Further Saponins from Phytolacca dodecandra L′HERIT

Three new bidesmosidic saponins 1 – 3 have been isolated from the berries of Phytolacca dodecandra L′HERIT (Phytolaccaeae). The structures have been established by spectroscopic (¹H-NMR, ¹³C-NMR, FAB-MS, DCI-MS, and GC/MS) and chemical methods (acid, basic, and enzymatic hydrolysis). Saponins 1 and 3 are tetra- and pentaglycosides of oleanolic acid, whereas 2 is a tetraglycoside of bayogenin. The corresponding prosapogenins 1a - 3a , obtained by cleavage of a glucose unit esterified at C(28), exhibited strong molluscicidal activity against schistosomiasis-transmitting snails.     

New Triterpenoidal Saponins from Gypsophila repens

Six new triterpene glycosides, repensosides A–F ( 1 – 6 , resp.), were isolated from the roots of Gypsophila repens L. Their structures, established by extensive 1D‐ and 2D‐NMR spectroscopic experiments as well as MS analyses, were found to be based on gypsogenic acid (or gypsogenin) as aglycone, with three to nine branched or unbranched sugar moieties.     

地奥心血康中的两个新甾体皂苷

通过正相和反相硅胶柱层析, 从地奥心血康药粉的正丁醇萃取物中分离纯化出2个微量的新甾体皂苷, 通过MS和NMR(包括HMQC, HMBC和NOESY)等波谱解析, 结合化学降解分析将其结构鉴定为3β,26-二醇-25(R)-Δ^5,20(22)-二烯-呋甾-26-O-β-D-吡喃葡萄糖苷(1)和26-O-β-D-吡喃葡萄糖基-3β,20α,26-三醇-25(R)-Δ^5,22-二烯-呋甾-3-O-α-L-吡喃鼠李糖基(1→2)-[α-L-吡喃鼠李糖基(1→4)]-β-D-吡喃葡萄糖苷(2).     

New Triterpene Saponins from Acanthophyllum pachystegium

Four new triterpenoid saponins, pachystegiosides A ( 1 ), B ( 2 ), C ( 3 ), and D ( 4 ), were isolated from the roots of Acanthophyllum pachystegium K. H. Their structures were elucidated by means of a combination of homo‐ and heteronuclear 2D‐NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FAB‐MS. The new compounds were characterized as 3‐O‐{O‐β‐D ‐galactopyranosyl‐(1→2)‐O‐[β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucuronopyranosyl}quillaic acid 28‐{O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[3,4‐di‐O‐acetyl‐β‐D ‐quinovopyranosyl‐(1→4)]‐β‐D ‐fucopyranosyl}ester ( 1 ), 3‐O‐{O‐β‐D ‐galactopyranosyl‐(1→2)‐O‐[β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucuronopyranosyl}quillaic acid 28‐{O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[4‐O‐acetyl‐β‐D ‐quinovopyranosyl‐(1→4)]‐β‐D ‐fucopyranosyl} ester ( 2 ), 3‐O‐{O‐β‐D ‐galactopyranosyl‐(1→2)‐O‐[β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucuronopyranosyl}quillaic acid 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[4‐O‐acetyl‐β‐D ‐quinovopyranosyl‐(1→4)]‐β‐D ‐fucopyranosyl} ester ( 3 ), and gypsogenic acid 28‐[O‐β‐D ‐glucopyranosyl‐(1→2)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐O‐β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐galactopyranosyl] ester ( 4 ).     

Two New Steroidal Saponins from Tacca plantaginea

Two new C27 steroidal glycosides, named taccaoside A(1) and B(2), were isolated from the traditional Chinese herb Tacca plantaginea. The spectroscopic and chemical evidences revealed their structures to be 26-O-β-D-glucopyranosyl-(25R)-3β,26-dihydroxy furost-5,20-diene-3-O-[α-L-rhamnopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→3)]-β-D-glucopyranoside(1) and 26-O-β-D-glucopyranosyl-(25R)-3β,26-dihydroxy furost-5,20-diene-3-O-[α-L-rhamnopyranosyl-(1→2)]-[β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→3)]-β-D-glucopyranoside(2),respectively.     

New Triterpene Saponins from Herniaria glabra

Three new saponins 1–3 were isolated from Herniaria glabra by means of prep. HPLC and TLC. The structures were established mainly by a combination of 2D-NMR techniques (COSY, TOCSY, ROESY, HMQC, and HMBC) as O-α-L -rhamnopyranosyl-(1→4)-O-β-D -glucopyranosyl-(1-→6)-O-[β-D -glucopyranosyl-(1→2)]-β-D -glucopyranosyl medicagen-28-ate (herniaria saponin 4; 1 ), O-β-D -glucopyranosyl-(1→3)-O-α-L -rhamnopyranosyl-(1→2)-O-[β-(3R)-D -apiofuranosyl-(1→3)]-β-D -4-O-acetylfucopyranosyl 3-O-(β-D -glucuronopyranosyl)-16α-hydroxymedicagen-28-ate (herniaria saponin 5; 2 ), and O-α-L -rhamnopyranosyl-(1→4)-O-β-D -glucopyranosyl-(1→6)-O-[β-D -6-O-acetylglucopyra nosyl-(1→2)]-β-D -glucopyranosyl medicagen-28-ate (herniaria saponin 6; 3 ).     

New Acylated Saponins from Polygala myrtifolia

The ten new acylated presenegenin (=(2β,3β,4α)‐2,3,27‐trihydroxyolean‐12‐ene‐23,28‐dioic acid) glycosides 1 – 10 have been isolated by successive MPLC from the roots of Polygala myrtifolia L. as five inseparable mixtures of the trans‐ and cis‐4‐methoxycinnamoyl derivatives, i.e., myrtifoliosides A₁/A₂ ( 1 / 2 ), B₁/B₂ ( 3 / 4 ), C₁/C₂ ( 5 / 6 ), D₁/D₂ ( 7 / 8 ), and E₁/E₂ ( 9 / 10 ). Their structures were elucidated mainly by extensive spectroscopic experiments, including 2D NMR techniques, as 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐β‐D ‐galactopyranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[D ‐apio‐β‐D ‐furanosyl‐(1→3)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[α‐L ‐arabinopyranosyl‐(1→3)]‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D ‐fucopyranosyl} ester ( 1 ) and its cis‐isomer 2 , 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐β‐D ‐galactopyranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[D ‐apio‐β‐D ‐furanosyl‐(1→3)]‐α‐L ‐rhamnopyranosyl‐(1→2)‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D ‐fucopyranosyl} ester ( 3 ) and its cis‐isomer 4 , 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐β‐D ‐galactopyranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D ‐fucopyranosyl} ester ( 5 ) and its cis‐isomer 6 , 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐D ‐apio‐β‐D ‐furanosyl‐(1→3)‐O‐[β‐D ‐xylopyranosyl‐(1→4)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D ‐fucopyranosyl} ester ( 7 ) and its cis‐isomer 8 , and 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐α‐L ‐arabinopyranosyl‐(1→3)‐O‐[β‐D ‐xylopyranosyl‐(1→4)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐4‐O‐(trans‐4‐ methoxycinnamoyl)‐β‐D ‐fucopyranosyl} ester ( 9 ) and its cis‐isomer 10 .     

Two New Saponins from Lysimachia davurica

Two new saponins named davuricoside I (1) and davuricoside E (2) were isolated from the whole plants ofLysimachia davurica. Their structures were determined by 1D and 2D NMR, FAB-MS techniques, and chemical methods.     

New Acylated Triterpene Saponins from Polygala arenaria

Eight new acylated triterpene saponins 1 – 8 were isolated from the roots of Polygala arenaria as four inseparable (E)/(Z) mixtures of the 4‐methoxycinnamoyl and 3,4‐dimethoxycinnamoyl derivatives by repeated MPLC over silica gel. Their structures were established mainly by 600‐MHz 2D‐NMR techniques (¹H,¹H‐COSY, TOCSY, NOESY, HSQC, HMBC) as 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐(O‐β‐D ‐galactopyranosyl‐(1→4)‐O‐[β‐D ‐glucopyranosyl‐(1→3)]‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐{4‐O‐[(E)‐4‐methoxycinnamoyl]}‐β‐D ‐fucopyranosyl) ester and its (Z)‐isomer ( 1 / 2 ), 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐(O‐β‐D ‐galactopyranosyl‐(1→4)‐O‐[β‐D ‐glucopyranosyl‐(1→3)]‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐{4‐O‐[(E)‐3,4‐dimethoxycinnamoyl]}‐β‐D ‐fucopyranosyl) ester and its (Z)‐isomer ( 3 / 4 ), 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐(O‐β‐D ‐glucopyranosyl‐(1→3)‐O‐α‐L ‐arabinopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐{4‐O‐[(E)‐4‐methoxycinnamoyl]}‐β‐D ‐fucopyranosyl) ester and its (Z)‐isomer ( 5 / 6 ), and 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐(O‐β‐D ‐glucopyranosyl‐(1→3)‐O‐α‐L ‐arabinopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐{4‐O‐[(E)‐3,4‐dimethoxycinnamoyl]}‐β‐D ‐fucopyranosyl) ester and its (Z)‐isomer ( 7 / 8 ) (presenegenin=(2β,3β)‐2,3,27‐trihydroxyolean‐12‐ene‐23,28‐dioic acid). In our in vitro lymphocyte proliferation assay (Jurkat T‐leukemia cells), a fraction containing 1 – 4 showed a concentration‐dependent immunomodulatory effect. This effect was not found for the prosapogenin (tenuifolin=3‐O‐(β‐D ‐glucopyranosyl)presenegenin), underlining the importance of the acyl? oligosaccharidic moiety.     

New Acylated Preatroxigenin Saponins from Atroxima congolana

Eight new acylated preatroxigenin saponins 1 – 8 were isolated as four inseparable mixtures of the trans‐ and cis‐4‐methoxycinnamoyl derivatives, atroximasaponins A₁/A₂ ( 1 / 2 ), B₁/B₂ ( 3 / 4 ), C₁/C₂ ( 5 / 6 ) and D₁/D₂ ( 7 / 8 ) from the roots of Atroxima congolana. These compounds are the first examples of triterpene saponins containing preatroxigenin (=(2β,3β,4α,22β)‐2,3,22,27‐tetrahydroxyolean‐12‐ene‐23,28‐dioic acid as aglycone. Their structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR studies and FAB‐MS as 3‐O(β‐D ‐glucopyranosyl)preatroxigenin 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[O‐β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D ‐fucopyranoyl} ester ( 1 ) and its cis‐isomer 2 , 3‐O‐(β‐D ‐glucopyranosyl)preatroxigenin 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→ 2)‐O‐[O‐6‐O‐acetyl‐β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐(trans‐ 4‐methoxycinnamoyl)‐β‐D ‐fucopyranosyl} ester ( 3 ) and its cis‐isomer 4 , 3‐O‐(β‐D ‐glucopyranosyl)preatroxigenin 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[β‐D ‐apiofuranosyl‐(1→3)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[O‐6‐ O‐acetyl‐β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D ‐fucopyranoyl} ester ( 5 ) and its cis‐isomer 6 , 3‐O‐(β‐D ‐glucopyranosyl)preatroxigenin 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[β‐D ‐apiofuranosyl‐(1→3)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D ‐fucopyranosyl ester ( 7 ) and its cis‐isomer 8 .     

Three New Triterpene Saponins from Gynostemma pentaphyllum

Three new dammarane‐type triterpene saponins, 1 – 3 , together with three known compounds, 4 – 6 , were isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino . By means of chemical and spectroscopic methods, their structures were established as (20S)‐3β,20,21‐trihydroxydammara‐23,25‐diene 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)] [β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucopyranosyl‐21‐O‐β‐D ‐glucopyranoside ( 1 ), (20R,23R)‐3β,20‐dihydroxy‐19‐oxodammar‐24‐en‐21‐oic acid 21,23‐lactone 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)] [β‐D ‐xylopyranosyl‐(1→3)]‐α‐L ‐arabinopyranoside ( 2 ), and (21S,23S)‐3β,20ξ,21,26‐tetrahydroxy‐19‐oxo‐21,23‐epoxydammar‐24‐ene 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)] [β‐D ‐xylopyranosyl‐(1→3)]‐α‐L ‐arabinopyranoside ( 3 ).     

Two New Spirostanol Saponins from Reineckia carnea

Two new spirostanol saponins, (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐(β‐D ‐xylopyranoside) ( 1 ) and (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐fucopyranoside] ( 2 ), along with two known compounds, (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐xylopyranoside] ( 3 ) and (1β,3β,4β,5β,25S)‐spirostan‐1,3,4,5‐tetrol 5‐(β‐D ‐glucopyranoside) ( 4 ) were isolated from the whole plant of Reineckia carnea. The structures of the new steroids were determined by detailed analysis of their 1D‐ and 2D‐NMR spectra and chemical methods, and by comparison with spectral data of known compounds. Compounds 3 and 4 were isolated from the genus Reineckia for the first time.     

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 Steroidal Saponins from Diuranthera inarticulata

There are only three species in the genus Diuranthera (Liliaceae), which is endemic in the southwest of China1. Four steroidal saponins, diuranthosides A-C and chloromalo-side A were isolated from the fresh roots of D. major. This paper deals with the structure elucidation of two new steroidal saponins, diuranthosides D and E, which were isolated from the methanolic extract of whole plant of D. inarticulata Wang et K. Y. Lang.Diuranthoside D (1), [(]-38 (c 0.08, pyridine), afforded galac…     

Two New Oleanane Saponins from Anemone anhuiensis

Two new oleanane triterpene saponins, named as anhuienside C (1) and D (2), were isolated from the rhizomes of Anemone anhuiensis (Ranunculaceae). The structures of the new compounds were elucidated as 3-O-α-L-rhamnopyranosyl (1→ 2)-β -D-xylopyranosyl oleanolic acid 28-O-b -D-glucopyranosyl (1→ 6)-b -D-glucopyranosyl ester (1) and 3-O-β-D-xylopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl (1→ 4)-β-D-glucopyranosyl (1→6)-β-D-gluco-pyranosyl ester (2), respectively.     

Three New Triterpene Saponins from Bolbostemma paniculatum

Two novel noroleanane saponins, tubeimoside A ( 1 ) and tubeimoside B ( 2 ), and a new dammarane triterpene saponin, tubeimoside C ( 3 ), together with two known compounds, 4 and 5 , were isolated from the bulbs of Bolbostemma paniculatum (Maxim .) Franquet . Compound 4 was found in this genus for the first time. Based on spectroscopic methods, including IR, NMR (DEPT, COSY, HMQC, HMBC, and TOCSY), and MS experiments, and chemical reactions, the structures of the new compounds were elucidated as 3β‐[β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyloxy]‐2β,23‐dihydroxy‐28‐norolean‐12‐en‐16‐one ( 1 ), 3β‐[β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyloxy]‐2β,23‐dihydroxy‐28‐norolean‐12‐en‐22‐one ( 2 ), (3β,7β)‐7,18,20‐trihydroxydammar‐24‐en‐3‐yl 2‐O‐α‐L ‐arabinopyranosyl‐β‐D ‐glucopyranoside ( 3 ).     

Three New Triterpene Saponins from Hemsleya chinensis

Three new triterpenoid saponins, xuedanglycosides A–C ( 1 – 3 , resp.), along with six known ones, were isolated from the rhizomes of Hemsleya chinensis. By detailed analysis of the NMR spectra, by chemical methods, and by comparison with spectral data of known compounds, the structures of new compounds were determined to be 16α,23α‐epoxy‐2β,3α,20β‐trihydroxy‐10α,23α‐cucurbita‐5,24‐dien‐11‐on‐2‐yl β‐D ‐glucopyranoside ( 1 ), 2β,3α,16α,20β‐tetrahydroxycucurbita‐5,25‐diene‐11,22‐dion‐2‐yl β‐D ‐glucopyranoside ( 2 ), and oleanolic acid 28‐O‐β‐xylopyranosyl‐(1→6)‐O‐β‐glucopyranoside ( 3 ). In addition, hemslecin A 2‐O‐β‐D ‐glucopyranoside ( 6 ), hemsamabilinin B ( 7 ), and hemslonin A ( 9 ) were obtained for the first time from this plant.     

Three New Triterpenoid Saponins from Ardisia crenata

Three new triterpenoid saponins, ardisicrenoside I ( 1 ), ardisicrenoside J ( 2 ), and ardisicrenoside M ( 3 ), along with eight known compounds, were isolated from the roots of Ardisia crenata Sims . Their structures were elucidated as 16α‐hydroxy‐30,30‐dimethoxy‐3β‐O‐{β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 1 ), 16α‐hydroxy‐30,30‐dimethoxy‐3β‐O‐{α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 2 ), 30,30‐dimethoxy‐16‐oxo‐3β‐O‐{β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 3 ), ardisiacrispin A ( 4 ), ardisiacrispin B ( 5 ), ardisicrenoside B ( 6 ), ardisicrenoside A ( 7 ), ardisicrenoside H ( 8 ), ardisicrenoside G ( 9 ), cyclamiretin A‐3β‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐arabinopyranoside ( 10 ), and cyclamiretin A‐3β‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐arabinopyranoside ( 11 ) by means of chemical and spectral analysis, and their cytotoxicities were evaluated in vitro.     

Six New Steroidal Saponins from Helleborus thibetanus

Six steroidal saponins, including five spirostanol glycosides, 1 – 5 , and one furostanol glycoside 1‐sulfonate, 6 , previously unknown in nature, together with three known compounds, 7 – 9 , were isolated from dried roots and rhizomes of Helleborus thibetanus. Their structures were elucidated by extensive 1D‐ and 2D‐NMR experiments, along with IR and HR‐ESI‐MS data, as well as the results of acid hydrolysis. Compounds 1 – 5 possessed a C(25)?C(27) bond and were glycosylated at HO? C(1), which was unusual in steroidal saponins.     

Five New Medicagenic Acid Saponins from Muraltia ononidifolia

Five new triterpene saponins 1 – 5 were isolated from the roots of Muraltia ononidifolia E. Mey along with the two known saponins 3‐O‐[O‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl]medicagenic acid 28‐[O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl] ester and 3‐O‐(β‐D ‐glucopyranosyl)medicagenic acid 28‐[O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl] ester (medicagenic acid=(4α,2β,3β)‐2,3‐dihydroxyolean‐12‐ene‐23,28‐dioic acid). Their structures were elucidated mainly by spectroscopic experiments, including 2D‐NMR techniques, as 3‐O‐(β‐D ‐glucopyranosyl)medicagenic acid 28‐[O‐β‐ D ‐apiofuranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl] ester ( 1 ), 3‐O‐(β‐D ‐glucopyranosyl)medicagenic acid 28‐{[O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[β‐D ‐apiofuranosyl‐(1→3)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl} ester ( 2 ), 3‐O‐[O‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl]medicagenic acid 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[β‐D ‐apiofuranosyl‐(1→3)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl} ester ( 3 ), 3‐O‐[O‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl]medicagenic acid 28‐[O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl] ester ( 4 ), and 3‐O‐[O‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl]medicagenic acid ( 5 ).