Polyacetylenes from the leaves of Vernonia scorpioides (Asteraceae) and their antiproliferative and antiherpetic activities

Pollo, Luiz A.E.; Bosi, Cristiane F.; Leite, Andrea S.; Rigotto, Caroline; Kratz, Jadel M.; Simões, Cláudia Maria Oliveira; Fonseca, David E.P.; Coimbra, Daniel F.; Caramori, Giovanni F.; Nepel, Angelita; Campos, Francinete Ramos; Barison, Andersson; Biavatti, Maique W.

doi:10.1016/j.phytochem.2013.07.011

Cited by 26 publications

(23 citation statements)

References 31 publications

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“…Furthermore, the processing of the raw NMR data can bring information from even longer conjugated chains. The polyacetylenes found by Buskuhl et al 246 and Pollo et al 247 are good examples of this application. In these cases, the employment of enhanced line shape processing permitted the correlation of a long distance coupling ( 9 J ; Fig.…”

Section: New Methodologymentioning

confidence: 87%

The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research

et al. 2019

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Covering: up to 2018With contributions from the global natural product (NP) research community, and continuing the Raw Data Initiative, this review collects a comprehensive demonstration of the immense scientific value of disseminating raw nuclear magnetic resonance (NMR) data, independently of, and in parallel with, classical publishing outlets. A comprehensive compilation of historic to present-day cases as well as contemporary and future applications show that addressing the urgent need for a repository of publicly accessible raw NMR data has the potential to transform natural products (NPs) and associated fields of chemical and biomedical research. The call for advancing open sharing mechanisms for raw data is intended to enhance the transparency of experimental protocols, augment the reproducibility of reported outcomes, including biological studies, become a regular component of responsible research, and thereby enrich the integrity of NP research and related fields.

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Section: New Methodologymentioning

confidence: 87%

The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research

et al. 2019

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“…3) has shown a mild cytotoxic activity against U2OS osteosarcoma cells but not against two other cancer cell lines [73]. Polyacetylene glycosides from Vernonia scorpioides [74,75] and Launaea capitata [76] showed little or no cytotoxic activity. The mechanism of action of these compounds should be further investigated, not in terms of cytotoxic potency but as modulators of amino acid transport, with reference to the mechanism of action of LBT mentioned above.…”

Section: Lobetyolin Analogs With Anticancer Activitiesmentioning

confidence: 99%

Anticancer Properties of Lobetyolin, an Essential Component of Radix Codonopsis (Dangshen)

Bailly

2020

Nat. Prod. Bioprospect.

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Lobetyolin (LBT) is a polyacetylene glycoside found in diverse medicinal plants but mainly isolated from the roots of Codonopsis pilosula, known as Radix Codonopsis or Dangshen. Twelve traditional Chinese medicinal preparations containing Radix Codonopsis were identified; they are generally used to tonify spleen and lung Qi and occasionally to treat cancer. Here we have reviewed the anticancer properties of Codonopsis extracts, LBT and structural analogs. Lobetyolin and lobetyolinin are the mono- and bis-glucosylated forms of the polyacetylenic compound lobetyol. Lobetyol and LBT have shown activities against several types of cancer (notably gastric cancer) and we examined the molecular basis of their activity. A down-regulation of glutamine metabolism by LBT has been evidenced, contributing to drug-induced apoptosis and tumor growth inhibition. LBT markedly reduces both mRNA and protein expression of the amino acid transporter Alanine-Serine-Cysteine Transporter 2 (ASCT2). Other potential targets are proposed here, based on the structural analogy with other anticancer compounds. LBT and related polyacetylene glycosides should be further considered as potential anticancer agents, but more work is needed to evaluate their efficacy, toxicity, and risk–benefit ratio.

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“…This strategy was utilized in the total synthesis of the sensitive triyne natural product (4 S ,5 S )‐4,8‐dihydroxy‐3,4‐dihydrovernoniyne ( 86a ) (Scheme ) and all of its stereoisomers, i.e., (4 S ,5 R ), (4 R ,5 R ) and (4 R ,5 S ) . The natural product 86a was isolated in 2013 by Biavatti and co‐workers and the proposed trans ‐stereostructure was revised through synthesis to be cis ‐(4 S ,5 S ) . Our synthesis of 86a and its diastereomer 86a' from lactone ent ‐ 1 and ent ‐ 17' is depicted in Scheme .…”

Section: Applications Of Lactone 1 and Ent‐1 In Natural Products Smentioning

confidence: 99%

The Potential of β‐Hydroxy‐γ‐vinyl‐γ‐lactone in the Synthesis of Natural Products and Beyond

Fernandes

2020

Eur J Org Chem

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In this mini‐review, we have abstracted the syntheses of β‐hydroxy‐γ‐vinyl‐γ‐lactone and the different tactics and strategies adopted using this important building block in the synthesis of various natural products. Apart from this, the lactone in having a strategic vinyl bond was contemplated as allyl donor in Pd‐catalyzed allylic arylation and also in a cascade Prins‐Ritter reaction. This building block was visualized to be a desymmetrized 3,4‐dihydroxy‐hexyl unit providing orthogonal functional groups for various useful transformations. The active α‐position is available for alkylation, the γ‐vinyl bond, the lactone carbonyl and the β‐hydroxy groups add value to this building block for various possible conversions to natural products and beyond.

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Polyacetylenes from the leaves of Vernonia scorpioides (Asteraceae) and their antiproliferative and antiherpetic activities

Cited by 26 publications

References 31 publications

The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research

The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research

Anticancer Properties of Lobetyolin, an Essential Component of Radix Codonopsis (Dangshen)

The Potential of β‐Hydroxy‐γ‐vinyl‐γ‐lactone in the Synthesis of Natural Products and Beyond

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