Lithosiini Research Articles

Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth, Lyclene dharma dharma, and Their Enantiomers

The Lichen moth, Lyclene dharma dharma (Arctiidae, Lithosiinae), plays a significant role in forest ecosystem dynamics. A concise and novel method to synthesize the active sex pheromone components, (S)-14-methyloctadecan-2-one ((S)-1), (S)-6-methyloctadecan-2-one ((S)-2), and their enantiomers has been developed. Key steps in the synthesis include the use of Evans’ chiral auxiliaries, Grignard cross-coupling reactions, hydroboration–oxidation, and Wacker oxidation. The synthesized sex pheromone components hold potential value for studies on communication mechanisms, species identification, and ecological management.

Comments on the article Review of the Eilema group of lichen moths from South Korea, with description of one new species (Lepidoptera: Erebidae: Arctiinae: Lithosiini) (Bayarsaikhan et al. 2016).

Comments on the article Review of the Eilema group of lichen moths from South Korea, with description of one new species (Lepidoptera: Erebidae: Arctiinae: Lithosiini) (Bayarsaikhan et al. 2016).

Lithosiccia, a new genus with four new species from mainland Africa (Lepidoptera: Erebidae: Arctiinae: Lithosiini)

A new lichen moth genus, Lithosiccia gen. n. similar to Siccia Walker, 1854 and Palaeosiccia Hampson, 1900 is described and assigned to the subtribe Cisthenina. Two new combinations are introduced: Lithosiccia juvenis (Holland, 1893), comb. n. and Lithosiccia major (Kiriakoff, 1958), comb. n. Four new species are described: Lithosiccia takanoi sp. n. (Sierra Leone), Lithosiccia mikra sp. n. (western Uganda), Lithosiccia bota sp. n. (Gabon and Republic of the Congo), and Lithosiccia smithi sp. n. (Republic of the Congo, Democratic Republic of the Congo, Ivory Coast and Liberia). A lectotype is designated for Nudaria juvenis Holland, 1893 in order to stabilise the nomenclature. Adults and both male and female genitalia are illustrated.

Micro-CT imaging in species description: exploring beyond sclerotized structures in lichen moths (Lepidoptera: Erebidae, Arctiinae, Lithosiini).

X-ray micro-computed tomography imaging (micro-CT) is valuable for systematic research since it permits the non-destructive scanning and imaging of internal structures of very rare species and/or type specimens. Additionally, micro-CT allows to view the morphology and the functional anatomy of structures in their natural anatomical position, without deformations that typically occur using classical dissection protocols. In this study we provide the description of two new species of lichen moths (Lepidoptera: Erebidae, Lithosiini) from the Atlantic Forest in eastern Brazil: Nodozana heliae Moraes sp. nov. from Rio de Janeiro state and Epeiromulona pataxo Moraes & Aguiar sp. nov. from Bahia state. The male and female genitalia as well as the wing morphology were examined by means of non-destructive micro-CT, subsequent 3D model reconstruction, 360 degree spinning animations, 2D images from different angles, and those were compared against classical genitalia dissections from the same specimens. We conclude that techniques complement each other, micro-CT being particularly useful to study wing venation, sclerotized internal structures and muscles, while classical dissection is useful to study membranous structures, particularly in the female genitalia, abdominal skin and specialised scales on the male 8th sternite.

Copper‐Catalyzed Coupling Reaction of Secondary Alkyl 2‐Pyridinesulfonates with Alkyl Lithium‐Based Reagents

AbstractThe Cu(OTf)2‐catalyzed alkyl–alkyl coupling reaction of a secondary substrate MeCH(OSO2Py)CH2CH2C6H4(4‐OMe) with a nBuLi‐based reagent prepared by transmetalation with MgBr2 ⋅ THF3 in THF produced a coupling product in 74 % yield. The use of soluble MgBr2 ⋅ THF3 in THF was required for this reaction. This method was applied to sBuLi and Ph(CH2)4Li. In contrast, transmetalation of MeLi with soluble MgCl2 ⋅ THF2 in THF produced the Me reagent, which was reactive for the coupling reaction. The reaction proceeded with inversion of the stereogenic carbon. Furthermore, (S)‐14‐methyloctadecan‐2‐one, a sex pheromone produced by lichen moths, was synthesized.

Camouflage in lichen moths: Field predation experiments and avian vision modelling demonstrate the importance of wing pattern elements and background for survival.

Background matching is perhaps the most ubiquitous form of defensive camouflage in the animal kingdom, an adaptive strategy that relies on the visual resemblance between a prey organism and its background to promote concealment from predators. The importance of background matching has been acknowledged for over a century, yet despite its renown and apparent pervasiveness, few studies exist that have objectively quantified its occurrence and tested the functional significance of background matching in a specific animal study system. The North Island lichen moth Declana atronivea presents a fascinating system to investigate such anti-predator coloration. This species possesses high contrast black and white forewings that appear to resemble lichen. Here we assessed the contribution of background matching to the antipredator defence of D. atronivea using field predation experiments with realistic models. We found that D. atronivea coloration confers a significant survival advantage against native avian predators when on lichen backgrounds compared to bark backgrounds, with an intermediate level of predation occurring when models were near, but not on lichen. This suggests that D. atronivea wing patterns are an adaptation for background matching. We subsequently used calibrated digital photography, avian vision modelling and image analysis techniques to objectively quantify the degree of background matching exhibited by D. atronivea and assessed the contribution of different visual elements (colour, luminance and pattern) to camouflage in this species. Only the pattern elements of D. atronivea presented a close match to that of the lichen backgrounds, with both chromatic and achromatic cues found to be poor predictors of background matching in this species. This study is one of the first to integrate vision modelling, quantitative image analysis and field predation experiments using realistic models to objectively quantify the level and functional significance of background matching in a real species, and presents an ideal system for further investigating the interrelation between multiple mechanisms of camouflage.

Aposematic Coloration of Moths Decreases Strongly along an Elevational Gradient in the Andes.

Simple SummaryCertain moths defend themselves with toxic substances, and they show this to predators with bright and contrasting coloration. At high elevations, fewer birds, bats and other predators are present that feed on these insects. We therefore expected a decreasing proportion of colorful tiger and lichen moths with increasing elevation. Our study was carried out in forests between 1040 and 2670 m in the Ecuadorian Andes. We scored all 353 observed species according to their warning coloration, and whether they mimic bees and wasps or potentially poisonous beetles. We also measured forewing length of all species. From these data community-weighted means were calculated and related to the elevation of their collection sites. As predicted, the communitywide incidence of all three defensive traits decreased substantially from tall premontane forest to open upper montane forest. In parallel, moth size increased with elevation. Moreover, the systematic composition of tiger and lichen moth assemblages changed substantially. These findings support the idea that different selection regimes favor warning coloration at lower sites with higher predation pressure, while cryptic appearance is more advantageous at higher elevations.On tropical mountains, predation pressure decreases with elevation. Accordingly, one expects an elevational decay in the prevalence of costly defensive traits such as aposematic coloration. Using light-trap catches of Arctiinae moths (353 species, 4466 individuals), assembled along a forested gradient in the megadiverse tropical Andes of southern Ecuador, we show that the incidence of aposematic coloration decreases strongly between 1040 and 2670 m asl. While over 60% of Arctiinae moths were warningly colored at lowest sites, this fraction decreased to less than 20% in montane forest, yet increased slightly again at the highest sites in the very open Purdiaea nutans forest. In parallel, the incidence of hymenopteran mimics and of species that mimic chemically defended beetles decreased with elevation. Hymenopteran mimics accounted for less than 5% of Arctiinae moths at sites above 2100 m, and beetle mimics were essentially lacking at high elevations. These patterns coincide with a change in gross taxonomic composition of Arctiinae ensembles and with an increase in average body size towards higher elevations. Representatives of Euchromiina and Ctenuchina became scarce with altitude, whereas the prevalence of Lithosiinae increased. Our findings suggest that the variable selective pressures along the elevational gradient favor warning coloration primarily at lower sites, whereas cryptic appearance of adult moths dominates in the tropical upper montane forest.

Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer

AbstractThe synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans’ chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.

Molecular phylogeny and classification of Nudariina (Lepidoptera: Erebidae) with emphasis on the genera Barsine Walker, Ammatho Walker and Ovipennis Hampson

AbstractWe provide the first multi‐locus molecular phylogeny of the lichen moth genus Barsine Walker and related genera, focussing on the recently revised Ammatho Walker and Ovipennis Hampson. One mitochondrial (cytochromec oxidase subunit I) and three nuclear (EF‐1α, RpS5 and Wg) genes were sequenced for 114 taxa representing most of the known members from these genera, sourced mainly from continental East Asia. Phylogenetic topologies obtained from maximum likelihood and Bayesian inference were generally congruent. Based on these results, we propose the four genus‐groups: the Melanaema, Asuridia, Miltochrista and Asura groups. The following genera are described: Longarsine gen.n., Callidarsine gen.n., Fangclia gen.n. and Micrarsine gen.n. The following subgenera are raised to genera: Ammathella stat.n., Striatella stat.n., Conicornuta stat.n., Delineatia stat.n., Composine stat.n., Barsipennis stat.n., Coccinigripennis stat.n. and Processine stat.n. The following genera and combinations are restored: Idopterum stat.rev., Nebulene stat.rev. and Ovipennis postalba comb.rev. The genus Hampsonascia is synonymized with Sesapa (Sesapa).

A new species of the lichen moth genus Tigricollis Singh amp; Kirti, 2016 (Lepidoptera: Erebidae: Arctiinae) from eastern Indonesia.

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Lichen moths do not benefit from ‘element imitation’ masquerade in the absence of a matching background

Predation places significant selection pressures on prey species and many have evolved incredible and diverse colour patterns in response. A fascinating example of such adaptive colouration and morphology is masquerade, a camouflage strategy in which organisms resemble innocuous and inedible objects, such as leaves or twigs. Masquerading prey avoid predation by being misclassified as irrelevant parts of the environment, rather than as food. Here we assess a putative case of masquerade in the North Island lichen moth, Declana atronivea (Geometridae), an endemic New Zealand species with intricate black and white forewings that appear to resemble lichen. Lichen masquerade is a type of ‘element imitation’ in which the object being mimicked forms a common element of the environmental pattern. However, unlike discrete objects, such as leaves and twigs, lichen may be difficult to distinguish as a distinct entity. This raises the question of whether D. atronivea can be said to look like ‘a’ lichen, or whether its body colouration appears as a component of a larger patch of lichen. In this case, does the lichen resemblance function as a form of masquerade, or is it an example of background matching? Using laboratory experiments with domestic chicks (Gallus gallus) as predators, we investigated whether D. atronivea moths avoid predation by being misclassified as lichen. We exposed naive and experienced chicks to D. atronivea and compared their responses, predicting that if the moths do benefit from masquerade, chicks with previous experience of lichen would take longer to attack. Our hypothesis was not supported; there was no significant difference in predator interaction regardless of prior experience, suggesting that, in the absence of a matching background, D. atronivea do not benefit from masquerading as lichen. Rather, this may be a case of context-dependent misclassification, or perhaps the forewing colouration promotes concealment through crypsis.

Paraona wallaceana sp. nov., a lichen moth endemic to Flores Island, Indonesia (Erebidae: Arctiinae: Lithosiini)

In this article Paraona wallaceana sp. nov., a new lichen moth (Erebidae: Arctiinae: Lithosiini) was described from Flores Island, Indonesia.

Establishment of a new genus for Nudina xizangensis Fang, 2000(Lepidoptera, Erebidae, Arctiinae, Lithosiini).

The little known species Nudina xizangensis Fang, 2000 is rediscovered from its type locality, Beibeng, Motuo County, Southeast Xizang, with genitalia of both sexes illustrated for the first time. Based on its unique genitalia structure, a new lichen moth genus, Paranudina Huang Wang gen. nov., is described with N. xizangensis as the type species. Adults and genitalia of Paranudina xizangensis (Fang, 2000) comb. nov. and Nudina artaxidia (Butler, 1881) are compared and illustrated.

Barsine wangi, a new species from Guangdong, southern China (Lepidoptera, Erebidae, Arctiinae).

Barsine Walker, 1854 is a large genus of lichen moths (family Erebidae, subfamily Arctiinae, tribe Lithosiini) including about a hundred of valid species and widespread in Oriental tropics, mainland China, Taiwan, Japan, Korea and the southern part of the Russian Far East. During the studies of Lithosiini materials recently collected in the Chinese Province of Guangdong, we found one more, yet undescribed Barsine species. It is related to the recently described B. cacharensis Singh Kirti, 2016 by the male and female genitalia structure, but externally it is more similar to B. defecta Walker, 1854 and B. gratissima (de Joannis, 1930). The species is described below as new.

Moth assemblages in Costa Rica rain forest mirror small‐scale topographic heterogeneity

AbstractIn many tropical lowland rain forests, topographic variation increases environmental heterogeneity, thus contributing to the extraordinary biodiversity of tropical lowland forests. While a growing number of studies have addressed effects of topographic differences on tropical insect communities at regional scales (e.g., along extensive elevational gradients), surprisingly little is known about topographic effects at smaller spatial scales. The present study investigates moth assemblages in a topographically heterogeneous lowland rain forest landscape, at distances of less than a few hundred meters, in the Golfo Dulce region (SW Costa Rica). Three moth lineages—Erebidae–Arctiinae (tiger and lichen moths), the bombycoid complex, and Geometridae (inchworm moths)—were examined by means of automatic light traps in three different forest types: creek forest, slope forest, and ridge forest. Altogether, 6,543 individuals of 419 species were observed. Moth assemblages differed significantly between the three forest types regarding species richness, total abundance, and species composition. Moth richness and abundance increased more than fourfold and eightfold from creek over slope to ridge forest sites. All three taxonomic units showed identical biodiversity patterns, notwithstanding their strong differences in multiple eco‐morphological traits. An indicator species analysis revealed that most species identified as characteristic were associated either with the ridge forest alone or with ridge plus slope forests, but very few with the creek forest. Despite their mobility, local moth assemblages are highly differentially filtered from the same regional species pool. Hence, variation in environmental factors significantly affects assemblages of tropical moth species at small spatial scales.Abstract in Spanish is available with online material.

Identification of Sex Pheromone of Miltochrista striata (Lepidoptera: Arctiidae).

A species of lichen moth, Miltochrista striata (Bremer & Grey, 1852), feeds on lichens in Chinese tea plantations (Camellia sinensis (L.) O. Kuntze (Ericales:Theaceae)). A previous sex attractant screening test showed that male moths of M. striata were attracted by a mixture of (Z,Z,Z)-3,6,9-octadecatriene (Z3,Z6,Z9-18:H), (Z,Z,Z)-3,6,9-nonadecatriene (Z3,Z6,Z9-19:H), and their monoepoxy derivatives. To determine which of the component is an effective sex attractant for M. striata, the sex pheromone glands of female moths were excised and extracted with n-hexane. By comparison with the retention time and mass spectra of synthetic chemicals, two compounds in the crude extracts were identified as Z3,Z6,Z9-18:H and (Z,Z)-3,6-cis-9,10-epoxy-octadecadiene (Z3,Z6,epo9-18:H) using gas chromatography-mass spectrometry. The results of electroantennographic tests showed that the electrophysiological activities of Z3,Z6,Z9-18:H and Z3,Z6,epo9-18:H were distinctly higher than those of (Z,Z)-6,9-cis-3,4-epoxy-octadecadiene, (Z,Z)-3,9-cis-6,7-epoxy-octadecadiene, (Z,Z,Z)-3,6,9-nonadecatriene, (Z,Z)-6,9-cis-3,4-epoxy-nonadecatriene, (Z,Z)-3,9-cis-6,7-epoxy-nonadecatriene, and (Z,Z)-3,6-cis-9,10-epoxy-nonadecatriene. Field trapping showed that only a mixture of Z3,Z6,Z9-18:H and Z3,Z6,epo9-18:H attracted male moths, and the optimal mixture of these compounds was the ratio of 4:6 at 1.0-mg dosage. The results represent the first determination of the sex pheromone of a lichen moth in a tea plantation and provide a scientific basis to develop an effective protocol using sex pheromone to monitor populations of M. striata.

A new species of Hypoprepia from the mountains of central Arizona (Lepidoptera, Erebidae, Arctiinae, Lithosiini).

A new firefly-mimicking lichen moth of the genus Hypoprepia, H.lampyroides Palting & Ferguson, sp. n., is described from the mountains of east-central Arizona and the Sierra Madre Occidental of Mexico. Hypoprepia Hübner, 1831 is a North American genus of lithosiine tiger moths, previously consisting of five species: H.fucosa Hübner, 1831 and H.miniata (Kirby, 1837), both of eastern and central North America; H.cadaverosa Strecker, 1878 from the Rocky Mountains into New Mexico and west Texas; H.inculta H. Edwards, 1882, a widespread western USA species and H.muelleri Dyar, 1907 from the vicinity of Mexico City. The latter is herein synonymized under H.inculta (= H.muellerisyn. n.), resulting in the total number of taxa in the genus unchanged at five.

Synonymic Notes on Some Lithosiinae, Arctiidae, from Japan and Taiwan, with Descriptions of Three New Species : Lepidoptera

Synonymic Notes on Some Lithosiinae, Arctiidae, from Japan and Taiwan, with Descriptions of Three New Species : Lepidoptera

HPLC-MS Analysis of Lichen-Derived Metabolites in the Life Stages of Crambidia cephalica (Grote & Robinson).

Tiger moths (Lepidoptera: Erebidae: Arctiinae: Arctiini) are notable for their specialized associations with hosts that produce toxic secondary compounds, and are thus an ideal study system for understanding insect-plant interactions and the evolution of antipredatory defense. Likewise, their sister lineage (Arctiinae: Lithosiini) has been documented feeding on algae and lichens, and is known to sequester lichen-derived secondary compounds from the larval to adult stages. Prevalence of lichenivory in this early radiation (ca. 3000 species) may provide clues to the phylogenetic basis for storied chemical sequestration within all tiger moths. Despite the evolutionary significance of this trait, we lack a basic understanding of the extent of lichenivory among lithosiines, and the distribution of sequestered chemicals among life stages. The dynamics of chemical sequestration throughout the lifecycle for the lichen moth Crambidia cephalica were investigated by testing the hypothesis that lichen-derived metabolites are unequally distributed among life stages, and that laboratory-reared C. cephalica have less metabolite diversity than wild-caught individuals. Crambidia cephalica was reared on Physcia, and analyzed using high-performance liquid chromatography coupled to mass spectrometry (HPLC-MS). Several putative lichen-derived metabolites were detected across three life stages, i.e., larval, pupal, and adult, and differences among life stages and lichen host were observed. These results provide evidence that multiple lichen-derived metabolites are sequestered by C. cephalica; some metabolites are retained through adulthood, and others are lost or modified in earlier life stages. The presence of differing lichen-derived metabolites across life stages may indicate functional properties of the metabolites for C. cephalica with regards to chemical protection from antagonists, and other physiological processes.

Review of the Eilema group of lichen moths from South Korea, with description of one new species (Lepidoptera: Erebidae: Arctiinae: Lithosiini)

This review details the Korean species of the Eilema group in the subfamily Arctiinae of Erebidae: 19 species in five genera (Manulea, Collita, Katha, Dolgoma, and Wittia), a new species (Collita hwacheonensis Bayarsaikhan & Bae, sp. nov.), and an unrecorded species [C. vetusta aegrota (Butler 1877)]. All species are diagnosed, and figures of the adults and genitalia and a key to species based on male genital structure of Eilema group in South Korea are included.