Applying molecular networking for targeted isolation of depsipeptides

Xiao, Lin; Chai, Limin; Zhu, Hong Rui; Zhou, Yongjun; Shen, Yaoyao; Chen, Kai Hao; Sun, Fan; Liu, Bu Ming; Xu, Shi Hai; Lin, Hou Wen

doi:10.1039/d0ra09388b

Cited by 4 publications

(8 citation statements)

References 21 publications

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“…The authentic standards of the (S)-MTPA esters were prepared as part of our previous study. 19 Nine sets of standards and samples were subjected to C 18 Mosher analysis, and the results suggested the presence of L-Ila and 2S-Hia moieties in 1−7 (Figure S55). Advanced Marfey's analysis confirmed the presence of L-threonine (L-Thr) residues in 1−7.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Recently, we reported a new set of neoantimycin congeners (unantimycins (UAT) B–E) featuring an unusual 3-hydroxybenzoate (3-HBA) moiety. These neoantimycin derivatives demonstrated considerable growth inhibitory activity against several cancer cell lines without significant toxicity toward noncancerous cells. , Mechanistically, UAT-B revealed a distinctive mode of antitumor action by disrupting the interaction between TNKS and USP25, leading to the subsequent inhibition of the Wnt pathway. This identified UAT-B as a promising lead compound for colorectal cancer therapy.…”

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confidence: 99%

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Precursor-Directed Biosynthesis of Neoantimycin Derivatives with Selective Cytotoxicity

Li,

Chai,

Tang

et al. 2024

J. Nat. Prod.

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A precursor-directed biosynthesis approach led to the accumulation of seven new neoantimycin derivatives (1−7) from Streptomyces conglobatus RJ2. Structure elucidation was conducted using NMR and HRESIMS analysis, and the absolute configuration was determined by advanced Marfey's method, Mosher's analysis, and ECD analysis. The obtained compounds revealed selective and significant cytotoxicity, specifically against colorectal cancer cells bearing the K-ras mutation, with IC 50 values ranging from 40 nM to 3.5 μM.

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Section: ■ Results and Discussionmentioning

confidence: 99%

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confidence: 99%

Precursor-Directed Biosynthesis of Neoantimycin Derivatives with Selective Cytotoxicity

Li,

Chai,

Tang

et al. 2024

J. Nat. Prod.

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“…Most of researchers used this technology to identify (new/novel) metabolites or dereplicate in different crude extracts ( Jin et al, 2018 ; Wang et al, 2020 ). Recently, a molecular networking technique based on (U)HPLC-MS/MS combined with different databases was used in the dereplication and targeting of new natural products from diverse biological resources ( Watrous et al, 2012 ; Yang et al, 2013 ; Aksenov et al, 2017 ; Hou et al, 2019 ; Ramos et al, 2019 ; Rivera-Chaìvez et al, 2019 ; Shi et al, 2019 ; Wu et al, 2019 ; Chao et al, 2020 ; Zang et al, 2020 ; Lei et al, 2021 ; Lin et al, 2021 ). The molecular networking technique used the known or new compound as the “seed” to realize the visualization of analogues.…”

Section: Discussionmentioning

confidence: 99%

UPLC-Q-TOF-MS/MS Analysis of Seco-Sativene Sesquiterpenoids to Detect New and Bioactive Analogues From Plant Pathogen Bipolaris sorokiniana

Wang

Yang

et al. 2022

Front. Microbiol.

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Seco-sativene sesquiterpenoids are an important member of phytotoxins and plant growth regulators isolated from a narrow spectrum of fungi. In this report, eight seco-sativene sesquiterpenoids (1–8) were first analyzed using the UPLC-Q-TOF-MS/MS technique in positive mode, from which their mass fragmentation pathways were suggested. McLafferty rearrangement, 1,3-rearrangement, and neutral losses were considered to be the main fragmentation patterns for the [M+1]+ ions of 1–8. According to the structural features (of different substitutes at C-1, C-2, and C-13) in compounds 1–8, five subtypes (A–E) of seco-sativene were suggested, from which subtypes A, B/D, and E possessed the diagnostic daughter ions at m/z 175, 189, and 203, respectively, whereas subtype C had the characteristic daughter ion at m/z 187 in the UPLC-Q-TOF-MS/MS profiles. Based on the fragmentation patterns of 1–8, several known compounds (1–8) and two new analogues (9 and 10) were detected in the extract of plant pathogen fungus Bipolaris sorokiniana based on UPLC-Q-TOF-MS/MS analysis, of which 1, 2, 9, and 10 were then isolated and elucidated by NMR spectra. The UPLC-Q-TOF-MS/MS spectra of these two new compounds (9 and 10) were consistent with the fragmentation mechanisms of 1–8. Compound 1 displayed moderate antioxidant activities with IC50 of 0.90 and 1.97 mM for DPPH and ABTS+ scavenging capacity, respectively. The results demonstrated that seco-sativene sesquiterpenoids with the same subtypes possessed the same diagnostic daughter ions in the UPLC-Q-TOF-MS/MS profiles, which could contribute to structural characterization of seco-sativene sesquiterpenoids. Our results also further supported that UPLC-Q-TOF-MS/MS is a powerful and sensitive tool for dereplication and detection of new analogues from crude extracts of different biological origins.

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“…[18][19][20] This technique allows us to easily categorize structurally similar compounds as a "molecular family" based on MS/MS spectral similarity and to dereplicate known compounds by a search of the Global Natural Product Social Molecular Networking (GNPS) spectral library. This approach has recently been utilized for the (re)investigation of biologically important compounds such as phorbols, [21,22] depsipeptides, [23,24] and terpenoid indole alkaloids. [25,26] It has been widely speculated that most marine natural products found in marine invertebrates are not produced by these creatures themselves, but rather by their symbiotic microbes or prey.…”

Section: Introductionmentioning

confidence: 99%

Discovery of New Cytotoxic Aplaminone Derivatives from the Sea Hare Aplysia kurodai and Elucidation of Their Accumulation from Local Sea Algae through the Food Chain

Hioki

Shimoda²,

Iwao

et al. 2023

Eur J Org Chem

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The shell‐less herbivorous marine mollusk (sea hare) Aplysia kurodai is known to contain a variety of bioactive substances. While these compounds have been thought to originate from sea algae or their associated microbes, most of their origin and acquisition pathways are still unclear. Six new cytotoxic aplaminone derivatives, bromodopamine‐terpenoid hybrid molecules, were isolated from A. kurodai. Among them, isoaplaminone had a reverse prenyl group at the C15 aliphatic chain, which is a rare structural feature from the viewpoint of terpenoid biosynthesis. Investigation for chemical components in A. kurodai and the sea algae collected at several different locations revealed that two major aplaminones were contained in the Laurencia complex species at specific sites. Our chemical and ecological studies provide new insights into the origin of marine alkaloid toxins and their dynamism through the food chain.

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Applying molecular networking for targeted isolation of depsipeptides

Abstract: LC-HRMS/MS molecular networking enabled the targeted isolation of three new neoantimycin analogs (1, 3, 5) and two known ones (2, 4) from the culture broth of Streptomyces conglobatus RJ8.

Cited by 4 publications

References 21 publications

Precursor-Directed Biosynthesis of Neoantimycin Derivatives with Selective Cytotoxicity

Precursor-Directed Biosynthesis of Neoantimycin Derivatives with Selective Cytotoxicity

UPLC-Q-TOF-MS/MS Analysis of Seco-Sativene Sesquiterpenoids to Detect New and Bioactive Analogues From Plant Pathogen Bipolaris sorokiniana

Discovery of New Cytotoxic Aplaminone Derivatives from the Sea Hare Aplysia kurodai and Elucidation of Their Accumulation from Local Sea Algae through the Food Chain

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