A new prenylflavonoid isolated from propolis collected in the Solomon Islands

The new prenylflavonoid, solophenol A (1), together with three known compounds, bonannione A (2), sophoraflavanone A (3) and (2S)-5,7-dihydroxy-4'-methoxy-8-prenylflavanone (4), were isolated from propolis collected from Malaita Island in The Solomon Islands. The structure of each compound was determined by spectroscopic methods, including mass spectrometry and 2D NMR. Compound 1 exhibited potent 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activity.     

Chromis okamurai,a new damselfish from the Okinawa Trough,Japan

A new pomacentrid fish,Chromis okamurai, is described from a single specimen taken from the Okinawa Trough (25°53.4′N, 123°59.4′E), in 135–175 m. This species is most closely related to the deep-dwellingC. mirationis, sharing with it the same meristic data (in particular XIV dorsal spines and 2 upper and lower caudal spinules), large eye, and relatively deep body. It differs in having a small round posterior nostril (large and slit like inmirationis), longer second anal spine, shorter pelvic fins, and in color: two dark brown stripes on body and a pale pectoral-fin axil (mirationis has a single, midlateral, yellow to yellowish brown stripe which extends broadly onto lower part of caudal fin, and a black pectoral axil).     

A New Prenylated Flavonoid from Propolis Collected in Okinawa,Japan

The new prenylflavonoid, isonymphaeol-B (1), together with three known compounds, nymphaeol-A (2), nymphaeol-B (3), and nymphaeol-C (4), were isolated from propolis collected in Okinawa, the southern-most prefecture of Japan. The structure of each compound was determined by spectral methods, including mass spectrometry and 2D NMR. Each compound had 1,1-diphenyl-2-picryl-hydrazyl radical-scavenging activity.     

A validated spectrophotometric method for quantification of prenylated flavanones in pacific propolis from Taiwan

Introduction – Because of its chemical diversity, the only way to standardise propolis is to specify multiple standards for different propolis types according to the corresponding chemical profile. So far, this has been done only for European propolis. Objective – To develop a rapid low‐cost spectrophotometric procedure for quantification of bioactive prenylated flavanones in Taiwanese propolis. Methodology – The proposed method quantifies the total flavanones on the basis of their absorption as coloured phenylhydrazones formed by interaction with 2,4‐dinitrophenylhydrazine. The procedure was validated through model mixture of compounds representing the composition of Taiwanese propolis according to previous studies. The major flavanones of the propolis samples (propolins C, D, F and G) were quantified by HPLC. Antiradical activity against DPPH was also measured. The DNP (dinitrophenylhydrazine) spectrophotometric method is applied for the first time for quantification of prenylated flavanones. Results – Spectophotometric procedure applicable to new type propolis (Macaranga type) was developed with recovery between 105 and 110% at the concentration range of 0.573–1.791 mg/mL. Six propolis samples were analysed by spectrophotometry using the procedure developed and validated, and by HPLC as the results demonstrated satisfactory agreement. Neither the spectrophotometric data nor the values measured by HPLC showed significant correlation with the antiradical activity against DPPH. Conclusion – The proposed spectrophotometric procedure is useful for routine analyses of Macaranga‐type propolis, because of its simplicity, repeatability and acceptable accuracy. Its application to a number of commercial samples could be used as a basis for standardisation and quality control of Pacific propolis. Copyright © 2009 John Wiley & Sons, Ltd.     

A new species of scabbardfish, Evoxymetopon macrophthalmus (Scombroidei: Trichiuridae), from Okinawa, Japan

Evoxymetopon macrophthalmus sp. nov. is described on the basis of a single specimen collected off Okinawa Island, Ryukyu Islands, Japan. Among the two valid species of Evoxymetopon, the new species is more similar to E. poeyi in having the first dorsal-fin spine enormously large, compressed, and sword shaped. It differs from E. poeyi in having the upper profile of head uniformly convex without a prominent sagittal crest (vs. with a prominent sagittal crest), tip of first anal pterygiophore connected to the last rib in the anterior part, while the first hemal spine is long and connected to the posterior margin of pterygiophore bone plate (vs. connected to the first hemal spine only), a larger eye, 4.5 times in head length (vs. 5.5–5.9 times), 15 externally visible anal-fin soft rays (vs. 20), 9 upper gill rakers of the first arch (vs. 4–6), and 60 caudal vertebrae (vs. 64).     

Liopropoma dorsoluteum sp. nov., a new serranid fish from Okinawa, Japan

A new serranid fish,Liopropoma dorsoluteum sp. nov., is described on the basis of two specimens from Yaeyama Is., Okinawa, Japan. The new species is most similar toL. erythaeum Randall & Taylor, 1988, in having the following characters: Dorsal fin rays VIII, 12; anal fin rays III, 9; pored lateral line scales 52–53; anterior nostril situated midway between posterior nostril and anterior tip of snout; slightly forked caudal fin with both lobes rounded. It differs from the latter species in having a shorter pectoral fin (23.4–23.8% SL vs. 26.9–29.0% SL), greater preanus length (65.6–68.0% SL vs. 63.3–65.1% SL), fewer gill rakers (6+12 vs. 6–7+14–15) and yellow coloration on the back (vs. light red on head and body) in fresh specimens.     

Apterichtus keramanus, a new snake-eel from Okinawa, southern Japan (Ophichthinae, Ophichthidae)

A new snake-eel,Apterichtus keramanus, is described on the basis of a single 276-mm TL specimen trawled from the coast of Kerama Islands, Okinawa Prefecture, Japan. The species is unique in the genus in having the posterior nostril opening entirely inside the mouth and a dark band running from the anteroventral margin of the eye to the upper lip.     

A new genus and species of octocoral with aragonite calcium-carbonate skeleton (Octocorallia,Helioporacea) from Okinawa,Japan

A new genus and species of octocoral with a calcium-carbonate skeleton, Nanipora kamurai sp. n., is described from a shallow coral reef in Okinawa, Japan. Contrary to most octocorals, the skeleton is composed of crystalline aragonite as in blue coral Heliopora. The results of molecular phylogenetic analyses of sequences of mtMutS, COI, and ITS1-5.8s-ITS2-28S region suggest Nanipora gen. n. specimens should be included in order Helioporacea. Based on morphological results compared with other Helioporacea including the genus Epiphaxum (family Lithotelestidae), we establish the new genus Nanipora within Lithotelestidae. This is the first time that a close molecular phylogenetic relationship between Heliopora and a related genus within Helioporacea has been revealed.     

Tirumalin,a new prenylated dihydroflavonol from Rhynchosia cyanosperma

A new dihydroflavonol has been isolated together with the known flavonol-O- glycosides, rutin and kaempferol-3-rutinoside, and (+)-pinitol from the leaves of R. cyanosperma Benth. The dihydroflavonol was identified as (+)-(2R, 3R)-8-C-prenyltaxifolin-7, 4′-dimethyl ether on the basis of spectroscopic studies and the compound given the trivial name tirumalin.     

Rhus javanica var. chinensis as a new plant origin of propolis from Okayama, Japan

To directly identify the plant origin of propolis from Takebe-cho (Okayama, Japan), we observed the honeybee behavior. Honeybees scraped sap from the tree, Rhus javanica var. chinensis. We compared the constituents and radical-scavenging activity of this sap and propolis. Their chemical constituents and radical-scavenging activity were comparable. This indicates directly that the plant origin of this propolis is R. javanica var. chinensis.     

A new reefgoby,Priolepis duostella (Perciformes: Gobiidae) collected from off Kashiwa-jima Island,Kochi, Japan

Priolepis duostella sp. nov. (Perciformes: Gobiidae) is described based on a single specimen of 28.8 mm in standard length collected from an artificial reef released established for 2.5 years in ca. 100 m depth off Kashiwa-jima Island, Kochi, southern Japan. Within the three species grades of the genus, the new species is included in the “Priolepis profunda” grade, characterized by the presence of predorsal scales and well-developed transverse papillae rows on the cheek. The new species can be clearly distinguished from congeners by its distinctive coloration, including two black blotches, each crossed by a vertical white stripe, on the caudal fin, four white stripes on the head, and six white bars on body, the second bar curved, continuous with the anteriormost diagonal stripe on the first dorsal fin, the third bar bent at the middle, originating on the second dorsal-fin origin, and the fourth bar curved. Although most similar in coloration to Priolepis akihitoi Hoese and Larson 2010, the new species can be distinguished from the latter by the following: a large eye, its diameter 31.4% of head length (HL) (vs. 26.1–30.3), a wide interorbital space, its width 10.9% HL (vs. 5.3–7.8), six bars on the body, second to fourth curve or bent (vs. eight, all straight), black blotches on the lower caudal fin (vs. absent), and three anterior transverse interorbital papillae (ATI) (vs. one or two); and four or five posterior transverse interorbital papillae (PTI) (vs. one or two).

     

A new species of Labidocera (Copepoda,Calanoida, Pontellidae) collected from Okinawa,southwestern Japan,with establishment of five Indo-West Pacific species groups in the L. detruncata species complex

Labidocera churaumi sp. n. is described from Okinawa, southwestern Japan. The female of the new species differs from other congeners in genital compound somite with right postero-lateral and left antero-lateral processes. The male is distinguished from other congeners by the structure of the fifth leg. This new species is assigned to a newly proposed species group, the Labidocera madurae species group, within the Labidocera detruncata species complex. In this species complex five Indo-West Pacific species groups are recognized (cervi, detruncata, gangetica, madurae, and pavo) and defined on the basis of difference in sexual dimorphism.     

A new species of Enterognathus (Copepoda, Cyclopoida, Enterognathidae) collected from the Seto Inland Sea, western Japan

A new species of the endoparasitic copepod Enterognathus (Cyclopoida, Enterognathidae) is described from a crinoid host in the Seto Inland Sea, western Japan. This is a third species of the genus and its first occurrence in the Pacific Ocean. The new species is distinguished from two previously known congeners by the morphology of the body somites, caudal rami, antennae and legs. Crinoid parasites belonging to Enterognathus and the closely related genus Parenterognathus have a broad distribution from the northeastern Atlantic through the Red Sea to the West Pacific.     

Mitochondrial toxicity and antioxidant activity of a prenylated flavonoid isolated from Dalea elegans

The prenylated flavanone 2'-4'-dihidroxy-5'-(1" '-dimethylallyl)-6-prenylpinocembrin) (6PP), isolated from the roots of Dalea elegans, shows antimicrobial activity. The aim of this study was to evaluate mitochondrial toxicity and antioxidant properties of 6PP. Addition of micromolar concentrations of 6PP to rat liver mitochondria, stimulated O2 uptake in state 4 and inhibited it in state 3 when malate-glutamate was the respiratory substrate, and inhibited O2 uptake in state 3 when succinate was the substrate. Highest concentration of 6PP also inhibited O2 uptake in state 4 in the latter case; in both conditions, respiratory control index values were decreased. This flavanone collapsed the mitochondrial membrane potential in a concentration-dependent manner. 6PP also inhibited F0F1-ATPase activity in coupled mitochondria and in submitochondrial particles. In the latter, this compound also inhibited NADH oxidase and succinate dehydrogenase activities. HEp-2 cells were incubated for 24 h with 6PP in presence or absence of 0.5% albumin. As measured by reduction of the mitochondrial-related probe MTT, in the albumin-free condition, 6PP was cytotoxic in a concentration-dependent manner; on the other hand, albumin decreased 6PP effect. In addition, in rat liver microsomes 6PP: (1) inhibited the enzymatic lipid peroxidation, (2) exhibited significant scavenging activity, measured by DPPH reduction assay and (3) demonstrated significant antioxidant activity by decreasing the reduction of Mo(VI) to Mo(V). We suggest that 6PP impairs the hepatic energy metabolism by acting as mitochondrial uncoupler and by inhibiting enzymatic activities linked to the respiratory chain. 6PP also exerts both antioxidant and antiradical activities. Due to its cytotoxicity, this molecule, and its future structure developments, can be considered as a potentially promising therapeutic agent, for instance in cancer chemotherapy.     

Antifungal activity of a prenylated flavonoid from Dalea elegans against Candida albicans biofilms

BackgroundThe continuing emergence of infections with antifungal resistant Candida strains requires a constant search for new antifungal drugs, with the plant kingdom being an important source of chemical structures.PurposeThe present study investigated the antifungal effect of 2′,4′-dihydroxy-5′-(1′′′,1′′′-dimethylallyl)-8-prenylpinocembrin (8PP, formerly 6PP), a natural prenylflavonoid, on Candida albicans biofilms, and compared this with an azole antifungal (fluconazole) by studying the cellular stress and antioxidant response.Study design/methodsThe fluconazole sensitive (SCa) and azole-resistant (RCa) C. albicans strains were used, with biofilm formation being studied using crystal violet (CV) and confocal scanning laser microscopy (CSLM). The minimal inhibitory concentration for sessile cells (SMIC) was defined as the concentration of antifungal that caused a 50% (SMIC 50) and 80% (SMIC 80) reduction of treated biofilms. The reactive oxygen species (ROS) were detected by the reduction of nitro blue tetrazolium (NBT), and reactive nitrogen intermediates (RNI) were determined by the Griess assay. The activities of the superoxide dismutase (SOD) and catalase (CAT) antioxidant enzymes and the total antioxidant capacity of the biofilms were measured by spectrophotometric methods. ROS accumulation was also detected inside biofilms by using the fluorogenic dye 2′,7′-dichlorodihydrofluorescein diacetate (DCFH-DA), which was visualized by CSLM.ResultsThe SCa and RCa biofilms were strongly inhibited by 8PP at 100 µM (SMIC 80). We observed that cellular stress affected biofilms growth, resulting in an increase of ROS and also of reactive nitrogen intermediates (RNI), with SOD and CAT being increased significantly in the presence of 8PP. The basal level of the biofilm total antioxidant capacity was higher in RCa than SCa. Moreover, in SCa, the total antioxidant capacity rose considerably in the presence of both 8PP and fluconazole.ConclusionOur data suggest that 8PP may be useful for the treatment of biofilm-related Candida infections, through an accumulation of endogenous ROS and RNI that can induce an adaptive response based on a coordinated increase in antioxidant defenses. 8PP may also have a therapeutic potential in C. albicans infections.     

Two new species of Asellota (Crustacea,Isopoda) from coral reefs on Iriomote Island,Okinawa, Japan

Pleurocope iriomotensis sp. n. and Prethura tuberculata sp. n. are described from Iriomote Island, Ryukyu Archipelago, southern Japan. These are the first records of Pleurocope from the Pacific and of Prethura from the Asian Pacific coast. Pleurocope iriomotensis differs from its congeners in having lateral spine-like processes on pereonite 4 and coxal plates of pereonite 7. Prethura tuberculata can be distinguished from its single congener in having a lateral short projection of protopod of pleopod 2.     

Three species of rust fungi (Uredinales) from Okinawa,Japan

Three species of rust fungi were reported based on the specimens collected in the islands of the Yaeyama group and Okinawa, Japan.Puccinia tarennicola onTarenna gracilipes andUredo daphniphylli onDaphniphyllum teijsmannii were described as new species.Villebrunea frutescens was added to the host plants ofUredo pipturi. Contribution No. 115, Laboratories of Plant Pathology and Mycology, Institute of Agriculture and Forestry, University of Tsukuba.