scholarly journals Two New Indole Alkaloids from Toad Venom of Bufo bufo gargarizans

Molecules ◽  
2020 ◽  
Vol 25 (19) ◽  
pp. 4511
Author(s):  
Yu-Lin Chen ◽  
Ying-Hui Dai ◽  
An-Dong Wang ◽  
Zi-Ying Zhou ◽  
Miao Lei ◽  
...  
Keyword(s):  
Malignant Melanoma ◽  
Indole Alkaloids ◽  
Water Extract ◽  
Bufo Bufo ◽  
Spectroscopic Methods ◽  
Human Malignant Melanoma ◽  
Mtt Method ◽  
Bufo Gargarizans ◽  
Toad Venom ◽  
First Time

Two new indole alkaloids, Bufotenidine B (2) and Bufocarboline A (6), along with seven known indole alkaloids (1, 3–5, and 7–9) and three organic acids (10–12), were isolated from the water extract of toad venom. The structures of the new alkaloids were elucidated by extensive spectroscopic methods. The absolute configurations of 4, 6, and 8 were determined for the first time by electronic circular dichroism (ECD) calculations. The cytotoxic activity of all compounds was tested against human malignant melanoma cells A375 by the MTT method, and no antitumor activity was observed.

scholarly journals A New Indole Alkaloid from the Toad Venom of Bufo bufo gargarizans

Molecules ◽  
2016 ◽  
Vol 21 (3) ◽  
pp. 349 ◽  
Author(s):  
Ying-Hui Dai ◽  
Bo Shen ◽  
Ming-Yu Xia ◽  
An-Dong Wang ◽  
Yu-Lin Chen ◽  
...  
Keyword(s):  
Indole Alkaloid ◽  
Bufo Bufo ◽  
Bufo Gargarizans ◽  
Toad Venom

scholarly journals Bufadienolides from the Venom of Bufo Bufo gargarizans and Their Enzyme Inhibition Activities and Brine Shrimp Lethality

2018 ◽  
Vol 13 (7) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Jian Xiao ◽  
Xiang Zhao ◽  
Wan-Tong Zhong ◽  
Fu-Rong Jiao ◽  
Xiao-Ling Wang ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Brine Shrimp ◽  
Bufo Bufo ◽  
Positive Control ◽  
Single Crystal Diffraction ◽  
X Ray ◽  
Nmr Data ◽  
Bufo Gargarizans ◽  
First Time ◽  
Potent Inhibitory Activity

A new bufadienolide named dyscinobufotalin (1), along with twenty known bufadienolides (2–21) were isolated from the venom of Bufo bufo gargarizans. Their structures were elucidated by spectroscopic analysis. The absolute configuration of the new natural product 2 was determined by X-ray single crystal diffraction and the complete NMR data for 3 was delivered for the first time. Both compounds 4 and 8 showed comparable α-glucosidase inhibitory activity (IC50 values of 0.25 and 0.26 μM, respectively) to the positive control acarbose (IC50 value of 0.42 μM), and 5 displayed potent inhibitory activity on acetylcholinesterase with an IC50 value of 0.12 μM. Moreover, 5, 8 and 13 presented moderate toxicity against brine shrimp.

scholarly journals Two New Aristolochic Acid Analogues from the Roots of Aristolochia contorta with Significant Cytotoxic Activity

Molecules ◽  
2020 ◽  
Vol 26 (1) ◽  
pp. 44
Author(s):  
Hong-Jian Ji ◽  
Jia-Yuan Li ◽  
Shi-Fei Wu ◽  
Wen-Yong Wu ◽  
Chang-Liang Yao ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Aristolochic Acid ◽  
Spectroscopic Methods ◽  
Proximal Tubular Cells ◽  
Tubular Cells ◽  
Mtt Method ◽  
Structure Activity ◽  
Proximal Tubular ◽  
Aristolochia Contorta ◽  
First Time

Twelve compounds, including two new aristolochic acid analogues with a formyloxy moiety (9–10) and 10 known aristolochic acid derivates (1–8 and 11–12), were obtained from the roots of Aristolochiacontorta. Their structures were elucidated using extensive spectroscopic methods. Their cytotoxic activity in human proximal tubular cells HK-2 was evaluated by the MTT method, which has been widely used to assess cell viability. Among these molecules, compounds 3 and 9 were found to be more cytotoxic. Furthermore, molecular modeling was used to evaluate, for the first time, the interactions of compounds 3 and 9 with the target protein organic anionic transporter 1 (OAT1) that plays a key role in mediating aristolochic acid nephropathy. Structure–activity relationships are briefly discussed.

scholarly journals Comparative Analysis of Hydrophilic Ingredients in Toad Skin and Toad Venom Using the UHPLC-HR-MS/MS and UPLC-QqQ-MS/MS Methods Together with the Anti-Inflammatory Evaluation of Indolealkylamines

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 86 ◽  
Author(s):  
Yu Zhang ◽  
Bo Yuan ◽  
Norio Takagi ◽  
Hongjie Wang ◽  
Yanyan Zhou ◽  
...  
Keyword(s):  
Amino Acids ◽  
Zebrafish Embryo ◽  
Bufo Bufo ◽  
Toad Skin ◽  
Bufo Melanostictus ◽  
Bufo Gargarizans ◽  
Toad Venom ◽  
Quantitative Results ◽  
Anti Inflammatory ◽  
The Difference

Toad skin and toad venom, as two kinds of Chinese medicine, are prepared from Bufo bufo gargarizans Cantor and Bufo melanostictus Schneider. However, they display distinct properties in traditional application, and the hydrophilic ingredients are the possible distinguishing chemicals between them. In this work, 36 and 22 hydrophilic components were characterized from toad skin and venom, respectively, by UHPLC-HR-MS/MS, including amino acids, nucleosides, polypeptides, and indolealkylamines (IAAs). Among them, 15 compounds were unambiguously confirmed by comparison with standards. The CID-MS/MS fragmentation behaviors of seven indolealkylamine references were investigated to ascertain three types of structures. Subsequently, 11 high abundance contents of hydrophilic ingredients were determined from 11 batches of toad skin and 4 batches of toad venom by UPLC-QqQ-MS/MS. The quantitative results showed that the content of main IAAs in toad venom was much higher than in skin. In addition, the N-methyl serotonin (free IAA), bufothionine (combined IAA), and total IAAs sample were selected for anti-inflammatory evaluation in lipopolysaccharide (LPS) stimulated zebrafish embryo models. The obvious anti-inflammatory activities of IAAs were observed, especially for the free IAAs. This study illustrated IAAs were the main distinct hydrophilic components that probably lead to the difference between toad skin and toad venom in traditional applications.

scholarly journals Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4217
Author(s):  
Candelario Rodriguez ◽  
Roberto Ibáñez ◽  
Luis Mojica ◽  
Michelle Ng ◽  
Carmenza Spadafora ◽  
...  
Keyword(s):  
Vero Cells ◽  
Chemical Diversity ◽  
Hydroxyl Group ◽  
Antitrypanosomal Activity ◽  
The Family ◽  
Toad Venom ◽  
Skin Secretions ◽  
Pharmacological Potential ◽  
First Time ◽  
Mcf 7

Toads in the family Bufonidae contain bufadienolides in their venom, which are characterized by their chemical diversity and high pharmacological potential. American trypanosomiasis is a neglected disease that affects an estimated 8 million people in tropical and subtropical countries. In this research, we investigated the chemical composition and antitrypanosomal activity of toad venom from Rhinella alata collected in Panama. Structural determination using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy led to the identification of 10 bufadienolides. Compounds identified include the following: 16β-hydroxy-desacetyl-bufotalin-3-adipoyl-arginine ester (1), bufotalin (2), 16β-hydroxy-desacetyl-bufotalin-3-pimeloyl-arginine ester (3), bufotalin-3-pimeloyl-arginine ester (4), 16β-hydroxy-desacetyl-bufotalin-3-suberoyl-arginine ester (5), bufotalin-3-suberoyl-arginine ester (6), cinobufagin-3-adipoyl-arginine ester (7), cinobufagin-3-pimeloyl-arginine ester (8), cinobufagin-3-suberoyl-arginine ester (9), and cinobufagin (10). Among these, three new natural products, 1, 3, and 5, are described, and compounds 1–10 are reported for the first time in R. alata. The antitrypanosomal activity assessed in this study revealed that the presence of an arginyl-diacid attached to C-3, and a hydroxyl group at C-14 in the structure of bufadienolides that is important for their biological activity. Bufadienolides showed cytotoxic activity against epithelial kidney Vero cells; however, bufagins (2 and 10) displayed low mammalian cytotoxicity. Compounds 2 and 10 showed activity against the cancer cell lines MCF-7, NCI-H460, and SF-268.

Pseudogenized Amelogenin Reveals Early Tooth Loss in True Toads (Anura: Bufonidae)

2021 ◽  
Author(s):  
John Shaheen ◽  
Austin B Mudd ◽  
Thomas G H Diekwisch ◽  
John Abramyan
Keyword(s):  
Tooth Loss ◽  
Tooth Enamel ◽  
Synonymous Substitution ◽  
Bufo Bufo ◽  
Molecular Dating ◽  
Bufo Gargarizans ◽  
The Family ◽  
Synonymous Substitution Rates ◽  
Mandibular Teeth ◽  
Early Tooth Loss

Abstract Extant anurans (frogs and toads) exhibit reduced dentition, ranging from a lack of mandibular teeth to complete edentulation, as observed in the true toads of the family Bufonidae. The evolutionary timeline of these reductions remains vague due to a poor fossil record. Previous studies have demonstrated an association between the lack of teeth in edentulous vertebrates and the pseudogenization of the major tooth enamel gene amelogenin (AMEL) through accumulation of deleterious mutations and the disruption of its coding sequence. In the present study we have harnessed the pseudogenization of AMEL as a molecular dating tool to correlate loss of dentition with genomic mutation patterns during the rise of the family Bufonidae. Specifically, we have utilized AMEL pseudogenes in three members of the family as a tool to estimate the putative date of edentulation in true toads. Comparison of AMEL sequences from Rhinella marina, Bufo gargarizans and Bufo bufo, with nine extant, dentulous frogs, revealed mutations confirming AMEL inactivation in Bufonidae. AMEL pseudogenes in modern bufonids also exhibited remarkably high 86–93% sequence identity among each other, with only a slight increase in substitution rate and relaxation of selective pressure, in comparison to functional copies in other anurans. Moreover, using selection intensity estimates and synonymous substitution rates, analysis of functional and pseudogenized AMEL resulted in an estimated inactivation window of 46-60 MYA in the lineage leading to modern true toads, a timeline that coincides with the rise of the family Bufonidae.

Bufadienolides from the Eggs of the Toad Bufo bufo gargarizans and Their Antimelanoma Activities

2021 ◽  
Author(s):  
Shi-wen Zhou ◽  
Jing-yu Quan ◽  
Zi-wei Li ◽  
Ge Ye ◽  
Zhuo Shang ◽  
...  
Keyword(s):  
Bufo Bufo ◽  
Bufo Gargarizans ◽  
Toad Bufo ◽  
Toad Bufo Bufo
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