Tsuyoshi Abe's research while affiliated with Hokkaido University and other places
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Publications (48)
Colpomenia borea sp. nov. is described from Hokkaido, Japan and Magadan, Far East Russia based on morphological observations and molecular analyses using mitochondrial cox3 and chloroplast rbcL 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 co...
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 triterpe...
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 halogenate...
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....
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).
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 na...
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-chamig...
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:...
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 fr...
Figure A. Geographical distribution of Liagora japonica based on the herbarium specimen deposited in SAP and TNS. Detail of collection data is shown in Tables A and B in S2 File. Figure B. Bayesian tree based on psaA gene sequences. Numbers on the branches indicate the corresponding posterior probabilities (PP, left) from Bayesian analysis and boot...
Liagora japonica is a red algal species distributed in temperate regions of Japan. This species has not been collected from its type locality on the Pacific coast of Japan since 1927 and seems to have become extinct in this area. For molecular characterization of L. japonica, we extracted DNA from the topotype material of L. japonica collected in 1...
The DNA extraction and sequencing procedures for modern specimens.
(DOCX)
Table A. Collection and herbarium information for specimens of Liagora japonica used in the morphological analyses that have no molecular data. Table B. Collection locations and details, and GenBank accession numbers of samples used in the psaA, psaB, psbA, rbcL, COI, 18S rRNA, and 28S rRNA genes analyses. Table C. GenBank accession numbers of spec...
The brown algal genus Acinetospora is characterised by sparsely branched uniseriate filaments, scattered meristematic zones, short laterals (“crampons”) and scattered reproductive organs. The morphology and life history of the generitype A. crinita have been studied repeatedly, and accounts of the species’ highly varied reproductive patterns were a...
Natural antifouling products have been the subject of considerable attention. We screened marine algae for antifouling activity and discovered omaezallenes, the new bromoallene-containing natural products isolated from the red alga Laurencia sp. Described is the isolation, structure elucidation, and total syntheses of omaezallenes. The relative and...
A new red alga, Dasya enomotoi, is described from Japan. This species is characterized by having a large thallus consisting of an elongated axis and many, radially arranged, polysiphonous branches both of which are heavily corticated and densely covered with numerous, soft monosiphonous filaments. It is distinguished from several similar species by...
The title compound {systematic name: (1R,4S,4aS,7R,8aR)-4-bromo-7-[(1S,3R)-3-bromo-1,2,2-trimethyl-cyclo-pent-yl]-1,4a-dimethyl-deca-hydro-naphthalene-1,7,8a-triol}, C(20)H(34)Br(2)O(3), is a neoirieane-type bromo-diterpenoid isolated from Laurencia yonaguniensis Masuda et Abe, species inedita. The absolute stereochemistry was established as (1S,4R...
The production of labeled brominated metabolites with radioactive (82)Br in Laurencia species was investigated as part of a study of the biosynthesis of halogenated metabolites from species belonging to the red algal genus Laurencia (Rhodomelaceae, Ceramiales). Radiobromide [(82)Br], thin-layer chromatography (TLC), and TLC-autoradioluminography (A...
During our studies on Malaysian Laurencia species, brominated metabolites, tiomanene, acetylmajapolene B, and acetylmajapolene A were isolated from an unrecorded species collected at Pulau Tioman, Pahang along with known majapolene B and majapolene A. Acetylmajapolene A was a mixture of diastereomers as in the case of majapolene A. Tiomanene may be...
Many morphologically similar, but chemically distinct, populations have been found in the marine red alga Laurencia nipponica Yamada (Rhodomelaceae, Ceramiales) growing in Japan. Each chemical type is characterized by a specific end-product of halogenated secondaly metabolite synthesis: chamigrane-type sesquiterpenoids such as prepacifenol and halo...
The title compound, neoirietetraol (C20H34Br2O4), was isolated from the Okinawan red alga Laurencia yonaguniensis. The crystal belongs to space group P21 with cell dimensions a=8.1048(1), b=15.3013(3), c=10.7455(3)Å and β=102.337(1)°. The absolute stereochemistry of the title compound was established as (1S, 4R, 5R, 7R, 10S, 11R, 12S, 14R). 2007
Morphological and molecular phylogenetic studies were made on recently collected Halymenia plants widely from Japan, the Philippines, Indonesia, Malaysia and Thailand. Although the external morphology (branching pattern, blade width, or degree of dentation) was very variable, no special differences were found in their vegetative and reproductive st...
A molecular phylogenetic analysis of three closely related red algal genera, Laurencia, Chondrophycus and Osmundea (Rhodomelaceae) that are often called the Laurencia complex or Laurencia sensu lato, mainly of the north-western Pacific species, was carried out based on rbcL gene sequences. The sequence data downloaded from GenBank were also include...
Genetic variation in the synthesis of halogenated secondary metabolites in the Japanese marine red alga Laurencia nipponica Yamada (Rhodomelaceae, Ceramiales) has been investigated in laboratory crossing experiments and chemical analyses, F1 tetrasporophytes and F1 gametophytes resulting from crosses within chemical races produced major metabolites...
The red alga Laurencia brongniartii J. Agardh (Rhodomelaceae, Ceramiales) is characterized by: (i) the production of four periaxial cells from each vegetative axial segment; (ii) the presence of two or three corps en cerise per superficial cortical cell and one per trichoblast cell; (iii) the production of a single tetrasporangium-bearing periaxial...
The red alga Laurencia nipponica Yamada (Rhodomelaceae, Ceramiales) is known to contain several chemical races, each of which is characterized by a particular, major halogenated secondary metabolite. Both field-collected and cultured plants of a population of this species found recently at Shikanoshima Island, Fukuoka Prefecture, southern Japan, pr...
The halogenated secondary metabolite constitution of four species of the red algal genus Laurencia (Rhodomelaceae) from southern Japan is reported. Laurencia composita Yamada from Tanegashima Island (Kagoshima Prefecture) bears five sesquiterpenoids (2,10-dibromo-3-chloro-α-chamigrene and 2,10-dibromo-3-chloro-9-hydroxy-α-chamigrene, in addition to...
Further investigation of Laurencia species from Japanese waters, which were collected at three locations, yielded brominated metabolites, a labdane- type diterpene and a C15 acetogenin possessing a terminal bromoallene group. Their structures were deduced from analysis of spectroscopic data.
Hypnea cornuta (Kützing) J. Agardh var. stellulifera J. Agardh (Hypneaceae, Gigartinales) is distinguished from the type variety by the short, thick, rigid axes that produce thick adventitious branchlets as well as the tetrasporangial sori and spermatangial sori that extend to the parental axis and branches. Var. stellulifera is raised to the rank...
Two halogenated C(15) acetogenins, itomanallenes A and B, with a terminal bromoallene moiety along with a halogenated sesquiterpene, itomanol, have been isolated from the red alga Laurencia intricata collected in Okinawan waters. Their structures were deduced from 1D and 2D NMR experiments including (1)H-(1)H COSY, HSQC, HMBC, and NOESY methods. Th...
From an unidentified species of Laurencia collected from Okinawan waters two novel brominated metabolites, 1 and 2, along with known halogenated compounds, 2,10-dibromo-3-chloro-alpha-chamigrene (3) and microcladallene A (4), were isolated and identified. The structures of these new compounds were established as ent-labdane-type bromoditerpenes, (1...
A novel brominated diterpene based on the rare neoirieane skeleton, named neoirietetraol (1), has been isolated along with a halogenated C15 acetogenin, (3Z)-laurenyne (2), from a new Laurencia species, L.yonaguniensis Masuda et Abe, species inedita, collected at Yonaguni Island, Okinawa Prefecture, Japan. The structures of these metabolites were e...
The chemical compositions of five species of the red algal genus Laurencia from coastal waters of Okinawa Prefecture, Japan, have been investigated. A halogenated C(15) acetogenin, (12E)-lembyne-A, was isolated from L. mariannensis, and a halogenated sesquiterpene, (6R,9R,10S)-10-bromo-9-hydroxy-chamigra-2,7(14)-diene, was first found from L. majus...
Two halogenated C15 acetogenins, named lembyne-A and lembyne-B, have been isolated from an unrecorded Laurencia species collected off the Malaysian waters. Their structures were deduced on the basis of spectroscopic evidence. Previously known elatol and iso-obtusol showed potent antibacterial activity against some marine bacteria.
In connection with our chemotaxonomic studies of Malaysian species of the red algal genus Laurencia, the chemical composition of Laurencia pannosa Zanardini was examined. Two halogenated sesquiterpenoids, named pannosanol (1) and pannosane (2), have been isolated along with a halogenated C15-acetogenin, (3Z)-chlorofucin (3). The structures of these...
Two novel halogenated C15 acetogenins, named bisezakyne-A and -B, have been isolated along with dactylyne from an undescribed species of the red algal genus Laurencia collected from Japan. The structures of these compounds were elucidated by spectroscopic data.
Two brominated C15 nonterpenoid compounds, japonenyne-A and -B, with a novel 2,7-dioxabicyclo [4.3.0]nonane skeleton have been isolated from the red alga Laurencia japonensis Abe et Masuda. The structures of these metabolites were deduced from spectral evidence.
A new brominated, anhydroaplysiadiol has been isolated from a new Laurencia species, L. japonensis Abe et Masuda sp. ined., along with aplysiadiol and 2,10-dibromo-3-chloro-α-chamigrene. The last two compounds are commonly found in this species collected from various localities. The structure of anhydroaplysiadiol was deduced from spectral evidence...
The marine red alga Laurencia japonensis sp. nov. (Rhodomelaceae, Ceramiales) is described from the warm temperate region of Japan. It is characterized by the following combination of features: (1) terete, rigidly cartilaginous, upright axes arising from a primary discoid holdfast and stolen-like branches; (2) tristichous branching; (3) penultimate...
Two red algal species, Laurencia composita Yamada and L. okamurae Yamada (Rhodomelaceae, Ceramiales), that grow in Japanese waters have often been confused with each other being similar in gross morphology. They can be morphologically distinguished by branching pattern (polystichous in L. composita and tristichous in L. okamurae) and the frequency...
Citations
... On the other hand, some species without "corps en cerise" produce no halogenated compound. To date, the chemical constitution of 22 species of Japanese Laurencia with "corps en cerise", including 7 taxonomically undescribed species, have been investigated [8][9][10][11]. ...
... 402 C 15 acetogenins are common metabolites of red algae, with reports of two new compounds each from Laurencia japonensis 902, and 903 and L. nangii 904, and 905, respectively. 403,404 Teanol 906 is a dibromo-sesquiterpenoid that exhibits weak brine shrimp lethality, 405 while six new structurally diverse halosesquiterpenoids 907-912 were reported from L. composita. 406 Eight new halo-diterpenoids 913-920 were isolated from a Sphaerococcus species. ...
Reference: Marine natural products
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... Among them L. intricata contained zagashimallene (4), cyclocolorenone (5), and intricatetraol (6) [13]. L. japonensis contained two new brominated acetogenins katsuurenyne A (7) (Fig. 1) and katsuurenyne B (8) along with known 2,10-dibromo-3-chloro-α-chamigrene (9) and aplysiadiol (10) [14]. Furthermore, in the coast of Yoshio, L. okamurae unusually grow sympatrically in morphological variation, a clumpy type and a non-clumpy type. ...
... In EO samples from these localities the content of cyclocolorenone was highest. The cyclocolorenone showed strong repellent activity against the maize weevil Sitophilus zeamais (Motschulsky 1855) adults, comparable to pyrethrins as natural insecticides (13). In the EO samples from the localities without the repellent activity bornyl acetate was dominant. ...
... Molecular phylogenetic analysis of rbcL gene sequences revealed a tree topology largely consistent with those reported by Sutti et al. [37] and Díaz-Tapia et al. [18]. Neochondria was resolved as sister to the Laurencieae and Chondrieae in both this study and Sutti et al. [37] (and was not addressed in Díaz-Tapia et al. [18]), suggesting either that Neochondria requires re-assignment to its own tribe, or that the two tribes should be merged. ...
... With the rise of genomic data (i.e., rapid increase in the number of available organelle genomes), Ulva taxonomy is entering a new era. Next-generation sequencing is a promising avenue for generating amplicons from old type specimens (Bunning et al. 2012;Prosser et al. 2016;Suzuki et al. 2016;Forin et al. 2018;Hughey et al. 2019). The mitochondrial and chloroplast genomes of several species are available (Table S6), as well as the whole genomes of U. compressa and U. prolifera (De Clerck et al. 2018;He et al. 2021). ...
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... • Kim & Lee (1994, fig. 1A • Similar species: Acinetospora filamentosa (Noda) Yaegashi et al. (2015, fig. 2), a species originally described with ellipsoidal (not globose) unangia (Noda, 1970, fig. ...
... Laurencia okamurae grows from subtropical to cold temperate regions of the Northwestern Pacific (Masuda, Abe, Suzuki, & Suzuki, 1996;Saito, 1989). Crossing tests using cultured strains indicated that L. okamurae is reproductively incompatible with L. nipponica (Abe & Masuda, 1998). The major secondary metabolites produced by the two species differ considerably. ...
... On the other hand, some species without "corps en cerise" produce no halogenated compound. To date, the chemical constitution of 22 species of Japanese Laurencia with "corps en cerise", including 7 taxonomically undescribed species, have been investigated [8][9][10][11]. ...
... We amplified and sequenced a portion of rbcL gene by using two pairs of primers: rbcL-Rh1 and Rh5, rbcL-Rh1 and rbcS1 (Yamagishi and Masuda 2000, Hanyuda et al. 2004. PCR procedures followed Yamagishi et al. (2014), and then PCR products were purified by polyethylene glycol (PEG) (Sigma-Aldrich Co, Tokyo, Japan) precipitation (Rosenthal et al. 1993). PCR products were sequenced using a BigDye Terminator v.1.1 ...
