Steroidal Saponins from Disporopsis pernyi

Four new steroidal saponins, named disporosides A–D ( 1 – 4 ), corresponding to (3β,25R)‐3‐[(β‐D ‐glucopyranosyl‐(1→2)‐[β‐D ‐glucopyranosyl‐(1→6)]‐β‐D ‐glucopyranosyl)oxy]‐5β‐spirostan ( 1 ), (3β,25R)‐3‐[(β‐D ‐glucopyranosyl‐(1→2)‐[6‐O‐hexadecanoyl‐β‐D ‐glucopyranosyl‐(1→6)]‐β‐D ‐glucopyranosyl)oxy]‐5β‐spirostan ( 2 ), (3β,22R,25R)‐26‐[(β‐D ‐glucopyranosyl)oxy]‐3‐[(β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl)oxy]‐5β‐furostan ( 3 ), and (3β,22R,25R)‐26‐[(β‐D ‐glucopyranosyl)oxy]‐3‐[(β‐D ‐glucopyranosyl‐(1→2)‐[β‐D ‐glucopyranosyl‐(1→6)]‐β‐D ‐glucopyranosyl)oxy]‐5β‐furostan ( 4 ), have been isolated from the fresh rhizomes of Disporopsis pernyi, together with the three known compounds Ys‐I, agavoside B, and (3β,25R)‐3‐[(β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranosyl)oxy]‐5α‐spirostan‐12‐one. Their structures were elucidated by spectroscopic analyses, chemical transformations (acid hydrolysis), and comparison with literature data.     

Phenolic Derivatives from the Root Bark of Oplopanax horridus

Four new phenolic derivatives, including two phenylpropanoid glycosides, one benzoate glycoside, and one lignan glycoside, together with one known glyceride, were isolated from the root bark of Oplopanax horridus. The structures of the new compounds were elucidated as 3‐{4‐[(6‐O‐acetyl‐β‐D ‐glucopyranosyl)oxy]‐3,5‐dimethoxyphenyl}propanoic acid ( 1 ), (+)‐[5,6,7,8‐tetrahydro‐7‐(hydroxymethyl)‐10,11‐dimehoxydibenzo[a,c][8]annulen‐6‐yl]methyl β‐D ‐glucopyranoside ( 2 ), (+)‐methyl 4‐[6‐O‐{3‐hydroxy‐3‐methyl‐5‐(1‐methylpropyl)oxy]‐5‐oxopentanoyl}‐4‐O‐(β‐D ‐glucopyranosyl)‐β‐D ‐glucopyranosyl)oxy]‐3‐methoxybenzoate ( 3 ), and 2‐methoxy‐4‐[(1E)‐3‐methoxy‐3‐oxoprop‐1‐en‐1‐yl]phenyl 6‐O‐{3‐hydroxy‐3‐methyl‐5‐[(1‐methylpropyl)oxy]‐5‐oxopentanoyl‐4‐O‐β‐d‐ glucopyranosyl‐β‐d‐ glucopyranoside ( 4 ) on the basis of spectroscopic techniques including NMR and MS analyses. The known compound was identified as glycer‐2‐yl ferulate ( 5 ) by comparing its physical and spectral data with those reported in the literature.     

Two New Iridoid Glycosides from Hedyotis tenelliflora Blume

Two new iridoid glycosides, teneoside A (=(2aR,5S)‐5‐[(β‐D ‐glucopyranosyl)oxy]‐2a,4a,5,7b‐tetrahydro‐4‐{[(α‐L ‐rhamnopyranosyl)oxy]methyl}‐1H‐2,6‐dioxacyclopenta[cd]inden‐1‐one; 1 ) and teneoside B (=methyl (1S,5R)‐1‐[(β‐D ‐glucopyranosyl)oxy]‐1,4a,5,7a‐tetrahydro‐5‐hydroxy‐7‐{[(α‐L ‐rhamnopyranosyl)oxy]methyl}cyclopenta[c]pyran‐4‐carboxylate; 2 ), were isolated from the roots of Hedyotis tenelliflora Blume , along with two known compounds, deacetylasperuloside ( 3 ) and scandoside methyl ester ( 4 ). Their structures were elucidated by chemical methods (acid hydrolysis) and spectroscopic analyses.     

Hydrolytic Reaction of Plant Extracts to Generate Molecular Diversity: New Dammarane Glycosides from the Mild Acid Hydrolysate of Root Saponins of Panax notoginseng

Molecular diversity was generated by hydrolyzing the crude root saponins of Panax notoginseng (Burk .) F. H. Chen under mild acidic condition (AcOH/EtOH 1 : 1). From the acid hydrolysate, five new dammarane glycosides, named notoginsenoside T₁ (=(3β,6α,12β,20E,23RS)‐24,25‐epoxy‐6‐[(β‐D ‐glucopyranosyl)oxy]‐dammar‐20(22)‐ene‐3,12,23‐triol; 1 ), notoginsenoside T₂ (=(3β,6α,12β,20E,23RS)‐24,25‐epoxy‐6‐[(β‐D ‐glucopyranosyl)oxy]‐23‐methoxydammar‐20(22)‐ene‐3,12‐diol; 2 ), notoginsenoside T₃ (=(3β,6α,12β,20S)‐6‐[(β‐D ‐glucopyranosyl)oxy]‐20‐ethoxydammar‐24‐ene‐3,12‐diol; 3 ), notoginsenoside T₄ (=(3β,6α,12β,20S,22E,24RS)‐6‐[(β‐D ‐glucopyranosyl)oxy]dammar‐22‐ene‐3,12,20,24,25‐pentol; 4 ), and notoginsenoside T₅ (=(3β,6α,12β, 24E)‐6‐[(β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl)oxy]dammara‐20(21),24‐diene‐3,12‐diol; 5 ), were isolated, together with 15 known dammarane glycosides, and their structures were elucidated on the basis of spectroscopic evidence. Among the known compounds, ginsenosides Rg₃ and Rh₁ were isolated as major constituents, in addition to ginsenosides Rg₅, Rh₄, and a mixture of (20R)‐ and (20S)‐25‐hydroxyginsenoside Rh₁, all of which were obtained from P. notoginseng for the first time.     

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 ).     

Eudesmane‐Type Sesquiterpene Derivatives from Saussurea conica

Four new eudesmane‐type sesquiterpene derivatives, 3β‐[(β‐D ‐glucopyranosyl)oxy]‐11αH‐eudesm‐4(14)‐en‐12,8β‐olide ( 1 ), (3β)‐eudesma‐4(14),11(13)‐diene‐3,12‐diol ( 2 ), 3β‐[(β‐D ‐glucopyranosyl)oxy]eudesma‐4(14),11(13)‐dien‐12‐ol ( 3 ), and 3β‐[(β‐D ‐glucopyranosyl)oxy]eudesm‐4(14)‐en‐11‐ol ( 4 ), together with the known (3β)‐eudesm‐4(14)‐ene‐3,11‐diol ( 5 ) were isolated from Saussurea conica, and their structures were elucidated both spectroscopically and by chemical methods.     

Terpenoids from Two Dicranopteris Species

Two new compounds, (6S,13S)‐6‐{[β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}cleroda‐3,14‐dien‐13‐ol ( 1 ) and kadsuric acid 3‐methyl ester ( 2 ), together with nine known compounds, (6S,13E)‐6‐{[β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}cleroda‐3,13‐dien‐15‐ol ( 3 ), (6S,13S)‐6‐[6‐O‐acetyl‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}‐13‐{[α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐fucopyranosyl]oxy}cleroda‐3,14‐diene ( 4 ), (6S,13S)‐6‐{[6‐O‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}‐13‐{[α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐fucopyranosyl]oxy}cleroda‐3,14‐diene ( 5 ), 15‐hydroxydehydroabietic acid ( 6 ), 15‐hydroxylabd‐8(17)‐en‐19‐oic acid ( 7 ), junicedric acid ( 8 ), (4β)‐kaur‐16‐en‐18‐oic acid ( 9 ), (4β)‐16‐hydroxykauran‐18‐oic acid ( 10 ), and (4β,16β)‐16‐hydroxykauran‐18‐oic acid ( 11 ) were isolated from the fronds of Dicranopteris linearis or D. ampla. Their structures were established by extensive 1D‐ and 2D‐NMR spectroscopy. Compounds 1 and 3 – 8 showed no anti‐HIV activities.     

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 Steroidal Saponins from the Leaves of Yucca elephantipes

Two new spirostanol saponins, namely elephanosides G and H ( 1 and 2 , resp.) were isolated from the leaves of Yucca elephantipes (Agavaceae), together with the two known furostanol saponins 3 and 4 and the six known flavonoid O‐ and C‐glycosides 5 – 10 . The new structures were elucidated as (3β,25S)‐spirost‐5‐en‐3‐yl O‐β‐D ‐glucopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 1 ) and (3β,5β,25R)‐3‐[(2‐O‐β‐D ‐glucopyranosyl‐β‐D ‐galactopyranosyl)oxy]spirostan‐12‐one ( 2 ) on the basis of detailed spectroscopic analysis and acidic hydrolysis.     

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.     

Two New Kaempferol Glycosides from Androsace umbellata

Two new kaempferol glycosides, 5‐hydroxy‐2‐(4‐hydroxyphenyl)‐4‐oxo‐7‐(α‐L ‐rhamnopyranosyloxy)‐4H‐chromen‐3‐yl 2‐O‐acetyl‐3‐O‐β‐D ‐glucopyranosyl‐α‐L ‐rhamnopyranoside ( 1 ) and 5‐hydroxy‐2‐(4‐hydroxyphenyl)‐4‐oxo‐7‐(α‐L ‐rhamnopyranosyloxy)‐4H‐chromen‐3‐yl β‐D ‐glucopyranosyl‐(1→2)‐6‐O‐[(2E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranoside ( 2 ), along with ten known compounds, were isolated from the 95% EtOH extract of the whole plant of Androsace umbellata. The structures of the new glycosides were determined on the basis of detailed spectroscopic analyses, including 1D‐ and 2D‐NMR, MS, and chemical methods.     

Seven New Acyl Glycosides from Erycibe obtusifolia

Seven new acyl glycosides, benzyl 5‐O‐vanilloyl‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 1 ), 4‐hydroxy‐3‐methoxyphenyl 5‐O‐syringoyl‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 2 ), isopentyl 5‐O‐syringoyl‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 3 ), 3,4,5‐trimethoxyphenyl 5‐O‐sinapoyl‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 4 ), 6‐methoxy‐7‐[(6‐O‐sinapoyl‐β‐d ‐glucopyranosyl)oxy]coumarin ( 5 ), 6‐methoxy‐7‐[(2‐O‐sinapoyl‐β‐d ‐glucopyranosyl)oxy]coumarin ( 6 ), and isopentyl β‐d ‐apiofuranosyl‐(1→6)‐[5‐O‐syringoyl‐β‐d ‐apiofuranosyl‐(1→2)]‐β‐d ‐glucopyranoside ( 7 ), were isolated from Chinese folk herb Erycibe obtusifolia. Their structures were elucidated on the basis of extensive spectroscopic analysis, including UV, IR, MS, and 1D‐ and 2D‐NMR techniques. Further, these compounds were evaluated against HCT‐8 (human colon carcinoma), Bel‐7402 (human liver carcinoma), BGC‐823 (human stomach carcinoma), A549 (human lung carcinoma), and A2780 (human ovarian carcinoma) cell lines, however, none of them exhibited a significant bioactivity (IC₅₀ > 10 μm ).     

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.     

New Cycloartane and Flavonol Glycosides from Corchorus depressus

Two new monodesmosidic cycloartane triterpene glycosides, depressosides E and F, and two new flavonol glycosides, depressonol A and B, were isolated from the butanol‐soluble part of the EtOH extract of Corchorus depressus L . The structures of the new compounds were elucidated as (22R,24S)‐22,25‐epoxy‐9,19‐cyclolanostane‐3β,16β,24‐triol 3‐[α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐glucopyranoside] ( 1 ), (22R,24S)‐22,25‐epoxy‐9,19‐cyclolanostane‐3β,16β,24‐triol 3‐[α‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranoside] ( 2 ), kaempferol 3‐[β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside] 7‐[α‐L ‐arabinofuranoside] ( 4 ), and kaempferol 3‐[β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐galactopyranoside] 7‐[α‐L ‐arabinofuranoside] ( 5 ) on the basis of chemical evidence and detailed spectroscopic studies.     

Novel Triterpene Saponins from Zizyphus joazeiro

Two dammarane‐type saponins with a novel aglycone derived from the parent 16,22‐epoxy‐24‐methylidenedammarane and lotoside A, a new lotogenin derivative, were isolated from the MeOH extract of the stem bark of the Brazilian medicinal plant Zizyphus joazeiro, in addition to the known saponin 3β‐{{O‐[O‐[α‐L ‐arabinofuranosyl‐(1→2)]‐O‐[β‐D ‐glucopyranosyl‐(1→3)]]‐α‐L ‐arabinopyranosyl}oxy}jujubogenin ( 1 ). The structures of the new compounds were determined as 16,22‐epoxy‐3β‐[(β‐D ‐glucopyranosyl)oxy]‐24‐methylidenedammarane‐15α,16α,20β‐triol ( 2 ), 16,22‐epoxy‐3β‐{{O‐[O‐[β‐D ‐glucopyranosyl‐(1→2)]‐O‐[β‐D ‐apiofuranosyl‐(1→3)]]‐β‐D ‐glucopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl}oxy}‐24‐methylidenedammarane‐15α,16α,20β‐triol ( 3 ), and 3β‐{{O‐[O‐[β‐D ‐glucopyranosyl‐(1→2)]‐O‐[β‐D ‐apiofuranosyl‐(1→3)]]‐β‐D ‐glucopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl}oxy}lotogenin ( 4 ) by means of 1D‐ and 2D‐NMR spectroscopy, as well as FAB mass spectrometry. For the novel aglycone, we propose the name joazeirogenin and, for the new saponins, joazeiroside A ( 2 ) and B ( 3 ). Joazeirogenin was found to be 16,22‐epoxy‐24‐methylidenedammarane‐3β,15α,16α,20β‐tetrol.     

Phenylethanoid Glycosides from the Roots of Digitalis ciliata Trautv.

Three new phenylethanoid glycosides, named digicilisides A – C ( 1  –  3 , resp.), have been isolated from the roots of Digitalis ciliata, along with five known phenylethanoid glycosides. The structures of 1  –  3 were identified as 2‐(4‐hydroxy‐3‐methoxyphenyl)ethyl β‐d ‐glucopyranosyl‐(1→3)‐[α‐l ‐rhamnopyranosyl‐(1→6)]‐4‐O‐[(E)‐feruloyl]‐β‐d ‐glucopyranoside ( 1 ), 2‐(3,4‐dihydroxyphenyl)ethyl α‐l ‐arabinopyranosyl‐(1→2)‐[β‐d ‐glucopyranosyl‐(1→3)]‐[α‐l ‐rhamnopyranosyl‐(1→6)]‐4‐O‐[(E)‐feruloyl]‐β‐d ‐glucopyranoside ( 2 ), and 2‐(3,4‐dihydroxyphenyl)ethyl β‐d ‐glucopyranosyl‐(1→3)‐{6‐O‐[(E)‐feruloyl]‐β‐d ‐glucopyranosyl‐(1→6)}‐4‐O‐[(E)‐caffeoyl]‐β‐d ‐glucopyranoside ( 3 ).     

Development of a high‐performance liquid chromatography procedure to identify known and detect novel C‐13 oligosaccharide moieties in diterpene glycosides from Stevia rebaudiana (Bertoni) Bertoni (Asteraceae): Structure elucidation of rebaudiosides V and W

As an aid for structure elucidation of new steviol glycosides, reversed‐phase C18 high‐performance liquid chromatography method was developed with several previously characterized diterpene glycosides, to identify known and detect novel aglycone‐C13 oligosaccharide moieties and indirectly identify C‐19 interlinkages. Elution order of several diterpene glycosides and their aglycone‐C13 oligosaccharide substituted with different sugar arrangements were also summarized. Comparison of the retention time of a product obtained after alkaline hydrolysis with the aglycone‐C‐13 portions of known compounds reported herein allowed us to deduce the exact positions of the sugars in the C‐13 oligosaccharide portion. The elution position of several steviol glycosides with an ent‐kaurene skeleton was helpful to describe an identification key. Two previously uncharacterized diterpene glycosides together with two known compounds were isolated from a commercial Stevia rebaudiana leaf extract. One was found to be 13‐[(2‐O‐β‐d ‐xylopyranosyl‐ 3‐O‐β‐d ‐glucopyranosyl‐β‐d ‐glucopyranosyl)oxy]ent‐kaur‐16‐en‐19‐oic acid‐(2‐O‐β‐d ‐glucopyranosyl‐β‐d ‐glucopyranosyl) ester (rebaudioside V), whereas the other was determined to be 13‐[(2‐O‐β‐d ‐xylopyranosyl‐ 3‐O‐β‐d ‐glucopyranosyl‐β‐d‐ glucopyranosyl)oxy]ent‐kaur‐16‐en‐19‐oic acid‐(2‐O‐α‐l ‐rhamnopyranosyl‐3‐O‐β‐d ‐glucopyranosyl‐β‐d ‐glucopyranosyl) ester (rebaudioside W). Previously reported compounds were isolated in gram quantities and identified as rebaudioside J and rebaudioside H. In addition, a C‐19 sugar‐free derivative was also prepared from rebaudioside H to afford rebaudioside H₁. Chemical structures were partially determined by the high‐performance liquid chromatography method and unambiguously characterized by using one‐dimensional and two‐dimensional nuclear magnetic resonance experiments.     

Two New Triterpene Saponins from Acanthophyllum laxiusculum

Two new triterpene glycosides, 1 and 2 , together with three known ones, were isolated from roots of Acanthophyllum laxiusculum Schiman ‐Czeika . The structures of the new compounds were established by extensive 1D‐ and 2D‐NMR spectroscopic experiments and MS analyses as 23‐O‐β‐D ‐galactopyranosylgypsogenic acid 28‐O‐{β‐D ‐glucopyranosyl‐(1→2)‐6‐O‐[4‐carboxy‐3‐hydroxy‐3‐methyl‐1‐oxobutyl]‐β‐D ‐glucopyranosyl‐(1→6)}‐[β‐D ‐glucopyranosyl‐(1→3)]‐β‐D ‐galactopyranosyl ester ( 1 ) and gypsogenic acid 28‐O‐{β‐D ‐glucopyranosyl‐(1→2)‐6‐O‐[4‐carboxy‐3‐hydroxy‐3‐methyl‐1‐oxobutyl]‐β‐D ‐glucopyranosyl‐(1→6)}‐[β‐D ‐glucopyranosyl‐(1→3)]‐β‐D ‐galactopyranosyl ester ( 2 ).     

Two New Cytotoxic Nonsulfated Pentasaccharide Holostane (=20‐Hydroxylanostan‐18‐oic Acid γ‐Lactone) Glycosides from the Sea Cucumber Holothuria grisea

Two new lanostane‐type nonsulfated pentasaccharide triterpene glycosides, 17‐dehydroxyholothurinoside A ( 1 ) and griseaside A ( 2 ), were isolated from the sea cucumber Holothuria grisea. Their structures were elucidated by spectroscopic methods, including 2D‐NMR and MS experiments, as well as chemical evidence. Compounds 1 and 2 possess the same pentasaccharide moieties but differ slightly in their side chains of the holostane‐type triterpene aglycone. The structures of the two new glycosides were established as (3β,12α)‐22,25‐epoxy‐3‐{(O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[O‐3‐O‐methyl‐β‐D ‐glucopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐6‐deoxy‐β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐xylopyranosyl)oxy}‐12,20‐dihydroxylanost‐9(11)‐en‐18‐oic acid γ‐lactone ( 1 ) and (3β,12α)‐3‐{(O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[O‐3‐O‐methyl‐β‐D ‐glucopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐6‐deoxy‐β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐xylopyranosyl)oxy}‐12,20,22‐trihydroxylanost‐9(11)‐en‐18‐oic acid γ‐lactone ( 2 ). The 17‐dehydroxyholothurinoside A ( 1 ) and griseaside A ( 2 ) exhibited significant cytotoxicity against HL‐60, BEL‐7402, Molt‐4, and A‐549 cancer cell lines.     

Two Antioxidant Alkaloids from Portulaca oleracea L.

Two alkaloids, oleraceins F and G, were isolated from Portulaca oleracea L., and their structures were determined as methyl (2S)‐6‐[(β‐D ‐glucopyranosyl)oxy]‐2,3‐dihydro‐5‐hydroxy‐1‐[(2E)‐3‐(4‐hydroxy‐3‐methoxyphenyl)prop‐2‐enoyl]‐1H‐indole‐2‐carboxylate and methyl (2S)‐6‐[(β‐D ‐glucopyranosyl)oxy]‐2,3‐dihydro‐5‐hydroxy‐1‐[(2E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]‐1H‐indole‐2‐carboxylate, based on their spectroscopic data. Oleraceins F and G exhibited scavenging activity against 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) radical, with EC₅₀ values of 21.00 and 37.69 μM , respectively.