Records of Natural Products Articles

Two new monoterpenes, 4 ² -hydroxy-3 ² -methoxyalbiflorin (1) and 6 ¢ -O-p-hydroxybenzoyl-4 ² -hydroxyalbiflorin (2), together with six known monoterpenes, which were albiflorin (3), oxypaeoniflorin (4), paeoniflorin (5), paeonins A (6), paeonins B (7) and benzoylpaeoniflorin (8) respectively, were isolated from the root material of Paeonia sinjiangensis. The compounds were identified by spectral analysis and comparison with spectroscopic data reported in the literatures. When the in vitro anti-hepatitis B virus (HBV) activities of compounds 1-8 were evaluated, all the isolated monoterpenes, except 6, reduced the yield of HBV DNA, suppressed HBsAg and HBeAg protein production from HepG2215 cell culture system, with compound 1 exhibiting the greatest potential.

 A novel series of 17-carboxylic acid modified amide derivatives of 3-hydroxy betulinic acid (1) were prepared and tested in vitro against five cell lines: A549 (human lung carcinoma), BEL-7402 (human hepatoma), SF-763 (human cerebroma), B16 (mice melanoma) and HL-60 (human leukaemia) . Within this series of compounds, 4a (IC 50=21.08 μ M in SF-763, IC 50=21.63 μ M in HL-60), 4b (IC 50=28.45 μ M in HL-60,IC 50=29.32 μ M in BEL-7402 ) and 6g (IC 50=26.09 μM in BEL-7402, IC 50=22.65 μM in HL-60) have the mo re potent cytotoxic activity than lead compound 1. The preliminary structure-activity relationship analysis of the C-28 amide derivatives is also discussed.

With regard to world’s increasing demand for biologically active compounds, a novel source of xanthones and secoiridoid glycosides has been studied . Zeltnera beyrichii (Torr. & A. Gray) Mans., an insufficiently acknowledged North American medicinal plant species, may be considered a pharmacological substitute for commercial C. erythraea Rafn, since it accumulates in aerial parts nearly the same amount of secoiridoid glycosides: swertiamarin, gentiopicrin, and sweroside (13.76, 7.56, and 0.17 mmol per 100 g dry weight, respectively) in plants grown under greenhouse condition, and a considerable amount of xanthones: decussatin and eustomin. Additionally, Z. beyrichii produced as much biomass during cultivation in RITA ® temporary immersion bioreactors as greenhouse-grown plants, in a third of the time. Plants grown in bioreactors contained moderate levels of total phenolics and total flavonoids, and possessed modest antioxidant activity and antimicrobial potential against eight bacterial and eight fungal species. Therefore, this species may be highly recommended for cultivation either in natural environment, or in bioreactors under in vitro conditions, for producing compounds of interest of modern pharmacology and food industry.

Plants of the Carex genus (Family: Cyperaceae) have attracted recent attention as potential food additives due to their high levels of potential bioactive compounds. In this study, the stilbene contents of five unexplored Carex species were investigated: Carex capillacea, Carex hirta, Carex buchananii, Carex cuprina, Carex glauca. High-performance liquid chromatography coupled to mass spectrometry (HPLC–MS) and NMR spectroscopy (NMR) were used to identify the structures. A novel stilbene oligomer, carexinol A, was isolated together with five previously known stilbenes: resveratrol-diglucoside, miyabenol A and C, kobophenol A and α-viniferin. Furthermore, this is the first report of resveratrol diglucoside in Carex genus.

A new c ycloheximide d erivative , Cycloheximide acid A (1) and two known compounds ( - )-anhydrocycloheximide (2), and l-cycloheximide (3 sp. Z00045 . The structure was determined on the basis of comprehensive 1D and 2D (COSY, HMQC, HMBC) NMR and MS analyses.

A trans cinnamic anhydride (1) isolated for the first time from a natural source, along with the known compounds: ferrulic acid (2), (E) p-hydroxy cinnamic acid (3), clovanediol (4), squalene (5), and α -bisabolene (6) were isolated from the stem bark of Cinnamomum zeylanicum. Their structures were elucidated by interpretation of NMR and MS data, and by comparison of these data with those reported in the literature. Their inhibitory properties were evaluated against Plasmodium falciparum enoyl-ACP reductase (PfENR) enzyme. Compounds 1 , 5 and 6 showed moderate inhibitory activity against P. falciparum enoyl-ACP reductase (PfENR) enzyme.

 A new triterpene ixorene (1) with dammarane skeleton was isolated from the leaves of Ixora coccinea, along with the three known constituents’ β-sitosterol (2), lupeol (3) and D-mannitol (4). The structure was elucidated on the basis of extensive 1D and 2D-NMR studies and mass spectrometry as 17β-dammara-12, 20-diene-3β-ol.

A new furanoisoflavone, 2 ' -methoxy-4 ' ,5 ' -methylenedioxy-[2 '' ,3 '' :7,8 ] furanoisoflavone, leptobotryanone ( 1 ) , and a new natural O-prenylated isoflavone, 4 ' -γ,γ-dimethylallyloxy-5,7-dihydroxyisoflavone ( 2 ) , were isolated from the twig s of Millettia leptobotrya, together with twelve known flavonoids, 4 ' -γ,γ-dimethylallyloxy-5-hydroxy-7-methoxyisoflavone ( 3 ), 2 ' ,6,7-trimethoxy-4 ' ,5 ' -methylenedioxy- isoflavone (4), 2 ' ,7-dimethoxy-4 ' ,5 ' -methylenedioxyisoflavone (5), maximaisoflavone B (6), medicarpin (7) , maackiain (8), genistein (9), biochanin A (10), prunetin (11), chrysoeriol (12) , kaempferol (13) and desmoxyphyllin A (14) The structures of new compounds were elucidated on the basis of spectroscopic data interpretation , including 1D and 2D NMR and HREIMS. Th is is the first phytochemical investigation of this plant.

In this study, phenolic content of Pinus brutia ’s bark was examined using an ultra-performance liquid chromatography tandem mass spectrometry with electrospray ionization source (UPLC-ESI-MS/MS) working in multiple reaction monitoring mode. U ltrasonic extraction method with 50% ethanol solution was used for the extraction of bark. The bark of Pinus brutia consisted of 15 compounds: gallic acid, gentisic acid, protocatechuic acid, 4-hydroxy benzoic acid, catechin hydrate, vanillic acid, caffeic acid, vanillin, p-coumaric acid, ferulic acid, myricetin, resveratrol, luteolin, naringenin, kaempferol. Major compound detected was catechin hydrate (28.305 mg 100 g -1 extract). The phenolic compounds of Pinus brutia extract and pycnogenol were compared, and it is shown that both of them consisted of considerable amount of phenolic compounds.

 Investigation of EtOAc extract from the fermentation broth of the endophytic fungus Asperilligus sp. HS-05 led to the isolation of a new compound (1) of spiro moiety named aspergispiroketal and seven known compounds (2-8). Their structures were elucidated mainly by NMR and HR-TOF-MS, as well as on comparison with the reported data. The absolute configuration of 1 was defined by comparison of quantum chemical TDDFT calculated and experimental ECD spectra.

 Phytochemical investigation of the aerial parts of Senecio desfontainei afforded one new benzoxepin derivative, Senecioside (1) along with eleven known compounds (2-12). Their structures were assigned from 1H and 13C NMR spectra, DEPT and by 2D COSY, NOE, HSQC and HMBC experiments. All these compounds were tested for antioxidant activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. Among them, compounds 2, 3, 4, 6 and 9 showed significant antioxidant activity against DPPH radicals.

 The essential oils from the aerial parts of ten wild growing Craniotome furcata (Link.) O. Kuntze of the family Lamiaceae collected from different locations in Uttarakhand, India, was analyzed by capillary GC and GC/MS. The oils were rich in sesquiterpenoids. The cluster analysis showed the presence of four groups. Group-I was significantly rich in δ-elemene and germacrene D while group-II had germacrene D in abundant quantity. α-Bisabolol oxide A, α-cadinol and germacrene D-4-ol were major constituents of group-III. Group-IV showed the presence of α-muurolol and germacrene D as major constituents. Germacrene D was found to be present in all the samples of C. furcata collected from different locations and was positively correlated with the altitude of the collection regions. Chemical variation in the volatiles was statistically correlated with altitude and soil properties.

Three new compounds, namely barceloneic lactone B (1) and barceloneic acid C (2) and 5’ -hydroxychlorflavonin ( 3 ), together with one known compound chlorflavonin ( 4 ), were isolated from the marine fungal strain Aspergillus sp. AF119. Their structures were elucidated by spectroscopic analyses including 1D- and 2D NMR experiments, and HR Q-TOF mass spectrometry. The antifungal activities against Candida albicans of these compounds were evaluated.

T wo new monoterpenes : ( (1S,2R,3R,5S)-2-hydroxymethyl-6,6-dimethylbicyclo[ 3.1.1]heptane-2,3-diol (1) and (3R)-6,6-dimethyl-4-methylenebicyclo[3.1.1]heptane-1,3-diol-3-O- b -D-glucopyranoside (2), along with three known compounds, namely, sobrerol (3), (1R,2S,5S)-2,8-p-menth-diol (4) and (lR,5S)-10-hydroxyverbenon (5), were isolated from aerial part of Tithonia diversifolia. Their structures were determined on the basis of spectroscopic analyses (IR, HR - ESI-MS/MS, 1D/2D NMR). Under the concentration of 10 m g/mL, compounds 1 and 3 significantly increased glucose uptake in 3T3-L1 adipocytes without significant toxic effects in vitro.

 Plectranthus is known for its medicinal value . The paper describes the antibacterial and cytotoxic activity of diterpenoids ent -7-hydroxykaur-15,16-en-19-oic acid (1), 17-oxokaur-15,16-en-19-oic acid (2) and ent-7-hydroxy-15,16-epoxykauran-19-oic acid (3), isolated from the shade-dried and powdered leaves of Indian Plactranthus coesta. Diterpenoid 3 was isolated for the first time from Indian P. coesta . Diterpenoid 1, shows potent activity against E. coli (15.6 µg/mL), P. aureginosa (17 µg/mL) and K. planticola (32.5 µg/mL), while diterpenoid 2, also showed good activity against E. coli (61 µg/mL), P. aureginosa (61 µg/mL), K. planticola (61 µg/mL) and S. epidermidis (125 µg/mL). Diterpenoids 1-3 were found to be more efficacious on U87 cancer cells and less toxic on normal human HEK and HeLa cells.

Two new phenolic compounds, P andanusphenol A (1) and B (2) , were obtained from the fruits of Pandanus tectorius . The ir structures including absolute configurations were determined by extensive spectroscopic analysis including 2D NMR experiments ( 1H- 1H COSY, HMBC , and NOESY ) and HRESIMS results as well as CD data . The substituted pattern of two methoxy group s on the phenyl ring of Pandanusphenol A (1) is rarely seen in natural furofuran lignans 

The study of the chemical constituents of the whole plant of Erigeron bonariensis (L.) has resulted in the isolation and characterization of a new and nine known compounds. The known compounds were identified as stigmasterol (1), freideline (2), 1, 3-dihydroxy-3R,5R-dicaffeoyloxy cyclohexane carboxylic acid methyl ester (3),1 R ,3R-dihydroxy-4S,5R-dicaffeoyloxycyclohexane carboxylic acid methyl ester (4), quercitrin (5), caffeic acid (6), 3-(3,4-dihydroxyphenyl)acrylic acid 1-(3,4-dihydroxyphenyl)-2-methoxycarbonylethyl ester (8), benzyl O-β-D-glucopyranoside (9), and 2-phenylethyl-β-D-glucopyranoside (10). The aromatic glycoside, erigoside G (7) is reported as new natural compound. The above compounds were individually identified by spectroscopic analyses and comparisons with reported data. The chemotaxonomic studies of isolated compounds have been discussed.