Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of <i>Geissospermum laeve</i>

Ramos, Alexander E. Fox; Alcover, Charlotte; Evanno, Laurent; Maciuk, Alexandre; Litaudon, Marc; Duplais, Christophe; Bernadat, Guillaume; Gallard, Jean‐François; Jullian, Jean‐Christophe; Mouray, Elisabeth; Grellier, Philippe; Loiseau, Philippe M.; Pomel, Sébastien; Poupon, Erwan; Champy, Pierre; Beniddir, Mehdi A.

doi:10.1021/acs.jnatprod.6b01013

Cited by 53 publications

(42 citation statements)

References 46 publications

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“…The use of molecular networking as a dereplication strategy has been successfully articulated effectively earlier, and successful dereplication using molecular networking involves three main steps: (i) acquisition of tandem mass spectra, (ii) the generation of molecular networks (iii) and analyses using various mechanisms (Yang et al, 2013). In particular, it has been emphasized that reference LC-MS/MS spectra of known compounds and/or previously isolated and well-characterized compounds can be generated in the same manner as the sample to aid in the dereplication process by serving as a "seed" (Fox Ramos et al, 2017;Yang et al, 2013). However, it should be noted that application of molecular networking is not strictly dependent on databases or reference compounds (Yang et al, 2013).…”

Section: Molecular Networking As a Dereplication Toolmentioning

confidence: 99%

Current status and contemporary approaches to the discovery of antitumor agents from higher plants

Agarwal

Carcache

Addo

et al. 2020

Biotechnology Advances

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Higher plant constituents have afforded clinically available anticancer drugs. These include both chemically unmodified small molecules and their synthetic derivatives currently used or those in clinical trials as antineoplastic agents, and an updated summary is provided. In addition, botanical dietary supplements, exemplified by mangosteen and noni constituents, are also covered as potential cancer chemotherapeutic agents. Approaches to metabolite purification, rapid dereplication, and biological evaluation including analytical hyphenated techniques, molecular networking, and advanced cellular and animal models are discussed. Further, enhanced and targeted drug delivery systems for phytochemicals, including micelles, nanoparticles and antibody drug conjugates (ADCs) are described herein.

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Section: Molecular Networking As a Dereplication Toolmentioning

confidence: 99%

Current status and contemporary approaches to the discovery of antitumor agents from higher plants

Agarwal

Carcache

Addo

et al. 2020

Biotechnology Advances

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“…It has allowed rapid comparison using MS profiles of complex extracts and gained much attention in the discovery of novel natural products . To date, the applications of GNPS have led to the discovery of large numbers of natural products such as spongonucleosides, aminopolyketide derivatives, di‐ and tri‐chlorinated acyl‐amides, glycopeptides, monoterpene indole alkaloids, and cyclic lipopeptides, most of which were metabolites from microbiota and rarely reported for plant‐derived natural products. Recently, structurally different triterpene saponins from Eleutherococcus senticosus leaves and phenolics in litchi pulp have been successfully revealed by GNPS …”

Section: Introductionmentioning

confidence: 99%

Structural characterization and discrimination of Paris polyphylla var. yunnanensis by a molecular networking strategy coupled with ultra‐high‐performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

Wang

Fan

Xiang

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale: Paris polyphylla var. yunnanensis (Franch) Hand Mazz (PPY) is a traditionalChinese medicine with antitumor, antibacterial, hemostatic, and anthelmintic activities. Identification of the chemical composition in PPY is helpful to discover its active ingredients and can be used to establish its quality control protocols.Methods: The composition of PPY was identified using ultra-high-performance liquid chromatography combined with quadrupole time-of-flight mass spectrometry (UHPLC/QTOF-MS/MS) coupled with a molecular networking strategy. First, the UHPLC/QTOF-MS/MS approach was optimized for chemical compound profiling.Then, the MS data were processed using PeakView™ combined with an in-house database to quickly characterize the secondary metabolites. Finally, molecular networking excavated new molecular weights to discover unknown or trace natural products based on the characteristics of each cluster. Results:A total of 222 compounds, including 77 isospirostanols, 2 spirostanols, 19 furostanols, 10 pseudospirostanols, 6 cholesterols, 10 C 21 steroids, 5 insect metamorphosis hormones, 3 plant sterols, 6 five-ring triterpenoids, 4 flavonoids, 8 fatty acids, 2 phenylpropanoids, and 8 other compounds, were characterized in PPY by comparing their main fragmentation characteristics and pathways with the literature data, and 62 of them, 54 steroidals and 8 phenylpropanoids, were discovered or tentatively identified for the first time. Conclusions:This study extended the application of a molecular networking strategy to traditional herbal medicines and developed a molecular networking based screening approach with a significant increase in efficiency for the discovery and identification of trace novel natural products.Yumei Wang and Qian Fan contributed equally to this work as first authors. Paris polyphylla var. yunnanensis (Franch) Hand Mazz (PPY), calledChong Lou, is a well-known, valuable traditional Chinese medicine (TCM) that has been used to treat fractures, hemorrhages, snake bites, and abscess for many years. 1,2 PPY has been used as a main ingredient for the preparation of many TCMs, such as Yunnan Baiyao, Gongxuening capsules, and Jidesheng Sheyao tablets. 3 Phytochemistry studies have indicated that the dried rhizomes of Paris species contain steroidal saponins, triterpenoid saponins, flavonoids, phenylpropanoids, ecdysteroids, phenolic glycosides, and so on. 4-6 The glucosyl groups of steroidal saponins are normally attached to the steroidal aglycones through the hydroxyl groups at the C-3 and/or C-26 positions (and sometimes the C-1, C-21, C-23, and C-24 positions). Four types of steroidal sapogenins 6 (spirostanol, isospirostanol, furostanol, and pseudospirostanol) are considered major aglycones, and typical sugars are arabinose, xylose, apiose, fucose, rhamnose, glucose, and galactose. Comprehensive identification of ingredients in PPY is critical to understanding its biological mechanism and establishing quality control protocols. Because of the complexity of these components, their comprehensive...

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“…A targeted analysis of MS/MS data was facilitated by introducing a molecular networking approach in the data analysis workflow. MN is becoming one of the most efficient tools for the analysis of untargeted MS/MS data, allowing dereplication of complex extracts and exploration of molecular diversity 21 . We have showed here that MN is also valuable for targeted metabolite fingerprinting.…”

Section: Discussionmentioning

confidence: 99%

Clerodane furanoditerpenoids as the probable cause of toxic hepatitis induced by Tinospora crispa

Cachet¹,

Langrand²,

Riffault-Valois³

et al. 2018

Sci Rep

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Tinospora crispa is a popular traditional herbal plant commonly used throughout the world for treatment of various diseases, in particular type 2 diabetes mellitus. We report here a new case of toxic hepatitis in a 57-year old male patient in the French West Indies following the consumption of two aqueous extracts of fresh Tinospora crispa stems. It thus differs from two previously reported cases that concerned the chronic intake of powdered dry stems delivered in solid oral dosage forms (i.e. pellets and tablets). Liquid Chromatography-Diode Array Detection-Mass Spectrometry (LC/DAD/MS) analyses were performed on an aqueous extract of the offending sample that mimics the swallowed preparation. They revealed the presence of species-specific molecular marker borapetoside C (1) and thus enabled an unambiguous phytochemical identification. The exploration of tandem MS/MS data obtained by ultra-high performance liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry (UHPLC-ESI-QTOF-HRMS) allowed the identification of 17 additional cis-clerodane-type furanoditerpenoid lactones, analogues of 1. These results support the hypothesis that the mechanisms underlying hepatotoxicity of Tinospora crispa are the same as those encountered with furanoditerpenoids-containing plants such as Teucrium chamaedrys or Dioscorea bulbifera. In the context of type 2 diabetes treatment, we recommend that Tinospora crispa intake should be more closely monitored for signs of hepatotoxicity.

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Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve

Cited by 53 publications

References 46 publications

Current status and contemporary approaches to the discovery of antitumor agents from higher plants

Current status and contemporary approaches to the discovery of antitumor agents from higher plants

Structural characterization and discrimination of Paris polyphylla var. yunnanensis by a molecular networking strategy coupled with ultra‐high‐performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

Clerodane furanoditerpenoids as the probable cause of toxic hepatitis induced by Tinospora crispa

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