Chemical composition of Laurencia spp. collected from the Seto Inland Sea of Japan

The chemical composition of three Laurencia spp., Laurencia sp., L. okamurae and L. saitoi, which were collected from the Seto Inland Sea of Japan, has been examined. Laurencia sp. collected from the coast of Matoba Park, Takehara, Hiroshima Prefecture, contained a brominated chamigrane-type sesquiterpene (1), named matobol, as the main metabolite. The structure of matobol was determined as (+)-(2R,3R,6R,10S)-2,10-dibromochamigr-7(14)-en-3-ol (1). This is the first time that the optically active 1 has been isolated from Laurencia. On the other hand, L. okamurae from the coast of Ikunoshima Island, Hiroshima Prefecture, produced laurinterol (2) that is a known cyclolaurane-type sesquiterpene characteristic to this species in Japan. L. saitoi from the coast of Matoba Park contained a known bromoallenic C₁₅-acetogenin, neolaurallene (3).     

Snyderol derivatives from Laurencia obtusa collected in Corsica

8-keto-10-dehydrobromo-γ-snyderol (1), a new sesquiterpene exhibiting the unusual γ-snyderane skeleton, was isolated from the ethyl acetate extract of Laurencia obtusa collected in Ajaccio (Corsica, France). (1) was isolated and fully characterized by detailed spectroscopic analysis. Six known compounds were identified after column chromatography steps using a ¹³C NMR based computerized method developed in our laboratory: α-snyderol (2), two rearranged derivatives of α-snyderol (3,4), 8-keto-10-dehydrobromo-β-snyderol (5), β-snyderol (6) and 8-hydroxy-β-snyderol (7).     

Chemical relationship between red algae genus Laurencia and sea hare (Aplysia dactylomela Rang) in the North Borneo Island

Red algae genus Laurencia is an interesting alga with the ability to produce halogenated secondary metabolites that exhibits ecological and pharmaceutical potential. In nature, Laurencia is selectively grazed by sea hares (Aplysia dactylomela). In this study, Laurencia populations in three islands (Mantanani, Sulug, and Dinawan Islands) in the coastal waters of North Borneo were investigated and their chemical relationship with sea hare determined. Four species of Laurencia were found to grow abundantly in these waters, Laurencia snackeyi, Laurencia majuscula, Laurencia nangii, and Laurencia similis. Sea hares, Aplysia dactylomela, found grazing on Laurencia were collected and their chemical composition determined. A total of 20 halogenated metabolites were isolated and identified via spectroscopic data. Isolated compounds could be grouped into syndrean (5), chamigrane (6), non-chamigrane sesquiterpene (3), cuparane (1), bromoindole (2), and C15 acetogenin (acetylene type) (3). Sea hares from Mantanani, Sulug, and Dinawan Islands contained a total of 9, 10, and 10 compounds, respectively. In addition, 12-acetoxypalisadin B (1), which was isolated from sea hares of Sulug Island is a first record of its existence in nature.     

Penicisteroids A and B, antifungal and cytotoxic polyoxygenated steroids from the marine alga-derived endophytic fungus Penicillium chrysogenum QEN-24S

Two new polyoxygenated steroids, namely, penicisteroids A and B (1 and 2), were obtained from the culture extract of Penicillium chrysogenum QEN-24S, an endophytic fungus isolated from an unidentified marine red algal species of the genus Laurencia. In addition, seven known steroids (3-9) were also isolated and identified. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The absolute configuration for compound 1 was determined by application of the modified Mosher’s method. Penicisteroid A (1), which is a structurally unique steroid having tetrahydroxy and C-16-acetoxy groups, displayed potent antifungal and cytotoxic activity in the preliminary bioassays. Preliminary structure-activity relationships are discussed.     

Antiprotozoal activities of marine polyether triterpenoids

Chagas disease and leishmaniasis are tropical neglected diseases caused by kinetoplastids protozoan parasites of Trypanosoma and Leishmania genera, and a public health burden with high morbidity and mortality rates in developing countries. Among difficulties with their epidemiological control, a major problem is their limited and toxic treatments to attend the affected populations; therefore, new therapies are needed in order to find new active molecules. In this work, sixteen Laurencia oxasqualenoid metabolites, natural compounds 1–11 and semisynthetic derivatives 12–16, were tested against Leishmania amazonensis, Leishmania donovani and Trypanosoma cruzi. The results obtained point out that eight substances possess potent activities, with IC₅₀ values in the range of 5.40–46.45 µM. The antikinetoplastid action mode of the main metabolite dehydrothyrsiferol (1) was developed, also supported by AFM images.The semi-synthetic active compound 28-iodosaiyacenol B (15) showed an IC₅₀ 5.40 µM against Leishmania amazonensis, turned to be non-toxic against the murine macrophage cell line J774A.1 (CC₅₀ > 100). These values are comparable with the reference compound miltefosine IC₅₀ 6.48 ± 0.24 and CC₅₀ 72.19 ± 3.06 μM, suggesting that this substance could be scaffold for development of new antikinetoplastid drugs.     

New Taxa and Host Associations of the Weevil Subfamily Ceutorhynchinae (Coleoptera,Curculionidae) from Thailand

A new subgenus of Mecysmoderes Sch., Enzoellus Korotyaev, subgen. n. (type species Mecysmoderes carinatus Faust), two new genera of the tribe Hypohypurini Colonnelli, Siamohypurus Korotyaev, gen. n. (type species S. samuelsoni Korotyaev, sp. n.), Glikmanellus Korotyaev, gen. n. (type species G. rosti Korotyaev, sp. n.) and eleven new species of the weevil subfamily Ceutorhynchinae are described: Mecysmoderes (Memecyderes) sarukhanovi Korotyaev, sp. n. from Thailand, M. (Enzoellus) gressitti Korotyaev, sp. n. from Thailand and Laos, M. (Enzoellus) muratovi Korotyaev, sp. n., Megahypurus oroszi Korotyaev, sp. n., Cyphohypurus suppantschitschi Korotyaev, sp. n., Siamohypurus samuelsoni Korotyaev, sp. n., S. attilai Korotyaev, sp. n., Glikmanellus rosti Korotyaev, sp. n., all from Thailand; G. baloghi Korotyaev, sp. n. from Sri Lanka; G. obrieni Korotyaev, sp. n. and G. louisae Korotyaev, sp. n., both from India. A key to three species of Megahypurus from Thailand is given. Host plants are determined for Megahypurus alexandri Kor. and Glikmanellus rosti sp. n. from Koh Kood Island in southern Thailand, which were repeatedly collected from a tree of the family Rubiaceae.     

Jiriella brunnea sp. nov. (Coleoptera: Dermestidae: Megatominae) from Thailand and Burma — the second known species of the genus Jiriella

Jiriella brunnea Háva & Kadej, sp. nov. from Thailand and Burma is described. The habitus, antenna, genitalia are illustrated and compared with related species Jiriella thailandica (Háva, 2012).     

New prenylated dihydrochalcones from the leaves of Artocarpus elasticus

The leaves of Artocarpus elasticus collected in Thailand were investigated for chemical constituents. Four new prenylated dihydrochalcones named elastichalcones C, D, E, F (1, 3, 5, 6) together with elastichalcone B (2) and artocarpanone (4) were isolated. Their structures were determined from analysis of spectroscopic data. Elastichalcone C (1) exhibited good antibacterial activity and cytotoxicity.     

Description of new species of two genera Dayus Mahmood and Znana Dworakowska from Thailand (Hemiptera: Cicadellidae: Typhlocybinae)

Two genera, Dayus Mahmood, 1967 and Znana Dworakowska, 1994 of the leafhopper tribe Empoascini (Hemiptera: Cicadellidae: Typhlocybinae) are reviewed. One new species of each genus, Dayus furcatus sp. nov. and Znana furca sp. nov., are described from Thailand. A checklist and distribution summary of Dayus Mahmood species is given. Male habitus photos and illustrations of male genitalia of the two new species and notes on allied species are also provided.     

Structural diversity and geographical distribution of halogenated secondary metabolites in red algae,Laurencia nangii Masuda (Rhodomelaceae,Ceramiales), in the coastal waters of North Borneo Island

The red algae genus Laurencia (Rhodomelaceae, Ceramiales) is known as a prolific producer of halogenated secondary metabolites with a high level of species diversity and geographical distribution. In North Borneo Island, Malaysia, there are four main Laurencia species: Laurencia snackeyi, Laurencia majuscula, Laurencia similis and L. nangii. Although the chemistry of Laurencia is well studied, the diversity of compounds in L. nangii has not been thoroughly investigated. Therefore, we studied the chemical constituents of seven populations of L. nangii from Tunku Abdul Rahman Marine Park (two populations), Dinawan Island (one population), Tun Mustapha Marine Park (two populations) and Tun Sakaran Marine Park (two populations). Halogenated compounds were isolated and the structures determined via spectroscopic methods. A total of 20 metabolites belonging to the classes of sesquiterpenes, acetylenes, bromoallenes, diterpenes and triterpenes were identified. Populations from Tunku Abdul Rahman Marine Park and Dinawan Island contained non-chamigrane-type sesquiterpenes, acetylenes and diterpenes. Populations from Tun Mustapha Marine Park contained chamigrane-type sesquiterpenes, acetylenes and diterpenes. However, the chemical compositions of populations from Tun Sakaran Marine Park were found to differ significantly, containing chamigrane-type and non-chamigrane-type sesquiterpenes, bromoallenes and triterpenes. This investigation has revealed the presence of interesting chemotaxonomical markers in populations of L. nangii and the existence of chemical races in this species.     

Phenotypic and Genetic Diversity of Local <Emphasis Type="Italic">Perilla</Emphasis> (<Emphasis Type="Italic">Perilla frutescens</Emphasis> (L.) Britt.) from Northern Thailand

Phenotypic and Genetic Diversity of Local Perilla ( Perilla frutescens (L.) Britt.) from Northern Thailand. Perilla frutescens (L.) Britt., an important oil and culinary crop in Asia, is a valuable genetic resource. Despite its nutritional value and historic and cultural importance, research on Perilla has been scarce, particularly as far as its genetic diversity is concerned. The aims of the present study were to assess variability within and between 29 seed samples of P. frutescens collected from farmers in northern Thailand, and evaluation conducted of their genetic, morphological, and agronomic characteristics, and the seed composition, including polyunsaturated fatty acids omega-3, omega-6, and omega-9, and the vitamin E γ-tocopherols. Perilla frutescens (L.) Britt. of northern Thailand is genetically variable, and structured according to origin of collection which was the consequence of local adaptation. The discovery of high levels of polyunsaturated fatty acids, namely α-linolenic acid and γ-tocopherols, in some Perilla samples indicates the potential for utilizing Perilla for its high omega-3 content including as a vitamin E supplement for humans, a prospect that should be taken into account when planning conservation strategies or when Perilla variability is used in breeding programs.     

Freshwater fishes of thailand as experimental intermediate hosts for Capillaria philippinensis

Bhaibulaya M., Indra-Ngarm S. and Ananthapruti M. 1979. Freshwater fishes of Thailand as experimental intermediate hosts for Capillaria philippinensis. The International Journal for Parasitology9: 105–108. Nine species of freshwater fishes from Thailand have been exposed to infection with embryonated eggs of Capillaria philippinensis. The eggs were fed to fishes with food or through a polyethylene tube. After 10–30 days larvae capable of establishing intestinal capillariasis in Mongolian gerbils were recovered from six fish species: Cyprinus carpio, Puntius gonionotus, Aplocheilus panchax, Gambusia holbrookii, Rasbora borapelensis, and Trichopsis vittatus. Larvae were not recovered from Tilapia nilotica, Osteochilus hasseltii and Trichogaster trichopterus. Five human cases of intestinal capillariasis have been reported from widely scattered areas of Thailand and the natural intermediate and definitive hosts remain to be determined.     

Revision of the Agrilus beatissimus species–group (Coleoptera,Buprestidae) with description of five new species from Southeast Asia

The newly defined Agrilus beatissimus species–group comprising seven species from Southeast Asia is revised. The key to species is provided and complemented with illustrations of habitus, genitalia and type specimens. The following five new species are described: Agrilus bilyanus sp. nov. (Thailand); A. campana sp. nov. (Laos); A. galazopos sp. nov. (Laos); A. plurifrons sp. nov. (Laos, Myanmar) and A. undatus sp. nov. (Laos). Comprehensive commented references, data on type specimens and new faunal records are cited. The distribution is updated for A. beatissimusDescarpentries and Villiers 1963 and A. dunoyeriBaudon 1968.     

Occurrence of the anthracotheriid Brachyodus (Artiodactyla,Mammalia) in the early Middle Miocene of Thailand

Remains of Brachyodus cf. onoideus from the Ban Na Sai Basin (Thailand) are described. They correspond to the first occurrence of that genus in South Asia, and might document the latest record of the genus in the Old World. Sihongotherium from the Middle Miocene of eastern China is likely a representative of Brachyodus that was misinterpreted. To cite this article: S. Ducrocq et al., C. R. Palevol 2 (2003).     

Morphology of Laurencia clavata and L. elata (Ceramiales,Rhodophyta) in relation to generic circumscription in the Laurencia complex

Laurencia Lamouroux (Rhodophyta) was recently separated into three genera–Laurencia, Chondrophycus (Tokida et Saito) Garbary et Harper and Osmundea Stackhouse – each of which was newly defined based on vegetative and reproductive structures. In this study, the previously unknown vegetative and reproductive morphology of two Australian endemic species of Laurencia, L. clavata Sonder and L. elata (C. Agardh) Harvey, was studied, particularly in the context of the revised generic delineation. These species exhibit vegetative axes with four pericentral cells and trichoblast-type spermatangial development. Tetrasporangia are abaxially produced from the existing third and fourth pericentral cells. L. clavata has terete thalli with distinctive verticillate branching and is similar to Chondria C. Agardh, rather than to Laurencia, in having an unusually marked constriction at the base of the branches and starch accumulation in subcortical and medullary cells. Compared to Laurencia, apical cells of this species exhibit a less oblique division ; the resulting recognizable axial cell rows extend somewhat below the branches, and particularly at a young stage they are also clear throughout branchlets. However, other vegetative and spermatangial structures show that L. clavata is more closely allied to Laurencia than to Chondria, and it is placed in Laurencia. By contrast, L. elata exhibits morphology typical of Laurencia and is characterized by large, robust, compressed thalli with fastigiately distichous branching and an extensive secondary cortex. Furthermore, it appears to be distinct from similar species in sometimes having a parasitic species of Janczewskia Solms-Laubach (Rhodophyta). Taxonomy of Laurencia is discussed on the basis of these and previous studies.     

A new section of clitoria subgenus neurocarpum (Leguminosae) and a new species endemic to Thailand

Tanystyloba Fantz is a section ofClitoria subgenusNeurocarpum which includes six species:C. macrophylla Wall, ex Benth.,C. javanica Miq.,C. australis Benth.,C. hanceana Hemsl.,C. linearis Gagn., andC. cordiformis Fantz, a species endemic to Thailand.     

A new antibacterial amino phenyl pyrrolidone derivative from a novel marine gliding bacterium Rapidithrix thailandica

A recently described marine gliding bacterium Rapidithrix thailandica strain TISTR 1741 was isolated from biofilm specimen collected from the Andaman Sea in Thailand. Four liters fermentation broth of R. thailandica TISTR 1741 cultivated in VY/2 medium were extracted with methanol to yield a novel amino phenyl pyrrolidone derivative compound (1) with antibacterial activities. The chemical structure and physico-chemical properties of 1 were investigated by spectrometry techniques. Compound 1 exhibited selective inhibition against vancomycin-resistant Enterococcus faecalis (VRE) with the MIC of 5.97 mM.     

Four new species of musci from the andes of Ecuador and Colombia

Eobruchia ecuatoriana sp. nov. (Bruchiaceae) has the aspect of a diminutiveTrematodon, but is distinctive in having a mitrate calyptra and flexuous seta;Macromitrium perreflexum sp. nov. (Orthotrichaceae) has ramarkably reflexed leaves, unlike any known species;Lepidopilum pulcherrimum sp. nov. (Hookeriaceae) is distinguished by its large size and beautifully undulate leaves;Symphyodon americanus sp. nov. (Symphyodontaceae) is remarkable in being the first American representative of a genus and family previously known only from Asia; it is most closely related toS. echinatus (Mitt.) Jaeg. of the Himalayas and Thailand.     

Nonhalogenated organic molecules from Laurencia algae

The marine red algae of the genus Laurencia have produced more 700 secondary metabolites and exhibited high molecular diversity and intriguing bioactivity. Since the halogenated structures have been comprehensively reviewed previously, this review, covering up to the end of 2012, mainly focuses on the source, structure elucidation, and bioactivity of nonhalogenated organic molecules from Laurencia spp. as well as the relationship between nonhalogenated and halogenated products. Overall, 173 new or new naturally occurring compounds with 58 skeletons, mainly including sesquiterpenes, diterpenes, triterpenes, and C₁₅-acetogenins, are described.     

Revision of the Barsine punicea Moore, 1878 species-group,with descriptions of two new species and two new subspecies (Lepidoptera,Erebidae, Arctiinae)

The Barsine puniceaMoore, 1878 species-group is revised. Two new species, Barsine bachma Volynkin & ?erný, sp. nov. (Central Vietnam and Hainan, China) and Barsine sirikitae Volynkin & ?erný, sp. nov. (North Thailand), and two new subspecies, Barsine punicea kachina Volynkin & ?erný, ssp. nov. (North Myanmar) and Barsine bachma bolovena Volynkin & ?erný, ssp. nov. (South Laos) are described. Barsine punicea melanandra ?erný, 2009 is upgraded to the species level: Barsine melanandra ?erný, 2009, stat. nov.Miltochrista rothschildiDraudt, 1914 is synonymized with Barsine punicea and downgraded to the subspecies status: Barsine punicea rothschildi (Draudt, 1914), syn. & stat. nov. The lectotype for Miltochrista coccineaRothschild, 1913 is designated. Adult, male and female genitalia are illustrated.