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Plants protect themselves against various stresses by using volatile terpenes, which are also key precursors of climate‐relevant constituents in the atmosphere. Conifers store terpenes in storage pools, which serve as emission sources. However, how leaf terpene contents influence the quantity and composition of emissions is uncertain. Here, we examined whether they explain the profile of terpene emissions by using the measurements of 6 monoterpenes and 2 diterpenes stored in and emitted from the same branches of 10 local populations in Japanese cedar (Cryptomeria japonica), a common conifer in Japan. We estimated partial pressures of terpenes from leaf terpene contents by using a thermodynamic algorithm. The estimates correlated well with emissions of monoterpenes, suggesting the release of monoterpenes from the storage pools. High tree‐to‐tree variations in emissions of individual terpenes did not correlate with variations in concentrations of corresponding terpenes in leaves. Diterpenes (ent‐kaurene and phyllocladene) were emitted in most cases when individual trees held corresponding diterpenes, suggesting a linkage between emissions and storage pools, but the emissions were not explained by the algorithm owing to their low vapor pressure. [ABSTRACT FROM AUTHOR]

Determining the mechanisms of pine wilt disease (PWD) resistance in Pinus is a popular research topic, but information on volatile organic substances (VOS) and their role in PWD is lacking. Whether the difference in VOS among Pinus thunbergii parl. that have different levels of resistance with pine wood nematodes (PWNs) is the reason for the differing resistance needs to be studied. In this study, resistant P. thunbergii introduced from Japan and susceptible P. thunbergii native to China were used to investigate the effects of different lines inoculated with PWN. We determined the expression levels of the terpene synthesis-related genes geranylgeranyl diphosphate synthase (GGPPS), 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 (HMDH1), two kinds of alpha-farnesene synthase (PT) genes. The types and the relative percentage content of terpenoids in the pine needles were also determined by gas chromatography coupled with mass spectrometry (GC-MS). Results show that the growth, population size and migration of PWNs were significantly inhibited. The expression of terpene synthesis genes in the resistant P. thunbergii was higher than that in the susceptible one. The analysis of terpenoids revealed a total of 41 terpenoids, of which resistant P. thunbergii contained 39 and susceptible P. thunbergii only 28; 14 terpenoids were specific to resistant P. thunbergii, in which 8 of the terpenoids were constitutive terpenes and 6 were inducible terpenes. There were 3 terpenes unique to the susceptible P. thunbergii, and only 1 inducible terpene. Our results showed that the reduction in the expression of disease symptom and suppression of PWNs in resistant P. thunbergii was likely related to differences in the types and content of resistance-related substances in the trees. This study does not specifically connect elevated compounds in resistant P. thunbergii to resistance to PWN and assays should be conducted to establish direct effects of terpenoids on pinewood nematode activity and reproduction. [ABSTRACT FROM AUTHOR]

We postulated that disinfection of viable Trichophyton species in shoes would help reduce the number of patients with tinea pedis in Japan and that this might be accomplished safely using volatile components of essential oils. As vapor of lemongrass (Cymbopogon citratus) oil and citral have strong antimicrobial activities against Trichophyton, we examined the conditions under which lemongrass oil or citral show optimal antimicrobial activity in shoes. First, we investigated whether or not a strong antimicrobial effect could be obtained by combining with terpene aldehydes or aromatic aldehydes. When combined with citral, perillaldehyde showed superior antimicrobial activity to citronellal, cinnamaldehyde, cuminaldehyde, hydroxycitronellal, and vanillin. The combined effects of citral and perillaldehyde against Trichophyton mentagrophytes, Bacillus subtilis, and Candida albicans as volatile components dotted on filter paper placed away from the petri dish inoculated with fungi or bacteria were examined. Citral (2.5 mg/mL) and perillaldehyde (2.5 mg/mL) showed a greater inhibitory effect on growth of C. albicans than either solution alone in the aromatogram (disc diffusion) descent method (fractional inhibitory concentration [FIC] index of 0.58). Citral (2.5 mg/mL) and perillaldehyde (1.25 mg/mL) vapors in a closed box synergistically inhibited growth of B. subtilis and T. mentagrophytes (FIC indexes of 0.5 and 0.38, respectively). These results suggested that this combination would be safe and useful for disinfection of shoes. [ABSTRACT FROM AUTHOR]

Aconitum carmichaelii is a high-value medicinal herb widely used across China, Japan, and other Asian countries. Aconitine-type diterpene alkaloids (DAs) are the characteristic compounds in Aconitum. Although six transcriptomes, based on short-read next generation sequencing technology, have been reported from the Aconitum species, the terpene synthase (TPS) corresponding to DAs biosynthesis remains unidentified. We apply a combination of Pacbio isoform sequencing and RNA sequencing to provide a comprehensive view of the A. carmichaelii transcriptome. Nineteen TPSs and five alternative splicing isoforms belonging to TPS-b, TPS-c, and TPS-e/f subfamilies were identified. In vitro enzyme reaction analysis functional identified two sesqui-TPSs and twelve diTPSs. Seven of the TPS-c subfamily genes reacted with GGPP to produce the intermediate ent -copalyl diphosphate. Five AcKSLs separately reacted with ent -CPP to produce ent -kaurene, ent -atiserene, and ent -13- epi -sandaracopimaradie: a new diterpene found in Aconitum. AcTPSs gene expression in conjunction DAs content analysis in different tissues validated that ent -CPP is the sole precursor to all DAs biosynthesis, with AcKSL1, AcKSL2s and AcKSL3-1 responsible for C 20 atisine and napelline type DAs biosynthesis, respectively. These data clarified the molecular basis for the C 20 -DAs biosynthetic pathway in A. carmichaelii and pave the way for further exploration of C 19 -DAs biosynthesis in the Aconitum species. A Pacbio full-length transcriptome of Aconitum carmichaelii were publicly available. Twelve diterpene synthases were functional identified to responsible for atisine, napelline type diterpene alkaloids (DAs) and ent -13- epi -sandaracopimaradie biosynthesis, respectively. [Display omitted] [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

Tricholoma anatolicum collected from Turkey is consumed by public and exported to Japan every year. It was previously identified as Tricholoma caligatum until it was recognized as a new species. In the existing literature, there is no information on the aromatic composition of T. anatolicum. Therefore, in this study it was aimed to identify the volatile composition of T. anatolicum together with T. caligatum. Species identification was confirmed using molecular analyses based on ITS rDNA sequencing. Volatile compounds of both mushroom species were extracted using liquid-liquid extraction method and determined by Gas Chromatography-Mass Spectrometry-Flame Ionization Detector (GC-MS-FID). In the two Tricholoma species, 31 volatiles were obtained and grouped in seven chemical classes. The amounts of alcohols, volatile acids and esters were found to be higher in T. anatolicum, whereas the amounts of terpenes were detected as higher in T. caligatum. 1-Octen-3-ol responsible for the mushroom-like odour was only found in T. anatolicum. [ABSTRACT FROM AUTHOR]

Abstract Background We conducted a multicenter phase I/II trial of olaparib plus eribulin in Japanese patients with advanced or metastatic triple-negative breast cancer (TNBC) to determine the recommended phase II dose (RP2D) (phase I) and to examine the efficacy and safety (phase II) (UMIN00009498) of the combined therapy. Patients and methods In phase I, olaparib tablet was orally administered twice daily from level 1:25 mg BID to level 7:300 mg BID, with 1.4 mg/m2 of eribulin on days 1 and 8. In phase II, patients were treated with RP2D to assess the response rate (independent review). The planned sample size was 24 with a threshold of 10%. Results One of the 24 patients enrolled in phase I experienced dose-limiting toxicity. The RP2D was established as 300 mg twice daily for olaparib and 1.4 mg/m2 for eribulin. Among the 24 patients in phase II, the median number of administered courses was 5.5 (range: 1–28). Grade ≥III adverse events included neutropenia (83.3%), leucopenia (83.3%), anaemia (41.7%), febrile neutropenia (33.3%) and thrombosis (8.3%). The response rate was 29.2% (independent; N = 7/24; 90% confidence interval [CI]; 14.6–47.9). Median progression-free survival and overall survival were 4.2 (95% CI, 3.0–7.4) and 14.5 (95% CI, 4.8–22.0) months, respectively. Germline BRCA1/2 mutation status was observed in three patients in phase I and 2 patients in phase II, respectively. The C max and area under the curve for olaparib increased in a dose-dependent manner, and these parameters for eribulin and olaparib were not influenced by each other. Conclusions Combination therapy of olaparib with eribulin shows antitumour activity against advanced or metastatic TNBC, but caution must be exercised in the presence of febrile neutropenia. Highlights • Olaparib combined with eribulin showed efficacy in patients previously treated with anthracycline and taxanes. • In pharmacokinetics, no drug interaction between eribulin and olaparib was observed. • Poly(ADP-ribose) polymerase inhibition was observed from the lowest dose of olaparib. [ABSTRACT FROM AUTHOR]

This study investigated the effect of pairing of wine vinified from shade-grown grapes before onset of ripening on the palatability of sashimi, a typical Japanese cuisine. GC-MS analyses of volatile chemicals revealed that shading reduced phenolic compounds and terpenoids, and added fatty acid ethyl esters which are also known to contribute to the flavor of Japanese sake. When the pairing of sashimi with wine was evaluated by individuals who regularly drink Japanese sake during meals, shade wine was more highly rated than wine made from normally-grown grapes. [ABSTRACT FROM AUTHOR]

Ethnopharmacological relevance Artemisia asiatica Nakai (Compositae) has a long history as a traditional remedy. Preparation from various parts of the plant (aerial parts and leaves) are used to treat a wide range of diseases including gastric trouble, liver dysfunction, and skin inflammation. Aims of this review The aims of this review were: 1) to provide an overview of recent studies and progress on A. asiatica -derived ethnopharmacological compounds and their pharmacological activities; and 2) to summarize existing evidence and provide insight for future studies. Materials and methods This investigation was carried out by analyzing published books and research papers via scientific databases, namely Science Direct, PubMed ACS Publication, Wiley Online Library, CNKI and information obtained online. The keywords “ Artemisia asiatica traditional uses,” “Compounds isolated and studied in Artemisia asiatica, ” and “Pharmacological advances in Artemisia asiatica ” were used and articles published between 1995 and 2017 were considered. In total, 500 works related to biological activities of A. asiatica were identified, and only materials published in English were included in the review. Results Comparative analysis of literature searched through sources available confirmed that the ethnopharmacological use of A. asiatica was recorded in Korea, China, and Japan. Phytochemical studies revealed the presence of flavonoids, sesquiterpene lactones, monoterpenes, and steroids in A. asiatica . Of these, flavonoids have been shown to exhibit significant pharmacological effects such as gastroprotective, anti-inflammatory, anti-tumor, and anti-microbial actions. Conclusions Phytochemical and pharmacological studies of Artemisia asiatica have proven that this plant is one of valuable medicinal sources with neuroprotective, gastroprotective, anti-oxidative, anti-inflammatory, and anti-cancer effects. Although ethanol extract of this plant is now being prescribed as gastroprotective and anti-ulcerative medicine, it is now time to expand its application to other human inflammatory diseases such as pancreatitis and hepatitis and further extensive study on toxicity in human. Therefore, the present review will encourage further studies of A. asiatica in the pursuit of wide range of therapeutic remedy. [ABSTRACT FROM AUTHOR]

A new gridded database has been developed to estimate the amount of isoprene, monoterpene, and sesquiterpene emitted from all the broadleaf and coniferous trees in Japan with the Model of Emissions of Gases and Aerosols from Nature (MEGAN). This database reflects the vegetation specific to Japan more accurately than existing ones. It estimates much lower isoprene emitted from other vegetation than trees, and higher sesquiterpene emissions mainly emitted from Cryptomeria japonica , which is the most abundant plant type in Japan. Changes in biogenic emissions result in the decrease in ambient ozone and increase in organic aerosol simulated by the air quality simulation over the Tokyo Metropolitan Area in Japan. Although newly estimated biogenic emissions contribute to a better model performance on overestimated ozone and underestimated organic aerosol, they are not a single solution to solve problems associated with the air quality simulation. [ABSTRACT FROM AUTHOR]

Ethnopharmacological relevance The plants in the genus Carpesium , which grow naturally in Asia and Europe, have long been used in traditional Chinese, Korean and Japanese medicines. The antipyretic, antimalarial, haemostatic, anti-inflammatory and detoxifying properties of their extracts enabled their use in the treatment of several diseases, such as fevers, colds, contusions, diarrhoea, mastitis, mumps, hepatitis, malaria, etc. This review summarises the state-of-the-art and comprehensive information surrounding its use as traditional medicine, phytochemistry, pharmacology, and toxicology to reveal the potential therapeutic effects of Carpesium plants and to establish a solid foundation for directing future research. Materials and methods The extensive reading and investigation were actualised by systematically searching the scientific literatures including Chinese, Korean and Japanese herbal classics, library catalogs and scientific databases (PubMed, Scopus, SciFinder and the Web of Science), were systematically searched for topics related to factors like the chemical constituents, pharmacognostic research and pharmacological effects of the Carpesium species. Results Carpesium plants have been studied extensively as traditional folk medicines in China, Korea and Japan all the time. In past, phytochemical research was the focal point of this genus, and the recent studies of the members of this genus have been focused on the pharmacological activity and potential therapeutic applications of these plants. The research performed revealed that 143 compounds including sesquiterpenoid lactone monomers, sesquiterpenoid lactone dimers, monoterpenes, diterpenoids, phenolic compounds, and several other type of compounds, were isolated and identified within this genus in recent years, and certain of these constituents had demonstrated to possess anti-inflammatory, anti-tumor, anti-plasmodial, anti-oxidant, anti-fungal and anti-bacterial effects. Conclusions This review shows that approximately 50 active compounds possess therapeutic potential during the treatment of cancer, inflammatory, parasitosis, etc. However, apart from those bioactive molecules, a considerable part of compounds, including a lot of sesquiterpenes, and several other type of compounds that have been previously isolated but have not been tested biologically need to be further tested. Therefore, more pharmacological experiments should be focused on these untested chemical constituents. Additionally, another issue concerns that most pharmacological studies were only performed in vitro-based experiments, so additional in vivo tests in animal models are required to estimate their side effects for the safety approval of therapeutic applications. Finally, further studies through well controlled, double-blind clinical trials are required to re-evaluate their efficacious and possible side effects, and more pharmacological mechanisms on main active compounds will also be needed for illuminating correlations between ehnopharmacology and pharmacology in future. [ABSTRACT FROM AUTHOR]

Cantharidin is produced by beetles of only two families, the Meloidae and the Oedemeridae. This substance is a defensive terpenoid that is toxic to the enemies of the beetles. Cantharidin also attracts other groups of insects and has been used as a bait to trap them. Cantharidin-baited traps deployed in central Japan captured coleopterans (Anthicidae, Endomychidae, Pyrochroidae, and Scarabaeidae), dipterans (Ceratopogonidae), hymenopterans (Formicidae), and harvestmen (Podoctidae). The seasonal occurrences of these arthropods, their sex ratios, known feeding choices, and mating habits suggest three possible underlying reasons for the attractancy of cantharidin: (i) it is accumulated as a defense against enemies and sometimes for transfer from males to females as a nuptial gift; (ii) it is used as a chemical cue in food searching; and (iii) it is used as an aggregation pheromone by mature arthropod individuals. The group of canthariphilous arthropods we describe represents a cryptic ecological assemblage with rare chemical networking among apparently unrelated species. [ABSTRACT FROM AUTHOR]

Abstract: We investigated terpenoid biomarkers in muds from lignite seams, clays from porcelain clay beds that slightly contain lignite, and from a conifer cone macrofossil from the Miocene Tokiguchi Porcelain Clay Formation of the Tokai Group in central Japan, as well as extant cones. The n-alkanes, n-alkanols (suberin origin), diterpenoids (conifer origin), hopanoids (bacteria origin) and steroids were mainly present in the lignite-containing muds and clays. On the other hand, the diterpenoids, triterpenoids (angiosperm origin), hopanoids and steroids were detected as major component in the conifer cone macrofossil. In addition, the diterpenoids were mainly detected in the extant conifer cones. The low hopane isomer ratios and the detection of biosterols are confirmed to be immature in the lignite, sediment and macrofossil in the formation. The stanol/sterol ratio values of the lignite-containing muds and clays are much higher than that of the macrofossil. The higher ratios in lignite-containing muds and clays are possibly attributed to enhanced microbial reduction of organic matter under reduced condition in the swampy environments. A large amount of angiosperm-derived triterpenoids detected in the conifer cone macrofossil are considered as contaminants in the sample from sedimentary organic particles originated from detrital waxes of angiosperms. Such contamination might occur by migration of organic compounds within sediment after deposition. The angiosperm-derived polar terpenoids may be hardly affected by contamination by migration of organic matter from the adjacent sediments because these are less abundant in the conifer macrofossil. Thus, it is suggested that the polar terpenoid biomarkers are more reliable as paleochemotaxonomic and paleovegetation indicators. [Copyright &y& Elsevier]

Abstract: The distributions of aliphatic and aromatic terpenoids in Cretaceous and Paleogene angiosperm fossils from Japan were investigated. Aliphatic A ring-degraded oleanane, ursane and lupane were found in all samples. In addition, aliphatic gymnosperm-derived diterpenoids were detected in significant quantities. Aromatic oleanane-type triterpenoids were the major components, with ursane- and lupane-type triterpenoids being minor compounds in all angiosperm fossils. In a Cretaceous gymnosperm fossil, major components included aliphatic labdane-, isopimarane- and abietane-type diterpenoids, aromatic abietane-type diterpenoids, and chrysene- and picene-type polyaromatic hydrocarbons (PAHs). Trace amounts of oleanane-, ursane- and lupane-type triterpenoids were also identified. It is likely that the aromatic triterpenoids were introduced to the gymnosperm fossil from the angiosperm-derived material in the sediments. We defined an angiosperm/gymnosperm index (al-AGI′) as an alternative to the aliphatic triterpenoid/diterpenoid ratio proposed in the literature. The al-AGI′ index may underestimate the angiosperm contribution, because the aliphatic angiosperm-derived triterpenoids are more readily converted to aromatic counterparts than the diterpenoids during diagenesis. An aromatic angiosperm/gymnosperm index (ar-AGI) can be calculated using aromatic diterpenoids and triterpenoids. We suggest that ar-AGI is best calculated using only the oleanane-, ursane- and lupane-type aromatic triterpenoids, and that the chrysene- and picene-type PAHs be excluded. [Copyright &y& Elsevier]

Abstract: One of bacteria collected from Lake Sagami, Japan, Brevibacillus sp., was found to have a lytic activity of cyanobacteria, but did not produce active compounds. Instead, the co-culturing of Microcystis with the Brevibacillus sp. enhanced the production of two volatile compounds, β-cyclocitral and 3-methyl-1-butanol, and the former had a characteristic lytic activity. It was confirmed that these volatile compounds were derived from the cyanobacteria themselves. β-Ionone, geosmin and 2-methylisoborneol derived from cyanobacteria and similar volatile compounds, terpenoids, produced by plants also had a lytic activity. The minimum inhibitory concentration values of the cyanobacterial metabolites were estimated to be higher than those of compounds from plants except for a few compounds. Among them, β-cyclocitral only produced a characteristic color change of culture broth from green to blue. This color change is similar to the phenomenon observed when a sudden decline in growth of cyanobacteria begins in a natural environment. [Copyright &y& Elsevier]

Abstract: The essential oils from a bogwood trunk of sugi (Cryptomeria japonica D. Don) from Sanbe-cho, Shimane, Japan, preserved for c. 3500–3800 years in volcanic ash (S-bogwood), were analyzed using gas chromatography-mass spectrometry (GC/MS). Eight sesquiterpenes and four diterpenes were identified. The main components were simonellite (19.2%), cis-calamenene (11.6%), and α-phyllocladane (8.8%). These results were compared with previous results for oils from a fresh stump of C. japonica, from Muikaichi-cho, Shimane, Japan (fresh wood) and for oils from a stump of another sugi bogwood preserved for c. 3000 years in sediment of a muddy field in Abu-cho, Yamaguchi, Japan (Y-bogwood). Simonellite, α-phyllocladane, selinane (4.3%), and eudalene (2.7%) were identified for the first time in bogwood trunk oil. Ash generated by oxidation of each of the two bogwood samples and fresh wood sample at 700°C was analyzed using scanning electron microscopy with energy dispersive X-ray analysis (SEM/EDXA). The major elements were S and Ca in S-bogwood ash, Fe and Ca in Y-bogwood ash, and K and Ca in the fresh wood ash, respectively. Sulfur in the S-bogwood ash is thought to have come from volcanic ash. The results suggest that S-bogwood was influenced directly by volcanic ash and the degree of terpenoid alteration was more drastic than that of Y-bogwood. [Copyright &y& Elsevier]

Studies nonmevalonate pathway by researchers from Japan. Presence of nonmevalonate pathway in higher plants and in many eubacteria; Description of a candidate compound for inhibiting MEP cytidylyltransferase; Significance of identifying a nonmevalonate pathway inhibitor on the development of new herbicides and drugs.

Oshimalides A ( 1 ) and B ( 2 ) were isolated from a Luffariella sp. marine sponge. The absolute configurations of the stereogenic centers in the cyclohexenone ring were determined by the modified Mosher's analysis of the reduction product. The absolute configuration of the stereogenic center in the dihydropyran ring was assigned by analysis of the 1 H NMR data of the vicinal diols which were prepared by AD-mix reagents stereoselectively.

The odor-active volatiles of Kinokuni mandarin (Citrus kinokuni Hort. ex Tanaka), an original mandarin orange in Japan, were characterized by a combination of instrumental and sensory analyses and compared with those of Satsuma mandarin (Citrus unshiu Marcovitch). An aroma extract dilution analysis (AEDA) of the polar fractions of Kinokuni and Satsuma mandarin peel oils identified five odorants in common as the most odor-active volatiles: (Z)-hex-3-enal, decanal, linalool, yuzuol, and (2E)-trans-4,5-epoxydec-2-enal. In addition, seven odorants were identified solely in Kinokuni mandarin as significant contributors: octanal, dodecanal, (2E,4E)-deca-2,4-dienal, geraniol, yuzunone, (2E,7Z)-trans-4,5-epoxydeca-2,7-dienal, and thymol. The odor-active volatiles in both the non-polar components of the peel oil and an extract of the juice prepared from Kinokuni mandarin were also identified. The (S)-isomer of linalool in Kinokuni mandarin peel oil was dominant in the enantiomeric distribution (92%), whereas the (R)-isomer was dominant in Satsuma mandarin peel oil (90%).