Withanolides from Vassobia lorentzii

Eight new withanolides were isolated from the aerial parts of Vassobia lorentzii and characterized by spectroscopic methods and with the aid of molecular modeling. The compounds were identified as (17S,20R,22R)-5beta,6beta:18,20-diepoxy-18-hydro xy-1-oxowitha-2,5, 24-trienolide (1); (17S,20R,22R)-18,20-epoxy-4beta, 18-dihydroxy-1-oxowitha-2,5,24-trienolide (2); (17S,18R,20R, 22R)-4beta-hydroxy-18,20-epoxy-18-methoxy-1-oxowitha-2,5, 24-trienolide (3); (17S,18S,20R,22R)-4beta-hydroxy-18, 20-epoxy-18-methoxy-1-oxowitha-2,5,24-trienolide (4); (17S,20R, 22R)-4beta-hydroxy-18,20-epoxy-1,18-dioxowitha-2,5,24-tri enolide (5); (17S,18R,20R,22R)-18,20-epoxy-18-methoxy-1,4-dioxowitha++ +-2,5, 24-trienolide (6); (17S,18S,20R,22R)-18,20-epoxy-18-methoxy-1, 4-dioxowitha-2,5,24-trienolide (7); and (17S,20R,22R)-5beta, 6beta-epoxy-4beta,18,20-trihydroxy-1-oxowitha-2,24-die nolide (8). Compounds 1 and 2 were obtained as epimeric mixtures at C-18.     

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.     

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.     

A new withanolide glycoside from physalis peruviana

A new withanolide glycoside, 17beta-hydroxy-14, 20-epoxy-1-oxo-[22R]-3beta-[O-beta-D-glucopyranosyl]-witha-5, 24-dienolide (1), has been isolated from the whole plant of Physalis peruviana. Its identity was determined using a combination of spectroscopic data including 2D NMR techniques and chemical transformations.     

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。     

Trypanocidal withanolides and withanolide glycosides from Dunalia brachyacantha.

Two new withanolide glycosides, (20R,22R)-O-(3)-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl-1 alpha,12 beta-diacetoxy-20-hydroxywitha-5,24-dienolide (3) and (20R,22R)-O-(3)-beta-D-xylopyranosyl(1-->3)-[beta-D-xylopyranosyl(1-->4)]-beta-D-glucopyranosyl-1 alpha-acetoxy-12 beta,20-dihydroxywitha-5,24-dienolide (4), were isolated from the leaves and root of Dunalia brachyacantha. Their aglycones, (20R,22R)-1 alpha,12 beta-diacetoxy-3 beta,20-dihydroxywitha-5,24-dienolide (or 1 alpha,12 beta-diacetyldunawithagenine) and (20R,22R)-1 alpha-acetoxy-3 beta,12 beta,20-trihydroxywitha-5,24-dienolide (or 1 alpha-acetyl-12 beta-hydroxydunawithagenine), are novel. The known 18-acetoxywithanolide D (1) and 18-acetoxy-5,6-deoxy-5-withenolide D (2) were also isolated from the leaves. These last two compounds were shown to be responsible for the trypanocidal, leishmanicidal, and bactericidal activities manifested by the crude ethanolic extract. The structures were deduced from spectroscopic data and on the basis of chemical evidence.     

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).     

New bioactive clerodane diterpenoids from the bark of Casearia grewiifolia

Bioactivity-guided fractionation of hexane and dichloromethane extracts of the bark of Casearia grewiifolia afforded four new clerodane diterpenes, caseargrewiins A-D (1-4), and two known clerodane diterpenes, rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-6-methoxy-2-(2-methylbutanoyloxy)cleroda-3,13(16),14-triene (5) and rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-6-hydroxy-2-(2-methylbutanoyloxy)cleroda-3,13(16),14-triene (6). The structures of 1-4 were established on the basis of the interpretation of their 1D and 2D NMR spectral data. The absolute configuration of 4 was determined by the modified Mosher's method. All compounds exhibited promising antimalarial and antimycobacterial activities but also cytotoxicity against three cancer cell lines.     

Structure and stereochemistry of new cytotoxic clerodane diterpenoids from the bark of Casearia lucida from the Madagascar rainforest

Bioassay-guided fractionation of a CH(2)Cl(2)/MeOH extract of the bark of Casearia lucida resulted in the isolation of 11 new clerodane diterpenes, namely, casearlucins A-K (1-11), and three known clerodane diterpenoids, rel-(2S,5R,6R,8S,9S,10R,18S,19R)-diacetoxy-18,19-epoxy-6-hydroxy-2-(2xi-methylbutanoyloxy)cleroda-3,13(16),14-triene (12), rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-6-methoxy-2-(2xi-methylbutanoyloxy)cleroda-3,13(16),14-triene (13), and rel-(2S,5R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-2-(2xi-methylbutanoyloxy)cleroda-3,13(16),14-triene (14). The structures of compounds 1-11 were established on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. All compounds exhibited cytotoxicity activity against the A2780 ovarian cancer cell line, but none of the six compounds selected for testing in multiple cell lines showed significant selectivity.     

Jatrophane diterpenoids from Euphorbia mongolica as modulators of the multidrug resistance of L5128 mouse lymphoma cells

The dried aerial parts of Euphorbia mongolica afforded three new acylated polyhydroxy diterpenoids based on the jatrophane framework. The structures were established by means of a combination of 1D and 2D NMR techniques and mass spectrometry as (2S,3S,4R,5R,7S,8R,13S,15R)-5alpha,7beta,8alpha-triacetoxy-3beta-benzoyloxy-15beta-hydroxyjatropha-6(17),11E-diene-9,14-dione (1), (2S,3S,4R,5R,7S,8S,9S13S,15R)-5alpha,7beta,8alpha,9alpha,15beta-pentaacetoxy-3beta-benzoyloxyjatropha-6(17),11E-dien-14-one (2), and (2S,3S,4R,5R,7S,8S,9S13S,15R)-3beta,7beta,8alpha,9alpha,15beta-pentaacetoxy-5alpha-benzoyloxyjatropha-6(17),11E-dien-14-one (3). When the isolates were assayed for multidrug resistance-reversing activity in a rhodamine 123 exclusion test using L5178 mouse lymphoma cells, all compounds demonstrated a concentration-dependent effect in inhibiting the efflux pump activity of these tumor cells in the range 11.2-112 microM.     

Cytotoxic clerodane diterpenoids from Casearia membranacea

Bioassay-guided fractionation of the EtOAc extract of Casearia membranacea leaves and twigs afforded three new clerodane diterpenes, caseamembrins M-O (1-3), and the known rel-(2S,5R,6R,8S,9S,10R,18S,19R)-2-(2-methylbutyryloxy)-6-hydroxy-18,19-di-O-acetyl-18,19-epoxycleroda-3,13(16),14-triene (4) and caseamembrin D (5). The structures of 1-3, including the relative configurations, were established by extensive NMR spectroscopic analyses. The cytotoxic activities of the isolated diterpenoids against human oral epidermoid (KB), medulla (Med), and colon (DLD-1) cancer cell lines were evaluated.     

New steroidal alkaloids from Sarcococca saligna

Five new pregnane-type steroidal alkaloids (1-5) have been isolated from Sarcococca saligna. A combination of UV, IR, MS, and 1D and 2D NMR spectroscopic studies established their structures as salignarine A [(20S)-2beta-hydroxy-4beta-acetoxy-5alpha, 6alpha-epoxy-20-(dimethylamino)-3beta-(tigloylamino)pregnane ] (1), salignarine B [(20S)-2beta-hydroxy-20-(dimethylamino)-3beta-(tigloylamino) -pregn-5- ene] (2), salignarine C [(20S)-2beta-hydroxy-20-(dimethylamino)-3beta-(senecioylamino++ +)-pregn- 5-ene] (3), salignarine D [(20S)-20-(dimethylamino)-3beta-(senecioylamino)-5alpha-preg n-16-ene] (4), and salignarine E [(20S)-20-(dimethylamino)-3beta-(tigloylamino)-pregn-4-ene] (5), respectively.     

Eremophilane sesquiterpenes from Ligularia macrophylla

New eremophilane sesquiterpenes, 6beta-sarracinoyloxy-1beta,10beta-epoxy-furanoeremophilane (1), 6alpha-angeloyloxy-10betaH-furanoeremophil-1-one (2), 1alpha-hydroxy-9-deoxycacalol (3), and 1beta-hydroxy-11(R,S)-8-oxoeremophil-6,9-dien-12-al (4a+4b), together with five known sesquiterpenes (5-9) were isolated from the roots and rhizomes of Ligularia macrophylla. The structures were elucidated by spectroscopic methods including 2D NMR techniques, and the structure of 1 was confirmed by a single-crystal X-ray diffraction experiment. The compounds were also evaluated for cytotoxic activity against human lung carcinoma (A-549) and human breast adenocarcinoma (MCF-7) and were found to show only very weak cytotoxicity.     

Beesiosides G, H, and J-N, seven new cycloartane triterpene glycosides from Beesia calthifolia

Seven new cycloartane glycosides (1-7), beesiosides G, H, and J-N, together with beesioside I (8) and beesioside A, were isolated from the rhizomes of Beesia calthifolia, and their structures were established by spectroscopic and chemical methods. Beesiosides G, H, and J-N were assigned as 20xi(1),24xi(2)-epoxy-9,19-cyclolanostane-3beta,16beta,18,25-tetraol-3-O-beta-D-glucopyranoside (1), 20xi(1),24xi(2)-epoxy-9,19-cyclolanostane-3beta,16beta,18,25-tetraol-3-O-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (2), (20S,24R)-15alpha,16beta-diacetoxy-20,24-epoxy-9,19-cyclolanostane-3beta,18,25-triol-3-O-beta-D-xylopyranoside (3), (20S,24S)-16beta-acetoxy-18,24;20,24-diepoxy-9,19-cyclanostane-3beta,15beta,25-triol-3-O-beta-D-xylopyranoside (4), (20S,24S)-16beta-acetoxy-18,24;20,24-diepoxy-9,19-cyclanostane-3beta,25-diol-3-O-beta-D-xylopyranoside (5), 20xi(1),24xi(2)-epoxy-15alpha-acetoxy-9,19-cyclolanostane-3beta,16beta,25-triol-3-O-beta-D-xylopyranoside (6), and 20xi(1),24xi(2)-epoxy-9,19-cyclolanostane-3beta,12alpha,15alpha,16beta,25-pentaol-3-O-beta-D-xylopyranoside (7), respectively.     

New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa

A phytochemical investigation on the stems of Annona squamosa led to the isolation of six new ent-kaurane diterpenoids, annomosin A (16beta-hydroxy-19-al-ent-kauran-17-yl 16beta-hydro-19-al-ent-kauran-17-oate) (1), annosquamosin C (16alpha-hydro-17-hydroxy-19-nor-ent-kauran-4alpha-ol) (2), annosquamosin D (16beta-acetoxy-17-hydroxy-19-nor-ent-kauran-4alpha-ol) (3), annosquamosin E (16beta-hydroxy-17-acetoxy-19-nor-ent-kauran-4alpha-formate) (4), annosquamosin F (16beta-hydroxy-17-acetoxy-18-nor-ent-kauran-4beta-hydroperoxide) (5), and annosquamosin G (16beta,17-dihydroxy-18-nor-ent-kauran-4beta-hydroperoxide) (6), along with 14 known ent-kaurane diterpenoids. The structures of 1-6 were elucidated by spectroscopic data interpretation. Compound 1 is the first dimeric ent-kaurane derivative to have been reported from a plant in the family Annonaceae. Certain useful NMR data were generalized to determine the stereochemistry of C-16 among the ent-kaurane diterpenoids investigated. ent-Kaur-16-en-19-oic acid (9) and 16alpha-hydro-19-al-ent-kauran-17-oic acid (17) showed complete inhibitory effects on rabbit platelet aggregation at 200 microM.     

Steroids from the roots of Nerium oleander.

Two new cardenolides, 3beta-hydroxy-5alpha-carda-14(15), 20(22)-dienolide (beta-anhydroepidigitoxigenin) (1) and 3beta-O-(D-digitalosyl)-21-hydroxy-5beta-carda-8,14,16 , 20(22)-tetraenolide (neriumogenin-A-3beta-D-digitaloside) (2), and two known compounds, proceragenin and neridienone A (3), have been isolated from the roots of Nerium oleander. The structures of 1 and 2 were elucidated on the basis of spectral data interpretation.     

Neoclerodane diterpenoids from Scutellaria caerulea.

Five new neoclerodane diterpenoids have been isolated from Scutellaria caerulea: (11S*)-6 alpha-acetoxy-7 beta,11-diisobutiryloxy-1 beta,8 beta-dihydroxy-4(18),13-neoclerodadien-15,16-olide (scuterulein A) (1); (13R*)-1 beta-6 alpha-7 beta-triacetoxy-11 beta-benzoyloxy-8 beta,13-epoxy-4(18)-neocleroden-15,16-olide (scuterulein B) (2); (11S*)-1 beta,6 alpha,11-triacetoxy-7 beta-isobutiryloxy-8 beta-hydroxy-4(18),13-neoclerodadien-15,16-olide (scuterulein C) (3); (11S*)-6 alpha,11-diacetoxy-7 beta-isobutiryloxy-1 beta,8 beta-dihydroxy-4(18),13-neoclerodadien-15,16-olide (deacetyl scuterulein C) (4), and (11E)-6 alpha-acetoxy-7 beta-isobutiryloxy-1 beta,8 beta-dihydroxy-4(18),11,13-neoclerodatrien-15,16-olide (scuterulein D) (5). Structures were established by spectroscopic and chemical methods. An X-ray analysis was carried out on scuterulein B (2).     

苍耳子中苯丙素类化学成分的研究

目的 研究菊科植物苍耳(Xanthium sibiricum Patrin ex Widder)的干燥成熟带总苞的果实(苍耳子)中苯丙素类化学成分。方法 采用正相硅胶柱色谱、反相十八烷基硅烷键合硅胶(ODS)柱色谱、Sephadex LH-20凝胶柱色谱和半制备高效液相色谱(HPLC)等色谱方法进行分离纯化,并结合高分辨质谱(HR-ESI-MS)、核磁共振(NMR)对分离得到的化合物进行结构鉴定。采用脂多糖(LPS)诱导的巨噬细胞RAW 264.7为筛选模型评价分离得到化合物的抗炎活性。结果 从苍耳子体积分数95%乙醇提取物的乙酸乙酯萃取物中分离并鉴定了24个苯丙素类化合物,分别为c-藜芦酰乙二醇(1)、3,4'-二羟基-3'-甲氧基苯丙酮(2)、阿魏醛(3)、丁香脂素(4)、蛇菰宁(5)、落叶松脂醇(6)、愈创木基甘油(7)、3-hydroxy-l-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone(8)、salicifoliol(9)、6-(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-2-ol(10)、榕醛(11)、jatrointelignan D(12)、icariol A₂(13)、异落叶松脂素(14)、ehletianol C(15)、(7R,7'R,7”S,7‴S,8S,8'S,8”S,8‴S)-4”,4‴-dihydroxy-3,3',3”,3‴,5,5'-hexamethoxy-7,9';7',9-diepoxy-4,8”;4',8‴-bisoxy-8,8'-dineolignan-7”,7‴,9”,9‴-tetraol(16)、(7R,7'R,7”R,7‴S,8S,8'S,8”S,8‴S)-4”,4‴-dihydroxy-3,3',3”,3‴,5,5'-hexamethoxy-7,9';7',9-diepoxy-4,8”;4',8‴-bisoxy-8,8'-dineolignan-7”,7‴,9”,9‴-tetraol(17)、2-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-propan-1,3-diol(18)、2,3-bis-(4-hydroxy-3-methoxyphenyl)-3-methoxypropanol(19)、楝叶吴萸素B(20)、threo-guaiacylglycerol-8-vanillin ether(21)、erythro-guaiacylglycerol-8-vanillin ether(22)、黄花菜木脂素B(23)和27-对香豆酰氧基熊果酸(24)。结论 化合物6~24为首次从苍耳中分离得到。对分离得到的24个化合物进行抗炎活性筛选,其中,化合物14、21和23具有抗炎活性,其IC₅₀值分别为(28.14±1.89),(16.78±0.68)和(38.42±2.15)μmol·L^-1。     

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.     

Phrygiasterol, a cytotoxic cyclopropane-containing polyhydroxysteroid, and related compounds from the pacific starfish Hippasteria phrygiana

The new cyclopropane-containing steroid phrygiasterol (1) and steroid glycoside phrygioside B (2), along with previously known borealoside C (2a) and (20R,24S)-5alpha-cholesta-3beta,6alpha,8,15alpha,24-pentaol (3), have been isolated from the Pacific starfish Hippasteria phrygiana. On the basis of spectroscopic analyses, using 1D and 2D NMR techniques and some chemical transformations, the structures of 1 and 2 have been established as (20R,24R,25R)-24,26-cyclo-5alpha-cholesta-3beta,6alpha,8,15alpha,16beta,27-hexaol (1) and the sodium salt of (20R,24S)-24-O-(3-O-methyl-4-O-sulfate-beta-d-xylopyranosyl)-5alpha-cholesta-3beta,6alpha,8,15alpha,24-pentaol (2), respectively. Compound 1 inhibited the growth of Ehrlich carcinoma cells with an IC(50) of 50 microg/mL, whereas 2 induced apoptosis of the same cells (EC(50)=70 microg/mL) and inhibited Ca(2+) influx into mouse spleenocytes (EC(50)=20microg/mL).