LC–PDA–MS/MS-Based Dereplication Guided Isolation of a New Optical Isomer of 19,20-Epoxycytochalasin-N and Its Cytotoxic Activity

Abstract

The Rosellinia sanctae - cruciana extract was subjected to detailed liquid chromatography tandem mass spectrometry studies. A total of 38 peaks were annotated to m / z 508.26, m / z 510.28, m / z 524.26, m / z 526.28, m / z 540.26, m / z 542.27, and m / z 584.28 [M + H] + . The accurate mass, mutually supported UV/vis spectra, and database search identified these compounds as cytochalasins. Systematic dereplication helped identify a peak at m / z 540.26 [M + H] + as the new compound. Further, the identified compound was purified by high-performance liquid chromatography and characterized by 2D NMR to be 19,20-epoxycytochalasin N1, a new optical isomer of 19,20-epoxycytochalasin-N. It exhibited substantial cytotoxicity with IC 50 values ranging from 1.34 to 19.02 μM. This study shows a fast approach for dereplicating and identifying novel cytochalasin metabolites in crude extracts.

Isolation of cytotoxic cycloartane triterpenoids from Dysoxylum malabaricum

“…For rapid identification of the metabolites at an early stage, we adopted the LCMS-DNP-based dereplication strategy. 16 A DNP search revealed 380 compounds from Dysoxylum, and 184 of them were triterpenoids. As noticed from LCMS, all these compounds showed a mass range of 400–600 Da confirming the presence of triterpenoids.…”

Chemodiversity and Anti-Leukemia Effect of Metabolites from Penicillium setosum CMLD 18

“…Thus, recently, we have observed an expressive number of reports with the prospect of reinvestigating known matrices [ 28 , 29 ]. This dynamic offers new opportunities for accelerating access to new drug candidates, in particular, with cytotoxic potential [ 30 , 31 , 32 , 33 ]. In this sense, if we especially consider the Penicillium genus, our recent survey on the anti-leukemia potential of 76 compounds related to this group of fungi [ 2 ] showed that different classes of natural products present anti-leukemia effects, such as alkaloids (25% of the total), peptides/proteins (9%), polyketides (57%), and terpenoids (9%).…”

An Efficient Workflow for Quality Control Marker Screening and Metabolite Discovery in Dietary Herbs by LC-Orbitrap-MS/MS and Chemometric Methods: A Case Study of Chrysanthemum Flowers

“…It remains a challenge to procure advantageous and comprehensive insights from the wealth of information provided by LC-MS [4]. Specifically, LC-MS cannot distinguish isomers, suffers from in-source fragmentation (ISF) interference, and relies on inaccurate online database matching of precursor ions [5,6]. Although some product ion spectrum libraries can improve identification reliability, identifying compounds with few and less abundant fragments is still problematic [7].…”