Integrated analytical workflow for chromatographic profiling and metabolite annotation of a cytotoxic Phorbas amaranthus extract

Amaral, Bruno S. do; Silva, Fernanda B. da; Leme, Gabriel Mazzi; Schmitz, Letícia S.S.; Jimenez, Paula Christine; Martins, Roberto Carlos Campos; Cass, Quézia B.; Valverde, Alessandra L.

doi:10.1016/j.jchromb.2021.122720

Cited by 3 publications

(12 citation statements)

References 72 publications

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“…As regards steroids, phorbasterones A-D (29)(30)(31)(32), displayed moderate cytotoxicity toward HCT-116 cells [45]. In support of these observations, more recently, the lipid fraction from P. amaranthus, likely enriched of sterols, was found to possess antiproliferative properties in HCT-116 cells [67].…”

Section: Cytotoxic and Cytostatic Activitymentioning

confidence: 70%

“…Phorbasin H (94) displays a carboxylic function, as well as phorbasin I (95) which differs from the former by the position of a double bond in the side chain [53]. Recently the synthesis of phorbasin H (94) was carried out and the absolute configuration of the natural product was determined as S [66] A dereplication work with LCMS, showed the presence of these phorbasins G-I in the extract of P. amaranthus [67].…”

Section: Phorbasinsmentioning

confidence: 99%

“…Recently a dereplication study, based upon comparison of HR-MS fragmentation pathways, allowed the annotation of 18 known Phorbas metabolites, for the extract of P. amaranthus, collected in Brazil. Among the known compounds are: phorbasins (87-89, 90-92, 93-95, 96-100), phorbaketals (45)(46)(47)49), isophorbasone (78), ansellones (72), anvillones (80) and phorbasterones (34)(35)(36)(37)(38)(39) [67].…”

Section: Other Compounds Identified In P Amaranthusmentioning

confidence: 99%

“…The GNPS also suggested other 29 metabolites annotated through a molecular subnetwork. Some examples of these metabolites are shown in Figure 34 [67].…”

Section: Other Compounds Identified In P Amaranthusmentioning

confidence: 99%

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Exploring Chemical Diversity of <em>Phorbas</em> Sponges as a Source of Novel Lead Compounds in Drug Discovery

Caso¹,

Silva²,

Esposito³

et al. 2021

Preprint

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Porifera, commonly referred to as marine sponges, have stood out as major producers of marine natural products (MNPs). Sponges of the genus Phorbas have attracted much attention along years. They are widespread in all continents, and several structurally unique compounds have been identified from species of this genus. Terpenes, mainly sesterterpenoids, represent the great majority of secondary metabolites isolated from Phorbas species, even though several alkaloids and steroids have also been reported. Many of these compounds have shown a variety of biological activities. Particularly, Phorbas sponges have been demonstrated to be a source of cytotoxic metabolites. In addition, MNPs exhibiting cytostatic, antimicrobial and anti-inflammatory activities, have been isolated and structurally characterized. This work brings an overview of Phorbas secondary metabolites reported since the first study published in 1993 until 2020, and their biological activities.

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Section: Cytotoxic and Cytostatic Activitymentioning

confidence: 70%

Section: Phorbasinsmentioning

confidence: 99%

Section: Other Compounds Identified In P Amaranthusmentioning

confidence: 99%

“…The GNPS also suggested other 29 metabolites annotated through a molecular subnetwork. Some examples of these metabolites are shown in Figure 34 [67].…”

Section: Other Compounds Identified In P Amaranthusmentioning

confidence: 99%

See 2 more Smart Citations

Exploring Chemical Diversity of <em>Phorbas</em> Sponges as a Source of Novel Lead Compounds in Drug Discovery

Caso¹,

Silva²,

Esposito³

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

“…Based on MS/MS spectra, the lysophosphatidylcholines shared six common characteristic fragment ion peaks of m/z 258/184/125/104/86/60 (matched six peaks) with high response. While lysophosphatidylcholines were evidenced through the similarity of MS/MS fragmentation patterns with four discriminant ions at m/z 258/184/125/104 in several literature [17, 18]. In the MS spectra, the molecular formulae of 5 lysophosphatidylcholines (compounds 82, 87, 89, 91, and 94) with quasi‐molecular ions of m/z 522.3560, m/z 520.3390, and m/z 496.3304 were deduced as C 26 H 50 NO 7 P, C 26 H 50 NO 7 P, and C 24 H 50 NO 7 P, respectively.…”

Section: Resultsmentioning

confidence: 93%

Chemical and metabolic profiling of Codonopsis Radix extract with an integrated strategy using ultra‐high‐performance liquid chromatography coupled with mass spectrometry

Tang

Zeng

Wang

et al. 2022

J of Separation Science

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Codonopsis radix was commonly used as food materials or herbal medicines in many countries. However, the comprehensive analysis of chemical constituents, and in vivo xenobiotics of Codonopsis radix remain unclear. In the present study, an integrated strategy with feature-based molecular networking using ultrahigh-performance liquid chromatography coupled with mass spectrometry was established to systematically screen the chemical constituents and the in vivo xenobiotics of Codonopsis radix. A step-by-step manner based on a composition database, visual structure classification, discriminant ions, and metabolite software prediction was proposed to overcome the complexities due to the similar structure of chemical constituents and metabolites of Codonopsis radix. As a result, 103 compounds were tentatively characterized, 20 of which were identified by reference standards. Besides, a total of 50 xenobiotics were detected in vivo, including 26 prototypes and 24 metabolites, while the metabolic features of the pyrrolidine alkaloids were elucidated for the first time. The metabolism reactions of pyrrolidine alkaloids and sesquiterpene lactones included oxidation, methylation, hydration, hydrogenation, demethylation, glucuronidation, and sulfation. This study provided a generally applicable approach to the comprehensive investigation of the chemical and metabolic profile of traditional Chinese medicine and offered reasonable guidelines for further screening of quality control indicators and pharmacodynamics mechanism of Codonopsis radix.

show abstract

Exploring Chemical Diversity of Phorbas Sponges as a Source of Novel Lead Compounds in Drug Discovery

et al. 2021

View full text Add to dashboard Cite

Porifera, commonly referred to as marine sponges, are acknowledged as major producers of marine natural products (MNPs). Sponges of the genus Phorbas have attracted much attention over the years. They are widespread in all continents, and several structurally unique compounds have been identified from this species. Terpenes, mainly sesterterpenoids, are the major secondary metabolites isolated from Phorbas species, even though several alkaloids and steroids have also been reported. Many of these compounds have presented interesting biological activities. Particularly, Phorbas sponges have been demonstrated to be a source of cytotoxic metabolites. In addition, MNPs exhibiting cytostatic, antimicrobial, and anti-inflammatory activities have been isolated and structurally characterized. This review provides an overview of almost 130 secondary metabolites from Phorbas sponges and their biological activities, and it covers the literature since the first study published in 1993 until November 2021, including approximately 60 records. The synthetic routes to the most interesting compounds are briefly outlined.

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Integrated analytical workflow for chromatographic profiling and metabolite annotation of a cytotoxic Phorbas amaranthus extract

Cited by 3 publications

References 72 publications

Exploring Chemical Diversity of <em>Phorbas</em> Sponges as a Source of Novel Lead Compounds in Drug Discovery

Exploring Chemical Diversity of <em>Phorbas</em> Sponges as a Source of Novel Lead Compounds in Drug Discovery

Chemical and metabolic profiling of Codonopsis Radix extract with an integrated strategy using ultra‐high‐performance liquid chromatography coupled with mass spectrometry

Exploring Chemical Diversity of Phorbas Sponges as a Source of Novel Lead Compounds in Drug Discovery

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