New polycyclic polyprenylated acylphloroglucinols with antidepressant activities from Hypericum perforatum L.

Six new polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperidiones A-F (1-6), were obtained from Hypericum perforatum L. Their structures were characterized via extensive spectroscopic analyses, the circular dichroism data of the in situ formed [Mo2(OCOCH3)4] complexes, the nuclear magnetic resonance calculation with DP4 + probability analysis, and the calculated electronic circular dichroism (ECD) spectra. Compounds 1-6 are bicyclic polyprenylated acylphloroglucinols with a major bicyclo[3.3.1]nonane-2,4,9-trione skeleton. Notably, compound 1 is a rare PPAP with a hydroperoxy group, and a plausible biosynthetic pathway for 1 was proposed. Compounds 4 and 6 exhibited significant neuroprotective effects under 10 µM against corticosterone (CORT)-injured SH-SY5Y cells. Furthermore, compound 4 demonstrated a noteworthy antidepressant effect at the dose of 5 mg/kg in the tail suspension test (TST) of mice, which was equivalent to 5 mg/kg of fluoxetine. And it potentially exerted an antidepressant effect through the hypothalamic-pituitary-adrenal (HPA) axis.

Isolation and structural identification of insecticidal compounds from Tripterygium wilfordii.

Five compounds were identified from Tripterygium wilfordii, including two novel compounds and three previously known compounds. Two newly discovered compounds are celangulin CY (1α,2α,3ß,4ß,6ß,8α,13-hepacetoxy-9ß-benzoyloxy-ß-dihydroagarofuran) and celangulin CQ (1α-nicotinoyloxy-2α,3ß,6ß-triacetoxy-9ß-furancarbonyloxy-13-isobutanoyloxy-4ß-hydroxy-ß-dihydroagarofuran). Their structures were determined using nuclear magnetic resonance (NMR), mass spectrometry (MS), and high-pressure liquid chromatography (HPLC). The isolated compounds were tested for insecticidal activity against the third instar larvae of Spodoptera frugiperda. Both celangulin CY and celangulin CQ exhibited significantly higher oral toxicity in the larvae than that exhibited by the three known compounds.

Secoiridoid dimers and their biogenetic precursors from the fruits of Cornus officinalis with potential therapeutic effects on type 2 diabetes.

Cornusdiridoid A-F (1-6), six unusual cornuside-morroniside secoiridoid dimers, and their possible new biogenetic precursor, 3″,5″-dehydroxycornuside (7), together with four known secoiridoids (8-11), were obtained from the fruits of Cornus officinalis. Their structures were elucidated on the basis of various spectroscopic and chemical methods. A plausible biosynthetic pathway of compounds 1-11 was proposed. The α-glucosidase inhibitory, antioxidant and anti-inflammatory activities of these isolates were evaluated. Some of them emerged out as potent antidiabetic, anti-inflammatory and free radical scavenging agents. Molecular docking was also carried out for antidiabetic target α-glucosidase to investigate the possible binding modes of the most potent α-glucosidase inhibitor, vincosamide (9). These results revealed that the secoiridoids from C. officinalis fruits may be served as new potential antidiabetic agents to prevent and treat type 2 diabetes.

Unusual cadinane-type sesquiterpene glycosides with α-glucosidase inhibitory activities from the fruit of Cornus officinalis Sieb. et Zuuc.

Five novel and rare cadinane-type sesquiterpene glycosides, cornucadinoside A-E (1-5) were isolated from water extract of the fruit of Cornus officinalis Sieb. et Zuuc.. The new chemical structures, together with their absolute configurations, were elucidated on the basis of extensive spectroscopic analysis, including a comparison of their experimental and calculated electronic circular dichroism (ECD) spectra. Their structures, which possess a naphthalene skeleton, are the first report on the occurrence of cadinane sesquiterpene glycosides in Cornus. Additionally, all the compounds exhibited marked α-glucosidase inhibitory activity except for 3in vitro.

[A new phenylpropanoid glycoside from fruit of Cornus officinalis].

To investigate the chemical compounds from the ripe fruit of Cornus officinalis, a new phenylpropanoid glycoside 1-O-(6'-O-p-hydroxybenzoyl-ß-D-glucopyranosyl)-p-phenylpropanol, named cornuphenylpropanoid A (1), were separated and purified by D101 macroporous resin, silica gel and ODS column chromatography. Its structure was extensively determined on basis of ¹H-NMR, ¹³C-NMR, DEPT, HSQC, HMBC and HR-ESI-MS spectroscopic data.

Cornusides A-O, Bioactive Iridoid Glucoside Dimers from the Fruit of Cornus officinalis.

Fifteen new and rare iridoid glucoside dimers, cornusides A-O (1-15), and 10 known iridoid glucosides (16-25) were isolated from the fruit of Cornus officinalis. These new chemical structures were established through spectroscopic analysis (UV, IR, HRESIMS, 1D and 2D NMR). Compounds 1-25 were tested for their inhibitory activities by measuring IL-6-induced STAT3 promoter activity in HepG2 cells, and 3, 12, 17, 22, and 23 showed inhibitory effects, with IC50 values of 11.9, 12.2, 14.0, 7.0, and 6.9 µM, respectively.

[Chemical constituents from ripe fruit of Cornus officinalis].

To investigate the chemical compounds from the fruit of Cornus officinalis, six compounds were isolated and determined by extensive spectroscopic analysis as 6'-O-acetyl-7α-O-ethyl morroniside (1), (-)-isolariciresinol 3α-O-ß-D-glucopyranoside(2), apigenin (3), cirsiumaldehyde(4), p-coumaric acid (5), caffeic acid (6). Compound 1 was a new iridoid glucoside,and compounds 2-4 were obtained from the Cornus genus for the first time. Compounds 2-6 were evaluated for the viability of PC12 cells when exposed in conditions of oxygen and glucose deprivation. The MTT results showed that compound 4 increased cell viability moderately in OGD/R treated PC12 cells at the concentration of 1.0 µmol•L⁻¹.

Three new diterpenoids from the roots of Euphorbia fischeriana and their cytotoxicity.

Euphorbiabietane F (1), a novel abietane diterpenoid with the unprecedented 6/6/5/6/5 carbon skeleton, one new strobane diterpenoid (2), together with one new pimarane diterpenoid (3) were isolated from the roots of Euphorbia fischeriana. The structures were elucidated by the extensive spectroscopic data, gauge-independent atomic orbital (GIAO) NMR calculations, the comparison of experimental and calculated ECD spectra, as well as single crystal X-ray diffraction. The cytotoxicity result suggested the moderate inhibition rate of 1 on the cell lines of HepG2 and A549.

Hypericin: A natural anthraquinone as promising therapeutic agent.

BACKGROUND: Hypericin is a prominent secondary metabolite mainly existing in genus Hypericum. It has become a research focus for a quiet long time owing to its extensively pharmacological activities especially the anti-cancer, anti-bacterial, anti-viral and neuroprotective effects. This review concentrated on summarizing and analyzing the existing studies of hypericin in a comprehensive perspective. METHODS: The literature with desired information about hypericin published after 2010 was gained from electronic databases including PubMed, SciFinder, Science Direct, Web of Science, China National Knowledge Infrastructure databases and Wan Fang DATA. RESULTS: According to extensive preclinical and clinical studies conducted on the hypericin, an organized and comprehensive summary of the natural and artificial sources, strategies for improving the bioactivities, pharmacological activities, drug combination of hypericin was presented to explore the future therapeutic potential of this active compound. CONCLUSIONS: Overall, this review offered a theoretical guidance for the follow-up research of hypericin. However, the pharmacological mechanisms, pharmacokinetics and structure activity relationship of hypericin should be further studied in future research.

Hyperforin: A natural lead compound with multiple pharmacological activities.

Hypericum perforatum L. (Clusiaceae), commonly known as St. John's wort, has a rich historical background as one of the oldest and most widely studied herbal medicines. Hyperforin is the main antidepressant active ingredient of St. John's wort. In recent years, hyperforin has attached increasing attention due to its multiple pharmacological activities. In this review, the information on hyperforin was systematically summarized. Hyperforin is considered to be a lead compound with diverse pharmacological activities including anti-depression, anti-tumor, anti-dementia, anti-diabetes and others. It can be obtained by extraction and synthesis. Further pharmacological studies and more precise detection methods will help develop a value for hyperforin. In addition, structural modification and pharmaceutical preparation technology will be beneficial to promoting the research progress of hyperforin based innovative drugs. Although these works are full of known and unknown challenges, researchers are still expected to make hyperforin play a greater value.

An unusual racemic C12-norabietane diterpene and a new abietane diterpene alkaloid from Salvia miltiorrhiza Bunge.

A rare C12-norabietane diterpene racemate (1) and a new abietane diterpene alkaloid (2) were isolated from the roots of Salvia miltiorrhiza Bunge. Their structures were established by comprehensive spectroscopic analyses, and 1 was successfully resolved by chiral HPLC, demonstrating that 1 is racemic. The absolute configurations of 1a [(+)-miltiorolide A], 1b [(-)-miltiorolide A], and 2 were determined using TDDFT-ECD calculations. 1a and 1b are the first examples of enantiomeric C12-norabietane diterpenes featuring an isobutylene with a tetrahydronaphthalene-butyrolactone ring system. The cytotoxic activities of the isolates (1 and 2) were evaluated against three human cancer cell lines BEL-7402, HT-29 and PANC-28. A plausible biogenetic pathway of 1 was also proposed.