New steroidal glycosides from the fruits of Tribulus terrestris

Three new steroidal saponins (1-3) were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic methods (IR, HRESIMS, 1D- and 2D-NMR) as 26-O-beta-D-glucopyranosyl-(25S)-5beta-furost-20(22)-en-3bet a, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl- (1-->4)]-beta-D-glucopyranoside (1), 26-O-beta-D-glucopyranosyl-(25S)-5beta-furost-20(22)-en-3bet a, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1 -->4)]-beta-D-galactopyranoside (2), and 25(S)-5beta-spirostan-3beta-ol-3-O-alpha-L-rhamnopyranosyl-( 1-->2)-[b eta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside (3). Compound 3 showed cytotoxicity against a human malignant melanoma cell line (SK-MEL).     

Four new dammarane saponins from Zizyphus lotus

Five dammarane-type saponins were isolated by means of centrifugal partition chromatography from the leaves of Zizyphus lotus. Their structures were elucidated using a combination of 1D and 2D 1H and 13C NMR spectra and mass spectroscopy. One of these glycosides is the known jujuboside B (5). Three are new jujubogenin glycosides, identified as 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyljujubogenin-20-O-(2,3,4-O-triacetyl)-alpha-L-rhamnopyranoside (1), 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyljujubogenin-20-O-alpha-L-rhamnopyranoside (2), and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[(4-sulfo)-beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyljujubogenin (3). The last is a new sulfated derivative of jujubasaponine IV, identified as 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[(4-sulfo)-beta-D-glucopyranosyl-(1-->3)]-beta-D-galactopyranosyl-(20R,22R)-16beta,22:16alpha,30-diepoxydammar-24-ene-3beta,20-diol (4).     

Three new acylated triterpene saponins from Acanthophyllum squarrosum

Three new triterpenoid saponins, 1-3, were isolated from the roots of Acanthophyllum squarrosum. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-3-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-3,4-di-O-acetyl-beta-D-fucopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[5-O-acetyl-alpha-L-arabinofuranosyl-(1-->3)]-4-O-acetyl-beta-D-fucopyranoside (2), and 3-O-beta-D-glucopyranosyl-quillaic acid-28-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (3).     

Two new biologically active triterpene saponins from Acanthophyllum squarrosum

Two novel triterpenoid saponins (1 and 2) have been isolated from the roots of Acanthophyllum squarrosum. The structures were established mainly by a combination of 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-be ta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3 )-b eta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L- rhamnopyranosyl-(1-->3)]-beta-D-fucopyranoside (1) and 3-O-beta-D-glucopyranosylgypsogenin-28-O-alpha-L-rhamnopyranosyl-( 1-- >2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6 )]- beta-D-glucopyranoside (2). Compound 1 showed a moderate concentration-dependent immunomodulatory effect in an in vitro lymphocyte proliferation assay.     

Activity of triterpenoid glycosides from the root bark of Mussaenda macrophylla against two oral pathogens.

Four new triterpenoid glycosides were isolated from the root bark of Mussaenda macrophylla. Their structures were determined as 3-O-beta-D-glucopyranosyl-28-O-alpha-L-rhamnopyranosyl-16alpha- hydrox y-23-deoxyprotobassic acid (1), 28-O-beta-D-glucopyranosyl-16alpha-hydroxy-23-deoxyprotobassic+ ++ acid (2), 3-O-beta-D-glucopyranosyl-28-O-alpha-L-rhamnopyranosyl-16alpha- hydrox yprotobassic acid (3), and 3-O-?[beta-D-glucopyranosyl-(1-->6)]-O-alpha-L-rhamnopyranosyl-(1-->2 )-O-beta-D-glucopyranosyl-(1-->2)?-O-beta-D-glucopyranosyl-(1-->3)-O- beta-D-glucopyranosyl-cycloarta-22,24-dien-27-oic acid (mussaendoside W, 4). Four known triterpenoids [3-O-acetyloleanolic acid (5), 3-O-acetyldaturadiol (6), rotundic acid (7), and 16alpha-hydroxyprotobassic acid (8)] were also isolated. The structures of 1-4 were determined by several spectroscopic techniques including 2D NMR methods. Compounds 1-6 showed inhibitory activity against a periodontopathic bacterium, Porphyromonas gingivalis, but were inactive against the cariogenic organism, Streptococcus mutans.     

Saponarioside C, the first alpha-D-galactose containing triterpenoid saponin, and five related compounds from Saponaria officinalis

Six novel triterpenoid saponins, named saponariosides C-H, were isolated from the whole plants of Saponaria officinalis. Their structures were established as saponarioside C (1), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-alpha-D-galactopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-- >6)-[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside D (2), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside E (3), 3-O-beta-D-glucopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside F (4), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside G (5), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1-->3 )]-beta-D-glucopyranoside; and saponarioside H (6), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranoside, by a combination of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC, and NOESY) studies and chemical degradation.     

安徽银莲花的化学成分研究

目的 :对安徽银莲花根茎的化学成分进行分离、鉴定。方法 :大孔树脂柱、硅胶柱和ODS柱色谱分离 ,FAB MS和NMR技术确定结构。结果和结论 :分离鉴定了 3个化合物 ,齐墩果酸28-O-α-L-吡喃鼠李糖-(1→4)-β-D-吡喃葡萄糖-(1→6)-β-D-吡喃葡萄糖酯苷 ;3-O-α-L-吡喃鼠李糖 (1→ 2)-β-D-吡喃木糖齐墩果酸-28-O-α-L-吡喃鼠李糖 (1→4)-β-D-吡喃葡萄糖 (1→6)-β-D-吡喃葡萄糖酯苷和-3-O-β-D-吡喃葡萄糖 (1→2)-β-D-吡喃木糖齐墩果酸-28-O-α-L-吡喃鼠李糖 (1→4)-β-D-吡喃葡萄糖 (1→6)-β-D-吡喃葡萄糖酯苷 ;均为首次从本植物中分离得到。     

Oleanane saponins in "kancolla", a sweet variety of Chenopodium quinoa

Seven triterpenoid saponins were isolated from the seeds of "kancolla", a sweet variety of Chenopodium quinoa. Their structures were phytolaccagenic acid 3-O-[alpha-L-arabinopyranosyl-(1' '-->3')-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside, oleanolic acid 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside, hederagenin 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside, phytolaccagenic acid 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside, oleanolic acid 3-O-[beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside, oleanolic acid 3-O-[alpha-L-arabinopyranosyl-(1'-->3')-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside, and the new compound serjanic acid 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside (1). The structure of 1 was characterized on the basis of spectroscopic and chemical evidence.     

Two new spirostanol saponins from Allium tuberosum.

Two new spirostanol saponins, tuberosides D and E, have been isolated from the seeds of Allium tuberosum. On the basis of spectral data and chemical reactions, their structures were established as (25S)-5alpha-spirostane-2alpha,3beta-diol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-[alpha-L-rhamnopyranosyl-(1-->4 )]-O-beta-D-glucopyranoside and (25S)-5alpha-spirostan-2alpha, 3beta-diol 3-O-beta-D-glucopyranosyl-(1-->2)-O-[alpha-L-rhamnopyranosyl-(1-->4)] -O-beta-D-glucopyranoside, respectively.     

卷丹化学成分研究

目的：研究卷丹Lilium lancifolium鳞茎中的化学成分。方法：用色谱法分离卷丹的化学成分,用波谱法鉴定其结构。结果：从卷丹中分离并鉴定了10个化合物,分别为王百合苷A(1),王百合苷C(2),甲基-α-D-吡喃甘露糖苷(3),甲基-α-D-吡喃葡萄糖苷(4),(25R,26R)-26-甲氧基螺甾烷-5-烯-3β-O-α-L-吡喃鼠李糖-(1→2)-［β-D-吡喃葡萄糖-(1→6)］-β-D-吡喃葡萄糖苷(5),(25R)-螺甾烷-5-烯-3β-O-α-L-吡喃鼠李糖-(1→2)-［β-D-吡喃葡萄糖-(1→6)］-β-D-吡喃葡萄糖苷(6),(25R,26R)-17α-羟基-26-甲氧基螺甾烷-5-烯-3β-O-α-L-吡喃鼠李糖-(1→2)-［β-D-吡喃葡萄糖-(1→6)］-β-D-吡喃葡萄糖苷(7),胡萝卜苷(8),腺嘌呤核苷(9),小檗碱(10)。结论：除化合物1,3外均为首次从该植物中分离得到,其中10为首次从百合属植物中发现。     

Oleanane and taraxerane glycosides from the roots of Gomphrena macrocephala

Phytochemical screening of the roots of Gomphrena macrocephala, with particular attention to its triterpene glycoside constituents, has resulted in the isolation of two new oleanane glycosides (1 and 2) and a new taraxerane glycoside (3). The structures of 1-3 were determined as 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]olean-28,13-olide (1), 11alpha,12alpha-epoxy-3beta-[(O-beta-D-galactopyranosyl-(1-->3)-O-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl)-oxy]olean-28,13-olide (2), and 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]taraxer-14-en-28-oic acid beta-D-glucopyranosyl ester (3), respectively, on the basis of their spectroscopic data and the results of hydrolysis. The aglycones (1a and 3a) of 1-3 with an epoxy group showed cytotoxic activity against HSC-2 human oral squamous carcinoma cells.     

A new pregnane glycoside from Dioscorea collettii var. hypoglauca

During further bioactivity-guided fractionation, a new pregnane glycoside, hypoglaucin G (1), and a known compound, pregna-5, 16-dien-3beta-ol-20-one 3-O-alpha-L-rhamnopyranosyl-(1-->2)- [alpha-L-rhamnopyranosyl-(1-->4)] -beta-D-glucopyranoside (2), were isolated from the EtOH extract of Dioscorea collettii var. hypoglauca rhizomes, which induced morphological deformation of Pyricularia oryzae mycelia with minimum morphological deformation concentration values of 135 microM and 236 microM, respectively. The structure of 1 was established as 16beta-(4'-methyl-5'-O-beta-D-glucopyranosyl- pentanoxyl)-pre gn-5-en-3 beta-ol-20-one 3-O-alpha-L- rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D- glucopyranoside on the basis of chemical evidence and spectral analysis, especially by 2D NMR techniques.     

Acylated preatroxigenin glycosides from Atroxima congolana

Six new acylated bisdesmosidic preatroxigenin saponins named atroximasaponins E1, E2 (1, 2), F1, F2 (3, 4), and G1, G2 (5, 6) were isolated as three inseparable mixtures of the trans- and cis-p-methoxycinnamoyl derivatives, from the roots of Atroxima congolana. Their structures were established through extensive NMR spectroscopic analysis as 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin E1, 1), and its cis-isomer, atroximasaponin E2 (2), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin F1, 3), and its cis-isomer, atroximasaponin F2 (4), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-apiofuranosyl-(1-->3)-[alpha-l-rhamnopyranosyl-(1-->2)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin G1, 5), and its cis-isomer, atroximasaponin G2 (6), respectively.     

Biologically active triterpene saponins from callus tissue of Polygala amarella.

A new bioactive saponin (1), together with a known saponin (polygalasaponin XXVIII) has been isolated from the callus tissue culture of Polygala amarella. Based on spectroscopic data, especially direct and long-range heteronuclear 2D NMR analysis and on chemical transformations, the structure of 1 was elucidated as 3-O-beta-D-glucopyranosyl presenegenin-28-O-beta-D-galactopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-fucopyranoside. Both saponins showed significant immunological properties based on the enhancement of granulocyte phagocytosis in vitro.     

Monoterpene glycosides and triterpene acids from Eriobotrya deflexa

A phytochemical study on a methanolic extract of leaves of Eriobotrya deflexa led to the isolation and characterization of nine terpenoid compounds. Four of these are new chemical entities, including two monoterpene glycosides, (3S)-O-alpha-L-rhamnopyranosyl-(1-->3)-[4-O-(E)-coumaroyl]-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyl-linalool (1) and (3S)-O-alpha-L-rhamnopyranosyl-(1-->3)-[4-O-(Z)-coumaroyl]-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyl-linalool (2), and two triterpene acids, 1beta,2alpha,19alpha-trihydroxy-3-oxo-12-ursen-28-oic acid (3) and 2alpha,3alpha,19alpha-trihydroxy-12-oleanen-28-oic acid (4). Their structures were elucidated on the basis of spectroscopic analysis. The activities of these isolates in an in vitro antiproliferation test were also determined.     

Antioxidant flavan-3-ols and flavonol glycosides from Maytenus aquifolium

TLC autographic assay revealed, in the EtOAc extract obtained from leaves and root bark of Maytenus aquifolium (Celastraceae), the presence of fi ve compounds exhibiting antioxidant properties towards beta-carotene. They were isolated and identified as epigallocatechin (1), (+) ouratea-catechin (2), proanthocyanidin (3), kaempferol 3-O-alpha-L-rhamnopyranosyl (1-->6)-O-[beta-D-glucopyranosyl (1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)]-O-beta-D-glucopyranosyl (4) and quercetin 3-O-alpha-L-rhamnopyranosyl (1-->6)-O-[beta-D-glucopyranosyl (1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)]-O-beta-D-glucopyranosyl (5). The isolates were investigated for their redox properties using cyclic voltammetry and for their radical scavenging abilities through spectrophotometric assay on the reduction of 2,2-diphenyl-pycryl hydrazyl (DPPH). These results were correlated to the inhibition of beta-carotene bleaching on TLC autographic assay and to structural features of the flavonoids.     

Triterpene glycosides from the roots of Astragalus flavescens

Six new triterpene saponins, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-epi-kudzusapogenol A (1), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-epi-kudzusapogenol A (2), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-22-O-beta-D-glucopyranosyl-21-epi-kudzusapogenol A (3), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-22-O-beta-D-glucopyranosyl-21-epi-kudzusapogenol A (4), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-22-O-alpha-L-arabinopyranosyl-21-epi-kudzusapogenol A (5), and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-22-O-alpha-L-arabinopyranosyl-21-epi-kudzusapogenol A (6), were isolated from the roots of Astragalus flavescens, together with the known trajanoside B, azukisaponin V, and astragalosides IV, VII, and VIII. Their structures were established mainly by 2D NMR techniques and mass spectrometry.     

Triterpenoid saponins from the roots of Pulsatilla koreana

Six new saponins, five lupanes (1-5) and one oleanane (6), along with 11 known saponins, were isolated from the roots of Pulsatilla koreana. The structures of the new saponins were found to be 23-hydroxy-3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (1), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (2), 3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (3), 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (4), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->4)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (5), and hederagenin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (6). Their structures were determined on the basis of 1D and 2D NMR ((13)C NMR, (1)H NMR, (1)H-(1)H COSY, HMQC, and HMBC) methods, FABMS, and hydrolysis. All isolated compounds were evaluated for their cytotoxic activity against A-549 human lung carcinoma cells.     

槐花炭化学成分的研究

目的:研究中药槐花炭的化学成分。方法:用硅胶柱色谱法和光谱分析法分离和鉴定化学成分。结果:分得6个化合物,经光谱分析鉴定其结构分别为麦芽酚(1),3-羟基吡啶(2),麦芽酚-3-氧-[6′-氧-(4″-羟基-反式-桂皮酰基)]-β-D-吡喃葡萄糖苷(3),3-氧-[β-D-半乳吡喃糖基-(1→2)-p-β-葡萄吡喃醛酸糖基]槐二醇乙酯(4),3-氧-[β-D-半乳吡喃糖基.(1→2)-β-D-葡萄吡喃醛酸糖基]槐二醇甲酯(5),芦丁(6)。结论:化合物4为新化合物,化合物1,2,3,5为首次从槐花炭中获得。     

Four new triterpenoid saponins from Conyza blinii

Three new bisdesmosidic saponins named conyzasaponins A, B, and C (1-3) and one new monodesmosidic saponin, conyzasaponin G (4), were isolated from the aerial parts of Conyza blinii. Their structures were elucidated on the basis of extensive NMR (DEPT, DQF-COSY, HOHAHA, HMQC, HMBC, and NOESY) and MS studies. Compounds 1-3 share a common prosapogenin, bayogenin 3-O-beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside, which is identical with conyzasaponin G (4), and differ in the structures of the ester-linked sugar moieties at C-28. Conyzasaponin A (1) is the 28-O-beta-D-apiofuranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester, conyzasaponin B (2), the 28-O-beta-D-apiofurano- syl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester, and conyzasaponin C (3), the 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester of the prosapogenin, respectively.