Synthesis,spectral characterization,and in vitro antibacterial and antifungal activities of novel 1,3-thiazine-2-amines comprising morpholine nucleus

A collection of 4-(4-morpholinophenyl)-6-aryl-6H-1,3-thiazin-2-amines (20–28) were synthesized and their in vitro antimicrobial activity was investigated. Compound 21 against P. aeruginosa, 23 against B. subtilis, 24 against V. cholerae and P. aeruginosa, 26 against S. aureus and B. subtilis, 27 against B. subtilis and E. coli, and 28 against all tested bacterial strains exerted excellent antibacterial activity. Compound 20 against A. flavus and Rhizopus, 21, 26 against Rhizopus, 22, 27 against Mucor, 23 against A. flavus, 24 against both A. flavus and Mucor, 25 against all tested strains, and 28 against Rhizopus and M. gypseum exerted excellent antifungal activity.     

Miscellaneous mistletoe notes, 48–60: Descriptions of twelve new species of Loranthaceae and Viscaceae

Twelve new South American species of Loranthaceae (Aetanthus, Cladocolea, Oryctanthus, and Struthanthus) and Viscaceae (Dendrophthora and Phoradendron) are described and illustrated: Aetanthus trifolius, Cladocolea rostrifolia, Dendrophthora lanceolata, Dendrophthora rotundata, Dendrophthora tenuis, Dendrophthora werffii, Oryctanthus minor, Phoradendron pascoi, Phoradendron vasquezianum, Struthanthus apiculatus, Struthanthus schultesii, and Struthanthus sessiliflorus. Additionally, Cladocolea alternifolia, previously thought to be probably extinct, is reported to occur on Ilha Grande, just west of Rio de Janeiro, Brazil.     

A revision of the genus Paronthobium from New Caledonia (Coleoptera: Scarabaeidae: Scarabaeinae: Epilissini)

A revision of the New Caledonian genus Paronthobium Paulian 1984 is presented. Anonthobium Paulian 1984 is synonymized with Paronthobium Paulian 1984 after evaluating the diagnostic characters originally introduced by Paulian to separate them. Upon examination of the type specimens, Onthobium caledonicum Paulian 1935 is separated from O. simplex Fauvel 1903 and restored as valid. Anonthobium moui Paulian 1984 is synonymized with Anonthobium micros Paulian 1984. Fifteen new species are described: P. adio n. sp., P. daghfousi n. sp., P. dierkensi n. sp., P. farino n. sp., P. iac n. sp., P. julieni n. sp., P. memaoya n. sp., P. minutum n. sp., P. nasutum n. sp., P. orientale n. sp., P. peckorum n. sp., P. petchecara n. sp., P. subdentatum n. sp., P. taom n. sp. and P. tchingou n. sp. The genus Paronthobium is now composed of 22 species. Illustrations of parameres and of male protibiae are provided for each species. Distribution maps and a key to species are given.     

Synthesis of Annonaceous Acetogenins from Muricatacin

Synthetic studies of annonaceous acetogenins starting from (?)-muricatacin (1a) or (+)-muricatacin are described, involving (?)-muricatacin (1a), mono-THF acetogenin, solamin (2), reticulatacin (3), (15R, 16R, 19S, 20S)-cis-solamin (4a) and (15S, 16S, 19R, 20R)-cis-solamin (4b), non-adjacent bis-THF acetogenin, 4-deoxygigantecin (5), and epoxide-bearing acetogenin, (15S, 16R, 19S, 20R)-diepomuricanin (6a).     

Highly selective biotransformation of (+)-(1S)- and (−)-(1R)-camphorquinone by Aspergillus wentii

Abstract

To clarify the structures of biotransformation products and metabolic pathways, the biotransformation of monoterpenoids, (+)- and (?)-camphorquinone (1a and b), has been investigated using Aspergillus wentii as a biocatalyst. Compound 1a was converted to (?)-(2S)-exo-hydroxycamphor (2a), (?)-(2S)-endo-hydroxycamphor (3a), (?)-(3S)-exo-hydroxycamphor (4a), (?)-(3S)-endo-hydroxycamphor (5a), and (+)-camphoric acid (6a). Compound 1b was converted to (+)-(2R)-exo-hydroxycamphor (2b), (+)-(2R)-endo-hydroxycamphor (3b), (+)-(3R)-exo-hydroxycamphor (4b), (+)-(3R)-endo-hydroxycamphor (5b), and (?)-camphoric acid (6b). Compound 1a mainly produced 2a (65.0%) with stereoselectivity, whereas 1b afforded 3b (84.3%) with high stereoselectivity. These structures were confirmed by gas chromatography–mass spectrometry, infrared, ¹H nuclear magnetic resonance (NMR), and ¹³C NMR spectral data. The products illustrate the marked ability of A. wentii for enzymatic oxidation and ketone reduction.     

Nomenclatural changes in <Emphasis Type="Italic">Lithospermum</Emphasis> (Boraginaceae) and related taxa following a reassessment of phylogenetic relationships

Lithospermum (Boraginaceae) comprises approximately 40 species in both the Old and New Worlds, with a center of diversity in the southwestern United States and Mexico. Using ten cpDNA regions, a phylogeny of Lithospermum and related taxa was reconstructed. Lithospermum (including New World and Old World species) and related New World members of Lithospermeae form a monophyletic group, with Macromeria, Onosmodium, Nomosa, Lasiarrhenum, and Psilolaemus nested among species of Lithospermum. New World Lithospermeae also is a monophyletic group, with Eurasian species of Lithospermum sister to this group. Because Lithospermum is not monophyletic without the inclusion of the other New World genera, species from these genera are transferred to Lithospermum, and appropriate nomenclatural changes are made. New combinations are Lithospermum album, Lithospermum barbigerum, Lithospermum dodrantale, Lithospermum exsertum, Lithospermum helleri, Lithospemum leonotis, Lithospermum notatum, Lithospermum oaxacanum, Lithospermum pinetorum, Lithospermum rosei, Lithospermum trinverium, and Lithospermum unicum; new names are Lithospermum chiapense, Lithospermum johnstonii, Lithospermum macromeria, Lithospermum onosmodium, Lithospermum rzedowskii, and Lithospermum turneri.     

Sorption of Cadmium and Lead by Bacteria–Ferrihydrite Composites

The sorptive behavior of bacteria—iron oxide composites was investigated in batch metal sorption assays using ferrihydrite in isolation (0.13 and 0.14 g/L ferrihydrite in cadmium and lead systems, respectively) as well as in combination with Bacillus subtilis (0.25 g/L adsorbent mixture) and Escherichia coli (0.27 g/L adsorbent mixture). A pH range from 3.0 to 6.5 was studied using total metal concentrations of 1.0 × 10 ^{? 4.0} and 3.2 × 10 ^{? 5} M with adsorbent mixtures proportioned on a 1:1 mass/volume basis. The log of the apparent surface complex formation constants (log K ^S _M ) and sorption capacity (S _max ) values were determined by fitting the experimental data to one-site Langmuir sorption isotherms. The one-site model effectively described the sorption data (r ² > 0.9), where Cd ^{2 +} exhibited somewhat lower sorption affinities (log K ^S _M = ?3 for ferrihydrite, ?1.7 for B. subtilis–ferrihydrite, and ?1.1 for E. coli–ferrihydrite) than Pb ^{2 +} (log K ^S _M = ?0.9 for ferrihydrite, ? 0.2 forB. subtilis–ferrihydrite, and –0.1 for E. coli–ferrihydrite). The corresponding S _max values for Cd ^{2 +} and Pb ^{2 +} on ferrihydrite were 0.78 mmole/g and 1.34 mmole/g, respectively. For the B. subtilis–ferrihydrite composites, Cd ^{2 +} and Pb ^{2 +} S _max values were lower at 0.29 mmole/g and 0.5 mmole/g, respectively. Similar values were determined for the E. coli–ferrihydrite composites (0.15 mmole/g and 0.68 mmole/g for Cd ^{2 +} and Pb ^{2 +} , respectively). The sorption of Cd ^{2 +} and Pb ^{2 +} by each of the sorbent systems exhibited a strong dependence on pH with sorption edges in the range of pH 4.0 to 7.3. The observed S _max of the composites were lower than values predicted upon available site additivity (Cd ^{2 +} _{B. subtilis ?ferrihydrite} : 0.29 mmole/g (observed) < 0.57 mmole/g (calculated); Cd ^{2 +} _{E. coli ?ferrihydrite} : 0.15 mmole/g (observed) < 0.44 mmole/ g (calculated); Pb ^{2 +} _{B. subtilis ?ferrihydrite} : 0.5 mmole/g (observed) < 0.805 mmole/g (calculated); Pb ^{2 +} _{E. coli –ferrihydrite} : 0.68 mmole/g (observed) < 0.775 mmole/g (calculated)), implying that a masking of reactive surface sites by attachment had occurred between the bacteria and ferrihydrite. Electrophoretic mobility analysis indicated that the ferrihydrite surface properties dominate the net surface charge for each composite system with lesser contributions from the bacteria.     

Comparison of Soybean Tissue Extracted with Different Solvents

The enantioselective hydrolysis of (R,S)-3-acetoxymethyl-7,8-difluoro-2,3-dihydro-4H-[1,4]benzoxazine (I) with enzymes was investigated. Optically active I and its hydrolyzate, 7,8-difluoro-2,3-dihydro-3-hydroxymethyl-4H-[1,4]benzoxazine (II), are the intermediates for preparing optically active ofloxacins, whose racemate is known to be an excellent antibacterial agent. Lipoprotein lipase from Pseudomonas fluorescens (LPL Amano 3) was found to predominantly hydrolyze (S)-I, giving (R)-I in 54% e.e. and (R)-II in 44% e.e. On the other hand, lipase from Candida cylindracea was found to predominantly hydrolyze (R)-I, giving (S)-I in 24% e.e. and (S)-II in 20% e.e. Since, the optical purities of I and II thus obtained were not particularly high, these optically active I and II were converted into 3-acetoxymethyl-7,8-difluoro-2,3-dihydro-4-(3,5-dinitrobenzoyl)-4H-[1,4]benzoxazine (IV). After recrystallizing IV from ethyl acetate-hexane, (S)- and (R)-II were obtained with high enantiomeric excess by removing the crystallized racemic IV and subsequently hydrolyzing the resulting optically active IV with alkali. The reduction of II afforded 7,8-difluoro-2,3-dihydro-3-methyl-4H-[1,4]benzoxazine (III), for which the optical purity was estimated to be >96%e.e. by HPLC analysis. (R)- and (S)-ofloxacin were prepared from (R)- and (S)-III with retention of their configuration.     

Revision of the genus Adorodocia Brenske 1893 (Coleoptera: Scarabaeoidea: Rutelinae: Adoretini) endemic to Madagascar

Summary. The Adoretini of the Malagasy endemic genus Adorodocia Brenske 1893 is revised. Fourteen new species and one new subspecies are described and compared with their most closely related species: A. constricta n. sp., A. cuccodoroi n. sp., A. flava n. sp., A. liliae n. sp., A. marginata n. sp., A. peyrierasi n. sp., A. pseudoconstricta n. sp., A. pseudoflava n. sp., A. pseudostrigata n. sp., A. recta n. sp., A. robusta n. sp., A. sogai n. sp., A. vadoni n. sp., A. viettei n. sp. and A. vittaticollis flavipes n. ssp. The synonymy between Adoretus strigatus Waterhouse 1878, and Pseudadorodocia aenigma Arrow 1901, is confirmed. Thus, based on the results of this study, the genus Adorodocia includes 16 species, and one of them is represented by two subspecies. Diagnostic characters to separate the species in the genus deal mostly with the shape of parameres, color of body and legs, shape of pronotum and female eighth tergite, setation of pronotum and elytra. Key to species, diagnoses and distribution for each species are provided. Endophallus and female genitalia are illustrated for the first time for this genus.     

New and little known species of the genus Zorochros Thomson 1859 (Coleoptera: Elateridae) from Palaearctic and Oriental Region

Sixteen new species of the genus Zorochros Thomson 1859 from China, Indonesia, Malaysia, Nepal and Thailand are described and illustrated, a key to the species of the Zorochros indicus group is given, and new records on already known species are provided. New species: Z. ahrensi n. sp., Z bingkorensis n. sp., Z. dabieshanensis n. sp., Z. dolini n. sp., Z. hartmanni n. sp., Z. hubeiensis n. sp., Z. karnaliensis n. sp., Z. magnificus n. sp., Z. naniensis n. sp., Z. nigredos n. sp., Z. platiai n. sp., Z schawalleri n. sp., Z. schmidti n. sp., Z. senaroensis n. sp., Z. theodori n. sp., and Z. tongshanensis n. sp.     

Anomala trapezifera species-group: a burst of diversity (Coleoptera: Scarabaeidae: Rutelinae)

The species Anomala aereiventris n. sp., A. aspersa n. sp., A. atrivillosa n. sp., A. clarivillosa n. sp., A. contusa n. sp., A. eusticta n. sp., A. hiata n. sp., A. latifalculata n. sp., A. leopardina n. sp., A. levicollis n. sp., A. longisacculata n. sp., A. m-fuscum n. sp., A. perspicax n. sp., A. piccolina n. sp., A. globulata n. sp., A. stillaticia n. sp., A. subridens n. sp., A. subusta n. sp., A. tenoriensis n. sp., A. tuberculata n. sp. and A. vallisneria n. sp. from Costa Rica are described. These species and A. polygona Bates 1888, A. trapezifera Bates 1888 and A. vulcanicola Ohaus 1897 are placed in a new species-group, named after A. trapezifera, whose diagnosis is provided. Their distribution patterns are discussed.     

Preparation of Optically Pure cis-2,4-Dimethyl-l-cyclohexanones,the Key Intermediates in Cycloheximide Synthesis,Using Microbial Resolution

Asymmetric hydrolysis of acetate (10) of (±)-t-2,t-4-dimethyl-r-l-cyclohexanol with Bacillus subtilis var. niger gave (?)-(lS,2S,4S)-2,4-dimethyl-l-cyclohexanol (6a) and (+)-(1R,2R,4R)-acetate (10b) with high optical purities. Optically pure (?) and (+)-alcohols (6a and 6b) were prepared via corresponding 3,5-dinitrobenzoates. Oxidation of alcohols (6a and 6b) with chromic acid gave optically pure (?)-(2S,4S) and (+)-(2R,4R)-2,4-dimethyl-l-cyclohexanones (2a and 2b), respectively.     

武夷菌素高产基因工程菌株Streptomyces albulus OoWysR活性成分的分离鉴定

【背景】武夷菌素高产基因工程菌株Streptomyce albulus OoWysR具有明显的抑菌效果。【目的】明确S.albulus OoWysR的活性成分。【方法】采用柱层析法,利用大孔吸附树脂、离子交换树脂和高效液相色谱等对S.albulus OoWysR的活性成分进行分离纯化,经高分辨率电喷雾电离质谱(high-resolution electrospray ionization mass spectrometry,HR-ESI-MS)和核磁共振(nuclear magnetic resonance,NMR)等波谱技术对化合物化学结构进行鉴定,并通过生长速率法测定化合物的生物活性。【结果】从S.albulus OoWysR中分离鉴定出4个化合物,分别为对羟基苯甲酸(1)、吡咯-2-羧酸(2)、对羟基苯乙醇(3)和云南霉素(4)。化合物1对玉米弯孢病菌、番茄叶霉病菌、玉米小斑病菌和烟草赤星病菌具有一定的抑制作用;化合物2对番茄灰霉病菌、大豆菌核病菌、苹果腐烂病菌、玉米小斑病菌、小麦赤霉病菌、稻瘟病菌和烟草赤星病菌具有一定的抑制作用;化合物3对番茄灰霉病菌、苹果轮纹病菌、玉米小斑病...     

Synthesis and Antimicrobial Activity of Optically Active trans-Cycloheximide Isomers

Optically active tiraras-cycloheximide isomers such as cycloheximide [(2S,4S,6R,αR)-form (1)], naramycin B[(25,4S,6RαR)-form(4)], and new stereoisomers (2S,4S,6S,αS)-form (8) and (2S,4S,6R,αS)-from (9) were synthesized by an aldol condensation of trans-2,4-dimethyl-l-cyclohexanone (5b), with 4-(2-oxoethyl)-2,6-piperidinedione(6). The antimicrobial activity of trans- cycloheximide isomers (1, 4, 8, and 9) was examined against S. cerevisiae and P. oryzae. The stereoisomers 1 and 4 exhibited marked antimicrobial activity against both microorganisms as compared with their C- α-epimers 8 and 9.     

Description of nine new species of Heliura Butler from South America (Lepidoptera,Erebidae, Arctiinae,Arctiini, Ctenuchina)

Nine new species of the genus Heliura are described from Brazil (H. brasiliana sp. nov., H. olivocolora sp. nov., H. pulcherrima sp. nov., and H. laerteae sp. nov.), Ecuador (H. ecuadoris sp. nov.), Peru (H. flavipennis sp. nov. and H. peruana sp. nov.), and Venezuela (Heliura albiventris sp. nov. and H. juliani sp. nov.). They are illustrated in habitus and genitalia, and their phylogenetic affinities are discussed based on morphological evidence.     

铁皮石斛内生真菌次生代谢产物研究

为了解铁皮石斛(Dendrobium officinale)内生真菌Phyllosticta aristolochiicola的次生代谢产物,从该真菌中分离得到15个化合物,经波谱分析分别鉴定为N-methyl-2-pyrolidinone (1)、环-(甘氨酸-L-脯氨酸)(2)、环-(D-丙氨酸-L-脯氨酸)(3)、环-(L-缬氨酸-L-脯氨酸)(4)、环-(L-亮氨酸-L-脯氨酸)(5)、cyclo-(L-Leu-D-4-hydroxyprolinyl)(6)、环-(L-苯丙氨酸-L-脯氨酸)(7)、环-(L-苯丙氨酸-L-4-羟基脯氨酸)(8)、环-(L-酪氨酸-L-脯氨酸)(9)、环-(L-苯丙氨酸-L-亮氨酸)(10)、啤酒甾醇(11)、对羟基苯乙醇(12)、对羟基苯乙酸(13)、(2S,3R)-1-(4-羟基苯基)丁烷-2,3-二醇(14)和(2R,3S)-1-苯基丁烷-2,3-二醇(15)。采用MTS法检测抗肿瘤活性表明,化合物2、10和14对HL-60、A-549、SMMC-7721、MCF-7和SW-480细胞株具有一定的抑制活性。     

Phylogenetic relationships of species in <Emphasis Type="Italic">Pseudoroegneria</Emphasis> (Poaceae: Triticeae) and related genera inferred from nuclear rDNA ITS (internal transcribed spacer) sequences

To evaluate the phylogenetic relationships of species in Pseudoroegneria and related genera, the nuclear ribosomal internal transcribed spacer (ITS) sequences were analyzed for eighteen Pseudoroegneria (St), two Elytrigia (E ^e St), two Douglasdeweya (StP), three Lophopyrum (E ^e and E ^b ), three Agropyron (P), two Hordeum (H), two Australopyrum (W) and two Psathyrostachys (Ns) accessions. The main results were: (i) Pseudoroegneria gracillima, P. stipifolia, P. cognata and P. strigosa (2x) were in one clade, while P. libanotica, P. tauri and P. spicata (2x) were in the other clade, indicating there are the differentiations of St genome among diploid Pseudoroegneria species; (ii) P. geniculata ssp. scythica, P. geniculata ssp. pruinifera, Elytriga caespitosa and Et. caespitosa ssp. nodosa formed the E ^e St clade with 6-bp indel in ITS1 regions; and (iii) Douglasdeweya wangii, D. deweyi, Agropyron cristatum and A. puberulum comprised the P clade. It is unreasonable to treat P. geniculata ssp. scythica and P. geniculata ssp. pruinifera as the subspecies of P. geniculata, and they should be transferred to a new genus Trichopyrum, which consists of species with E ^e St genomes. It is also suggested that one of the diploid donor of D. wangii and D. deweyi is derived from Agropyron species, and it is reasonable to treat tetraploid species with StP genomes into Douglasdeweya.