Hypenol,a New Lignan from Hypenia salzmannii

A new lignan, (?)‐secoisolariciresin‐9‐yl 6‐O‐p‐coumaroyl‐β‐D ‐glucopyranoside ( 1 ), named hypenol, along with eleven known compounds, i.e., hyperin, rosmarinic acid, methyl rosmarinate, a mixture of the triterpenes betulinic acid, ursolic acid, and oleanolic acid, glycosylated β‐sitosterol, a mixture of the flavanones sakuranetin and isosakuranetin, hinokinin, and β‐peltatin A dimethyl ether were isolated from the EtOH extract of the leaves of Hypenia salzmannii (Benth. ) Harley . The structures of the compounds were elucidated based on the analysis of spectral data, including MS, 1D‐ and 2D‐NMR, and comparison with data in the literature.     

A New 30‐Noroleanane Saponin from Wedelia chinensis

A novel 30‐nortriterpenoid saponin, (3β)‐3‐hydroxy‐30‐noroleana‐12,20(29)‐dien‐28‐oic acid 3‐(β‐D ‐glucopyranosiduronic acid 6‐methyl ester) ( 1 ), and a known compound, (3β)‐oleanolic acid 3‐(β‐D ‐glucopyranosiduronic acid 6‐methyl ester) ( 2 ), were isolated from the aerial parts of Wedelia chinensis. The structures were established by their spectral data including ¹H‐ and ¹³C‐NMR, ¹H,¹H‐COSY, HMBC, HSQC, NOESY, and HR‐FAB‐MS data.     

A New p‐Terphenyl Derivative from the Mushroom Thelephora vialis

One novel p‐terphenyl compound, named vialisyl A ( 1 ), was isolated from the fruiting bodies of Thelephora vialis, together with six known compounds, ganbajunin B ( 2 ), phenylacetic acid ( 3 ), a mixture of ganbajunins D ( 4 ) and E ( 5 ), and vialinins A ( 6 ) and B ( 7 ). Their structures were established by extensive analysis of spectroscopic data (including ¹H‐ and ¹³C‐NMR, HSQC, HMBC, 2D‐INADEQUATE) as well as by comparison with literature reports.     

Beilschmiedic Acids F and G,Further Endiandric Acid Derivatives from Beilschmiedia anacardioides

Two new endiandric acid derivatives, beilschmiedic acid F ( 1 ) and beilschmiedic acid G ( 2 ), together with three known constituents, beilschmiedic acid A, beilschmiedic acid C, and sitosterol 3‐β‐D ‐glucopyranoside, were isolated from the stem bark of Beilschmiedia anacardioides. Their structures were elucidated mainly by using a combination of 1D‐ and 2D‐NMR techniques. The structure and relative configuration of beilschmiedic acid G ( 2 ) was also confirmed by X‐ray crystallographic analysis.     

Pentacyclic Triterpenoid Saponins from Silene viscidula

Three new pentacyclic triterpenoid saponins, viscidulosides A and B ( 1 and 2 , resp.), and silenoviscoside D ( 3 ), were isolated from the roots of Silene viscidula, together with two known saponins, sinocrassulosides VIII and IX ( 4 and 5 , resp.). Their structures were elucidated by spectroscopic data and chemical methods. Compounds 1 / 2 and 4 / 5 were two inseparable mixtures, which are glycosides of quillaic acid whose fucose residue is acylated by (E)‐ or (Z)‐4‐methoxycinnamic acid.     

Polyhydroxypregnane Glycosides from the Roots of Cynanchum otophyllum

Six new polyhydroxypregnane glycosides, namely cynotophyllosides A–F ( 1 – 6 ), together with five known steroids, were isolated from the roots of Cynanchum otophyllum. Their structures were elucidated by extensive spectroscopic methods (especially 2D‐NMR techniques) and acid‐catalyzed hydrolysis. Furthermore, high field 1D‐ and 2D‐NMR experiments were employed to elucidate the structure of 8 previously deduced only on the basis of LC/MS data.     

A new flavane acid from the fruits of Illicium verum

A new compound, illiciumflavane acid (1), along with 13 known compounds (2–14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR (¹H NMR, ¹³C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC₅₀ values of 4.63 μM and 9.17 μM, respectively.     

Scyphiphorins A and B,Two New Iridoid Glycosides from the Stem Bark of a Chinese Mangrove Scyphiphora hydrophyllacea

Two new iridoid glycosides, named scyphiphorins A ( 1 ) and B ( 2 ), together with four known compounds, geniposidic acid (=(1S,4aS,7aS)‐1‐(β‐D ‐glucopyranosyloxy)‐1,4a,5,7a‐tetrahydro‐7‐(hydroxymethyl)cyclopenta[c]pyran‐4‐carboxylic acid; 3 ), 4‐(4‐hydroxy‐3‐methoxybenzyl)butan‐2‐one, oleanolic acid (=(3β)‐3‐hydroxyolean‐12‐en‐28‐oic acid), and stigmasterol β‐D ‐glucoside (=(3β,22E)‐stigmasta‐5,22‐dien‐3‐yl β‐D ‐glucopyranoside), were isolated for the first time from the stem bark of a Chinese mangrove, Scyphiphora hydrophyllacea Gaertn . f. The structures of compounds 1 and 2 were determined as 10‐O‐benzoylgeniposidic acid and 10‐O‐[(2E,6R)‐8‐hydroxy‐2,6‐dimethyl‐1‐oxooct‐2‐en‐1‐yl]geniposidic acid, respectively, on the basis of spectroscopic data and chemical methods, including 2D NMR techniques.     

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.     

Phenylpropanoid Esters of Rhamnose from Buddleja asiatica

Four new phenylpropanoid esters of rhamnose, asiatisides A–D, along with the known compounds, buergeriside C₁ ( 5 ), p‐methoxycinnamic acid, ferulic acid, and O‐methylferulic acid were obtained from the aerial parts of Buddleja asiatica Lour by chromatographic methods. The new compounds were elucidated as 3‐O‐acetyl‐4‐O‐(p‐methoxycinnamoyl)‐α‐L ‐rhamnopyranose ( 1 ), 3‐O‐acetyl‐4‐O‐feruloyl‐α‐L ‐rhamnopyranose ( 2 ), 2‐O‐acetyl‐4‐O‐(O‐methylferuloyl)‐α‐L ‐rhamnopyranose ( 3 ), 2‐O‐acetyl‐4‐O‐(p‐methoxycinnamoyl)‐α‐L ‐rhamnopyranose ( 4 ) by spectral data (1D‐, 2D‐NMR, and MS), respectively.     

Structure elucidation of new oleanane‐type glycosides from three species of Acanthophyllum

From the roots of three species of Acanthophyllum (Caryophyllaceae), two new gypsogenic acid glycosides, 1 and 2, were isolated, 1 from A. sordidum and A. lilacinum, 2 from A. elatius and A. lilacinum, together with three known saponins, glandulosides B and C, and SAPO50. The structures of 1 and 2 were established mainly by 2D NMR techniques as 23‐O‐β‐D ‐galactopyranosylgypsogenic acid‐28‐O‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐glucopyranosyl‐(1→6)]‐β‐D ‐galactopyranoside (1) and gypsogenic acid‐28‐O‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐glucopyranosyl‐(1→6)]‐β‐D ‐galactopyranoside (2). The cytotoxicity of several of these saponins was evaluated against two human colon cancer cell lines (HT‐29 and HCT 116). Copyright © 2010 John Wiley & Sons, Ltd.     

Chromenone Glucosides Acylated with Monoterpene Acids from the Leaves of Eucalyptus camaldulensis var. obtusa

Three new chromenone glucosides acylated with monoterpene acids, eucamaldusides A ( 1 ), B ( 2 ), and C ( 3 ), were isolated from the leaves of Eucalyptus camaldulensis var. obtusa, together with the five known compounds ursolic acid lactone, obtusilin, β‐sitosterol glucoside, 4‐hydroxybenzoic acid, and cypellocarpin C. The structures of the new compounds were established by exhaustive 1D‐ and 2D‐NMR spectroscopic studies. Their configuration was determined by measuring the [α]_D of the known methyl esters of the monoterpene acids obtained by methanolysis of 1 – 3 .     

A New Glycine Derivative and a New Indole Alkaloid from the Fermentation Broth of the Plant Endophytic Fungus Pestalotiopsis podocarpi Isolated from the Chinese Podocarpaceae Plant Podocarpus macrophyllus

A new glycine derivative, podocarpiamide ( 1 ), a new indole alkaloid, 1‐methoxy‐1H‐indol‐3‐ethanol ( 2 ), together with two known compounds, 1‐methoxy‐1H‐indole‐3‐acetic acid ( 3 ) and methyl 1‐methoxy‐1H‐indole‐3‐acetate ( 4 ), were isolated from the fermentation broth of the plant endophytic fungus Pestalotiopsis podocarpi. Their structures were elucidated by extensive spectroscopic analysis including 1D‐ and 2D‐NMR (HSQC, HMBC, and COSY) and MS experiments. Compound 1 has an interesting unusual carbamic acid structure.     

A New Diterpenoid and other Constituents from Acanthopanax Brachypus Harms

Phytochemical investigation of the stem bark of Acanthopanax brachypus afforded a new labdanetype diterpene glycoside, 3α‐trans‐sinapoyloxy‐jhanol 18‐O‐β‐D‐glucopyranoside ( 1 ), together with four known compounds, including one diterpene acid, acanthoic acid ( 2 ), one coumarin, isofraxidin ( 3 ), one phenolic glycoside, sasanquin ( 4 ), as well as one chalcone glycoside, okanin 4‐methyl ether‐3′‐O‐β‐D‐glucopyranoside ( 5 ). All of the structures were characterized by means of spectroscopic methods, including ¹H, ¹³C, 2D‐NMR and HR‐MS, as well as chemical methods and comparison with the literature data.     

Three New Sesquiterpenes from Laggera pterodonta

A new eremophilane sesquiterpene, (2β)‐2‐deoxo‐2‐methoxytessaric acid ( 1 ), and two new eudesmane sesquiterpenes, (3β,10α)‐3‐methoxyleudesma‐4,11(13)‐dien‐12‐oic acid ( 2 ) and (3α,4β,8α)‐4‐(acetyloxy)‐3‐(2,3‐dihydroxy)‐2‐methyl‐1‐oxobutoxy‐8‐hydroxyeudesm‐7(11)‐eno‐12,8‐lactone ( 3 ), along with the ten known compounds 4 – 13 were isolated from the aerial parts of Laggera pterodonta. The structures of the new compounds were elucidated by spectroscopic analyses, including 2D‐NMR data.     

A Novel Norlignan and a Novel Phenylpropanoid from Peperomia tetraphylla

A novel cyclobutane‐type norlignan, peperotetraphin (=methyl rel‐(1R,2S,3S)‐2,3‐bis(7‐methoxy‐1,3‐benzodioxol‐5‐yl)cyclobutanecarboxylate; 1 ), and a novel phenylpropanoid, i.e., methyl (2E)‐3‐(7‐methoxy‐1,3‐benzodioxol‐5‐yl)prop‐2‐enoate ( 2 ), along with three known compounds, α‐asarone (=1,2,4‐trimethoxy‐5‐[(1E)‐prop‐1‐en‐1‐yl]benzene), vanillic acid (=4‐hydroxy‐3‐methoxybenzoic acid), and veratric acid (=3,4‐dimethoxybenzoic acid), were isolated from the EtOH extract of the whole plant of Peperomia tetraphylla. Their structures were determined by spectroscopic methods, especially 1D‐ and 2D‐NMR techniques. This is the first report of naturally occurring cyclobutane‐type norlignans.     

Flavonol Glycosides and Iridoids from Asperula lilaciflora

A new flavonol glycoside, quercetin 3‐O‐[6′′′‐O‐3,5‐dihydroxycinnamoyl‐β‐glucopyranosyl‐(1→2)]‐β‐galactopyranoside (named lilacifloroside; 1 ) and a new iridoid 2 (named asperulogenin), were isolated from the aerial parts of Asperula lilaciflora in addition to eight known secondary metabolites, i.e., quercetin, kaempferol, quercetin 3‐O‐β‐glucopyranosyl‐(1→2)‐β‐galactopyranoside, quercetin 3‐O‐β‐glucopyranosyl‐(1→2)‐arabinopyranoside, asperuloside, deacetylasperulosidic acid, asperulosidic acid methyl ester, and chlorogenic acid. The structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR experiments as well as MS data. Compound 1 contains the rare 3,5‐dihydroxycinnamoyl moiety in its structure. This work constitutes the first phytochemical study of the title plant.     

Two Unusual Methylidenecyclopropane Glucosides from Metaxya rostrata C.Presl

Two new natural compounds, (1R,2E)‐2‐(6‐hydroxyhexylidene)cyclopropyl‐β‐D ‐glucopyranoside ( 1 ) and (6E)‐6‐[(2R)‐2‐(β‐D ‐glucopyranosyloxy)cyclopropylidene]hexanoic acid ( 2 ), glucosides of a very rare methylidenecyclopropane alcohol, as well as two known glycosides of phenolic acids, namely 4‐O‐β‐D ‐glucopyranosylcaffeic acid ( 3 ) and (E)‐4‐O‐β‐D ‐glucopyranosylcoumaric acid ( 4 ), and methyl α‐fructofuranoside ( 5 ) were isolated for the first time from the rhizomes of the tree fern Metaxya rostrata C.Presl . The structures were elucidated on the basis of detailed spectroscopic data analysis, and the structure of 1 was additionally confirmed by X‐ray crystal‐structure analysis.     

Iridoid Glycosides and Phenolic Compounds from the Flowers of Vitex agnus‐castus

A new and rare type of iridoid glycoside, agnusoside ( 1 ), a new caffeoylquinic acid derivative, castusic acid ( 2 ), and a new sugar ester, 1,2‐di‐(4‐hydroxybenzoyl)‐β‐glucopyranose ( 3 ), along with ten known compounds belonging to iridoid glycosides (agnuside, trans‐eurostoside), caffeoylquinic acid derivatives (chlorogenic acid and isochlorogenic acid A), flavonoids (isoorientin, isovitexin, kaempferol 3‐O‐sophoroside, luteolin 6‐C‐(2′′‐O‐trans‐caffeoyl)glucopyranoside, and simple phenolic acids (4‐hydroxybenzoic acid, 3,4‐dihydroxybenzoic acid), chemical classes were isolated from the flowers of Vitex agnus‐castus. The structures of the isolates were established by extensive 1D‐ and 2D‐NMR spectroscopic analysis as well as HR‐ESI‐MS. Agnusoside ( 1 ) represents an unusual type of iridoid glycoside with its 6‐keto C(4) nonsubstituted aglycone.     

A new chromone from seeds of <Emphasis Type="Italic">Cydonia oblonga</Emphasis>

The new chromone 5,7-dihydroxy-2-n-pentacosanylchromen-4-one (1) in addition to the three known compounds ursolic acid (2), tormentic acid (3), and β-daucosterol (4) were isolated from seeds of Cydonia oblonga. Their structures were determined based on their 1D and 2D NMR and HR-ESI-MS spectral data.