(10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic Acid Methyl Ester as an Anti-inflammatory Compound from Ehretia dicksonii

The methanol extract of Ehretia dicksonii provided (10E,12Z,15Z)-9-hydroxy-10,12,15-octadecatrienoic acid methyl ester (1) which was isolated as an anti-inflammatory compound. Compound 1 suppressed 12-O-tetradecanoyl-phorbol-13-acetate (TPA)-induced inflammation on mouse ears at a dose of 500 μg (the inhibitory effect (IE) was 43%). Linolenic acid methyl ester did not inhibit this inflammation at the same dose. However, the related compounds of 1, (9Z,11E)-13-hydroxy-9,11-octadecadienoic acid (5) and (9Z,11E)- 13-oxo-9,11-octadecadienoic acid (6), showed potent activity (IE_{500 μg} of 63% and 79%, respectively). Compounds 1, 4 ((9Z,12Z,14E)-16-hydroxy-9,12,14-octadecatrienoic acid), 5 and 6 also showed inhibitory activity toward soybean lipoxygenase at a concentration of 10 μg/ml.     

BACE1 (Beta‐Secretase) Inhibitory Phenolic Acids and a Novel Sesquiterpenoid from Homalomena occulta

Four phenolic acids, namely 2‐[(Z)‐heptadec‐11‐enyl]‐6‐hydroxybenzoic acid ( 1 ), 2‐[(6Z,9Z,12Z)‐heptadeca‐6,9,12‐trienyl]‐6‐hydroxybenzoic acid ( 2 ), 2‐[(9Z,12Z)‐heptadeca‐9,12‐dienyl]‐6‐hydroxybenzoic acid ( 3 ), and 2‐hydroxy‐6‐(12‐phenyldodecyl)benzoic acid ( 4 ), and one sesquiterpene, asperpenoid ( 5 ), were isolated from the 95% EtOH extract of the roots of Homalomena occulta, among which 1, 2 , and 5 represent new compounds. Further, the phenolic acids 1 – 4 exhibited BACE1 (β‐secretase) inhibitory activity with IC₅₀ values of 6.23±0.94, 6.28±0.63, 7.93±0.38, and 7.65±0.62 μM , respectively.     

Synthesis and Biological Activity of Methyl 3-Demethyl-Abscisate and Its Related Analogs

To elucidate the role of the methyl substituent on the side chain of abscisic acid (ABA), we synthesized (2Z,4E)-3-demethyl-α-ionylideneacetic acid (4) and its related analogs, methyl (2Z)-3-demethyl-β-ionylideneacetate 1′,2′-epoxide (9) and methyl (2Z) and (2E)-3-demethyl-abscisate (12) and (13). The biological assay of these compounds suggested that the 3-methyl group on the side chain of ABA was indispensable to biological activity.     

Unusual fatty acids in the lipids from organs and cell cultures ofPetroselinum crispum

The lipids of seeds, leaves, and roots of parsley,Petroselinum crispum, and of heterotrophic as well as photomixotrophic cell cultures of this plant were characterized with the aim of finding a system for studying the biosynthesis of unusual fatty acids. It was found that (Z)-6-octadecenoic acid, petroselinic acid, which is the typical constituent fatty acid of triacylglycerols in seeds, occurs only in small proportions, if at all, in leaves, roots, and cell cultures of parsley. In all lipid classes studied petroselinic acid is accompanied by its (Z)-9- and (Z)-11-isomers, oleic and vaccenic acid, respectively. The phosphatidylcholines, phosphatidylethanolamines, and triacylglycerols of both heterotrophic and photomixotrophic callus cultures contain no petroselinic acid but rather oleic and vaccenic acids in equal ratios. Thus, cell cultures of parsley appear to be suitable for studying the biosynthesis of vaccenic acid. The constituent octadecadienoic acids in the lipids of various tissues and cell cultures of parsley consist almost exclusively of the (Z),(Z)-9,12-isomer, linoleic acid, which is derived from oleic acid. (Z),(Z)-6,9- and (Z),(Z)-11,14-Octadecadienoic acids, which could be expected as products of desaturation of petroselinic and vaccenic acids, were not found in any of the lipids of organs and cell cultures investigated.Abbreviations TLC thin-layer chromatography - GLC gas-liquid chromatography     

Identification of novel sex pheromone components from a tussock moth, Euproctis pulverea

Two EAG-active compounds were found in the solvent extract of abdominal tips of virgin females of the tussock moth Euproctis pulverea (Leech) (Lepidoptera: Lymantriidae), and identified as (Z,Z,Z)-11,14,17-icosatrienyl isobutyrate and (Z,Z,Z)-11,14,17-icosatrienyl 4-methylvalerate at 190 and 80 ng female^–1, respectively, by means of GC-MS analyses and chemical derivatization. Esters of n-butyric acid, n-valeric acid, n-hexanoic acid and a methylheptanoic acid were also found at 3, 2, 0.4 and 9 ng female^–1 as minor EAG-inactive compounds. Two active compounds were also detected in the hexane extract of female anal tufts at 17 and 6 ng female^–1, respectively. In Okinawa, the binary blend of the synthetic compounds attracted male moths to the sticky traps, but single compounds did not. The significance of these findings in relation to parasitism by Telenomus euproctidis (Hymenoptera: Scelionidae) is discussed.     

A comparison of responses from olfactory receptor neurons of<Emphasis Type="Italic"> Heliothis subflexa</Emphasis> and<Emphasis Type="Italic"> Heliothis virescens</Emphasis> to components of their sex pheromone

Single-cell electrophysiological recordings were obtained from olfactory receptor neurons in sensilla trichodea on male antennae of the heliothine species Heliothis subflexa and the closely related congener H. virescens. A large percentage of sensilla (72% and 81%, respectively, of all sensilla sampled) contained a single odor-responsive receptor neuron tuned to the major pheromone component of both species, Z-11-hexadecenal. A second population of sensilla on H. subflexa antennae (18%) housed receptor neurons that were tuned to Z-9-hexadecenal but also responded with less sensitivity to Z-9-tetradecenal. A similar population of sensilla (4%) on H. virescens male antennae housed receptor neurons that were shown to be tuned specifically only to Z-9-tetradecenal, with no response to even high dosages of Z-9-hexadecenal. A third population of sensilla (comprising 8% and 16% of the sensilla sampled in H. subflexa and H. virescens, respectively) housed two olfactory receptor neurons, one of which was tuned to Z-11-hexadecenyl acetate and the other tuned to Z-11-hexadecenol. In H. subflexa the Z-11-hexadecenyl acetate-tuned neuron also responded to Z-9-tetradecenal with nearly equivalent sensitivity. The behavioral requirements of males of these two species for distinct pheromonal blends was, therefore, reflected by the subtle differences in the tuning properties of antennal olfactory receptor neurons.Abbreviations MGC macroglomerular complex - ORN olfactory receptor neuron - Z9–14:Ald (Z)-9-tetradecenal - Z9–16:Ald (Z)-9-hexadecenal - Z11–16:Ac (Z)-11-hexadecenyl acetate - Z11–16:Ald (Z)-11-hexadecenal - Z11–16:OH (Z)-11-hexadecenol     

Neurons discovered in male Helicoverpa zea antennae that correlate with pheromone-mediated attraction and interspecific antagonism

Responses of single receptor neurons in the antennae of male Helicoverpa zea to sex pheromone components and to behavioral antagonists were recorded using a cut-sensillum extracellular recording technique. Three types of sensilla were identified from sampling 325 male-specific sensilla trichodea located at the lateral edge of antennomeres. The majority of these sensilla (71%) contained a receptor neuron tuned to the principal sex pheromone component (Z)-11-hexadecenal. A second sensillar type (10%) contained a receptor neuron that responded only to (Z)-9-tetradecenal. A third sensillar type (19%) contained a large-spiking neuron tuned to the secondary pheromone component (Z)-9-hexadecenal, but this neuron also could be stimulated to equivalent spike frequencies by the same emitted amounts of (Z)-9-tetradecenal. A smaller-spiking neuron in this sensillar type responded to two compounds known to act only as behavioral antagonists, (Z)-11-hexadecen-1-ol and (Z)-11-hexadecenyl acetate, and to (Z)-9-tetradecenal. Cross-adaptation studies confirmed the presence of one large- and one small-spiking neuron in the third sensillar type. Dose-response studies correlated to collected stimuli amounts showed that the large-spiking neuron in the third sensillar type was equally tuned to (Z)-9-hexadecenal and (Z)-9-tetradecenal, whereas the smaller-spiking neuron was far more sensitive to (Z)-11-hexadecen-1-ol and to (Z)-11-hexadecenyl acetate than to (Z)-9-tetradecenal. Accepted: 29 September 1997     

Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, <Emphasis Type="Italic">Phaeodactylum tricornutum</Emphasis>

One solution to the global crisis of antibiotic resistance is the discovery of novel antimicrobial compounds for clinical application. Marine organisms are an attractive and, as yet, relatively untapped resource of new natural products. Cell extracts from the marine diatom, Phaeodactylum tricornutum, have antibacterial activity and the fatty acid, eicosapentaenoic acid (EPA), has been identified as one compound responsible for this activity. During the isolation of EPA, it became apparent that the extracts contained further antibacterial compounds. The present study was undertaken to isolate these additional antibacterial factors using silica column chromatography and reverse-phase high-performance liquid chromatography. Two antibacterial fractions, each containing a pure compound, were isolated and their chemical structures were investigated by mass spectrometry and nuclear magnetic resonance spectroscopy. The antibacterial compounds were identified as the monounsaturated fatty acid (9Z)-hexadecenoic acid (palmitoleic acid; C16:1 n-7) and the relatively unusual polyunsaturated fatty acid (6Z, 9Z, 12Z)-hexadecatrienoic acid (HTA; C16:3 n-4). Both are active against Gram-positive bacteria with HTA further inhibitory to the growth of the Gram-negative marine pathogen, Listonella anguillarum. Palmitoleic acid is active at micro-molar concentrations, kills bacteria rapidly, and is highly active against multidrug-resistant Staphylococcus aureus. These free fatty acids warrant further investigation as a new potential therapy for drug-resistant infections.     

Isolation and spectral characterization of thermally generated multi-Z-isomers of lycopene and the theoretically preferred pathway to di-Z-isomers

Lycopene has a large number of geometric isomers caused by E/Z isomerization at arbitrary sites within the 11 conjugated double bonds, offering varying characteristics related to features such as antioxidant capacity and bioavailability. However, the geometric structures of only a few lycopene Z-isomers have been thoroughly identified from natural sources. In this study, seven multi-Z-isomers of lycopene, (9Z,13′Z)-, (5Z,13Z,9′Z)-, (9Z,9′Z)-, (5Z,13′Z)-, (5Z,9′Z)-, (5Z,9Z,5′Z)-, and (5Z,9Z)-lycopene, were obtained from tomato samples by thermal isomerization, and then isolated by elaborate chromatography, and fully assigned using proton nuclear magnetic resonance. Moreover, the theoretically preferred pathway from (all-E)-lycopene to di-Z-isomers was examined with a computational approach using a Gaussian program. Fine-tuning of the HPLC separation conditions led to the discovery of novel multi-Z-isomers, and whose formation was supported by advanced theoretical calculations.     

Constituents of Limonia acidissima inhibit LPS-induced nitric oxide production in BV-2 microglia

The ethyl acetate (EtOAc) soluble fraction of the 85% ethanol (EtOH) extract of the dried bark of Limonia acidissima potently inhibited nitric oxide (NO) production in lipopolysaccharide (LPS) activated BV-2 cells, a microglial cell line. Bioassay-guided column chromatography separation afforded a new stereoisomer of neolignan, (7’E)-(7R,8S)-4-hydroxy-3,5’-dimethoxy-4’,7-epoxy-8,3’-neolig-7’-en-9,9’-diyil diacetate (1), together with two known lignans, (+)-yangambin (2) and (+)-syringaresinol (3), three known triterpenoids, hederatriol (4), basic acid methyl ester (5), and 3β-hydroxyolean-12-en-11-one (6), and four known fatty acid derivatives, cascarillic acid (7), (+)-α-dimorphecolic acid (8), 8(R)-hydroxylinoleic acid (9), and (6Z,9Z,12Z)-pentadecatrienoic acid (10). The structure of the new compound 1 was elucidated by detailed analysis of spectroscopic data and circular dichroism (CD) spectroscopy. Compounds 1, 3-6, and 8-10 isolated from L. acidissima significantly reduced NO production in LPS-stimulated BV-2 microglia cells.     

Monoenyl hydrocarbons in female body wax of the yellow peach moth as synergists of aldehyde pheromone components

The non-polar components of female body wax and pheromone gland extracts of the yellow peach moth synergistically enhanced male behavioral responses from close to pheromone sources in wind tunnel tests when mixed with an aldehyde pheromone blend. When the non-polar fractions (NPFs) of female body wax were further separated by column chromatography, synergistic activities were found in the 3 and 50% ether in hexane fractions, and they additively increased male responses. The main components of the first fraction were (Z)-9-tricosene, (Z)-9-pentacosene, (Z)-9-heptacosene, (Z)-9-nonacosene and (Z)-9-hentriacontene. Only (Z)-9-heptacosene showed a significant synergistic effect in enhancing male responses, but the other components had no effect. A mixture of the five monoenyl hydrocarbons lost activity at lower doses than 5 ng. Natural ratios of these hydrocarbons in the female body wax and pheromone gland extracts were similar, but the amount of (Z)-9-heptacosene in the female body wax was significantly higher than in the pheromone gland extracts. We conclude that (Z)-9-heptacosene increases male responses to aldehyde pheromones, and unknown component(s) in the 50% ether in the hexane fraction are required for full synergistic enhancement by the NPFs of the female body wax and the pheromone gland extracts.     

A general method for preparation of N‐Boc‐protected or N‐Fmoc‐protected α,β‐didehydropeptide building blocks and their use in the solid‐phase peptide synthesis

N‐(tert‐butyloxycarbonyl) or N‐(9‐fluorenylmethoxycarbonyl) dipeptides with C‐terminal (Z)‐α,β‐didehydrophenylalanine (?^ZPhe), (Z)‐α,β‐didehydrotyrosine (?^ZTyr), (Z)‐α,β‐didehydrotryptophan (?^ZTrp), (Z)‐α,β‐didehydromethionine (?^ZMet), (Z)‐α,β‐didehydroleucine (?^ZLeu), and (Z/E)‐α,β‐didehydroisoleucine (?^Z/EIle) were synthesised from their saturated analogues via oxidation of intermediate 2,5‐disubstituted‐oxazol‐5‐(4H)‐ones (also known as azlactones) with pyridinium tribromide followed by opening of the produced unsaturated oxazol‐5‐(4H)‐one derivatives in organic‐aqueous solution with a catalytic amount of trifluoroacetic acid or by a basic hydrolysis. In all cases, a very strong preference for Z isomers of α,β‐didehydro‐α‐amino acid residues was observed except of the ΔIle, which was obtained as the equimolar mixture of Z and E isomers. Reasons for the (Z)‐stereoselectivity and the increased stability of the aromatic α,β‐didehydro‐α‐amino acid residue oxazol‐5‐(4H)‐ones over the corresponding aliphatic ones are also discussed. It is the first use of such a procedure to synthesise peptides with the C‐terminal unsaturated residues and a peptide with 2 consecutive ΔPhe residues. This approach is very effective especially in the synthesis of peptides with aliphatic α,β‐didehydro‐α‐amino acid residues that are difficult to obtain by other methods. It allowed the first synthesis of the ?Met residue. It is also more cost‐effective and less laborious than other synthesis protocols. The dipeptide building blocks obtained were used in the solid‐phase synthesis of model peptides on a polystyrene‐based solid support. Peptides containing aromatic α,β‐didehydro‐α‐amino acid residues were obtained with PyBOP or TBTU as a coupling agent with good yields and purities. In the case of aliphatic α,β‐didehydro‐α‐amino acid residues, a good efficiency was achieved only with DPPA as a coupling agent.     

DHA Metabolism: Targeting the Brain and Lipoxygenation

Docosahexaenoic acid (DHA), the end-product of the metabolism of omega-3 family fatty acids, is the main polyunsaturated fatty acid of the brain, but its accumulation is incompletely understood. This paper reviews how it could accumulate through specific uptake of DHA-containing lysophosphatidylcholine (LysoPC-DHA). DHA migrates very easily from the sn-2 position of LysoPC, which could be considered as the physiological form of polyunsaturated LysoPC, to the sn-1 position, which is much more stable. An approach preventing migration by acetylating the sn-1 position, while retaining the main physico-chemical properties of the carrier, is described. Also, the double lipoxygenation and bond-isomerization of DHA into 10(S),17(S)-docosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid, named PDX, by soybean lipoxygenase is described. As in other E,Z,E conjugated trienes, PDX is shown to inhibit human blood platelet aggregation at submicromolar concentrations.     

Metabolism of (2Z,4E)-γ-Ionylideneethanol and (2Z,4E)-γ-Ionylideneacetic Acid in Cercospora cruenta

[2–¹⁴C]-(2Z,4E)-γ-Ionylideneethanol and [2–¹⁴C]-(2Z,4E)-γ-ionylideneacetic acid were converted by Cercospora cruenta to [2–¹⁴C]-(2Z,4E)-1′,4′-dihydroxy-γ-ionylideneacetic acid and [2-¹⁴C]-(2Z,4E)-4′-hydroxy-γ-ionylideneacetic acid, which are intermediates of ABA biosynthesis in C. cruenta.     

Ionylideneacetic Acids and Abscisic Acid Biosynthesis by Cercospora rosicola

Several compounds having the basic α-ionylideneacetic acid structure were tested in Cercospora rosicola resuspensions. At 100 μm, all the compounds inhibited abscisic acid (ABA) biosynthesis. Time studies with unlabelled and deuterated (2Z,4E)- and (2E,4E)-α-ionylideneacetic acids showed rapid conversions into both (2Z,4E)- and (2E,4E)-4′-keto-α-ionylideneacetic acids as major products. Incorporation of the label into ABA was specific for the 2Z,4E-isomer. Minor products, identified by GC-MS, were (2Z,4E)- and (2E,4E)-4′-hydroxy-α-ionylideneacetic acids and (2Z,4E)-1′-hydroxy-α-ionylideneacetic acid. The conversion to (2Z,4E)-l′-hydroxy-α-ionylideneacetic acid has not been previously reported and was specific for the 2Z,4E-isomer. A time study for the conversion of methyl esters of [²H₃]-(2Z,4E)- and [²H₃]-(2E,4E)-4′-keto-α-ionylideneacetates showed a slow introduction of the l′-hydroxyl group and specificity for 2Z,4E-isomer. Conversion of the ethyl esters of (2Z,4E)- and (2E,4E)-l′-hydroxy-α-ionylideneacetates into the ethyl esters of both ABA and (2E,4E)-ABA demonstrated that ABA can be formed by oxidation of the 4′-position after the insertion of the 1′-hydroxy group. The ethyl 1′-hydroxy acids were also isomerized to the corresponding ethyl (2Z,4E)- and ethyl (2E,4E)-3′-hydroxy-β-ionylideneacetates. Ethyl (2Z,4E)-1′-hydroxy acid also gave small amounts of ethyl l′,4′-trans-diol of ABA. These results suggest that ABA may be formed through a (2Z,4E)-1′-hydroxy-α-ionylidene-type intermediate in addition to the previously proposed route through (2Z,4E)-4′-keto-α-ionylideneacetic acid.     

Biotransformation of linoleic acid with the Candida tropicalis M25 mutant

Linoleic acid was transformed by mutant Candida tropicalis M25 and transformations were studied in batch and fed-batch cultures. Cofermentations with palmitic acid as inducer of the fatty acid degradation pathway were performed. Besides the (Z),(Z)-octadeca-6,9-dienedioic acid, (Z),(Z)-3-hydroxyoctadeca-9,12-dienedioic acid and (Z),(Z)-3-hydroxytetradeca-5,8-dienedioic acid were obtained as the main fermentation products. The maximum concentrations of (Z),(Z)-octadeca-6,9-dienedioic acid and (Z),(Z)-3-hydroxyoctadeca-9,12-dienedioic acid reached values of 6.4 g/l and 6.9 g/l respectively. The structures of the products were characterized by chemical and spectroscopic methods. The configuration of the double bonds was not changed during bioconversion. As only one regioisomer of the hydroxylated fatty acid was detected, the hydroxylation is site-specific. Received: 11 November 1996 / Received revision: 11 February 1997 / Accepted: 24 February 1997     

Production of 8,11‐dihydroxy and 8‐hydroxy unsaturated fatty acids from unsaturated fatty acids by recombinant Escherichia coli expressing 8,11‐linoleate diol synthase from Penicillium chrysogenum

Hydroxy unsaturated fatty acids can be used as antimicrobial surfactants. 8,11‐Linoleate diol synthase (8,11‐LDS) catalyzes the conversion of unsaturated fatty acid to 8‐hydroperoxy unsaturated fatty acid, and it is subsequently isomerized to 8,11‐dihydroxy unsaturated fatty acid by the enzyme. The optimal reaction conditions of recombinant Escherichia coli expressing Penicillium chrysogenum 8,11‐LDS for the production of 8,11‐dihydroxy‐9,12(Z,Z)‐octadecadienoic acid (8,11‐DiHODE), 8,11‐dihydroxy‐9,12,15(Z,Z,Z)‐octadecatrienoic acid (8,11‐DiHOTrE), 8‐hydroxy‐9(Z)‐hexadecenoic acid (8‐HHME), and 8‐hydroxy‐9(Z)‐octadecenoic acid (8‐HOME) were pH 7.0, 25°C, 10 g/L linoleic acid, and 20 g/L cells; pH 6.0, 25°C, 6 g/L α‐linolenic acid, and 60 g/L cells; pH 7.0, 25°C, 8 g/L palmitoleic acid, and 25 g/L cells; and pH 8.5, 30°C, 6 g/L oleic acid, and 25 g/L cells, respectively. Under these optimized conditions, the recombinant cells produced 6.0 g/L 8,11‐DiHODE for 60 min, with a conversion of 60% (w/w) and a productivity of 6.0 g/L/h; 4.3 g/L 8,11‐DiHOTrE for 60 min, with a conversion of 72% (w/w) and a productivity of 4.3 g/L/h; 4.3 g/L 8‐HHME acid for 60 min, with a conversion of 54% (w/w) and a productivity of 4.3 g/L/h; and 0.9 g/L 8‐HOME for 30 min, with a conversion of 15% (w/w) and a productivity of 1.8 g/L/h. To best of our knowledge, this is the first report on the biotechnological production of 8,11‐DiHODE, 8,11‐DiHOTrE, 8‐HHME, and 8‐HOME. © 2017 American Institute of Chemical Engineers Biotechnol. Prog., 33:390–396, 2017     

Diversity of Halogenated Secondary Metabolites in Okinawan Aplysia argus Including 12-Hydroxypinnaterpene C and Their Feeding Targets

A new irieane-type diterpene, 12-hydroxypinnaterpene C ( 1 ), and 21 known compounds, angasiol acetate ( 2 ), angasiol ( 3 ), 11-deacetylpinnaterpene C ( 4 ), palisadin A ( 5 ), 12-acetoxypalisadin B ( 6 ), 12-hydroxypalisadin B ( 7 ), aplysistatin ( 8 ), luzodiol ( 9 ), 5-acetoxy-2-bromo-3-chloro-chamigra-7(14),9-dien-8-one ( 10 ), neoirietriol ( 11 ), neoirietetraol ( 12 ), (3Z)-laurenyne ( 13 ), cupalaurenol ( 14 ), cupalaurenol acetate ( 15 ), (3Z)-venustinene ( 16 ), 10-hydroxykahukuene B ( 17 ), aplysiol B ( 18 ), (3Z)-13-epipinnatifidenyne ( 19 ), 3Z,6R,7R,12S,13S-obtusenyne ( 20 ), (3Z,9Z)-7-chloro-6-hydroxy-12-oxo-pentadeca-3,9-dien-1-yne ( 21 ), and cholest-7-en-3,5,7-triol ( 22 ) were isolated from the digestive diverticula of Aplysia argus from the Ikei Island in Okinawa, Japan. The structures of these compounds were determined using spectroscopic methods such as NMR and HR-ESI-MS. These compounds were tested for their antibacterial activity against the phytopathogen Ralstonia solanacearum. Compounds 11 and 21 exhibited antibacterial activity at 30 μg/disc. In this study, we also discuss the types of red algae that A. argus feeds on in the shallow waters of Okinawa Prefecture.     

Chemical Constituents of the Rare Cliff Plant Oresitrophe rupifraga and Their Antineuroinflammatory Activity

Four new ( 1 – 4 ) and thirteen known ( 5 – 17 ) compounds were isolated from a rare cliff plant, Oresitrophe rupifraga. Based on spectroscopic evidence, the new structures were established to be [(2S,3R,4R)‐4‐(4‐methoxybenzyl)‐2‐(4‐methoxyphenyl)‐tetrahydrofuran‐3‐yl]methanol ( 1 ), (3α)‐23‐(acetyloxy)‐3‐hydroxyolean‐12‐en‐29‐oic acid ( 2 ), 3α,23‐(isopropylidenedioxy)olean‐12‐en‐29‐oic acid ( 3 , artifact of isolation), and (3β,15β)‐3‐hydroxycholest‐5‐en‐15‐yl β‐d ‐glucopyranoside ( 4 ), respectively. Among the isolates, compounds 1 , 4 , epieudesmin ( 7 ), and 1‐O‐(9Z,12Z,15Z‐octadecatrienoyl)glycerol ( 17 ) were found to show significant antineuroinflammatory effects by inhibiting the NO production in lipopolysaccharide (LPS)‐stimulated murine BV‐2 microglial cells, with IC₅₀ values of 7.21, 9.39, 4.96, and 8.51 μm , respectively.     

华石斛化学成分研究(Ⅱ)

海南特有植物华石斛(Dendrobium sinense)的化学成分和药理活性研究报道较少。为了深入研究华石斛的化学成分,该研究采用MCI小孔树脂柱色谱、硅胶柱色谱和Sephadex LH-20柱色谱等多种现代分离纯化技术,从其全草乙醇提取物的乙酸乙酯部位中分离纯化了10个化合物。结果表明:对分离纯化得到的10个化合物鉴定为罗汉松脂素(1)、4,5-二羟基-2,3-二甲氧基-9,10-二氢菲(2)、华石斛素C(3)、对甲氧基苯乙醇(4)、顺式对羟基肉桂酸乙酯(5)、对羟基苯丙酸乙酯(6)、丁香醛(7)、3-羟基苯甲醛(8)、3,9-dihydroxy-megastigma-5-ene(9)和(9Z,12Z)-9,12-二烯十八碳酸甲酯(10)。其中,首次从华石斛中分离得到的有化合物1、4-6、8-10。通过体外抑制乙酰胆碱酯酶活性实验发现,化合物2、4和化合物9能够使乙酰胆碱酯酶活力下降。