Absolute Configuration of New Cytotoxic and Other Bioactive Trichothecene Macrolides
Abstract
Three new cytotoxic 10,13-cyclotrichothecane-derived macrolides, myrothecines A-C (1-3), were characterized from the extracts of two Myrothecium roridum strains, IFB-E009 and IFB-E012, isolated as endophytic fungi found on the traditional Chinese medicinal plants Trachelospermum jasminoides and Artemisia annua, respectively. The absolute configuration of myrothecines A-C was elucidated by a combination of spectral techniques (UV, IR, MS, circular dichroism (CD), (1)H and (13)C NMR, DEPT, (1)H-(1)H COSY, NOESY, HMQC, and HMBC spectrascopic analyses), Mosher's ester analysis, and single-crystal X-ray diffraction. The absolute configuration of the reported bioactive analogue, mytoxin B was established by correlating its spectral data with that of known absolute configurational structures. Furthermore, the significance in endophytism (or symbiosis) and biocatabolism, highlighted by production of those macrolides by the endophytic strains, is discussed in brief.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Only one strain of endophytic fungus from A. annua is so far reported as a potential source of artemisinin.
“only one strain is so far reported as a potential source of artemisinin [358].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [358]
Cites
High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids
Ohtani, I. I., Kusumi, T., Kashman, Y., & Kakisawa, H. (1991) · Journal of the American Chemical Society · doi:10.1021/ja00011a006 · Cited by 3,217 · see citing works
White, T. C., Bruns, T. D., Lee, S., Taylor, F. J. R., White, T., Lee, S., Taylor, D. L., & Shawe‐Taylor, J. (1990) · Cited by 2,604 · see citing works
IMMUNOMODULATION BY FUNGAL TOXINS
Pestka, J. J. (2000) · Journal of Toxicology and Environmental Health Part B · doi:10.1080/109374000281113 · Cited by 579 · see citing works
Allosteric Activators of Glucokinase: Potential Role in Diabetes Therapy
Grimsby, J. S., Sarabu, R., Corbett, W. L., Haynes, N.-E., Bizzarro, F. T., Coffey, J. W., Guertin, K. R., Hilliard, D. W., Kester, R. F., Mahaney, P. E., et al. (2003) · Science · doi:10.1126/science.1084073 · Cited by 526 · see citing works
Pestka, J. J., Zhou, H.-R., Moon, Y., & Chung, Y. J. (2004) · Toxicology Letters · doi:10.1016/j.toxlet.2004.04.023 · Cited by 482 · see citing works
Larena, I., Salazar, Ó., García, V. G., Julián, M. C., & Rubio, V. (1999) · Journal of Biotechnology · doi:10.1016/s0168-1656(99)00154-6 · Cited by 276 · see citing works
Trichothecene Production byTrichoderma brevicompactum
Nielsen, K. F., Gräfenhan, T., Zafari, D., et al. (2005) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf051279b · Cited by 139 · see citing works
Tri1 in Fusarium graminearum Encodes a P450 Oxygenase
McCormick, S. P., Harris, L. J., Alexander, N. J., et al. (2004) · Applied and Environmental Microbiology · doi:10.1128/aem.70.4.2044-2051.2004 · Cited by 139 · see citing works
Tan, R. X., Jensen, P. R., Williams, P. G., et al. (2004) · Journal of Natural Products · doi:10.1021/np049920b · Cited by 136 · see citing works
Self-citationAbbas, H. K., Johnson, B. B., Shier, W. T., et al. (2002) · Phytochemistry · doi:10.1016/s0031-9422(01)00464-2 · Cited by 79 · see citing works
Amagata, T., Rath, C. M. B., Rigot, J. F., et al. (2003) · Journal of Medicinal Chemistry · doi:10.1021/jm030090t · Cited by 79 · see citing works
Pinna, G., Costa, E., & Guidotti, A. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0401479101 · Cited by 68 · see citing works
Antimalarial Activity of Macrocyclic Trichothecenes Isolated from the Fungus Myrothecium verrucaria
Isaka, M., Punya, J., Lertwerawat, Y., et al. (1998) · Journal of Natural Products · doi:10.1021/np980323x · Cited by 65 · see citing works
Andolfi, A., Boari, A., Evidente, A., et al. (2005) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf048339i · Cited by 58 · see citing works
Liu, J., Huang, L. L., Ye, Y., et al. (2005) · Journal of Applied Microbiology · doi:10.1111/j.1365-2672.2005.02760.x · Cited by 55 · see citing works
Self-citationGomi, K., Yamamato, H., & Akimitsu, K. (2003) · Plant Molecular Biology · doi:10.1023/b:plan.0000009287.95682.24 · Cited by 42 · see citing works
Matsumoto, M., Minato, H., Tori, K., et al. (1977) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)83435-3 · Cited by 35 · see citing works
Stereochemistry of the Roridins. Diastereomers of Roridin E
Jarvis, B. B., & Wang, S. (1999) · Journal of Natural Products · doi:10.1021/np990272j · Cited by 35 · see citing works
Novel Macrocyclic Trichothecenes from Myrothecium Roridum
Jarvis, B. B., Comezoglu, F. T., Lee, Y., et al. (1986) · Bulletin des Sociétés Chimiques Belges · doi:10.1002/bscb.19860950901 · Cited by 28 · see citing works
Kinser, S., Li, M., Jia, Q., & Pestka, J. J. (2005) · The Journal of Nutritional Biochemistry · doi:10.1016/j.jnutbio.2004.10.003 · Cited by 26 · see citing works
Microbiological transformations 41.
Moussou, P., Archelas, A., & Furstoss, R. (1998) · Journal of Molecular Catalysis B Enzymatic · doi:10.1016/s1381-1177(98)00007-1 · Cited by 24 · see citing works
Hidden stereospecificity in the biosynthesis of divinyl ether fatty acids
Hámberg, M. (2005) · FEBS Journal · doi:10.1111/j.1742-4658.2004.04510.x · Cited by 21 · see citing works
Alvi, K. A., Rabenstein, J., Woodard, J., et al. (2002) · Journal of Natural Products · doi:10.1021/np010449l · Cited by 20 · see citing works
Isolation and structure of new toxins from plants
Habermehl, G. (1989) · Pure and Applied Chemistry · doi:10.1351/pac198961030377 · Cited by 14 · see citing works
Shimada, A., Takeuchi, S., Kusano, M., et al. (2004) · Plant Science · doi:10.1016/j.plantsci.2004.01.009 · Cited by 13 · see citing works
New Members of the Trichothecene Family.
Sugawara, T., Tanaka, A., Nagai, K., et al. (1997) · The Journal of Antibiotics · doi:10.7164/antibiotics.50.778 · Cited by 12 · see citing works
Grove, J. F. (1986) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/p19860000647 · Cited by 11 · see citing works
Fungal trichothecenes which promote callus initiation from the alfalfa cotyledon.
Kobayashi, A., Nakae, Y., Kawasaki, T., et al. (1989) · Agricultural and Biological Chemistry · doi:10.1271/bbb1961.53.585 · Cited by 9 · see citing works
Chung, E.-J., Choi, K., Kim, H. W., et al. (2003) · Biological and Pharmaceutical Bulletin · doi:10.1248/bpb.26.32 · Cited by 7 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao)
Brown, G. D. (2010) · Molecules · doi:10.3390/molecules15117603 · Cited by 363 · see citing works
- Authors
- Shen, L., Jiao, R. H., Ye, Y. H., Wang, X. T., Xu, C., Song, Y. C., Zhu, H. L., & Tan, R. X.
- Affiliations
- State Key Laboratory of Pharmaceutical Biotechnology (CN)
- Corresponding author
- Zhu, Hai L.
- Tan, Ren X.
- Venue
- Chemistry - A European Journal
- Publisher
- Wiley
- Published
- 2006-07-07
- Volume
- 12
- Issue
- 21
- Pages
- 5596-5602
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W2098089414
- Cited by
- 47
- References
- 29
- Citations by year
- 2025: 1 · 2024: 1 · 2022: 1 · 2021: 1 · 2020: 5 · 2019: 4 · 2018: 2 · 2016: 1 · 2015: 2 · 2014: 4 · 2013: 1 · 2012: 2
- FWCI
- 2.51
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Chemistry - A European Journal (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Science Foundation
- Topics
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive Natural Diterpenoids Research
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Keywords
- absolute configuration, Myrothecium roridum, endophytic fungi, Trachelospermum jasminoides, Artemisia annua, cytotoxicity, natural product isolation, structure elucidation
- MeSH terms
- Ascomycota, Circular Dichroism, Poisons, Trichothecenes, Molecular Structure, Crystallography, X-Ray, Macrolides, Nuclear Magnetic Resonance, Biomolecular
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
