Two New Eudesmanoildes from Sonchus transcaspicus

Two new sesquiterpene lactone glycosides were isolated from the whole plant ofSonchus transcaspicus. Their structures were elucidated as 1β--O-β-D-glucopyranosy-5α, 6βH-eudesma-3-en-12, 6αt-olide and 1β--O-β-D-glucopyranosy-15-O-(p-hydroxylphenylacetate)-5α，6β H-eudesma-3, ll(13)-dien-12, 6α-olide by spectral methods (HRMS, 1D and 2D NMR).     

Uncommon Sesquiterpenoids and New Triterpenoids from Jatropha neopauciflora (Euphorbiaceae)

Eight new terpenoids ( 1 – 8 ) were isolated from the bark of Jatropha neopauciflora, together with eight known compounds. The new isolates include the sesquiterpenoids (1R,2R)‐diacetoxycycloax‐4(15)‐ene ( 1 ); (1R,2R)‐dihydroxycycloax‐4(15)‐ene ( 2 ), (2R)‐δ‐cadin‐4‐ene‐2,10‐diol ( 3 ), (2R)‐δ‐cadina‐4,9‐dien‐2‐ol ( 4 ), (1R,2R)‐dihydroxyisodauc‐4‐en‐14‐ol ( 5 ) and its acetonide 6 (artifact), as well as the two triterpenoids (3β,16β)‐16‐hydroxylup‐20(29)‐en‐3‐yl (E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoate ( 7 ) and (3β,16β)‐16‐hydroxyolean‐18‐en‐3‐yl (E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoate ( 8 ). The structures of these compounds were established by extensive 1D‐ and 2D‐NMR spectroscopic methods, and their absolute configurations were determined by circular‐dichroism (CD) experiments, and by X‐ray crystallographic analysis (compound 7 ; Fig. 3). A plausible biosynthesis of the sesquiterpenoids 1 – 5 is proposed (Scheme), starting from (?)‐germacrene D as the common biogenetic precursor.     

Sesquiterpenoids and Lactone Derivatives from Ligularia dentata

Seven new compounds were isolated from the roots of Ligularia dentata, including five bisabolane‐type sesquiterpenoids (bisabolane=1‐(1,5‐dimethylhexyl)‐4‐methylcyclohexane), namely (8β,10α)‐8‐(angeloyloxy)‐5,10‐epoxybisabola‐1,3,5,7(14)‐tetraene‐2,4,11‐triol ( 1 ), (8β,10α)‐8‐(angeloyloxy)‐5,10‐epoxythiazolo[5,4‐a]bisabola‐1,3,5,7(14)‐tetraene‐4,11‐diol ( 2 ), (1α,2α,3β,5α,6β)‐1,5,8‐tris(angeloyloxy)‐10,11‐epoxy‐2,3‐dihydroxybisabol‐7(14)‐en‐4‐one ( 3 ), (1α,2α,3β,5α,6β)‐2,5,8‐tris(angeloyloxy)‐10,11‐epoxy‐1,3‐dihydroxybisabol‐7(14)‐en‐4‐one ( 4 ), and (1α,2β,3β,5α,6β)‐1,8‐bis(angeloyloxy)‐2,3‐epoxy‐5,10‐dihydroxy‐11‐methoxybisabol‐7(14)‐en‐4‐one ( 5 ) (angeloyloxy=[(2Z)‐2‐methyl‐1‐oxobut‐2‐enyl]oxy), and two lactone derivatives, (2α,3β,5α)‐2‐(acetyloxy)‐9‐methoxy‐5‐(methoxycarbonyl)‐2,3‐dimethylheptano‐5‐lactone ( 6 ), and (2β,4β)‐2‐ethyl‐5‐hydroxy‐5‐(methoxycarbonyl)‐4,5‐dimethylpentano‐4‐lactone ( 7 ) (α/β denote relative configurations), together with (2E,4R,5S)‐2‐ethylidene‐5‐(methoxycarbonyl)‐4‐methylhexano‐5‐lactone ( 8 ), a known synthetic compound. Compound 2 is the first sesquiterpenoid derivative containing the uncommon benzothiazole moiety. The structures of 1 – 8 were established by spectroscopic methods, especially 2D‐NMR and MS analyses.     

Three New Sesquiterpenoids from Chrysanthemum indicum L.

Phytochemical investigation of the flowers of Chrysanthemum indicum L. led to the isolation of three new sesquiterpenoids, indicumolide A ( 1 ), indicumolide B ( 2 ), and indicumolide C ( 3 ). Their structures were elucidated by various spectroscopic methods.     

New Sesquiterpenoids from Artemisia anomala

One new guaianolide, anomalactone A ( 1 ), and one new norcadinane sesquiterpene, anomallenodiol ( 2 ), along with two germacranolides, anomalactones B and C ( 3 and 4 , resp.), were isolated from the aerial part of Artemisia anomala S. Moore . Their structures were determined on the basis of extensive spectroscopic analyses.     

New Patchoulol‐Type Sesquiterpenoids from Pogostemon cablin

Four new patchoulol derivatives, 8α,9α‐dihydroxypatchoulol ( 1 ), 3α,8α‐dihydroxypatchoulol ( 2 ), 6α‐hydroxypatchoulol ( 3 ), and 2β,12‐dihydroxypatchoulol ( 4 ), were isolated from the aerial part of Pogostemon cablin (Labiatae), together with nine known compounds, sesquiterpenoids 5 – 8 and flavonoids 9 – 13 . Their structures were elucidated by detailed spectroscopic analysis, using 1D‐ and 2D‐NMR techniques.     

Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an Aquilaria Plant

Nine new sesquiterpenoids (1–9) were isolated from ethyl ether extract of agarwood originated from Aquilaria sp., including three novel sesquiterpenoids (1–3) derived from zizaane, together with six zizaane-type sesquiterpenoids (4–9). All structures were unambiguously elucidated based on 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of sesquiterpenoids was determined by comparison of the experimental and computed ECD spectra. In vitro anti-inflammatory assessment showed that compound 9 exhibited inhibition of NO production in LPS-stimulated RAW264.7 cells with an IC₅₀ value of 62.22 ± 1.27 μM.     

Sesquiterpene and Aristolochic Acid Derivatives from Thottea hainanensis

One new sesquiterpene named thotteodiol ( 1 ) with a novel skeleton and one new derivative of aristolochic acid named 7‐hydroxyaristolochic acid III methyl ester ( 2 ), together with 20 known compounds, were isolated from the stems and roots of Thottea hainanensis. Their structures were determined by spectroscopic methods.     

Eudesmanolides and Guaianolides from Carpesium triste

A new eudesmanolide, 1‐oxo‐11αH‐eudesma‐2,4(14)‐dien‐12,8β‐olide ( 1 ), and four new guaianolides, 9β,10β‐epoxy‐4α‐hydroxy‐1βH,11αH‐guaian‐12,8α‐olide ( 2 ), 9β,10β‐epoxy‐4α‐hydroxy‐1βH,11βH‐guaian‐12,8α‐olide ( 3 ), 4α,9α‐dihydroxy‐1βH,11αH‐guai‐10(14)‐en‐12,8α‐olide ( 4 ), and 4α,9α‐dihydroxy‐1βH,11βH‐guai‐10(14)‐en‐12,8α‐olide ( 5 ), together with one known eudesmanolide and two known germacranolides, were isolated from the whole plants of Carpesium triste. Their structures and relative configurations were elucidated on the basis of spectroscopic methods, including 2D‐NMR techniques.     

Neolignans and Caffeoyl Derivatives from Selaginella moellendorffii

Ten new phenolic compounds including the six neolignans 1 – 3 and 6 – 8 and four caffeoyl derivatives, i.e., myo‐inositol 1‐caffeate ( 9 ), myo‐inositol 6‐caffeate ( 10 ), myo‐inositol 5‐caffeate ( 11 ), and paucine 3′‐β‐D ‐glucopyranoside ( 12 ) were isolated from the whole plants of Selaginella moellendorffii (caffeic acid=3‐(3,4‐dihydroxyphenyl)prop‐2‐enoic acid). Their structures were established by spectroscopic and chemical methods.     

Cadinene Derivatives from Eupatorium adenophorum

A new norsesquiterpene named eupatorone (= (4S,4aR,6R)‐1‐acetyl‐6‐(acetyloxy)‐4,4a,5,6‐tetrahydro‐4,7‐dimethylnaphthalen‐2(3H)‐one; 1 ) and a new sesquiterpene derivative named 2‐deoxo‐2‐(acetyloxy)‐9‐oxoageraphorone (= (1R,4S,4aR,6R,8aS)‐6‐(acetyloxy)‐3,4,4a,5,6,8a‐hexahydro‐4,7‐dimethyl‐1‐(1‐methylethyl)naphthalen‐2(1H)‐one; 2 ), together with the five known cadinene derivatives 3 – 7 were isolated from the flower of Eupatorium adenophorum (Spreng. ). Their structures were established by extensive NMR experiments, including 1D and 2D NMR.     

Benzofuran Derivatives from Gerbera saxatilis

Three new substituted 2,3‐dihydro‐1‐benzofuran derivatives, compounds 1 – 3 , were isolated from two extracts of Gerbera saxatilis, together with twelve known constituents. The structures of the new compounds were established by means of detailed spectroscopic analysis and by comparison of analytical data with those reported for structurally related compounds.     

Chlorosulfenylated Carbonic Acid Derivatives

The present article deals first with the synthesis of chlorocarbonylsulfenyl chloride and its imino analogs. The chemical behavior of these bifunctional compounds is illustrated for selected examples. Special attention is given to the syntheses of five-membered heterocycles containing sulfur, oxygen, and/or nitrogen.     

2,6-吡啶二甲酰双吡唑衍生物的合成

合成了4个吡唑及其衍生物,其结构经元素分析,IR,1^HNMR和^13CNMR等表征。     

Sesquiterpenoids and norsesquiterpenoids from three liverworts

Six new sesquiterpenoids and two new norsesquiterpenoids were isolated from the essential oils of three liverworts. The isolated compounds include (+)-eudesma-4,11-dien-8α-ol from the liverwort Diplophyllum albicans, (−)-4β,5β-diacetoxygymnomitr-3(15)-ene, (+)-5β-acetoxygymnomitr-3(15)-ene, (−)-15-acetoxygymnomitr-3-ene, (−)-3β,15β-epoxy-4β-acetoxygymnomitrane, and (−)-3α,15α-epoxy-4β-acetoxygymnomitrane from Marsupella emarginata, and (+)-1,2,3,6-tetrahydro-1,4-dimethylazulene and (−)-2,3,3a,4,5,6-hexahydro-1,4-dimethylazulen-4-ol from Barbilophozia floerkei. These compounds were isolated by a combination of different chromatographic techniques, and their structures were determined by extensive spectroscopic studies (MS, ¹H, ¹³C, and 2D NMR) and chemical transformations using enantioselective GC.     

Novel Chromone Derivatives from Marine Fungus Aspergillus versicolor Isolated from the Sponge Xestospongia exigua

In the continuation of our research for the bioactive secondary metabolites from the sponge-associated fungi, the bioassay guiding fractionation led to the isolation of six new secondary metabolites with unusual skeleton based on chromone ring system from the inoculated fungus Aspergillus versicolor, that had been isolated from fresh samples of marine sponge Xestospongia exigua, collected along coast line of Bali, Indonesia in 1997. The basic skeleton of those compounds possessed an oxohexacy…     

Eremophilane Sesquiterpenoids from Ligularia fischeri

A novel eremophilane dimer, named as fischelactone, and a new sesquiterpene lactam, eremophila‐1(10),7(11),8‐triene‐12,8‐lactam, along with ten known compounds, were isolated from the roots of Ligularia fischeri. Their structures were established by means of spectroscopic analyses (EI‐MS, HR‐ESI‐MS, IR, and 1D‐ and 2D‐NMR data) and X‐ray diffraction study.     

Four New Gallate Derivatives from Wine-Processed Corni Fructus and Their Anti-Inflammatory Activities

Four new gallate derivatives—ornusgallate A, ent-cornusgallate A, cornusgallate B and C (1a, 1b, 2, 3)—were isolated from the wine-processed fruit of Cornus officinalis. Among them, 1a and 1b are new natural compounds with novel skeletons. Their chemical structures were elucidated by comprehensive spectroscopy methods including NMR, IR, HRESIMS, UV, ECD spectra and single-crystal X-ray diffraction analysis. The in vitro anti-inflammatory activities of all compounds were assayed in RAW 264.7 cells by assessing LPS-induced NO production. As the result, all compounds exhibited anti-inflammatory activities at attested concentrations. Among the tested compounds, compound 2 exhibited the strongest anti- inflammatory activity.