Constituents of Flowers of Murraya Paniculata

Three new coumarins, yuehgesin-A (1), -B (2) and -C (3) and 22 compounds—murracarpin (4), mupanidin (5), isomeranzin (6), murralongin (7), scopoletin (10), 7-methoxy-8-(l′-ethoxy-2′-hydroxy-3′-methyl-3′-butenyl)coumarin (11), umbelliferone (12), paniculatin (13), braylin (14), auraptenol (15), meranzin hydrate (16), minumicrolin (17), scopolin (18), caffeine (19), 3,3′,4′,5,5′,6,7-heptamethoxyflavone (20), 4-hy-droxybenzaldebyde (21), p-hydroxybenzoic acid (22), cis- and trans-ferulic acid (23), cis- and transmethyl ferulate (24) and trans-ethylferulate (25)—were isolated and characterized from fresh flowers of Murraya paniculata collected in Taiwan. Their structures were elucidated by spectral methods. The chemotaxonomy of Murraya paniculata is, discussed.     

Lycopodium Alkaloids from Huperzia serrata

Three new lycopodium alkaloids, huperserramines A–C ( 1 – 3 , resp.), along with 15 known ones, lycopodine‐6α,11α‐diol ( 4 ), lycoposerramine H ( 5 ), lycoposerramine I ( 6 ), lycopodine‐6α‐ol ( 7 ), lycoposerramine M ( 8 ), diphaladine A ( 9 ), lycoposerramine K ( 10 ), lycoposerramine W ( 11 ), huperzine M ( 12 ), luciduline ( 13 ), phlegmariuine N ( 14 ), huperzine A ( 15 ), huperzine B ( 16 ), lycodine ( 17 ), and lycoposerramine R ( 18 ), were isolated from the whole plant of Huperzia serrata. Their structures were established by spectroscopic methods, including 2D‐NMR and MS analyses. All the isolates were evaluated for their inhibitory effects on acetylcholinesterase (AChE) and α‐glucosidase. As a result, lycopodine‐6α,11α‐diol ( 4 ) exhibited more potent α‐glucosidase inhibitory activity (IC₅₀ 148±5.5 μM ) than the positive control acarbose (IC₅₀ 376.3±2.7 μM ).     

Two New Nimbolinin‐Type Limonoids from the Fruits of Melia toosendan

Two new nimbolinin‐type limonoids, 12‐ethoxynimbolinins E and F ( 1 and 2 , resp.), together with seven known analogues, 1α‐benzoyloxy‐3α‐acetoxyl‐7α‐hydroxy‐12β‐ethoxynimbolinin ( 3 ), nimbolinin B ( 4 ), meliatoosenin L ( 5 ), 14,15‐deoxy‐11‐oxohavanensin 3,12‐diacetate ( 6 ), 12α‐hydroxymeliatoosenin ( 7 ), toosendansin A ( 8 ), and toosendansin C ( 9 ), were isolated from the fruits of Melia toosendan. The structures of these compounds were elucidated by spectroscopic analysis. All the compounds were evaluated for their cytotoxicity against five tumor cell lines.     

The Constituents of Cananga odorata

Sixteen compounds, (+)-ushinsunine-β-N-oxide ( 1 ), cleistopholine ( 2 ), liriodenine ( 3 ), (-)-anonaine ( 4 ), (+)-nornuciferine ( 5 ), (+)-N-acetylnornuciferine ( 6 ), (-)-ushinsunine ( 7 ), (-)-norushinsunine ( 8 ), (-)-asimilobine ( 9 ), (+)-reticuline ( 10 ), N-trans-feruloyltyramine ( 11 ), β-sitosterol (12) and stigmasterol ( 13 ), lyscamine ( 14 ), (-)-anaxagoreine ( 15 ) and trans-cinnamic acid ( 16 ) were isolated from the methanolic extract of the Cananga odorata. Among them, 1 is a new stereoisomer of ushinsunine-β-N-oxide. The structures of these compounds were established by means of spectral experiments.     

Three New Triterpenoids from Lycopodium japonicum Thunb

Three new triterpenoids, (3β,8β,14α,21α)‐26,27‐dinoronocerane‐3,8,14,21‐tetrol ( 1 ), (3β,8β,14α,21β)‐26,27‐dinoronocerane‐3,8,14,21‐tetrol ( 2 ), and lycopodiin A ( 3 ), together with four known compounds, lycoclavanol ( 4 ), lycoclaninol ( 5 ), α‐onocerin ( 6 ), and 3‐epilycoclavanol ( 7 ), were isolated from Lycopodium japonicum Thunb (Lycopodiaceae). Their structures were established by means of spectroscopic analyses. Compounds 3 and 7 showed moderate antitumor activity. Compounds 4 and 6 exhibited acetylcholinesterase inhibition activity.     

Biflavonoids,Lignans, and Related Compounds from the Roots of Diplomorpha canescens

Two new biflavonoids, 14″‐O‐methyldihydrodaphnodorin B ( 1 ) and 14″‐O‐methyldaphnodorin J ( 2 ), along with 16 known compounds, i.e., dihydrodaphnodorin B ( 3 ), daphnodorin J ( 4 ), 3″‐epidihydrodaphnodorin B ( 5 ), daphnodorin B ( 6 ), neochamaejasmin B ( 7 ), sikokianin B ( 8 ), (?)‐syringaresinol ( 9 ), (?)‐syringaresinol 4‐O‐β‐D ‐glucopyranoside ( 10 ), (+)‐nortrachelogenin ( 11 ), (?)‐lariciresinol ( 12 ), (?)‐pinoresinol ( 13 ), syringin ( 14 ), syringinoside ( 15 ), daphnoretin ( 16 ), phorbol 13‐acetate ( 17 ), and methyl paraben ( 18 ) were isolated from the roots of Diplomorpha canescens (Meisn.) C.A. Meyer . The structures were determined on the basis of spectroscopic data.     

Miscible blends of amorphous polymers

Thirty-five polymethacrylate/chlorinated polymer blends were investigated by differential scanning calorimetry. Poly(ethyl), poly(n-propyl), poly(n-butyl), and poly(n-amyl methacrylate)s were found to be miscible with poly(vinyl chloride) (PVC), chlorinated PVC, and Saran, but immiscible with a chlorinated polyethylene containing 48% chlorine. Poly(methyl) (PMMA), poly(n-hexyl) (PHMA), and poly(n-lauryl methacrylate)s were found to be immiscible with the same chlorinated polymers, except the PMMA/PVC, PMMA/Saran, and PHMA/Saran blends, which were miscible. A high chlorine content of the chlorinated polymer and an optimum CH₂/COO ratio of the polymethacrylate are required to obtain miscibility. However, poly(methyl), poly(ethyl), poly(n-butyl), and poly(n-octadecyl acrylate)s were found to be immiscible with the same chlorinated polymers, except with Saran, indicating a much greater miscibility of the polymethacrylates with the chlorinated polymers as compared with the polyacrylates.     

Physicochemical characterization of nanobidentate ferrocene‐based Schiff base ligand and its coordination complexes: Antimicrobial,anticancer, density functional theory,and molecular operating environment studies

A novel bidentate Schiff base ligand (HL, Nanobidentate Ferrocene based Schiff base ligand L (has one replaceable proton H)) was prepared via the condensation of 2‐amino phenol with 2‐acetyl ferrocene. The ligand was characterized using elemental analysis, mass spectrometry, infrared (IR) spectroscopy, ¹proton nuclear magnetic resonance (H‐NMR) spectroscopy, scanning electron microscopy (SEM), and thermal analysis. The corresponding 1:1 metal complexes with some transition‐metal ions were additionally characterized by their elemental analysis, molar conductance, SEM, and thermogravimetric ana1ysis (TGA). The complexes had the general formula [M(L)(Cl)(H₂O)₃]xCl·nH₂O (M = Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II)), (x = 0 for Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II), x = 1 for Cr(III) and Fe(III)), (n = 1 for Cr(III), n = 3 for Mn(II) and Co(II), n = 4 for Fe(III), Ni(II), Cu(II), Zn(II), and Cd(II)). Density functional theory calculations on the HL ligand were also carried out in order to clarify molecular structures by the B31YP exchange‐correlation function. The results were subjected to molecular orbital diagram, highest occupied mo1ecu1ar orbital–lowest occupied molecular orbital, and molecular electrostatic potential calculations. The parent Schiff base and its eight metal complexes were assayed against four bacterial species (two Gram‐negative and two‐Gram positive) and four different antifungal species. The HL ligand was docked using molecular operating environment 2008 with crystal structures of oxidoreductase (1CX2), protein phosphatase of the fungus Candida albicans (5JPE), Gram(?) bacteria Escherichia coli (3T88), Gram(+) bacteria Staphylococcus aureus (3Q8U), and an androgen‐independent receptor of prostate cancer (1GS4). In order to assess cytotoxic nature of the prepared HL ligand and its complexes, the compounds were screened against the Michigan cancer foundation (MCF)‐7 breast cancer cell line, and the IC₅₀ values of compounds were calculated.     

Solid phase microextraction and gas chromatography mass spectrometry analysis of Zingiber officinale and Curcuma longa

SPME analysis of Zingiber officinale Roscoe and Curcuma longa L. were performed by using a DVB/CARB/PDMS fiber. The SPME analysis of Zingiber officinale showed that the main components found were camphene (7.27%), geranial (8.37%), α-zingiberene (14.50%), α-farnesene (9.14%), β-bisabolene (6.52%), and β-sesquiphellandrene (9.92%). The SPME analysis of Curcuma longa showed that main components were p-cymene (12.96%) and ar-turmerone (12.08%). Other components were β-phellandrene (7.86%), terpinolene (6.97%), ar-curcumene (8.53%), α-zingiberene (8.46%), and β-sesquiphellandrene (7.37%).     

Alkaloids from the Leaves of Fissistigma Glaucescens

Two new alkaloids, glaucenamide ( 1 ) and fissiceine ( 2 ), along with fifteen known ones, liriodenine ( 3 ), oxocrebanine ( 4 ), kuafumine ( 5 ), oxoxylopine ( 6 ), atherospermidine ( 7 ), (‐)‐xylopine ( 8 ), (‐)‐N‐acetylxylopine ( 9 ), N‐trans‐feruloyltyramine ( 10 ), aristololactam BII ( 11 ), aristololactam BIII ( 12 ), aristololactam AII ( 13 ), piperolactam A ( 14 ), goniothalactam ( 15 ), norcepharadion B ( 16 ), and noraristolodione ( 17 ) were isolated from the methanolic extracts of the Fissistigma glaucescens. The structures of these compounds were established by means of spectral analysis.     

Composition of essential oils from four Apiaceae and Asteraceae species growing in Uzbekistan

The chemical composition of essential oils isolated from the aerial parts of Heracleum lehmannianum, Prangos pabularia, Pseudohandelia umbellifera and Pulicaria salviifolia, all of them growing in Uzbekistan, were determined by GC-MS analysis. The main components of the oil from H. lehmannianum were α-phellandrene (10.5%), 1-butanol (9.0%), δ-cadinene (6.2%), α-cadinol (5.7%), τ-muurolol (3.1%), 4-terpineol (2.4%) and α-muurolene (2.6%), while cis-allo-ocimene (17.6%), δ-3-carene (14.2%), limonene (7.6%), 2,4,6-trimethylbenzaldehyde (6.8%), α-terpinolene (6.1%), β-ocimene (4.3%), α-ocimene (4.2%), α-phellandrene (4.2%) were the major oil components in P. pabularia, and borneol (4.4%), t-cadinol (4.1%), α-humulene oxide (4.0%), caryophyllene oxide (3.6%), bornyl chloride (3.1%), β-pinene (2.9%) in P. umbellifera. The essential oil of P. salviifolia had a much more complex composition which was dominated by 4-terpineol (13.4%), α-cadinol (5.7%), 6-epi-shyobunol (5.2%), γ-terpinene (5.0%), δ-cadinene (4.4%), α-terpinene (3.5%).     

New Alkaloids from Hippeastrum papilio (Ravenna) Van Scheepen

A new phytochemical study of the indigenous Brazilian species Hippeastrum papilio is reported herein. Three novel Amaryllidaceae alkaloids were isolated, including hippapiline ( 1 ), papiline ( 2 ), and 3‐O‐demethyl‐3‐O‐(3‐hydroxybutanoyl)haemanthamine ( 3 ). Their structures were determined by physical and spectroscopic methods. In addition, the known alkaloids, haemanthamine ( 4 ), galanthamine ( 5 ), narwedine ( 6 ), 11β‐hydroxygalanthamine ( 7 ), apogalanthamine ( 8 ), and 9‐O‐demethyllycosinine B ( 9 ) were identified. The unusual cis‐B/C‐ring fusion for the new homolycorine representative hippapiline was ratified by NMR and CD spectroscopy.     

Three New Pregnane Alkaloids from Veratrum taliense

Three new alkaloids, 3‐O‐acetylveralkamine ( 1 ), veralkamine 3‐(β‐D ‐glucopyranoside) ( 2 ), and 6,7‐epoxyverdine ( 3 ), together with five known alkaloids, veramitaline, veralkamine ( 4 ), angeloylzygadenine, veratroylzygadenine, and veramiline 3‐(β‐D ‐glucopyranoside), were isolated from the whole plants of Veratrum taliense. Their structures were elucidated on the basis of spectroscopic analysis, and the NMR data of veralkamine ( 4 ) are given for the first time. In addition, the cytotoxic activities of all isolated compounds, except for veramitaline, were tested.     

Pseudolarolides O and P,Two Novel Triterpene Dilactones from Pseudolarix kaempferi

Pseudolarolides O ( 1 ) and P ( 2 ), two novel triterpenoids with a cycloartane‐type framework, were isolated from the seeds of Pseudolarix kaempferi Gord. (Pinaceae). Their structures were elucidated as (16R,23S,25R)‐16,23‐epoxy‐3,4 : 9,10‐disecocycloartan‐1(10),9(11)‐diene‐3(4),26(23)‐diolide ( 1 ), and (9S,16R,23S,25R)‐1,9 : 16,23‐diepoxy‐8,9 : 9,10‐disecocycloartan‐1(29),5(6),10(19)‐triene‐3(4),26(23)‐diolide ( 2 ), respectively, on the basis of spectroscopic techniques and X‐ray‐diffraction studies.     

Chemical composition and antimicrobial activity of the essential oil of Mentha mozaffarianii Jamzad growing wild and cultivated in Iran

The aerial parts of wild and cultivated Mentha mozaffarianii Jamzad were collected at full flowering stage from two provinces (Hormozgan and Fars) of Iran. The essential oils were extracted by a Clevenger approach and analysed using GC and GC–MS. The main components in wild plants were piperitenone (33.85%), piperitone (21.18%), linalool (6.89%), pulegone (5.93%), 1, 8.cineole (5.49%), piperitenone oxide (5.17%) and menthone (4.69%) and in cultivated plants, cis-piperitone epoxide (28.89%), linalool (15.36%), piperitone (11.57%), piperitenone oxide (10.14%), piperitenone (8.42%),1,8-cineole (3.60%) were the main constituents in essential oil. The in vitro antimicrobial activity of the essential oil of M. mozaffarianii was studied against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli and Candida albicans. The results of the bioassays showed that the oil exhibited high antimicrobial activity against all the tested pathogens.     

Four New Podocarpane‐Type Trinorditerpenes from Aleurites moluccana

Four new podocarpane‐type trinorditerpenenes, (5β,10α)‐12,13‐dihydroxypodocarpa‐8,11,13‐trien‐3‐one ( 1 ), (5β,10α)‐12‐hydroxy‐13‐methoxypodocarpa‐8,11,13‐trien‐3‐one ( 2 ), (5β,10α)‐13‐hydroxy‐12‐methoxypodocarpa‐8,11,13‐trien‐3‐one ( 3 ), and (3α,5β,10α)‐13‐methoxypodocarpa‐8,11,13‐triene‐3,12‐diol ( 4 ), together with four known diterpenes, 12‐hydroxy‐13‐methylpodocarpa‐8,11,13‐trien‐3‐one ( 5 ), spruceanol ( 6 ), ent‐3α‐hydroxypimara‐8(14),15‐dien‐12‐one ( 7 ), and ent‐3β,14α‐hydroxypimara‐7,9(11),15‐triene‐12‐one ( 8 ), were isolated from the twigs and leaves of Aleurites moluccana. Their structures were elucidated by means of comprehensive spectroscopic analyses, including NMR and MS. Except 8 , all compounds were evaluated for their cytotoxicity; compound 4 exhibited moderate inhibitory activity against Raji cells with an IC₅₀ value of 4.24 μg/ml.     

Synthesis and characterization of polymers from itaconic acid derivatives

Some itaconic acid derivatives were prepared and polymerized, in which itaconic acid (IA), β-monoalkyl itaconates (mRI), dialkyl itaconates (DRI), N-substituted itaconamates (IAE), itaconamides (IAm), itaconic anhydride (IAn), N-alkylitaconimides (RII), and N-(alkyl-substituted phenyl)itaconimides (RPhII) are included. The polymerization reactivity was examined, and discussed in relation to the structure of the monomers. The structure and some properties of the resulting polymers were investigated. Some citraconic acid (CA) and mesaconic acid (MA) derivatives were also polymerized, and their reactivities were compared with the corresponding IA derivatives.     

Comparative essential oil composition of aerial parts of Tanacetum dumosum Boiss. from Southern Zagros,Iran.

The essential oils of leaves and flowers of Tanacetum dumosum Boiss., an endemic medicinal shrub, were extracted by using hydrodistillation method and analysed using GC and GC–MS. A total of 43 and 44 compounds were identified in the essential oils from the leaves and flowers of T. dumosum, respectively. The major chemical constituents of leaves oil were borneol (27.9%), bornyl acetate (18.4%), 1,8-cineol (17.5%), α-terpineol (5.3%), cis-chrysanthenyl acetate (3.3%), camphene (2.7%) and terpinene-4-ol (1.9%), while the main components of the flower oil were isobornyl-2-methyl butanoate (41.1%), trans-linalyl oxide acetate (11.9%), 1,8-cineole (7.7%), thymol (4.2%), linalool (3.9%), camphor (2.9%), isobornyl propanoate (2.9%), α-terpineol (2.1%) and caryophyllene oxide (2.0%). Major qualitative and quantitative variations for some main chemical compounds among different aerial parts of T. dumosum were identified. High contents of borneol, bornyl acetate, 1,8-cineol and linalool in the leaves and flowers of T. dumosum show its potential for use in the food and perfumery industry.     

Monoterpenoids from the Fruit of Gardenia jasminoides

Eight new monoterpenoids, jasminoside J ( 1 ), jasminoside K ( 2 ), 6′‐O‐trans‐sinapoyljasminoside B ( 3 ), 6′‐O‐trans‐sinapoyljasminoside L ( 4 ), jasminosides M–P ( 5 – 8 ), together with three known analogues, jasminoside C ( 9 ), jasminol E ( 10 ), and sacranoside B ( 11 ), were isolated from the fruit of Gardenia jasminoides Ellis (Rubiaceae). Their structures were elucidated by spectral and chemical methods.     

Novel Sesquiterpenes from the Fungus Lactarius piperatus

Four novel sesquiterpenes, namely 7α,8β,13‐trihydroxy‐5,13‐marasmanolide ( 2 ), isoplorantinone ( 5 ), 4,8,14‐trihydroxyilludala‐2,6,8‐triene ( 6 ), and 8‐hydroxy‐8,9‐secolactara‐1,6‐dien‐5,13‐olide ( 10 ), together with six known ones, 7α,8β‐dihydroxy‐5,13‐marasmanolide ( 1) , 7α,8α‐dihydroxy‐5,13‐marasmanolide ( 3 ), isolactarorufin ( 4 ), blennin A ( 7 ), blennin D ( 8 ), and lactarorufin ( 9 ), were isolated from the ethanolic extract of Lactarius piperatus. The structures of these sesquiterpenes, representing diversified structural types, were determined mainly by spectroscopic methods, especially 2D‐NMR techniques. The structure of 6 was further confirmed by a single‐crystal X‐ray‐diffraction determination.