Sesquiterpenoids and Diterpenoids from Chloranthus anhuiensis

A phytochemical investigation of the roots of Chloranthus anhuiensis afforded three new sesquiterpene lactones, chloraniolide A ( 1 ), (3R)‐3‐hydroxyatractylenolide III ( 2 ), and 8β‐hydroxy‐1‐oxoeudesma‐3,7(11)‐dien‐12,8α‐olide ( 3 ), and two new diterpenoids, (12R,13E)‐15‐(acetoxy)‐12‐hydroxylabda‐8(20),13‐dien‐19‐oic acid ( 4 ) and (12S,13E)‐15‐(acetoxy)‐12‐dihydroxylabda‐8(20),13‐dien‐19‐oic acid ( 5 ), as well as 17 known sesquiterpenoid and diterpenoid compounds. Their structures were established on the basis of 1D‐ and 2D‐NMR, and other spectroscopic analyses.     

Terpenoids from Rhizomes of Alpinia japonica Inhibiting Nitric Oxide Production

A new sesquiterpenoid, 1 , and three new diterpenoids, 3 – 5 , along with five known compounds, 2 and 6 – 9 , were isolated from rhizomes of Alpinia japonica. The structures of the new compounds were determined as (1R,4R,6S,7S,9S)‐4α‐hydroxy‐1,9‐peroxybisabola‐2,10‐diene ( 1 ), methyl (12E)‐16‐oxolabda‐8(17),12‐dien‐15‐oate ( 3 ), (12R)‐15‐ethoxy‐12‐hydroxylabda‐8(17),13(14)‐dien‐16,15‐olide ( 4 ), and methyl (11E)‐14,15,16‐trinorlabda‐8(17),11‐dien‐13‐oate ( 5 ) by means of spectroscopic data. The absolute configurations at C(4) in 1 and C(12) in 4 were deduced from the circular dichroism (CD) data of the in situ‐formed [Rh₂(CF₃COO)₄] complexes. Inhibitory effects of the isolates on NO production in lipopolysaccharide‐induced RAW264.7 macrophages were evaluated, and 2 – 4, 6 , and 7 were found to exhibit inhibitory activities with IC₅₀ values between 14.6 and 34.3 μM .     

Benzopyran Derivatives and an Aliphatic Compound from a Mangrove Endophytic Fungus Penicillium citrinum QJF‐22

Two new benzopyran derivatives, (2R,4S)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol and (2S,4R,2′S,4′R)‐4,4′‐oxybis(5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran), and a new aliphatic compound, (3E,5Z,8S,10E)‐8‐hydroxytrideca‐3,5,10,12‐tetraen‐2‐one, together with three known benzopyran derivatives, were obtained from a mangrove endophytic fungus Penicillium citrinum QJF‐22 collected in Hainan island. Their structures were determined by analysis of spectroscopic data and the relative configuration of (2R,4S)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol was also confirmed by single‐crystal X‐ray diffraction. The absolute configurations of four compounds were established by comparison of ECD spectra to calculations. The configuration of (3E,5Z,8S,10E)‐8‐hydroxytrideca‐3,5,10,12‐tetraen‐2‐one was confirmed by comparison of optical value to the similar compound. The configurations of the compounds (2S,4S)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol and (2R,4R)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol were first determined. (3R,4S)‐3,4,8‐Trihydroxy‐3,4‐dihydronaphthalen‐1(2H)‐one exhibited moderate inhibitory effects on LPS‐induced NO production in RAW264.7 cells with IC₅₀ of 44.7 μM, and without cytotoxicity to RAW264.7 cells within 50 μM.     

Four New Tirucallane Triterpenoids from the Fruits of Melia azedarach and Their Cytotoxic Activities

Four new tirucallane triterpenoids, (21S,23R,24R)‐21,23‐epoxy‐21,24‐dihydroxy‐25‐methoxytirucall‐7‐en‐3‐one ( 2 ), (3S,21S,23R,24S)‐21,23‐epoxy‐21,25‐dimethoxytirucall‐7‐ene‐3,24‐diol ( 8 ), (21S,23R,24R)‐21,23‐epoxy‐24‐hydroxy‐21‐methoxytirucalla‐7,25‐dien‐3‐one ( 11 ), and (21S,23R,24R)‐21,23‐epoxy‐21,24‐dihydroxytirucalla‐7,25‐dien‐3‐one ( 12 ), along with 16 known analogues, 1 , 3  –  7 , 9  –  10 , and 13  –  20 , were isolated from the fruits of Melia azedarach. Their structures were elucidated by spectroscopic methods including 1D‐ and 2D‐NMR techniques and mass spectrometry. These compounds were evaluated for their cytotoxicities against HepG2 (liver), SGC7901 (stomach), K562 (leukemia), and HL60 (leukemia) cancer cell lines. Compound 20 exhibited potent cytotoxicity against HepG2 and SGC7901 cancer cells with the IC₅₀ values of 6.9 and 6.9 μm , respectively.     

Syntheses,Characterizations, and Biological Activities of Tetradeca‐4,8‐dien‐1‐yl Acetates as Sex Attractants of Leaf‐Mining Moth of the Genus Phyllonorycter (Lepidoptera: Gracillariidae)

The four possible isomers of tetradeca‐4,8‐dien‐1‐yl acetate and corresponding alcohols were synthesized stereoselectively by synthetic routes employing Wittig coupling reaction for the preparation of (Z,E)‐ and (Z,Z)‐isomers, and alkylation of terminal alkynes for the preparation of (E,E)‐ and (E,Z)‐isomers as the key steps. Synthetic products were characterized by ¹³C‐ and ¹H‐NMR spectroscopy as well as mass‐spectrometric methods. All four isomers gave distinctive mass spectra where m/z 81 fragments clearly dominated. Elution order, followed by retention index presented in parenthesis, of tetradeca‐4,8‐dien‐1‐ols was determined as (Z,Z) (2082.1), (Z,E) (2082.8), (E,E) (2083.1), and (E,Z) (2083.2) from unpolar SPB‐1 column, and as (E,E) (2210.2), (Z,E) (2222.1), (E,Z) (2223.4), and (Z,Z) (2224.7) from polar DB‐WAX column. The isomers of tetradeca‐4,8‐dien‐1‐yl acetates eluted in the order of (Z,Z) (2176.1), (Z,E) (2178.4), (E,Z) (2185.9), and (E,E) (2186.4) from SPB‐1, and (Z,E) (2124.3), (E,E) (2157.7), (Z,Z) (2128.9), and (E,Z) (2135.9) from DB‐WAX columns. Field‐screening tests for attractiveness of tetradeca‐4,8‐dien‐1‐yl acetates revealed that (4Z,8E)‐tetradeca‐4,8‐dien‐1‐yl acetate significantly attracted Phyllonorycter coryli and Chrysoesthia drurella males. (4E,8E)‐Tetradeca‐4,8‐dien‐1‐yl acetate was the most efficient attractant for Ph. esperella and Ph. saportella males, and (4E,8Z)‐tetradeca‐4,8‐dien‐1‐yl acetate was attractive to Ph. cerasicolella males.     

Cynasibirolide A,One New Humulanolide Sesquiterpene from Cynanchum acutum subsp. sibiricum

Cynasibirolide A ( 1 ), one new humulanolide sesquiterpene, together with four known analogs, asteriscanolide ( 2 ), (1S,8S)-8-hydroxyhumula-2Z,6E,9E-trien-1,12-olide ( 3 ), (1S,7R)-8-oxohumula-2Z,9E-dien-1,12-olide ( 4 ), and (+)-6,7,9,10-tetrahydroasteriscunolide ( 5 ) were isolated from the roots and rhizomes of Cynanchum acutum subsp. sibiricum. Their structures and configurations were elucidated by spectroscopic methods, including 2D-NMR techniques, and the structure of 1 was confirmed by single-crystal X-ray diffraction. All compounds were evaluated for their anti-complementary activity in vitro, and compound 3 exhibited anti-complement effect with CH₅₀ value of 0.45 mM.     

Oxygenated verticillene derivatives from Bursera suntui

Medium polarity fractions of the hexane extracts of the stems of Bursera suntui afforded six previously known (1-6) and four hitherto unknown verticillane derivatives: (1S,3Z,7S,8S,11S,12S)-(+)-7,8-epoxyverticill-3-en-12,20-diol (7), (1S,3Z,7S,8S,11S,12S)-(+)-7,8-epoxyverticill-3-en-12,20-diol 20-acetate (8), (1S,3Z,7S,11S,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol (9), and (1S,3Z,7S,11S,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol 20-acetate (10). Acetylation of 9 and 10 yielded (1S,3Z,7S,11S,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol 7,20-diacetate (11), while hydrolysis of 8 gave 7. The structures and stereochemistry of 7-11 were established by spectroscopic analyses, particularly by 1D and 2D NMR spectra and HRESIMS. The conformational preferences of 7-11 were studied by molecular mechanics modelling employing the Monte Carlo protocol followed by B3LYP/DGDZVP DFT calculation, thus supporting the observed ¹H NMR NOESY cross peaks.     

Dolabellane diterpenoids from Aglaia odorata

Dolabellane diterpenoids, (1R,3E,7E,10S,11S,12R)-dolabella-3,7-dien-10,18-diol (1), (1R,3S,7E,11S,12R)-dolabella-4(16),7-dien-3,18-diol (2), (1R,7E,11S,12R)-18-hydroxydolabella-4(16),7-dien-3-one (3), (1R,3S,4S,7E,11S,12R)-3,4-epoxydolabella-7-en-18-ol (4), and (1R,3R,7E,11S,12R)-dolabella-4(16),7,18-trien-3-ol (5), were obtained from the ornamental plant Aglaia odorata. Their structures were characterized on the basis of spectroscopic analyses and further confirmed by X-ray diffraction. Compounds 1 and 5 showed weak cytotoxicity against the human myeloid leukemia HL-60, hepatocellular carcinoma SMMC-7721, and lung cancer A-549 cells.     

Secondary Metabolites and Antimycobacterial Activities from the Roots of Ficus nervosa

Bioassay‐guided fractionation of the active AcOEt‐soluble layer led to the isolation of two new pyranocoumarins, 3‐hydroxyxanthyletin ( 1 ) and 3‐methoxyxanthyletin ( 2 ), along with 22 known compounds including four simple coumarins, i.e., xanthyletin ( 3 ), umbelliferone ( 4 ), scopoletin ( 5 ), and (+)‐(S)‐marmesin ( 6 ); nine flavonoids, i.e., carpachromene ( 7 ), parvisoflavone B ( 8 ), alpinumisoflavone ( 9 ) genistein ( 10 ), 2′‐hydroxygenistein ( 11 ), prunetin ( 12 ), cajanin ( 13 ), apigenin ( 14 ), and (2S)‐naringenin ( 15 ); three benzenoids, i.e., 4‐hydroxybenzaldehyde ( 16 ), vanillin ( 17 ), and (S)‐lasiodiplodin ( 18 ); five steroids, i.e., ergosterol peroxide ( 19 ), a mixture of 6β‐hydroxystigmast‐4‐en‐3‐one ( 20 ) and 6β‐hydroxystigmasta‐4,22‐dien‐3‐one ( 21 ), and a mixture of β‐sitosterol ( 22 ) and stigmasterol ( 23 ); and one triterpenoid, i.e., oleanolic acid ( 24 ) from the roots of Ficus nervosa. Their structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR as well as MS analyses. Among these isolates, 3‐hydroxyxanthyletin ( 1 ), genistein ( 10 ), prunetin ( 12 ), and (2S)‐naringenin ( 15 ) showed antimycobacterial activities against Mycobacterium tuberculosis H₃₇R_V in vitro with MIC values of 16, 35, 30, and ≤2.8 μg/ml, respectively.     

Chemical constituents of Papulaspora immersa, an endophyte from Smallanthus sonchifolius (Asteraceae), and their cytotoxic activity

Papulaspora immersa H. H. Hotson was isolated from roots and leaves of Smallanthus sonchifolius (Poepp. and Endl. ) H. Rob. (Asteraceae), traditionally known as Yacon. The fungus was cultured in rice, and, from the AcOEt fraction, 14 compounds were isolated. Among them, (22E,24R)‐8,14‐epoxyergosta‐4,22‐diene‐3,6‐dione ( 4 ), 2,3‐epoxy‐1,2,3,4‐tetrahydronaphthalene‐c‐1,c‐4,8‐triol ( 10 ), and the chromone papulasporin ( 13 ) were new secondary metabolites. The spectral data of the known natural products were compared with the literature data, and their structures were established as the (24R)‐stigmast‐4‐en‐3‐one ( 1 ), 24‐methylenecycloartan‐3β‐ol ( 2 ), (22E,24R)‐ergosta‐4,6,8(14),22‐tetraen‐3‐one ( 3 ), (?)‐(3R,4R)‐4‐hydroxymellein ( 5 ), (?)‐(3R)‐5‐hydroxymellein ( 6 ), 6,8‐dihydroxy‐3‐methylisocoumarin ( 7 ), (?)‐(4S)‐4,8‐dihydroxy‐α‐tetralone ( 8 ), naphthalene‐1,8‐diol ( 9 ), 6,7,8‐trihydroxy‐3‐methylisocoumarin ( 11 ), 7‐hydroxy‐2,5‐dimethylchromone ( 12 ), and tyrosol ( 14 ). Compound 4 showed the highest cytotoxic activity against the human tumor cell lines MDA‐MB435 (melanoma), HCT‐8 (colon), SF295 (glioblastoma), and HL‐60 (promyelocytic leukemia), with IC₅₀ values of 3.3, 14.7, 5.0 and 1.6 μM , respectively. Strong synergistic effects were also observed with compound 5 and some of the isolated steroidal compounds.     

Terpenes from Euphorbia antiquorum and Their in Vitro Anti‐HIV Activity

Three new compounds ( 1 – 3 ), including two euphane type triterpenes, 24,24‐dimethoxy‐25,26,27‐trinoreuphan‐3β‐ol ( 1 ) and (24S)‐24‐hydroperoxyeupha‐8,25‐dien‐3β‐ol ( 2 ), and an ent‐atisine diterpene, ent‐atisane‐3α,16α,17‐triol ( 3 ), were isolated from an acetone extract of the stems of Euphorbia antiquorum, together with eight known diterpenes ( 4 – 11 ). The structures of compounds ( 1 – 11 ) were elucidated using NMR and MS spectroscopic methods. Compound 7 showed moderate activity against HIV‐1 replication in vitro (EC₅₀ = 1.38 μm ).     

Acid-catalyzed transformation of 13(S)-hydroperoxylinoleic acid into epoxyhydroxyoctadecenoic and trihydroxyoctadecenoic acids

Acid treatment of (13S)-(9Z,11E)-13-hydroperoxy-9,11-octadecadienoic acid in tetrahydrofuran-water solvent afforded mainly (11R,12R,13S)-(Z)-12,13-epoxy-11-hydroxy-9-octadecenoic acid, diastereomeric (Z)-11,12,13-trihydroxy-9-octadecenoic acids and four isomers of (E)-9,12,13(9,10,13)-trihydroxy-10(11)-octadecenoic acid. Other minor products were oxooctadecadienoic, (E)-9(13)-hydroxy-13(9)-oxo-10(11)-octadecenoic and (E)-12-oxo-10-dodecenoic acids. A heterolytic mechanism for acid catalysis was indicated, even though most of the products characterized also have been observed as a result of homolytic decomposition of the hydroperoxide via an oxy radical. Most of the products found in this study have been observed as metabolites of (13S)-(9Z,11E)-13-hydroperoxy-9,11-octadecadenoic acid in biological systems, and analogous compounds have been reported as metabolites of (12S)-(5Z,8Z,10E, 14Z)-12-hydroperoxy-5,8,10,14-hydroperoxy-5,8,10,14-eicosatetraenoic acid in either blood platelets or lung tissue.     

Chemical Components from Phaeanthus vietnamensis and Their Inhibitory NO Production in BV2 Cells

Phaeanthus vietnamensis Bân is a well‐known medicinal plant which has been used for the treatment of various inflammatory diseases in traditional medicine. Using various chromatographic methods, three new compounds, (7S,8R,8′R)‐9,9′‐epoxy‐3,5,3′,5′‐tetramethoxylignan‐4,4′,7‐triol ( 1 ), 8α‐hydroxyoplop‐11(12)‐en‐14‐one ( 5 ), and (1R,2S,4S)‐4‐acetyl‐2‐[(E)‐(cinnamoyloxy)]‐1‐methylcyclohexan‐1‐ol ( 12 ) along with twelve known compounds were isolated from the leaves of P. vietnamensis. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for the inhibitory activities of nitric oxide production in LPS‐stimulated BV2 cells. As the results, compound 6 showed the most potent inhibitory activity on LPS‐stimulated NO production in BV2 cells with the IC₅₀ values of 15.7 ± 1.2 μm . Compounds 2 , 7 , and 8 significantly inhibited inflammatory NO production with IC₅₀ values ranging from 22.6 to 25.3 μm .     

Two New Ergosterol Derivatives from the Basidiomycete Cortinarius glaucopus

Two new sterols 1 and 2 and five known ones 3 – 7 were isolated for the first time from the fruiting bodies of Cortinarius glaucopus. Their structures were established by 1‐ and 2D‐NMR spectra and HR‐FABS‐MS. The relative configuration of 1 was firmly determined by comparison of the observed ¹H–¹H couplings and NOESY correlations, with those predicted for the computed geometries of the conformers. Calculations were performed by means of DFT with the B3LYP functional at 6‐31 + G(d,p) level of theory, in CHCl₃ as the solvent. The structures of the new ergosterol derivatives, called glaucoposterol A ( 1 ) and B ( 2 ), were thus established as (3S,5R,7R,10R,13R,17R,20S,22R,23R,24R)‐5,6‐epoxy‐3,7,23‐trihydroxystrophast‐8‐en‐14‐one and (22E,3S,5S,9S,10R,13R,17R,20R,24R)‐3,5‐dihydroxyergosta‐6,8(14),22‐trien‐15‐one, respectively. Moreover, the configuration of known strophasterol C ( 3 ) was determined as (3S,5R,6S,7R,10R,13R,17R,20S,22S,24R). Glaucoposterol A ( 1 ) and strophasterol C ( 3 ) represent the second finding in nature of steroids with the rare strophastane skeleton.     

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.     

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.     

The absolute configuration of the acetylenic compound falcarindiol

The absolute configuration of the acetylenic compound falcarindiol is established as (3R,8S) and falcarindiol is thus (+)-(3R,8S)-(Z)-heptadeca-1,9-dien-4,6-diyn-3,8-diol. (R)-Heptadecan-8-ol and (S)-heptadecan-8- ol are synthesized and (3R,8S)-heptadecan-3,8-diol is characterized.     

Sterol Chemotaxonomy of Marine Pelagophyte Algae

Several marine algae of the class Pelagophyceae produce the unusual marine sterol 24‐propylidenecholesterol, mainly as the (24E)‐isomer. The (24Z)‐isomer had previously been considered as a specific biomarker for Aureococcus anophagefferens, the ‘brown tide’ alga of the Northeast coast of the USA. To test this hypothesis and to generate chemotaxonomic information, the sterol compositions of 42 strains of pelagophyte algae including 17 strains of Aureococcus anophagefferens were determined by GC analysis. A more comprehensive sterol analysis by HPLC and ¹H‐NMR was obtained for 17 selected pelagophyte strains. All strains analyzed contained 24‐propylidenecholesterol. In all strains belonging to the order Sarcinochrysidales, this sterol was found only as the (E)‐isomer, while all strains in the order Pelagomonadales contained the (Z)‐isomer, either alone or together with the (E)‐isomer. The occurrence of Δ²² and 24α‐sterols was limited to the Sarcinochrysidales. The first occurrence of Δ²²‐24‐propylcholesterol in an alga, CCMP 1410, was reported. Traces of the rare sterol 26,26‐dimethyl‐24‐methylenecholesterol were detected in Aureococcus anophagefferens, and the (25R)‐configuration was proposed, based on biosynthetic considerations. Traces of a novel sterol, 24‐propylidenecholesta‐5,25‐dien‐3β‐ol, were detected in several species.     

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.     

Production of Cephalosporin Antibiotics by Strains Belonging to the Genera Arachnomyces,Anixiopsis and Spiroidium

The absolute configuration of a phytoalexin “Safynol” (3E, 11E)-3, 11-tridecadiene-5, 7, 9-triyne-l, 2-diol (I), separated from Phytophthora drechsleri-infected safflower (Carthamus tinctorius L.) was confirmed. (R) and (S)-safynol were synthesized from 2, 3-O-isopropyli- dene-(S)- and (R)-glyceraldehyde respectively, and the (R) configuration was assigned to the natural product. The inhibitory effects of (R)- and (S)-safynol on mycelial growth of five fungi were almost the same and their ED₅₀ values ranged from 6 to 70 ppm.