New lignans attenuating cognitive deterioration of Aβ transgenic flies discovered in Acorus tatarinowii

Five new lignan racemates, (±)-tatarinoid D–H (1–5), and three known analogues (6–8) were isolated from the rhizomes of Acorus tatarinowii. Their structures were established by 1D, 2D-NMR, HR-MS, IR and optical spectral data. Among them, 1 and 6–8 can alleviate the cognitive deterioration of Aβ transgenic flies.     

Evolvosides C–E,flavonol-4-O-triglycosides from Evolvulus alsinoides and their anti-stress activity

Phytochemical investigation of the n-butanol fraction of Evolvulus alsinoides (Linn.) led to the isolation of three new phenolic glycosides, evolvosides C, D and E (1–3) along with six known compounds (4–9). The structures of the compounds were elucidated on the basis of spectroscopic analysis, viz. 1D and 2D NMR experiments, chemical study, and comparison with literature data. Evolvoside C (1) was characterized as kaempferol 4′-O-β-d-glucopyranosyl-(1→2)-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside, whereas evolvosides D and E (2–3) were found to be mono and di-O-methyl derivatives of 1. The new compounds (1–3) represent rare triglycoside derivatives of flavonol at C-4′. The isolated compounds (1–6) were screened for acute stress-induced biochemical changes in male Sprague–Dawley rats at a dose of 40 mg/kg body weight. Compounds 1 and 2 displayed anti-stress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 3 and 6 were also found to be effective in normalizing most of these stress parameters, whereas compounds 4 and 5 were ineffective in normalizing most of these effects.     

Six kanshone C-derived sesquiterpenoid hybrids nardochalaristolones A–D,nardoflavaristolone A and dinardokanshone F from Nardostachys jatamansi DC.

Four sesquiterpenoid-chalcone hybrids (nardochalaristolones A–D, 1–4), a pair of epimeric sesquiterpenoid-flavonone hybrids ((2′S)- and (2′R)-nardoflavaristolone A, 5 and 6), and a sesquiterpenoid dimer (dinardokanshone F, 7), all sharing a kanshone C-derived sesquiterpenoid unit, were isolated from the underground parts of Nardostachys jatamansi (D.Don) DC. Their structures were elucidated by analysis of the extensive spectroscopic data, and the absolute configurations were established by analysis of 2D NMR spectroscopic data including NOESY data, combined with comparisons of experimental and calculated electronic circular dichroism spectra. Further, the plausible biosynthetic pathways for these compounds were proposed. And the results of SERT activity assay revealed that nardochalaristolones C–D (3 and 4) and nardoflavaristolone A (5 and 6) significantly enhanced SERT activity, while other compounds didn't show any SERT regulatory activities.     

Furan derivatives from Lannea kerstingii

Two new furan derivatives, lannefuran A (1) and lannefuran B (2) were isolated from the stem bark extract of Lannea kerstingii Engl. & K. Krause together with five known compounds, namely: taraxerol, stigmast-4-en-3-one, monoglyceride of hexacosanoic acid, β-sitosterol and its glucoside. Their structures were determined by means of 1D and 2D NMR, IR, and HR–EI–MS spectra and comparison with the data of known analogues reported in the literature. Lannefuran A (1) exhibited very low antiplasmodial activity against Plasmodium falciparum 3D7.     

Bioactive butylphthalide derivatives from Ligusticum chuanxiong

Seven new butylphthalide derivatives, ligusticumolide A-G (1–7), together with two known butylphthalide derivatives (8–9) were isolated from an ethanol extract of Ligusticum chuanxiong Hort. The structures of these derivatives were elucidated from analysis of 1D/2D NMR, UV, IR and HRESIMS data. The absolute configurations of these derivatives were determined by electronic circular dichroism (ECD) calculations and Mosher′s method. Ligusticumolide A (1) and ligusticumolide B (2) are enantiomers that were obtained by chiral separation. Ligusticumolide C (3) and ligusticumolide D (4) are diastereomers. All of the compounds were evaluated for their hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury. Compounds 4, 5, and 7–9 showed more significant hepatoprotective activity than that of the positive control drug (bicyclol) at a concentration of 10 μM (p < 0.01).     

A new flavone glycoside from the leaves of Agastache rugosa (Fisch. & C.A.Mey.) Kuntze

Agastache rugosa (Fisch. & C.A.Mey.) Kuntze has been widely used as a food spice and a remedy for colds in Korea, China and Japan. In this study, one new flavone glycoside (1) along with six flavonoids (2–7), nine phenyl glycosides (8–16) and three megastigmane glycosides (17–19) were isolated from the leaves of A. rugosa. By extensive spectroscopic methods including 1D and 2D NMR, and MS data, the structure of the new compound (1) was elucidated as acacetin 7-O-β-(6″-(E)-crotonylglucopyranoside). From present investigation, compound 1 and 7–19 were isolated for the first time from the genus Agastache and 1, 16, 18 and 19 in the Lamiaceae family.     

Secondary metabolites from the stem bark of Juglans mandshurica

A pair of new dibenz[cd,lm]perylene derivatives, juglanperylenone A (1a) and juglanperylenone B (1b), along with ten known compounds, including four anthraquinones (2–5), two coumarins (6–7) and four triterpenoids (8–11), were isolated from the stem bark of Juglans mandshurica Maxim. Their structures were elucidated on the basis of spectroscopic evidence, including 1D and 2D NMR, HR-TOF-MS, and by comparison with literature data. In addition, the chemotaxonomic significance of the isolates was also discussed in this paper.     

Caffeoylquinic acid derivatives from the roots of Arctium lappa L. (burdock) and their structure–activity relationships (SARs) of free radical scavenging activities

Eight caffeoylquinic acid (CQA) derivatives have been identified from the roots of Arctium lappa L. (burdock), including three new derivatives (1–3) together with five known derivatives (4–8). Their chemical structures were determined by 1D and 2D NMR as well as HR-TOF-MS data. The free radical scavenging activities of each compound were determined experimentally and found to be significant, especially the tri-CQA (8) and di-CQAs (6–7). Besides, our data showed that the number of caffeoyl groups in the caffeoyl derivatives played a crucial role for these physiological functions.     

Ulmosides A and B: Flavonoid 6-C-glycosides from Ulmus wallichiana,stimulating osteoblast differentiation assessed by alkaline phosphatase

Chemical investigation of Ulmus wallichiana stem bark resulted in isolation and identification of three new compounds (2S,3S)-(+)-3′,4′,5,7-tetrahydroxydihydroflavonol-6-C-β-d-glucopyranoside (1), (2S,3S)-(+)-4′,5,7-trihydroxydihydroflavonol-6-C-β-d-glucopyranoside (3) and 3-C-β-d-glucopyranoside-2,4,6-trihydroxymethylbenzoate (8), together with five known flavonoid-6-C-glucosides (2, 4–7). Their structures were elucidated using 1D and 2D NMR spectroscopic analysis. The absolute stereochemistry in compounds 1 and 3 were established with the help of CD data analysis and comparison with the literature data analysis. All the isolated compounds (1–8) were assessed for promoting the osteoblast differentiation using primary culture of rat osteoblast as an in vitro system. Compounds 1–3 and 5 significantly increased osteoblast differentiation as assessed by alkaline phosphatase activity.     

A 5-alkylresorcinol and three3,4-dihydroisocoumarins derived from Ononis natrix

Phytochemical investigation of Ononis natrix L. led to the isolation of an alkylresorcinol (1) and three alkyl isocoumarins (2–4) from the acetonitrile fraction of acetone extract of the aerial part of Ononis natrix. The structures of the compounds were determined by spectroscopic analyses including 1D, 2D NMR, MS, and comparison with literature data. All compounds (1–4) were evaluated for antimicrobial, antiprotozoal, antioxidant and cytotoxic activities. The compounds showed moderate antimicrobial and antiprotozoal activities.     

Lignan derivatives from Selaginella tamariscina and their nitric oxide inhibitory effects in LPS-stimulated RAW 264.7 cells

The chemical characterization of Selaginella tamariscina leaves resulted in the isolation of five lignanoside derivatives (1–4 and 6) and one neolignan (5). These compounds include three new lignanosides, tamariscinosides D–F (1–3), and one liriodendrin (4) that were isolated for the first time from this plant, together with two known compounds, (2R,3S)-dihydro-2-(3,5-dimethoxy-4-hydroxyphenyl)-7-methoxy-5-acetyl-benzofuran (5) and moellenoside B (6). The chemical structures of these isolated compounds were determined using 1D and 2D NMR, MS, and CD spectroscopic data, and the results were compared to data previously reported in the literatures. These compounds were also evaluated in terms of their inhibition of NO production in lipopolysaccharide (LPS)-stimulated activity in the macrophage cell line RAW 264.7. Among them, compounds 1, 2, 5, and 6 exhibited a significant inhibition with IC₅₀ values ranging from 32.3 to 55.8 μM.     

Phytochemical study of Capraria biflora L. aerial parts (Scrophulariaceae) from Martinique island (French West Indies)

Aerial parts of Capraria biflora L. were collected in Martinique (French West Indies) and extracted by methanol. Two original chlorinated iridoids, 3-hydroxymyopochlorin (1) and 5-hydroxyglutinoside (2) were isolated by CPC (centrifugal partition chromatography) and characterized from the extract together with five known iridoid glycosides (3–7), two flavonoid glucuronides (8–9) and the phenylethanoid glycoside verbascoside (10). The structure of these compounds together with their relative configuration was established by spectroscopic data including in particular 1D and 2D NMR experiments (HSQC, HMBC, NOESY) and HRESIMS. Preliminary antibacterial evaluation of 1, 2 and 3 against a panel of Gram-positive and Gram-negative strains has been performed.     

Oxirapentyns B–D produced by a marine sediment-derived fungus Isaria felina (DC.) Fr

Three new highly oxygenated chromene derivatives, oxirapentyns B–D (1–3) and one known oxirapentyn A (4) were isolated from the lipophilic extract of the marine-derived fungus Isaria felina KMM 4639. The structures of compounds 1–3 were determined based on spectroscopic methods. The absolute configuration of oxirapentyn B (1) as 2R, 4S, 5S, 6S, 7R, 8S, 9S was established by a combination of modified Mosher's method, X-ray analysis, and NOESY data. Oxirapentyn A (4) showed weak cytotoxicity against SK-Mel-5, SK-Mel-28 human malignant melanoma, and T-47D human breast cancer cell lines.     

Diarylpentanoids from Diplomorpha canescens and Diplomorpha ganpi

Two new α-hydroxy ketone type diarylpentanoids, diplomorphanone A, 2(S)-hydroxy-1-(4-hydroxyphenyl)-5-phenyl-1-pentanone (1) and diplomorphanone B, 2(R)-hydroxy-1,5-diphenyl-1-pentanone (2) were isolated from aerial parts of Diplomorpha canescens (Meisn.) C.A. Meyer and roots of Diplomorpha ganpi (Sieb. et Zucc.) Nakai, respectively. Nine known compounds including diarylpentanoids (3–6), phenylpropanoid derivatives (7–9), (+)-afzelechin (10) and apiosylskimmin (11) were also isolated for the first time from D. ganpi. Structures of these compounds were elucidated on the basis of spectroscopic data.     

Minutissamides E–L,antiproliferative cyclic lipodecapeptides from the cultured freshwater cyanobacterium cf. Anabaena sp.

The extract of UIC 10035, a strain obtained from a sample collected near the town of Homestead, South Florida, showed antiproliferative activity against MDA-MB-435 cells. Bioassay-guided fractionation led to the isolation of a series of cyclic lipodecapeptides, named minutissamides E–L (1–8). The planar structures were determined by analysis of HRESIMS, tandem MS, and 1D and 2D NMR data, and the stereoconfigurations were assigned by LC–MS analysis of the Marfey’s derivatives after acid hydrolysis. Minutissamides E–L (1–8) exhibited antiproliferative activity against MDA-MB-435 cells with IC₅₀ values ranging between 1 and 10 μM. The structures of minutissamides E–L (1–8) were closely related with those of the previously reported lipopeptides, puwainaphycins A–E and minutissamides A–D, characterized by the presence of a lipophilic β-amino acid and three non-standard amino acids NMeAsn, OMeThr and Dhb (α,β-dehydro-α-aminobutyric acid). The strain UIC 10035 was designated as cf. Anabaena sp. on the basis of morphological and 16S rRNA gene sequence analyses.     

Saponins from the rhizomes of Polygonatum nodosum Hua and their chemotaxonomic significance

Phytochemical investigation on the rhizomes of Polygonatum nodosum Hua resulted in the isolation of thirteen saponins, which could be subdivided into eleven spirostanol saponins (1–5, 7–11 and 13) and two triterpenoid saponins (6 and 12). Structure elucidation of these isolates was performed based on MS, CD, 1D and 2D NMR data. All compounds (1–13) were first reported from P. nodosumthis, and compound diosgenin 3-O-α-L-rhamnopyranosyl-(1→2)-[O-α-L-arabinofuranosyl-(1 → 4)]-β-D-glucopyranoside (7) was first reported from the family Asparagaceae. Moreover, the chemotaxonomic significance of isolates was detailedly introduced.     

Chemical constituents from the pericarps of Zanthoxylum bungeanum and their chemotaxonomic significance

The phytochemical study of the pericarps of Zanthoxylum bungeanum Maxim under the guidance of bioactivity led to the isolation of 18 compounds, including a new isobutylhydroxyamide (1) and 17 known compounds, i.e. six alkylamides (2–7), five coumarins (8–12), one benzene derivative (13), three flavonoids (14–16), and two sterols (17–18). Their structures were elucidated based on extensive spectroscopic methods (HRESIMS, 1D and 2D NMR experiments) and by comparison with literature data. New compound (1) and known compound (2) are cis-trans isomeric isobutylhydroxyamides. Among them, compounds 9, 10, and 12 were isolated for the first time from Z. bungeanum, compound 11 was firstly recovered from the genus Zanthoxylum, and compound 14 was reported for the first time from the Rutaceae family. The chemotaxonomic significance of isolated compounds from Z. bungeanum is discussed.     

New butenolide derivatives from the marine sponge-derived fungus Aspergillus terreus

Two new butenolide derivatives (±)-asperteretal D ((±)-1) and asperteretal E (2) containing rare 2-benzyl-3-phenyl substituted lactone core, together with nine known analogues (3–11) were obtained from a fungus Aspergillus terreus derived from the marine sponge Phakellia fusca. All the structures were elucidated on the basis of extensive NMR spectroscopic data. The chiral chromatography analyses allowed the separation of the (±)-asperteretal D, of which the absolute configurations were determined by comparing the experimental to calculated electronic circular dichroic (ECD) spectra. Compounds (±)-1, 2–5, and 7 exhibited potent inhibitory activities against α-glucosidase with IC₅₀ values ranging from 8.65 to 20.3?µM (positive control acarbose with an IC₅₀ value of 320?µM). In addition, derivatives 5–8 also showed moderate antioxidant activities.     

Chemical constituents from the roots of Zizyphus jujuba Mill. var. spinosa

One new flavonoid, named (R)-2-hydroxynaringenin (1), along with fifteen known compounds, including six flavonoids (2–7), six lignans (8–13), two phenolic glycosides (14–15) and one alkaloid (16) were isolated from the roots of Zizyphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chou. Their structures were established on the basis of spectroscopic evidence, including 1D and 2D NMR, circular dichroism (CD) curve analysis, and by comparison with literature data. Compounds 2, 3 and 8–16 were found in Z. jujuba Mill. var. spinosa for the first time, while compounds 8, 10 and 13–15 were new to the Rhamnaceae family. In addition, the chemotaxonomic significance of the isolates was discussed in this paper.     

Four new phenylpropanoid glycosides from Clausena dunniana var. robustaand their antiinflammatory activities

Four new phenylpropanoid glycosides, clausenaglycosides A–D (1–4), along with fourteen known compounds (5–18) were isolated from the leaves and twigs of Clausena dunniana var. robusta. The structures of the isolated compounds were determined by a combination of 1D and 2D NMR, MS, and CD spectroscopic data. The NF-κB inhibitory activity was evaluated in HeLa cells. Compound 17 displayed a moderate inhibition against NF-κB activation.