Crispoic acid, a new compound from <i>Laelia marginata</i> (Orchidaceae), and biological evaluations against parasites, human cancer cell lines and Zika virus

Belloto, Andrezza Correia; Souza, Gustavo Henrique de; Perin, Paula C.; Schuquel, Ivânia T.A.; Santin, Silvana M. O.; Chiavelli, Lucas Ulisses Rovigatti; Garcia, Francielle P.; Kaplum, Vanessa; Rodrigues, Jean Henrique S.; Scariot, Débora B.; Delvecchio, Rodrigo; Machado-Ferreira, Erik; Aguiar, Renato Santana; Soares, Carlos A. G.; Nakamura, Celso V.; Pomini, Armando M.

doi:10.1080/14786419.2017.1395428

Cited by 9 publications

(7 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It was also discovered that the benzyl protecting group of 53 was removed during the acidic hydrolysis, allowing the synthesis of ( S )-eucomic acid ( 83 ), the non-natural enantiomer of a metabolite that stimulates cytochrome c oxidase (CcO) activity, in a swift manner. The same sequence of transformation can be applied to bis-chloro-alcohol 47 and generate the tetraethyl ester of naturally occurring and antiparasitic crispoic acid ( 85 ). Meanwhile, nucleophiles other than cyanide can also participate in the substitution relay.…”

Section: Resultsmentioning

confidence: 99%

A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides

et al. 2022

View full text Add to dashboard Cite

Enantioenriched tertiary alkyl halides are prevalent in bioactive molecules and can serve as versatile synthetic intermediates to construct complex structures. While conventional access to these motifs often hinges on stereoselective carbon− halogen or carbon−carbon bond formation reactions, desymmetric approaches using halogenated and prochiral tetrasubstituted carbons are largely elusive in comparison. Here, we report that a suite of dinuclear zinc catalysts with a prolinol-or pipecolinolderived tetradentate ligand can reductively desymmetrize a large collection of easily available halomalonic esters to α-halo-βhydroxyesters. These polyfunctionalized tertiary alkyl fluorides, chlorides, and bromides proved to be useful intermediates toward fluorinated drug analogs and polyhalogenated monoterpenes. The facile intramolecular epoxidation of the chiral chloride and bromide products has also enabled expeditious access to natural products containing tertiary alcohol motifs.

show abstract

Section: Resultsmentioning

confidence: 99%

A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Chemical study of the species Laelia marginata and Maxillaria picta, native to southern Brazil, led to the identification of 24-methylenecycloartenol (4) (Almeida et al 2014). The tissues of M. picta also contain the triterpene eburicol (5), a possible biosynthetic precursor of compound 4 (Belloto et al 2018). Compound 4 was also reported in the species Epidendrum mosenii.…”

Section: Triterpenes and Diterpenesmentioning

confidence: 99%

“…The phenanthrene 9,10-dihydro-4-methoxy phenanthren-2,7-diol (20) was isolated from Laelia marginata (=Schomburgkia crispa), a species closely related to genus Myrmecophila, and showed antiproliferative activity against HPV-modified HeLa and SiHa cancer cells (CC 50 5.86 ± 0.19 and 20.78 ± 2.72 μg.mL -1 respectively) (Belloto et al 2018). Phenanthrenes and dihydrophenanthrenes have also been isolated from the species Myrmecophilla humboltii (Williams et al 2012).…”

Section: Phenanthrenesmentioning

confidence: 99%

Bioactive natural products from orchids native to the Americas - A review

POMINI,

SAHYUN,

OLIVEIRA

et al. 2023

An. Acad. Bras. Ciênc.

View full text Add to dashboard Cite

The purpose of this review is to provide information on the traditional uses, phytochemical and pharmacological studies performed with species of orchids native to the Americas and the Caribbean Islands. The treatment of inflammation is the most traditional use for plants of this family, specially in Central America, while anti-inflammatory and anticancer assays are oftenly reported in pharmacological investigations. From the chemical point of view, they are sources of phenanthrenoids and stilbenes, rare secondary metabolites not commonly found in other families of plants, as well as cycloartane triterpenes, pyrrolizidine alkaloids and flavonoids. Since just few species were chemically and pharmacologically studied, in comparison to the large number of native species (less than 0.5% of the total), the orchids of the New World may be an interesting niche for the discovery of new, bioactive natural products.

show abstract

“…This botanical family is representative in the plant biodiversity of the Cerrado biome (Flora do Brasil forthcoming, 2020). This biome has little-explored species for economic, pharmacological, medicinal, and ornamental purposes (Belloto et al, 2017;Soares et al, 2020). Thus, native species with possible ornamental potential should be studied, given the high demand for plants to supply the market of flower and ornamental plants.…”

Section: Introductionmentioning

confidence: 99%

Ornamental potential of Schomburkgia crispa Lindl.

et al. 2021

View full text Add to dashboard Cite

Orchids are one of the groups of plants with the greatest commercialization potential. They have floral characteristics highly valued in the sector of flowers and ornamental plants. However, exotics species are the most commercialized. The native species are still little explored for their ornamental potential. Thus, this work describes the vegetative and floral morphological characteristics of Schomburgkia crispa Lindl. aiming at evaluating its ornamental potential. For such, seven individuals were chosen. The quantitative characters were evaluated in all plants, totaling fifty pseudobulbs and eighty-eight flowers. During flowering, the most representative plant was chosen for the visual evaluation of its morphological features through photographs. A floral diagnosis sheet based on photos of fresh flowers was prepared by keeping the maximum level of morphological details. At the end of the experimental period, averages and standard deviations were calculated for each character evaluated. The species S. crispa presented, on average, plants 46.17 cm long, 31.50 cm wide, and with 88 cm of diameter. For flowering characters, the species presented in general 16.50 flowers per plant, 14.67 per flower stem, and 4.66 flowers opened per day, with an average durability of 32 days. Thus, we conclude that the species S. crispa has a great ornamental potential for use in ornamental horticulture.

show abstract

Crispoic acid, a new compound from Laelia marginata (Orchidaceae), and biological evaluations against parasites, human cancer cell lines and Zika virus

Cited by 9 publications

References 15 publications

A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides

A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides

Bioactive natural products from orchids native to the Americas - A review

Ornamental potential of Schomburkgia crispa Lindl.

Contact Info

Product

Resources

About