal glycosides from Tubocapsicum anomalum","volume":"56","author":"Kiyota","year":"2008","journal-title":"Chem. Pharm. Bull."},{"key":"ref_178","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1039\/P19770000341","article-title":"Naturally occurring steroidal lactones with a 17a-oriented side chain. Structure of withanolide E and related compounds","volume":"1","author":"Glotter","year":"1977","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_179","doi-asserted-by":"crossref","first-page":"1107","DOI":"10.1248\/cpb.38.1107","article-title":"Two new ergostane derivatives from Tubocapsicum anomalum (Solanaceae)","volume":"38","author":"Shingu","year":"1990","journal-title":"Chem. Pharm. Bull."},{"key":"ref_180","doi-asserted-by":"crossref","first-page":"1049","DOI":"10.1021\/np0200109","article-title":"Spiranoid withanolides from Jaborosa odonelliana","volume":"65","author":"Cirigliano","year":"2002","journal-title":"J. Nat. Prod."},{"key":"ref_181","doi-asserted-by":"crossref","first-page":"867","DOI":"10.1515\/znb-2005-0808","article-title":"Spiranoid withanolides from Jaborosa odonelliana and Jaborosa runcinata","volume":"60","author":"Cirigliano","year":"2005","journal-title":"Z. Naturforschung B Chem. Sci."},{"key":"ref_182","doi-asserted-by":"crossref","first-page":"5670","DOI":"10.1002\/anie.200900760","article-title":"Stereochemistry determination by powder X-ray diffraction analysis and NMR spectroscopy residual dipolar couplings","volume":"48","author":"Garcia","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_183","doi-asserted-by":"crossref","first-page":"784","DOI":"10.1039\/D1NP00055A","article-title":"Natural withanolides, an update","volume":"39","author":"Xia","year":"2022","journal-title":"Nat. Prod. Rep."},{"key":"ref_184","doi-asserted-by":"crossref","unstructured":"Moujir, L.M., Llanos, G.G., Araujo, L., Amesty, A., Bazzocchi, I.L., and Jim\u00e9nez, I.A. (2020). Withanolide-type steroids from Withania aristata as potential anti-leukemic agents. Molecules, 25.","DOI":"10.3390\/molecules25235744"},{"key":"ref_185","first-page":"144","article-title":"First isolation of physalins from the genus Saracha of Solanaceae","volume":"53","author":"Ripperger","year":"1998","journal-title":"Pharmazie"},{"key":"ref_186","doi-asserted-by":"crossref","first-page":"1668","DOI":"10.1021\/np50125a004","article-title":"Structural revision of physalin H isolated from Physalis angulata","volume":"58","author":"Makino","year":"1995","journal-title":"J. Nat. Prod."},{"key":"ref_187","doi-asserted-by":"crossref","first-page":"661","DOI":"10.1016\/0031-9422(96)00339-1","article-title":"Upon\u2014Physalin L\u2016 isolated from Physalis minima","volume":"43","author":"Kawai","year":"1996","journal-title":"Phytochemistry"},{"key":"ref_188","doi-asserted-by":"crossref","first-page":"783","DOI":"10.1021\/np0600090","article-title":"Phytotoxic withanolides from Jaborosa rotacea","volume":"69","author":"Nicotra","year":"2006","journal-title":"J. Nat. Prod."},{"key":"ref_189","doi-asserted-by":"crossref","first-page":"1633","DOI":"10.1021\/ol049548r","article-title":"Polychlorinated androstanes from the burrowing sponge Cliona nigricans","volume":"6","author":"Fattorusso","year":"2004","journal-title":"Org. Lett."},{"key":"ref_190","doi-asserted-by":"crossref","first-page":"134","DOI":"10.1007\/BF01984951","article-title":"Aragusterol C: A novel halogenated marine steroid from an Okinawan sponge, Xestospongia sp., possessing potent antitumor activity","volume":"50","author":"Shimura","year":"1994","journal-title":"Experientia"},{"key":"ref_191","doi-asserted-by":"crossref","first-page":"1840","DOI":"10.1248\/cpb.44.1840","article-title":"Marine natural products. XXXVII. Aragusteroketals A and C, two novel cytotoxic steroids from a marine sponge of Xestospongia sp.","volume":"44","author":"Kobayashi","year":"1996","journal-title":"Chem. Pharm. Bull."},{"key":"ref_192","doi-asserted-by":"crossref","unstructured":"Pham, G.N., Kang, D.Y., Kim, M.J., Han, S.J., Lee, J.H., and Na, M. (2021). Isolation of sesquiterpenoids and steroids from the soft coral Sinularia brassica and determination of their absolute configuration. Mar. Drugs, 19.","DOI":"10.3390\/md19090523"},{"key":"ref_193","doi-asserted-by":"crossref","first-page":"3460","DOI":"10.1021\/jo00064a041","article-title":"Three unprecedented chloro steroids from the Maui sponge Strongylacidon sp.: Kiheisterones C, D, and E","volume":"58","author":"Carney","year":"1993","journal-title":"J. Org. Chem."},{"key":"ref_194","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1016\/0040-4020(75)85079-4","article-title":"Disidein, a pentacyclic sesterterpene condensed with an hydroxyhydroquinone moiety, from the sponge Disidea pallescens","volume":"31","author":"Cimino","year":"1975","journal-title":"Tetrahedron"},{"key":"ref_195","doi-asserted-by":"crossref","first-page":"1383","DOI":"10.3390\/md10061383","article-title":"Chalinulasterol, a chlorinated steroid disulfate from the caribbean sponge Chalinula molitba. Evaluation of its role as PXR receptor modulator","volume":"10","author":"Teta","year":"2012","journal-title":"Mar. Drugs"},{"key":"ref_196","doi-asserted-by":"crossref","first-page":"6989","DOI":"10.1016\/j.tet.2003.08.083","article-title":"Nakiterpiosin and nakiterpiosinone, novel cytotoxic C-nor-D-homosteroids from the Okinawan sponge Terpios hoshinota","volume":"60","author":"Teruya","year":"2004","journal-title":"Tetrahedron"},{"key":"ref_197","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/vjch.201960001","article-title":"Highly oxygenated isoprenoid lipids derived from terrestrial and aquatic sources: Origin, structures and biological activities","volume":"57","author":"Vil","year":"2019","journal-title":"Vietnam J. Chem."},{"key":"ref_198","doi-asserted-by":"crossref","first-page":"7191","DOI":"10.1016\/j.tetlet.2008.10.007","article-title":"Topsentiasterol sulfates with novel iodinated and chlorinated side chains from the marine sponge Topsentia sp.","volume":"49","author":"Guzii","year":"2008","journal-title":"Tetrahedron Lett."},{"key":"ref_199","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.molstruc.2011.05.026","article-title":"Biotransformation of stypotriol triacetate by Aspergillus niger","volume":"998","author":"Areche","year":"2011","journal-title":"J. Mol. Struct."},{"key":"ref_200","doi-asserted-by":"crossref","first-page":"645","DOI":"10.1016\/S0040-4039(01)86026-3","article-title":"Starfish saponins II. 22,23-epoxysteroids, minor genins from the starfish Echinaster sepositus","volume":"20","author":"Minale","year":"1979","journal-title":"Tetrahedron Lett."},{"key":"ref_201","doi-asserted-by":"crossref","first-page":"915","DOI":"10.1016\/j.tetlet.2003.11.113","article-title":"Unusual chlorinated pregnanes from the eastern Pacific octocoral Carijoa multiflora","volume":"45","author":"Dort","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref_202","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/S0039-128X(00)00144-6","article-title":"Three new chlorinated marine steroids, yonarasterols G, H and I, isolated from the Okinawan soft coral, Clavularia viridis","volume":"66","author":"Iwashima","year":"2001","journal-title":"Steroids"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/14\/5549\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:15:56Z","timestamp":1760127356000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/14\/5549"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,20]]},"references-count":202,"journal-issue":{"issue":"14","published-online":{"date-parts":[[2023,7]]}},"alternative-id":["molecules28145549"],"URL":"https:\/\/doi.org\/10.3390\/molecules28145549","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,7,20]]}}}