Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7

References

• Ayer WA, Altena IV, Browne LM. 1990. Three piperazinediones and a drimane diterpenoid from Penicillium brevi-compactum. Phytochemistry. 29:1661–1665.10.1016/0031-9422(90)80141-3
   Web of Science ®Google Scholar
• Blunt JW, Copp BR, Keyzers RA, Munro MHG, Prinsep MR. 2015. Marine natural products. Nat Prod Rep. 32:116–211.10.1039/C4NP00144C
   PubMed Web of Science ®Google Scholar
• Bugni TS, Abbanat D, Bernan VS, Maiese WM, Greenstein M, Van Wagoner RM, Ireland CM. 2000. yanuthones: novel metabolites from a marine isolate of Aspergillus niger. J Org Chem. 65:7195–7200.10.1021/jo0006831
   PubMed Web of Science ®Google Scholar
• Chung W, Goo YM, Na DS, Kim kJ. 1995. A phospholipase A2 inhibitor from Arisaema amurense max. var. serratum Nakai. Arch Pharm Res. 18:293–294.10.1007/BF02976416
   Web of Science ®Google Scholar
• Fang SM, Cui CB, Li CW, Wu CJ, Zhang ZJ, Li L, Huang XJ, Ye WC. 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. 10:1266–1287.10.3390/md10061266
   PubMed Web of Science ®Google Scholar
• Fu Y, Wu P, Xue JH, Li HX, Wei XY. 2015. Myrothecols g and h, two new analogues of the marine-derived quinone sesquiterpene Penicilliumin A. Mar Drugs. 13:3360–3367.10.3390/md13063360
   PubMed Web of Science ®Google Scholar
• Fujimoto H, Nakamura E, Kim Y, Okuyama E, Ishibashi M, Sassa T. 2001. Immunomodulatory constituents from an ascomycete, Eupenicillium crustaceum , and revised absolute structure of macrophorin D. J Nat Prod. 64:1234–1237.10.1021/np010152n
   PubMed Web of Science ®Google Scholar
• Geiseler O, Podlech J. 2012. Total synthesis of infectopyrone, aplysiopsenes A–C, ent-aplysiopsene D, phomapyrones A and D, 8,9-dehydroxylarone, and nectriapyrone. Tetrahedron. 68:7280–7287.10.1016/j.tet.2012.06.104
   Web of Science ®Google Scholar
• Geris R, Simpson TJ. 2009. Meroterpenoids produced by fungi. Nat Prod Rep. 26:1063–1094.10.1039/b820413f
   PubMed Web of Science ®Google Scholar
• Göhl M, Seifert K. 2014. Synthesis of the sesquiterpenes albicanol, drimanol, and drimanic acid, and the marine sesquiterpene hydroquinone deoxyspongiaquinol. Eur J Org Chem. 2014:6975–6982.10.1002/ejoc.201402873
   Web of Science ®Google Scholar
• Huh S, Kim Y, Jung E, Lim J, Jung KS, Kim M, Lee J, Park D. 2010. Melanogenesis inhibitory effect of fatty acid alkyl esters isolated from oxalis triangularis. Biol Pharm Bull. 33:1242–1245.10.1248/bpb.33.1242
   PubMed Web of Science ®Google Scholar
• Igarashi Y, Sekine A, Fukazawa H, Uehara Y, yamaguchI K, Endo Y, Okuda T, Furumai T, Oki T. 2002. Anicequol, a novel inhibitor for anchorage-independent growth of tumor cells from penicillium aurantiogriseum dierckx TP-F0213. J Antibiot. 55:371–376.10.7164/antibiotics.55.371
   PubMed Web of Science ®Google Scholar
• Ishikawa K, Hosoe T, Itabashi T, Wakana D, Takizawa K, Yaguchi T, Kawai K. 2010. Novoamauromine and ent-cycloechinulin: two new diketopiperazine derivatives from Aspergillus novofumigatus. Chem Pharm Bull. 58:717–719.10.1248/cpb.58.717
   PubMed Web of Science ®Google Scholar
• Li XF, Choi HD, Kang JS, Lee C, Son BW. 2003. Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7.
   Google Scholar
• Marcos IS, Conde A, Moro RF, Basabe P, Díez D, Urones JG. 2010a. Quinone/hydroquinone sesquiterpenes. Mini-Rev Org Chem. 7:230–254.10.2174/157019310791384128
   Web of Science ®Google Scholar
• Marcos IS, Conde A, Moro RF, Basabe P, Díez D, Urones JG. 2010b. Synthesis of quinone/hydroquinone sesquiterpenes. Tetrahedron. 66:8280–8290.10.1016/j.tet.2010.08.038
   Web of Science ®Google Scholar
• Mehta G, Pan SC. 2005. First total synthesis of yanuthones: novel farnesylated epoxycyclohexenoid marine natural products. Tetrahedron Lett. 46:5219–5223.10.1016/j.tetlet.2005.05.118
   Web of Science ®Google Scholar
• Morens DM, Folkers GK, Fauci AS. 2004. The challenge of emerging and re-emerging infectious diseases. Nature. 430:242–249.10.1038/nature02759
   PubMed Web of Science ®Google Scholar
• Poling SM, Wicklow DT, Rogers KD, Gloer JB. 2008. Acremonium zeae, a protective endophyte of maize, produces dihydroresorcylide and 7-hydroxydihydroresorcylides. J Agric Food Chem. 56:3006–3009.10.1021/jf073274f
   PubMed Web of Science ®Google Scholar
• Rateb ME, Ebel R. 2011. Secondary metabolites of fungi from marine habitats. Nat Prod Rep. 28:290–344.10.1039/c0np00061b
   PubMed Web of Science ®Google Scholar
• Serra S, Cominetti AA, Lissoni V. 2014. A general synthetic approach to hydroquinone meroterpenoids: stereoselective synthesis of (+)-(S)-metachromin V and alliodorol. Nat Prod Commun. 9:303–308.
   PubMed Web of Science ®Google Scholar
• Sunassee SN, Davies-Coleman MT. 2012. Cytotoxic and antioxidant marine prenylated quinones and hydroquinones. Nat Prod Rep. 29:513–535.10.1039/c2np00086e
   PubMed Web of Science ®Google Scholar
• Thao TTP, Anh NV, Anh HN, Quan TD. 2009. Study on chemical constituents of the vietnamese medicinal plant Fissistigma petelotii. Z Naturforsch 64b:323–327.
   Google Scholar
• Trimble LA, Sumarah MW, Blackwell BA, Wrona MD, Miller JD. 2012. Characterization of (16R) and (16S)-hydroxyroquefortine C: diastereomeric metabolites from Penicillium crustosum DAOM 215343. Tetrahedron Lett. 53:956–958.10.1016/j.tetlet.2011.12.052
   Web of Science ®Google Scholar
• Wang Q, Song FH, Xiao X, Huang P, Li L, Monte A, Abdel-Mageed WM, Wang J, Guo H, He W, et al. 2013. Abyssomicins from the South China Sea deep-sea sediment Verrucosispora sp.: natural thioether michael addition adducts as antitubercular prodrugs. Angew Chem Int Ed. 52:1231–1234.10.1002/anie.201208801
   PubMed Web of Science ®Google Scholar
• Wang JF, Wei XY, Lu X, Xu FQ, Wan JT, Lin XP, Zhou XF, Liao SR, Yang B, Tu ZC, Liu YH. 2014. Eight new polyketide metabolites from the fungus Pestalotiopsis vaccinii endogenous with the mangrove plant Kandelia candel (L.) Druce. Tetrahedron. 70:9695–9701.10.1016/j.tet.2014.10.056
   Web of Science ®Google Scholar
• Wang JF, Wei XY, Qin XC, Lin XP, Zhou XF, Liao SR, Yang B, Liu J, Tu ZC, Liu YH. 2015. Arthpyrones A–C, pyridone alkaloids from a sponge-derived fungus Arthrinium arundinis ZSDS1-F3. Org Lett. 17:656–659.10.1021/ol503646c
   PubMed Web of Science ®Google Scholar
• Wang JF, Wei XY, Qin XC, Tian XP, Liao L, Li KM, Zhou XF, Yang XW, Wang FZ, Zhang TY, et al. 2016. Antiviral merosesquiterpenoids produced by an Antarctic fungus Aspergillus ochraceopetaliformis SCSIO 05702. J Nat Prod. 79:59–65.10.1021/acs.jnatprod.5b00650
   PubMed Web of Science ®Google Scholar
• Wang JF, Xu FQ, Wang Z, Lu X, Wan JT, Yang B, Zhou XF, Zhang TY, Tu ZC, Liu YH. 2014. A new naphthalene glycoside from the sponge-derived fungus Arthrinium sp. ZSDS1-F3. Nat Prod Res. 28:1070–1074.10.1080/14786419.2014.905935
   PubMed Web of Science ®Google Scholar