New triterpenoid saponins from the leaves of Cyclocarya paliurus

Two new secodammarane triterpenoid saponins, cyclocariosides I and J (1 and 2), and a new epoxydammarane triterpenoid saponin, cyclocarioside K (3) were isolated from the ethanol extracts of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic techniques.     

Tetracyclic triterpenoids from the leaves of Azadirachta indica and their insecticidal activities

A new tetranortriterpenoid, meliatetraolenone [24,25,26,27-tetranor-apotirucalla-(apoeupha)-6alpha-O-methyl, 7alpha-senecioyl(7-deacetyl)-11alpha,12alpha,21,23-tetrahydroxy-21,23-epoxy-2,14,20(22)-trien-1,16-dione] (1) was isolated from the methanolic extract of fresh leaves of Azadirachta indica along with the known compound odoratone (3) which was hitherto unreported from this source. Their structures have been elucidated by spectral studies including 2D NMR. The insecticidal activities of 1 as well as those of odoratone (3) are reported. 1 and odoratone both showed mortality on fourth instar larvae of mosquitoes (Anopheles stephensi) with LC(50) values of 16 and 154 ppm, respectively.     

Diterpenoids from the gum resin of Boswellia carterii and their biological activities

Seven new diterpenoids, classified as three cembrane-type diterpenoids boscartins I-K (1–3) and four prenylaromadendrane-type diterpenoids boscartols K-N (4–7), respectively, along with nine known diterpenoids, were isolated from the gum resin of Boswellia carterii. Their structure elucidations were achieved by spectroscopic examination. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production and antiproliferative activity against MCF-7 human breast cancer cell in vitro. 4 and 5 exhibited potent inhibitory effects on NO production (IC₅₀ of 2.22 and 1.10?μM, respectively), with 11 showing moderate inhibition (IC₅₀ of 8.63?μM), and 12 and 15 demonstrated moderate antiproliferative effects against MCF-7?cell (IC₅₀ of 9.5, and 6.3?μM, respectively).     

Prenylated sulfonyl amides from the leaves of Glycosmis pentaphylla and their potential anti-proliferative and anti-inflammatory activities

Six previously undescribed sulfur-containing amides were isolated from the leaves of Glycosmis pentaphylla. Their structures were delineated by HRESIMS, 1D and 2D NMR, electronic circular dichroism (ECD) calculations, and DP4+ analyses based on gauge-independent atomic orbital (GIAO) NMR calculations. Compounds 1–4 belong to the type of methylsulfonylpropenoic acid amides. Through different cyclization pathways of geranyloxy, compounds 1 and 2 carry uncommon cyclohexane-1, 3-diol and cyclohex-3-en-1-ol moiety, respectively. Compound 3 is the oxidation product of the double bond Δ^{6′′(7′′)} of geranyloxy. Compound 5 is elucidated as the type of methylsulfonylpropanoic acid amide. Compound 6 represents a rare sulfur-containing amide possessing a morpholin-3-one moiety. All isolated compounds were evaluated for their anti-inflammatory and anti-proliferative activities. Compound 4 significantly inhibited lipopolysaccharide-induced nitric oxide (NO) production in mouse macrophage RAW 264.7 cells with the IC₅₀ value of 0.55 µM. Moreover, compounds 3 and 4 exhibited different anti-proliferative activities against HepG-2 with IC₅₀ values ??of 11.52 and 9.41 µM, respectively.     

New isolates from leaves of Nicotiana tabacum and their biological activities

Three new isolates (1?3) including one new sterol and two new flavonoids together with three known sterols (4?6) were isolated from the leaves of Nicotiana tabacum. Their structures were determined mainly by spectroscopic methods, including extensive 1D and 2D NMR techniques. All compounds were evaluated for their anti-tobacco mosaic virus and cytotoxic activities. The results showed that compounds 2 and 3 exhibited high anti-TMV activity with inhibition rate of 34.2 and 33.4%, respectively, which were roughly equivalent to that of positive control. The cytotoxicities of compounds 1 and 4–6 against five human tumour cell lines were also tested, and tested compounds showed weak inhibitory activities against some tested human tumour cell lines.     

Saussurea costus for sustainable and eco-friendly synthesis of palladium nanoparticles and their biological activities

Palladium nanoparticles have been evaluated as a viable candidate in the realm of biological applications due to their unique features. Saussurea costus extract was used as a stabilizing and reducing agent for the synthesis of palladium nanoparticles with average grain size of 17.6 ± 1.2 nm. The synthesized PdNPs were evaluated for their antioxidant activity, anti Alzheimer's activity, antibacterial and anticancer activities. The nanocharacterization was carried out using different spectroscopic techniques, including UV–visible spectroscopy, Transmission Electron Microscopy, Fourier Transformed Infrared spectroscopy, X-ray Diffraction analysis, X-ray Photoelectron spectroscopy, Energy Dispersive X-ray Spectroscopy, Size distribution, and Zeta potential. The characterization data explained the PdNPs mediated by S.costus extract have spherical form and are disseminated without agglomeration. FTIR and XPS supported the hypotheisis that the biomolecules of S.costus are activing as a reducing and stabilizing agents. The antioxidant activity of PdNPs was assessed using a free radical scavenging assay (DPPH) which exhibited similar results to the ABTS assay i.e. 90 μg/mL IC₅₀ value. Moreover Alzheimer's disease can easily be inhibited by S.costus@PdNPs at 400 mg/mL, with 79.23 ± 1.11 % of inhibition rate against AChE and 76.13 ± 0.43 % towards BChE. S.costus@PdNPs showed comparatively greater antibacterial activity against all four Staphylococcus aureus, Bacillus subtilis Escherichia coli and Pseudomonas aeruginosa microorganisms. Supplementary research carried out on the anti-tumor effects of the generated PdNPs using the colon cancer (HCT-116), hepatocellular carcinoma (HepG2), and breast adenocarcinoma (MCF-7) cell lines. PdNPs showed potent anticancerous activity against all the cell lines. Thus we recommend S.costus@PdNPs as a thearapeutic agent after successful clinical trails in future.     

Structural,functional, molecular,and biological evaluation of novel triterpenoids isolated from Helichrysum stoechas (L.) Moench. Collected from Mediterranean Sea bank: Misurata- Libya

Helichrysum stoechas (L.) Moench (Family Compositae) is a medicinal herb endowed with several pharmacological activities. Ethanolic extract of the aerial parts of the plant was used for the isolation of lignoceric acid (HS-02), lanost-5- en-3β-ol- 26-oic acid (HS-03), and lanost-5-en-26-oic acid-3β-olyl palmitate (HS-04). All molecules were screened for anti-inflammatory and analgesic activities at 5 and 10 mg/kg body weight doses, and the TEST program assessed their toxicity. The molecular interaction profile with numerous anti-inflammatory drug targets was investigated by molecular docking. Compounds HS-03 and HS-04 showed a significant reduction in paw volume compared to the control group challenged with carrageenan in the rats, and prolongation of the paw licking/jumping and reduction in the number of writhes was noted after the injection of acetic acid in mice. In a hot plate test, all compounds showed significant pain inhibition. These findings might aid in the development of anti-inflammatory and anti-analgesic therapies.     

Two new cycloartanes from the leaves of Combretum quadrangulare growing in Vietnam and their biological activities

Two new cycloartanes, combretanones G and H (1 and 2), were isolated from the leaves of Combretum quadrangulare. Their structures were elucidated by applying a set of spectroscopic methods, while their relative configurations were determined using DFT-NMR chemical shift calculations and subsequent assignment of DP4 probabilities. Compounds 1 and 2 are C-23/C-24 stereoisomers of the previously-reported euphonerin E. Both exhibited moderate cytotoxicity against three human cancer cell lines. Compound 2 was shown to be a potent antiparasitic. Our results confirm the traditional medicinal uses of Combretum quadrangulare in Vietnam.     

Arylnaphthalide lignans from Saussurea medusa and their anti-inflammatory activities

Five new arylnaphthalide lignans (1 ? 4a/4b), together with five known analogues (5–9), were isolated from whole plants of Saussurea medusa. Compound 4 was characterized as an aryltetralin lignan with an unusual C-7′-C-9 oxygen bridge group, and a chiral HPLC analysis was carried out to afford one pair of enantiomers (4a/4b). Structures of the new compounds were elucidated by extensive spectroscopic and electronic circular dichroism (ECD) calculations. All compounds were firstly isolated from S. medusa, and compounds 1–5, 7 and 8 had never been obtained from the genus Saussurea previously. Furthermore, this is the first report of arylnaphthalide lignans isolated from S. medusa. anti-inflammatory activities of the compounds were evaluated by determining their inhibitory activities on the production of NO by LPS-stimulated RAW 264.7 cells. Compounds (?)-4a and 5 exerted the significant inhibition activities with IC₅₀ values of 13.4 ± 1.5 and 15.7 ± 1.1 μM, respectively, which even exceeded the positive control quercetin (IC₅₀ = 15.9 ± 1.2 μM). Compounds 2, (+)-4b, 6 and 9 exhibited moderate inhibitory activities with IC₅₀ values ranging from 19.7 ± 1.9 to 47.4 ± 3.1 μM. Further analysis by molecular docking showed that almost all the active compounds could interact with the amino acid residues of iNOS proteins, which also supported their anti-inflammatory activities.     

New triterpenoids from the leaves of Abrus precatorius

Three new (1-3) triterpenoids and one known (4) triterpenoid were isolated from an acid hydrolyzed methanol-soluble extract of the leaves of Abrus precatorius. Their structures were identified as (20S,22S)-3beta,22-dihydroxycucurbita-5(10),24-diene-26,29-dioic acid delta-lactone (1), 3-O-[6'-methyl-beta-D-glucuronopyranosyl]-3beta,22beta-dihydroxyolean-12-en-29-oic acid methyl ester (2), 3-O-beta-D-glucuronopyranosylsophoradiol methyl ester (3), and sophoradiol (4) by spectroscopic techniques including 2D NMR.     

Diterpenoids from Isodon species and their biological activities

Isodon species (Labiatae) are widely distributed plants, many of which are used in folk medicine. Over the past twenty years, they have received considerable phytochemical and biological attention. Thestructures of their many diterpenoids constituents, especially those with an ent-kaurane skeleton, have been elucidated. The significant phytochemical and pharmacological diterpenoids form the subject of this review. There are 290 references.     

A new diarylheptanoid and a new diarylheptanoid glycoside isolated from the roots of Juglans mandshurica and their anti-inflammatory activities

A new diarylheptanoid, (2S,3S,5S)-2,3,5-trihydroxy-1,7-bis(4-hydroxy- 3-methoxyphenyl)heptane (1), and a new diarylheptanoid glycoside, (2S,3S,5S)-2,3-dihydroxy-5-O-β-d-xylopyranosyl-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptane (2), together with three known compounds, rhoiptelol C (3), rhoiptelol B (4) and 3′,4″-epoxy-2-O-β-d-glucopyanosyl-1-(4-hydroxyphenyl)- 7-(3-methoxyphenyl)heptan-3-one (5) were isolated from the roots of Juglans mandshurica (Juglandaceae). The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Compounds 1–5 were assayed for their inhibitory effects on the production of NO, TNF-α and IL-6 in LPS-stimulated RAW264.7 cells.     

Secolignans, neolignans and phenylpropanoids from Daphne feddei and their biological activities

Two new secolignans and one new neolignan, named feddeiphenols A-C (1-3), together with eight known compounds (4-11), were isolated from the leaves and stems of Daphne feddei. Their structures were established on the base of spectroscopic methods, mainly extensive NMR, UV spectroscopy, and MS spectrometry. Compounds 1-11 were tested for their anti-human immunodeficiency virus (HIV)-1 activity and cytotoxicity. The results revealed that compounds 1, 2, 3, 7, and 9 showed therapeutic index (TI) values above 30, respectively, and the other compounds also showed weak anti-HIV-1 activity. Compound 1 showed modest cytotoxic activity. The other compounds also showed weak cytotoxic activity.     

Iridoids from the roots of Valeriana jatamansi and their biological activities

A new iridoid, jatamandoid A (1), and four known analogues (2-5) were isolated from the roots of Valeriana jatamansi. Their structures were elucidated on the basis of extensive spectroscopic analysis (IR, ESI-MS, HR-ESI-MS, 1-D and 2-D NMR). Five compounds were evaluated and compounds 1, 2 and 5 showed moderate neuroprotective effects against MPP(+)-induced neuronal SH-SY5Y cell death.     

Antibacterial triterpenoids from the leaves of Ilex hainanensis Merr.

One new triterpenoid (1) and seven known analogues (2–8) were isolated from the leaves of Ilex hainanensis Merr.. Their structures were established by analysis of their MS, 1D and 2D NMR spectroscopic data and comparison with those in the literature. The antibacterial activity of compounds 1–8 were evaluated by determination of minimum inhibitory concentration using twofold microdilution broth method against Streptococcus mutans ATCC 25175 (Gram-positive) and Fusobacterium nucleatum ATCC 10953 (Gram-negative). Compounds 3 and 5 showed significant antibacterial activity against S. mutans in concentration of 9.7 μg/mL, while showed little antibacterial activity against F. nucleatum. On the contrary, the inhibitory activity of compounds 1, 2 and 6 against F. nucleatum were higher than them against S. mutans.     

Sesquiterpenoids from Curcuma wenyujin dreg and their biological activities

Four new sesquiterpenoids,4,8-dioxo-6β-hydroxyl-7β,1 1-epoxycarabrane(1),4,8-dioxo-6β-hydroxyl-7,1 1-epoxycarabrane(2),wenyujinins Q and R(3-4),and nine known sesquiterpenoids(5-13) were isolated from the Curcuma wenyujin(C wenyujin) dreg.Their structures and relative configurations were elucidated using 1D,2D NMR,and HR-ESI-MS data.All the compounds were isolated for the first time from the C.wenyujin dreg and evaluated for their antibacterial and antifungal activities.Compounds 3,5-8 exhibited strong broad-spectrum antifungal activities against tested nine pathogenic fungi.     

Enzyme pretreatment improves the recovery of bioactive phytochemicals from sweet basil (Ocimum basilicum L.) leaves and their hydrodistilled residue by-products,and potentiates their biological activities

In the present study, the effect of enzyme pretreatment on essential oil recoveries from sweet basil (Ocimum basilicum L.) leaves was evaluated. Moreover, the consideration on the use of hydrodistilled residue by-products as a source of bioactive phytochemicals with antioxidant, antimicrobial, and repellent effects against the stored-grain pest Tribolium castaneum was examined. Results showed that the enzymatic pretreatment increased the extraction yield of essential oil by 400, 417, and 478% in hemicellulase-, cellulase-, and viscozyme-treated samples, respectively. Phenylpropanoids including methyl cinnamate, methyl eugenol, eugenol and estragol were found as the main components, and were particularly abundant in cellulase-treated samples. From the hydrodistilled residue of enzyme-treated samples, better recoveries of total phenols (TPC) (258.3–470.9 mg GAE/g extract) and flavonoids (TFC) (59.4–94.3 mg QE/g extract) were observed. Using the DPPH, ABTS, and FRAP assays, a strong antioxidant activity of the rosmarinic-rich extract was observed. Such an activity which was mediated through electron transfer mechanism was highly correlated with the TPC, TFC and rosmarinic acid content. The in vitro bioassay showed that methanol extract (6.29 and 12.58 µL/cm²) had repellent activity against the stored-grain pest Tribolium castaneum. These results suggest the potential of enzyme pretreatment to promote the use of hydrodistilled residue by-products as a valuable source of natural antioxidants and repellents ingredients.     

Efficient synthesis,reactions, and biological activities of new thieno and furopyrazolo[3,4-b]pyrazines and their related heterocycles

In the present investigation, a simple and straightforward methodology for the preparation of novel bifunctional thienopyrazolopyrazines 4a–d has been reported. Synthesis of thieno or furopyrazolopyrazines 5a , b , e , f was achieved by the reaction of o-amino-esters 4a , b , e , f with 2,5-dimethoxytetrahydrofuran. The latter pyrrolyl derivatives 5a , b , e , f were used as starting intermediates for the synthesis of new pyrimido, pyrido, and pyrazino heterocycles fused to the thieno or furopyrazolopyrazine moiety. Furthermore, alkaline hydrolysis of the o-amino-ester 4a followed by acidification afforded the corresponding o-amino carboxylic acid 15 , which was used as a versatile precursor for the synthesis of other heterocyclic compounds fused to the thienopyrazolopyrazine ring system, namely: pyrimidine, oxazine, oxazepine, and pyridine derivatives 16–23 . The chemical structures of the synthesized compounds were confirmed on the basis of elemental and spectral analyses (Fourier-transform infrared spectroscopy [FT-IR], ¹H nuclear magnetic resonance [NMR], and mass spectroscopy [MS] in addition to ¹³C NMR for some of them). Moreover, from the biological screening, we found that most of the tested compounds exhibited promising antifungal, antibacterial, and anti-inflammatory activities compared with the corresponding reference drugs.     

Flavonoids from the leaves of Epimedium Koreanum Nakai and their potential cytotoxic activities

Abstract

Phytochemical studies on the leaves of Epimedium koreanum Nakai have resulted in the discovery of two new flavonol glycosides, koreanoside F (1) and koreanoside G (2), along with six known flavonoids. Their structures were elucidated on the basis of HRESIMS, UV, IR, 1?D NMR and 2?D NMR data. Absolute configurations of 1 and 2 was further determined by ¹³C-NMR spectra with gate decoupling (GD). All of the compounds were evaluated for cytotoxic activities by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazoliumbromide (MTT) assay. The results indicated that compounds 3, 5, 6, 7 and 8 inhibited the proliferation of A549 and NCI-292 cells with IC₅₀ values of 5.7–23.5?μM. Real-time monitoring in three kinds of lung cancer cells and a kind of human bronchial epithelial cells treated with compound 6 was also assessed.