Dose-dependent alkaloid sequestration and N-methylation of decahydroquinoline in poison frogs.

Sequestration of chemical defenses from dietary sources is dependent on the availability of compounds in the environment and the mechanism of sequestration. Previous experiments have shown that sequestration efficiency varies among alkaloids in poison frogs, but little is known about the underlying mechanism. The aim of this study was to quantify the extent to which alkaloid sequestration and modification are dependent on alkaloid availability and/or sequestration mechanism. To do this, we administered different doses of histrionicotoxin (HTX) 235A and decahydroquinoline (DHQ) to captive-bred Adelphobates galactonotus and measured alkaloid quantity in muscle, kidney, liver, and feces. HTX 235A and DHQ were detected in all organs, whereas only DHQ was present in trace amounts in feces. For both liver and skin, the quantity of alkaloid accumulated increased at higher doses for both alkaloids. Accumulation efficiency in the skin increased at higher doses for HTX 235A but remained constant for DHQ. In contrast, the efficiency of HTX 235A accumulation in the liver was inversely related to dose and a similar, albeit statistically nonsignificant, pattern was observed for DHQ. We identified and quantified the N-methylation of DHQ in A. galactonotus, which represents a previously unknown example of alkaloid modification in poison frogs. Our study suggests that variation in alkaloid composition among individuals and species can result from differences in sequestration efficiency related to the type and amount of alkaloids available in the environment.

Dose-dependent alkaloid sequestration and N-methylation of decahydroquinoline in poison frogs

Sequestration of chemical defenses from dietary sources is dependent on the availability of compounds in the environment and the mechanism of sequestration. Previous experiments have shown that sequestration efficiency varies among alkaloids in poison frogs, but little is known about the underlying mechanism. The aim of this study was to quantify the extent to which alkaloid sequestration and modification are dependent on alkaloid availability and/or sequestration mechanism. To do this, we administered different doses of histrionicotoxin (HTX) 235A and decahydroquinoline (DHQ) to captive-bred Adelphobates galactonotus and measured alkaloid quantity in muscle, kidney, liver, and feces. HTX 235A and DHQ were detected in all organs, whereas only DHQ was present in trace amounts in feces. For both liver and skin, the quantity of alkaloid accumulated increased at higher doses for both alkaloids. Accumulation efficiency in the skin increased at higher doses for HTX 235A but remained constant for DHQ. In contrast, the efficiency of HTX 235A accumulation in the liver was inversely related to dose and a similar, albeit statistically nonsignificant, pattern was observed for DHQ. We identified and quantified the N-methylation of DHQ in A. galactonotus, which represents a previously unknown example of alkaloid modification in poison frogs. Our study suggests that variation in alkaloid composition among individuals and species can result from differences in sequestration efficiency related to the type and amount of alkaloids available in the environment.

Use of whole-body cryosectioning and desorption electrospray ionization mass spectrometry imaging to visualize alkaloid distribution in poison frogs.

Ambient mass spectrometry is useful for analyzing compounds that would be affected by other chemical procedures. Poison frogs are known to sequester alkaloids from their diet, but the sequestration pathway is unknown. Here, we describe methods for whole-body cryosectioning of frogs and use desorption electrospray ionization mass spectrometry imaging (DESI-MSI) to map the orally administered alkaloid histrionicotoxin 235A in a whole-body section of the poison frog Dendrobates tinctorius. Our results show that whole-body cryosectioning coupled with histochemical staining and DESI-MSI is an effective technique to visualize alkaloid distribution and help elucidate the mechanisms involved in alkaloid sequestration in poison frogs.

[Biological activity tests of chemical constituents from two Brazilian Labiatae plants].

We studied the bioactivities of constituents from two tropical medicinal plants, Cunila spicata and Hyptis fasciculata. These plants found in Brazil belong to the Labiatae family. Four known compounds obtained from these herbs were identified as 3alpha, 24-dihydoxylurs-12-en-28-oic acid, betulinic acid, aurantiamide acetate, and aurantiamide benzoate by spectroscopic means. 3alpha, 24-Dihydoxylurs-12-en-28-oic acid has potent inhibitory activity against Streptococcus salivarius, Streptococcus pneumoniae, Streptococcus pyogenes, and Porphyromomas gingivalis. Aurantiamide benzoate exhibited moderate inhibitory activity against xanthine oxidase. It was clarified that herbs Cunila spicata and Hyptis fasciculata are effective against bronchitis and gout.

The anti-Helicobacter pylori flavones in a Brazilian plant, Hyptis fasciculata, and the activity of methoxyflavones.

Two known flavonoids were isolated from a tropical medicinal plant, Hyptis fasciculata (Labiatae), found in Brazil. Flavonoids were identified as cirsilineol (1) and cirsimaritin (2) by spectroscopic means and were exhibited potent antibacterial activity against Helicobacter pylori, and cirsilineol (1) had weak antibacterial activity against Escherichia coli and Salmonella enteritidis. Following up on the relationship between anti-H. pylori activity and flavonoids with methoxy groups, several methoxy flavonoids were evaluated for proliferation of H. pylori.