Antiproliferative Evaluation of Some 2‐[2‐(2‐Phenylethenyl)‐cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles: DFT and Molecular Docking Study

The 2‐[2‐(2‐phenylethenyl)cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles were synthesized from the reactions of 7‐benzylidenebicyclo[3.2.0]hept‐2‐en‐6‐ones with 2‐aminobenzenethiol. The antiproliferative activities of 2‐[2‐(2‐phenylethenyl)cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles were determined against C6 (rat brain tumor) and HeLa (human cervical carcinoma cells) cell lines using BrdU cell proliferation ELISA assay. Cisplatin and 5‐fluorouracil (5‐FU) were used as standards. The most active compound was 2‐{(1S,2S)‐2‐[(E)‐2‐(4‐methylphenyl)ethenyl]cyclopent‐3‐en‐1‐yl}‐1,3‐benzothiazole against C6 cell lines with IC₅₀=5.89 μm value (cisplatin, IC₅₀=14.46 μm and 5‐FU, IC₅₀=76.74 μm ). Furthermore, the most active compound was 2‐{(1S,2S)‐2‐[(E)‐2‐(2‐methoxyphenyl)ethenyl]cyclopent‐3‐en‐1‐yl}‐1,3‐benzothiazole against HeLa cell lines with IC₅₀=3.98 μm (cisplatin, IC₅₀=37.95 μm and 5‐FU, IC₅₀=46.32 μm ). Additionally, computational studies of related molecules were performed by using B3LYP/6‐31G+(d,p) level in the gas phase. Experimental IR and NMR data were compared with the calculated results and were found to be compatible with each other. Molecular electrostatic potential (MEP) maps of the most active 2‐{(1S,2S)‐2‐[(E)‐2‐(2‐methoxyphenyl)ethenyl]cyclopent‐3‐en‐1‐yl}‐1,3‐benzothiazole against HeLa and the most active 2‐{(1S,2S)‐2‐[(E)‐2‐(4‐methylphenyl)ethenyl]cyclopent‐3‐en‐1‐yl}‐1,3‐benzothiazole against C6 were investigated, aiming to determine the region that the molecule is biologically active. Biological activities of mentioned molecules were investigated with molecular docking analyses. The appropriate target protein (PDB codes: 1 M17 for the HeLa cells and 1JQH for the C6 cells) was used for 2‐{(1S,2S)‐2‐[(E)‐2‐(2‐methoxyphenyl)ethenyl]cyclopent‐3‐en‐1‐yl}‐1,3‐benzothiazole and 2‐{(1S,2S)‐2‐[(E)‐2‐(4‐methylphenyl)ethenyl]cyclopent‐3‐en‐1‐yl}‐1,3‐benzothiazole molecules exhibiting the highest biological activity against HeLa and C6 cells in the docking studies. As a result, it was determined that these molecules are the best candidates for the anticancer drug.     

Bioactive 9,11‐Secosteroids from Gorgonian Subergorgia suberosa Collected from the South China Sea

Five new 9,11‐secosteroids 1, 2 , and 4 – 6 , and seven known analogs, 3 and 7 – 12 , with the same steroid skeleton, (5αH)‐3β,6α,11‐trihydroxy‐9,11‐secocholest‐7‐en‐9‐one, were isolated from the South China Sea gorgonian Subergorgia suberosa. Among them, 2 / 3 and 4 / 5 are C(24)‐epimeric mixtures, and 6 / 7 is an (E)/(Z) mixture of (C(24)?C(28)). Their structures and relative configurations were elucidated by using comprehensive spectroscopic methods including NOESY spectra. The absolute configuration of the steroidal nucleus was established by the modified Mosher method applied to 10 and on the basis of a common biogenesis for all of these compounds. All isolated compounds, 1 – 12 , and five synthetic acetylated derivatives, 12a – 12e , were evaluated for their cytotoxicities in vitro. Compounds 4 / 5, 11, 12 , and 12b – 12d showed cytotoxic activities against K562 cell line with the IC₅₀ values ranging from 1.09 to 8.12 μM .     

Two New Pyrrolosesquiterpenes Produced by a Streptomyces Species

Two new pyrrolosesquiterpenes, 1 and 2 , were isolated from cultures of the soil actinomycete Streptomyces sp. Hd7–21. The structures of these compounds were established as (2Z,4E,9E)‐6,7,11‐trihydroxy‐3,7,11‐trimethyl‐1‐(1H‐pyrrol‐2‐yl)dodeca‐2,4,9‐trien‐1‐one ( 1 ) and (2Z,4E)‐5‐{3‐[(2E)‐4‐hydroxy‐4‐methylpent‐2‐en‐1‐yl]‐3‐methyloxiran‐2‐yl}‐3‐methyl‐1‐(1H‐pyrrol‐2‐yl)penta‐2,4‐dien‐1‐one ( 2 ) by extensive spectroscopic analyses including MS, and 1D‐ and 2D‐NMR data. Their cytotoxic activities against a panel of human cancer cell lines were evaluated.     

Four New Tirucallane Triterpenoids from the Fruits of Melia azedarach and Their Cytotoxic Activities

Four new tirucallane triterpenoids, (21S,23R,24R)‐21,23‐epoxy‐21,24‐dihydroxy‐25‐methoxytirucall‐7‐en‐3‐one ( 2 ), (3S,21S,23R,24S)‐21,23‐epoxy‐21,25‐dimethoxytirucall‐7‐ene‐3,24‐diol ( 8 ), (21S,23R,24R)‐21,23‐epoxy‐24‐hydroxy‐21‐methoxytirucalla‐7,25‐dien‐3‐one ( 11 ), and (21S,23R,24R)‐21,23‐epoxy‐21,24‐dihydroxytirucalla‐7,25‐dien‐3‐one ( 12 ), along with 16 known analogues, 1 , 3  –  7 , 9  –  10 , and 13  –  20 , were isolated from the fruits of Melia azedarach. Their structures were elucidated by spectroscopic methods including 1D‐ and 2D‐NMR techniques and mass spectrometry. These compounds were evaluated for their cytotoxicities against HepG2 (liver), SGC7901 (stomach), K562 (leukemia), and HL60 (leukemia) cancer cell lines. Compound 20 exhibited potent cytotoxicity against HepG2 and SGC7901 cancer cells with the IC₅₀ values of 6.9 and 6.9 μm , respectively.     

Isolation of Ceramides from Tagetes patula L. Yellow Flowers and Nematicidal Activity of the Fractions and Pure Compounds against Cyst Nematode,Heterodera zeae

Investigation of yellow flower extract of Tagetes patula L. led to the identification of an aggregate of five phytoceramides. Among them, (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]icosanamide, (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]heneicosanamide, (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]docosanamide, and (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]tricosanamide were identified as new compounds and termed as tagetceramides, whereas (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]tetracosanamide was a known ceramide. A steroid (β‐sitosterol glucoside) was also isolated from the subsequent fraction. The structures of these compounds were determined on the basis of spectroscopic analyses, as well as chemical method. Several other compounds were also identified by GC/MS analysis. The fractions and some commercial products, a ceramide HFA, β‐sitosterol, and stigmasterol were evaluated against an economically important cyst nematode, Heterodera zeae. Ceramide HFA showed 100 % mortality, whereas, β‐sitosterol and stigmasterol were 40–50 % active, at 1 % concentration after 24 h of exposure time, while β‐sitosterol glucoside revealed no activity against the nematode.     

Terpenes from the Soft Corals Litophyton arboreum and Sarcophyton ehrenbergi

The new cembrane diterpene (3E,11E)‐cembra‐3,8(19),11,15‐tetraene‐7α‐ol ( 1 ), nephthenol ( 2 ), and all‐trans‐peridinin ( 3 ) have been isolated from the soft coral Litophyton arboreum. The tetraterpene 3 , (+)‐7,8‐epoxy‐7,8‐dihydrocembrene C ( 4 ), emblide ( 5 ), sarcophytoxide ( 6 ), sarcoglaucol‐16‐one ( 7 ), guajacophine ( 8 ), and 1,4‐peroxymuurol‐5‐ene ( 9 ) have been obtained from the soft coral Sarcophyton ehrenbergi. The compounds were characterized primarily by NMR spectroscopy. Some of the terpenes were tested for their antiproliferative activity against the cell lines HUVEC and K‐562 and for cytotoxicity against the cell line HeLa, and they showed moderate activities.     

Chemical constituents of Papulaspora immersa, an endophyte from Smallanthus sonchifolius (Asteraceae), and their cytotoxic activity

Papulaspora immersa H. H. Hotson was isolated from roots and leaves of Smallanthus sonchifolius (Poepp. and Endl. ) H. Rob. (Asteraceae), traditionally known as Yacon. The fungus was cultured in rice, and, from the AcOEt fraction, 14 compounds were isolated. Among them, (22E,24R)‐8,14‐epoxyergosta‐4,22‐diene‐3,6‐dione ( 4 ), 2,3‐epoxy‐1,2,3,4‐tetrahydronaphthalene‐c‐1,c‐4,8‐triol ( 10 ), and the chromone papulasporin ( 13 ) were new secondary metabolites. The spectral data of the known natural products were compared with the literature data, and their structures were established as the (24R)‐stigmast‐4‐en‐3‐one ( 1 ), 24‐methylenecycloartan‐3β‐ol ( 2 ), (22E,24R)‐ergosta‐4,6,8(14),22‐tetraen‐3‐one ( 3 ), (?)‐(3R,4R)‐4‐hydroxymellein ( 5 ), (?)‐(3R)‐5‐hydroxymellein ( 6 ), 6,8‐dihydroxy‐3‐methylisocoumarin ( 7 ), (?)‐(4S)‐4,8‐dihydroxy‐α‐tetralone ( 8 ), naphthalene‐1,8‐diol ( 9 ), 6,7,8‐trihydroxy‐3‐methylisocoumarin ( 11 ), 7‐hydroxy‐2,5‐dimethylchromone ( 12 ), and tyrosol ( 14 ). Compound 4 showed the highest cytotoxic activity against the human tumor cell lines MDA‐MB435 (melanoma), HCT‐8 (colon), SF295 (glioblastoma), and HL‐60 (promyelocytic leukemia), with IC₅₀ values of 3.3, 14.7, 5.0 and 1.6 μM , respectively. Strong synergistic effects were also observed with compound 5 and some of the isolated steroidal compounds.     

Four New Chromone Derivatives from Colletotrichum gloeosporioides

Four previously unreported chromones, 5‐hydroxy‐2‐(hydroxymethyl)‐8‐methoxy‐4H‐chromen‐4‐one ( 1 ), (5R,7S)‐5,7‐dihydroxy‐2‐propyl‐5,6,7,8‐tetrahydro‐4H‐chromen‐4‐one ( 2 ), (5R,7S)‐5,7‐dihydroxy‐2‐methyl‐5,6,7,8‐tetrahydro‐4H‐chromen‐4‐one ( 3 ), and (5R,7S)‐5,7‐dihydroxy‐2‐[(E)‐prop‐1‐en‐1‐yl]‐5,6,7,8‐tetrahydro‐4H‐chromen‐4‐one ( 4 ), as well as one known analogue 5‐hydroxy‐2‐methyl‐4H‐chromen‐4‐one ( 5 ) were isolated from the fermentation broth of the endophytic fungus Colletotrichum gloeosporioides derived from the mangrove Ceriops tagal. Their structures were elucidated based on extensive spectroscopic analyses. The absolute configurations of 2 – 4 were determined by comparison the experimental and calculated electronic circular dichroism (ECD) spectra. Compound 2 showed cytotoxic activity against A549 cell line with the IC₅₀ value of 0.094 mm .     

Diterpenoids from Acanthopanax brachypus Harms

Four diterpenoids, including two new ones, namely noracanthopanin A ( 1 ) and acanthopanolide B ( 2 ), and two known ones, ent‐pimara‐9(11),15‐dien‐19‐oic acid ( 3 ) and ent‐kaur‐16‐en‐19‐oic acid ( 4 ), were isolated from the stem bark of Acanthopanax brachypus Harms . Their structures were elucidated by physicochemical and spectroscopic analyses. Compound 1 and 2 exhibited moderate cytotoxicities against HO‐8910 cells with IC₅₀ values of 65.21±0.23 and 31.43±1.01 μg/ml, respectively, and 2 showed selective weak cytotoxicity against SMMC‐7721 cells (IC₅₀ 89.67±2.54 μg/ml).     

Cytotoxic Compounds from the Leaves of Garcinia polyantha

A new compound, named banganxanthone C (=12‐(1,1‐dimethylprop‐2‐en‐1‐yl)‐5,10‐dihydroxy‐9‐methoxy‐2‐methyl‐2‐(4‐methylpent‐3‐en‐1‐yl)‐2H,6H‐pyrano[3,2‐b]xanthen‐6‐one; 4 ), together with five known compounds, were isolated from the leaves of Garcinia polyantha. The structures of the compounds were elucidated on the basis of 1D‐ and 2D‐NMR spectroscopy. Among the known compounds, two were xanthones, one was a pentacyclic triterpene, one sterol, and one benzophenone derivative. Isoxanthochymol ( 2 ) and 4‐[(2E)‐3,7‐dimethylocta‐2,6‐dien‐1‐yl]‐1,5,8‐trihydroxy‐3‐methoxy‐9H‐xanthen‐9‐one ( 3 ) exhibited significant antiproliferative activity against the leukemia cell line TPH‐1 with IC₅₀ inhibition values of 1.5 and 2.8 μg/ml, respectively. The cytotoxic activity was found to be related to apoptosis induction.     

Novel Neolignan from Penthorum chinense

A new neolignan （7＇E）-2＇,4,8-trihydroxy-3-methoxy-2,4＇-epoxy-8,5＇-neolign-7＇-en-7-one （1） was isolated from the whole plants of Penthorum chinense Pursh, along with Iupeol （2）, betulinic acid （3）, glyceryl monopalmitate （4）, β-sitosterol （5）, palmitic acid （5）, ursolic acid （7）, 2β,3β,23-trihydroxy-urs-12-ene-28-oic acid （8）, glyceryl monolaurate （9）, scopoletin （10）, （-）syringaresinol （11）, 9,9＇-O-diferuIoyl-（-）-secoisolariciresionl （12）, pinocembrin （13）, apigenin （14）, kaempferol （15）, Iuteolin （16）, β-daucosterol （17）, quercetin （18）, 1-O-（β-D-glucopyranosyl）-（2S, 2＇R, 3R,4E,8E）-2-（2＇-hydroxyhexadecanoy- lamino）-4,8-octdecadiene-1,3-diol （19）, gallic acid （20）, pinocembrin-7-O-β-D-glucoside （21）, and quercetin-3-O-β-D- glucoside （22）. The structures of these compounds were elucidated on the basis of chemical and spectral evidence.     

Diterpenoids from Wedelia prostrata and Their Derivatives and Cytotoxic Activities

One new ent‐kaurane diterpenoid, 11β,16α‐dihydroxy‐ent‐kauran‐19‐oic acid ( 1 ), together with eight known analogues 2 – 9 were isolated from the aerial parts of Wedelia prostrata. One of the acidic diterpenoids, kaurenoic acid ( 3 ), was converted to seven derivatives, 10 – 16 . All compounds were evaluated for their cytotoxic activity in vitro against human leukemia (K562), liver (HepG‐2), and stomach (SGC‐7901) cancer cell lines. Only four kaurenoic acid derivatives, 13 – 16 , with 15‐keto and substitutions at C(19) position, exhibited notable cytotoxic activities on these tumor cell lines with IC₅₀ value ranging from 0.05 to 3.71 μm . Compounds 10 – 12 , with oxime on C(15) showed moderate inhibitory effects and compounds 1 – 9 showed no cytotoxicities on them. Structure–activity relationships were also discussed based on the experimental data obtained. The known derivative, 15‐oxokaurenoic acid 4‐piperdin‐1‐ylbutyl ester ( 17 ), induced typical apoptotic cell death in colon SW480 cells upon evaluation of the apoptosis‐inducing activity by flow‐cytometric analysis.     

Chemical Constituents of the Rare Cliff Plant Oresitrophe rupifraga and Their Antineuroinflammatory Activity

Four new ( 1 – 4 ) and thirteen known ( 5 – 17 ) compounds were isolated from a rare cliff plant, Oresitrophe rupifraga. Based on spectroscopic evidence, the new structures were established to be [(2S,3R,4R)‐4‐(4‐methoxybenzyl)‐2‐(4‐methoxyphenyl)‐tetrahydrofuran‐3‐yl]methanol ( 1 ), (3α)‐23‐(acetyloxy)‐3‐hydroxyolean‐12‐en‐29‐oic acid ( 2 ), 3α,23‐(isopropylidenedioxy)olean‐12‐en‐29‐oic acid ( 3 , artifact of isolation), and (3β,15β)‐3‐hydroxycholest‐5‐en‐15‐yl β‐d ‐glucopyranoside ( 4 ), respectively. Among the isolates, compounds 1 , 4 , epieudesmin ( 7 ), and 1‐O‐(9Z,12Z,15Z‐octadecatrienoyl)glycerol ( 17 ) were found to show significant antineuroinflammatory effects by inhibiting the NO production in lipopolysaccharide (LPS)‐stimulated murine BV‐2 microglial cells, with IC₅₀ values of 7.21, 9.39, 4.96, and 8.51 μm , respectively.     

Cytotoxic and Anti‐inflammatory Sesquiterpenes from Ainsliaea henryi

Three new sesquiterpenoids, 4α‐hydroxyeudesm‐11(13)‐en‐12‐yl 3‐methylbutanoate ( 1 ), diaspanolide E ( 2 ), and (13α)‐germacra‐1(10),4‐dien‐12,8α‐olid‐15‐oic acid ( 3 ), along with eight known sesquiterpenoids ( 4 – 11 ), were isolated from the aerial parts of Ainsliaea henryi. The chemical structures of compounds 1 – 3 were elucidated by spectroscopic analysis (1D‐, 2D‐NMR, MS and HR/MS). All isolates were evaluated for their inhibitory activities against nitric oxide (NO) production in lipopolysaccharide‐induced RAW264.7 macrophage cells. Compound 10 exhibited significantly inhibition against NO release with an IC₅₀ value of 6.54 ± 0.16 μm . Also, all isolated compounds were tested for cytotoxicity against three human tumor cell lines A549, MGC803, and HCT116, among which compound 5 significantly inhibited the proliferation of MGC803 cell lines with an IC₅₀ value of 2.2 ± 0.2 μm .     

Synthesis and Antifungal Activities of Trichodermin Derivatives as Fungicides on Rice

Twenty new trichodermin derivatives, 2a – 5 , containing alkoxy, acyloxy, and Br groups in 4‐, 8‐, 9‐, 10‐ and 16‐positions were synthesized and characterized. The antifungal activities of the new compounds against rice false smut (Ustilaginoidea virens), rice sheath blight (Rhizoctonia solani), and rice blast (Magnaporthe grisea) were evaluated. The results of bioassays indicated that the antifungal activities were particularly susceptible to changes at 4‐, 8‐, and 16‐positions, but low to changes at 9‐ and 10‐positions. Most of these target compounds exhibited good antifungal activities at the concentration of 50 mg l^?1. Compound 4 (9‐formyltrichodermin; EC₅₀ 0.80 mg l^?1) with an CHO group at 9‐position displayed nearly the same level of antifungal activity against Ustilaginoidea virens as the commercial fungicide prochloraz (EC₅₀ 0.82 mg l^?1), while compound 3f ((8R)‐8‐{[(E)‐3‐phenylprop‐2‐enoyl]oxy}trichodermin; EC₅₀ 3.58 and 0.74 mg l^?1) with a cinnamyloxy group at C(8) exhibited much higher antifungal activities against Rhizoctonia solani and Magnaporthe grisea than the commercial fungicides prochloraz (EC₅₀ 0.96 mg l^?1) and propiconazole (EC₅₀ 5.92 mg l^?1), respectively. These data reveal that compounds 3f and 4 possess high antifungal activities and may serve as lead compounds for the development of fungicides in the future.     

Two New Steroids from an Endophytic Fungus Phomopsis sp.

Two new steroids, (14β,22E)‐9,14‐dihydroxyergosta‐4,7,22‐triene‐3,6‐dione ( 1 ) and (5α,6β,15β,22E)‐6‐ethoxy‐5,15‐dihydroxyergosta‐7,22‐dien‐3‐one ( 2 ), together with three known steroids, calvasterols A and B ( 3 and 4 , resp.), and ganodermaside D ( 5 ), were isolated from the culture broth of an endophytic fungus Phomopsis sp. isolated from Aconitum carmichaeli. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and their inhibitory activities against six pathogenic fungi were evaluated. Most of the compounds showed moderate or weak antifungal activities in a broth‐microdilution assay.     

Structural Modification of Stilbenoids from Acanthopanax leucorrhizus and Their Cytotoxic Activity

A new cis‐stilbenoid, 1,9‐dihydroxy‐10‐methoxy‐6H‐dibenzo[b,f]oxocin‐6‐one ( 2 ) was isolated from the AcOEt extract of the stem barks of Acanthopanax leucorrhizus, along with three known stilbenoids, 9‐hydroxy‐10‐methoxy‐6H‐dibenzo[b,f]oxocin‐6‐one ( 1 ), 5‐O‐methyl‐(E)‐resveratrol 3‐O‐β‐d ‐glucopyranoside ( 3 ), and (E)‐resveratrol 3‐O‐β‐d ‐xylopyranoside ( 4 ). Two derivatives ( 2a and 2b ) were synthesized by the structural modification of compound 2, which exhibited certain cytotoxic activities against HT‐29 and HeLa cell lines in vitro. All compounds were structurally characterized by comprehensive analysis of their spectroscopic data and comparison with literature information, and evaluated for their cytotoxic activities against three human tumor cell lines (HL‐60, HT‐29, and HeLa) by the standard MTT assay in vitro. The results showed that derivatives 2a and 2b exhibited strong activities than compounds 2 against HT‐29 and HeLa cell lines.     

Triterpenoids and Flavonoids from the Leaves of Astragalus membranaceus and Their Inhibitory Effects on Nitric Oxide Production

Four new cycloartane triterpenes, named huangqiyegenins V and VI and huangqiyenins K and L ( 1 – 4 , resp.), together with nine known triterpenoids, 5 – 13 , and eight flavonoids, 14 – 21 , were isolated from a 70%‐EtOH extract of Astragalus membranaceus leaves. The structures of the new compounds were elucidated by detailed spectroscopic analyses, and the compounds were identified as (9β,11α,16β,20R,24S)‐11,16,25‐trihydroxy‐20,24‐epoxy‐9,19‐cyclolanostane‐3,6‐dione ( 1 ), (9β,16β,24S)‐16,24,25‐trihydroxy‐9,19‐cyclolanostane‐3,6‐dione ( 2 ), (3β,6α,9β,16β,20R,24R)‐16,25‐dihydroxy‐3‐(β‐D ‐xylopyranosyloxy)‐20,24‐epoxy‐9,19‐cyclolanostan‐6‐yl acetate ( 3 ), and (3β,6α,9β,16β,24E)‐26‐(β‐D ‐glucopyranosyloxy)‐16‐hydroxy‐3‐(β‐D ‐xylopyranosyloxy)‐9,19‐cyclolanost‐24‐en‐6‐yl acetate ( 4 ). All isolated compounds were evaluated for their inhibitory activities against LPS‐induced NO production in RAW264.7 macrophage cells. Compounds 1 – 3, 14, 15 , and 18 exhibited strong inhibition on LPS‐induced NO release by macrophages with IC₅₀ values of 14.4–27.1 μM .     

Sesquiterpenoids and Diterpenoids from Chloranthus anhuiensis

A phytochemical investigation of the roots of Chloranthus anhuiensis afforded three new sesquiterpene lactones, chloraniolide A ( 1 ), (3R)‐3‐hydroxyatractylenolide III ( 2 ), and 8β‐hydroxy‐1‐oxoeudesma‐3,7(11)‐dien‐12,8α‐olide ( 3 ), and two new diterpenoids, (12R,13E)‐15‐(acetoxy)‐12‐hydroxylabda‐8(20),13‐dien‐19‐oic acid ( 4 ) and (12S,13E)‐15‐(acetoxy)‐12‐dihydroxylabda‐8(20),13‐dien‐19‐oic acid ( 5 ), as well as 17 known sesquiterpenoid and diterpenoid compounds. Their structures were established on the basis of 1D‐ and 2D‐NMR, and other spectroscopic analyses.     

A New Anti‐Inflammatory Alkaloid from Roots of Heracleum dissectum

Using various chromatographic methods, a new piperidinone alkaloid, (3S)‐3‐{4‐[(1E)‐3‐hydroxyprop‐1‐en‐1‐yl]‐2‐methoxyphenoxy}piperidin‐2‐one ( 1 ), together with 10 known compounds, bergapten ( 2 ), xanthotoxol ( 3 ), isopimpinellin ( 4 ), isobergapten ( 5 ), heratomol‐6‐O‐β‐d ‐glucopyranoside ( 6 ), scopoletin ( 7 ), apterin ( 8 ), 3‐methoxy‐4‐β‐d ‐glucopyranosyloxypropiophenone, (praeroside; 9 ), tachioside ( 10 ) and coniferin ( 11 ), were isolated from roots of Heracleum dissectum Ledeb . Their structures were elucidated on the basis of physicochemical properties and the detailed interpretation of various spectroscopic data. All the isolated compounds were screened for anti‐inflammatory activity in vitro. As the results, compound 1 and 8 showed significantly inhibitory activity on nitric oxide production in RAW264.7 cells.