Screening the Efficacy and Safety of Molluscicides from Three Leaf Extracts of Chimonanthus against the Invasive Apple Snail, Pomacea canaliculata.

Pomacea canaliculata, the invasive snail, is a host of the parasitic nematode Angiostrongylus cantonensis, which has adverse effects on the agriculture system and human health. This work evaluated the molluscicidal activity of petroleum ether extracts (PEEs) from three species of Chimonanthus against the snail P. canaliculate. Pcp (PEE of C. praecox) showed the most effective molluscicide activity. Sixty-one compounds were identified by GC-MS and the main components were terpenoids and fatty acids. The half-lethal concentration (LC50) of Pcp at 24 h (0.27 mg/mL) and 48 h (0.19 mg/mL) was used to evaluate the biochemical alterations in snail tissue. These sublethal concentrations caused the levels of alkaline phosphatase (ALP), alanine aminotransferase (ALT), and aspartate aminotransferase (AST) activity to increase, while acetylcholinesterase (AChE) activity decreased. Also, under LC50 treatment, several histological changes were observed in the hepatopancreas and foot of the snail compared with the control group. Moreover, the toxic test in rice demonstrated that Pcp has low toxicity. These results suggest that Pcp could be developed as an effective molluscicide for P. canaliculata control.

Design, Synthesis, Characterization, and Molluscicidal Activity Screening of New Nicotinonitrile Derivatives against Land Snails, M. cartusiana.

A new series of nicotinonitrile derivatives 2-7 was designed and synthesized from the starting material (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one (1) to assess their molluscicidal activity. The newly synthesized nicotinonitrile compounds 2-7 were characterized based on FTIR, 1H-NMR, and 13C-APT NMR spectra as well as elemental microanalyses. The target compounds 2-7 were screened for their toxicity effect against M. cartusiana land snails and were compared to Acetamiprid as a reference compound. The results demonstrated that the nicotinonitrile-2-thiolate salts 4a and 4b had good mortality compared with that of Acetamiprid. The results of the in vivo effect of the prepared nicotinonitrile molecules 2, 4a, and 4b on biochemical parameters, including AChE, ALT, AST, and TSP, indicated a reduction in the level of AChE and TSP as well as an increase in the concentration of transaminases (ALT and AST). A histopathological study of the digestive gland sections of the M. cartusiana land snails was carried out. The nicotinonitrile-2-thiolate salts 4a,b showed vacuolization, causing the digestive gland to lose its function. It could be concluded that the water-soluble nicotinonitrile-2-thiolate salts 4a,b could be adequate molluscicidal molecules against M. cartusiana land snails.

Lantana camara Essential Oils from Vietnam: Chemical Composition, Molluscicidal, and Mosquito Larvicidal Activity.

Lantana camara is a troublesome invasive plant introduced to many tropical regions, including Southeast Asia. However, the plant does hold promise as a source of essential oils that may be explored for potential use. Fresh water snails such as Pomacea canaliculata, Gyraulus convexiusculus, and Tarebia granifera can be problematic agricultural pests as well as hosts for parasitic worms. Aedes and Culex mosquitoes are notorious vectors of numerous viral pathogens. Control of these vectors is of utmost importance. In this work, the essential oil compositions, molluscicidal, and mosquito larvicidal activities of four collections of L. camara from north-central Vietnam have been investigated. The sesquiterpene-rich L. camara essential oils showed wide variation in their compositions, not only compared to essential oils from other geographical locations (at least six possible chemotypes), but also between the four samples from Vietnam. L. camara essential oils showed molluscicidal activities comparable to the positive control, tea saponin, as well as other botanical agents. The median lethal concentrations (LC50 ) against the snails were 23.6-40.2 µg/mL (P. canaliculata), 7.9-29.6 µg/mL (G. convexiusculus), and 15.0-29.6 µg/mL (T. granifera). The essential oils showed good mosquito larvicidal activities with 24-h LC50 values of 15.1-29.0 µg/mL, 26.4-53.8 µg/mL, and 20.8-59.3 µg/mL against Ae. aegypti, Ae. albopictus, and Cx. quinquefasciatus, respectively. The essential oils were more toxic to snails and mosquito larvae than they were to the non-target water bug, Diplonychus rusticus (24-h LC50 =103.7-162.5 µg/mL). Sesquiterpene components of the essential oils may be acting as acetylcholinesterase (AChE) inhibitors. These results suggest that the invasive plant, L. camara, may be a renewable botanical pesticidal agent.

Review of Ethnomedicinal Uses, Phytochemistry and Pharmacological Properties of Euclea natalensis A.DC.

Euclea natalensis is traditionally used as herbal medicine for several human diseases and ailments in tropical Africa. This study reviews information on ethnomedicinal uses, botany, phytochemical constituents, pharmacology and toxicity of E. natalensis. Results of this study are based on literature search from several sources including electronic databases, books, book chapters, websites, theses and conference proceedings. This study showed that E. natalensis is used as traditional medicine in 57.1% of the countries where it is indigenous. Euclea natalensis has a high degree of consensus on abdominal pains, antidote for snake bites, diabetes, diarrhoea, malaria, roundworms, stomach problems, toothache, venereal diseases and wounds. Several ethnopharmacological studies have shown that crude extracts and chemical compounds from E. natalensis demonstrated many biological activities both in vitro and in vivo, which included antibacterial, antidiabetic, antifungal, antimycobacterial, antiviral, antioxidant, antiplasmodial, larvicidal, antischistosomal, molluscicidal, dentin permeability and hepatoprotective activities. Future studies should focus on the mechanism of biological activities of both crude extracts and chemical compounds from the species, as well as structure-function relationships of bioactive constituents of the species.

Barbatic Acid Offers a New Possibility for Control of Biomphalaria Glabrata and Schistosomiasis.

This study evaluated the biological activity of an ether extract and barbatic acid (BAR) from Cladia aggregata on embryos and adult mollusks of Biomphalaria glabrata, cercariae of Schistosoma mansoni and the microcrustacean Artemia salina. The ether extract and BAR were obtained by successive extractions with diethyl ether. The obtained extracts were analyzed using thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), proton nuclear magnetic resonance (¹H-NMR) and infrared (IR) spectroscopy. The results demonstrated that the ether extract exerted embryotoxic effects at 50 and 100 µg/mL and molluscicidal effects at 20 and 25 µg/mL. BAR exhibited no embryotoxicity, and its molluscicidal concentration was equal to that of the ether extract. However, after 60 min of exposure, 1 µg/mL BAR presented cercaricidal activity against the parasite S. mansoni at the second larval stage. Neither substance induced toxicity against A. salina. These results indicate the potential molluscicidal activities of the ether extract and BAR against B. glabrata and S. mansoni cercariae. In addition to these effects, there was a lack of toxicity against the aquatic environment and no damage to the biota, indicating the potential of these products for large-scale control and/or eradication of schistosomiasis.

Acacetin-7-rutinoside from Buddleja lindleyana, a new molluscicidal agent against Oncomelania hupensis.

Buddleja lindleyana is a medicinally important member of the family Loganiaceae distributed in Eastern China. The plant has been used in different traditional medications for the treatment of various diseases. Acacetin-7-rutinoside was isolated from the n-butanol fraction of fresh B. lindleyana leaves and found to be a new molluscicidal agent against the snail Oncomelania hupensis. The structure of acacetin-7-rutinoside was elucidated based on spectral data, including 1H NMR and 13C NMR.

Molluscicidal and leishmanicidal activity of the leaf essential oil of Syzygium cumini (L.) SKEELS from Brazil.

The chemical composition and biological potential of the essential oil extracted from Syzygium cumini leaves collected in Brazil were examined. GC/MS Analyses revealed a high abundance of monoterpenes (87.12%) in the oil. Eleven compounds were identified, with the major components being α-pinene (31.85%), (Z)-ß-ocimene (28.98%), and (E)-ß-ocimene (11.71%). To evaluate the molluscicidal effect of the oil, it was tested against Biomphalaria glabrata and the LC50 obtained was 90 mg/l. The essential oil also showed significant activity against Leishmania amazonensis, with an IC50 value equal to 60 mg/l. In addition, to evaluate its toxicity towards a non-target organism, the essential oil was tested against Artemia salina and showed a LC50 of 175 mg/l. Thus, the essential oil of S. cumini showed promising activity as a molluscicidal and leishmanicidal agent and might be valuable in combating neglected tropical diseases such as schistosomiasis and leishmaniasis. Further research is being conducted with regard to the purification and isolation of the most active essential-oil compounds.

Molluscicidal and larvicidal activities and essential oil composition of Cymbopogon winterianus.

UNLABELLED: CONTEXT. Cymbopogon winterianus Jowitt ex Bor (Poaceae), known as citronella grass, is an aromatic herbaceous plant and the essential oil extracted from this grass is used in cosmetics, perfumes, hygiene and cleanliness products worldwide. OBJECTIVE: This study investigated the composition and molluscicidal and larvicidal activities of the essential oil of C. winterianus cultivated in North Brazil. MATERIALS AND METHODS: The oil was obtained by hydrodistillation, analyzed by gas chromatography (GC) and GC-mass spectrometry and then its molluscicidal and larvicidal activities against snails (Biomphalaria glabrata) and hatched larvae of Artemia salina, respectively, were evaluated at concentrations from 10 to 1000 mg/L. RESULTS: The main constituents of oil were citronellal (26.5%), geraniol (16.2%), elemol (14.5%) and citronellol (7.3%). The molluscicidal test revealed significant lethal concentration (LC) values (LC90=97.0 mg/L, LC50=54.0 mg/L and LC20=22.0 mg/L), indicating the presence of molluscicidal compounds in the oil. In addition, the oil showed moderate larvicidal activity (LC50=181.0 mg/L) against the larvae of A. salina, which could justify its use in the aquatic environment without affecting other living organisms. DISCUSSION AND CONCLUSION: The results suggest that the oil of C. winterianus could be an effective alternative to control schistosomiasis, with an average margin of safety to other living organisms that coexist with snails.

Molluscicidal activity of Balanites aegyptiaca against Monacha cartusiana.

CONTEXT: Balanites aegyptiaca (L.) Delile (Zygophyllaceae) is a tropical tree that has many folk uses in various countries. The bark extract is used for the control of the fresh water snails that act as intermediary host of Schistosoma. OBJECTIVE: Study the molluscicidal activity and chemical constituents of seed oil and seed glycosides of B. aegyptiaca against Monacha cartusiana and determine the structure-activity relationship. MATERIALS AND METHODS: Two bioassay methods (residual film application and the leaf dipping technique) were used to evaluate the toxicity effect of the seed oil and glycosides, in concentrations of 1.000, 0.500, 0.250 and 0.125%. The seed oil was analysed by GC/MS. Acid hydrolysis and chromatographic separation were used to study the seed saponins. RESULTS: The bioassay of B. aegyptiaca against the land snail, M. cartusiana, indicated the activity of the seed oil and the high activity of the seed saponins. The seed glycosides gave 30.0, 53.3, 73.0 and 73.3% mortality for concentrations of 0.125, 0.250, 0.500 and 1.00%, respectively. The LC(50) values were 0.335 and 0.256%, respectively. The seed oil was analysed by GC/MS. Acid hydrolysis of the seed saponins gave a mixture of diosgenin, yamogenin and 3,5-spirostadiene. DISCUSSION AND CONCLUSION: To study the structure-activity relationship, a triterpenoidal saponin and a triterpenoidal saponins rich extract (of Zygophyllum coccenum) were proven to be inactive. Thus, the activity is associated with the steroidal, not triterpenoidal saponins. Moreover, a spirostane aglycone without sugar moiety, was found to be inactive and attained the activity by glycosidation.

Molluscicidal and cercaricidal activities of the essential oil of Dysphania ambrosioides (L.) Mosyakin & Clemants: Implications for the control of schistosomiasis.

Schistosomiasis is one of the most important tropical diseases. A fundamental strategy to control its spread is the use of natural products against its vectors, which are snails of the genus Biomphalaria. The present study evaluated the chemical composition, the molluscicidal and cercaricidal effects, and the ecotoxicity of the essential oil from the aerial parts of Dysphania ambrosioides (L.) Mosyakin & Clemants (DAEO). The essential oil was obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS). Molluscicidal and cercaricidal activities were determined by the immersion method. Environmental toxicity was assessed from bioassays using Artemia salina larvae and Danio rerio fish. DAEO presented a 0.8% yield. The GC-MS analysis revealed the predominance of hydrocarbon monoterpenes in the oil. A total of 32 constituents was identified, with α-terpinene (50.69%) being the major compound, followed by p-cymene (13.27%) and ascaridole (10.26%). DAEO was active against adult Biomphalaria glabrata snails and demonstrated lethal effect against Schistosoma mansoni cercariae, with LC50 values of 25.2 (22.7-27.8) and 62.4 (61.8-62.9) µg/mL, respectively. Regarding toxicity to non-target aquatic organisms, the oil showed LC50 values of 86.9 (84.7-87.6) and 18.6 µg/mL (15.5-22.8) for A. salina and D. rerio, respectively. DAEO proved to be a promising natural product for the control of schistosomiasis, acting on both the vectors and the etiological agent of the disease. However, the use of the oil is safer in transmission sites where there are no non-target organisms, as it has showed toxicity to D. rerio fish.

Synthesis of molluscicidal agent cyanolide a macrolactone from D-(-)-pantolactone.

An efficient synthesis of potent molluscicidal agent cyanolide A, a glycosidic 16-membered macrolide, starting from D-(-)-pantolactone is reported. Highly stereoselective aldol, oxa-Michael addition, and Yamaguchi macrolactonization are the key steps in the present synthesis.

Molluscicidal metabolites from an assemblage of Palmyra Atoll cyanobacteria.

Molluscicides can play an important role in the control of schistosomiasis because snails of the genus Biomphalaria act as intermediate hosts for the parasite. Schistosomiasis is one of 13 neglected tropical diseases with high morbidity and mortality that collectively affect one billion of the world's poorest population, mainly in developing countries. Thiopalmyrone (1) and palmyrrolinone (2), metabolites isolated from extracts of a Palmyra Atoll environmental assemblage of two cyanobacteria, cf. Oscillatoria and Hormoscilla spp., represent new and potent molluscicidal chemotypes against Biomphalaria glabrata (LC50=8.3 and 6.0 µM, respectively). A slight enhancement in molluscicidal effect (LC50=5.0 µM) was observed when these two natural products were utilized as an equimolar binary mixture.

Residues and dissipation dynamics of molluscicide metaldehyde in cabbage and soil.

The dissipation of metaldehyde on cabbage and in soil was studied and half-life (DT(50)) was estimated in a field study carried out at three different locations. Metaldehyde was sprayed on cabbage at 937.5 and 1406.25 ga.i.ha(-1) for residue study and 1,875 ga.i.ha(-1) for dissipation study in cabbage and soil. Samples of cabbage and soil for dissipation experiment were collected at 0, 1, 2, 3, 5, 7, 14 and 21 days after treatment. For residue studies, cabbage and soil samples were sampled at 5, 7 and 10 days after treatment. Quantification of residues was done by LC-MS/MS. The DT(50) of metaldehyde in cabbage and soil were 0.48-1.61 days and 0.75-1.02 days, respectively, when applied at 2 times of the recommended high dosage. Residues of metaldehyde in cabbage were all below the maximum residue levels of 1.0 mg kg(-1) at both recommended high dosage and 1.5 times the recommended high dosage.

Application of nanotized formulation in the control of snail intermediate hosts of schistosomes.

Schistosomiasis continues to pose significant public health problems in many developing countries. Mass drug administration (MDA) is the most adopted control option but there is increasing evidence for the development of praziquantel-resistant Schistosoma strains. This shortcoming has necessitated the search for other effective methods for the control of schistosomiasis. The breaking of Schistosoma transmission cycles through the application of molluscicides into snail infested freshwater bodies has yielded positive outcomes when integrated with MDA in some countries. However, few of such effective molluscicides are currently available, and where available, their application is restricted due to toxicity concerns. Some nanotized particles with molluscicidal activities against the different stages of snail intermediate hosts of schistosomes have been reported. Importantly, the curcumin-nisin nanoparticle synthesized by our group was very effective and it showed no significant toxicity in a mouse model and brine shrimps. This, therefore, offers the possibility of developing a molluscicide that is not only safe for man but also is environmentally friendly. This paper reviews nanoparticles with molluscicidal potential. The methods of their formulation, activities, probable mechanisms of actions, and their toxicity profiles are discussed. More research should be made in this field as it offers great potential for the development of new molluscicides.

Phloroglucinols from the argentine ferns Elaphoglossum gayanum and E. piloselloides.

Five new prenylated phloroglucinols were isolated from the diethyl ether extracts of the ferns Elaphoglossum gayanum and E. piloselloides. Their structures were established by analysis of their spectroscopic data (1D and 2D NMR, HRMS, and IR) and chemical derivatization. The two major compounds exhibited moderate molluscicidal activity against the snail Biomphalaria peregrina, a vector of the tropical disease schistosomiasis, with LD(50) 7.2 microg/mL (14.4 microM) and 11.7 microg/mL (22.2 microM).

Cyanolide A, a glycosidic macrolide with potent Molluscicidal activity from the Papua New Guinea cyanobacterium Lyngbya bouillonii.

Over the last 50 years, molluscicides have played a critical role in the control of schistosomiasis transmission. Cyanolide A (2), isolated from extracts of a Papua New Guinea collection of Lyngbya bouillonii, is a new and highly potent molluscicidal agent against the snail vector Biomphalaria glabrata (LC(50) = 1.2 microM). The structure of cyanolide A (2) was elucidated through extensive NMR spectroscopic analyses, yielding a symmetrical dimer that represents the newest addition to the family of glycosidic macrolides from cyanobacteria.

Behavioural responses of the snail Lymnaea acuminata to carbohydrates and amino acids in bait pellets.

Snail control could play an important role in programmes against fascioliasis, especially if the methods used for molluscicide delivery could be improved, such as by the development of bait formulations containing both an effective attractant and a molluscicide, to ensure good levels of contact between the molluscicide and the target snail populations. In a recent study, the attractiveness to Lymnaea acuminata (an intermediate host of the digenean trematode Fasciola gigantica) of potential components of snail-attractant pellets was investigated. Carbohydrates (glucose, maltose, sucrose or starch, each at 10 mM) and amino acids (citrulline, tryptophan, proline or serine, each at 20 mM), were tested in aquaria, with the snails initially placed 22.5, 30 or 45 cm from an agar pellet containing the component under test. Under these conditions, starch and proline emerged as the strongest attractants for L. acuminata, followed by maltose and serine.

Molluscicides from some common medicinal plants of eastern Uttar Pradesh, India.

Many aquatic snails act as intermediate hosts for the larvae of trematodes, Fasciola hepatica and Fasciola gigantica, which cause the diseases fascioliasis and schistosomiasis. The WHO has tested several thousands of synthetic compounds for the control of the snail host. Although effective, these molluscicides have so far not proved themselves to be entirely satisfactory. With a growing awareness of environmental pollution, efforts are being made to discover molluscicidal products of plant origin. Being products of biosynthesis, these are potentially biodegradable in nature. Several groups of compounds present in various plants have been found to be toxic to target organisms at acceptable doses ranging from <1 to 100 ppm. Common medicinal plants, i.e. Thevetia peruviana, Alstonia scholaris (Family; Apocynaceae), Euphorbia pulcherima and Euphorbia hirta (Family; Euphorbiaceae), have potent molluscicidal activity against freshwater snails. The toxicological actions of Thevetia peruviana may be due to the presence of apigenin-5-methyl ether (flavonoid) and triterpenoid glycosides, while a number of alkaloids (pseudo-akuammigine in addition to betulin, ursolic acid and beta-sitosterol), steroids and triterpenoids are present in Alstonia scholaris and the diterpenoids, pulcherrol, beta-sitosterol, hentriacontane, ellagic acid and beta-amyrin are present in Euphorbia hirta and in Euphorbia pulcherima. Although, at present very little literature is available on the control of vector snails through plant origin pesticides, an attempt has been made in this review to assemble all the known information on molluscicidal properties of common medicinal plants of eastern Uttar Pradesh, India, which might be useful for the control of harmful snails.

[Study on the factors affecting the degradation of niclosamide in the soil].

OBJECTIVE: To investigate the factors affecting the degradation of niclosamide in the soil, so as to provide the evidence for the assessment of the environmental safety in the field snail control with niclosamide. METHODS: A high performance liquid chromatography was established for the determination of niclosamide in the field. Then, the degradation of niclosamide was investigated in soils with different moistures (10%, 30%, 50%, 70% and 90%), temperatures [(15 ± 1), (25 ± 1), (35 ± 1) °C], initial concentrations (1, 5, 10 mg/kg) and in sterilized and non-sterilized soils. In addition, the degradation of niclosamide was fitted with the first-order kinetics equation, and the degradation half-life was calculated. RESULTS: The niclosamide residues gradually decreased over time in soils with different moistures, and a higher rate of degradation was seen in soils with a higher moisture. The degradation half-life of niclosamide reduced from 4.258 d in the soil with a 10% moisture to 2.412 d in the soil with a 90% moisture. The niclosamide residues gradually decreased over time in soils with different temperatures, and a higher rate of degradation was seen in soils with a higher temperature. The degradation half-life of niclosamide reduced from 4.398 d in the soil with a temperature of (15 ± 1) °C to 2.828 d in the soil with a temperature of (35 ± 1) °C. The degradation half-lives of niclosamide were 3.212, 3.333 d and 3.448 d in soils containing niclosamide at initial concentrations of 1, 5 mg/kg and 10 mg/kg, and > 30 d and 3.273 d in sterilized and non-sterilized soils. Multiple linear regression analysis revealed that soil microorganisms (P = 0.010), moisture (P = 0.000) and temperature (P = 0.002) affected the half-life of niclosamide degradation. CONCLUSIONS: The degradation of niclosamide in soils fits the first-order kinetics equation, and presence of microorganisms, a high temperature and high moisture may accelerate the degradation of niclosamide in the soil.

Molluscicidal activity of polyvinylpyrrolidone (PVP)-functionalized silver nanoparticles to Biomphalaria glabrata: Implications for control of intermediate host snail of Schistosoma mansoni.

Silver nanoparticles (Ag NPs) have been applied in several commercial products due to their antimicrobial properties, while their molluscicide properties, mode of action and toxicity to snail species remain unclear. In this study, the comparative toxicity of polyvinylpyrrolidone (PVP)-functionalized Ag NPs and their dissolved counterpart (Ag ions) was analyzed during the early developmental stages of the freshwater snail Biomphalaria glabrata, intermediate host of Schistosoma mansoni. Ag NPs were synthesized and characterized by multiple techniques, and the snail embryotoxicity was analyzed in terms of mortality, hatching, developmental stages and morphological alterations, while the acute toxicity to newly-hatched snails was analyzed by mortality and behavioral impairments. Results showed that both Ag forms induced mortality, hatching delay and morphological alterations (especially hydropic abnormalities) in snail embryos in a concentration and exposure time dependent patterns. Ag NPs showed low embryotoxic effects and similar toxicity for newly-hatched snails when compared to their dissolved counterparts, indicating that the nanotoxicity was dependent of snail developmental stages. The knowledge about the Ag NP toxicity to different early development stages of B. glabrata contributes to its potential use as molluscicide and control of neglected tropical diseases, including schistosomiasis.