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88-785: 43 genera, see text Ithomiini is a butterfly tribe in the nymphalid subfamily Danainae . It is sometimes referred to as the tribe of clearwing butterflies or glasswing butterflies . Some authors consider the group to be a subfamily ( Ithomiinae ). These butterflies are exclusively Neotropical , found in humid forests from sea level to 3000 m, from Mexico to Argentina. There are around 370 species in some 40–45 genera. Ithomiines are unpalatable because their adults seek out and sequester pyrrolizidine alkaloids from plants that they visit, especially composite flowers ( Asteraceae ) and wilted borages ( Boraginaceae ). The slow-flying adults are Müllerian mimics of each other as well as of many other Lepidoptera. Henry Walter Bates referred to

176-445: A Boc (tert-Butoxycarbonyl) protected pyrrole molecule and use specific reaction for synthesis into the desired compound. PAs are commonly introduced into the body via oral ingestion through contaminated food or traditional medicine, notably borage leaf, comfrey and coltsfoot . It can readily form salts with nitrates, chlorides and sulphates, which facilitate the uptake in the gastrointestinal tract . After which they travel to

264-505: A chrysalis . When metamorphosis is complete, the pupal skin splits, the adult insect climbs out, expands its wings to dry, and flies off. Some butterflies, especially in the tropics, have several generations in a year, while others have a single generation, and a few in cold locations may take several years to pass through their entire life cycle. Butterflies are often polymorphic , and many species make use of camouflage , mimicry , and aposematism to evade their predators. Some, like

352-637: A diapause (resting) stage, and the hatching may take place only in spring. Some temperate region butterflies, such as the Camberwell beauty , lay their eggs in the spring and have them hatch in the summer. Butterfly larvae, or caterpillars, consume plant leaves and spend practically all of their time searching for and eating food. Although most caterpillars are herbivorous, a few species are predators : Spalgis epius eats scale insects , while lycaenids such as Liphyra brassolis are myrmecophilous , eating ant larvae. Some larvae, especially those of

440-526: A "transparency group" of Amazon butterfly species. It was originally with seven species belonging to six different genera. Reginald Punnett suggested 28 species of this peculiar facies are known, though some are excessively rare. The majority are ithomiines, but two species of the Danaine genus Lycorea , the pierine Dismorphia orise the swallow-tail Parides hahneli , and several species of diurnal moths belonging to different families also enter into

528-493: A butterfly cannot fly until the wings are unfolded. A newly emerged butterfly needs to spend some time inflating its wings with hemolymph and letting them dry, during which time it is extremely vulnerable to predators. The colourful patterns on many butterfly wings tell potential predators that they are toxic. Hence, the genetic basis of wing pattern formation can illuminate both the evolution of butterflies as well as their developmental biology . The colour of butterfly wings

616-570: A butterfly through metamorphosis has held great appeal to mankind. To transform from the miniature wings visible on the outside of the pupa into large structures usable for flight, the pupal wings undergo rapid mitosis and absorb a great deal of nutrients. If one wing is surgically removed early on, the other three will grow to a larger size. In the pupa, the wing forms a structure that becomes compressed from top to bottom and pleated from proximal to distal ends as it grows, so that it can rapidly be unfolded to its full adult size. Several boundaries seen in

704-417: A common family. In some species, such as the great spangled fritillary , the eggs are deposited close to but not on the food plant. This most likely happens when the egg overwinters before hatching and where the host plant loses its leaves in winter, as do violets in this example. The egg stage lasts a few weeks in most butterflies, but eggs laid close to winter, especially in temperate regions, go through

792-576: A few butterflies (e.g., harvesters ) eat harmful insects, and a few are predators of ants , while others live as mutualists in association with ants. Culturally, butterflies are a popular motif in the visual and literary arts. The Smithsonian Institution says "butterflies are certainly one of the most appealing creatures in nature". The Oxford English Dictionary derives the word straightforwardly from Old English butorflēoge , butter-fly; similar names in Old Dutch and Old High German show that

880-444: A few species. Some butterflies have organs of hearing and some species make stridulatory and clicking sounds. Many species of butterfly maintain territories and actively chase other species or individuals that may stray into them. Some species will bask or perch on chosen perches. The flight styles of butterflies are often characteristic and some species have courtship flight displays. Butterflies can only fly when their temperature

968-606: A hard-ridged outer layer of shell, called the chorion . This is lined with a thin coating of wax which prevents the egg from drying out before the larva has had time to fully develop. Each egg contains a number of tiny funnel-shaped openings at one end, called micropyles ; the purpose of these holes is to allow sperm to enter and fertilize the egg. Butterfly eggs vary greatly in size and shape between species, but are usually upright and finely sculptured. Some species lay eggs singly, others in batches. Many females produce between one hundred and two hundred eggs. Butterfly eggs are fixed to

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1056-508: A leaf before eggs are laid on it. Many butterflies use chemical signals, pheromones ; some have specialized scent scales ( androconia ) or other structures ( coremata or "hair pencils" in the Danaidae). Vision is well developed in butterflies and most species are sensitive to the ultraviolet spectrum. Many species show sexual dimorphism in the patterns of UV reflective patches. Colour vision may be widespread but has been demonstrated in only

1144-416: A leaf with a special glue which hardens rapidly. As it hardens it contracts, deforming the shape of the egg. This glue is easily seen surrounding the base of every egg forming a meniscus. The nature of the glue has been little researched but in the case of Pieris brassicae , it begins as a pale yellow granular secretion containing acidophilic proteins. This is viscous and darkens when exposed to air, becoming

1232-547: A longer lifespan of several months as adults. The thorax of the butterfly is devoted to locomotion. Each of the three thoracic segments has two legs (among nymphalids , the first pair is reduced and the insects walk on four legs). The second and third segments of the thorax bear the wings. The leading edges of the forewings have thick veins to strengthen them, and the hindwings are smaller and more rounded and have fewer stiffening veins. The forewings and hindwings are not hooked together ( as they are in moths ) but are coordinated by

1320-452: A necessity for their successful establishment. Many butterflies, such as the painted lady , monarch, and several danaine migrate for long distances. These migrations take place over a number of generations and no single individual completes the whole trip. The eastern North American population of monarchs can travel thousands of miles south-west to overwintering sites in Mexico . There is

1408-402: A nitrogen atom in the middle, and one or two carboxylic esters called necic acids. Four major necine bases are described, with retronecine and its enantiomer Heliotridine being the largest group, and highly toxic. Another group is the platynecine, the difference between these groups is its saturated base, which makes it less toxic. Most bases have a 1,2-unsaturated base. Another difference in

1496-658: A reverse migration in the spring. It has recently been shown that the British painted lady undertakes a 9,000-mile round trip in a series of steps by up to six successive generations, from tropical Africa to the Arctic Circle — almost double the length of the famous migrations undertaken by monarch. Spectacular large-scale migrations associated with the monsoon are seen in peninsular India. Migrations have been studied in more recent times using wing tags and also using stable hydrogen isotopes . Butterflies navigate using

1584-412: A segmented palp. Adjoining these is the labium-hypopharynx which houses a tubular spinneret which is able to extrude silk. Caterpillars such as those in the genus Calpodes (family Hesperiidae) have a specialized tracheal system on the 8th segment that function as a primitive lung. Butterfly caterpillars have three pairs of true legs on the thoracic segments and up to six pairs of prolegs arising from

1672-435: A silken girdle may be spun to keep the pupa in a head-up position. Most of the tissues and cells of the larva are broken down inside the pupa, as the constituent material is rebuilt into the imago. The structure of the transforming insect is visible from the exterior, with the wings folded flat on the ventral surface and the two halves of the proboscis, with the antennae and the legs between them. The pupal transformation into

1760-410: A time-compensated sun compass. They can see polarized light and therefore orient even in cloudy conditions. The polarized light near the ultraviolet spectrum appears to be particularly important. Many migratory butterflies live in semi-arid areas where breeding seasons are short. The life histories of their host plants also influence butterfly behaviour. Butterflies in their adult stage can live from

1848-541: A total of about 20,000 species. Traditionally, butterflies have been divided into the superfamilies Papilionoidea and the moth-like Hedyloidea . Recent work has discovered that Hedylidae, the only family within Hedyloidea, is nested within the Papilionoidea, meaning that Papilionoidea would be synonymous with Rhopalocera. The relationships between the rest of the 6 families are extremely well resolved, which

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1936-470: A trend towards multivoltinism . Courtship is often aerial and often involves pheromones . Butterflies then land on the ground or on a perch to mate. Copulation takes place tail-to-tail and may last from minutes to hours. Simple photoreceptor cells located at the genitals are important for this and other adult behaviours. The male passes a spermatophore to the female; to reduce sperm competition, he may cover her with his scent, or in some species such as

2024-486: A tubular proboscis which is curled up at rest and expanded when needed to feed. The first and second maxillae bear palps which function as sensory organs. Some species have a reduced proboscis or maxillary palps and do not feed as adults. Many Heliconius butterflies also use their proboscis to feed on pollen; in these species only 20% of the amino acids used in reproduction come from larval feeding, which allow them to develop more quickly as caterpillars, and gives them

2112-437: A water-insoluble, rubbery material which soon sets solid. Butterflies in the genus Agathymus do not fix their eggs to a leaf; instead, the newly laid eggs fall to the base of the plant. Eggs are almost invariably laid on plants. Each species of butterfly has its own host plant range and while some species of butterfly are restricted to just one species of plant, others use a range of plant species, often including members of

2200-422: A week to nearly a year depending on the species. Many species have long larval life stages while others can remain dormant in their pupal or egg stages and thereby survive winters. The Melissa Arctic ( Oeneis melissa ) overwinters twice as a caterpillar. Butterflies may have one or more broods per year. The number of generations per year varies from temperate to tropical regions with tropical regions showing

2288-450: Is above 27 °C (81 °F); when it is cool, they can position themselves to expose the underside of the wings to the sunlight to heat themselves up. If their body temperature reaches 40 °C (104 °F), they can orientate themselves with the folded wings edgewise to the sun. Basking is an activity which is more common in the cooler hours of the morning. Some species have evolved dark wingbases to help in gathering more heat and this

2376-458: Is derived from tiny structures called scales, each of which have their own pigments . In Heliconius butterflies, there are three types of scales: yellow/white, black, and red/orange/brown scales. Some mechanism of wing pattern formation are now being solved using genetic techniques. For instance, a gene called cortex determines the colour of scales: deleting cortex turned black and red scales yellow. Mutations, e.g. transposon insertions of

2464-403: Is especially evident in alpine forms. As in many other insects, the lift generated by butterflies is more than can be accounted for by steady-state, non-transitory aerodynamics . Studies using Vanessa atalanta in a wind tunnel show that they use a wide variety of aerodynamic mechanisms to generate force. These include wake capture , vortices at the wing edge, rotational mechanisms and

2552-419: Is exposed to PAs an effect can be seen on the foetus, mainly stillbirth and accumulation in the foetus. The main lethal responses in adult livestock exhibit necrosis, HSOS and megalacytosis . Additional to the short-term effect PAs have been found to lead to carcinogenic growths on the long term. The carcinogenic effect is caused by formation of DNA adducts, because of metabolic reactions. No minimum dosage for

2640-410: Is extruded and inserted into the female's vagina. A spermatophore is deposited in the female, following which the sperm make their way to a seminal receptacle where they are stored for later use. In both sexes, the genitalia are adorned with various spines, teeth, scales and bristles, which act to prevent the butterfly from mating with an insect of another species. After it emerges from its pupal stage,

2728-451: Is good, especially in some species in the blue/violet range. The antennae are composed of many segments and have clubbed tips (unlike moths that have tapering or feathery antennae). The sensory receptors are concentrated in the tips and can detect odours. Taste receptors are located on the palps and on the feet. The mouthparts are adapted to sucking and the mandibles are usually reduced in size or absent. The first maxillae are elongated into

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2816-581: Is native to the Americas, but in the nineteenth century or before, spread across the world, and is now found in Australia, New Zealand, other parts of Oceania, and the Iberian Peninsula . It is not clear how it dispersed; adults may have been blown by the wind or larvae or pupae may have been accidentally transported by humans, but the presence of suitable host plants in their new environment was

2904-465: Is restricted to the males, and studies have suggested that the nutrients collected may be provided as a nuptial gift , along with the spermatophore, during mating. In hilltopping , males of some species seek hilltops and ridge tops, which they patrol in search for females. Since it usually occurs in species with low population density, it is assumed these landscape points are used as meeting places to find mates. Butterflies use their antennae to sense

2992-493: Is shown by Xu. Genotoxicity is another consequence of PA metabolism. The reactive metabolites formed during PA metabolism can also bind to DNA , leading to the formation of DNA adducts. These adducts can induce mutations and DNA damage, increasing the risk of cancer development and other adverse health effects. Genotoxicity is particularly concerning as it can lead to long-term health consequences, including carcinogenesis . The toxicity of PA metabolites can vary depending on

3080-698: Is summarized in the below cladogram. Papilionidae [REDACTED] Hedylidae [REDACTED] Hesperiidae [REDACTED] Pieridae [REDACTED] Nymphalidae [REDACTED] Lycaenidae [REDACTED] Riodinidae [REDACTED] Butterfly adults are characterized by their four scale-covered wings, which give the Lepidoptera their name ( Ancient Greek λεπίς lepís, scale + πτερόν pterón, wing). These scales give butterfly wings their colour: they are pigmented with melanins that give them blacks and browns, as well as uric acid derivatives and flavones that give them yellows, but many of

3168-405: Is taken up by the gut, but there may also be large silk glands, and special glands which secrete distasteful or toxic substances. The developing wings are present in later stage instars and the gonads start development in the egg stage. When the larva is fully grown, hormones such as prothoracicotropic hormone (PTTH) are produced. At this point the larva stops feeding, and begins "wandering" in

3256-465: Is the formation of the N -oxide In the liver and lungs of certain mammal species enzymes called monooxygenase can prevent aromatization of the double 5-ring and in turn prevent the formation of the pyrrole-protein adduct. The toxicity consequences resulting from the metabolism of PAs in humans primarily revolve around hepatotoxicity and genotoxicity. PAs are metabolized in the liver through CYP450-mediated pathways. This metabolic process leads to

3344-479: The Lycaenidae , form mutual associations with ants. They communicate with the ants using vibrations that are transmitted through the substrate as well as using chemical signals. The ants provide some degree of protection to these larvae and they in turn gather honeydew secretions . Large blue ( Phengaris arion ) caterpillars trick Myrmica ants into taking them back to the ant colony where they feed on

3432-474: The Weis-Fogh ' clap-and-fling ' mechanism. Butterflies are able to change from one mode to another rapidly. Butterflies are threatened in their early stages by parasitoids and in all stages by predators, diseases and environmental factors. Braconid and other parasitic wasps lay their eggs in lepidopteran eggs or larvae and the wasps' parasitoid larvae devour their hosts, usually pupating inside or outside

3520-455: The ZW sex-determination system where females are the heterogametic sex (ZW) and males homogametic (ZZ). Butterflies are distributed worldwide except Antarctica, totalling some 18,500 species. Of these, 775 are Nearctic ; 7,700 Neotropical ; 1,575 Palearctic ; 3,650 Afrotropical ; and 4,800 are distributed across the combined Oriental and Australian / Oceania regions. The monarch butterfly

3608-565: The liver via the portal vein . Metabolites form mostly in the liver. Here esterases can hydrolyze the PAs to reduce the compound into its necine acids and bases, both forms are non-toxic for humans and do not damage the body. However, cytochrome P450 (CYP450) also metabolizes PAs, this enzyme can form pyrrolic esters (EPy), these are hepatotoxic due to their high reactivity. The EPy can also be hydrolyzed into alcoholic pyrroles, which are mutagenic and carcinogenic. Since this mostly happens in

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3696-402: The monarch and the painted lady , migrate over long distances. Many butterflies are attacked by parasites or parasitoids , including wasps , protozoans , flies , and other invertebrates, or are preyed upon by other organisms. Some species are pests because in their larval stages they can damage domestic crops or trees; other species are agents of pollination of some plants. Larvae of

3784-600: The non-coding DNA around the cortex gene can turn a black-winged butterfly into a butterfly with a yellow wing band. When the butterfly Bicyclus anynana is subjected to repeated inbreeding in the laboratory, there is a dramatic decrease in egg hatching. This severe inbreeding depression is considered to be likely due to a relatively high mutation rate to recessive alleles with substantial damaging effects and infrequent episodes of inbreeding in nature that might otherwise purge such mutations. Although B. anynana experiences inbreeding depression when forcibly inbred in

3872-680: The Americas) and Papilionoidea (all others). The oldest butterfly fossils have been dated to the Paleocene , about 56 million years ago, though molecular likely originated in the Cretaceous . Butterflies have a four-stage life cycle , and like other holometabolous insects they undergo complete metamorphosis . Winged adults lay eggs on the food plant on which their larvae , known as caterpillars , will feed. The caterpillars grow, sometimes very rapidly, and when fully developed, pupate in

3960-540: The Apollos ( Parnassius ) plugs her genital opening to prevent her from mating again. The vast majority of butterflies have a four-stage life cycle: egg , larva (caterpillar), pupa (chrysalis) and imago (adult). In the genera Colias , Erebia , Euchloe , and Parnassius , a small number of species are known that reproduce semi-parthenogenetically ; when the female dies, a partially developed larva emerges from her abdomen. Butterfly eggs are protected by

4048-479: The Ithomiini help to organize the 43 recognized genera, but this group is the subject of ongoing molecular, phylogenetic and morphological research, and the classification presented below will no doubt be refined in the near future. The sister group to the tribe Ithomiini is either the small tribe Tellervini (containing the single Australasian genus Tellervo ) or the larger tribe Danaini . The relationships of

4136-484: The LD 50 and LOAEL. PAs are also used as a defense mechanism by some organisms such as Utetheisa ornatrix . Utetheisa ornatrix caterpillars obtain these toxins from their food plants and use them as a deterrent for predators. PAs protect them from most of their natural enemies. The toxins stay in these organisms even when they metamorphose into adult moths, continuing to protect them throughout their adult stage. This

4224-507: The Neotropical orb-weaving spider Nephila clavipes released unharmed 14 species of field-caught ithomiine butterflies. The source of the protecting chemicals in the bodies of adult ithomiines proved not to be their larval host plants, as was first suggested, but rather in plants visited by the butterflies. Adults of ithomiine, mainly males, visit flowers of some Boraginaceae, ( Tournefortia , Heliotropium ), Asteraceae (mostly in

4312-430: The abdomen, generally with short prolegs on segments 3–6 and 10; the three pairs of true legs on the thorax have five segments each. Many are well camouflaged; others are aposematic with bright colours and bristly projections containing toxic chemicals obtained from their food plants. The pupa or chrysalis, unlike that of moths, is not wrapped in a cocoon. Many butterflies are sexually dimorphic . Most butterflies have

4400-405: The abdominal segments. These prolegs have rings of tiny hooks called crochets that are engaged hydrostatically and help the caterpillar grip the substrate. The epidermis bears tufts of setae , the position and number of which help in identifying the species. There is also decoration in the form of hairs, wart-like protuberances, horn-like protuberances and spines. Internally, most of the body cavity

4488-502: The adult colour pattern are marked by changes in the expression of particular transcription factors in the early pupa. The reproductive stage of the insect is the winged adult or imago . The surface of both butterflies and moths is covered by scales, each of which is an outgrowth from a single epidermal cell. The head is small and dominated by the two large compound eyes . These are capable of distinguishing flower shapes or motion but cannot view distant objects clearly. Colour perception

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4576-467: The air for wind and scents. The antennae come in various shapes and colours; the hesperiids have a pointed angle or hook to the antennae, while most other families show knobbed antennae. The antennae are richly covered with sensory organs known as sensillae . A butterfly's sense of taste is coordinated by chemoreceptors on the tarsi , or feet, which work only on contact, and are used to determine whether an egg-laying insect's offspring will be able to feed on

4664-434: The ant eggs and larvae in a parasitic relationship. Caterpillars mature through a series of developmental stages known as instars . Near the end of each stage, the larva undergoes a process called apolysis , mediated by the release of a series of neurohormones . During this phase, the cuticle , a tough outer layer made of a mixture of chitin and specialized proteins , is released from the softer epidermis beneath, and

4752-467: The basic amino acid arginine. Subsequently, homospermidine synthase exchanges the 1,3-diamonopropane by putrescine and forms symmetric homospermidine. Oxidation of homospermidine by copper-dependent diamine oxidases initiates cyclization to pyrrolizidine-1-carbaldehyde, which is reduced, to 1-hydroxymethylpyrrolizidine. Desaturation and hydroxylation ultimately form retronecine, which is acylated with an activated necic acid, for instance with senecyl-CoA2 as in

4840-658: The blues, greens, reds and iridescent colours are created by structural coloration produced by the micro-structures of the scales and hairs. As in all insects, the body is divided into three sections: the head, thorax , and abdomen . The thorax is composed of three segments, each with a pair of legs. In most families of butterfly the antennae are clubbed, unlike those of moths which may be threadlike or feathery. The long proboscis can be coiled when not in use for sipping nectar from flowers. Nearly all butterflies are diurnal , have relatively bright colours, and hold their wings vertically above their bodies when at rest, unlike

4928-454: The carcinogenic effect is currently known. However, there have been studies to determine the lowest dose for an adverse effect, also known as LOAEL . LOAEL and LD 50 (oral) for 40 PAs have been experimentally found out. These values can be seen in the Table below. The found low LD 50 values clearly show the relatively high toxicity of PAs, however no significant relation was found between

5016-412: The chemical defense of insects was given by Thomas Eisner , who showed that the spiders Nephila and Argiope rejected adults of the arctiid moth Utetheisa ornatrix that contain pyrrolizidine alkaloids from their larval host plant, Crotalaria (Fabaceae: Crotalarieae). Eisner's best-selling popular science book For Love of Insects tells the story of this exciting discovery. The subtribes in

5104-519: The combination. Identification of adult ithomiines relies on hindwing venation and male androconial scales (sex brushes located on the hindwing costa). The group has repeatedly been proposed as biological indicators of ecological conditions or biological diversity within neotropical forests, but individual sites harbor between 10 and 50 species, for the most part, and beta diversity is often great, even over relatively short distances. Ithomiine larvae feed mostly on Solanaceae host plants. Exceptions are

5192-441: The desiccated husk. Most wasps are very specific about their host species and some have been used as biological controls of pest butterflies like the large white butterfly . When the small cabbage white was accidentally introduced to New Zealand, it had no natural enemies. In order to control it, some pupae that had been parasitised by a chalcid wasp were imported, and natural control was thus regained. Some flies lay their eggs on

5280-551: The early to mid-20th century, researchers began to observe and document cases of livestock poisoning linked to the consumption of PA-containing plants. These observations led to the recognition of PAs as potent hepatotoxic and genotoxic compounds. In response to growing concerns about PA exposure, regulatory agencies around the world began to establish guidelines and regulations to limit PA levels in food, herbal products, and animal feed. These regulations aim to protect human and animal health by minimizing PA exposure and mitigating

5368-419: The epidermis begins to form a new cuticle. At the end of each instar, the larva moults , the old cuticle splits and the new cuticle expands, rapidly hardening and developing pigment. Development of butterfly wing patterns begins by the last larval instar. Caterpillars have short antennae and several simple eyes . The mouthparts are adapted for chewing with powerful mandibles and a pair of maxillae, each with

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5456-820: The exact effect of the PAs regarding beneficial effect of the plants is debated. Among these traditional medicines is the root of Ligularia achyrotricha of Tibet. Several pharmacological effects have been found. Among these effects are antimicrobial activity, antiviral activity and antineoplastic activity, acetylcholinesterase inhibition, and gastric ulcers treatment. Antimicrobial activity of several PAs have been identified as having mild to strong effect against bacteria:  E. coli and P. chrysogenum . In particular Lasiocarpine and 7-angeloyl heliotrine were found to have significant activity against these microbes. Derivatives of PAs have been found to induce cell death in these bacteria by attacking bacterial cell membranes. Retronecine derivatives have been found slow

5544-475: The example shown below. PAs are preferably found in the plant families Asteraceae (tribes Eupatorieae and Senecioneae ), Boraginaceae (many genera), Fabaceae (mainly the genus Crotalaria ), and Orchidaceae (nine genera). More than 95% of the PA-containing species investigated thus far belong to these four families. PAs are compounds made up of a necine base, a double five-membered ring with

5632-741: The family Hesperiidae (skippers). Molecular clock estimates suggest that butterflies originated sometime in the Late Cretaceous , but only significantly diversified during the Cenozoic, with one study suggesting a North American origin for the group. The oldest American butterfly is the Late Eocene Prodryas persephone from the Florissant Fossil Beds , approximately 34   million years old. Butterflies are divided into seven families that contain

5720-443: The following viruses: coxsackie , poliomyelitis , measles , and vesicular stomatitis . Antineoplastic activity, specifically against leukemia , has been found in retronecine derivatives such as indicine. A 1984 study by L. Letendre treated 22 leukaemia patients with indicine, this resulted in a significant observed antineoplastic response with four complete remissions and five partial remissions. An observed adverse side effect of

5808-556: The formation of reactive intermediates, such as pyrrolic metabolites, which can covalently bind to proteins in the liver, forming pyrrole-protein adducts. These adducts impair the function of essential liver proteins, leading to hepatotoxicity. The severity of liver damage correlates with the level of pyrrole-protein adduct formation. Hepatotoxicity induced by PAs can manifest as liver injury , inflammation , necrosis , HSOS (Hepatic Sinusoidal Obstruction Syndrome) and even liver failure in severe cases. The pathogenesis of PAs-induces HSOS

5896-409: The friction of their overlapping parts. The front two segments have a pair of spiracles which are used in respiration. The abdomen consists of ten segments and contains the gut and genital organs. The front eight segments have spiracles and the terminal segment is modified for reproduction. The male has a pair of clasping organs attached to a ring structure, and during copulation, a tubular structure

5984-475: The general public about the risks of PA exposure are ongoing. PAs are a group of naturally occurring compounds found in a wide range of plant species. These alkaloids are secondary metabolites synthesized by plants primarily as a defense mechanism against herbivores, insects, and pathogens. The biosynthesis of PAs was discovered to occur through the first pathway-specific enzyme homospermidine synthase . The polyamines putrescine and spermidine are derived from

6072-555: The grass was growing. The earliest Lepidoptera fossils date to the Triassic - Jurassic boundary, around 200   million years ago. Butterflies evolved from moths, so while the butterflies are monophyletic (forming a single clade ), the moths are not. The oldest known butterfly is Protocoeliades kristenseni from the Palaeocene aged Fur Formation of Denmark, approximately 55   million years old, which belongs to

6160-558: The groups is with Otonecine, which cannot form N -oxides , due to the methylation of the nitrogen atom. The alcohol groups on the necine bases can make esters in a wide variety of forms. Among the possibilities are mono-esters, like Floridine and Heliotrine, and di-esters either with an open or closed ring structure, like Usaramine and Lasiocarpine. In total more than 660 PAs and PA N -oxides have been identified in over 6000 plants. There are multiple ways to synthesize PAs and their derivatives. A flexible strategy would be to start with

6248-431: The growth rate of several strains of the fungus Fusarium oxysporum . Antiviral activity has been found in haliotridine derivates. However, effects are not consistent across PA compounds, derivates significantly differ in activity between different viral pathogens. As a result, it is difficult to determine an exact PA with an effect on a specific virus. Several PAs have been found with significant inhibition of growth in

6336-1030: The laboratory it recovers within a few generation when allowed to breed freely. During mate selection, adult females do not innately avoid or learn to avoid siblings, implying that such detection may not be critical to reproductive fitness. Inbreeding may persist in B anynana because the probability of encountering close relatives is rare in nature; that is, movement ecology may mask the deleterious effect of inbreeding resulting in relaxation of selection for active inbreeding avoidance behaviors. Butterflies feed primarily on nectar from flowers. Some also derive nourishment from pollen , tree sap, rotting fruit, dung, decaying flesh, and dissolved minerals in wet sand or dirt. Butterflies are important as pollinators for some species of plants. In general, they do not carry as much pollen load as bees , but they are capable of moving pollen over greater distances. Flower constancy has been observed for at least one species of butterfly. Adult butterflies consume only liquids, ingested through

6424-479: The liver, this is the most affected organ. Other affected organs are the lungs and kidneys. The EPy can escape the liver, and travel through the Disse space into the bloodstream. The electrophilic nature of pyrroles makes it an easy target for nucleophilic attack from nucleic acids and protein. If bound by glutathione it can become a non-toxic conjugate and be excreted via the kidneys. A second detoxifying pathway

6512-506: The majority of moths which fly by night, are often cryptically coloured (well camouflaged), and either hold their wings flat (touching the surface on which the moth is standing) or fold them closely over their bodies. Some day-flying moths, such as the hummingbird hawk-moth , are exceptions to these rules. Butterfly larvae , caterpillars , have a hard ( sclerotised ) head with strong mandibles used for cutting their food, most often leaves. They have cylindrical bodies, with ten segments to

6600-522: The more basal genera Tithorea , Aeria , and Elzunia that, like Tellervo and some Danainae , feed on Echiteae vines ( Apocynaceae , Apocynoideae ), as well as Megoleria and Hyposcada that feed on Gesneriaceae . The local abundance of ithomiine butterflies in the Amazon forest, the lack of observations of predation, and their "peculiar smell" led Henry Walter Bates in 1867 to suggest that these organisms should be chemically defended. This

6688-401: The name is ancient, but modern Dutch and German use different words ( vlinder and Schmetterling ) and the common name often varies substantially between otherwise closely related languages. A possible source of the name is the bright yellow male of the brimstone ( Gonepteryx rhamni ); another is that butterflies were on the wing in meadows during the spring and summer butter season while

6776-475: The outside of caterpillars and the newly hatched fly larvae bore their way through the skin and feed in a similar way to the parasitoid wasp larvae. Predators of butterflies include ants, spiders, wasps, and birds. Pyrrolizidine alkaloid PAs were first discovered in plants in the 19th century, but their toxic effects were not immediately recognized. Instead, many PA-containing plants were traditionally used for medicinal purposes in various cultures around

6864-529: The proboscis. They sip water from damp patches for hydration and feed on nectar from flowers, from which they obtain sugars for energy, and sodium and other minerals vital for reproduction. Several species of butterflies need more sodium than that provided by nectar and are attracted by sodium in salt; they sometimes land on people, attracted by the salt in human sweat. Some butterflies also visit dung and scavenge rotting fruit or carcasses to obtain minerals and nutrients. In many species, this mud-puddling behaviour

6952-431: The quest for a suitable pupation site, often the underside of a leaf or other concealed location. There it spins a button of silk which it uses to fasten its body to the surface and moults for a final time. While some caterpillars spin a cocoon to protect the pupa, most species do not. The naked pupa, often known as a chrysalis, usually hangs head down from the cremaster, a spiny pad at the posterior end, but in some species

7040-439: The repair of the stomach after gastric ulcers. A high concentration of said compounds can reduce lesions in the stomach. This may aid in treatment after operation to the stomach. The toxicological effects of PAs have been studied on animals. Retronecine derivatives are known to cause a toxic response in the livers of livestock like cows. Symptoms tend to start with a change in rough hair coat and depression. When Pregnant livestock

7128-455: The risk of toxicity. Despite regulatory efforts, the issue of PA exposure remains relevant today. Ongoing research continues to explore various aspects of PA toxicity, including the identification of new PA-containing plants, the development of sensitive analytical methods, and the assessment of human health risks associated with PA exposure. Additionally, efforts to raise awareness among healthcare professionals, herbal product manufacturers, and

7216-505: The specific PA compound and its chemical structure. Different PAs may undergo metabolic activation to varying degrees, resulting in differences in toxicity. For example, retronecine-type PAs like monocrotaline are known to be highly hepatotoxic, while other types may exhibit lower toxicity or different toxicological profiles. Next to its toxicological effects, PAs have long been researched for their potential beneficial effects. Traditional medicinal plants have long been known to contain PAs,

7304-425: The three tribes in the subfamily Danainae are still unclear. Tribe Ithomiini Godman & Salvin, 1879 Butterfly Butterflies are winged insects from the lepidopteran suborder Rhopalocera , characterized by large, often brightly coloured wings that often fold together when at rest, and a conspicuous, fluttering flight. The group comprises the superfamilies Hedyloidea (moth-butterflies in

7392-712: The treatment was observed in 5 patients who died of hepatic toxicity likely caused by the medication. Two different dose levels were tested on children: 2 g/m2/ day for 5 consecutive days (14 patients) and 2,5 g/m2/ day for 5 consecutive days (17 patients). Therapeutic effect was determined based on these doses and deemed to have a limited antileukemic effect below a dose of 3 g/m2/ day. However, this study also found severe hepatotoxic responses to be common at these doses. Four known PAs, 7- O -angeloyllycopsamine N -oxide, echimidine N -oxide, echimidine, and 7- O -angeloylretronecine have been clinically shown to inhibit acetylcholinesterase (AChE) . AChE inhibitors have been used as one of

7480-423: The treatments for Alzheimer's disease . The effect of these compounds was significant in the reduction of AChE production and thus a potential alternative in the fight against Alzheimer's. PAs like senecionine, integerrimine, retrorsine, usaramine and seneciphylline have been shown to cause an increase in both the levels of gastrin and the expression of epidermal growth factor (EGF). These two compounds aid in

7568-655: The tribe Eupatorieae , and rarely on Senecio species), Apocynaceae ( Prestonia , belonging to the tribe Echiteae) and Orchidaceae ( Epidendrum paniculatum ). Dead or withered plants are also visited and, when feeding on these plants, the butterflies scratch the tissues with their legs and suck the oozing sap. These plants are known to contain pyrrolizidine alkaloids , indicating their role as chemical sources for sequestration. Other butterfly and moth species that sequester pyrrolizidine alkaloids ( Danainae , Ctenuchidae , and Arctiidae ) also visit similar sources. The first demonstration that pyrrolizidine alkaloids were involved in

7656-455: The world. For example, herbs containing PAs were used in traditional Chinese medicine and by Native American tribes for their purported therapeutic properties. It has been estimated that 3% of the world's flowering plants contain pyrrolizidine alkaloids. Honey can contain pyrrolizidine alkaloids, as can grains, milk, offal and eggs. To date (2011), there is no international regulation of PAs in food, unlike those for herbs and medicines. In

7744-566: Was first experimentally demonstrated in 1889 when Thomas Belt fed ithomiines (that he called "Heliconii") to birds, the spider Nephila , and the white faced monkey Cebus capucinus . The butterflies were consistently rejected, but other insects were eaten. Lincoln P. Brower in 1964 also showed that adults of Ithomia drymo pellucida were rejected by the blue jay Cyanocitta cristata bromia , and Haber showed that nine species of birds also rejected several ithomiine species. Besides, João Vasconcellos-Neto and Thomas M. Lewinsohn demonstrated that

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