Search

Chemical investigation on CH 2 Cl 2 extract of the marine sponge Leucetta chagosensis , collected from the South China Sea, afforded two new 5,6-epoxysterols, 5α,6α-epoxycholesta-8(14),22( E )-diene-3 β ,7 α -diol ( 1 ) and (24 R )-24-ethyl-5α,6α-epoxycholesta-8(14),22( E )-diene-3 β ,7 α -diol ( 2 ) along with ten known related steroid analogs ( 3 - 12 ). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparison with the literature. All isolates were tested for cytotoxicity against three tumor cell lines only known compounds 11 and 12 exhibited notable cytotoxic activity against A549 (IC 50 : 3.0 and 5.6 μM), PC9 (2.0 and 15.6 μM), and MCF-7 (9.4 and 11.8 μM) cell lines, respectively.

Phytochemical research of Perilla frutescens aerial parts led to isolation of 12 secondary metabolites, including one new 3-benzoxepin glucoside, perillafrutoside A (1), one new megastigmane glycoside, perillafrutoside B (2), and 10 known compounds. Their chemical structures were identified based on 1D/2D NMR, HRESIMS, and ECD spectroscopic analyses. The structure of 2 was elucidated based on revision of the previously reported stereoisomer, (6R,9R)-blumenyl α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside. Evaluation of their antimicrobial effect revealed that compounds 1 and 5–11 inhibit Enterococcus faecalis growth, compounds 6, 7 and 9 suppress Staphylococcus aureus growth, whereas compounds 6 and 11 attenuate Candida albicans growth. This is the first report of the isolation of 3–5, 8–10 and 12 from the genus Perilla and the antimicrobial effect of compounds 3, 8 and 10. [ABSTRACT FROM AUTHOR]

A new cyclopentenone derivative, 4-hydroxyhypocrenone A, and a new naturally-occurring wickerol derivative, 8-acetoxywickerol A, as well as two known compounds, hypocrenone A and wickerol B, were purified from Trichoderma atroviride A-YMD-9-4, an endophytic fungus isolated from the marine red alga Gracilaria verrucosa. The structures and relative configurations of two new isolates were established by a combination of 1 D/2D NMR, IR, and mass spectroscopic methods, and the absolute configuration of 1 was assigned on the basis of ECD data analyzed by quantum chemical calculations. Compounds 1 and 2 exhibited weak inhibition of one or two marine phytoplankton species. [ABSTRACT FROM AUTHOR]

Four sesquiterpenoids A-D (1–4) were isolated from the ethanol extracts of the leaves and stems from Schisandra chinensis. Their structures and absolute configurations were elucidated by a combination of NMR, MS and ECD. Compounds 1–4 (10 μM) exhibited moderate hepatoprotective activities against APAP-induced LO2 cell damage with increasing cell viability by 18%, 17%, 16%, and 19% compared to the model group (bicyclol, 26%) at 10 μM, respectively. All the compounds displayed no cytotoxic activity against five human cell lines, which also suggested the safety of leaves and stems of S. chinensis as an edible vegetable in a degree. [ABSTRACT FROM AUTHOR]

Four new aaptamine alkaloids, named as 9-methoxy-N-demethylaaptanone (1), 3,5-dicarbomethoxy-1,​6-​naphthyridine (2), aaptosvanphongs A and B (3 and 4), and three known aaptamine alkaloids as 2-methoxy-3-oxoaaptamine (5), 8,9,9-trimethoxy-9H-benzo[de][1,6]-naphthyridine (6), and demethyl(oxy)aaptamine (7) were isolated from the sponge Aaptos by various chromatographic methods. Their structures were established by extensive spectroscopic analyses (HR-ESI-MS, 1 D and 2 D NMR) and by comparison of the spectral data with those reported in the literature. Compounds 1-7 significantly showed cytotoxic effects against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values in range from 7.7 ± 0.8 to 51.4 ± 1.8 µM. Among them, compound 7 exhibited the most cytotoxic activity with corresponding IC50 values of 9.2 ± 1.0, 7.8 ± 0.6, 8.4 ± 0.8, and 7.7 ± 0.8 µM. [ABSTRACT FROM AUTHOR]

Sargentodoxa cuneata (Oliv.) Rehd. et Wils is a traditional Chinese medicine to treat acute appendicitis, rheumarthritis, abdominal pain, and painful menstruation for a long history. The investigation of S. cuneata led to the isolation and identification of twenty-three secondary metabolites, including two new compounds, sargentodoxosides A (1) and B (2), and twenty-one known ones (3-23). Their structural characterization was conducted by HRESIMS, 1 D and 2 D NMR spectra. All the isolated compounds were assayed for their agonistic activities against the farnesoid X receptor (FXR). Nine of the isolated compounds displayed significant agonistic effects against FXR at 0.1 µM, suggesting that they could be served as potential agents for the development of FXR agonists. [ABSTRACT FROM AUTHOR]

From the EtOAc-soluble extract of the stems of Buchanania lucida, one new lignan, (+)-(8S,8′S)-5′-methoxy-4,4′-di-O-methylsecoisolariciresinol (1), together with five known compounds (2–6) were isolated. Their structures were elucidated on the basis of NMR spectroscopic interpretation. The absolute configuration of 1 was determined based on the Cotton effects in the ECD spectrum. In the tyrosinase inhibitory activity test, p-hydroxybenzoic acid (6) showed the strong effect, with an IC50 value of 9.35 µM. [ABSTRACT FROM AUTHOR]

A new diketopiperazine, cyclo-(d-8-acetoxyl-Pro-l-Leu) (1), together with eight known compounds (2–9) including three enterotoxins (2–4), four diketopiperazines (5–8) and maltol (9), were isolated from the mangrove derived-soil Streptomyces sp. SCSIO 41400. The planar structures of all compounds were determined from analysis of NMR spectra, MS, optical rotation and comparing with literature data. The absolute configuration of compound 1 was assigned by electronic circular dichroism (ECD). The isolated compounds (1–9) were tested for their acetyl cholinesterase (AChE) and pancreatic lipase (PL) enzyme inhibitory activities. Among them, the new diketopiperazine (1) displayed preferable PL enzyme inhibitory activity with IC50 value of 27.3 μg/mL, while compounds 2, 5 and 6 showed weak PL enzyme inhibitory activity. Further molecular docking simulation exhibited that compound 1 could be well bind with the catalytic pocket of the PL. Besides, compound 9 showed moderate antibacterial activity against Methicillin-resistant Staphylococcus aureus with MIC value of 12.5 μg/mL, which was comparable to that of the positive control ampicillin with MIC value of 3.125 μg/mL. [ABSTRACT FROM AUTHOR]

Synsepalum dulcifificum is an evergreen shrub native of tropical West Africa. It is very effective against a variety of diseases. However, the phytochemical investigation on this plant is limited till now. In our current study, seventeen compounds were isolated and identified from the ethyl acetate extract of the leaves. All of the compounds were obtained from S. dulcifificum for the first time. Compounds 4 and 9 were isolated from natural source for the second time. Moreover, the antioxidant activities of compounds 1, 4, 5, 9-11, and 15 were evaluated firstly. Compounds 6, 7, 13, and 14 exhibited significant antioxidant activity in DPPH and ABTS + assays, suggesting their potential application for an antioxidant drug. [ABSTRACT FROM AUTHOR]

A new alkaloid polygonatine C (3-(2'-furaldehyde-5'-methoxymethyl)5,6,7,8 -tetrahydroindolizin-8-one, 1) and a new saponin huangjingsterol B (3-β-hydroxyspirost-5,25-diene-12-one, 2), together with three known compounds 3–5 were isolated from the ethanolic extract of the Stewed Polygonatum cyrtonema Hua. The structures of these new compounds were identified by extensive spectroscopic analysis including 1D and 2D NMR and MS, as well as chemical methods. The new compounds were tested for their Protective effect against Aβ25-35 induced cytotoxicity and oxidative stress damage in PC12 cells. The results indicated that compounds 1–2 can be considered as promising lead compounds for further research on Alzheimer's disease (AD) treatment. [ABSTRACT FROM AUTHOR]

Three new cyclopentenoneacrylic acid derivatives, trichodermacid A (1), trichodermester A (2), and trichodermester B (3), together with thirteen known compounds, were isolated from an ethyl acetate extract of Trichoderma atroviride H548, a fungus derived from mangrove sediment. The structures of the new compounds were elucidated by spectroscopic methods including HR ESI-MS, 1H NMR, 13C NMR, and 2D-NMR techniques. The antifungal activity of the isolated compounds was evaluated against tea pathogenic fungus Pestalotiopsis theae. Trichodermester A (2) showed potent anti P. theae activity with MIC of 125 μg/disc, while the other compounds were inactive. [ABSTRACT FROM AUTHOR]

The investigation of chemical constituents from the leaves and seeds of Vitex negundo var. heterophylla resulted in the isolation of one new phenolic glycoside, vitexnegheteroin M (1), together with eleven known compounds (2-12). Their structures were elucidated through extensive spectroscopic analyses including 1D, 2D NMR, HR-ESI-MS, and by comparison with the literature. Among them, compound 3 was obtained from the Vitex genus for the first time, and compounds 4-8, and 10-12 were isolated from this plant for the first time. Their anti-inflammatory activities were investigated by measuring nitric oxide (NO) production in lipopolysaccharide (LPS)-induced murine microglial BV-2 cells. As the obtained results, compound 9 showed the strongest inhibitory activity against LPS-stimulated NO production in BV-2 cells with IC50 value ranging from 8.65 ± 0.67 μM. [ABSTRACT FROM AUTHOR]

Chemical investigation of the twigs of Cryptocarya impressinervia yielded 23 known compounds including 8 lignans, 3 phenylpropionates, 1 xanthone, 3 flavonoids, 1 phenylpropanoid, 1 substitued phenol, 1 triterpenoid, 3 sterols and 2 aliphatic compounds. All the compounds was isolated from C. impressinervia for the first time. 9,9'-O-Di-feruloyl-(-)-secoisolariciresinol (1) displayed significant cytotoxic activities on five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), with IC50 values of 3.58, 4.55, 6.39, 5.09 and 4.80 μM, respectively. Rhusemialin A (2) showed significant activity against HL-60 with IC50 of 3.69 μM. Dihydrosinapyl ferulate (3) displayed moderate cytotoxic activities against five tested human cancer cell lines. To the best of our knowledge, this is the first report on the constituents of C. impressinervia and cytotoxic activities of compounds 1-3 on the tested cancer cell lines. [ABSTRACT FROM AUTHOR]

Four new C-geranyl flavonoids, paulownione D-G (1–4) were isolated from the 50% acetone-H2O extract of the flowers of Paulownia fortunei. The structures of the compounds were determined by extensive spectroscopic analyses (UV, IR, HR-ESI-MS, 1D and 2D NMR). All of the compounds (1–4) exhibited potent protection effects in H9c2 cardiocytes against the lipopolysaccharide (LPS)-induced inflammation. [ABSTRACT FROM AUTHOR]

One new sesqui-neolignan compound, namely, sesqui-illisimonan A (1), one new neolignan, illisimonan A (2), and one new phenylpropanoid compound, illisimoid A (3) were isolated from the fruits of Illicium simonsii Maxim. The structures and absolute configurations of these compounds were determined by extensive spectroscopic, including NMR, circular dichroism and calculated electronic circular dichroism methods. The antioxidant activities of compounds 1-3 were also evaluated. Vitamin E was selected as the positive control (IC50 = 49.73 ± 0.88 μM). Compounds 1 and 2 exhibited in vitro antioxidant activity with an IC50 value of 55.76 ± 1.30 and 59.36 ± 0.50 μM, respectively. However, the compound 3 didn’t show obvious antioxidant activity. [ABSTRACT FROM AUTHOR]

A new sesquiterpene kalinturoside A (1), and 17 known compounds friedelan-3-ol (2), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (3), friedelin (4), syringaresinol (5), α-spinasterol (6), ciwujiatone (7), syringic acid (8), scopoletin (9), apocynin (10), 1-(3-hydroxy-4, 5-dimethoxyphenyl)ethan-1-one (11), apigenin (12), 5-hydroxymethylfurfural (13), stigmasterol-3-O-β-d-glucopy-ranoside (14), bidenoside C (15), citrusin (16), irioresinol A (17) and syringaresinol-4-O-β-d-glucopyranoside (18) were isolated from the herbs of Kalimeris integrifolia. The structures of these compounds were elucidated using spectroscopic techniques such as NMR and MS. All of the compounds were isolated from this genus for the first time. [ABSTRACT FROM AUTHOR]

A new seco-neolignan glycoside, seco-dehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside (1), together with eight known compounds, were obtained from the EtOH extract of the root bark of Ailanthus altissima. Their structures were elucidated based on the spectroscopic data. Three neolignan glycosides including 7,9,9′-trihydroxy-3,3′,5′-trimethoxy-8-O-4′-neolignan-4-O-β-D-glucopyranoside (5), sonchifolignan B (6) and citrusin B (7) exhibited moderate in vitro inhibitory effect on tobacco mosaic virus replication with IC50 values 0.30, 0.35 and 0.26 mmol L−1, respectively. [ABSTRACT FROM PUBLISHER]