Search

A new homocysteine thiolactone derivative, thiolactomide (1), was isolated along with a known compound, N-acetyl homocysteine thiolactone (2), from a culture extract of soil-derived Streptomyces sp. RK88-1441. The structures of these compounds were elucidated by detailed NMR and MS spectroscopic analyses with literature study. Biological evaluation studies revealed that both 1 and 2 exhibit neuroprotective activity against 6-hydroxydopamine (6-OHDA) mediated neurotoxicity by blocking generation of hydrogen peroxide in neuroblastoma SH-SY5Y cells.

Three new trichostatin analogues, ulleunganilines A-C (1-3), and seven known trichostatins (4-10) were isolated from cultures of Streptomyces sp. 13F051. NMR, UV, and MS data indicated that the planar structures of 1-3 consisted of modified side chains in the trichostatic acid moiety. The absolute configuration of the 2,4-dimethyl-branched carbon chains in 1 and 2 was determined by the PGME method, while the amino acid group in 3 was identified by advanced Marfey's method. Based on the structure of the modified side chains, the origin of 1-3 is proposed. Further experiments indicated that 1 and 3 displayed moderate histone deacetylase inhibitory activity, suggesting that not only the hydroxamate group but also the N,N-dimethyl group were essential for the inhibitory activity.

A bioassay-guided investigation led to the isolation of three new carbazole glycosides, jejucarbazoles A–C (1–3), from Streptomyces sp. KCB15JA151. Their planar structures were elucidated by detailed NMR and MS spectroscopic analysis with a literature study. Their relative and absolute configurations were established by ROESY correlations, coupling constants, LC-MS analysis of thiocarbamoyl-thiazolidine carboxylate derivatives, and ECD calculation. Compounds 1–3 showed indoleamine 2,3-dioxygenase 1 (IDO1) inhibitory activity with IC50 values of 18.38, 9.17, and 8.81 μM. The molecular docking analysis suggested that all compounds act as heme-displacing inhibitors against IDO1 enzyme.

In this study, screening by LC-MS and cytotoxicity-guided isolation led to the identification of ulleungamide C (1), a previously unknown pipecolic acid-rich branched cyclic depsipeptide, from a soil actinobacterium Streptomyces sp. KCB13F003. The structure of 1 was determined by interpretation of spectroscopic and spectrometric data from 1D and 2D NMR and HRESIMS experiments. Antiproliferative assays using mammalian cancerous cells revealed that 1 inhibits the proliferation of HL-60 human promyelocytic leukemia cells. Cell cycle analysis showed an increased accumulation of cells in the G0/G1 phase after treatment with 1. Results of immunoblotting assays revealed that 1 reduced the expression levels of cyclin-dependent kinase 4 (CDK4), CDK6, retinoblastoma protein (Rb), and phosphorylated Rb, whereas it induced cyclin-dependent kinase inhibitor 1B (p27/Kip1) expression.

LC/MS-based chemical screening of culture extract led to a new highly oxygenated angucycline derivative, grecocycline D (1), from Streptomyces sp. KCB15JA014, isolated from a soil sample of Oedolgae in Jeju Island, Korea. The planar structure was determined on the basis of spectroscopic analysis, including 1D and 2D NMR techniques as well as HRESIMS and comparison with data from the literature. A relative and absolute configuration of 1 was assigned by ROESY experiment and electronic circular dichroism calculation. Compound 1 showed weak inhibitory activity against indoleamine 2,3-dioxygenase.

A LC-MS-guided screening led to the isolation of two new streptimidone derivatives (2 and 3) containing a glutarimide ring and two glutarimide ring-opened compounds (4 and 5) along with a known glutarimide-containing polyketide, streptimidone (1) from Streptomyces sp. W3002 strain. Their structures were elucidated by MS and NMR spectroscopic analyses and by comparison with data from the literature. Compound 2 is a non-hydroxylated analog at the C-5 position of streptimidone. The structure of 3 was determined as a streptimidone derivative possessing the α, β-unsaturated ketone moiety at positions C-5 and C-6. Compound 4 had similar chemical shifts and splitting patterns with 3, but the glutarimide ring is opened. Compound 5 closely resembles that of 4 with the only difference being the existence of an additional methoxy group instead of an amide group. Streptimidone (1) and 3 showed weak cytotoxic activity against three human cancer cell lines, respectively.

Indoleamine 2,3-dioxygenase 1 (IDO1), a tryptophan catabolising enzyme, is known as a tumour cell survival factor that causes immune escape in several types of cancer. Flavonoids of Sophora flavescens have a variety of biological benefits for humans; however, cancer immunotherapy effect has not been fully investigated. The flavonoids (1–6) isolated from S. flavescens showed IDO1 inhibitory activities (IC50 4.3–31.4 µM). The representative flavonoids (4–6) of S. flavescens were determined to be non-competitive inhibitors of IDO1 by kinetic analyses. Their binding affinity to IDO1 was confirmed using thermal stability and surface plasmon resonance (SPR) assays. The molecular docking analysis and mutagenesis assay revealed the structural details of the interactions between the flavonoids (1–6) and IDO1. These results suggest that the flavonoids (1–6) of S. flavescens, especially kushenol E (6), as IDO1 inhibitors might be useful in the development of immunotherapeutic agents against cancers.

New glycosylated 26-membered triene macrolides catenulisporolides, the first polyketide metabolites from Catenulispora species, were obtained by targeting slow-forming colonies on selection agar plates and applying long-term cultivation. Their structures, including the full stereochemistry, were defined by comprehensive spectroscopic and chemical methods and confirmed by bioinformatics analysis. Analysis of the genome sequence revealed the responsible biosynthetic gene cluster spanning ∼160 kbp, and feeding experiments with isotope-labeled precursors showed that isovaleric acid acts as a rare starter unit. Catenulisporolides exhibited antimalarial activities against resistant strains of Plasmodium falciparum, and enhanced activity was observed in semisynthetic derivatives.

Changes in the dimensions of lignocellulose nanofibrils (LCNFs) with different lignin contents from betung bamboo (Dendrocalamus asper) by enzymatic hydrolysis using endoglucanase (EG) were investigated. Lignin contents were adjusted from 3% to 27% by NaClO2/acetic acid treatment, and LCNFs were prepared using a wet disk-mill (WDM). The dimensions of the LCNFs significantly decreased with decreasing lignin content and increasing EG addition. With increasing EG content, the average diameter of the LCNFs significantly decreased, even though they contained parts of hemicellulose and lignin. The crystal structure showed the typical cellulose I structure in all samples, but the intensity of the diffraction peak slightly changed depending on the lignin and EG contents. The crystallinity index (CrI) values of the LCNFs increased a maximum of 23.8% (LCNF-L27) under increasing EG addition, regardless of the lignin content. With the EG addition of three times the LCNF amount, LCNF-L3 showed the highest CrI value (59.1%). By controlling the composition and structure of LCNFs, it is expected that the wide range of properties of these materials can extend the property range available for existing materials.

A chemical investigation of a culture extract from a soil-derived Streptomyces sp. RK88-1441 led to the isolation and characterization of two new glycosylated anthraquinones, aturanosides A (1) and B (2), and a new anthraquinone derivative, aturanocin (3). The structures of these compounds were elucidated by detailed NMR and MS spectroscopic analyses. The absolute configurations of the sugar units, based on the magnitudes of the coupling constants, ROESY correlations, and chemical derivatization, from 1 and 2 are 6- O-[ N-acetyl-α-d-glucosamino-(1→2)-α-l-rhamnoside] and 6- O-α-l-rhamnoside, respectively. Compounds 1 and 2 showed no cytotoxicity against human umbilical vein endothelial cells (HUVECs), but significantly suppressed vascular endothelial growth factor (VEGF)-induced tube formation and invasion of HUVECs. The down-regulation of both the phosphorylation of VEGF receptor 2 and the expression of vascular endothelial cadherin at the protein level were also observed.

In the course of studies to discover natural products with anti-angiogenic properties, two cyclic octapeptides, octaminomycins A (1) and B (2), were isolated from the cultures of Streptomyces sp. RK85-270. Octaminomycins suppressed the vascular endothelial growth factor (VEGF)-induced proliferation, adhesion, tube formation, migration, and invasion of HUVECs. Anti-angiogenic activity was futher confirmed in vivo by the chicken chorioallantoic membrane assay. We also identified that 1 and 2 inhibited the phosphorylation of VEGF receptor 2, AKT, and ERK1/2 and the expression and activities of MMP-2 and MMP-9. These results suggest that 1 and 2 may serve as potential scaffolds for the development of therapeutic agents to angiogenesis-dependent diseases.

Four new compounds, phomalichenones A-D (1-4), and seven known compounds (5-11) were isolated from the cultures of an endolichenic fungus Phoma sp. EL002650. Their structures were determined by the analysis of their spectroscopic data (NMR and MS). Compounds 1 and 6 inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. In addition, compound 1 diminished the protein expression levels of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), and decreased the mRNA expression levels of pro-inflammatory cytokines, such as tumor necrosis factor-α (TNF-α), interleukin(IL)-1β, and IL-6.

A new series comprising phenylacetyl-homoserine lactones (HSLs), caffeoyl-HSL and feruloyl-HSL, was biologically synthesized using an artificial de novo biosynthetic pathway. We developed an Escherichia coli system containing artificial biosynthetic pathways that yield phenylacetyl-HSLs from simple carbon sources. These artificial biosynthetic pathways contained the LuxI-type synthase gene (rpaI) in addition to caffeoyl-CoA and feruloyl-CoA biosynthetic genes, respectively. Finally, the yields for caffeoyl-HSL and feruloyl-HSL were 97.1 ± 10.3 and 65.2 ± 5.7 mg/l, respectively, by tyrosine-overproducing E. coli with a L-methionine feeding strategy. In a quorum sensing (QS) competition assay, feruloyl-HSL and p-coumaroyl-HSL antagonized the QS receptor TraR in Agrobacterium tumefaciens NT1, whereas caffeoyl-HSL did not.

Analysis of the genome sequence of Streptomyces sp. KCB13F003 showed the presence of a cryptic gene cluster encoding flavin-dependent halogenase and nonribosomal peptide synthetase. Pleiotropic approaches using multiple culture media followed by LC-MS-guided isolation and spectroscopic analysis enabled the identification of two new chlorinated cyclic hexapeptides, ulleungmycins A and B (1 and 2). Their structures, including absolute configurations, were determined by 1D and 2D NMR techniques, advanced Marfey's analysis, and GITC derivatization. The new peptides, featuring unusual amino acids 5-chloro-l-tryptophan and d-homoleucine, exhibited moderate antibacterial activities against Gram-positive pathogenic bacteria including methicillin-resistant and quinolone-resistant Staphylococcus aureus.

Two angucyclines, pseudonocardones D (1) and E (2), were isolated from Streptomyces sp. KCB15JA151. The planar structure was elucidated by comprehensive spectroscopic analysis. The absolute configuration of the sugar unit was determined based on the basis of coupling constants, ROESY, chemical derivatization and HPLC analysis. The biological activities of compounds 1 and 2 were examined by performing a computational target prediction, which led to tests of the antiestrogenic activity. The result suggested that compound 1 might be an ERα antagonist.

A bioassay-guided investigation in conjunction with chemical screening led to the isolation of three new glycosides, ulleungoside (1), 2-methylaminobenzoyl 6-deoxy-α-l-talopyranoside (2), and naphthomycinoside (3), along with three known secondary metabolites (5-7) from Streptomyces sp. KCB13F030. Their structures were elucidated by detailed NMR and MS spectroscopic analyses. Absolute configurational analysis of the sugar units based on the magnitudes of the coupling constants, NOESY correlations, chemical derivatization, and optical rotation measurements revealed that compounds 1-3 and 5 incorporate the rare deoxyhexose 6-deoxy-α-l-talopyranose. The absolute configuration of a polyketide extender unit of 3 was determined by applying the J-based configuration analysis and modified Mosher's method. Ulleungoside (1) and naphthomycin A (7) showed in vitro inhibitory effects against indoleamine 2,3-dioxygenase activity. Further bioevaluation revealed that compounds 1 and 7 had moderate antiproliferative activities against several cancer cell lines, and compounds 5 and 6, which are members of the piericidin family, induced autophagosome accumulation.

Heat treatment of wood is an attractive alternative environmentally-friendly treatment to add value of less valuable woods by improving color, dimensional stability, and natural durability. To improve the color properties of Korean white pine (Pinus koraiensis) and royal paulownia (Pauwlonia tomentosa), we treated the woods at 160°C, 180°C, 200°C, and 220°C for 2 hours. Color change after heat treatment was evaluated using the CIE-Lab color system and survey was conducted to determine the consumer preferences towards color of heat-treated wood. Lightness (L*) decreased with increasing temperature and the higher degree of change was obtained in royal paulownia. The red/green chromaticity (a*) in both wood decreased after heat treatment at 160°C, and constantly increased after heat treatment at 180°C to 220°C. Yellow/blue chromaticity (b*) in Korean white pine tended to increase after heat treatment at 160°C, then decreased gradually afterwards. In royal paulownia, b* values linearly increased with increasing temperature. Overall color change (ΔE*) increased with increasing temperature with higher degree obtained in royal paulownia. Samples with the clamps in both wood species showed lower degree of the change in L*, a*, b and ΔE*. The results of the consumer preferences test showed that the darker colors of heat-treated woods were more preferred by consumers compared to the lighter colors of untreated woods. Consequently, heat treatment could enhance the color properties of Korean white pine and royal paulownia woods for value added products.

The objective of this study was to evaluate the characteristics of charcoals from juvenile woods of albizia (Paraserianthes falcataria), gmelina (Gmelina arborea), mindi (Melia azedarach), and mangium (Acacia mangium). Carbonization was performed at 400, 600, and 800°C for 10 min with a heating rate of 6°C/min. The physical, bioenergetic, and chemical properties were evaluated. Maximum char yield was obtained at 400°C and the increase of carbonization temperature resulted in a decrease of char yield. At the same carbonization temperature, char yield was higher in wood with greater initial density, i.e. ordered from the highest to the lowest: mangium, mindi, gmelina, and albizia. The heating values in all woods increased after carbonization, with maximum values at 600°C. Maximum energy densification ratio and energy yield were obtained at carbonization temperature of 600°C and 400°C, respectively. Char yield of 23.62-39.03%, heating value of 25.16-33.85 kJ/g, energy densification ratio of 1.45-1.72, energy yield of 39.09-60.10%, ash content of 0.80-3.94%, volatile matter of 14.61-38.69%, and fixed carbon of 58.58-83.27% were obtained in all charcoals from juvenile woods and were comparable with those of mature woods, showing suitability for the production of charcoal fuel.

Paulownia tomentosa is one of fast-growing wood species in Korea. In order to evaluate the solid bioenergy properties of Paulownia tree, this study examined the heating value, moisture content (MC), pH and proximate analysis of stem, branch, root, bark and leaf. The heating values of wood parts were slightly higher than those of bark and leaf, and that of branch was the highest among all the samples. The higher moisture content of bark and leaf referred to their lower heating value. Also, the pH of stem, branch and root was similar and lower than those of bark and leaf. The ash content of bark and leaf was much higher than that of wood parts, which is the one of the reasons for effect on the lower heating value and higher pH. While, the volatile matter content (VMC) of bark and leaf was lower than those of wood parts. The bark showed the highest fixed carbon content (FCC), while the FCC of stem was the lowest among all the samples. The obtained results are encouraging that the Paulownia tree could be totally utilized as alternative fuels for bioenergy production.

Two new phenylspirodrimane derivatives, stachybotrysin (1) and stachybotrylactone B (2), were isolated from the cultures of the marine-derived fungus Stachybotrys sp. KCB13F013. The structures were determined by analyzing the spectroscopic data (1D and 2D NMR and MS) and chemical transformation, including the modified Mosher's method and single-crystal X-ray structure analysis. Compound 1 exhibited an inhibitory effect on osteoclast differentiation in bone marrow macrophage cells via suppressing the RANKL-induced activation of p-ERK, p-JNK, p-p38, c-Fos, and NFATc1.

Three cyclic lipopeptides, including one known (1) and two new (2 and 3) compounds, that possess the rare enamide linkage group were discovered from Streptomyces sp. KCB14A132, an actinobacterium isolated from a soil sample collected from Jeung Island, Korea. The NMR and MS-based characterization showed that they differed in the amino acid residues in the peptide backbone. Application of Marfey's analysis, GITC derivatization, and modified Mosher's method, as well as ECD measurements provided the absolute configurations of enamidonin (1) and those of new compounds enamidonins B and C (2 and 3). The two new enamidonin analogues were shown to exhibit antibacterial activity against Gram-positive bacteria including methicillin-resistant and quinolone-resistant Staphylococcus aureus. Furthermore, evaluation of the extraction conditions and a close inspection of the LC-MS chromatograms revealed that the N, N-acetonide unit of the enamidonin family was formed during the acetone extraction process. The chemically prepared deacetonide derivatives of enamidonins were found to lack antibacterial activity, demonstrating that the dimethylimidazolidinone residue is necessary for antibacterial activity.

The carbonization characteristics of tension wood (TW) and compression wood (CW) from Paulownia tomentosa and Pinus densiflora branch woods, respectively, were investigated and compared to those of opposite wood (OW) and lateral wood (LW). The carbonization was conducted at 400, 600, and 800 °C. Heating values, pH, char yields, cell wall structures, and combustion characteristics were different in TW and CW, whereas only little differences were found among reaction wood, OW, and LW. The heating values of TW charcoal were lower than those of CW charcoal at 400 and 600 °C, while the pH of TW charcoal was higher than that of CW at all carbonization temperatures. The char yields of CW were the highest among all the samples at all carbonization temperatures. Furthermore, the TW charcoal was more thermally stable than CW charcoal. SEM observations revealed significant differences in the cell wall structures of the woods before and after carbonization. The gelatinous layer in TW disappeared, and the helical cavities and intercellular spaces in CW persisted throughout the carbonization process. The cell wall structures of the wood samples became smooth and amorphous as the carbonization temperature increased.

This study investigated several anatomical characteristics of Paulownia tomentosa roots. The root wood was separated into three parts from stem base (top, middle, and base) at different positions below ground. Qualitative anatomical data suggested that the growth rings in earlywood and latewood were structurally different. Furthermore, the root wood vessels were found having 2 to 3 radial multiples and they were appeared in the form of clusters. In addition, some sheath cells and septate axial parenchyma were observed. Regarding the quantitative anatomical characteristics, vessel and ray numbers per , as well as ray width and height differed significantly among the top, middle, and base rood wood parts. However, there were no significant differences in vessel diameters, cell wall thickness, and width and length of wood fibers among those parts. The crystallinity of the root top part was slightly higher than that of the middle and base parts. Furthermore, the vessel numbers, ray numbers, and ray width and height in the near pith (NP) area were higher compared to those in the near bark (NB) area. However, the fiber width and fiber length at NP were lower than those at NB. Overall, this study demonstrated some significant differences in the anatomical characteristics of the top, middle, and base parts of root wood from Paulownia tomentosa.

Twelve metabolites, including five highly oxygenated azaphilones, geumsanols A-E, along with seven known analogues were isolated from Penicillium sp. KCB11A109, a fungus derived from a ginseng field. Their structures were assigned by spectroscopic means (NMR and MS), and stereochemistries were determined by extensive spectroscopic analyses ((1)H-(1)H coupling constants, NOESY, and HETLOC) and chemical derivatizations (modified Mosher's method and acetonide formation). The isolates were evaluated for their anticancer, antimicrobial, antimalarial activities, and phenotypic effects in zebrafish development. Of these compounds possessing no pyranoquinone core, only geumsanol E exhibited cytotoxic activities and toxic effects on zebrafish embryos, suggesting that a double bond at C-11 and C-12 is important for biological activity.

Autophagy plays a major role in cell survival and has therefore been exploited as an important strategy in cancer therapy. In this study, we evaluated the autophagy-regulatory effects of kushenol E (KE), a bi-prenylated flavonoid isolated from Sophora flavescens and found that KE increased LC3B-II levels while inducing the formation of autophagic vacuoles and immature autophagosomes in HeLa and HCT116 cells. Transmission electron microscopy images revealed that KE treatment generates immature autophagosomes. Furthermore, KE inhibited autophagosome maturation as demonstrated by blocking the degradation of EGFP puncta in HeLa cells stably expressing EGFP-mRFP-LC3B. It also reduced lysosomal activity and cathepsin maturation by disrupting lysosomal positioning, subsequently inducing apoptosis. Further, a combinatorial approach employing cellular thermal shift assays, revealed valosin-containing protein (VCP)/p97 as a potential target protein of KE; the knockdown and overexpression of VCP/p97 confirmed its involvement in regulating lysosomal positioning for autophagy maturation via direct interactions with KE. Thus, KE may possess autophagy-regulating properties mediated by binding to VCP/p97.

Two new macrolide metabolites of the hygrolidin family, catenulisporidins A and B (1 and 2), together with a known compound hygrolidin (3), were isolated from the culture broth of the rare actinobacterium Catenulispora sp. KCB13F192. Their structures were elucidated on the basis of HRESIMS spectrometric and NMR spectroscopic analyses. Catenulisporidins A and B are the first example of natural hygrolidin and bafilomycin derivatives featuring a modified macrolide ring, and catenulisporidin A possesses a tetrahydrofuran ring through an ether linkage between C-7 and C-10. In cell-based fluorescent imaging and immunoblot assays, the three compounds were shown to inhibit autophagic flux in HeLa cells.

The advances of genomic sequence analyses and genome mining tools have enabled the exploration of untapped microbial natural products. Through genome mining studies to discover cryptic natural products, we found biosynthetic genes encoding a new lasso peptide in the genome sequence of a soil bacterium, Streptomyces sp. KCB13F003 isolated from Ulleung Island (a small volcanic island), Korea. The production and purification of the encoded peptide, named ulleungdin, were achieved by optimizing the culture conditions followed by LC-MS-targeted isolation. Structure elucidation was performed by NMR spectroscopic and MS spectrometric analyses and chemical means (Marfey's and GITC derivatizations), proving ulleungdin to be a new 15-mer class II lasso peptide with a threaded structure. Biological evaluation with the cell invasion assay and time-lapse cell tracking analysis revealed that ulleungdin has significant inhibitory activities against cancer cell invasion and migration.

LC/MS-based chemical screening of fungal extract fraction library led to identification of three 2,3-aryl substituted furanone metabolites (1–3), including one known butenolide glycoside (1) whose stereochemistry remained unsolved and two new compounds gotjawaside and gotjawalide (2 and 3), from Auxarthron sp. KCB15F070, a fungus isolated from a soil sample of the volcanic island Jeju, Korea. Their planar structures were elucidated by 1D- and 2D-NMR spectroscopic and HRESIMS spectrometric techniques, and the absolute configurations of three compounds were solved using a combination of chemical derivatizations and computational analysis of vibrational circular dichroism (VCD) spectra.

Two new α-pyrones, dothideopyrones E (1) and F (2), were isolated from a culture of the endolichenic fungus Dothideomycetes sp. EL003334. Their structures were elucidated by spectroscopic data analysis. Their absolute configurations were established by the modified Mosher’s method. Compound 2 inhibited nitric oxide (NO) production with IC50 values of 15.0 ± 2.8 μM in lipopolysaccharide (LPS)-induced BV2 cells. Compound 2 diminished the protein expression levels of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Additionally, 2 decreased the mRNA expression levels of pro-inflammatory cytokines, such as tumor necrosis factor-α (TNF-α), interleukin (IL)-1β, and IL-6.

Two new cyclic peptides, pentaminomycins A (1) and B (2), were isolated from cultures of Streptomyces sp. RK88-1441. Based on the interpretation of the NMR, UV, IR, and MS data, the planar structures of 1 and 2 were elucidated as cyclic pentapeptides with a modified amino acid residue, N5-hydroxyarginine (N5-OH-Arg). The absolute configurations of the constituent amino acid residues were determined by the advanced Marfey’s method. Localization of l- and d-amino acids in the sequence was ascertained by chiral analysis of the fragment peptide obtained from a partial hydrolysate; amino acids were identified by LC-MS. Pentaminomycin A (1) reduced α-MSH-stimulated melanin synthesis by suppressing the expression of melanogenic enzymes including tyrosinase, tyrosinase-related protein-1 (TRP-1), and tyrosinase-related protein-2 (TRP-2).

This research focused on the natural durability of twenty one lesser known tropical wood species planted in West Java, Indonesia against subterranean termite (Coptotermes curvignathus). It was observed that both heartwood and sapwood of Kiara payung (Filicium decipiens); heartwoods of Nangka (Arthocarpus heterophyllus), Mahoni (Swietenia macrophylla) and Simpur (Dillenia grandifolia); and sapwood of Bungur (Lagerstroemia speciosa) were rated as resistant (natural durability class II) according to Indonesian standard SNI 01.7207.2006 (BSN 2006). Both heartwood and sapwood of Salam (Syzigium polyanthum), Pasang (Lithocarpus sundaicus), Bisbul (Diospyros discolor), Rukam (Flacourtia rukam) and Trembesi (Samanea saman); heartwood of Puspa (Schima walichii), Bungur, Tanjung (Mimusops elangi) and Angsana (Pterocarpus indicus) were rated as moderately resistant (natural durability class III). Both heartwood and sapwood of Sungkai (Peronema canescens), Pine (Pinus merkusii), Mangium (Acacia mangium) and Afrika (Maesopsis eminii); sapwoods of Mahoni, Puspa and Tanjung were rated as poorly resistant (natural durability class IV). Both heartwood and sapwood of Agathis (Agathis dammara), Durian (Durio zibethinus), Ki sampang (Evodia latifolia) and Jabon (Anthocephalus cadamba); sapwoods of Nangka and Angsana were rated as very poorly resistant (natural durability class V). This reserach showed that woods with lower resistance against C. curvignathus attack (natural durability class IV and V) tend to have lower termite mortality values compared to woods with higher resistance against C. curvignathus attack (natural durability class II and III). Results of the study will provide some valuable information on termite resistance of twenty one lesser known tropical wood species planted in Indonesia.

1. Subject and sourceThe Rhododendron genus containing over 850 species is one of the largest genera in the family Ericaceae. The genus ismostly distributed in Asia and sparsely populated in North America and Europe (Popescu and Kopp, 2013). Rhododendronbrachycarpum G. Don is an evergreen indeciduous broad-leaved shrub and utilized for alleviation of diabetes, hypertensionand rheumatoid arthritis (Jang et al., 2005). Radical climate changes have played a central role in reducing the population,leading its designation as an endangered and rare species (Lee et al., 2002; Lee and Shim, 2011). In our continuing efforts todiscoverpotentialvalue of theKoreanendangeredspecies, weherein describe theisolation and structuralcharacterization ofa new kaurane-type diterpenoid glycoside

Two new cyclic octadepsipeptides, octaminomycins A (1) and B (2), were isolated from a microbial metabolite fraction library of Streptomyces sp. RK85-270 based on Natural Products Plot screening. Their structures were elucidated on the basis of HRESIMS, 1D and 2D NMR spectroscopic data, and MS/MS experiments for sequence analysis. The absolute configurations of the constituent amino acid residues were determined by a combination of single-crystal X-ray diffraction and Marfey’s methodology. Notably, octaminomycins A (1) and B (2) showed good in vitro antiplasmodial activity against chloroquine-sensitive as well as chloroquine-resistant strains with no cytotoxicity up to 30 μM.

The physical and mechanical characteristics of 10 Indonesian wood species were investigated. Mangium, Gandaria and Rambutan showed higher density. Mangium, Gandaria and Mangga appeared lower in shrinkage, and the ratio of tangential/radial was low in Albizia, Kupa and Mangga. The compression strength parallel to the grain and hardness

During the course of screens to identify anti-melanogenic agents from natural resources, we found that the methanol extract of the dried flower of Inula britannica L. inhibited melanin synthesis in cultured melanoma cells stimulated with 3-isobutyl-1-methylxanthine (IBMX). A bioassay-guided isolation of the chloroform fraction of the I. britannica using an in vitro melanogenesis inhibition assay led to the isolation of sesquiterpenes, 1-O-acetylbritannilactone (1), britannilactone (2) and neobritannilactone B (3). Compounds 1 and 2 significantly reduced melanin production in a dose-dependent manner with IC50 values of 13.3 and 15.5 μM, respectively, whereas compound 3 was found to be cytotoxic. Compound 1 also inhibited the tyrosinase activity only in cell based-systems. Western blot analysis indicated that compound 1 inhibited melanogenesis by activating extracellular signal-regulated kinase (ERK) and Akt signaling and also inhibiting cAMP related binding protein, which regulates its downstream pathway, including tyrosinase, tyrosinase related protein-1 and TRP-2. These results demonstrated that compound 1, a major sesquiterpene from the flowers of I. britannica, exhibited anti-melanogenic activity by suppression of tyrosinase expression via ERK and Akt signaling. Taken together, our results suggest that these compounds may act as potent natural skin-lightening agents.

In the course of studies on bioactive metabolites from marine fungi, a new 10-membered lactone, named penicillinolide A (1) was isolated from the organic extract of Penicillium sp. SF-5292 as a potential anti-inflammatory compound. The structure of penicillinolide A (1) was mainly determined by analysis of NMR and MS data and Mosher's method. Penicillinolide A (1) inhibited the production of NO and PGE(2) due to inhibition of the expression of iNOS and COX-2. Penicillinolide A (1) also reduced TNF-alpha, IL-1 beta and IL-6 production, and these anti-inflammatory effects were shown to be correlated with the suppression of the phosphorylation and degradation of I kappa B-alpha, NF-kappa B nuclear translocation, and NF-kappa B DNA binding activity. In addition, using inhibitor tin protoporphyrin (SnPP), a competitive inhibitor of HO activity, it was verified that the inhibitory effects of compound 1 on the production of pro-inflammatory mediators and NF-kappa B DNA binding activity were partially associated with HO-1 expression through Nrf2 nuclear translocation.

Three new oxindole derivatives, RK-270A (1), B (2) and C (3) (Figure 1), were discovered and isolated from Streptomyces sp. RK85-270. They had an isopropylidene group at C-3 position of an oxindole skeleton, and C-1 also had a prenyl group and belonged to a class of 6-prenylated indoles. The isolation of this type of indoles was the first example as a natural product. Their cytotoxicity and antibacterial activities were evaluated.

Geldanamycin (GM) and its analogs are important anticancer agents that inhibit heat shock protein (Hsp) 90, which is a major chaperone protein in cancer cells. Accordingly, based on interest in obtaining novel natural GM derivatives, the potential of Streptomyces hygroscopicus JCM4427, a GM producer, was explored for novel natural GM derivative(s), resulting in the discovery of new GM analogs as a biosynthetic shunt product and intermediates from its fermentation broth. In this study, the fermentation, isolation, structure determination, and biological activity of the compounds, two new tetracyclic thiazinogeldanamycin (1) and 19-hydroxy-4,5-dihydrogeldanamycin (3), together with the three known 4,5-dihydrothiazinogeldanamycin (2), reblastatin (4), and 17-demethoxy-reblastatin (5), are described.

Geldanamycin (GM) is a naturally occurring anticancer agent isolated from several strains of Streptomyces hygroscopicus . However, its potential clinical utility is compromised by its severe toxicity and poor water solubility. For this reason, considerable efforts are under way to make new derivatives that have both good clinical efficacy and high water solubility. On the other hand, glycosylation is often a step that improves the water solubility and/or biological activity in many natural products of biosynthesis. Here, we report the facile production of glucose-conjugated nonbenzoquinone GM analogs using the Bacillus UDP-glycosyltransferase BL-C. Five aglycon substrates containing nonbenzoquinone aromatic rings were chosen to validate the in vitro glycosylation reaction. Putative glucoside compounds were determined through the presence of a product peak(s) and were also verified using LC/MS analyses. Further, the chemical structures of new glucoside compounds 6 and 7 were elucidated using spectroscopy data. These glucoside compounds showed a dramatic improvement in water solubility compared with that of the original aglycon, nonbenzoquinone GM.

Haenamindole (I) possesses benzyl-hydroxypiperazindione and phenyl-pyrimidoindole ring systems in the molecule and shows no cytotoxic activities against Hep-3B, HeLa, K562, and HL60 cell lines and no antimicrobial activities against Escherichia coli, Bacillus cereus, Staphylococcus aureus, and Salmonella enteritidis.

Two new botcinin derivatives encountered in the studies of secondary metabolites from the marine-derived fungus Botryotinia sp. SF-5275

We exploited the biological activity of an antibiotic agent asperlin isolated from Aspergillus nidulans against human cervical carcinoma cells. We found that asperlin dramatically increased reactive oxygen species (ROS) generation accompanied by a significant reduction in cell proliferation. Cleavage of caspase-3 and PARP and reduction of Bcl-2 could also be detected after asperlin treatment to the cells. An anti-oxidant N-acetyl-l-cysteine (NAC), however, blocked all the apoptotic effects of asperlin. The involvement of oxidative stress in asperlin induced apoptosis could be supported by the findings that ROS- and DNA damage-associated G2/M phase arrest and ATM phosphorylation were increased by asperlin. In addition, expression and phosphorylation of cell cycle proteins as well as G2/M phase arrest in response to asperlin were significantly blocked by NAC or an ATM inhibitor KU-55933 pretreatment. Collectively, our study proved for the first time that asperlin could be developed as a potential anti-cancer therapeutics through ROS generation in HeLa cells.

Two new oxepin-containing (1 and 2) and two diketopiperazine-type alkaloids (3 and 4) have been isolated from an EtOAc extract of the marine-derived fungus Aspergillus sp. SF-5044. The structures of these metabolites were determined through analysis of NMR and MS data, along with Marfey's method. Compound 1 showed weak growth inhibitory activity against a small panel of cell lines.

In this study, the figure of domestic hardwood was observed using the naked eye and the possibility of substituting imported wood with domestic one in the making woodcraft or furniture was investigated. It was known from the investigation on 8 different hardwoods that there were various figures such as cloud-shaped figure, blister figure, crotch figure, bird`s eye figure, etc. in Zelkova serrata wood and the beautiful pigment figure in Diospyros Kaki wood. There were the unusual figures such as wavy grain figure, fiddle back figure, etc. in Cedrela sinensis wood and was clear ray-fleck figure in Quercus variabilis wood. There were also various figures such as wavy grain figure, blister figure, pigment figure, etc. in Sophra japonica, Tilia amurensis, Castanea crenata, Kalopanax septemlobus wood, etc. It is thus that distinguished figures appeared in each kind of wood can be used for craft, sculpture, furniture, and interior material. These kinds of figures can also be used for instrument, toy, stationery, life article material and souvenir, etc. And it can be expected that they will replace the imported wood has been mainly used to make the woodcraft or furniture until now.

Microbial studies of soil samples collected at Ochang, Korea led to the isolation of the actinobacterium Streptomyces sp. KCB16C001. Subsequent LC/MS analysis of the culture extract for dereplication purposes enabled the identification of a new metabolite ochangoside (1), whose chemical structure was determined to be 1-( α -L-rhamnosyl)-lumichrome by scale-up purification and structure elucidation procedures based mainly on NMR and MS spectroscopic data. Determination of the stereochemistry of the sugar moiety was achieved by LC/MS analysis of the sugar derivatized with L-cysteine methyl ester and o -tolyl isothiocyanate. Our results represent a rare example of natural lumichrome glycoside with a sugar unit attached at N −1.

Two heterotrophic, agarolytic bacteria were isolated from marine environments. A 16S rRNA gene sequence analysis showed the isolates (designated strains J42-3A(T) and 04OZ-AS15-7A) to be positioned in a separate lineage within the genus Psychromonas. Members of the genus Psychromonas are recognized as being psychrophilic or psychrotolerant, whereas none of the currently established Psychromonas species is known to be agarolytic. The DNA G+C contents of the isolates were about 42 mol% and the predominant cellular fatty acids were 16 : 1omega7c and 16 : 0. Based on the results of the phylogenetic and phenotypic analyses and DNA-DNA hybridization data, the isolates represent a novel species, for which the name Psychromonas agarivorans sp. nov. is proposed. The type strain is J42-3A(T) (=NBRC 104585(T)=KCTC 22285(T)).

Two novel cyclic depsipeptides, ulleungamides A (1) and B (2), were isolated from cultures of terrestrial Streptomyces sp. Their structures were determined by analyses of spectroscopic data and various chemical transformations, including modified Mosher's method, advanced Marfey's method, PGME, GITC derivatizations, and Snatzke's method. Ulleungamides were determined to be a new class of peptides bearing unprecedented units, such as 5-hydroxy-6-methyl-2,3-dehydropipecolic acid, 4,5-dihydroxy-6-methyl-2,3-dehydropipecolic acid, and amino-linked 2-isopropylsuccinic acid. Ulleungamide A displayed growth inhibitory activity against Staphylococcus aureus and Salmonella typhimurium without cytotoxicity.

During the chemical investigation of marine-derived fungus, an unusual diketopiperazine (DKP) alkaloid, haenamindole (1), was isolated from a culture of the marine-derived fungus Penicillium sp. KCB12F005. The structure of 1, which possesses benzyl-hydroxypiperazindione and phenyl-pyrimidoindole rings system in the molecule, was elucidated by analysis of NMR and MS data. The stereochemistry of 1 was determined by ROESY and advanced Marfey's method.

The objective of this research was to evaluate the effect of bamboo species and resin content on the physical and mechanical properties of oriented strand boards (OSBs) prepared from steam-treated bamboo strands. The strands from three species of Indonesian bamboo, namely Andong (Gigantochloa verticillata), Betung (Dendrocalamus asper), and Ampel (Bambusa vulgaris), were steamed at 126 °C for 1 h at a pressure of 0.14 MPa. Three-layered OSBs with the core layer oriented perpendicularly to the face layers were prepared by bonding them together with 3 to 5% methylene diphenyldiisocyanate (MDI) resin based on oven-dried strands and with the addition of 1% paraffin. The strand compositions for the face, core, and back layers were 25%, 50%, and 25%, respectively. The slenderness ratios and aspect ratios of the strands ranged from 71.02 to 76.60 and from 2.96 to 3.02, respectively. The physical and mechanical properties of the OSBs fabricated from Andong and Betung were better than those from Ampel, and the properties of all OSBs were improved by increasing their resin content. OSBs from Betung with 3 to 5% resin content and those from Andong and Ampel with 4 to 5% resin content showed strength retention of more than 50%, which means they can be used for exterior structural applications. Except for OSBs fabricated from Ampel with 3% resin content, the properties of all OSBs prepared in this study were higher than the minimum values required by the CSA O437.0 (grade O-1) standard (2011).