Phenyl and Phenylethyl Glycosides from Picrorhiza scrophulariiflora

Three new phenyl glycosides, scrophenoside A ( 1 ), B ( 2 ), and C ( 3 ), and two new phenylethyl glycosides, scroside D ( 4 ) and scroside E ( 5 ), were isolated from the stem of Picrorhiza scrophulariiflora Pennell (Scrophularlaceae), besides five known compounds. On the basis of spectroscopic evidence, the structures of the new compounds were elucidated as 4‐acetyl‐2‐methoxyphenyl 6‐O‐[4‐(β‐D ‐glucopyranosyloxy)vanilloyl]‐β‐D ‐glucopyranoside ( 1 ), 4‐acetylphenyl 6‐O‐[(E)‐p‐coumaroyl]‐β‐D ‐glucopyranoside ( 2 ), 4‐[(1R)‐ and (1S)‐1‐hydroxyethyl]‐2‐methoxyphenyl β‐D ‐glucopyranoside ( 3a and 3b , resp.), 2‐(3,4‐dihydroxyphenyl)ethyl O‐β‐D ‐glucopyranosyl‐(1→3)‐4‐O‐[(E)‐feruloyl]‐β‐D ‐glucopyranoside ( 4 ), and 2‐(3,4‐dihydroxyphenyl)ethyl O‐β‐D ‐glucopyranosyl‐(1→3)‐6‐O‐[(E)‐feruloyl]‐β‐D ‐glucopyranoside ( 5 ).     

Seven New Phenolic Glucosides from Viburnum cylindricum

Seven new phenolic glucosides, 2′‐O‐acetylhenryoside ( 1 ), 2′,3′‐di‐O‐acetylhenryoside ( 2 ), 2′,6′‐di‐O‐acetylhenryoside ( 3 ), 2′,3′,6′‐tri‐O‐acetylhenryoside ( 4 ), 2′,3′,4′,6′‐tetra‐O‐acetylhenryoside ( 5 ), 2‐[(2,3‐di‐O‐acetyl‐β‐D ‐glucopyranosyl)oxy]‐6‐hydroxybenzoic acid ( 6 ), and 6‐hydroxy‐2‐[(2,3,4,6‐tetra‐O‐acetyl‐β‐D ‐glucopyranosyl)oxy]benzoic acid ( 7 ), were isolated from the leaves and stems of Viburnum cylindricum, along with 26 known compounds (henryoside=2‐(β‐D ‐glucopyranosyloxy)‐6‐hydroxybenzoic acid [2‐(β‐D ‐glucopyranosyloxy)phenyl]methyl ester). The structures of the new compounds were established on the basis of chemical and spectroscopic evidences.     

New α‐Tetralone Galloylglucosides from the Fresh Pericarps of Juglans sigillata

Three new α‐tetralone galloylglucosides, 1 – 3 , were isolated from the fresh pericarps of Juglans sigillata (Juglandaceae), together with six known compounds. The structures of the new compounds were determined as 1,2,3,4‐tetrahydro‐7‐hydroxy‐4‐oxonaphthalen‐1‐yl 6‐O‐[(3,4,5‐trihydroxyphenyl)carbonyl]‐β‐D ‐glucopyranoside ( 1 ), (1S)‐1,2,3,4‐tetrahydro‐8‐hydroxy‐4‐oxonaphthalen‐1‐yl 6‐O‐[(3,4,5‐trihydroxyphenyl)carbonyl]‐β‐D ‐glucopyranoside ( 2 ), and 1,2,3,4‐tetrahydro‐7,8‐dihydroxy‐4‐oxonaphthalen‐1‐yl 6‐O‐[(3,4,5‐trihydroxyphenyl)carbonyl]‐β‐D ‐glucopyranoside ( 3 ), respectively, on the basis of detailed spectroscopic analyses, and acidic and enzymatic hydrolysis. The antimicrobial activities of the isolated compounds 2, 4 , and 7 – 9 were evaluated.     

New Iridoid and Secoiridoid Glucosides from the Roots of Gentiana manshurica

One new iridoid glucoside, 4″‐O‐β‐D ‐glucosyl‐6′‐O‐(4‐O‐β‐D ‐glucosylcaffeoyl)linearoside ( 1 ), and two new secoiridoid glucosides, 6′‐O‐acetylsweroside ( 2 ) and 6′‐O‐acetyl‐3′‐O‐[3‐(β‐D ‐glucopyranosyloxy)‐2‐hydroxybenzoyl]sweroside ( 3 ), were isolated from the dried roots of Gentiana manshurica (Gentianaceae), together with 11 known ones, including one iridoid glucoside, five secoiridoid glucosides, and five triterpenes. The structures of the new compounds were determined on the basis of detailed spectroscopic analyses and acidic hydrolysis.     

New Triterpenoid Glycosides from Centella asiatica

Four new triterpenoid glycosides named asiaticoside C ( 1 ), D ( 2 ), E ( 3 ), and F ( 4 ) were isolated from the BuOH fraction of the EtOH extract of whole plants of Centella asiatica, together with three known compounds, asiaticoside ( 5 ), madecassoside ( 6 ), and scheffuroside B ( 7 ). Based on FAB‐MS, IR, ¹H‐ and ¹³C‐NMR, and 2D‐NMR data (HMQC, HMBC, COSY), the structures of the new compounds were determined as (2α,3β,4α)‐23‐(acetyloxy)‐2,3‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 1 ), (2α,3β)‐2,3‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 2 ), asiatic acid 6‐O‐β‐D ‐glycopyranosyl‐β‐D ‐glucopyranosyl ester ( 3 ), (3β,4α)‐3,23‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 4 ).     

Chemical Constituents from Myrsine africana L.

Three new compounds, myrsinoside A (=2,4‐dihydroxy‐6‐methylphenyl β‐D ‐(6′‐galloyl)glucopyranoside; 1 ), myrsinoside B (2,4‐dihydroxy‐6‐methylphenyl β‐D ‐glucopyranoside; 2 ), and (3β,16α,20α)‐3,16,28‐trihydroxyolean‐12‐en‐29‐oic acid 3‐{O‐β‐D ‐glucopyranosyl‐(1→2)‐O‐[β‐D ‐glucopyranosyl‐(1→4)]‐α‐L ‐arabinopyranoside} ( 3 ), along with four known compounds, were isolated from the stems of Myrsine africana L. The structures of these new compounds were elucidated on the basis of spectroscopic analysis, including 1D‐ and 2D‐NMR and ESI‐MS techniques, and chemical methods.     

Isoflavonoid Glycosides from the Rhizomes of Iris germanica

Five new di‐ and triglycosides, irigenin 7‐[O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranoside] ( 1 ), 6‐hydroxygenistein 4′‐[O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranoside] ( 2 ), nigricin 4′‐[O‐β‐D ‐glucopyanosyl‐(1→6)‐β‐D ‐glucopyranoside] ( 3 ), nigricin 4′‐[O‐β‐D ‐glucopyanosyl‐(1→2)‐O‐[α‐L ‐rhamnopyranosyl‐(1→6)]‐β‐D ‐glucopyranoside] ( 4 ), and 7‐{4′‐{[2″‐O‐(4′′′′‐acetyl‐2′′′′‐methoxyphenyl)‐β‐D ‐glucopyranosyl]oxy}‐3′‐(β‐D ‐glucopyranosyloxy)phenyl]‐9‐methoxy‐8H‐1,3‐dioxolo[4,5‐g]‐[1 benzopyran‐8‐one‐] ( 5 ), along with a known compound, nigricin 4′‐(β‐D ‐glucopyranoside) ( 6 ), were isolated from the rhizomes of Iris germanica. The structures of these compounds were established by spectroscopic methods, including 2D NMR spectroscopic techniques.     

Dapholidins A – C,New Isomeric Biisoflavonoids From Daphne oleoides

Three new isomeric biisoflavonoids, dapholidins A–C ( 1 – 3 , resp.), have been isolated from the AcOEt‐soluble fraction of the MeOH‐soluble extract of the roots of Daphne oleoides, along with the known compounds daphwazirin ( 4 ), daphnetin 8‐O‐β‐D ‐glucopyranoside ( 5 ), daphnin ( 6 ), daphneticin 4″‐O‐β‐D ‐glucopyranoside ( 7 ), and 6,7‐dihydroxy‐3‐methoxy‐8‐[2‐oxo‐2H‐1‐benzopyran‐7‐(O‐β‐D ‐glucopyranosyl)‐8‐yl]‐2H‐1‐benzopyran‐2‐one ( 8 ). The structures of the new compounds were determined by spectroscopic analyses, including 1D‐ and 2D‐NMR.     

Two new acylated flavonoid glycosides from Morina nepalensis var. alba Hand.‐Mazz.

From the whole plant of Morina nepalensis var. alba Hand.‐Mazz., two new acylated flavonoid glycosides ( 1 and 2 ), together with four known flavonoid glycosides ( 3–6 ), were isolated. Their structures were determined to be quercetin 3‐O‐[2″′‐O‐(E)‐caffeoyl]‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐galactopyranoside (monepalin A, 1 ), quercetin 3‐O‐[2″′‐O‐(E)‐caffeoyl]‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐glucopyranoside (monepalin B, 2 ), quercetin 3‐O‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐galactopyranoside (rumarin, 3 ), quercetin 3‐O‐β‐D ‐galactopyranoside ( 4 ), quercetin 3‐O‐β‐D ‐glucopyranoside ( 5 ) and apigenin 4^′‐O‐β‐D ‐glucopyranoside ( 6 ). Their structures were determined on the basis of chemical and spectroscopic evidence. Complete assignments of the ¹H and ¹³C NMR spectra of all compounds were achieved from the 2D NMR spectra, including H–H COSY, HMQC, HMBC and 2D HMQC‐TOCSY spectra. Copyright © 2002 John Wiley & Sons, Ltd.     

New Cytochalasins from the Marine‐Derived Fungus Xylaria sp. SCSIO 156

Two new cytochalasins, 18‐deoxycytochalasin Q ( 1 ) and 21‐O‐deacetylcytochalasin Q ( 2 ), together with four known analogues, cytochalasin Q ( 3 ), 19,20‐epoxycytochalasin Q ( 4 ), 21‐O‐deacetyl‐19,20‐epoxycytochalasin Q ( 5 ), and cytochalasin D ( 6 ), were isolated from the fungus Xylaria sp. SCSIO156 originated from the South China Sea marine sediment. The structures of 1 and 2 were elucidated by MS and 1D‐ and 2D‐NMR data analyses, and comparison with known compounds. The known compounds 3 – 6 were identified by comparison of their MS and NMR data with those reported in the literature. In the in vitro antitumor assay, compounds 2 – 6 showed mild cytotoxicity against three tumor cell lines (MCF‐7, SF‐268, and NCI‐H460).     

New Glycosides from Salvia moorcroftiana (Lamiaceae)

From the MeOH extract of Salvia moorcroftiana Wall. (Lamiaceae), four new compounds, the two flavonoid glycosides genkwanin 4′‐[O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐galactopyranoside] ( 1 ) and genkwanin 4′‐[O‐α‐L ‐arabinopyranosyl‐(1→3)‐α‐L ‐rhamnopyranoside] ( 2 ), and the two benzene derivatives 4‐hydroxy‐2‐isopropyl‐5‐methylphenyl O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranoside ( 3 ) and nonyl 4‐hydroxybenzoate ( 4 ), were isolated in addition to two known compounds. The structures of all new compounds were determined by 1D and 2D homonuclear and heteronuclear NMR spectroscopy and by comparison with published data.     

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.     

Chemical Components of Seriphidium Santolium Poljak

A new biflavonoid glucoside, apigenin‐7‐O‐β‐D‐glucopyranoside‐(3′‐O‐7″)‐quercetin‐3″‐methyl ether ( 1 ) together with twenty known compounds, apigenin ( 2 ), luteolin ( 3 ), chrysoeriol ( 4 ), tricin ( 5 ), hispidulin ( 6 ), pectolinarigenin ( 7 ), eupatilin ( 8 ), 5,7‐dihydroxy‐6,3′,4′,5′‐tetramethoxyflavone ( 9 ), 5,7,4′‐trihydroxy‐6,3′,5′‐trimethoxyflavone ( 10 ), 3,6‐O‐dimethylquercetagetin‐7‐O‐β‐D‐glucoside ( 11 ), 6‐hydroxy‐5,7‐dimethoxy‐coumarin ( 12 ), taraxerol ( 13 ), taraxeryl acetate ( 14 ), a mixture of β‐sitosterol ( 15 ) and stigmasterol ( 16 ), a mixture of the n‐alkyl trans‐p‐coumarates ( 17 ), a mixture of the n‐alkyl trans‐ferulates ( 18 ), 2‐hydroxy‐4,6‐dimethoxyacetophenone ( 19 ), 4‐hydroxy‐2,6‐dimethoxyphenol‐1‐O‐β‐D‐glucopyranoside ( 20 ), and 2‐hydroxycinnamoyl‐β‐D‐glucopyranoside ( 21 ), were isolated from the whole plant of Seriphidium santolium Poljak. The structures of these compounds were determined by means of spectral and chemical studies.     

Flavone Glycosides from Strobilanthes Formosanus

Two new flavone glycosides, 3′‐hydroxy‐5,7‐dimethoxyflavone 4′‐O‐β‐D‐apiofuranoside ( 1 ), and 5,7‐dimethoxyflavone 4′‐O‐[β‐D‐apiofuranosyl(1→5)‐ β‐D‐glucopyranoside] ( 2 ) along with four known compounds, 4′‐hydroxy‐5,7‐dimethoxyflavone ( 3 ), 2,6‐dimethoxy‐1,4‐benzoquinone ( 4 ), lupeol ( 5 ) and betulin ( 6 ) were isolated from the stem and roots of Strobilanthes formosanus. Their structures were elucidated on the basis of their spectroscopic evidence.     

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.     

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.     

Oleanane Saponins from Rhizome of Anemone raddeana

Two new oleanolic acid‐type triterpenoid saponins, raddeanosides R₂₂ and R₂₃ ( 1 and 2 , resp.), together with four known saponins were isolated from the rhizome of Anemone raddeana Regel. The structures of the new compounds were elucidated as oleanolic acid 3‐O‐β‐D ‐glucopyranosyl(1→2)[β‐D ‐glucopyranosyl(1→4)]‐α‐L ‐arabinopyranoside ( 1 ) and oleanolic acid 3‐O‐α‐L ‐arabinopyranosyl(1→3)‐α‐L ‐rhamnopyranosyl(1→2)[β‐D ‐glucopyranosyl(1→4)]‐α‐L ‐arabinopyranoside ( 2 ). The four known compounds were identified as oleanolic acid 3‐O‐α‐L ‐arabinopyranoside ( 3 ), oleanolic acid 3‐O‐β‐D ‐glucopyranosyl(1→4)‐α‐L ‐arabinopyranoside ( 4 ), hederasaponin B ( 5 ), and hederacholchiside E ( 6 ) on the basis of chemical and spectral evidences. Compound 4 is reported for the first time from the Anemone genus, while the other three known compounds have been already found in this plant.     

New Cytotoxic Myrsinane‐Type Diterpenes from Euphorbia prolifera

Four new myrsinol diterpenes, proliferins A–D ( 1 – 4 , resp.) were isolated from the EtOH extracts of the roots of Euphorbia prolifera, along with four known compounds, euphorprolitherin B ( 5 ), euphorprolitherin D ( 6 ), SPr5 ( 7 ), and 14‐desoxo‐3‐O‐propionyl‐5,15‐di‐O‐acetyl‐7‐O‐nicotinoylmyrsinol‐14β‐acetate ( 8 ). Their structures were established on the basis of spectroscopic methods, including HR‐ESI‐MS, and 1D‐ and 2D‐NMR techniques. The cytotoxicity of compounds 1, 3 , and 4 against cancer cells was evaluated, with compound 1 being active against A2780 cancer cells.     

Phenolic Compounds from the Fresh Leaves of Eucalyptus maideni

Four new phenolic compounds, 7‐O‐methylcatechin 5‐O‐β‐D ‐glucopyranoside ( 1 ), 6‐O‐feruloyl‐D ‐glucopyranose ( 2 ), demethylpiperitol 4‐O‐β‐D ‐glucopyranoside ( 3 ), and 2‐episesaminol 2‐O‐β‐D ‐glucopyranoside ( 4 ) were isolated from the fresh leaves of Eucalyptus maideni, together with six hydrolyzable tannins, 5 – 10 , a flavonol glycoside, 11 , three simple phenolics, 12 – 14 , a monoterpene glucoside, 15 , and a rosenoside, 16 . Their structures were determined on the basis of detailed spectroscopic analysis, acidic hydrolysis, and enzymatic hydrolysis. The known compounds 10 and 13 were obtained from the genus Eucalyptus for the first time.     

Chemical Constituents from the Roots of Schnabelia tetradonta

The new rearranged‐abietane diterpene 1 , the four new triterpenoids 2 – 5 , and the new aminoethylphenyl oligoglycoside 6 , besides 19 known compounds, were isolated from the roots of Schnabelia tetradonta, a Chinese endemic herb. The structures of the new compounds were elucidated on the basis of spectroscopic evidence as 12,17‐epoxy‐11,14,16‐trihydroxy‐17(15→16)‐abeo‐abieta‐8,11,13,15‐tetraen‐7‐one ( 1 ), 21β‐(β‐D ‐glucopyranosyloxy)‐2α,3α‐dihydroxyolean‐12‐en‐28‐oic acid ( 2 ), 2β,3β,16β‐trihydroxy‐15‐oxo‐28‐norolean‐12‐en‐23‐oic acid ( 3 ), 3β‐[(4‐O‐acetyl‐β‐D ‐glucopyranuronosyl)oxy]‐2β,16β‐dihydroxy‐28‐norolean‐15‐oxo‐12‐en‐23‐oic acid ( 4 ), 3β‐[(4‐O‐acetyl‐6‐O‐methyl‐β‐D ‐glucopyranuronosyl)oxy]‐2β,16β‐dihydroxy‐15‐oxo‐28‐norolean‐12‐en‐23‐oic acid ( 5 ), and 4‐[2‐(acetylamino)ethyl]phenyl O‐6‐O‐[(Z)‐p‐methoxycinnamoyl]‐β‐D ‐glucopyranosyl‐(1→2)]‐O‐[β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐acetyl‐α‐L ‐rhamnopyranoside ( 6 ), respectively.