Isolation and structure of five new cancer cell growth inhibitory bufadienolides from the Chinese traditional drug Ch'an Su

Five new bufadienolides, 3beta-formyloxyresibufogenin (1), 19-oxobufalin (2), 19-oxodesacetylcinobufagin (3), 6alpha-hydroxycinobufagin (4), and 1beta-hydroxybufalin (5), have been isolated together with the previously known bufadienolides 6-20 from the Chinese traditional drug "Ch'an Su". The structures were elucidated employing spectroscopic methods. Bufadienolides 1-5 provided significant inhibitory activity against the KB and HL-60 cancer cell lines. In addition, bufadienolide 1 was found active against the MH-60 cancer cell line.     

Inhibitory effects of bufadienolides on interleukin-6 in MH-60 cells

Derivatives of bufogenin isolated from the skin of the Chinese toad, Bufo bufo gargarizans Cantor ("Ch'an Su"), and several semisynthetic derivatives of 20beta,21beta-epoxy-resibufogenin (13) have been evaluated for interleukin-6 (IL-6) antagonistic activity due to their growth-inhibitory activities on IL-6-dependent MH-60 cells. Among the naturally derived compounds (1-17), 20S,21-epoxy-resibufogenin formate (1) showed potent inhibitory activity on the IL-6-dependent growth of MH-60 cells. Epoxide groups at both the C-14, C-15 and C-20, C-21 positions are required to exhibit this type of activity. Compounds acetylated at the C-16 position (7 and 9-11) showed a loss of activity. An oxo group at the C-3 position (8, 14, and 15) resulted in cytotoxicity for both cell lines. Stereochemistry is important for selectivity on suppression of IL-6 activity. Among the semisynthetic derivatives (18-25) of 13, compound 19, with an acetyl group introduced at the C-3 position in comparison to 13, demonstrated considerable growth inhibition of IL-6-dependent MH-60 cells.     

Triterpene glycosides from Cimicifuga racemosa

Eight new triterpene glycosides named cimiracemosides A-H, respectively, and eight known triterpene glycosides were isolated from the rhizome extracts of black cohosh (Cimicifuga racemosa). The new compounds were determined by spectral data to be 21-hydroxycimigenol-3-O-alpha-L-arabinopyranoside (1), 21-hydroxycimigenol-3-O-beta-D-xylopyranoside (2), cimigenol-3-O-alpha-L-arabinopyranoside (3), 12beta-acetoxycimigenol-3-O-alpha-L-arabinopyranoside (4), 24-acetylisodahurinol-3-O-beta-D-xylopyranoside (5), 20(S),22(R), 23(S),24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3be ta,23, 24-trihydroxy-9,19-cycloanost-7-ene-3-O-beta-D-xylopyranoside (6), 20(S),22(R),23(S),24(R)-16beta:23;22:25-diepoxy-12beta -acetoxy-3beta, 23,24-trihydroxy-9,19-cycloanost-7-en-3-O-alpha-L-arabinopyrano side (7), and 20(S),22(R),23(S), 24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3beta,23, 24-trihydroxy-9,19-cycloanostane-3-O-beta-D-xylopyranoside (8).     

A New Triterpene Saponin from Gynostemma pentaphyllum

Objective To study the triterpene saponins from Gynostemma pentaphyllum with antitumor activities. Methods The 75% EtOH extract of G. pentaphyllum was used for isolation by silica gel column chromatography and preparative HPLC. The structures of pure compounds isolated were identified by the spectral analysis and chemical evidence. Results Two compounds were isolated and identified as 23(S)-3β,20ξ,21ξ-trihydroxy-19-oxo-21,23-epoxydammar-24-ene 3-O-α-L-rhamnopyranosyl (1→2)-[β-D-xylopyranosyl (1→3)]-β-D-arab...     

Neoclerodane diterpenoids from Croton eluteria

Five new neoclerodane diterpenoids, rel-(3R,4S,5R,7R,8S,9R,10S,12R,20S)-7-acetoxy-15,16,12,20-diepoxy-3,4-dihydroxy-20-methoxyneocleroda-13(16),14-diene (1), rel-(3R,4S,5R,7R,8S,9R,10S,12R,20S)-7-acetoxy-15,16,12,20-diepoxy-3,4,20-trihydroxyneocleroda-13(16),14-diene (2), rel-(3R,4S,5S,6R,7S,8S, 9R,10S,12R,20S)-6,7-diacetoxy-3,4,15,16,12,20-triepoxy-20-hydroxyneocleroda-13(16),14-diene (3), rel-(3R,4S,5R,7R,8S,9R,10S,12R,20S)-7-acetoxy-3,4,15,16,12,20-triepoxy-20-hydroxyneocleroda-13(16),14-diene (4), and rel-(3R,4S,5R,7R,8S,9R,10S,12R,20R)-7,20-diacetoxy-3,4,15,16,12,20-triepoxyneocleroda-13(16),14-diene (5), have been isolated from the bark of Croton eluteria. The structures of the compounds 1-5 (cascarillins E-I) were determined by spectroscopic data interpretation.     

New lanostanoids of Ganoderma tsugae

Three new compounds, (24R, S)-3alpha-acetoxy-24-hydroxy-5alpha-lanosta-8,25-di en-21-oic acid, named tsugaric acid C (1); 3alpha-acetoxy-5alpha-lanosta-8, 24-diene-21-O-beta-D-xyloside, named tsugarioside B (2); and 3alpha-acetoxy-(Z)-24-methyl-5alpha-lanosta-8,23,25-tr ien-21-oic acid ester beta-D-xyloside, named tsugarioside C (3), and a mixture of two known steroids were isolated from the fruit bodies of Ganoderma tsugae. The structures of 1-3 were determined by spectral and chemical methods. The cytotoxic activity of the lanostanoid constituents of this fungus was evaluated against several different cancer cell lines.     

Hemolytic steroid disulfates from the far eastern starfish Pteraster pulvillus

Six steroidal ophiuroid-type disulfates, namely, disodium salts of (20R)-cholest-5-ene-3alpha,4beta,21-triol 3, 21-disulfate (1), (20R)-5alpha-cholestane-3alpha,4beta,21-triol 3,21-disulfate (2), (20R)-5alpha-cholestane-2beta,3alpha,21-triol 3,21-disulfate (3), and (20R)-5alpha-cholestane-3alpha,21-diol 3,21-disulfate (4), the dityrammonium salt of (20R)-5alpha-cholestane-3alpha,21-diol 3,21-disulfate (5), and a mixture of sodium and tyrammonium salts (1:1) of (20R)-cholest-5-ene-3alpha,21-diol 3,21-disulfate (6), have been isolated from the ethanolic extracts of Far Eastern starfish Pteraster pulvillus. Steroids 2 and 3 are new compounds. Steroids 1, 2, and 4-6 showed hemolytic activity to mouse erythrocytes with HC(50) values of 8.0 x 10(-5), 4.5 x 10(-5), 1.0 x 10(-5), 1.8 x 10(-5), and 3.3 x 10(-5) M, respectively.     

红藻扇形叉枝藻中的降碳倍半萜及其衍生物

目的：对红藻扇形叉枝藻Gymnogongrus flabelliformis进行化学成分研究。方法：利用正相和反相硅胶柱色谱、Sephadex LH-20凝胶柱色谱和反相HPLC等手段进行分离纯化,借助MS,1D和2D NMR等波谱方法鉴定化合物结构；通过MTT法对分离鉴定的单体化合物在人肺癌细胞株(A549)、人肝癌细胞株(Bel 7402)、人胃癌细胞株(BGC 823)、人结肠癌细胞株(HCT-8)和人卵巢癌细胞株(A2780)上进行肿瘤细胞毒活性筛选。结果：从红藻扇形叉枝藻中分离得到5个降碳倍半萜类化合物,分别鉴定为(3S,6R,7E)-(+)-3-hydroxyl-4,7-megastigmadien-9-one(1),(3S,5R,6S,7E)-(-)-3-hydroxy-5,6-epoxy-7-megastig-mene-9-one(2),(3S,5S,6R,7E)-(+)3-hydroxy-5,6-epoxy-7-megastigmene-9-one(3),dehydrovomifoliol(4)和(3R)-(-)-4-［(2R,4S)-4-acetoxy-2-hydroxy-2,6,6-trimethylcyclohexylidene］-3-buten-2-one(5)。结论：以上化合物均为首次从该属海藻中分离得到,其中化合物1为新天然产物。细胞毒活性试验结果显示所有化合物在10 μg·mL^-1均无明显细胞毒活性。     

杂交贝母生物碱成分的研究

目的 :对杂交贝母进行化学成分研究。方法 :采用IR ,¹H NMR ,¹³ C-NMR ,2D-NMR ,MS及与对照品和文献对照等方法鉴定结构。结果 :分离并鉴定了 7个化合物 :湖贝乙素 (hupehenirine ,ZF1) ;湖贝嗪 (hupehenizine ,ZF2 ) ;浙贝乙素 (peiminine ,verticinone ,ZF3) ;湖贝甲素 (hupehenine ,ZF4 )、异浙贝甲素 (isoverticinone ,ZF5 )、浙贝甲素(peimine ,verticine ,ZF6 )、湖贝甲素苷 (hupeheninoside,ZF7) ;结论 :化合物 1～ 7均为首次从杂交贝母中得到。     

Terpene isocyanides, isocyanates, and isothiocyanates from the Okinawan marine sponge Stylissa sp

Seven new nitrogenous terpenoids, (1R,6R,7S,10S)-10-isothiocyanatocadin-4-ene (1), (1S,2S,5S,6S,7R,8S)-13-isothiocyanatocubebane (2), (1R,3S,4R,7S,8S,12S,13S)-7-isocyanoamphilecta-10,14-diene (3), (1S,3S,4R,7S,8S,12S,13S)-8-isocyanoamphilecta-11(20),14-diene (4), (3S,4R,7S,8S,11S,13S)-8-isocyanoamphilecta-1(12),14-diene (5), 8-isocyanatocycloamphilect-10-ene (6), and 8-isothiocyanatocycloamphilect-10-ene (7), were isolated from the Okinawan sponge Stylissasp., along with 12 known related compounds. Structural determinations of these compounds were made by spectroscopic analysis, and assessment was made of their cytotoxicity toward HeLa cells.     

Cadinane sesquiterpenes from the brown alga Dictyopteris divaricata

Seven new cadinane sesquiterpenes, (-)-(1R,6S,7S,10R)-1-hydroxycadinan-3-en-5-one (1), (+)-(1R,5S,6R,7S, 10R)-cadinan-3-ene-1,5-diol (2), (+)-(1R,5R,6R,7S,10R)-cadinan-3-ene-1,5-diol (3), (+)-(1R,5S,6R,7S,10R)-cadinan-4(11)-ene-1,5-diol (4), (+)-(1R,5R,6R,7R,10R)-cadinan-4(11)-ene-1,5,12-triol (5), (-)-(1R,4R,5S,6R,7S, 10R)-cadinan-1,4,5-triol (6), and (-)-(1R,6R,7S,10R)-11-oxocadinan-4-en-1-ol (7), together with nine known compounds were isolated from the brown alga Dictyopteris divaricata. The structures of the new natural products, as well as their absolute configuration, were established by means of spectroscopic data including IR, HRMS, 1D and 2D NMR, single-crystal X-ray diffraction, and CD. All compounds were inactive against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), breast cancer (MCF-7), hepatoma (Bel7402), and colon cancer (HCT-8) cell lines.     

Spiranoid withanolides from Jaborosa odonelliana

Six new spiranoid withanolides, (20R,22R,23S)-5alpha-chloro-6beta,12beta,17beta,22-tetrahydroxy-1-oxo-12,23-cycloergosta-2,24-dien-26,23-olide (2), (20R,22R,23S)-5beta,6beta-epoxy-12beta,17beta,22-trihydroxy-1-oxo-12,23-cycloergosta-2,24-dien-26,23-olide (3), (20R,22R,23S)-5beta,6beta-epoxy-4beta,12beta,17beta,22-tetrahydroxy-1-oxo-12,23-cycloergosta-2,24-dien-26,23-olide (4), (20R,22R,23S)-5alpha,6beta,12beta,17beta,22-pentahydroxy-1-oxo-12,23-cycloergosta-2,24-dien-26,23-olide (5), (20R,22R,23S)-6beta,12beta,17beta,22-tetrahydroxy-5alpha-methoxy-1-oxo-12,23-cycloergosta-2,24-dien-26,23-olide (6), and (20R,22R,23S)-6beta,12beta,17beta,22-tetrahydroxy-2alpha,5alpha-epidioxy-1-oxo-12,23-cycloergosta-3,24-dien-26,23-olide (7), were isolated from the leaves of Jaborosa odonelliana. Compounds 2-7 were characterized by a combination of spectroscopic methods (1D and 2D NMR, MS) and molecular modeling.     

Three new triterpenes from Nerium oleander and biological activity of the isolated compounds

New ursane-type triterpene 1, oleanane-type triterpene 2, and dammarane-type triterpene 15 were isolated from the leaves of Nerium oleander together with 12 known triterpenes, 3beta-hydroxy-12-ursen-28-oic acid (ursolic acid, 3), 3beta,27-dihydroxy-12-ursen-28-oic acid (4), 3beta,13beta-dihydroxyurs-11-en-28-oic acid (5), 3beta-hydroxyurs-12-en-28-aldehyde (6), 28-norurs-12-en-3beta-ol (7), urs-12-en-3beta-ol (8), urs-12-ene-3beta,28-diol (9), 3beta-hydroxy-12-oleanen-28-oic acid (oleanolic acid, 10), 3beta,27-dihydroxy-12-oleanen-28-oic acid (11), 3beta-hydroxy-20(29)-lupen-28-oic acid (betulinic acid, 12), 20(29)-lupene-3beta,28-diol (betulin, 13), and (20S,24R)-epoxydammarane-3beta,25-diol (14). On the basis of their spectroscopic data, the structures of the new compounds 1, 2, and 15 were established as 3beta,20alpha-dihydroxyurs-21-en-28-oic acid, 3beta,12alpha-dihydroxyoleanan-28,13beta-olide, and (20S,24S)-epoxydammarane-3beta,25-diol, respectively. The anti-inflammatory activity of the seven isolated compounds and methyl esters of ursolic acid and oleanoic acid in vitro was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). The anticancer activity of the 14 isolated compounds, including 1, 2, 15, and methyl esters of ursolic acid and oleanolic acid in vitro was examined on the basis of the cell growth inhibitory activities toward three kinds of human cell lines.     

紫花地丁全草化学成分研究

目的研究紫花地丁Viola yedoensis全草的化学成分。方法采用硅胶、ODS、Sephadex LH-20凝胶和半制备型高效液相等柱色谱方法进行分离纯化,通过理化性质结合NMR、MS等谱学数据分析鉴定化合物结构。结果从紫花地丁95%乙醇提取物中分离得到21个化合物,分别鉴定为秦皮乙素-6-O-β-D-呋喃芹糖基-(1→2)-β-D-吡喃葡萄糖苷(1)、吲哚-3-甲酸乙酯(2)、脱氢地芰普内酯(3)、滨蒿内酯(4)、蒲公英苦素(5)、水杨苷(6)、丁香苷(7)、4-羟基-4-[3′-(β-D-葡萄糖基)亚丁基]-3,5,5-三甲基-2-环己烯-1-醇(8)、柑橘苷A(9)、(7S,8R)-二氢去氢二松柏醇-9-O-β-D-吡喃葡萄糖苷(10)、山柰素-3-O-α-L-(4-O-乙酰基)鼠李糖基-7-O-α-L-鼠李糖苷(11)、山柰酚-7-O-α-L-鼠李糖苷(12)、山柰酚-3-O-α-L-鼠李糖苷(13)、山柰酚-3-O-α-L-鼠李糖基-7-O-α-L-鼠李糖苷(14)、山柰酚-3-O-β-D-葡萄糖苷(15)、芹菜素(16)、(+)-异地芰普内酯(17)、尿苷(18)、腺苷...     

Cytotoxic withaphysalins from the leaves of Acnistus arborescens

Three withaphysalins, rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-1,18-dioxowitha-2,24-dienolide(withaphysalin M) (1), rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-18-ethoxy-1-oxowitha-2,24-dienolide (withaphysalin F ethyl ether, withaphysalin O) (2), and rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-1,18-dioxowitha-24-enolide (withaphysalin N) (3), were isolated from the leaves of Acnistus arborescens. The structures were deduced from 1D ((1)H NMR, (13)C NMR, DEPT-(13)C NMR) and 2D (COSY, HMQC, HMBC) NMR analysis and the relative stereochemical assignments based on 1D NOESY correlations and analysis of coupling constants. Compounds 1 and 2 displayed potent cytotoxic activity against a panel of human cancer cell lines.     

Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea

Three 20(S)-protopanaxatriol-type saponins, ginsenoside-Rg1 (1), notoginsenoside-R1 (2), and ginsenoside-Re (3), were transformed by the fungus Absidia coerulea (AS 3.3389). Compound 1 was converted into five metabolites, ginsenoside-Rh4 (4), 3beta,2beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-beta-D-glucopyranoside (5), 20(S)-ginsenoside-Rh1 (6), 20(R)-ginsenoside-Rh1 (7), and a mixture of 25-hydroxy-20(S)-ginsenoside-Rh1 and its C-20(R) epimer (8). Compound 2 was converted into 10 metabolites, 20(S)-notoginsenoside-R2 (9), 20(R)-notoginsenoside-R2 (10), 3beta,12beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (11), 3beta,12beta-dihydroxydammar-(E)-20(22),24-diene-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (12), 3beta,12beta,20,25-tetrahydroxydammaran-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (13), and compounds 4-8. Compound 3 was metabolized to 20(S)-ginsenoside-Rg2 (14), 20(R)-ginsenoside-Rg2 (15), 3beta,12beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (16), 3beta,12beta-dihydroxydammar-(E)-20(22),24-diene-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (17), 3beta,12beta,20,25-tetrahydroxydammaran-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (18), and compounds 4-8. The structures of five new metabolites, 10-13 and 16, were established by spectroscopic methods.     

Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata

Five minor sesquiterpenes (1-5) with two novel carbon skeletons, together with a minor new oplopane sesquiterpene (6), have been isolated from the brown alga Dictyopteris divaricata. By means of spectroscopic data including IR, HRMS, 1D and 2D NMR, and CD, their structures including absolute configurations were assigned as (+)-(1R,5S,6S,9R)-3-acetyl-1-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0]non-3-ene (1), (+)-(1R,3S,4S,5R,6S,9R)-3-acetyl-1,4-dihydroxy-6-isopropyl-9-methylbicyclo[4.3.0]nonane (2), (+)-(1R,3R,4R,5R,6S,9R)-3-acetyl-1,4-dihydroxy-6-isopropyl-9-methylbicyclo[4.3.0]nonane (3), (+)-(1S,2R,6S,9R)-1-hydroxy-2-(1-hydroxyethyl)-6-isopropyl-9-methylbicyclo[4.3.0]non-4-en-3-one (4), (-)-(5S,6R,9S)-2-acetyl-5-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0]non-1-en-3-one (5), and (-)-(1S,6S,9R)-4-acetyl-1-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0]non-4-en-3-one (6). Biogenetically, the carbon skeletons of 1-6 may be derived from the co-occurring cadinane skeleton by different ring contraction rearrangements. Compounds 1-6 were inactive (IC(50) > 10 mug/mL) against several human cancer cell lines.     

宽叶羌活种子的化学成分

目的:研究宽叶羌活种子的化学成分。方法:利用正、反相柱色谱及薄层制备色谱等方法对宽叶羌活种子乙醇提取物进行分离和纯化,通过MS,NMR等波谱解析技术鉴定其结构。结果:从宽叶羌活种子的乙醇提取物中共分离鉴定了29个化合物,分别为异欧前胡素(1)、β-谷甾醇(2)、珊瑚菜内酯(3)、佛手柑内酯(4)、N-二十四、二十六、二十八烷酰基邻氨基苯甲酸(5～7)、胡萝卜苷(8)、水和氧化前胡素(9)、伞形花内酯(10)、去甲呋喃羽叶芸香素(11)、(2S,3S,4R,8E)-2-[(2’R)-2’-羟基-二十二、二十三、二十四、二十五、二十六碳酰胺]-8-十八碳烯-1,3,4-三醇(12～16)、左旋氧化前胡素(17)、香叶木素(18)、佛手酚-O-β-D-葡萄糖苷(19)、紫花前胡苷(20)、1’-O-β-D-葡萄糖基-(2R,3S)-3-羟基紫花前胡苷元(21)、尿嘧啶(22)、前胡苷V(23)、8-O-β-D-葡萄糖基-5-羟基-补骨脂素(24)、8-O-β-D-葡萄基-5-甲氧基补骨脂素(25)、香叶木苷(26)、阿拉善苷C(27)、犬尿喹酸(28)、甘露醇(29)。结论:以上化合物均为首次从该植物种子中分离得到,化合物18,22,26,29为首次从该属植物中分离得到。     

三角叶凤毛菊中类异戊二烯和苯丙素类化学成分

目的:研究菊科药用植物三角叶凤毛菊Saussurea deltoidea的化学成分.方法:利用正/反相硅胶柱层析色谱、凝胶分子筛色谱、HPLC等色谱方法进行化合物的分离,利用波谱学方法鉴定化合物结构.结果:从三角叶凤毛菊中分离出10个化合物,其结构分别鉴定为(3R,6R,7E)-3-hydroxy-4,7 -megastigmadien-9 -one(1),(3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (2),3 -h ydroxy-β-damascone(3),S-(+)-dehydrovomifoliol(4),megastigman-5 -ene-3β,9R-diol(5),coniferaldehyde(6),β-hydroxypropiovanillone (7),3-hydroxy-1- (4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (8),dihydrosyringenin(9),4-[(1S)-3-hydroxy-1-methoxypropyl]-2,6-dimenthoxyphenol( 10).结论:化合物1～10均是首次从该植物中分离得到.     

Beesiosides A-F, six new cycloartane triterpene glycosides from Beesia calthaefolia.

Six new cycloartane triterpene glycosides (1-6), beesiosides A-F, were isolated from whole plants of Beesia calthaefolia, and their structures were elucidated on the basis of extensive NMR experiments and chemical methods. Beesiosides A-F were assigned as (20S,24R)-epoxy-9,19-cyclolanostane-3beta,16beta,18,25-tetraol-3-O-beta-D-xylopyranoside (1), (20S,24R)-epoxy-9,19-cyclolanostane-3beta,12beta,16beta,18,25-pentaol-3-O-beta-D-xylopyranoside (2), (20S,24R)-epoxy-9,19-cyclolanostane-3beta,12alpha,16beta,18,25-pentaol-3-O-beta-D-xylopyranoside (3), (20S,24R)-16beta-acetoxy-20,24-epoxy-9,19-cyclolanostane-3beta,12alpha,18,25-tetraol-3-O-beta-D-xylopyranoside (4), (20S,24R)-epoxy-9,19-cyclolanostane-3beta,15alpha,16beta,18,25-pentaol-3-O-beta-D-xylopyranoside (5), and (20S,24R)-16beta-acetoxy-20,24-epoxy-9,19-cyclolanostane-3beta,12beta,25-triol-3-O-beta-D-xylopyranoside (6), respectively.