The constituents of the marine red alga Laurencia hamata Yamada (Kagi-sozo in Japanese), which was entangled in the brown alga Sargassum sp., collected from the coast of Oga Peninsula, Akita Prefecture, Japan were investigated. This species produced two halogenated C15-acetogenins, a new hamatenyne (2) and a known cis-maneonene-A (1). Their structures were deduced on the basis of spectroscopic data and comparison with previously reported data. In addition, the biological activities of the isolated compounds were evaluated against the brine shrimp assay and the DPPH antioxidant assay. This is the first report on chemistry and morphology of L. hamata.

We examined the chemical constitution of the red alga Laurencia saitoi Perestenko, collected from Katsuura, Boso Peninsula, Chiba Prefecture, Japan. This specimen produced a new polyhalogenated acetogenin, named katsuurallene ( 1 ), which structure was determined by the spectral methods, along with known diterpene, deoxyparguerol ( 2 ) and triterpene, thyrsiferol ( 3 ). In this paper we describe the structural elucidation of katsuurallene together with some biological activities.

Seaweeds of the red algal genus Laurencia are distributed worldwide in tropical, subtropical to temperate zones, growing in Japan from Hokkaido to Okinawa. Laurencia is highly difficult to classify morphologically because of a high degree of morphological variation within individual species. Nevertheless, Laurencia investigation is favored by organic chemists as it produces uniquely structured compounds. Halogenated secondary metabolites are considered to be used as chemical markers for chemical systematics (chemotaxonomy) of this troublesome genus. As a "weedy seaweed", Laurencia is not effectively utilized, yet it produces a variety of metabolites and thus, holds good potential for containing compounds with specific activity, especially in aspects of secondary metabolites. In this review, we reported significant morphological features to distinguish species in this genus, and the morphological features, habitat, distribution, and chemical composition that help discriminate Japanese Laurencia species.

SUMMARY Colpomenia borea sp. nov. is described from Hokkaido, Japan and Magadan, Far East Russia based on morphological observations and molecular analyses using mitochondrial cox 3 and chloroplast rbc L genes. This new species is distinguished from other Colpomenia by its small globular to ovoidal thallus up to 5 cm in diameter, and thin thallus membrane composed of a cortex of one to two‐cell layers and a colorless medulla of up to three layers. This species is epiphytic on the brown alga Stephanocystis in areas protected against waves. The life history in culture of C . borea was investigated and the observed life history pattern was similar to those reported in C . peregrina and C . sinuosa . Our phylogenetic analyses supported that C . borea is a distinct species, yet it is more related to C. peregrina than C. sinuosa .

The red alga Laurencia nipponica comprises various chemical races distributed relative to the ocean current in Japanese coastal areas. We investigated the chemical compositions and chemical races of L. nipponica distributed from the Kunashiri and Etorofu Islands, the confluence of the Soya warm current and Oya-shio cold current. Two new halogenated secondary metabolites, deacetylneonipponallene (1) and neopacifenol (2), along with four known compounds, deoxyprepacifenol (3), pacifenol (4), halo-chamigrene diether (5), and isolaurallene (6) were isolated from L. nipponica collected at Chikappunai, Kunashiri Island, while Zaimokuiwa (Kunashiri Island) and Sana (Etorofu Island) populations contained 3, 7-hydroxylaurene (7), 2,10-dibromo-3-chloro-9-hydroxy-α-chamigrene (8), and (3Z)-laurefucin (9). The structures of 1 and 2 were established using spectroscopic methods. The chemical races of L. nipponica distributed in this area were divided into 6- and 9-producing races. Interestingly, both races contained 4 as an additional race-index, as well as its derivatives, 2 and 5. To the best of our knowledge, this is the first example of a race comprising a mixture of two race-index compounds, suggesting that the convergence of two currents causes the production of new and diverse chemical races in this species.

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).

The study was conducted to clarify how early high plane of nutrition related to metabolic imprinting affected growth, carcass characteristics, and meat quality of grass-fed Wagyu (Japanese Black cattle). Wagyu steers were allocated randomly into 2 dietary groups: (1) steers fed milk replacer (crude protein 26.0%, crude fat 25.5%; maximum intake 0.6 kg/d) until 3 mo of age and then fed roughage (orchard grass hay) ad libitum from 4 to 10 mo of age (roughage group, RG; n = 11); (2) steers fed milk replacer (maximum intake of 1.8 kg/d) until 3 mo of age and then fed a high-concentrate diet from 4 to 10 mo of age (early high nutrition, EHN; n = 12). After 11 mo of age, all steers were fed roughage ad libitum until 31 mo of age and then slaughtered. Growth performance, carcass traits, longissimus muscle (LM) meat quality and intramuscular fat (IMF) content, plasma insulin-like growth factor I (IGF-I) concentration, and bone mineral density were measured. Body weight was greater in EHN steers (571 kg) than RG steers (520 kg; P < 0.01). Plasma IGF-I levels were higher in EHN steers than in RG steers at 3, 10, and 14 mo of age (P < 0.01, P < 0.005, P < 0.001, respectively); however, plasma IGF-I levels were lower in EHN steers compared with RG steers at 30 mo of age (P < 0.01). The total weight of the muscles and bones of the left half of the carcass was not different between the 2 groups (P = 0.065). Five of the 19 muscles investigated (semimembranosus, P = 0.036; infraspinatus, P = 0.024; supraspinatus, P = 0.0019; serratus ventralis cervicis, P = 0.032; serratus ventralis thoracis, P = 0.027) were heavier in EHN steers. Total fat weight in the left half of the carcass was 30% greater (P = 0.025) in HNE carcasses. Subcutaneous and perirenal fat weights were 53% and 84% greater (P = 0.008, P = 0.002, respectively) in EHN carcasses. The LM IMF content was greater in EHN loins (13.2%) compared with RG loins (9.4%) at 31 mo of age (P = 0.038); however, no differences were found for shear force, tenderness, and cook loss. These results suggested early high-nutrition affected the growth and meat quality of livestock.

We examined the constitution of Laurencia mariannensis collected from the east coast of Tean Island, Thailand. The structure of a new brominated rearranged cyclolaurane-type sesquiterpene, named teanol (1), is reported. This is the first report on biology and chemistry of the Thailand red algal genus Laurencia (Rhodomelaceae, Ceramiales).

We report on the chemical characteristics of the red alga Laurencia japonensis, collected off the coast of Yoshio, Katsuura, Boso Peninsula, Japan. We isolated two new brominated C15-acetogenins in this species, which we name katsuurenyne A (1) and katsuurenyne B (2), along with two already known halogenated terpenes [2,10-dibromo-3-chloro-α-chamigrene (7) and aplysiadiol (8)]. We extensively analysed spectral data (from IR, ESI-MS, 1D-NMR and 2D-NMR) to confirm the structure of these compounds.

The constitution of Laurencia snackeyi (Weber-van Bosse) Masuda (Ryukyu-sozo in Japanese) from three locations, Minna Island, Sesoko Island and Kayo Coast in Okinawa Prefecture, Japan, is reported. This species produced snyderane-type sesquiterpenes, palisadin A (1), palisadin B (2) and aplysistatin (3) as characteristic metabolites. The species name of "Laurencia luzonensis Masuda", which has previously been reported in several papers, should be revised to L. snackeyi.

Using morphological and molecular evidence, we describe a new genus, Neochondria, based on specimens formerly identified as Chondria tenuissima' sensu Okamura in Japan. The generitype, Neochondria ammophila sp. nov., is not closely related to Chondria capillaris (Hudson) M.J. Wynne, the generitype of Chondria. The anatomy of Neochondria differs from that of Chondria by the development of adventitious elongate cells between the five major pericentral cells, forming densely compact layers surrounding the axial strand, even in the ultimate branchlets. We propose the new combination, Neochondria nidifica, based on Chondria nidifica Harvey from California, USA and Baja California, Mexico. Multigene analyses (rbcL, small subunit and coxl) and morphological observations demonstrated that N. ammophila and N. nidifica share a Glade but preliminary results show that they may not belong in the tribe Chondrieae.

We performed genome-wide association studies (GWAS) using the BovineSNP50 array to detect significant single nucleotide polymorphisms (SNPs) that may affect the concentration of 22 free amino acids and three peptides in Japanese Black beef cattle. A total of 574 Japanese Black cattle and 40,657 SNPs from the array were used for this study. Genome-wide significant SNPs were detected for β-alanine (three SNPs on chromosomes 22 and 29) and taurine (26 SNPs on chromosome 22). Importantly, the top two SNPs for taurine were highly significant (p = 6.2 × 10-21 ), and the frequency of the increase-concentration allele (Q) for taurine was found to be 0.73. The Q allele frequency of this population was similar to that of the other unrelated Japanese Black cattle, but different from that of the other breeds. In addition, the significant SNPs were not associated with carcass traits or fatty acid compositions. Interestingly, the top three of the four most significant SNPs for taurine were located near solute carrier family 6, member 6 (SLC6A6), which is a membrane transporter for taurine. We also found two associated variants in the 5'-upstream region of SLC6A6; however, they were less significantly associated than the SNPs from the BovineSNP50 array.

Three known secondary metabolites were isolated from the organic extract of Laurencia intricata. Their structures were identified by NMR and MS experiments and comparison with the literature data. An aromadendrane sesquiterpene, (+)-cyclocolorenone showed strong repellent activity against the maize weevil Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae) adults. It had the same activity as natural insecticides, pyrethrins, with a ED50 value of 2.0 mu g/cm(2). This is the first report of insect repellent activity of (+)-cyclocolorenone. The results suggest that the red alga Laurencia is a promising source of bioactive compounds which can be used as potential biocontrol agents for stored-product insects.

Historically Saccharina spp. beds occurred along the west coast of Hokkaido, an oligotrophic area, and were commercially exploited. Currently extensive commercial Saccharina spp. beds do not form due to nutrient limitations. Here, we postulate that nutrients assimilated by paleo-Saccharina spp. beds may have been derived from spawning herrings (Clupea pallasii) acting as organisms that formed a vector from their feeding grounds (Okhotsk Sea and Pacific Ocean) to their spawning area (west coast of Hokkaido, Japan Sea). To test this hypothesis we examined stable nitrogen isotope ratios (δ15N) of 100- to 135-year-old Saccharina specimens preserved at the Herbarium (Hokkaido University Museum). δ15N values of the paleo-Saccharina specimens collected from this region were in the range of 10‰, which is significantly higher than the current 3-7‰ in freshly sampled Saccharina spp. This high δ15N indicates that spawning herring (Clupea pallasii) had potentially been a significant source of dissolved inorganic nitrogen (DIN) absorbed by Saccharina, acting as an organism forming a vector for transporting nutrients from eutrophic to oligotrophic coastal ecosystems. Our findings support the hypothesis of so-called "herring-derived nutrients."

Top five clustering results obtained from the docking of inosine 5′-monophosphate into ecto-5′-nucleotidase by SWISSDOCK server. (XLSX 9 kb)

Association test of ecto-5′-nucleotidase (NT5E) with carcass traits and fatty acid compositions. (XLSX 12 kb)