Triterpenoid Saponins from Pulsatilla cernua （Thunb.） Bercht. et Opiz.

To investigate saponins from the roots of Pulsatilla cernua （Thunb.） Bercht. et Opiz., two new compounds together with five known trlterpenold saponins were isolated. The structures of the two new trlterpenoid saponins, named cernuasides A and B, were elucidated as 3-O-[β-D-xylopyranosyl（1-）2）]-[α-L-rhamnopyranosyl（1-）4）]-α-L- arablnopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester （compound 1） and 3-O-[α-L-arabinopyranosyl（1→）3）]- [α-L-rhamnopyranosyl （1→）2）]-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester （compound 2） by 1D, 2D-NMR techniques, ESIMS analysis, as well as chemical methods.     

Glycosides from Roots of Cyathula officinalis Kuan

To search for new and bioactive compounds from traditional Chinese medicines, a new glycoside,3-O-[α-L-rhamnopyranosyl-(l-→3)-(n-butyl-β-D-glucopyranosiduronate)]-28-O-β-D-glucopyranosyl oleanolic acid (1), was isolated from the roots of Cyathula officinalis Kuan, along with 3-O-(methyl-β-D-glucopyranosiduronate)-28-O-β-D-glucopyranosyl oleanolic acid (2), 3-O-β-D-glucopyranosyl oleanolic acid (3), 3-O-β-D-glucuronopyranosyl oleanolic acid (4), 3-O-[α-L-rhamnopyranosyl-(l→3)-(β-D-glucuronopyranosyl)] oleanolic acid (5), 3-O-(β-D-glucuronopyranosyl)-28-O-β-D-glucopyranosyl oleanolic acid (6), 28-O-β-D-glucuronopyranosyl-(1→4)-β-D-glucopyranosyl hederagenin (7), 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl]-28-O-β-D-glucopyranosyl oleanolic acid (8), and 3-O-[β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl]-28-O-β-D-glucopyranosyl oleanolic acid (9). The structures of these compounds were determined based on spectral and chemical evidence. The 50 per cent growth-inhibiting (GI50) of compounds 1 and 5 against MDA-MB-231(a human breast cancer cell line) was 3.44 × 10-4 and 4.66 × 10-4 mol/L, respectively.     

New Cytotoxic Saponins from Lysimachia davurica Ledeb.

To investigate the saponins from whole plants of Lysimachia davurica Ledeb., two new saponins named davuricoside I （compound 1） and E （compound 2） were isolated. Their chemical structures were elucidated as 3β, 16α, 28, 29-tetrihydroxy-olean-12-en-3-O-β-D-glucopyranosyl-（1→2）-β-D-glucuronopyranoside （compound 1） and 3β, 16α, 29-trihydroxy-13, 28-epoxy-oleanane-3-O-β-D-glucopyranosyl-（1→2）-β-D-glucuronopyranoside （compound 2） on the basis of their one- and two-dimensional nuclear magnetic resonance and mass spectrometry data, and chemical methods. Compound 1 showed significant cytotoxic activity against human A2780 cells.     

白花刺参中两个新三萜皂甙

从著名藏药白花刺参（Morina nepalensis var.alba Hand.-Mazz)的水溶性部分分离到2个新三萜皂甙-刺参甙K（1）和刺参甙L（2）,以及一个已知三萜皂甙mazusaponinⅠ（3)。应用波谱和化学方法,刺参甙K和刺参甙L的结构分别鉴定为3-O-α-L-arabinopyranosyl-（1→）-β-D-xylopyranosyl siaresinolic acid(1)和3-O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl siaresinolic acid28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside(2)。     

A New Steroidal Glycoside from Ophiopogon japonicus （Thunb.） Ker-Gawl.

To study the chemical constituents from traditional Chinese herb Ophiopogon japonicus （Thunb.） Ker-Gawl., a new steroidal glycoside, named ophiopojaponin C （1）, together with two known ones, was isolated by column chromatography. Spectroscopic and chemical evidence revealed the structures to be ophiopogenin 3-O-[α-L-rhamnopyranosyl（1→2）]-β-D-xylopyranosyl（1→4）-β-D-glucopyranoside （1）, diosgenin 3-O-[2-O-acetyl-α-L-rhamnopyranosyl（1→2）]-β-D-xylopyranosyl（1→3）-β-D-glucopyranoside （2）, and ruscogenin 1-O-[2-O-acetyl-α-L-rhamnopyranosyl（1→2）]-β-D-xylopyranosyl（1→3）-β-D-fucopyranoside （3）.     

中国特有药用植物铁破锣中的新皂甙类成分

从铁破锣（Beesia calthaefolia(Maxim.)Ulbr.根茎中分离得到5个化合物（1－5）,经化学和波谱学方法鉴定,其中2个为有机酸－铁破锣酸（beesic acid,9-phenyl-2E,4E,6E,8E-nontetraenoic acid,1)和香草酸（2）;3个为齐墩果酸型三萜皂甙：oleanolic acid-3-o－α-Larabinopyranosyl-－28－O-α-L-rhamnopyranosyl-(1→4）-β-D-glucopyranosyl-（1→6）-β-D-glucopyranosyl ester(3),hederasaponin B(oleanolic acid-3-O-α-L-rhamnopyranosyl-(1→2)-α－L-arabinopyranosly-28-Oα-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6）－β－D－glucopyranosyl ester,4)和铁破锣皂甙Q（beesioside Q,oleanolic acid-3-O-β-D-glucopyranosyl-(1→3）－α－L-rhamnopyranosyl-(1→2)-α-L-arabinopyranolsyl-28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6）－β－D－glucopyranosyl ester,5)。化合物1系首次从自然界中分离得到,化合物5为新化合物。     

Two New Saponins from Lysimachia capillipes Hemsl.

To investigate the saponins from whole plants of Lysimachia capillipes Hemsl., two new saponins, named capilliposide E (1) and capilliposide F (2), were isolated. The structures of the new sa ponins were elucidated as 3 β, 22α-dihydroxy- 16α-acetat-28→ 13 -lactone-oleanane-3 -O- [β-D-glucopyranosyl(1→2)-α-L-arabinpyranoyl]-22-O-β-D-glucopyranoside (1) and 3 β, 22α-dihydroxy- 16α-acetat-28→ 13-1actone-oleanane-3-O- { [β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)]-α-L-arabinpyranoyl }-22-O-βD-glucopyranoside (2). The structures of these compounds were determined by 1D- and 2D-NMR, MS techniques, and chemical methods.     

白花刺参中两个新三萜皂甙

从著名藏药白花刺参(Morina nepalensis var.alba Hand.-Mazz.)的水溶性部分分离到2个新三萜皂甙--刺参甙K(1)和刺参甙L(2),以及一个已知三萜皂甙mazusaponin I(3).应用波谱和化学方法,刺参甙K和刺参甙L的结构分别鉴定为3-O-α-L-arabinopyranosyl-(1→3)-β-D-xylopyranosyl siaresinolic acid(1)和3-O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl siaresinolic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside(2).     

Two New Sesquiterpenoid Glucosides from the Aerial Parts of Saussurea involucrate

Two new sesqulterpenoid glucosides, namely α-hydroxycostic acid 6-β-D-glucopyranoside （compound 1） and 11 βH-11,13-dlhydrodehydrocostuslactone 8α-O-（6＇-acetyl）-β-D-glucopyranoside （compound 2）, along with 11 known sesqulterpenoids （compounds 3-13） were isolated from the aerial parts of Saussurea involucrate （Kar. et Kir.） Sch.- BIp. The structures of the new sesquiterpenoid glucosides were established by one- and two-dimensional nuclear magnetic resonance and mass spectrometry analysis.     

Chemical Constituents of Schisandra rubriflora Rehd. et Wils.

Schisandra rubriflora Rehd. et Wils. is a traditional Chinese medicine. To search for new and bioactive components from traditional Chinese medicines and provide scientific evidence for taxonomy, the chemical constituents of the plant were investigated by various column chromatography methods (silica gel, Sephadex LH-20, and RP-18). From the aerial parts of S. rubriflora, three new megastigmane glycosides,namely (3S, 5R, 6S, 9R)-megastigmane-3, 9-diol 3-O-[α-L-arabionfuranosyl-(1→6)-β-D-glucopyranoside](1), 7-megastigmene-3-ol-9-one 3-O-[α-L-arabionfuranosyl-(1→6)-β-D-glucopyranoside] (2), and megastigmane-3α, 4β, 9ξ-tfiol 3-O-β-D-glucopyranoside (3), along with 14 known compounds, were isolated.The structures of the new compounds were elucidated by a combination of spectroscopic and chemical methods.     

Oleanane‐Type Glycosides from Tremastelma palaestinum (L.) Janchen

Three new oleanane‐type glycosides, 1 – 3 , were isolated from the whole plant of Tremastelma palaestinum (L.) Janchen, along with eight known triterpene glycosides. The structures of the new compounds were established as 3‐O‐[β‐d‐ glucopyranosyl‐(1→3)‐α‐l‐ rhamnopyranosyl‐(1→3)‐β‐d‐ glucopyranosyl‐(1→3)‐α‐l‐ rhamnopyranosyl‐(1→2)‐α‐l‐ arabinopyranosyl]hederagenin ( 1 ), 3‐O‐[β‐d‐ glucopyranosyl‐(1→3)‐α‐l‐ rhamnopyranosyl‐(1→3)‐β‐d‐ glucopyranosyl‐(1→3)‐α‐l‐ rhamnopyranosyl‐(1→2)‐α‐l‐ arabinopyranosyl]hederagenin 28‐O‐β‐d‐ glucopyranosyl‐(1→6)‐β‐d‐ glucopyranosyl ester ( 2 ), and 3‐O‐[α‐l‐ rhamnopyranosyl‐(1→3)‐β‐d‐ glucopyranosyl‐(1→3)‐α‐l‐ rhamnopyranosyl‐(1→2)‐α‐l‐ arabinopyranosyl]oleanolic acid 28‐O‐β‐d‐ glucopyranosyl‐(1→6)‐β‐d‐ glucopyranosyl ester ( 3 ) by using 1D‐ and 2D‐NMR techniques and mass spectrometry. This is the first report on the phytochemical investigation of a species belonging to Tremastelma genus.     

Phenolic compounds from the whole plants of Gentiana rhodantha (Gentianaceae)

Gentiana rhodantha Franch. ex Hemsl. (Gentianaceae), an annual herb widely distributed in the southwest of China, has been medicinally used for the treatment of inflammation, cholecystitis, and tuberculosis by the local people of its growing areas. Chemical investigation on the whole plants led to the identification of eight new phenolic compounds, rhodanthenones A–D ( 1 – 4 , resp.), apigenin 7‐O‐glucopyranosyl‐(1→3)‐glucopyranosyl‐(1→3)‐glucopyranoside ( 5 ), 1,2‐dihydroxy‐4‐methoxybenzene 1‐O‐α‐L ‐rhamnopyranosyl‐(1→6)‐β‐D ‐glucopyranoside ( 6 ), 1,2‐dihydroxy‐4,6‐dimethoxybenzene 1‐O‐α‐L ‐rhamnopyranosyl‐(1→6)‐β‐D ‐glucopyranoside ( 7 ), and methyl 2‐O‐β‐D ‐glucopyranosyl‐2,4,6‐trihydroxybenzoate ( 8 ), together with eleven known compounds, 9 – 19 . Their structures were determined on the basis of detailed spectroscopic analyses and chemical methods. Acetylcholinesterase (AChE) inhibition and cytotoxicity tests against five human cancer cell lines showed that only rhodanthenone D ( 4 ) and mangiferin ( 12 ) exhibited 18.4 and 13.4% of AChE inhibitory effects at a concentration of 10⁻⁴ M , respectively, while compounds 1 – 5 and the known xanthones lancerin ( 11 ), mangiferin ( 12 ), and neomangiferin ( 13 ) displayed no cytotoxicity at a concentration of 40 μM .     

Inhibition of NO Production by Grindelia argentina and Isolation of Three New Cytotoxic Saponins

A bioassay‐guided phytochemical analysis of the ethanolic extract of Grindelia argentina Deble & Oliveira ‐Deble (Asteraceae) allowed the isolation of a known flavone, hispidulin, and three new oleanane‐type saponins, 3‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester ( 2 ), 3‐O‐β‐D ‐glucopyranosyl‐2β,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester, ( 3 ) and 3‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐2β,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester ( 4 ), named grindeliosides A–C, respectively. Their structures were determined by extensive 1D‐ and 2D‐NMR experiments along with mass spectrometry and chemical evidence. The isolated compounds were evaluated for their inhibitory activities against LPS/IFN‐γ‐induced NO production in RAW 264.7 macrophages and for their cytotoxic activities against the human leukemic cell line CCRF‐CEM and MRC‐5 lung fibroblasts. Hispidulin markedly reduced LPS/IFN‐γ‐induced NO production (IC₅₀ 51.4 μM ), while grindeliosides A–C were found to be cytotoxic, with grindelioside C being the most active against both CCRF‐CEM (IC₅₀ 4.2±0.1 μM ) and MRC‐5 (IC₅₀ 4.5±0.1 μM ) cell lines.     

Three New Polyacetylene Glycosides from the Roots of Heracleum dissectum and Their Triglyceride Accumulating Activities in 3T3‐L1 Cells

Continually phytochemical study of the roots of Heracleum dissectum had led to the isolation of three previously undescribed polyacetylene glycosides ( 1 – 3 ), together with seven known compounds, including one polyacetylene ( 8 ) and six coumarins ( 4 – 7 and 9 – 10 ) using diverse chromatographic methods. The structures of these three new compounds were characterized and identified as deca‐4,6‐diyn‐1‐yl β‐d ‐glucopyranosyl‐(1→6)‐β‐d ‐glucopyranosyl‐(1→2)‐β‐d ‐glucopyranoside ( 1 ), (8Z)‐dec‐8‐ene‐4,6‐diyn‐1‐yl β‐d ‐glucopyranosyl‐(1→6)‐β‐d ‐glucopyranosyl‐(1→2)‐β‐d ‐glucopyranoside ( 2 ), and (8E)‐dec‐8‐ene‐4,6‐diyn‐1‐yl β‐d ‐glucopyranosyl‐(1→6)‐β‐d ‐glucopyranosyl‐(1→2)‐β‐d ‐glucopyranoside ( 3 ) based on their physicochemical properties and extensive analyses of various spectroscopic data. Their triglycerides accumulating activities were assayed and the results showed that the three new polyacetylene glycosides ( 1 – 3 ) exhibited triglyceride accumulating activities in 3T3‐L1 adipocytes.     

Oleanane‐type Saponins from Glochidion hirsutum and Their Cytotoxic Activities

Five new oleanane‐type saponins, hirsutosides A – E, were isolated from the leaves of Glochidion hirsutum (Roxb .) Voigt . Their structures were elucidated as 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐β‐d ‐glucopyranoside ( 1 ), 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐β‐d ‐glucopyranosyl‐(1 → 3)‐β‐d ‐glucopyranoside ( 2 ), 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐6‐acetyl‐[β‐d ‐glucopyranosyl‐(1 → 3)]‐β‐d ‐glucopyranoside ( 3 ), 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐β‐d ‐glucopyranosyl‐(1 → 3)‐〈‐l ‐arabinopyranoside ( 4 ), and 21β‐benzoyloxy‐3β,16β,23‐trihydroxyolean‐12‐ene‐28‐al 3‐O‐β‐d ‐glucopyranosyl‐(1 → 3)‐α‐l ‐arabinopyranoside ( 5 ). All isolated compounds were evaluated for cytotoxic activities on four human cancer cell lines, HepG‐2, A‐549, MCF‐7, and SW‐626 using the SRB assay. Compounds 1 , 2 , 4 , and 5 showed significant cytotoxic activities against all human cancer cell lines with IC₅₀ values ranging from 3.4 to 10.2 μm . Compound 3 containing acetyl group at glc C(6″) exhibited weak cytotoxic activity with IC₅₀ values ranging from 47.0 to 54.4 μm .     

Simenoside A,a New Triterpenoid Saponin from Gypsophila simonii Hub.‐Mor.

Saponins are amphiphilic glycoconjugates which give soap‐like foams in H₂O. A new triterpenoid saponin, simenoside A ( 1 ), based on gypsogenin aglycone, and the known saponin 2 were isolated from Gypsophila simonii Hub.‐Mor. The structure of the new saponin was elucidated as 3‐O‐β‐D ‐galactopyranosyl‐(1→2)‐[β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucuronopyranosylgypsogenin 28‐O‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐xylopyranosyl‐(1→4)]‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐fucopyranosyl ester on the basis of extensive spectral analyses and chemical evidence. Saponins 1 and 2 were isolated from G. simonii for the first time.     

Triterpene Glucosides from the Leaves of Aralia elata and Their Cytotoxic Activities

Three new triterpene glucosides, named congmuyenosides C–E ( 1 – 3 , resp.), along with four known ones, were isolated from an EtOH extract of Aralia elata (Miq .) Seem . leaves. The structures of the new compounds were identified as 3‐O‐{β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐glucopyranosyl}caulophyllogenin ( 1 ), 3‐O‐{β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐glucopyranosyl}hederagenin 28‐O‐β‐D ‐glucopyranosyl ester ( 2 ), 3‐O‐{β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐glucopyranosyl}echinocystic acid 28‐O‐β‐D ‐glucopyranosyl ester ( 3 ) on the basis of spectral analyses, including MS, ¹H‐NMR, ¹³C‐NMR, DEPT, HSQC, HMBC, NOESY, and HSQC‐TOCSY experiments. All isolates obtained were evaluated for their cytotoxic activities against three human tumor cell lines (HepG2, SKOV3, and A549). Compound 3 showed significant cytotoxicity against A549 cell line (IC₅₀ 9.9±1.5 μM ).     

Cytotoxic Oleanane‐Type Saponins from the Leaves of Albizia anthelmintica Brongn.

Two new oleanane‐type saponins: β‐d ‐xylopyranosyl‐(1 → 4)‐6‐deoxy‐α‐l ‐mannopyranosyl‐(1 → 2)‐1‐O‐{(3β)‐28‐oxo‐3‐[(2‐O‐β‐d ‐xylopyranosyl‐β‐d ‐glucopyranosyl)oxy]olean‐12‐en‐28‐yl}‐β‐d ‐glucopyranose ( 1 ) and 1‐O‐[(3β)‐28‐oxo‐3‐{[β‐d ‐xylopyranosyl‐(1 → 2)‐α‐l ‐arabinopyranosyl‐(1 → 6)‐2‐acetamido‐2‐deoxy‐β‐d ‐glucopyranosyl]oxy}olean‐12‐en‐28‐yl]β‐d ‐glucopyranose ( 2 ), along with two known saponins: (3β)‐3‐[(β‐d ‐Glucopyranosyl‐(1 → 2)‐β‐d ‐glucopyranosyl)oxy]olean‐12‐en‐28‐oic acid ( 3 ) and (3β)‐3‐{[α‐l ‐arabinopyranosyl‐(1 → 6)‐[β‐d ‐glucopyranosyl‐(1 → 2)]‐β‐d ‐glucopyranosyl]oxy}olean‐12‐en‐28‐oic acid ( 4 ) were isolated from the acetone‐insoluble fraction obtained from the 80% aqueous MeOH extract of Albizia anthelmintica Brongn . leaves. Their structures were identified using different NMR experiments including: ¹H‐ and ¹³C‐NMR, HSQC, HMBC and ¹H,¹H‐COSY, together with HR‐ESI‐MS/MS, as well as by acid hydrolysis. The four isolated saponins and the fractions of the extract exhibited cytotoxic activity against HepG‐2 and HCT‐116 cell lines. Compound 2 showed the most potent cytotoxic activity among the other tested compounds against the HepG2 cell line with an IC₅₀ value of 3.60μm . Whereas, compound 1 showed the most potent cytotoxic effect with an IC₅₀ value of 4.75μm on HCT‐116 cells.     

小花盾叶薯蓣甙的酶降解

从小花盾叶薯蓣(Dioscorea parviflora C. T. Ting)的新鲜根状茎中分离到一个新的呋甾烷型配糖体,命名为小花盾叶薯蓣甙(parvifloside) (1),其结构通过波谱和化学方法鉴定为:(25R)-26-O-β-glucopyranosyl-furost-5-en-3β, 22ξ, 26-triol 3-O-β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl (1→4)-[α-L-rhamnopyranosyl (1→2)]-β-D-glucopyranoside.化合物1在纤维素酶粗酶和β-葡萄糖苷酶中进行水解,得到降解产物2-7.对1的酶解现象进行了讨论.同时,对所分离的甾体皂甙的抗稻瘟霉菌活性进行了初步筛选.