Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities
Abstract
Four new alkaloids, including two new meleagrin analogs, meleagrin D (1) and E (2), and two new diketopiperazines, roquefortine H (3) and I (4), were isolated from a deep ocean sediment-derived fungus Penicillium sp. Meleagrin D (1) and E (2) possess unprecedented acetate-mevalonate-derived side chains on the imidazole moiety. These new meleagrins showed weak cytotoxicity against the A-549 cell line, whereas meleagrin B (5) and meleagrin (6), which were isolated previously from the same strain, induced HL-60 cell apoptosis or arrested the cell cycle through G(2)/M phase, respectively. The results indicate that the distinct substitutions on the imidazole ring significantly influence the cytotoxicity of the meleagrin alkaloids.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Cites
Mosmann, T. (1983) · Journal of Immunological Methods · doi:10.1016/0022-1759(83)90303-4 · Cited by 56,104 · see citing works
New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening
Skehan, P., Storeng, R., Scudiero, D. A., Monks, A. P., McMahon, J., Vistica, D. T., Warren, J. T., Bokesch, H. R., Kenney, S., & Boyd, M. R. (1990) · JNCI Journal of the National Cancer Institute · doi:10.1093/jnci/82.13.1107 · Cited by 9,801 · see citing works
New alkaloids and diterpenes from a deep ocean sediment derived fungus Penicillium sp.
Du, L., Li, D., Zhu, T., et al. (2008) · Tetrahedron · doi:10.1016/j.tet.2008.11.078 · Cited by 172 · see citing works
Self-citationBiosynthesis of Prenylated Alkaloids Derived from Tryptophan
Williams, R. M., Stocking, E. M., & Sanz‐Cervera, J. F. (2000) · Topics in current chemistry · doi:10.1007/3-540-48146-x_3 · Cited by 169 · see citing works
Roquefortine and isofumigaclavine A, metabolites fromPenicillium roqueforti
Scott, P. M., Merrien, M.-A., & Polonsky, J. (1976) · Cellular and Molecular Life Sciences · doi:10.1007/bf01937728 · Cited by 135 · see citing works
Koizumi, Y., Arai, M., Tomoda, H., & Ōmura, S. (2004) · Biochimica et Biophysica Acta (BBA) - Molecular Cell Research · doi:10.1016/j.bbamcr.2004.04.013 · Cited by 75 · see citing works
Roquefortine, an intermediate in the biosynthesis of oxaline in cultures of Penicillium oxalicum
Steyn, P. S., & Vleggaar, R. (1983) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39830000560 · Cited by 46 · see citing works
Cytotoxic Sorbicillinoids and Bisorbicillinoids from a Marine-Derived Fungus Trichoderma sp.
Du, L., Zhu, T., Li, L., et al. (2009) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.57.220 · Cited by 45 · see citing works
Self-citationMolecular Requirements for Inhibition of Cytochrome P450 Activities by Roquefortine
Aninat, C., Hayashi, Y., André, F., et al. (2001) · Chemical Research in Toxicology · doi:10.1021/tx015512l · Cited by 43 · see citing works
Roquefortine E, a Diketopiperazine from an Australian Isolate of Gymnoascus r eessii
Clark, B. R., Capon, R. J., Lacey, E., et al. (2005) · Journal of Natural Products · doi:10.1021/np0503101 · Cited by 41 · see citing works
Studies on fungal products. VII. The structures of meleagrin and 9-O-p-bromobenzoylmeleagrin.
Kawai, K., Nozawa, K., Nakajima, S., et al. (1984) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.32.94 · Cited by 41 · see citing works
Antimicrobial action of roquefortine
Kopp, B., & Rehm, H. J. (1979) · Applied Microbiology and Biotechnology · doi:10.1007/bf00499170 · Cited by 38 · see citing works
Isolation of a new indole alkaloid, roquefortine D, from the cultures of Penicillium roqueforti.
Ohmomo, S., Oguma, K., Ōhashi, T., et al. (1978) · Agricultural and Biological Chemistry · doi:10.1271/bbb1961.42.2387 · Cited by 25 · see citing works
Musuku, A., Selala, M. I., Bruyne, T. D., et al. (1994) · Journal of Natural Products · doi:10.1021/np50109a017 · Cited by 21 · see citing works
Kusch, J., & Rehm, H. J. (1986) · Applied Microbiology and Biotechnology · doi:10.1007/bf00257040 · Cited by 10 · see citing works
A New 16N-Carboxyethyl Derivative of 3,12-Dihydroroquefortin
Gollmick, F. A., Kozlovsky, A. G., Zhelifonova, V. P., et al. (2003) · Heterocycles · doi:10.3987/com-03-9776 · Cited by 7 · see citing works
Absolute configuration of roquefortine C, a tremorgenic mycotoxin
Yamaguchi, T. F., Nozawa, K., Nakajima, S., et al. (1991) · JSM Mycotoxins · doi:10.2520/myco1975.1991.34_29 · Cited by 6 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Marine Natural Products: A Source of Novel Anticancer Drugs
Khalifa, S. A. M., Elias, N., Farag, M. A., Chen, L., Saeed, A., Hegazy, M.-E. F., Moustafa, M. S., Abd El-Wahed, A., Al-Mousawi, S. M., Musharraf, S. G., et al. (2019) · Marine Drugs · doi:10.3390/md17090491 · Cited by 555 · see citing works
Immense essence of excellence: Marine microbial bioactive compounds
Bhatnagar, I., & Kim, S.-K. (2010) · Marine Drugs · doi:10.3390/md8102673 · Cited by 384 · see citing works
- Authors
- Du, L., Feng, T., Zhao, B., Li, D., Cai, S., Zhu, T., Wang, F., Xiao, X., & Gu, Q.
- Affiliations
- Ocean University of China (CN)
- Shanghai Jiao Tong University (CN)
- Corresponding author
- Gu, Qianqun
- Venue
- The Journal of Antibiotics
- Published
- 2010-02-26
- Volume
- 63
- Issue
- 4
- Pages
- 165-170
- ISSN
- 0021-8820 (ISSN-L)
- 1881-1469
- OpenAlex
- W2059449263
- Cited by
- 106
- References
- 17
- Citations by year
- 2026: 5 · 2025: 4 · 2024: 8 · 2023: 5 · 2022: 10 · 2021: 6 · 2020: 8 · 2019: 5 · 2018: 3 · 2017: 5 · 2016: 8 · 2015: 12 · 2014: 6 · 2013: 5 · 2012: 8
- FWCI
- 4.69
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- www.springer.com/tdm (tdm)
- Locations
- The Journal of Antibiotics (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Marine Sponges and Natural Products
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Microbial Metabolism and Applications
- Keywords
- diketopiperazines, Penicillium, fungal alkaloids, cytotoxicity, apoptosis, G2/M cell cycle arrest, HL-60 cells, A549 cells, anticancer activity
- MeSH terms
- Alkaloids, Antineoplastic Agents, Cell Cycle, Cell Survival, Diterpenes, Drug Screening Assays, Antitumor, Flow Cytometry, Humans, Imidazoles, Penicillium, Soil Microbiology, Spectrophotometry, Infrared, Spectrophotometry, Ultraviolet, Apoptosis, HL-60 Cells, Geologic Sediments, Nuclear Magnetic Resonance, Biomolecular, Spectrometry, Mass, Electrospray Ionization
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
