PUBLICATION
Integrating Molecular Networking and 1H NMR to Target the Isolation of Chrysogeamides from a Library of Marine-Derived Penicillium Fungi
- Authors
- Hou, X.M., Li, Y.Y., Shi, Y.W., Fang, Y.W., Chao, R., Gu, Y.C., Wang, C.Y., Shao, C.L.
- ID
- ZDB-PUB-190105-8
- Date
- 2019
- Source
- The Journal of organic chemistry 84(3): 1228-1237 (Journal)
- Registered Authors
- Keywords
- none
- MeSH Terms
-
- Aquatic Organisms
- Biological Products/chemistry*
- Fungi/chemistry*
- Penicillium/chemistry*
- Proton Magnetic Resonance Spectroscopy
- Tandem Mass Spectrometry/methods*
- PubMed
- 30609359 Full text @ J. Org. Chem.
Citation
Hou, X.M., Li, Y.Y., Shi, Y.W., Fang, Y.W., Chao, R., Gu, Y.C., Wang, C.Y., Shao, C.L. (2019) Integrating Molecular Networking and 1H NMR to Target the Isolation of Chrysogeamides from a Library of Marine-Derived Penicillium Fungi. The Journal of organic chemistry. 84(3):1228-1237.
Abstract
A challenging problem in natural product discovery is to rapidly dereplicate known compounds and expose novel ones from complicated components. Herein, integrating the LC-MS/MS-dependent molecular networking and 1H NMR techniques efficiently and successfully enabled the targeted identification of seven new cyclohexadepsipeptides, chrysogeamides A-G (1-7), from the coral-derived fungus Penicillium chrysogenum (CHNSCLM-0003) which was targeted from a library of marine-derived Penicillium fungi. Compound 4 features a rare 3-hydroxy-4-methylhexanoic acid (HMHA) moiety which was firstly discovered from marine-derived organisms. Interestingly, isotope labelling feeding experiments confirmed that 13C1-L-Leu was transformed into 13C1-D-Leu moiety indicating that D-Leu could be isomerized from L-Leu. Compounds 1 and 2 obviously promoted angiogenesis in zebrafish at 1.0 μg/mL, with non-toxic to embryonic zebrafish at 100 μg/mL. Combining molecular networking with 1H NMR as a discovery tool will be implemented as a systematic strategy, not only for known compounds dereplication but also for untapped reservoir discovery.
Genes / Markers
Expression
Phenotype
Mutations / Transgenics
Human Disease / Model
Sequence Targeting Reagents
Fish
Orthology
Engineered Foreign Genes
Mapping