New Furan and Cyclopentenone Derivatives from the Sponge-Associated Fungus Hypocrea Koningii PF04
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation
Position | 1 | 2 | 3 | 4 | 5 |
---|---|---|---|---|---|
1 | 5.89, s | ||||
2 | 3.67, m | 6.99, d (8.5) | 5.91, t (1.6) | 5.87, s | 6.46, s |
3 | 3.70, m | 6.82, d (8.5) | |||
4 | 2.56, m | 2.53, m | 2.76, m | ||
5 | 6.42, d (3.2) | 6.82, d (8.5) | 2.39, m | 2.27, m | 2.41, m |
6 | 6.24, d (3.1) | 6.99, d (8.5) | 2.69, t (7.3) | 2.61, m | 7.61, d (15.9) |
7 | 2.60, t (7.3) | 2.61, m | 6.40, d (15.9) | ||
8 | 4.37, d (5.4) | 7.40, s | |||
9 | 1.22, d (5.8) | 4.33, t (7.0) | 4.17, t (6.9) | ||
10 | 1.27, d (5.8) | 6.19, d (3.5) | 2.95, t (7.0) | 2.76, t (6.9) | |
11 | 6.37, d (3.5) | ||||
12 | 7.21, d (7.0) | 7.02, d (8.4) | |||
13 | 4.36, d (4.9) | 7.31, t (7.5) | 6.68, d (8.4) | ||
14 | 9.63, s | 7.24, t (7.5) | |||
15 | 7.31, t (7.5) | 6.68, d (8.4) | |||
16 | 7.21, d (7.0) | 7.02, d (8.4) | |||
4-OH | 9.61, s | ||||
8-OH | 5.23, t (5.8) | 12.8, s | |||
13-OH | 5.34, t (5.7) | ||||
14-OH | 9.24, s |
Carbon | 1 | 2 | 3 | 4 | 5 |
---|---|---|---|---|---|
1 | 95.8, CH | 123.5, qC | 209.6, qC | 208.7, qC | 208.7, qC |
2 | 79.2, CH | 130.3, CH | 129.4, CH | 128.4, CH | 135.1, CH |
3 | 77.5, CH | 115.3, CH | 180.3, qC | 181.6, qC | 169.3, qC |
4 | 150.7, qC | 157.4, qC | 31.6, CH2 | 31.0, CH2 | 26.6, CH2 |
5 | 109.4, CH | 115.3, CH | 35.2, CH2 | 34.9, CH2 | 34.7, CH2 |
6 | 107.3, CH | 130.3, CH | 28.4, CH2 | 28.0, CH2 | 137.9, CH |
7 | 155.9, qC | 137.7, qC | 31.5, CH2 | 30.9, CH2 | 126.4, CH |
8 | 55.6, CH2 | 136.0, CH | 172.0, qC | 171.9, qC | 166.7, qC |
9 | 16.4, CH3 | 149.6, qC | 65.2, CH2 | 64.9, CH2 | |
10 | 16.5, CH3 | 117.0, CH | 35.0, CH2 | 33.5, CH2 | |
11 | 110.1, CH | 137.5, qC | 127.8, qC | ||
12 | 159.0, qC | 128.8, CH | 129.7, CH | ||
13 | 55.8, CH2 | 128.5, CH | 115.1, CH | ||
14 | 193.4, CH | 126.7, CH | 155.9, qC | ||
15 | 128.5, CH | 115.1, CH | |||
16 | 128.8, CH | 129.7, CH |
2.2. Plausible Biosynthetic Pathways
2.3. Biological Activity
Compound | IC50 | Compound | IC50 |
---|---|---|---|
1 | 27.4 ± 7.4 | 8 | >128 |
2 | >128 | 9 | >128 |
3 | >128 | 10 | 16.8 ± 4.3 |
4 | >128 | 11 | 61.7 ± 3.3 |
5 | >128 | 12 | >128 |
6 | >128 | Ascorbic acid | 4.4 ± 0.4 |
7 | >128 |
3. Experimental Section
3.1. General Experimental Procedures
3.2. Fungal Material
3.3. Fermentation
3.4. Extraction and Isolation
3.5. Antibacterial Activity Assay
3.6. DPPH Radical Scavenging Activity Assay
3.7. Theoretical ECD Calculations
4. Conclusions
Supplementary Files
Supplementary File 1Acknowledgments
Author Contributions
Conflicts of Interest
References
- Saleem, M.; Ali, M.S.; Hussain, S.; Jabbar, A.; Ashraf, M.; Lee, Y.S. Marine natural products of fungal origin. Nat. Prod. Rep. 2007, 24, 1142–1152. [Google Scholar] [CrossRef] [PubMed]
- Blunt, J.W.; Copp, B.R.; Keyzers, R.A.; Munro, M.H.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2014, 31, 160–258. [Google Scholar] [CrossRef] [PubMed]
- Rateb, M.E.; Ebel, R. Secondary metabolites of fungi from marine habitats. Nat. Prod. Rep. 2011, 28, 290–344. [Google Scholar] [CrossRef] [PubMed]
- Debbab, A.; Aly, A.H.; Proksch, P. Bioactive secondary metabolites from endophytes and associated marine derived fungi. Fungal Divers. 2011, 49, 1–12. [Google Scholar] [CrossRef]
- Bugni, T.S.; Ireland, C.M. Marine-derived fungi: A chemically and biologically diverse group of microorganisms. Nat. Prod. Rep. 2004, 21, 143–163. [Google Scholar] [CrossRef] [PubMed]
- Martins, A.; Vieira, H.; Gaspar, H.; Santos, S. Marketed marine natural products in the pharmaceutical and cosmeceutical industries: Tips for success. Mar. Drugs 2014, 12, 1066–1101. [Google Scholar] [CrossRef] [PubMed]
- Hentschel, U.; Piel, J.; Degnan, S.M.; Taylor, M.W. Genomic insights into the marine sponge microbiome. Nat. Rev. Microbiol. 2012, 10, 641–654. [Google Scholar] [CrossRef] [PubMed]
- Ding, B.; Yin, Y.; Zhang, F.; Li, Z. Recovery and phylogenetic diversity of culturable fungi associated with marine sponges Clathrina luteoculcitella and Holoxea sp. in the South China Sea. Mar. Biotechnol. 2011, 13, 713–721. [Google Scholar] [CrossRef] [PubMed]
- Kopchinskiy, A.; Komon, M.; Kubicek, C.P.; Druzhinina, I.S. TrichoBLAST: A multilocus database for Trichoderma and Hypocrea identifications. Mycol. Res. 2005, 109, 658–660. [Google Scholar] [CrossRef] [PubMed]
- Harman, G.E.; Howell, C.R.; Viterbo, A.; Chet, I.; Lorito, M. Trichoderma species-opportunistic, avirulent plant symbionts. Nat. Rev. Microbiol. 2004, 2, 43–56. [Google Scholar] [CrossRef] [PubMed]
- Miao, F.-P.; Liang, X.-R.; Yin, X.-L.; Wang, G.; Ji, N.-Y. Absolute configurations of unique harziane diterpenes from Trichoderma species. Org. Lett. 2012, 14, 3815–3817. [Google Scholar] [CrossRef] [PubMed]
- Berkaew, P.; Soonthornchareonnon, N.; Salasawadee, K.; Chanthaket, R.; Isaka, M. Aurocitrin and related polyketide metabolites from the wood-decay fungus Hypocrea sp. BCC 14122. J. Nat. Prod. 2008, 71, 902–904. [Google Scholar] [CrossRef] [PubMed]
- Ohkawa, Y.; Miki, K.; Suzuki, T.; Nishio, K.; Sugita, T.; Kinoshita, K.; Takahashi, K.; Koyama, K. Antiangiogenic metabolites from a marine-derived fungus, Hypocrea vinosa. J. Nat. Prod. 2010, 73, 579–582. [Google Scholar] [CrossRef] [PubMed]
- Wu, B.; Oesker, V.; Wiese, J.; Schmaljohann, R.; Imhoff, J.F. Two new antibiotic pyridones produced by a marine fungus, Trichoderma sp. Strain MF106. Mar. Drugs 2014, 12, 1208–1219. [Google Scholar] [CrossRef] [PubMed]
- Panizel, I.; Yarden, O.; Ilan, M.; Carmeli, S. Eight new peptaibols from sponge-associated Trichoderma atroviride. Mar. Drugs 2013, 11, 4937–4960. [Google Scholar] [CrossRef] [PubMed]
- Isaka, M.; Chinthanom, P.; Sappan, M.; Chanthaket, R.; Luangsa-ard, J.J.; Prabpai, S.; Kongsaeree, P. Lanostane and hopane triterpenes from the entomopathogenic fungus Hypocrella sp. BCC 14524. J. Nat. Prod. 2011, 74, 2143–2150. [Google Scholar] [CrossRef] [PubMed]
- Shen, Y.-C.; Prakash, C.V.S.; Kuo, Y.-H. Three new furan derivatives and a new fatty acid from a Taiwanese marine sponge Plakortis simplex. J. Nat. Prod. 2001, 64, 324–327. [Google Scholar] [CrossRef] [PubMed]
- Kikuchi, H.; Tsukitani, Y.; Iguchi, K.; Yamada, Y. Clavulones, new type of prostanoids from the stolonifer Clavulariaviridis Quoy and Gaimard. Tetrahedron Lett. 1982, 23, 5171–5174. [Google Scholar] [CrossRef]
- Murray, R.D.H.; Jorge, Z.D.; Khan, N.H.; Shahjahan, M.; Quaisuddin, M. Diosbulbin D and 8-epidiosbulbin E acetate, norclerodane diterpenoids from Dioscorea bulbifera tubers. Phytochemistry 1984, 23, 623–625. [Google Scholar] [CrossRef]
- Sun, K.; Li, Y.; Guo, L.; Wang, Y.; Liu, P.; Zhu, W. Indole diterpenoids and isocoumarin from the fungus, Aspergillus flavus, Isolated from the prawn, Penaeus vannamei. Mar. Drugs 2014, 12, 3970–3981. [Google Scholar] [CrossRef] [PubMed]
- Bringmann, G.; Bruhn, T.; Maksimenka, K.; Hemberger, Y. The assignment of absolute stereostructures through quantum chemical circular dichroism calculations. Eur. J. Org. Chem. 2009, 2009, 2717–2727. [Google Scholar] [CrossRef]
- Sun, S.; Tian, L.; Wang, Y.; Wu, H.; Lu, X.; Pei, Y. A novel natural product from the fermentation liquid of marine fungus Trichoderma atroviride G20–12. Asian J. Trad. Med. 2009, 4, 123–127. [Google Scholar]
- Amagata, T.; Usami, Y.; Minoura, K.; Ito, T.; Numata, A. Cytotoxic substances produced by a fungal strain from a sponge: Physico-chemical properties and structures. J. Antibiot. 1998, 51, 33–40. [Google Scholar] [CrossRef] [PubMed]
- Gautschi, J.T.; Tenney, K.; Compton, J.; Crews, P. Chemical investigations of a deep water marine-derived fungus: Simple amino acid derivatives from an Arthrinium sp. Nat. Prod. Commun. 2007, 2, 541–546. [Google Scholar]
- Chen, Q.; Yang, L.; Zhang, G.; Wang, F. Bioactivity-guided isolation of antiosteoporotic compounds from Ligustrum lucidum. Phytother. Res. 2013, 27, 973–979. [Google Scholar] [CrossRef] [PubMed]
- Gernigon, N.; Al-Zoubi, R.M.; Hall, D.G. Direct amidation of carboxylic acids catalyzed by ortho-iodo arylboronic acids: Catalyst optimization, scope, and preliminary mechanistic study supporting a peculiar halogen acceleration effect. J. Org. Chem. 2012, 77, 8386–8400. [Google Scholar] [CrossRef] [PubMed]
- Kang, B.; Fu, Z.; Hong, S.H. Ruthenium-catalyzed redox-neutral and single-step amide synthesis from alcohol and nitrile with complete atom economy. J. Am. Chem. Soc. 2013, 135, 11704–11707. [Google Scholar] [CrossRef] [PubMed]
- Tarawneh, A.H.; León, F.; Radwan, M.M.; Rosa, L.H.; Cutler, S.J. Secondary metabolites from the fungus Emericella nidulans. Nat. Prod. Commun. 2013, 8, 1285–1288. [Google Scholar] [PubMed]
- Ulbricht, R.J.; Northup, S.J.; Thomas, J.A. A review of 5-hydroxymethylfurfural (HMF) in parenteral solutions. Toxicol. Sci. 1984, 4, 843–853. [Google Scholar] [CrossRef]
- Celińska, E.; Grajek, W. Biotechnological production of 2,3-butanediol-current state and prospects. Biotechnol. Adv. 2009, 27, 715–725. [Google Scholar] [CrossRef] [PubMed]
- Ferretti, A.; Flanagan, V.P. Volatile constituents of whey powder subjected to accelerated browning. J. Dairy Sci. 1971, 54, 1764–1768. [Google Scholar] [CrossRef]
- Kaminaga, Y.; Schnepp, J.; Peel, G.; Kish, C.M.; Ben-Nissan, G.; Weiss, D.; Orlova, I.; Lavie, O.; Rhodes, D.; Wood, K. Plant phenylacetaldehyde synthase is a bifunctional homotetrameric enzyme that catalyzes phenylalanine decarboxylation and oxidation. J. Biol. Chem. 2006, 281, 23357–23366. [Google Scholar] [CrossRef] [PubMed]
- Correa, H.; Aristizabal, F.; Duque, C.; Kerr, R. Cytotoxic and antimicrobial activity of pseudopterosins and seco-pseudopterosins isolated from the octocoral Pseudopterogorgia elisabethae of San Andres and Providencia Islands (Southwest Caribbean Sea). Mar. Drugs 2011, 9, 334–344. [Google Scholar] [CrossRef] [PubMed]
- Ma, K.; Bao, L.; Han, J.; Jin, T.; Yang, X.; Zhao, F.; Li, S.; Song, F.; Liu, M.; Liu, H. New benzoate derivatives and hirsutane type sesquiterpenoids with antimicrobial activity and cytotoxicity from the solid-state fermented rice by the medicinal mushroom Stereum hirsutum. Food Chem. 2014, 143, 239–245. [Google Scholar] [CrossRef] [PubMed]
© 2015 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Ding, L.-J.; Gu, B.-B.; Jiao, W.-H.; Yuan, W.; Li, Y.-X.; Tang, W.-Z.; Yu, H.-B.; Liao, X.-J.; Han, B.-N.; Li, Z.-Y.; et al. New Furan and Cyclopentenone Derivatives from the Sponge-Associated Fungus Hypocrea Koningii PF04. Mar. Drugs 2015, 13, 5579-5592. https://doi.org/10.3390/md13095579
Ding L-J, Gu B-B, Jiao W-H, Yuan W, Li Y-X, Tang W-Z, Yu H-B, Liao X-J, Han B-N, Li Z-Y, et al. New Furan and Cyclopentenone Derivatives from the Sponge-Associated Fungus Hypocrea Koningii PF04. Marine Drugs. 2015; 13(9):5579-5592. https://doi.org/10.3390/md13095579
Chicago/Turabian StyleDing, Li-Jian, Bin-Bin Gu, Wei-Hua Jiao, Wei Yuan, Ying-Xin Li, Wei-Zhuo Tang, Hao-Bing Yu, Xiao-Jian Liao, Bing-Nan Han, Zhi-Yong Li, and et al. 2015. "New Furan and Cyclopentenone Derivatives from the Sponge-Associated Fungus Hypocrea Koningii PF04" Marine Drugs 13, no. 9: 5579-5592. https://doi.org/10.3390/md13095579