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Objectives: The objective of this study was to ascertain the presence and correlations among eight important secondary metabolites viz. hypericin, pseudohypericin, emodin, hyperforin, rutin, hyperoside, quercetin and quercitrin in different organs of 17 in vitro cultured Hypericum species, along with H. tomentosum and H. tetrapterum hairy root cultures, and hairy root-derived transgenic plants of H. tomentosum., Methods: Samples were extracted and analysed by LC-MS. The LC-MS data were subjected to chemometric evaluations for metabolite profiling and correlating the phytochemical compositions in different samples., Key Findings: Hypericin, pseudohypericin and their proposed precursor emodin were detected in various levels in the leaves of eight Hypericum species. The highest content of hypericins and emodin was found in H. tetrapterum, which contains the studied secondary metabolites in all plant organs. A significant positive correlation between hypericins and emodin was observed both by principal component analysis (PCA) and multidimensional scaling (MDS), indicating the role of emodin as a possible precursor in the biosynthetic pathway of hypericins. Flavonoids were found in all tested plant organs except roots of H. pulchrum. The hairy roots lacked hypericin, pseudohypericin, emodin, hyperforin and rutin. However, the hairy root-derived transgenic plants showed a significant increase in flavonoids., Conclusions: This study broadens knowledge about the phytochemical composition of selected in vitro cultured Hypericum species, compared to that of hairy root cultures and hairy root-derived transgenic plants., (© 2017 Royal Pharmaceutical Society.)

Extracts of Chlorophora regia are frequently used in Ghana in traditional medicine. There is, however, no reported data on the chemical composition of the plant. Comprehensive phytochemical investigation of the stem bark of C. regia resulted in the isolation of three new prenylated 2-arylbenzofuran derivatives, regiafuran A-C (1-3), and one new prenylated flavonol (4), together with fifteen known compounds (5-19). Their structures were elucidated by combined spectroscopic analysis of their NMR and HRESI-MS(n) data. Compounds 1, 2, 5, 9 and 15 exhibited remarkable free radical scavenging properties with IC50 values of 1.9 μg/ml, 2.4 μg/ml, 2.2 μg/ml, 2.1 μg/ml and 1.8 μg/ml, respectively, compared to the standard trolox (IC50 1.1 μg/ml). The isolated compounds did not, however, show any anti-inflammatory potential when tested using a PGE2 (prostaglandin E2) competitive enzyme immunoassay., (Copyright © 2015 Elsevier B.V. All rights reserved.)

Phytochemical investigation of the stem bark extract of Anopyxis klaineana was carried out by various chromatographic techniques resulting in the isolation and characterization of three new tirucallane triterpenoids, namely 3,23-dioxotirucalla-7,24-dien-21-oic acid (1), 3,4-secotirucalla-23-oxo-4(28)7,24-trien-3,21-dioic acid (2) and 3,4-secotirucalla-4-hydroxy-23-oxo-7,24-diene-3,21-dioic acid-21-methyl ester (3), along with nine known compounds (4-12). The structural elucidation of the compounds was performed by means of high-resolution mass spectrometry (HRMS(n)), nuclear magnetic resonance (NMR), and by comparison to literature data. Although none of the isolated compounds showed antibacterial efficacy against selected environmental and clinically important pathogenic Gram-positive and -negative bacteria, they demonstrated moderate DPPH free radical scavenging properties. Furthermore, compounds 1 and 7 exhibited remarkable anti-inflammatory potential in a prostaglandin E2 (PGE2) competitive enzyme immunoassay with IC50 values of 3.63 μM and 10.23 μM, respectively., (Copyright © 2015 Elsevier B.V. All rights reserved.)

Bioassay guided fractionation of Hypericum riparium leaves extract has resulted in the isolation and characterization of three new compounds namely chipericumin E (1), hyperenone C (3), and hyperixanthone (5), together with twenty known compounds. Their structures were elucidated based on comprehensive interpretation of spectroscopic and spectrometric data. Compounds 1-4, and 6-8 displayed moderate antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and cytotoxic effects on the human gastric cell line BGC-823 with IC50 values ranging from 6.54 to 18.50μM., (Copyright © 2015 Elsevier B.V. All rights reserved.)

The first phytochemical investigation of Solandra grandiflora Sw. leaves using LC/MS resulted in the identification without isolation of eight known and one unknown compounds from the neutral and the alkaloidal fractions. Further chromatographic fractionation and isolation of both fractions using RP-HPLC resulted in the isolation of chlorogenic acid, neochlorogenic acid, protocatechuic acid, scopoletin and isoscopoletin from the neutral fraction. Moreover, a new tropinene glycoside identified as 3-O-β-D-glucosyl 6-tropinene, together with atropine, scopolamine and hyoscyamine were isolated from the alkaloidal fraction. The structures of all isolated compounds were established and confirmed by 1H-, 13C-NMR, COSY, HSQC & HMBC spectroscopy, while the exact masses were confirmed by HRESIMS. The cytotoxic activity of all isolates was evaluated against HepG-2, HCT-116, A-549 and MCF-7, and the obtained results suggested selective antiproliferative and cytotoxic effect. [ABSTRACT FROM AUTHOR]

Abstract Phytochemical studies of the seeds of the Cameroonian medicinal plant, Salacia staudtiana , resulted in the isolation and identification of five new cardenolides (1 – 5) as well as a new dihydro-β-agarofuran (9), along with eight known compounds. The structures of all compounds were elucidated by 1D/2D NMR, ESI-HRMS data and comparison with literature data. The relative configurations of the new compounds were defined by X-ray crystallography analysis, NOESY correlations and coupling constants. We evaluated their antibacterial efficacy against two commonly dispersed environmental strains of Escherichia coli and Bacillus subtilis , and two pathogenic strains of Staphylococcus aureus and Pseudomonas aeruginosa , compared to the standard antibiotics, streptomycin and gentamicin. Moreover, we assessed the antibacterial activity of the crude extract of the seeds in parallel to evaluate the plausible synergistic effects of the compounds in chemical defense of the seeds during germination and plant reproduction. The isolated compounds showed moderate antibacterial activities against the tested organisms. Compounds 1 and 3 and the crude extract exhibited distinct antibacterial activities against B. subtilis and S. aureus. The isolated compounds showed weak DPPH radical scavenging properties compared to the reference standard (Trolox). Our study lends evidence to the antibacterial chemical defense of S. staudtiana seeds by seed-borne compounds. Graphical abstract Unlabelled Image [ABSTRACT FROM AUTHOR]

Chemical investigation of the roots of Entandrophragma congoënse (Meliaceae) led to the isolation of two new 3,4- seco -tirucallane triterpenes, namely seco -tiaminic acids B and C ( 1 and 2 ) together with nine known compounds: 3,4-secotirucalla-21-formyl-23-oxo-4(28),7,24-trien-3-oic acid ( 3 ), methyl angolensate ( 4 ), molucensin N ( 5 ), molucensin O ( 6 ), piscidinol A ( 7 ), 7 α ,20( S )-dihydroxy-4,24(28)-ergostadien-3-one ( 8 ), 24-methylene-cholest-5-en-3 β ,7 α -diol ( 9 ), entilin A ( 10 ), and entilin B ( 11 ). Their structures were determined using extensive spectroscopic methods including 1D and 2D NMR, HRMS, and CD analyses; new results were compared to existing data in the literature. The two newly identified seco -tiaminic acids showed moderate antiplasmodial and cytotoxic activities against a chloroquine-sensitive strain of the malaria parasite ( Plasmodium falciparum NF54) and were cytotoxic toward an L6 rat skeletal myoblast cell line, respectively. [ABSTRACT FROM AUTHOR]

Six new flavanones ( 1 – 6 ), together with six known compounds were isolated from Erythrina livingstoniana . Their structures were elucidated on the basis of NMR data and HRMS n fragmentation pathway and by comparison with literature data. Compounds 5 , 7 and 8 showed remarkable DPPH free radical scavenging efficacies. The compounds, however, did not demonstrate an anti-inflammatory potential when tested using a PGE 2 (prostaglandin E2) competitive enzyme immunoassay. The plausible biosynthetic pathways of the isolated compounds are described. [ABSTRACT FROM AUTHOR]

The chemical study of Erythrina livingstoniana has led to the isolation of three new flavanones namely 5,7,3′-trihydroxy-4′-methoxy-5′-formylflavanone (erylivingstone A) ( 1 ), 5,7,3′-trihydroxy-5′-(2-hydroxy-3-methylbut-3-enyl)-4′-methoxyflavanone (erylivingstone B) ( 2 ) and 5,7,3′-trihydroxy-5′-(3-hydroxy-3-methyl- trans -but-1-enyl)-4′-methoxyflavanone (erylivingstone C) ( 3 ) together with three known compounds ( 4 – 6 ). Their structures were elucidated on the basis of NMR data, HRMS n fragmentation pathway and by comparison with literature data. We evaluated the antibacterial efficacies and free-radical scavenging potential of the isolated compounds ( 1 – 6 ). The typical environmental strains of Gram-positive Bacillus subtilis , Gram-negative Escherichia coli , as well as against the clinically important Staphylococcus aureus , Streptococcus pyogenes and E. coli (risk-group 2) were used for the antibacterial assay. Compounds 5 and 6 exhibited the most pronounced efficacy against tested environmental bacteria as well as against the pathogenic strain of E. coli . Compound 3 was also quite active against these three bacterial strains. The isolated compounds showed weak radical scavenging properties with compound 6 being the most active, followed by compounds 2 , 3 and 5 . [ABSTRACT FROM AUTHOR]

Tetrapleura tetraptera is a medicinal plant used in East and West Africa to treat inflammation and related diseases. From the stem bark of the plant, three previously undescribed flavan-3-ol derivatives named (2 R, 3 S)-3,3′,5′,7-tetrahydroxy-4′-methoxyflavane (1), (2 R, 3 S) -3′,5′,7-trihydroxy-4′-methoxyflavane-3- O -β-D-glucopyranoside (2), and (2 R, 3 S, 4 S) -3,3′,4,5′,7-pentahydroxy-4′-methoxyflavane (3) were isolated with three known analogues. The structural elucidation of the compounds was performed based on NMR spectroscopy and HRMS data analyses. The absolute configurations around the stereogenic carbons were determined using Circular Dichroism (ECD) and density functional theory (DFT) calculations. The cytotoxicity of the isolated compounds was tested using resazurin reduction assay. Compound 1 was moderately active against both recalcitrant leukemia cell lines with IC 50 values of 21.90 μM towards CCRF-CEM and 50.80 towards CEM/ADR5000. Similar level of activity was observed for compound 3 against CCRF-CEM cell line, IC 50 = 35.50 μM. All the tested compounds were not cytotoxic compared with the standard drug, doxorubicin, with IC 50 values of 0.0075 against CCRF-CEM and 24.30 μM against CEM/ADR5000. [Display omitted] [ABSTRACT FROM AUTHOR]

Two new tirucallane-type triterpenoids were isolated from the bark of Entandrophragma congoënse (Meliaceae) along with five known compounds gladoral A, bipendensin, 4-hydroxymethyl-3,5-dimethyldihydrofuran-2(3 H )-one, scopoletin and 5,7-dimethoxy-6-hydroxycoumarin. Their structures were elucidated by means of spectroscopic analyses including 1D and 2D-NMR spectroscopy, high resolution mass spectrometric data as well as the comparison of data with those reported in the literature. The tested compounds ( 1 – 4 ) displayed moderated antiplasmodial activity against erythrocytic stages of chloroquine-resistant Plasmodium falciparum strain NF54 and low cytotoxicity on L6 cell lines. All the isolated compounds are reported for the first time from the genus Entandrophragma. [ABSTRACT FROM AUTHOR]

Four new steroidal sapogenins, dracaenogenins C F (1 – 4), a new conjugated chalcone-stilbene, 3′′-methoxycochinchinenene H (5) together with eight known compounds namely, (25 S)-spirosta-1,4-dien-3-one (6), trans -resveratrol (7), 4,4′-dihydroxy-3′-methoxychalcone (8), N - trans -coumaroyltyramine (9), N - trans - p -coumaroyloctopamine (10), N - trans -feruloyloctopamine (11), 7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)- N 2 , N 3 - bis (4-hydroxyphenethyl)-6-methoxy-1,2-dihydronaphthalene-2,3-dicarboxamide (12) and grossamide (13) were isolated from the stems of Dracaena usambarensis Engl. from Kenya. It is important to note that compounds 12 and 13 are being reported from this genus for the first time. Structural elucidation of the isolated compounds was done using spectroscopic (NMR, UV, IR, optical rotation) and spectrometric (HRESIMS) techniques. The absolute and relative configurations of the isolated compounds were determined by employing single crystal X-ray crystallography analysis, NOESY correlations and coupling constants. The anti-inflammatory potencies of the isolated compounds were evaluated by measuring the levels of four cytokines (IL-1β, IL-2, GM-CSF and TNF-α) in the supernatant media of human peripheral blood mononuclear cells (PBMCs) stimulated by lipopolysaccharide (LPS). At the tested concentration of 100 μM, the new conjugated chalcone-stilbene 5 , the dihydrochalcone, 8 and the lignanamide, 13 were substantially more potent than the standard drug, ibuprofen, inhibiting the release of all the cytokines, IL-1β , IL-2, GM-CSF and TNF-α from 0.06–58.04% compared to LPS control. These compounds should therefore be considered for development into anti-inflammatory drug candidates. Compound 7 significantly decreased the release of GM-CSF (6.11% of LPS control) and TNF-α (18.35% of LPS control). The cytokine TNF-α was sensitive to all the tested compounds 1 - 13. Unlabelled Image • Thirteen secondary metabolites isolated from the stem bark of Dracaena usambarensis. • Four new steroidal sapogenins, 1 - 4 and a new conjugated chalcone-stilbene, 5. • The relative configuration of 1 was confirmed with X-ray analysis. • Inhibitory activity of 5 , 8 and 13 , was higher than ibuprofen against all cytokines. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of Tephrosia vogelii seedpods led to the isolation of twelve compounds: vogelisoflavone A (1), vogelisoflavone B (2), isopongaflavone (3), onogenin, luteolin, 4′,7-dihydroxy-3′-methoxyflavanone, trans - p -hydroxycinnamic acid, tephrosin, 2-methoxygliricidol, dehydrorotenone, 6a,12a-dehydro-α-toxicarol and pinoresinol. Compounds 1 and 2 are reported as new natural products. Isopongaflavone (3) was structurally modified using hydrazine to pyrazoisopongaflavone (4). These compounds were characterized based on their NMR and HRESIMS data. Further, four compounds (1–4) were evaluated for their anti-inflammatory effects in lipopolysaccharide (LPS)-stimulated peripheral blood mononuclear cells (PBMCs). Treatment of the LPS-stimulated PBMCs with the compounds at a concentration of 100 μM suppressed the secretion of interleukin IL-1β interferon-gamma (IFN-γ), granulocyte macrophage-colony stimulating factor (GM-CSF) and tumour necrosis factor-alpha (TNF-α). Unlabelled Image • Twelve compounds were isolated from Tephrosia vogelii seedpods. • Two new isoflavones vogelisoflavone A (1) and vogelisoflavone B (2) are reported as new compounds. • Isopongaflavone was modified using hydrazine to pyrazoisopongaflavone. • The compounds exhibited anti-inflammatory effects. [ABSTRACT FROM AUTHOR]

Two new norhopane derivatives namely 3β,6β,22-trihydroxy-7β,11α-di[(4-hydroxybenzoyl)oxy]-21αH-24-norhopa-4(23)-ene (1) and 3β,6β,22-trihydroxy-7β-[(4-hydroxybenzoyl)oxy]-21αH-24-norhopa-4(23)-ene (2) together with two previously reported compounds, including a norhopane, 3β,6β,11α-trihydroxy-7β-[(4-hydroxybenzoyl)oxy]-24-norhopa-4(23),17(21)-diene (3) and a norneohopane, (21αH)-24-norneohopa-4(23), 22(29)-diene-3β,6β,7β-triol 7-caffeate (4) were isolated from the root bark of Fagaropsis angolensis. Elucidation of their structures was achieved by spectroscopic (NMR, IR and UV) and spectrometric (HRESIMS) data and by comparison of these data with those of related compounds in the literature. Compounds 1–4 were evaluated for their anti-inflammatory activity by measuring the levels of cytokines, IL-1β, IL-2, GM-CSF and TNF-α in lipopolysaccharide (LPS) stimulated peripheral blood mononuclear cells (PBMC). All tested compounds decreased secretion of IL-1β and TNF-α. Compounds 2 and 4 caused significant decrease of the production of IL-2, GM-CSF and TNF-α compared to the reference drug, ibuprofen. These findings showed that the root barks of F. angolensis are rich source of norhopane derivatives and further provide a scientific rationale of using this plant in Kenyan folk medicine to relieve pain. Unlabelled Image [ABSTRACT FROM AUTHOR]