Cardenolides in the defensive fluid of adult large milkweed bugs have differential potency on vertebrate and invertebrate predator Na+/K+¬–ATPases DOI Open Access
Paola Rubiano-Buitrago, Shrikant Pradhan, Alfonso Aceves‐Aparicio

et al.

Authorea (Authorea), Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 6, 2023

The defences of aposematic animals are characterised by diversity and variability secondary metabolites. Here we examine the nature function chemical defence in large milkweed bugs, Oncopeltus fasciatus, testing hypothesis that different compounds have evolved response to enemies. We profiled quantified cardenolides sequestered bugs their defensive secretions bodies, measured inhibitory properties a subset isolated insect’s against Na+/K+—ATPase target site vertebrate invertebrate predators, using porcine data as reference. show highly concentrated coroglaucigenin (glucopyranosyl frugoside frugoside) toxic for both resistant sensitive whereas corotoxigenin calotropagenin varying degrees enzyme inhibition among various predators. Overall, O. fasciatus is well defended range enemies due differential effect these compounds´ sites. Our results suggest insect sequester predation pressure.

Language: Английский

Evidence for the efficacy of anti-inflammatory plants used in Brazilian traditional medicine with ethnopharmacological relevance DOI
Rafael Christian de Matos,

Ana Flávia Alvarenga Bitencourt,

Alexsandro Davi Mantovani de Oliveira

et al.

Journal of Ethnopharmacology, Journal Year: 2024, Volume and Issue: 329, P. 118137 - 118137

Published: April 2, 2024

Language: Английский

Citations

4

HPLC-MS standardization and validation methods for determination of calactin content in dichloromethane fraction of Calotropis gigantea (L.) Dryand. (Niu jiao gua) stem bark and its application in prediction of anticancer activities DOI Creative Commons

Naphat Kaewpaeng,

Sudaporn Wongwan,

Khemmachat Pansooksan

et al.

Heliyon, Journal Year: 2025, Volume and Issue: 11(3), P. e41963 - e41963

Published: Jan. 18, 2025

Calactin, a doubly-linked cardenolide, is commonly found in Apocynaceae family including Calotropis gigantea (L.) Dryand. (Niu jiao gua, C. gigantea). This phytochemical has gained recognition for its potential as an anticancer agent and marker properties. Our previous reports demonstrated the remarkable anti-liver anti-colon cancer activities both vitro vivo of dichloromethane fraction from stem barks (CGD). However, quantitative analysis calactin content CGD by using high-performance liquid chromatography (HPLC) - ultraviolet (UV) method was limited. Therefore, this study aimed to develop more sensitive reliable measurement HPLC- electrospray ionization mass spectrometry (ESI-MS) application on quality control prediction activity CGD. The utilized HPLC-ESI-MS system, negative mode, standardization validation. An octadecylsilane column mixture acetonitrile water containing 0.1 % formic acid gradient system were used stationary phase mobile phase, respectively. validated terms linearity, accuracy, precision, recovery, limit detection (LOD), quantitation (LOQ). linearity developed technique verified within concentrations range 1 50 μg/mL, exhibiting linear coefficient determination (R2) greater than 0.998. LOD LOQ proposed methodology met acceptance criteria according International Council Harmonization Technical Requirements Pharmaceuticals Human Use (ICH) guideline Q2(R1). suitable Additionally, we suggest applying established protocol quantify contents CGDs collected over period one year (12 months) investigate correlation their cytotoxicities against human cell lines derived colon (HCT116), hepatoblastoma (HepG2) line stomach metastasized liver (MKN74). will help predicting cytotoxicity HCT116, HepG2 MKN74. In summary, further utilization.

Language: Английский

Citations

0

Antioxidant availability trades off with warning signals and toxin sequestration in the large milkweed bug (Oncopeltus fasciatus) DOI Creative Commons
H. Cecilia Heyworth, Prayan Pokharel, Jonathan D. Blount

et al.

Ecology and Evolution, Journal Year: 2023, Volume and Issue: 13(4)

Published: April 1, 2023

In some aposematic species the conspicuousness of an individual's warning signal and concentration its chemical defense are positively correlated. Several mechanisms have been proposed to explain this phenomenon, including resource allocation trade-offs where same limiting is needed produce both defense. Here, large milkweed bug (

Language: Английский

Citations

6

Differential accumulation of cardenolides from Asclepias curassavica by large milkweed bugs does not correspond to availability in seeds or biological activity on the bug Na+/K+-ATPase DOI Creative Commons
Paola Rubiano-Buitrago, Shrikant Pradhan, Veit Grabe

et al.

Frontiers in Ecology and Evolution, Journal Year: 2023, Volume and Issue: 11

Published: June 8, 2023

Milkweed–herbivore systems are characterized by cardenolide chemical defenses and specialized herbivore adaptations such as physiological target site insensitivity. Cardenolide in milkweeds can vary terms of the total concentration, differences polarity individual cardenolides, substitution steroidal structures that contribute to molecule's reactivity. The variability could represent plant's response natural selection adaptation resistant herbivores is a characteristic phenotype-matching between defensive offensive traits resulting from coevolution. Here, we test phenotypic match composition seeds Asclepias curassavica those sequestered nymphs adults seed Oncopeltus fasciatus , combined with tests inhibitory capacity subset cardenolides against Na + /K -ATPase O. non-adapted insect ( Drosophila melanogaster ). We compare this highly sensitive porcine -ATPase. Among five most abundant present milkweed seeds, glucopyranosyl frugoside, gofruside, calotropin were significantly more than nymphs; bugs contained higher concentrations deglucosylated compounds. compound, was also for but tolerant all compounds compared D. enzyme. Our results add evidence sequesters specific its host plants not directly linked concentration potency.

Language: Английский

Citations

4

Cardenolides in the defensive fluid of adult large milkweed bugs have differential potency on vertebrate and invertebrate predator Na + /K + -ATPases DOI Creative Commons
Paola Rubiano-Buitrago,

S. Pradhan,

A. A. Aceves

et al.

Royal Society Open Science, Journal Year: 2024, Volume and Issue: 11(6)

Published: June 1, 2024

Aposematic animals rely on diverse secondary metabolites for defence. Various hypotheses, such as competition, life history and multifunctionality, have been posited to explain defence variability diversity. We investigate the compound selectivity hypothesis using large milkweed bugs, Oncopeltus fasciatus , determine if distinct cardenolides vary in toxicity different predators. quantify bug’s defensive secretions body tissues test individual compounds against predator target sites, Na + /K -ATPases, that are predicted differ sensitivity. Frugoside, gofruside, glucopyranosyl frugoside gofruside were dominant of insects, whereas two monoglycosidic cardenolides—frugoside gofruside—were most abundant fluid. These highly toxic (IC 50 < 1 μM) an invertebrate a sensitive vertebrate enzyme, comparison glucosylated compounds. Gofruside was weakest inhibitor putatively resistant predator. Glucopyranosyl calotropin, found only 60% also effective enzymes. Our results suggest sequestered by O. probably provide consistency protection range predators underscore need consider communities prey evolution.

Language: Английский

Citations

1

Research Progress on Plant‐Derived Cardenolides (2010–2023) DOI

Yilin He,

Hong‐Ying Yang,

Lei Zhang

et al.

Chemistry & Biodiversity, Journal Year: 2024, Volume and Issue: 21(12)

Published: Aug. 17, 2024

Abstract Cardenolides are a class of steroidal glycoside compounds that mainly distributed in plants, have significant physiological activity the heart, and been used clinically for over 200 years. To provide reference further research development these compounds, phytochemical biological properties natural cardenolides (295 total) isolated between 2010 2023 from 17 families hundreds species belonging to 70–80 genera were reviewed. In vitro vivo studies indicated antitumor, antibacterial, antiviral activities most commonly reported pharmacological cardenolides. Antitumor thoroughly studied understand their structure‐activity relationships, revealing numerous potential anticancer molecules lay theoretical foundation traditional Chinese medicinal herbs creation new drugs.

Language: Английский

Citations

0

Cardenolides in Asclepias syriaca Seeds: Exploring the Legacy of Tadeus Reichstein DOI
Paola Rubiano-Buitrago, R. A. White,

Amy P. Hastings

et al.

Journal of Natural Products, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

The common milkweed Asclepias syriaca is widespread in North America and produces cardenolide toxins that deter herbivores by targeting the transmembrane enzyme Na+/K+-ATPase. In 1979, Nobel Laureate Tadeus Reichstein elucidated structure of novel cardenolides isolated from A. roots proposed structures for several other could not be confirmed. this study, we investigate composition seeds, focusing on their abundance vitro inhibitory potency sensitive porcine Na+/K+-ATPase highly resistant large bug, Oncopeltus fasciatus. We identify five previously unreported (1–5), three which are predominantly found addition to known syrioside (6), aspecioside (7), 2-thiazoline ring-containing labriformin (8). Glucopyranosyl-allomethylosyl-12-deoxy (5) distinguished lack oxidation at C-12, compounds 2, 3, 6, 8 contain a rare 1,4-dioxane motif. Inhibitory efficacy enzymes appears correlated. Finally, confirmed compound originally Reichstein, pleased share his original 1979 handwritten manuscript.

Language: Английский

Citations

0

Cardenolides in the defensive fluid of adult large milkweed bugs have differential potency on vertebrate and invertebrate predator Na+/K+¬–ATPases DOI Open Access
Paola Rubiano-Buitrago, Shrikant Pradhan, Alfonso Aceves‐Aparicio

et al.

Authorea (Authorea), Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 6, 2023

The defences of aposematic animals are characterised by diversity and variability secondary metabolites. Here we examine the nature function chemical defence in large milkweed bugs, Oncopeltus fasciatus, testing hypothesis that different compounds have evolved response to enemies. We profiled quantified cardenolides sequestered bugs their defensive secretions bodies, measured inhibitory properties a subset isolated insect’s against Na+/K+—ATPase target site vertebrate invertebrate predators, using porcine data as reference. show highly concentrated coroglaucigenin (glucopyranosyl frugoside frugoside) toxic for both resistant sensitive whereas corotoxigenin calotropagenin varying degrees enzyme inhibition among various predators. Overall, O. fasciatus is well defended range enemies due differential effect these compounds´ sites. Our results suggest insect sequester predation pressure.

Language: Английский

Citations

0