New chromone analog and pyrrole alkaloid produced by Penicillium sclerotiorum and their antibacterial activity.

A new chromone analog (1) and a new pyrrole alkaloid (2), together with four known compounds, were isolated from the endophytic fungus Penicillium sclerotiorum MPT-250 obtained from the stems of Taxus wallichiana var. chinensis (Pilger) Florin. The structural elucidation of these metabolites was performed by high-resolution mass spectrometry and NMR spectroscopy. Compounds 1 and 5 exhibited significant antibacterial activity against carbapenems-resistant Pseudomonas aeruginosa and multidrug-resistant Enterococcus faecium with an minimum inhibitory concentration (MIC) value of 3.13 µg/ml respectively.

Identification of a Novel Pyrrole Alkaloid from the Edible Mushroom Basidiomycetes-X (Echigoshirayukidake).

Three pyrrole alkaloid derivatives were isolated from the edible mushroom Basidiomycetes-X (Echigoshirayukidake) by water extraction followed by ethyl acetate fractionation. The chemical structures determined by MS and NMR were 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanoic acid (compound I), 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanamide (compound II), and 5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde (compound III). Compound I was found to be the major component, followed by compound II, and compound III was the minor component. The dry powder of Basidiomycetes-X contained approximately 825 µg g-1 compound I and 484 µg g-1 compound II. Compound II was found to be a novel pyrrole aldehyde homologue not previously reported and thus is a specific component of this mushroom.

Synthesis and biological evaluation of longanlactone analogues as neurotrophic agents.

Longanlactone analogues were synthesized using a route featuring Friedel-Crafts acylation, Sonogashira coupling and 1,3-dipolar cycloaddition reactions. Structure-activity relationships were investigated for neurotrophic activity. Compound 6 was found to have the most potent neurotrophic activity among all the synthesized analogues in Neuro2a cells as evidenced by a battery of in vitro/cell based assays for assessment of neurogenic and potential neurotrophic activity including neurite outgrowth assay and real time PCR for popular markers of augmented neurotrophic activity. Compound 6 might serve as a template for further development of highly effective neurotrophic molecules.

Pyrrolo[2,1-a]isoquinoline and pyrrole alkaloids from Sinomenium acutum.

Two pyrrolo[2,1-a]isoquinolines (1 and 2) and three pyrrole alkaloids (3-5), including three new ones, named sinopyrines A-C (1-3), were isolated from the 95% EtOH extract of the stems and rhizomes of Sinomenium acutum (Thumb.) Rehd. et Wils. The structures of the new compounds were elucidated on the basis of spectroscopic data. This is the first report of pyrrole-bearing natural compounds from the family Menispermaceae.

Chemical Constituents from the Stems of Tinospora sinensis and Their Bioactivity.

Fifty-seven compounds were purified from the stems of Tinospora sinensis, including three new compounds characterized as a lignan (1), a pyrrole alkaloid (11), and a benzenoid (17), respectively. Their structures were elucidated and established by various spectroscopic and spectrometric analytical methods. Among the isolates, fifteen compounds were examined for their anti-inflammatory potential in vitro. The results showed that several compounds displayed moderate inhibition of N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release.

Analgesic alkaloids from Urticae Fissae Herba.

Objective: To investigate the analgesic substances in the aerial part of Urtica fissa (Urticae Fissae Herba), commonly used for rheumatoid and rheumatism arthritis. Methods: The analgesic constituents were isolated with the active guidance of hot plate and acetic acid writhing models, and identified by comprehensive spectroscopic analysis. Results: Thirteen alkaloids (1-13), two lignans (14, 15), and three amides (16-18) were isolated from the active fractions. Among them, compound 1 was a new alkaloid, and compound 6 was a new natural product. The activity evaluation in vivo indicated that various pyrrole alkaloids (1, 3, 6, and 12) possessed significant analgesic activities, they could significantly inhibit the mice pain response induced by acetic acid and hot plate at the dosage of 2 mg/kg BW. Conclusion: The study revealed that the pyrrole alkaloids played important roles in the analgesic activities of Urticae Fissae Herba.

Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus.

A phytochemical investigation of the EtOH extract of the flowers of Lagerstroemia indica L. led to the isolation and characterization of a new pyrrole alkaloid, named lagerindicine (1), along with four known compounds (2-5). Their structures were elucidated by the detailed spectroscopic analysis and comparison with literature data, whereas the structure, in particularly, the absolute configuration (AC) of 1, was firmly determined by total synthesis. All the isolates were evaluated for their cytotoxic effects against human colon cancer cell (HCT-116), and compound 3 exhibited weak cytotoxicity with IC50 value of 28.4 µM.

Four new pyrrole alkaloids from the rhizomes of Amomum koenigii.

Four new pyrrole alkaloids, named amokoens A-D (1-4), together with three known compounds (5-7) were isolated from the rhizomes of Amomum koenigii. Their structures and absolute configurations were established by spectroscopic data, including 1D and 2D NMR, and the optical rotation calculations. All the isolates were evaluated for their effects on nitric oxide (NO) production in lipopolysaccharide-induced RAW264.7 macrophages. Compounds 1-7 inhibited NO production ranging from 27.1 to 82.4% at a concentration of 100 µM, and compounds 5 and 6 showed efficacious inhibitory activities with IC50 values of 42.2 and 69.3 µM, respectively.

A new pyrrole alkaloid from the roots of Cissampelos pareira.

Phytochemical investigation of the roots of Cissampelos pareira Linn. led to the isolation of one new pyrrole alkaloid, cissampeline (1), together with ten known alkaloids, (-)-curine (2), (-)-cyclanoline (3), (+)-tetrandrine (4), (+)-obaberine (5), (+)-obamegine (6), (-)-oblongine (7), (+)-homoaromoline (8), (-)-nor-N׳-chondrocurine (9), trans-N-feruloyltyramine (10) and (+)-coclaurine (11). Their structures were elucidated by extensive NMR and MS spectroscopic analyses. Interestingly, compound 1 represents the first example of pyrrole alkaloid found in the genus Cissampelos. Moreover, compounds 5-11 were isolated for the first time from this genus. Among them, compound 6 showed the highest anti-acetylcholinesterase activity with an IC50 value of 3.26 µM, whereas compound 8 displayed the most potent cytotoxicity against human colon cancer (HT29) cells with an IC50 value of 7.89 µM.

Four new compounds from Neoboletus magnificus.

Four new compounds, compounds 1, 2, 4, 6, along with two known compounds 3, 5, were isolated from the methanol extract of the fruiting body of Neoboletus magnificus. The structures of compounds were elucidated by HRMS and NMR spectroscopic methods. The in vitro anti-inflammatory activity of the isolated compounds was evaluated.

A new nucleoside and two new pyrrole alkaloid derivatives from Cordyceps militaris.

A new nucleoside, a new natural product nucleoside, and two new pyrrole alkaloids derivatives with eight known compounds were isolated from the fruiting body of Cordyceps militaris. The structures of the new compounds were elucidated through extensive analysis of spectroscopic data including 1D and 2D NMR, HRESIMS, IR and UV. All the isolated compounds were detected for their bioactivities against LPS-induced NO production in RAW 264.7 cells. Unfortunately, all the isolates have shown no obvious activity.

Analgesic alkaloids from Urticae Fissae Herba / 中草药·英文版

Objective: To investigate the analgesic substances in the aerial part of Urtica fissa (Urticae Fissae Herba), commonly used for rheumatoid and rheumatism arthritis. Methods: The analgesic constituents were isolated with the active guidance of hot plate and acetic acid writhing models, and identified by comprehensive spectroscopic analysis. Results: Thirteen alkaloids (1–13), two lignans (14, 15), and three amides (16–18) were isolated from the active fractions. Among them, compound 1 was a new alkaloid, and compound 6 was a new natural product. The activity evaluation in vivo indicated that various pyrrole alkaloids (1, 3, 6, and 12) possessed significant analgesic activities, they could significantly inhibit the mice pain response induced by acetic acid and hot plate at the dosage of 2 mg/kg BW. Conclusion: The study revealed that the pyrrole alkaloids played important roles in the analgesic activities of Urticae Fissae Herba.

A novel pyrrole alkaloid from the fruit peels of Strychnos nux-blanda.

A novel pyrrole alkaloid, strychnuxin (1), along with five known compounds (2-6) was isolated from the fruit peels of Strychnos nux-blanda. The structures of all the isolated compounds (1-6) were fully characterised using spectroscopic data, as well as comparison with the previous literature data. Moreover, all isolated compounds were assessed for their α-glucosidase and acetylcholinesterase inhibitory activities.

Identification of new pyrrole alkaloids from the fruits of Lycium chinense.

Three new minor pyrrole alkaloids, 3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]pentanedioic acid (1), (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-1-methoxy-1-oxobutanoic acid (2), and methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate (3) were isolated from the fruits of Lycium chinense Miller (Solanaceae), along with the known compound, methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(phenyl)propanoate (4). The structures of 1-4 were elucidated by analysis of their 1D- and 2D-NMR and HRMS data. The absolute configurations of 2-4, possessing a stereogenic center in each structure, were determined by comparison of their experimental electronic circular dichroism (ECD) with those of calculated ECD values.