Constituents from the Roots of Semiaquilegia adoxoides

In present literature search, some cyano-containing compounds, which are very rare in plants, from the traditional anticancer herb Tiankuizi were reported. To find more cyano-containing compounds in the important plant Semiaquilegia adoxoides （DC） Makino （Chinese name Tiankuizi）, the isolation of the chemical constituents was investigated for advancing the research. Two new compounds, a new alkaloid, 1,2,3,4-tetrahydro-6-hydroxy-1[（3,4-dihydroxyphenyl）methyl]-7-methoxy-2,2-dimethyl-isoquinolinium, named Semiaquilegine A （1）, and a new ester, 3-（4＇-hydroxyphenyl）-2-propenoic acid （4＂-carboxyl）-phenyl ester （2）, and four cyano-containing compounds, （Z）-6a-（β-D-glucosyloxy）-4a,5a-dihydroxy-2-cyclohexene-△^1,a-acetonitrile （3）, （L0-6α-（β-D-glucosyloxy）-4α-hydroxy-2-cyclohexene-△^1,α-acetonitrile （4）, lithospermoside （5）, ehretioside B （6）, as well as eleven known compounds, were isolated from the roots of Semiaquilegia adoxoides. The structures of new compounds 1 and 2 were elucidated mainly by 1D/2D-NMR techniques. Very unusual cyano-containing compounds 3 and 4 were first isolated from Ranunculaceae family. Hitherto, there were six cyano-containing compounds found in the herb.     

Synthesis and antibacterial activity of novel series of 2‐(p‐tolyloxy)‐3‐(5‐(pyridin‐4‐yl)‐1,3,4‐oxadiazol‐2‐yl)quinoline

A new series of 2‐(p‐tolyloxy)‐3‐(5‐(pyridin‐4‐yl)‐1,3,4‐oxadiazol‐2‐yl)quinoline were synthesized from oxidative cyclization of N′‐((2‐(p‐tolyloxy)quinoline‐3‐yl)methylene)isonicotinohydrazide in DMSO/I₂ at reflux condition for 3–4 h. The structures of the new compounds were confirmed by elemental analyses as well as IR, ¹H‐NMR, and mass spectral data. All the synthesized compounds were screened for their antibacterial activities against various bacterial strains. Several of these compounds showed potential antibacterial activity. J. Heterocyclic Chem., (2011).     

Eupatozansins A – C,Sesquiterpene Lactones from Eupatorium chinense var. tozanense

Phytochemical investigation of Eupatorium chinense var. tozanense has resulted in the isolation of three new germacranolides, designated as eupatozansins A–C ( 1 – 3 ), along with five known compounds, (5S,6R,7R,8R)‐8‐angeloyloxy‐2‐oxoguaia‐1(10),3,11(13)‐trien‐12,6‐olide ( 4 ), costunolide ( 5 ), leptocarpin ( 6 ), 2α‐hydroxyeupatolide 8‐O‐angelate ( 7 ), and quercetin ( 8 ). The structures of the new compounds were identified by 1D and 2D NMR experiments, as well as high‐resolution mass spectrometry. The in vitro cytotoxic activities of compounds 1 – 8 were evaluated.     

A New Pregnane and a New Diphenylmethane from the Root Barks of Periploca sepium

A new polyoxygenated pregnane genin and a new diphenylmethane, along with five known pregnane derivatives, were isolated from the root barks of Periploca sepium. The structures of the new compounds were elucidated as (3β,14β)‐3,14‐dihydroxy‐21‐methoxypregn‐5‐en‐20‐one ( 1 ) and 2‐hydroxy‐5‐(2‐hydroxy‐4‐methoxybenzyl)‐4‐methoxybenzaldehyde ( 2 ) on the basis of spectroscopic methods, especially 2D‐NMR and MS analyses. The known compounds were identified by comparing their physical and spectroscopic data with those reported in the literature.     

Four New Compounds from Sinacalia tangutica

Four new compounds, 9α‐hydroxy‐1β‐methoxycaryolanol ( 1 ), stigmast‐5‐ene‐7α,22α‐diol‐3β‐tetradecanoate ( 2 ), 7‐O‐(6′‐acetoxy‐β‐D ‐glucopyranosyl)coumarin ( 3 ), and 8‐O‐(6′‐acetoxy‐β‐D ‐glucopyranosyl)‐7‐hydroxycoumarin ( 4 ), together with ten known compounds, were isolated from the aerial parts of Sinacalia tangutica. The structures of the new compounds were established by means of extensive spectroscopic analyses (1D‐ and 2D‐NMR, EI‐MS, HR‐ESI‐MS, as well as IR and UV) and by comparison of their spectroscopic data with those of structurally related compounds reported in the literature.     

Three New Caged Prenylxanthones from Garcinia bracteata

Three new caged prenylxanthones (xanthone=9H‐xanthen‐9‐one), named neobractatin ( 1 ), 3‐O‐methylneobractatin ( 2 ), and 3‐O‐methylbractatin ( 3 ), along with eight known compounds, were isolated from the twig of Garcinia bracteata. The structures of the new compounds were elucidated on the basis of 1D‐ and 2D‐NMR experiments, including HMBC, HSQC, ¹H,¹H‐COSY, and ROESY, as well as HR‐MS analysis.     

Triterpenoids and other Constituents from Euphorbia Humifusa

A novel lupane‐type triterpenoid, 3,4‐seco‐lupa‐4(23), 20(29)‐dien‐24‐hydroxy‐3‐oic acid (1) and a new cycloartane‐type triterpenoid, 23(E)‐cycloart‐23‐en‐25‐ethoxy‐3β‐ol (7), as well as eighteen known compounds, were isolated from the hot ethanol extract of the whole plant of Euphorbia humifusa Willd. The new structures were characterized by means of spectroscopic methods including 1D, 2D NMR and HRESIMS, and the known ones were established on the basis of comparing their NMR data with those of the corresponding compounds in the literature. In addition, cytotoxicity against selected cancer cell human gastric carcinoma (SGC‐7901) of compounds 1,3,4,6 were measured in vitro.     

Xanthone O‐Glycosides from the Roots of Pteris Multifida

Two new xanthone glycosides and six known compounds were isolated from the roots of Pteris multifida. Based on spectroscopic and chemical methods, the structures of the new compounds were elucidated as 1‐hydroxy‐4,7‐dimethoxy‐8‐(3‐methyl‐2‐butenyl)‐6‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐[β‐D‐glucopyranosyl‐(1→3)]‐β‐D‐glucopyranosylxanthone ( 1 ), and 1,3‐dihydroxy‐7‐methoxy‐8‐(3‐methyl‐2‐butenyl)‐6‐O‐α‐L‐rhamnopyranosyl‐(1 →2)‐[β‐D‐glucopyranosyl‐(1→3)]‐β‐D‐glucopyranosylxanthone ( 2 ), respectively.     

Prenylated Indole Alkaloid Derivatives from Marine Sediment‐Derived Fungus Penicillium paneum SD‐44

Three new prenylated indole alkaloids, including two β‐carbolines, penipalines A and B ( 1 and 2 , resp.), and one indole carbaldehyde derivative, penipaline C ( 3 ), as well as two known indole derived analogs, 4 and 5 , were isolated from the deep‐sea‐sediment derived fungus Penicillium paneum SD‐44 cultured in a 500‐l bioreactor. The structures of the new compounds were determined on the basis of 1D‐ and 2D‐NMR spectroscopy, as well as by high‐resolution mass spectrometry. The new compounds 2 and 3 showed potent cytotoxic activities against A‐549 and HCT‐116 cell lines.     

An Eco‐friendly Synthesis and Biological Screening of Fused Heterocyclic Compounds Containing a Thiophene Moiety via Gewald Reaction

5‐Amino‐3‐phenyl‐1‐(2,4,6‐trichlorophenyl)‐1H‐thieno[3,2‐c]pyrazole‐6‐carbonitrile ( 2 ) was designed and synthesized by one‐pot multicomponent reaction. Compound 2 was reacted with different reagents to obtain new condensed moieties with our thienopyrazole skeleton. The compounds were prepared by using environmentally benign techniques as microwave irradiation, ultrasonic irradiation, and ball‐milling. The structure of the prepared compounds was elucidated through spectroscopic methods. The new compounds were evaluated for their in vitro antibacterial and antifungal potentialities.     

Three New, 1‐Oxygenated ent‐8,9‐Secokaurane Diterpenes from Croton kongensis

Three new ent‐8,9‐secokaurane diterpenes, kongensins A–C ( 1 – 3 ), were isolated from the aerial parts of Croton kongensis, together with two known compounds, rabdoumbrosanin ( 4 ) and (7α,14β)‐7,14‐dihydroxy‐ent‐kaur‐16‐en‐15‐one ( 5 ). The structures of the new compounds were elucidated by HR‐MS as well as in‐depth 1D‐ and 2D‐NMR analyses. Compounds 1 – 3 showed an unusual oxygenation pattern, with an AcO or OH group at C(1), in combination with a Δ⁸⁽¹⁴⁾ unsaturation ( 1 ) or an 8,14‐epoxide function ( 2, 3 ).     

Six New Dammarane Triterpenoids from Viburnum cylindricum

One new dammarane triterpenoid, cylindrictone A ( 1 ), as well as five new nor‐dammarane triterpenoids cylindrictone B–F ( 2 – 6 ) were isolated from the leaves of Viburnum cylindrium, together with three known compounds 3β‐hydroxy‐hexanordammaran‐20‐one ( 7 ), 3α‐hydroxyoctanordammar‐12‐en‐17‐one ( 8 ), and neoalsogenin B ( 9 ). Their structures were identified by extensive NMR‐spectroscopic (especially 2D‐NMR) and mass‐spectrometric experiments, and the structure of 3 was further confirmed by a single‐crystal X‐ray analysis. The compounds exhibited no activity against human promyelocytic leukemia HL60 cell.     

Chemical Constituents of the Endophytic Fungus Phomopsis sp. A240 Isolated from Taxus chinensis var. mairei

A new sesquiterpene, eremophil‐9‐ene‐11,12,13‐triol ( 1 ), a new oxazole, 4‐(2‐hydroxyethyl)‐5‐methyloxazole ( 2 ), and the two known lactones, 5′‐hydroxyalternariol ( 3 ) and alternariol ( 4 ), were isolated from the extract of Phomopsis sp. A240, an endophytic fungus isolated from the bark of Taxus chinensis var. mairei. The structures of the isolated compounds were determined by analyses of their spectroscopic data, as well as by comparison with literature reports. The isolated compounds were evaluated for their cytotoxic and antioxidant activities.     

Two New Withanolides from Physalis peruviana

Two new perulactone‐type withanolides, named perulactone C ( 1 ) and perulactone D ( 2 ), together with four known compounds, perulactone ( 3 ), perulactone B ( 4 ), blumenol A, and (+)‐(S)‐dehydrovomifoliol, were isolated from the aerial parts of Physalis peruviana. The structures of the new compounds were elucidated on the basis of 1D‐ and 2D‐NMR experiments, including HMBC, HSQC, ¹H,¹H‐COSY, and ROESY, as well as HR‐MS.     

Habaenines A and B,Two New Norditerpenoid Alkaloids from Aconitum habaense

Two new norditerpenoid alkaloids, habaenine A and B ( 1 and 2 ), together with two known compounds, were isolated from Aconitum habaense. The structures of the new compounds were elucidated on the basis of spectral analyses as (1α,6α,16β)‐8‐(acetyloxy)‐20‐ethyl‐13‐hydroxy‐1,6,16‐trimethoxy‐4‐(methoxymethyl)‐19‐oxoaconitan‐14‐yl 4‐methoxybenzoate ( 1 ) and (1α,6α,16β)‐8‐(acetyloxy)‐13‐hydroxy‐1,6,16‐trimethoxy‐4‐(methoxymethyl)‐aconitan‐14‐yl 4‐methoxybenzoate ( 2 ).     

Constituents from Rubia Ustulata Diels and R. Yunnanensis Diels and Their Antiplatelet Aggregation Activity

A new anthraquinone glycoside, rubiayannone‐A ( 1 ), and a new coumarin, rubilatin‐A ( 2 ), together with twenty‐two known compounds were isolated and characterized from the roots of Rubia ustulata. A new anthraquinone, 2‐carbomethoxyanthraquinone ( 3 ), and rubiayannone‐A, 2‐formylanthraquinone were obtained from the roots of R. yunnanensis. The structures of those compounds were elucidated by spectroscopic methods. The antiplatelet aggregation activity of the isolated compounds 1, 4～6 were also discussed.     

Chemical Constituents of Ailanthus triphysa

Two new compounds,8(14),15-isopimaradiene-2α，３α，19-triol(1),and 6α，７β－dihydroxy-17(20)-cis-5α－pregna-16-one(2),together with four known copounds,a oxygenated rare phyllocladane,phyllocladan-16α，19-diol(3),kaempferol-3-0-β－Ｄ-galactopyranosied,kaempferol-3-0-α－Ｌ－rhamnopyranoside and scopoletin, were isolated from the leaves of Ailanthus tripysa.Structures of 1-3 were elucidated on the basis of spectroscopic data as compared with related compounds.     

A New Isofuranonaphthalenone and Benzopyrans from the Endophytic Fungus Nodulisporium sp. A4 from Aquilaria sinensis

A new isofuranonaphthalenone, (7R*,8S*)‐3,6,7,8‐tetrahydro‐4,7,8‐trihydroxynaphtho[2,3‐c]furan‐5(1H)‐one ( 1 ), and a new benzopyran, (2R*,4R*)‐3,4‐dihydro‐4‐methoxy‐2‐methyl‐2H‐1‐benzopyran‐5‐ol ( 2 ), together with four known related analogs, 3 – 6 , were isolated from the culture of Nodulisporium sp. A4, an endophytic fungus from the stem of Aquilaria sinensis (Lour.) Gilg . The structures of the isolated compounds were determined by extensive analysis of their spectroscopic data as well as by comparison with literature reports. The isolated compounds 1 – 6 were evaluated for their cytotoxic activities against the NCI‐H460 and SF‐268 tumor cell lines.     

Synthesis and Antimicrobial Evaluation of Novel Polyfused Heterocycles‐Based Quinolone

Syntheses of some new heterocyclic compounds incorporating quinolone moieties were achieved via reaction of 4‐hydroxy‐7‐methoxyquinolin‐2(1H)‐one ( 1 ) or 3‐bromo‐4‐hydroxy‐7‐methoxyquinolin‐2(1H)‐one ( 2 ) with binucleophilic reagents. The newly synthesized compounds were characterized by elemental analyses and spectral data (IR, ¹H‐NMR and mass spectra). The newly synthesized compounds were screened for their antibacterial activity against Gram‐positive bacteria (Bacillus thuringiensis) and Gram‐negative bacteria (Escherichia coli). The results showed clearly that compounds 1 and 3 are the more potent antibacterial agents against E. coli, compounds 4 , 5 , 6 and 8 , 9 , 10 , 11 , 12 , 13 exhibited moderate activities against E. coli strain, and compounds 7 and 11 exhibited weak activities compared with Gentamicin as a well known standard drug.     

Two New Sesquiterpenes from Euonymus alatus

Two new sesquiterpenes, 1 and 2 , as well as the five known compounds 3 – 7 , were isolated from the stems of Euonymus alatus. Compounds 2 – 7 have a β‐dihydroagarofuran skeleton. The structures of these compounds were elucidated mainly by spectroscopic methods (1D‐, 2D‐NMR, ESI‐MS, and HR‐ESI‐MS). We also report the X‐ray crystal structure of evonine ( 3 ) for the first time.