Highly oxygenated isoprenoid lipids derived from fungi and fungal endophytes: Origin and biological activities

Stevenson, 2010, 328 Bruns, 2006, Evolutionary biology: a kingdom revised, Nature, 443, 758, 10.1038/443758a Höller, 2000, Fungi from marine sponges: diversity, biological activity and secondary metabolites, Mycol. Res., 104, 1354, 10.1017/S0953756200003117 Manohar, 2013, Fungal diversity from various marine habitats deduced through culture-independent studies, FEMS Microbiol. Lett., 10.1111/1574-6968.12087 Deng, 2017, Fungal endophytes and their interactions with plants in phytoremediation: a review, Chemosphere, 168, 1100, 10.1016/j.chemosphere.2016.10.097 Miles, 2004 Hall, 2003 Hawksworth, 2017, Fungal diversity revisited: 2.2 to 3.8 million species, Microbiol. Spectr., 5, 10.1128/microbiolspec.FUNK-0052-2016 Dembitsky, 1992, Lipids of lichens, Prog. Lipid Res., 31, 373, 10.1016/0163-7827(92)90002-Z Dembitsky, 1996, Betaine ether-linked glycerolipids: chemistry and biology, Prog. Lipid Res., 35, 1, 10.1016/0163-7827(95)00009-7 Dembitsky, 2014, Naturally occurring bioactive cyclobutane-containing (CBC) alkaloids in fungi, fungal endophytes, and plants, Phytomedicine, 21, 1559, 10.1016/j.phymed.2014.07.005 Dembitsky, 2018, Bioactive cyclobutane-containing alkaloids, J. Nat. Med., 62, 1, 10.1007/s11418-007-0166-3 Dembitsky, 2017, The multiple properties of some of the lichenized Ascomycetes: biological activity and active metabolites, 201 Dembitsky, 2017, Paradigm shifts in fungal secondary metabolite research: unusual fatty acids incorporated into fungal peptides, Int. J. Curr. Res. Biosci. Plant Biol. (India), 4, 7, 10.20546/ijcrbp.2017.412.002 Cole, 2003 Dembitsky, 2011, Natural and synthetic small boron-containing molecules as potential inhibitors of bacterial and fungal quorum sensing, Chem. Rev., 111, 209, 10.1021/cr100093b Dembitsky, 2004, Arsenolipids, Prog. Lipid Res., 43, 403, 10.1016/j.plipres.2004.07.001 Dembitsky, 1991, Identification of fatty acids from Cladonia lichens, Phytochemistry, 30, 4015, 10.1016/0031-9422(91)83455-T Kuklev, 2013, Bioactive acetylenic metabolites, Phytomedicine, 20, 1145, 10.1016/j.phymed.2013.06.009 Mata-Gómez, 2014, Biotechnological production of carotenoids by yeasts: an overview, Microb. Cell Fact., 13, 12, 10.1186/1475-2859-13-12 Dembitsky, 2005, Secondary metabolites of slime molds (myxomycetes), Phytochemistry, 66, 747, 10.1016/j.phytochem.2005.02.017 Dembitsky, 1992, Phospholipid and fatty acid composition of some basidiomycetes, Phytochemistry, 31, 845, 10.1016/0031-9422(92)80026-B Dembitsky, 2018, Naturally occurring aromatic steroids and their biological activities, Appl. Microbiol. Biotechnol., 102, 4663, 10.1007/s00253-018-8968-7 Dembitsky, 2002, Natural halogenated fatty acids: their analogues and derivatives, Prog. Lipid Res., 41, 315, 10.1016/S0163-7827(02)00003-6 Saxena, 2001, Role of fungal enzymes in food processing, Appl. Mycol. Biotech., 1, 353, 10.1016/S1874-5334(01)80015-0 Green, 2011, Industrial fungal enzymes: an occupational allergen perspective, J. Allergy (Cairo), 682574 Dembitsky, 2003, Oxidation, epoxidation and sulfoxidation reactions catalysed by haloperoxidases, Tetrahedron, 59, 4701, 10.1016/S0040-4020(03)00701-4 Sica, 2004, Secosteroids of marine origin, Steroids, 69, 743, 10.1016/j.steroids.2004.09.001 Jäpelt, 2013, Vitamin D in plants: a review of occurrence, analysis, and biosynthesis, Front. Plant Sci., 4, 136, 10.3389/fpls.2013.00136 Grishko, 2016, Structural diversity, natural sources and pharmacological potential of naturally occurring A-seco-triterpenoids studies, Nat. Prod. Chem., 51, 51 Pilz, 2018, Vitamin D: Current guidelines and future outlook, Anticancer Res., 38, 1145 Dickschat, 2017, Lipids: fatty acids and derivatives, polyketides and isoprenoids, Beilstein J. Org. Chem., 13, 793, 10.3762/bjoc.13.78 Pérez-Gil, 2017, Formation of isoprenoids, 1 Bach, 1995, Some new aspects of isoprenoid biosynthesis in plants – a review, Lipids, 30, 191, 10.1007/BF02537822 R.B. Barlow, Structure-activity relationships, Trends Pharm. Sci. 1(1) (1979–1980) 109–111. Bezhentsev, 2017, Web resources for discovery and development of new medicines, Pharm. Chem. J., 51, 91, 10.1007/s11094-017-1563-x Filimonov, 2014, Prediction of the biological activity spectra of organic compounds using the PASS online web resource, Chem. Heterocycl. Comp., 50, 444, 10.1007/s10593-014-1496-1 Filimonov, 2018, Computer-aided prediction of biological activity spectra for chemical compounds: opportunities and limitations, Biom. Chem. Res. Method, 1, e00004, 10.18097/BMCRM00004 Goel, 2018, Pharmacological repositioning of Achyranthes aspera as antidepressant using pharmacoinformatic tools PASS and Pharma Expert: a case study with wet lab validation, SAR QSAR Environ. Res., 29, 69, 10.1080/1062936X.2017.1408683 Levitsky, 2017, Anabolic cyanosteroids and their biological activities – a brief review, World J. Pharm. Pharmaceut. Sci., 6, 127 Murtazalieva, 2017, How good are publicly available web services that predict bioactivity profiles for drug repurposing?, SAR QSAR Environ. Res., 28, 843, 10.1080/1062936X.2017.1399448 Chand, 2011, Structure–bioactivity-relationships and crystallographic analysis of secondary interactions in pregnane-based steroids, J. Chem. Crystallogr., 41, 1901, 10.1007/s10870-011-0200-x Anuradha, 2013, In silico biological activity of steroids from the marine sponge Axinella carteri, Med. Chem. Res., 22, 1142, 10.1007/s00044-012-0119-6 Shamsuzzaman, 2014, Med. Chem. Res., 23, 348, 10.1007/s00044-013-0636-y Fedyushkina, 2014, Prediction of the action of ligands of steroid hormone receptors, Biochem. (Moscow) Suppl. Series B: Biomed. Chem., 89, 53, 10.1134/S1990750814010041 Saikia, 2015, Marine steroids as potential anticancer drug candidates: In silico investigation in search of inhibitors of Bcl-2 andCDK-4/Cyclin D1, Steroids, 102, 7, 10.1016/j.steroids.2015.06.012 Peng, 2014, Hepatoprotective effects of triterpenoids from Ganoderma cochlear, J. Nat. Prod., 77, 737, 10.1021/np400323u Bao, 2018, New natural inhibitors of hexokinase 2 (HK2): Steroids from Ganoderma sinense, Fitoterapia, 125, 123, 10.1016/j.fitote.2018.01.001 Peng, 2015, Ganocochlearic acid A, a rearranged hexanorlanostane triterpenoid, and cytotoxic triterpenoids from the fruiting bodies of Ganoderma cochlear, RSC Adv., 5, 95212, 10.1039/C5RA16796E Wang, 2013, Ophiobolins P-T, five new cytotoxic and antibacterial sesterterpenes from the endolichenic fungus Ulocladium sp, Fitoterapia, 90, 220, 10.1016/j.fitote.2013.08.002 Leon, 2003, Novel cytostatic lanostanoid triterpenes from Ganoderma australe, Helv. Chim. Acta, 86, 3088, 10.1002/hlca.200390251 Yoshikawa, 2002, New lanostanoids, elfvingic acids A-H, from the fruit body of Elfvingia applanata, J. Nat. Prod., 65, 548, 10.1021/np0103160 Kleinwächter, 2001, Colossolactones, new triterpenoid metabolites from a Vietnamese mushroom Ganoderma colossum, J. Nat. Prod., 64, 236, 10.1021/np000437k Hu, 2017, Phomopsterones A and B, two functionalized ergostane-type steroids from the endophytic fungus Phomopsis sp., TJ507A, Org. Lett., 19, 258, 10.1021/acs.orglett.6b03557 Han, 2015, Gloeophyllins A-J, cytotoxic ergosteroids with various skeletons from a Chinese Tibet fungus Gloeophyllum abietinum, Org. Lett., 17, 2538, 10.1021/acs.orglett.5b01080 Zhao, 2017, Bioactive polyketides and 8,14-seco-ergosterol from fruiting bodies of the ascomycete Daldinia childiae, Phytochemistry, 142, 68, 10.1016/j.phytochem.2017.06.020 Ma, 2014, Ganoboninketals A-C, antiplasmodial 3,4-seco-27-norlanostane triterpenes from Ganoderma boninense Pat, J. Nat. Prod., 77, 1847, 10.1021/np5002863 Liu, 2016, Aspterpenacids A and B, two sesterterpenoids from a mangrove endophytic fungus Aspergillus terreus H010, Org. Lett., 18, 1406, 10.1021/acs.orglett.6b00336 Kanhere, 2018, Role of vitamin D on gut microbiota in cystic fibrosis, J. Steroid Biochem. Mol. Biol., 175, 82, 10.1016/j.jsbmb.2016.11.001 Schafer, 2017, Vitamin D and intestinal calcium transport after bariatric surgery, J. Steroid Biochem. Mol. Biol., 173, 202, 10.1016/j.jsbmb.2016.12.012 Fernandes, 1992, Association between physical activity and vitamin D: a narrative literature review, Rev. Assoc. Med. Bras., 63, 550, 10.1590/1806-9282.63.06.550 Bills, 1938, The chemistry of vitamin D, J. Am. Med. Assoc., 110, 2150, 10.1001/jama.1938.62790260002009 Phillips, 2012, Vitamin D4 in mushrooms, PLoS One, 7, e40702, 10.1371/journal.pone.0040702 Hirsch, 2011, Industrial aspects of vitamin D, 73 Chen, 2010, Photobiology of vitamin D, 35 Jasinghe, 2006, Ultraviolet irradiation: the generator of vitamin D2 in edible mushrooms, Food Chem., 95, 638, 10.1016/j.foodchem.2005.01.046 Roberts, 2008, Vitamin D2 formation from post-harvest UV-B treatment of mushrooms (Agaricus bisporus) and retention during storage, J. Agric. Food Chem., 56, 4541, 10.1021/jf0732511 Teichmann, 2007, Sterol and vitamin D2 concentrations in cultivated and wild grown mushrooms: effect of UV radiation, LWT-Food Sci. Technol., 40, 815, 10.1016/j.lwt.2006.04.003 Koyyalamudi, 2009, Vitamin D2 formation and bioavailability from Agaricus bisporus button mushrooms treated with ultraviolet irradiation, J. Agric. Food Chem., 57, 3351, 10.1021/jf803908q Koyyalamudi, 2011, Concentration of vitamin D2 in white button mushrooms (Agaricus bisporus) exposed to pulsed UV light, J. Food Comp. Anal., 24, 976, 10.1016/j.jfca.2011.02.007 Phillips, 2011, Vitamin D and sterol composition of 10 types of mushrooms from retail suppliers in the United States, J. Agric. Food Chem., 59, 7841, 10.1021/jf104246z Urbain, 2016, Impact on vitamin D2, vitamin D4 and agaritine in Agaricus bisporus mushrooms after artificial and natural solar UV light exposure, Plant Foods Hum. Nutr., 71, 314, 10.1007/s11130-016-0562-5 Sohsomboon, 2018, Unique antimicrobial spectrum of ophiobolin K produced by Aspergillus ustus, Biosci. Biotechnol. Biochem., 82, 422, 10.1080/09168451.2018.1429890 Lee, 2016, Paraptosis in the anti-cancer arsenal of natural products, Pharmacol. Ther., 162, 120, 10.1016/j.pharmthera.2016.01.003 Au, 2000, The biology of ophiobolins, Life Sci., 67, 733, 10.1016/S0024-3205(00)00668-8 Bencsik, 2014, Ophiobolin A from Bipolaris oryzae perturbs motility and membrane integrities of porcine sperm and induces cell death on mammalian somatic cell lines, Toxins (Basel), 6, 2857, 10.3390/toxins6092857 Hesseltine, 1971, Helminthosporium secondary metabolites, southern leaf blight of corn, and biology, J. Agric. Food Chem., 19, 707, 10.1021/jf60176a020 Nozoe, 1965, The structure of ophiobolin, a C25 terpenoid having a novel skeleton, J. Am. Chem. Soc., 87, 4968, 10.1021/ja00949a061 Sadler, 1989, The determination by NMR methods of the structure and stereochemistry of astellatol, a new and unusual sesterterpene, J. Chem. Soc., Chem. Commun., 8, 1602, 10.1039/c39890001602 Kawahara, 1999, A novel sesterterpenoid, nitiol, as a potent enhancer of IL-2 gene expression in a human T Cell line, from the Peruvian folk medicine “Hercumpuri” (Gentianella nitida), Chem. Pharm. Bull., 47, 1344, 10.1248/cpb.47.1344 Hog, 2015, Evolution of a unified strategy for complex sesterterpenoids: progress toward astellatol and total synthesis of (−)-nitidasin, Chemistry, 21, 13646, 10.1002/chem.201501423 Matsuda, 2014, Complete biosynthetic pathway of anditomin: nature's sophisticated synthetic route to a complex fungal meroterpenoid, J. Am. Chem. Soc., 136, 15326, 10.1021/ja508127q Qiao, 2018, Aspermerodione, a novel fungal metabolite with an unusual 2,6-dioxabicyclo[2.2.1]heptane skeleton, as an inhibitor of penicillin-binding protein 2a, Sci. Rep., 8, 5454, 10.1038/s41598-018-23817-1 He, 2017, a bridged spirocyclic meroterpenoid, as a potent potentiator of oxacillin against methicillin-resistant Staphylococcus aureus from Aspergillus sp. TJ23, J. Org. Chem., 82, 3125, 10.1021/acs.joc.7b00056 Cho, 2003, Terreulactones A, B, C, and D: novel acetylcholinesterase inhibitors produced by Aspergillus terreus. I. Taxonomy, fermentation, isolation and biological activities, J. Antibiot., 56, 344, 10.7164/antibiotics.56.344 Macías, 2000, Novel bioactive breviane spiroditerpenoids from Penicillium brevicompactum Dierckx, J. Org. Chem., 65, 9039, 10.1021/jo0011078 Costa, 2013, New 9,10-secosteroids from biotransformations of hyodeoxycholic acid with Rhodococcus spp, Helv. Chim. Acta, 96, 1062, 10.1002/hlca.201200330 Chen, 2014, Three novel degraded steroids from cultures of the Basidiomycete Antrodiella albocinnamomea, Steroids, 87, 21, 10.1016/j.steroids.2014.05.008 Wu, 2000, Two novel secoergosterols from the fungus Tylopilus plumbeoviolaceus, J. Nat. Prod., 63, 534, 10.1021/np990494h Xiao, 2013, Asperterpenols A and B, new sesterterpenoids isolated from a mangrove endophytic fungus Aspergillus sp. 085242, Org. Lett., 15, 2522, 10.1021/ol401005j Wainwright, 2017, Fungi associated with mesophotic macroalgae from the 'Au'au Channel, west Maui are differentiated by host and overlap terrestrial communities, Peer J., 5, e3532, 10.7717/peerj.3532 Rozas, 2011, Isolation and cultivation of fungal strains from in vitro cell cultures of two marine sponges (Porifera: Halichondrida and Haplosclerida), Braz. J. Microbiol., 42, 1560, 10.1590/S1517-83822011000400043 Hasan, 2015, Major bioactive metabolites from marine fungi: a review, Bioinformation, 11, 176, 10.6026/97320630011176 Jin, 2016, Potential pharmacological resources: natural bioactive compounds from marine-derived fungi, Mar. Drugs, 14, 10.3390/md14040076 Zhou, 2014, Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp, Tetrahedron Lett., 55, 2789, 10.1016/j.tetlet.2014.02.062 Zhou, 2011, New austalides from the sponge-associated fungus Aspergillus sp, Eur. J. Org. Chem., 30, 6009, 10.1002/ejoc.201100670 Nong, 2014, Territrem and butyrolactone derivatives from a marine-derived fungus Aspergillus terreus, Mar. Drugs, 12, 6113, 10.3390/md12126113 Kumla, 2017, A new dihydrochromone dimer and other secondary metabolites from cultures of the marine sponge-associated fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213, Mar. Drugs, 15, 375, 10.3390/md15120375 Cui, 2010, 7-Nor-ergosterolide, a pentalactone-containing norsteroid and related steroids from the marine-derived endophytic Aspergillus ochraceus EN-31, J. Nat. Prod., 73, 1780, 10.1021/np100386q H. Onodera, M. Ichimura, K. Baba, T. Agatsuma, S. Sasho, M. Suzuki, S. Iwamoto, S. Kakita, PCT Int Appl 2009; WO 2009096445, A1 20090806, CAN 151: 239605, AN 2009: 944135. Liu, 2016, Chermesins A-D: meroterpenoids with a drimane-type spirosesquiterpene skeleton from the marine algal-derived endophytic fungus Penicillium chermesinum EN-480, J. Nat. Prod., 79, 806, 10.1021/acs.jnatprod.5b00893 Kim, 2016, Stachybotrysin an osteoclast differentiation inhibitor from the marine-derived fungus Stachybotrys sp. KCB13F013, J. Nat. Prod., 79, 2703, 10.1021/acs.jnatprod.6b00641 Li, 2012, A sterol and spiroditerpenoids from a Penicillium sp. isolated from a deep sea sediment sample, Mar. Drugs, 10, 497, 10.3390/md10020497 Li, 2014, Meroterpenes from an algicolous strain of Penicillium echinulatum, Magn. Reson. Chem., 52, 247, 10.1002/mrc.4049 Fukuda, 2014, Terretonin G, a new sesterterpenoid antibiotic from marine-derived Aspergillus sp. OPMF00272, J. Antibiot., 67, 593, 10.1038/ja.2014.46 Trisuwan, 2011, Sesquiterpene and xanthone derivatives from the sea fan-derived fungus Aspergillus sydowii PSU-F154, J. Nat. Prod., 74, 1663, 10.1021/np200374j Kong, 2017, Chrodrimanins K-N and related meroterpenoids from the fungus Penicillium sp. SCS-KFD09 isolated from a marine worm, Sipunculus nudus, J. Nat. Prod., 80, 1039, 10.1021/acs.jnatprod.6b01061 Gomes, 2014, Antibacterial and antibiofilm activities of tryptoquivalines and meroditerpenes isolated from the marine-derived fungi Neosartorya paulistensis, N. laciniosa, N. tsunodae, and the soil fungi N. fischeri and N. siamensis, Mar. Drugs, 12, 822, 10.3390/md12020822 Shi, 2017, Sesteralterin and tricycloalterfurenes A-D: terpenes with rarely occurring frameworks from the marine-alga-epiphytic fungus Alternaria alternata k21–1, J. Nat. Prod., 80, 2524, 10.1021/acs.jnatprod.7b00478 Fang, 2012, Purpurogemutantin and purpurogemutantidin, new drimenyl cyclohexenone derivatives produced by a mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59, Mar. Drugs, 10, 1266, 10.3390/md10061266