“…Palasonin is the first CRC that has been so far recorded from the meloids. Dettner et al (6) were the first who reported palasonin from the South African blister beetle,…”
Cantharidin is mainly found in the beetle families Meloidae and Oedemeridae (Insecta: Coleoptera) which are the natural producers of this terpene anhydride. Most studies to date have focused on cantharidin distribution in blister beetles, with few reports on recently found cantharidin-related compounds (CRCs). Using gas chromatography-mass spectrometry (GC-MS), the present work reported cantharidin and two CRCs, palasonin and cantharidinimide from Mylabris impressa stillata (Baudi, 1878) which was collected from Toyserkan county, Hamedan Province, Iran. Ionization provided mass spectra with characteristic fragments of cantharidin at m/z 96 and 128, demethylcantharidin at m/z 82 and 114, and cantharidinimide at m/z 70, 96 and 127. This is the first time that cantharidin and the two CRCs are found in the genus Mylabris which in turn is new to the field of venomous insects
“…Palasonin is the first CRC that has been so far recorded from the meloids. Dettner et al (6) were the first who reported palasonin from the South African blister beetle,…”
Cantharidin is mainly found in the beetle families Meloidae and Oedemeridae (Insecta: Coleoptera) which are the natural producers of this terpene anhydride. Most studies to date have focused on cantharidin distribution in blister beetles, with few reports on recently found cantharidin-related compounds (CRCs). Using gas chromatography-mass spectrometry (GC-MS), the present work reported cantharidin and two CRCs, palasonin and cantharidinimide from Mylabris impressa stillata (Baudi, 1878) which was collected from Toyserkan county, Hamedan Province, Iran. Ionization provided mass spectra with characteristic fragments of cantharidin at m/z 96 and 128, demethylcantharidin at m/z 82 and 114, and cantharidinimide at m/z 70, 96 and 127. This is the first time that cantharidin and the two CRCs are found in the genus Mylabris which in turn is new to the field of venomous insects
“…The demethylated CTD analogue, ( R )-(+)-palasonin ( 50 ), was discovered in the dried bodies of the South African Hycleus oculatus , H. tinctus , and H. lunata beetles and is the only CTD analogue found in plant species as well39, 103, 104. Imide analogues of CTD and palasonin, cantharimide ( 51 ) and palasonimide ( 52 ) respectively, in which the oxygen atom in the anhydride core of the molecules is replaced by a nitrogen atom were also found in the H. lunata beetle 104 . Within the last decade cantharimide, 5-hydroxy cantharimide ( 53 ) and norcantharidin (NCTD, 54 ) were isolated from the native Korean and Chinese blister beetle, Mylabris phalerate PALLAS 39 .Figure 9Structures of monoterpene cantharidin (CTD), norcantharidin (NCTD), and their derivatives isolated from African, Korean, and Chinese Beetles.…”
Section: Coleoptera (Beetles)mentioning
confidence: 99%
“…9 ), was the first to be isolated and characterized ( c. 1914) from blister beetles colloquially known as the ‘Spanish fly’ 39 , 46 , 88 . The demethylated CTD analogue, ( R )-(+)-palasonin ( 50 ), was discovered in the dried bodies of the South African Hycleus oculatus , H. tinctus , and H. lunata beetles and is the only CTD analogue found in plant species as well 39 , 103 , 104 . Imide analogues of CTD and palasonin, cantharimide ( 51 ) and palasonimide ( 52 ) respectively, in which the oxygen atom in the anhydride core of the molecules is replaced by a nitrogen atom were also found in the H. lunata beetle 104 .…”
Nature has been the source of life-changing and -saving medications for centuries. Aspirin, penicillin and morphine are prime examples of Nature׳s gifts to medicine. These discoveries catalyzed the field of natural product drug discovery which has mostly focused on plants. However, insects have more than twice the number of species and entomotherapy has been in practice for as long as and often in conjunction with medicinal plants and is an important alternative to modern medicine in many parts of the world. Herein, an overview of current traditional medicinal applications of insects and characterization of isolated biologically active molecules starting from approximately 2010 is presented. Insect natural products reviewed were isolated from ants, bees, wasps, beetles, cockroaches, termites, flies, true bugs, moths and more. Biological activities of these natural products from insects include antimicrobial, antifungal, antiviral, anticancer, antioxidant, anti-inflammatory and immunomodulatory effects.
“…The identification was based on the spectra from the NIST library (NIST Mass Spectrometry, 2007), and the previous studies (20,21). Cantharidin (98% purity, CAS 56-25-7) were supplied by Sigma, but palasonin (C 9 H 9 O 4 ), palasoninimide (C 9 H 10 O 3 N), cantharidinimide (C 10 H 13 O 3 N) and D 2 C (C 10 H 10 D 2 O 4 ) were synthesized in the lab (see acknowledgements).…”
Section: Chemical Characterizationmentioning
confidence: 99%
“…This provides further evidence that females are able to actively synthesize palasonin. It has been indicated that unlike the plant source, insect-derived palasonin has a low enantiomeric excess (ee), with the (R)-(+)-enantiomer prevailing (30); therefore, palasonin uptake from hitherto unknown plant sources seems highly unlikely (21).…”
Cantharidin provides chemical protection for the coleopteran families Meloidae and Oedemeridae. In the present study, it was observed that cantharidin concentration in Hycleus scabiosae was slightly decreased from mated females (mean = 0.011 mg/mg of dry weight) to males (mean = 0.010 mg/mg) and considerably diminished in relation to virgin females (mean = 0.005 mg/mg). Significant concentrations of palasonin (21.69 ng/mg among virgins and 17.49 ng/mg in mated females) and palasoninimide (14.62 ng/ mg in virgins and 9.17 ng/mg in mated females) were found in H. scabiosae. Palasonin, palasoninimide and cantharidinimide content of eggs were measured as 5.61, 7.69 and 7.80 ng/mg respectively. Surprisingly, males showed no trace of cantharidin-related compounds (CRCs); therefore CRCs in H. scabiosae could not be transferred from males to females and based on experiments employing its deuterated form, cantharidin is probably independently synthesized in females from the male nuptial transfer. An inseminated female incorporates about 38.5 ng of cantharidin (0.34% of the maternal content), 196.35 ng of palasonin (91.82% of maternal content) and 269.15 ng of palasoninimide (96.70% maternal content) into each egg mass during oviposition. It seems that eggs of this meloid species exploit a different array of protective chemicals by increasing the ratio of CRCs versus cantharidin. CRCs are less toxic than cantharidin; therefore, such compounds might have been deposited in eggs as a safer substitute for cantharidin to provide effective protection, but does not simultaneously harm the susceptible embryo.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
