Band 76, Heft 1-2

Chlorophyll (Chl) is a natural compound that is found in all autotrophic plants. Since phytophagous insects ingest the photosynthetically active material with the plant leaves, the question arises if and how herbivores deal with Chl and its degradation products. Here we review findings on Chl degradation in phytophagous insects and highlight the role of these ubiquitous plant metabolites for plant-feeding insects. Due to the anaerobic gut of many insects, the degradation is limited to the removal of the peripheral substituents, while the tetrapyrrole core remains intact. Proteins, such as red fluorescent protein, P252 (a novel 252-kDa protein), and chlorophyllide binding protein have been reported to occur in the insect gut and might be indirectly connected to Chl degradation. Besides of an nutritional value, e.g., by taking up Mg 2+ ions or by sequestration of carbon from the phytol side chain, the Chl degradation products may serve the insect, after binding to certain proteins, as antimicrobial, antifungal, and antiviral factors. The protein complexes may also confer protection against reactive oxygen species. The antibiotic potential of proteins and degradation products does not only benefit phytophagous insects but also human being in medical application of cancer treatment for instance. This review highlights these aspects from a molecular, biochemical, and ecological point of view.

Tissue factor (TF) which plays a key role in hemostasis and thrombosis appears to be an attractive target and medicinal plants having alkaloids inhibition TF activity benefit to cardiovascular disease (CVD). The aim of study is to explore further knowledge about alkaloids and TF. TF procoagulant activities were determined by the simplified chromogenic assay and their mRNA expression were then examined by reverse transcription and polymerase chain reaction. Besides, the potential of TF/FVIIa binding with four representative alkaloids were analyzed by molecular docking. The results indicated that these isoquinoline alkaloids with various structures had a different effect on suppression of TF activity. Molecular docking showed four alkaloids including l -corydalmine, berberine, jatrorrhizine, and tetrahydropalmatine were stably posed in the active binding pocket of TF/FVIIa. The SARs analysis showed the structural difference including planar, quaternary nitrogen, and the peripheral functional groups at C-8, C-9, C-10, have strong effect on inhibition of TF activity, which provided effective methods to modify isoquinoline alkaloids for inhibiting TF activity. This study provides a further evidence for the cardiovascular protection of isoquinoline alkaloids, and has physiological significance in the clinical challenge to use isoquinoline alkaloids or their potential analogs in the treatment of CVD.

Natural compound tetrandrine was reported to inhibit the proliferation of T cells by inhibiting activation of NF-κB. Chemically, isotetrandrine differs from tetrandrine only in the stereochemistry at the chiral centers. The present study aimed to compare their anti-proliferation effects on human T cells with a focus on NF-κB. The IC 50 values of tetrandrine against MOLT-4 cells, MOLT-4/DNR cells, and concanavalin A-activated peripheral blood mononuclear cells of healthy subjects and dialysis patients were 4.43 ± 0.22, 3.62 ± 0.22, 1.91 ± 0.22 and 3.03 ± 0.28 μM, respectively. Whereas, the IC 50 values of isotetrandrine against the above immune cells were 2.19 ± 0.27, 2.28 ± 0.33, 1.29 ± 0.14 and 1.55 ± 0.26 μM, respectively. The inhibitory effect of isotetrandrine against the proliferation of T cells was stronger than that of tetrandrine significantly ( p  < 0.05). Molecular mechanism investigation showed that 10 μM of isotetrandrine largely decreased the expression of p-NF-κB and NF-κB in both MOLT-4 and MOLT-4/DNR T cells ( p  < 0.05), whereas 10 μM of tetrandrine slightly inhibited the phosphorylation of p-NF-κB with little influence on the expression of NF-κB. Taken together, absolute configurations of tetrandrine and isotetrandrine are suggested to influence on their anti-proliferation effects in human T cells via different regulation of NF-κB.

Pulmonary arterial hypertension (PAH) is a group of diseases with an increase of pulmonary artery pressure (PAP) and pulmonary vascular resistance. Here, the effects of safflower injection, a preparation of Chinese herbs, was investigated in a monocrotaline (MCT)-induced PAH rat model. PAP, carotid artery pressure (CAP), and the right ventricular hypertrophy index (RVHI) increased in the PAH group, while safflower injection was able to inhibit this increase to similar levels as observed in the normal group. The arteriole wall of the lungs and cardiac muscle were thickened and edema was observed in the PAH group, while these pathologies were improved in the herb-treated group in a dose-dependent manner. MCT treatment induced proliferation of pulmonary artery smooth muscle cells (PASMCs), which was inhibited by safflower injection in a dose-dependent manner. Our experimental results demonstrated that safflower injection can regulate pulmonary arterial remodeling through affecting the expression of connective tissue growth factor, transforming growth factor-β, integrin, collagen or fibronectin, which subsequently affected the thicknesses of the arteriole walls of the lungs and cardiac muscle, and thereby benefits the control of PAH. This means safflower injection improved the abnormalities in PAP, CAP and RVHI, and pulmonary arterial remodeling through regulation of remodeling factors.

The objective of this study was to determine the chemical profile and to evaluate the antibacterial activity of the essential oils of Piper species and modulation of the antibiotic activity, using the microdilution method to determine the minimum inhibitory concentration. The chemical components were characterized by gas chromatography coupled to mass spectrometry, which revealed β-copaen-4-α-ol (31.38%), spathulenol (25.92%), and germacrene B (21.53%) as major constituents of the essential oils of Piper arboreum, Piper aduncum , and Piper gaudichaudianum , respectively. The essential oils analyzed in this study did not present a clinically relevant activity against standard and multiresistant Escherichia coli . However, in the case of multiresistant Staphylococcus aureus , there was a significant activity, corroborating with reports in the literature, where Gram-positive bacteria are more susceptible to antimicrobial activity. The essential oils modulated the effect of the antibiotics norfloxacin and gentamicin, having on the latter greater modulating effect; however, for erythromycin, no statistically significant effect was observed. In conclusion, the results obtained in this study demonstrated that the essential oils of the analyzed Piper species present an inhibitory effect against S. aureus and modulate antibiotic activity, most of which presents synergistic activity.

Eremurus persicus (Jaub. & Spach) Boiss. belonging to Xanthorrhoeaceae family is an endemic medicinal plant widely distributed in Iran. Its leaves have been traditionally used as a food and also as medicinal plant. Regarding the widespread application of E. persicus in Iranian folk medicine, and the insignificant investigation of its components, this study aimed at the isolation and identification of major secondary metabolites of this plant. By applying various chromatographic techniques, corchoionoside A ( 1 ), 4-amino-4-carboxychroman-2-one ( 2 ), isoorientin ( 3 ), ziganein 5-methyl ether ( 4 ), auraptene ( 5 ), and imperatorin ( 6 ) were isolated from the EtOAc and CHCl 3 fractions of the crude extract. Except isoorientin ( 3 ), all the identified phytoconstituents were reported for the first time from Eremurus genus.

From an EtOAc-soluble fraction of the stem barks of Swintonia floribunda (Anacardiaceae), decumbic anhydride ( 1 ) and four known compounds 2 – 5 were isolated. Their chemical structures were elucidated based on the spectroscopic data interpretation. The GIAO-DFT calculation of 13 C NMR chemical shifts was carried out to clarify the structure of 1 . The absolute configuration of 1 was assigned based on the Cotton effects in its ECD spectrum. Compound 1 showed potent tyrosinase inhibitory activity with an IC 50 value of 52.2 μM.

Various Achillea species are rich in bioactive compounds and are important medicinal plants in phytotherapy. In the present study, Achillea millefolium L., Achillea moschata Wulfen, and Achillea atrata L. were compared with respect to their phenolic profile and antibacterial activity against gram-positive bacteria strains ( Staphylococcus, Propionibacterium ). Particular focus was given to A. atrata , which has hardly been studied so far. Based on the metabolite profile, A. atrata exhibited more similarities to A. moschata than to A. millefolium . The former two only differed in the occurrence of four compounds. The flavonols syringetin-3- O -glucoside and mearnsetin-hexoside, not reported for an Achillea species before, have been detected in A. atrata and A. moschata . All Achillea species reduced growth of the tested bacteria. A. atrata demonstrated highest activity against Propionibacterium acnes and Staphylococcus epidermidis , both being involved in the pathogenesis of acne vulgaris. Furthermore, A. atrata has a pronounced anti–methicillin-resistant Staphylococcus aureus potential. Bioassay-guided fractionation revealed that only the most polar fraction of A. moschata displayed antimicrobial activity, which was attributed to phenolics such as apigenin, centaureidin, and nevadensin, being present in high amounts in A. atrata . Thus, this alpine species shows promising antimicrobial activity and might be a potential source for developing novel dermal/topical drugs.

For seven days of wheat growth, caryopsis remained the main source of 5- n- alkylresorcinols with C19 and/or C21 homolog as a main compound. Shoot contained small amount of these phenolic lipids; their average content was 3.23% of level obtained in the whole seedling. Moreover, 41.38% of resorcinolic lipids of seven-day-old shoot was accumulated in part of leaf covered by coleoptile. Interestingly, a removal of 1.07% of the primary pool of kernel alkylresorcinols by short-term washing (10 s) of wheat seed with acetone before planting decreased their level only in seed of seven-day old seedling. Compared to the respective controls, this treatment did not affect the amount of these lipids in the green part of seedling that proved that de novo synthesis of 5- n- alkylresorcinols takes place in shoots. The very similar homolog profiles of these lipids in four- and seven-day-old shoots turned out to be markedly less diversified than those found in respective seed samples. Compared to the mature wheat caryopsis, the rise in the content of very-long-chain homologs was observed only in the oldest shoot. Their increased accumulation was probably connected with formation of cuticular layer providing the defensive barrier against various phytopathogens.

The Aerva plants are exceptionally rich in phytochemicals and possess therapeutics potential. Phytochemical screening shows that Aerva persica (Burm.f.) Merr. contains highest contents i.e. , total phenolics, flavonoids, flavonols, tannins, alkaloids, carbohydrates, anthraquinones and glycosides. In-vitro antibacterial and enzymatic (carbonic anhydrase) inhibition studies on methanol extracts of A. persica indicated the presence of biological active constituents within chloroform soluble portions. Investigation in the pure constituents on the chloroform portions of A. persica accomplished by column chromatography, NMR and MS analysis. The bioguided isolation yields four chemical constituents of coumaronochromone family, namely aervin ( 1 - 4 ). These pure chemical entities ( 1-4 ) showed significant antibacterial activity in the range of 60.05–79.21 µg/ml against various bacterial strains using ampicillin and ciprofloxacin as standard drugs. The compounds 1-4 showed promising carbonic anhydrase inhibition with IC 50 values of 19.01, 18.24, 18.65 and 12.92 µM, respectively, using standard inhibitor acetazolamide. First-principles calculations revealed comprehensive intramolecular charge transfer in the studied compounds 1-4 . The spatial distribution of highest occupied and lowest unoccupied molecular orbitals, ionization potential, molecular electrostatic potential and Hirshfeld analysis revealed that these coumaronochromone compounds would be proficient biological active compounds. These pure constituents may be used as a new pharmacophore to treat leaukomia, epilepsy, glaucoma and cystic fibrosis.

Cistus x incanus L. is a Mediterranean evergreen shrub used in folk medicine for the treatment of inflammatory disorders but the underlying mechanisms are not fully understood. We therefore investigated the anti-inflammatory effects of an ethyl acetate fraction (EAF) from C. x incanus L. leaves on lipopolysaccharide (LPS) activated RAW 264.7 macrophages. HPLC analysis revealed myricetin and quercetin derivatives to be the major compounds in EAF; EAF up to 1 µM of total phenolic content, was not cytotoxic and inhibited the mRNA expression of interleukin-6 (IL-6) and cyclooxygenase-2 (COX-2) ( p  < 0.05) and the production of prostaglandins E 2 (PGE 2 ) ( p  < 0.05). Meanwhile, EAF triggered the mRNA expression of interleukin-10 (IL-10) and elicited the nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2), as well as the expression of its main target gene, heme oxygenase-1 (HO-1) ( p  < 0.05). These data indicate that EAF attenuates experimental inflammation via the inhibition of proinflammatory mediators and at least in part, by the activation of Nrf2/HO-1 pathway. These effects are likely due to myricetin and quercetin derivatives but the role of other, less abundant components cannot be excluded. Further studies to confirm the relevance of our findings in animal models and to highlight the relative contribution of each component to the anti-inflammatory activity of EAF should be conducted.

A phytochemical investigation of the stem bark of Calophyllum canum resulted in the isolation of a new xanthone dimer identified as biscaloxanthone ( 1 ), together with four compounds; trapezifoliaxanthone ( 2 ), trapezifolixanthone A ( 3 ), taraxerone ( 4 ) and taraxerol ( 5 ). The structures of these compounds were determined via spectroscopic methods of IR, UV, MS and NMR (1D and 2D). The cytotoxicity of compounds 1–3 were screened against A549, MCF-7, C33A and 3T3L1 cell lines, wherein weak cytotoxic activities were observed (IC 50  > 50 μ m ).