Two New Sesquiterpene Derivatives from the Tunisian Endemic Ferula tunetana Pom.

A new sesquiterpene ester, tunetanin A ( 1 ), a new sesquiterpene coumarin, tunetacoumarin A ( 2 ), together with eight known compounds, i.e., coladin ( 3 ), coladonin ( 4 ), isosmarcandin ( 5 ), 13‐hydroxyfeselol ( 6 ), umbelliprenin ( 7 ) propiophenone ( 8 ), β‐sitosterol ( 9 ), and stigmasterol ( 10 ), were isolated from the roots of Ferula tunetana. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D‐ and 2D‐NMR experiments and MS analysis, as well as by comparison with published data. The cytotoxicity of compounds 1 – 7 towards two human colon cancer cell lines, HT‐29 and HCT 116, was evaluated. Compounds 3, 4 , and 6 showed weak cytotoxic activities.     

Terpenoids with Cytotoxic Activity from Roots of Ardisia crispa

Three new terpenoids, ardisiacrispins G-I ( 1 , 4 and 8 ), and eight known compounds, cyclamiretin A ( 2 ), psychotrianoside G ( 3 ), 3-hydroxy-β-damascone ( 5 ), megastigmane ( 6 ), corchoionol C ( 7 ), zingiberoside B ( 9 ), angelicoidenol ( 10 ), trans-linalool-3,6-oxide-β-D-glucopyranoside ( 11 ) were isolated from the roots of Ardisia crispa. The chemical structures of all isolated compounds were elucidated by extensive spectroscopic analyses, such as HR-ESI-MS, 1D and 2D NMR spectra. Ardisiacrispin G ( 1 ) represents the oleanolic-type scaffold featuring a rare 15,16- epoxy system. All compounds were evaluated for the cytotoxicity against two cancer cell lines (U87 MG and HepG2) in vitro. Compounds 1 , 8 and 9 exhibited moderate cytotoxic activity with IC₅₀ values ranging from 7.6±1.1 to 28.8±3.2 μM.     

Azaphilones and Meroterpenoids from the Soft Coral-Derived Fungus Penicillium glabrum glmu003

Two new azaphilone compounds, daldinins G ( 1 ) and H ( 2 ), together with nine known compounds daldinin D ( 3 ), sargassopenilline B ( 4 ), austalide V ( 5 ), austalide K ( 6 ), austalide P ( 7 ), austalide P acid ( 8 ), austalide H ( 9 ), 13-O-deacetyaustalide I ( 10 ), and 17-O-demethylaustalide B ( 11 ), were isolated from the soft coral-derived fungus Penicillium glabrum glmu003. The new structures of 1 and 2 were elucidated on the basis of 1D and 2D NMR, mass spectra, and electronic circular dichroism (ECD) data analysis. Compound 5 showed weak inhibitory activity against pancreatic lipase (PL) with IC₅₀ value of 23.9 μg/mL.     

Four New C19-Diterpenoid Alkaloids from Aconitum nagarum Stapf

Four new aconitine-type C₁₉-diterpenoid alkaloids, were isolated from the roots of Aconitum nagarum Stapf which were named as nagarutines A–D ( 1–4 ), together with eleven known compounds ( 5–15 ). The structures of the compounds were identified by IR, HR-ESI-MS, 1D and 2D NMR spectra. All compounds were tested for the inhibitory effect on LPS induced NO production in RAW 264.7 macrophages, compound 7 showed moderate anti-inflammatory activity effect and Inhibition rate is about 44.50%.     

Lyonin A, a new 9,10-Secograyanotoxin from Lyonia ovalifolia

Phytochemical studies on the branches and leaves of Lyonia ovalifolia yielded a new grayanane diterpenoid, lyonin A ( 1 ), together with two known compounds, secorhodomollolides A and D ( 2 and 3 , resp.). The structure of 1 was elucidated by combination of 1D‐ and 2D‐NMR, and MS analyses. Compound 1 turned out to be a new, highly O‐acylated grayanane diterpenoid, of which ring B has undergone an oxidative cleavage between C(9) and C(10), yielding a system differing from the previously reported grayanane type with a 5/7/6/5 ring system. Results of the cAMP regulation activity assay showed that compounds 2 and 3 at 50 μM induced a significantly decreased cAMP level in N1E‐115 neuroblastoma cells (p<0.001), indicating neuropharmacological potential.     

Phialomyces macrosporus: Chemical Constituents,Antimicrobial Activity and Complete NMR Assignments for the 7,7′‐Biphyscion

Five known secondary metabolites, chrysophanol ( 1 ), 7,7′‐biphyscion ( 2 ), secalonic acid D ( 3 ), mannitol ( 4 ) and trehalose ( 5 ) were isolated for the first time from the extracts of the fungus Phialomyces macrosporus. Their structures were elucidated by NMR methods (1D and 2D NMR analysis), optical activity and ESI‐MS. Complete ¹H and ¹³C assignments were performed for compound 2 . The antimicrobial activity was evaluated by serial microdilution assay for compounds 2 and 3 and results showed that compound 3 exhibited a significant growth inhibition at concentrations of 15.6 mg/ml (S. aureus and S. choleraesius) and 0.97 mg/mL (B. subtilis), comparable to the positive control.     

核桃青皮的化学成分研究——酚类化合物

核桃青皮是一种传统的中药材,含有大量的酚类化合物,具有镇痛、消炎、抑菌、抗肿瘤等功效。为了从核桃青皮中分离得到更多的酚类成分,以利于更好地阐明其作用机理,该研究采用大孔树脂Diaion HP-20SS、凝胶Sephadex LH-20,HPLC等方法对核桃青皮80%的乙醇提取物进行分离纯化。结果表明:共分离了10个单体化合物,它们的结构经质谱(MS)、一维核磁共振谱(~1H NMR和~(13)C NMR)、二维核磁共振谱(HSQC,HMBC)数据的分析及文献数据的比较确定为没食子酸(1),没食子酸甲酯(2),对羟基苯甲酸(3),3,4-二羟基苯甲酸甲酯(4),6-O-咖啡酸-D-葡萄糖(5),6-O-没食子酸-葡萄糖苷(6),4,8-二羟基-1-四氢萘醌(7),5,8-二羟基-4-甲氧基-1-四氢萘酮(8),5,8-二羟基-1-四氢萘酮(9),4-羟基-1-四氢萘酮(10)。其中,化合物5,化合物6为属内首次分离到。该研究结果为进一步深入研究核桃青皮的化学成分和药理作用提供了一定参考。     

Antifungal metabolites from the roots of Diospyros virginiana by overpressure layer chromatography

A preparative overpressure layer chromatography (OPLC) method was successfully used for the separation of two new natural compounds, 4‐hydroxy‐5,6‐dimethoxynaphthalene‐2‐carbaldehyde ( 1 ) and 12,13‐didehydro‐20,29‐dihydrobetulin ( 2 ) together with nine known compounds, including 7‐methyljuglone ( 3 ), diospyrin ( 4 ), isodiospyrin ( 5 ), shinanolone ( 6 ), lupeol ( 7 ), betulin ( 8 ), betulinic acid ( 9 ), betulinaldehyde ( 10 ), and ursolic acid ( 11 ) from the acetone extract of the roots of Diospyros virginiana. Their identification was accomplished by 1D‐ and 2D‐NMR spectroscopy and HR‐ESI‐MS methods. All the isolated compounds were evaluated for their antifungal activities against Colletotrichum fragariae, C. gloeosporioides, C. acutatum, Botrytis cinerea, Fusarium oxysporum, Phomopsis obscurans, and P. viticola using in vitro micro‐dilution broth assay. The results indicated that compounds 3 and 5 showed high antifungal activity against P. obscurans at 30 μM with 97.0 and 81.4% growth inhibition, and moderate activity against P. viticola (54.3 and 36.6%). It appears that an optimized OPLC system offers a rapid and efficient method of exploiting bioactive natural products.     

Chemical constituents from Celastrus aculeatus Merr.

Phytochemical investigation of Celastrus aculeatus Merr. led to the isolation of nine compounds. Their structures were identified to be dulcitol (1), β-sitosterol (2), n-tritriacontane (3), nimbidiol (4), pristimerin (5), p-hydroxybenzoic acid (7), vanillic acid (8), 3, 5-dimethoxy-4-hydroxybenzoic acid (9) and a new compound named pristimerol (6) on the basis of mass and NMR spectra. This is the first report of phenolic acids (compounds 7–9) from C. aculeatus Merr. We present the HR-MS, 1D NMR (¹H, ¹³C NMR, DEPT) and 2D NMR (HMBC) data of the new compound (6).     

Monalbidins A–E,Decalins with Potential Cytotoxic Activities from Marine Derived Fungus Monascus albidus BB3

Five new decalins, monalbidins A–E ( 1 , 2 and 7–9 ), together with 16 known compounds ( 3 – 6 and 10–21 ), were isolated from the AcOEt extract of marine derived fungus Monascus albidus BB3 cultured in GPY medium. Among the known compounds, 1-hydroxymonacolin L ( 11 ), dehydromonacolin J ( 15 ), 8-O-acetylmonacolin J ( 19 ) and O-acetylmonacolin K ( 21 ) were separated from natural sources for the first time. Their structures were determined by comprehensive analysis on the 1D and 2D NMR, HR-ESI-MS, UV and IR data, and their absolute configurations were assigned by experimental and calculated ECD data, and X-ray single-crystal diffraction analysis. Monalbidins C and D ( 7 and 8 ), monacolin K methyl ester ( 13 ), dehydromonacolin L ( 14 ), dehydromonacolin K ( 16 ), monacolin K ( 20 ) and O-acetylmonacolin K ( 21 ) showed moderate cytotoxicity against human cancer cell lines SUNE1, HepG2, QGY7701, HCT116 and MDA-MB-231.     

13,14‐seco‐Withanolides from Physalis minima with Potential Anti‐inflammatory Activity

Four new 13,14‐seco‐withanolides, minisecolides A – D ( 1  –  4 ), together with three known analogues 5  –  7 , were isolated from the whole plants of Physalis minima. The structures of new compounds were determined on the basis of spectroscopic analysis, including ¹H‐, ¹³C‐NMR, 2D‐NMR (HMBC, HSQC, ROESY), and HR‐ESI‐MS. Evaluation of all isolates for their inhibitory effects on nitric oxide (NO) production was conducted on lipopolysaccaride‐activated RAW264.7 macrophages. Compounds 2 , 3 , 5 , and 6 showed inhibitory activities, especially for compound 5 with IC₅₀ value of 3.87 μm .     

Bioactive Neolignans and Other Compounds from Magnolia grandiflora L.: Isolation and Antiplasmodial Activity

Bioassay‐guided fractionation of a methanol extract of Magnolia grandiflora against Plasmodium falciparum yielded two new ( 1 and 2 ) and six known ( 3 – 8 ) bioactive compounds. The structures of the new compounds were assigned by mass spectrometric and 1D‐ and 2D‐NMR data. Known compounds were identified by comparison of ¹H‐NMR and MS data with literature data. The two known neolignans 3 and 4 showed moderate antiplasmodial activity with the IC₅₀ values of 2.8 ± 0.1 and 3.4 ± 0.1 μm , respectively. Weak antiplasmodial activity was recorded for compounds 1 , 2 , 5 , 6 , 7 , and 8 , with the IC₅₀ values of 38 ± 2, 23 ± 2, 16.5 ± 0.2, 86 ± 1, 44 ± 4, and 114 ± 9 μm , respectively.     

Three New Constituents with Anti-Inflammatory and Antimicrobial Activities in Vitro from the Roots of Capsicum annuum L.

Three new compounds, including two new sesquiterpenes ( 1–2 ), named Annuumine E−F, and one new natural product, 3-hydroxy-2,6-dimethylbenzenemethanol ( 3 ), together with seventeen known compounds ( 4–20 ) were isolated from the ethanol extract of the roots of Capsicum annuum L. Among them, five compounds ( 4 , 5 , 9 , 10 and 20 ) were isolated from this plant for the first time. The structures of new compounds ( 1–3 ) were determined via detailed analysis of the IR, HR-ESI-MS and 1D and 2D NMR spectra. The anti-inflammatory activities of the isolated compounds were evaluated by their ability to reduce NO release by LPS-induced RAW 264.7 cells. Notably, compound 11 exhibited moderate anti-inflammatory activity (IC₅₀=21.11 μM). Moreover, the antibacterial activities of the isolated compounds were also evaluated.     

Chemical constituents of the medicinal plant Indigofera spicata Forsk (Fabaceae) and their chemophenetic significance

The chemical investigation of the whole plant of Indigofera spicata Forsk (Fabaceae), a medicinal plant from Cameroon, resulted in the isolation of a new benzofuran, named spibenzofuran (1a), together with ten known secondary metabolites including one benzofuran (2), one flavonoid (3), one saponin (6), two triterpenes (4 and 5), two steroids (8 and 11), one phthalate (7) and two fatty acids (9 and 10). All these compounds have been isolated for the first time from this plant. The structures of the isolated compounds were established by spectroscopic analysis including HR-ESI-MS, 1D and 2D NMR and by comparison of our data with the reported data. The isolated compounds might be considered as the chemophenetic markers of this species, and antibacterial and urease inhibitory activities of some isolated compounds were assessed.     

Caryophyllene Sesquiterpenes from Pulicaria vulgaris Gaertn.: Isolation,Structure Determination,Bioactivity and Structure−Activity Relationship

A new caryophyllene, named pulicaryenne A ( 1 ), along with four other known caryophyllene derivatives ( 2 , 3 , 4 and 5 ) were isolated from the ethyl acetate extract of aerial parts of Pulicaria vulgaris Gaertn . (Asteraceae). All compounds were isolated for the first time from this species. Compound 2 was identified as a new epimer of a known caryophyllene derivative isolated previously from P. dysenterica. Their structures were established by spectroscopic means including NMR analysis (1D‐ and 2D‐NMR) and ESI‐TOF‐MS. All compounds were evaluated for their anticholinesterase, antityrosinase and cytotoxic activities against two human cell lines (A549 and HeLa). Results showed that compound 5 exhibited the highest cytotoxic effect against A549 and anticholinesterase activity with IC₅₀ values of 8.50±0.75 and 6.45±0.09 μg/mL, respectively. Furthermore, compound 5 showed also an interesting antityrosinase activity with percent inhibition value of 79.0±2.5 % at 50 μg/mL. The bioactivity and drug likeness scores of the isolated compounds 1–5 were calculated using Molinspiration software and discussed. These results may suggest that the five caryophyllene derivatives endowed with good biological properties, which could be used as bioactive alternatives in pharmaceutical preparations.     

Piptadenin,a Novel 3,4‐Secooleanane Triterpene and Piptadenamide,a New Ceramide from the Stem Bark of Piptadeniastrum africanum (Hook.f.) Brenan

Piptadenin ( 1 ), a new triterpene along with piptadenamide ( 10 ), a new ceramide, have been isolated from the AcOEt‐soluble fraction of the MeOH extract of the stem bark of Piptadeniastrum africanum along with nine known compounds, 1‐O‐[(3β,22β)‐3,22‐dihydroxy‐28‐oxoolean‐12‐en‐28‐yl]‐β‐d ‐glucopyranose ( 2 ), 22β‐hydroxyoleanic acid ( 3 ), oleanic acid ( 4 ), lupeol ( 5 ), betulinic acid ( 6 ), 5α‐stigmasta‐7,22‐dien‐3β‐ol ( 7 ), 5α‐stigmasta‐7,22‐dien‐3‐one ( 8 ), (3β)‐stigmast‐5‐en‐3‐yl β‐d ‐glucopyranoside ( 9 ) and 2,3‐dihydroxypropyl hexacosanoate ( 11 ). Except for compound 11 , all the isolated compounds are reported for the first time from this plant. The structures of the isolated compounds were elucidated by spectroscopic data including 1D and 2D NMR. The pure compounds 1 – 11 were subjected to the pharmacological screening and compounds 2 , 5 – 7 and 9 exhibited potent urease inhibitory activity with IC₅₀ value of 25.8, 28.9, 30.1, 31.8 and 32.7 μm , respectively, whereas compound 1 showed moderate activity (IC₅₀ = 98.7 μm ). The potent urease inhibitory activity supplemented the previous literature reports and medicinal uses of this plant.     

Tirucallane Triterpenoids from the Stems of Brucea mollis

Three new tirucallane triterpenoids, brumollisols A–C ( 1 – 3 , resp.), together with five known analogues, (23R,24S)‐23,24,25‐trihydroxytirucall‐7‐ene‐3,6‐dione ( 4 ), piscidinol A ( 5 ), 24‐epipiscidinol A ( 6 ), 21α‐methylmelianodiol ( 7 ), and 21β‐methylmelianodiol ( 8 ), were isolated from an EtOH extract of the stems of Brucea mollis. Their structures were elucidated by means of spectroscopic methods including 1D‐ and 2D‐NMR techniques and mass spectrometry. In the in vitro assays, compound 6 exhibited significant cytotoxic activity against A549 and BGC‐823 cancer cells with IC₅₀ values of 1.16 and 3.01 μM , respectively. At a concentration of 10 μM , compounds 1 – 5, 7 , and 8 were found to inhibit NO production in mouse peritoneal macrophages with inhibitory ratios ranging from 39.8±7.7 to 68.2±4.5%.     

Hypofolins A – L,ent‐Labdane Diterpenoids from the Roots of Hypoestes phyllostachya ‘Pink Splash’

Twelve new ent‐labdane diterpenoids, hypofolins A – F ( 1 – 6 ) and hypofolins G – L ( 7a / 7b , 8a / 8b , and 9a / 9b ), were isolated from the roots of Hypoestes phyllostachya ‘Pink Splash’. Their structures were elucidated by extensive 1D‐ and 2D‐NMR spectroscopic and HR‐MS data. The absolute configurations of 1 , 2 , 5 , and 7a / 7b were determined by single crystal X‐ray diffraction and ECD analysis, as well as chemical transformations. Compounds 7a / 7b , 8a / 8b , and 9a / 9b were isolated as three pairs of interconverting mixture of two isomers between ketone and hemiketal types. Compound 1 showed weak cytotoxicity against SMMC‐7721 cell line with IC₅₀ value of 31.40 μm .     

Pelliolatifolias A-D,Four Undescribed Compounds from Pellionia latifolia Boerl. and Their Nitric Oxide Production Inhibitory Activity

Four undescribed compounds ( 1 – 4 ) named pelliolatifolias A−D together with seven known compounds trans-clovamide ( 5 ), N-trans-caffeoyl-4-hydroxyphenylalanine methyl ester ( 6 ), N-trans-caffeoyl-3,4-dihydroxyphenylalanine methyl ester ( 7 ), luteolin 4’-O-β-D-glucopyrannoside ( 8 ), cis-syringin ( 9 ), trans-syringin ( 10 ), and citroside A ( 11 ) have been isolated from the methanol extract of the Pellionia latifolia leaves. Their chemical structures were elucidated based on extensive analyses of HR-ESI-MS, 1D and 2D NMR, and CD spectra. Compounds 1 – 7 , 9 and 10 showed moderate inhibition of NO production in LPS-activated RAW264.7 cells with their IC₅₀ values ranging from 39.27 to 75.42 μM, compared to that of the positive control compound, dexamethasone, IC₅₀ value of 14.20 μM.