Nitrogen-containing phorbol esters from Croton ciliatoglandulifer and their effects on cyclooxygenases-1 and -2

Four new phorbol derivatives, 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (1), 12-O-[(2S)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (2), 12-O-[3-methyl-2-butenoyl]-4-deoxyphorbol 13-acetate (3), and 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]phorbol 13-acetate (4), along with six known compounds, were isolated from the aerial parts of Croton ciliatoglandulifer. An anti-inflammatory activity of a hexane extract of this plant was demonstrated against ear edema in mice produced by 12-O-tetradecanoylphorbol 13-acetate, and compounds 1, 4, and 3beta-O-acetyloleanolic acid (5) were active when evaluated against cyclooxygenases-1 and -2.     

Sulfated pregnane glycosides from Periploca graeca

Six new pregnane glycosides, four of them sulfated derivatives, were isolated from small branches of Periploca graeca. The compounds were identified as 16alpha-[(6-O-sulfo-beta-D-glucopyranosyl)oxy]pregn-5-en-20-ol-3beta-yl O-(2-O-acetyl-beta-D-digitalopyranosyl)-(1-->4)-beta-D-cymaropyranoside (1), 16alpha-[(6-O-sulfo-beta-D-glucopyranosyl)oxy]pregn-5-en-20-ol-3beta-yl O-beta-D-oleandropyranosyl-(1-->4)-beta-D-oleandropyranoside (2), 16alpha-[(6-O-sulfo-beta-D-glucopyranosyl)oxy]pregn-5-en-20-ol-3beta-yl O-beta-D-oleandropyranoside (3), 16alpha-[(6-O-sulfo-beta-D-glucopyranosyl)oxy]pregn-5-ene-3beta,20-diol (4), 20-O-[(beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->2)-beta-D-digitalopyranosyl)oxy]pregn-5-en-16beta-ol-3beta-yl O-beta-D-digitalopyranosyl-(1-->4)-beta-d-cymaropyranoside (5), and calogenin 3-O-beta-D-digitalopyranoside-20-O-beta-D-canaropyranoside (6). Three pregnane glycosides, previously reported from the genus Periploca, were also isolated. Structures were established on the basis of spectroscopic analyses, including 1D and 2D NMR experiments, HRESIMS, elemental analysis, and chemical degradation.     

花椒果皮化学成分分离鉴定

目的:研究花椒Zanthoxylum bungeanum果皮的化学成分。方法:将花椒干燥果皮粉碎后用95%乙醇冷浸提取浓缩得到总浸膏,将总浸膏吸附于硅藻土上,依次用不同极性溶剂进行洗脱,浓缩得到相应洗脱部位。对二氯甲烷部位和正丁醇部位分别采用硅胶柱色谱,LH-20型羟丙基葡聚糖凝胶(Sephadex LH-20)凝胶柱色谱,ODS柱色谱,半制备HPLC等方法进行分离纯化,并结合理化性质和多种波谱学方法鉴定其结构。结果:从花椒果皮二氯甲烷部位和正丁醇部位分离得到14个化合物,分别鉴定为(1S,3S)-1-甲基-1,2,3,4-四氢-β-咔啉-3-羧酸(1),(3S)-1,2,3,4-四氢-β-咔啉-3-羧酸(2),芹菜素-7,4’-二甲醚(3),芫花素(4),淫羊藿次苷F2(5),breyniaionoside A(6),3-甲氧基苯乙醇-4-O-β-D-葡萄糖苷(7),3-甲氧基-5-羟基苯-1-O-β-D-葡萄糖苷(8),苔黑酚葡萄糖苷(9),紫丁香苷(10),4-[(3S)-3-羟基丁基]-2-甲氧基苯-β-D-吡喃葡萄糖苷(11),(+)-南烛木树脂酚-3a-O-β-D-葡萄糖苷(12),2-甲基丙基-6-O-β-D-呋喃芹糖基-β-D-吡喃葡萄糖苷(13)和(E)-6-羟基-2,6-二甲基辛-2,7-二烯酸(14)。结论:以上所有化合物均为首次从花椒植物中分离得到,其中化合物1~4,12,14为首次从花椒属植物中分离得到。     

Kinmoonosides A-C, three new cytotoxic saponins from the fruits of Acacia concinna, a medicinal plant collected in myanmar

Three genuine saponins, named kinmoonosides A-C (1-3), have been isolated, together with a new monoterpenoid (4), from a methanolic extract of the fruits of Acacia concinna. The structures of kinmoonosides A-C were elucidated on the basis of spectral analysis as 3-O-?alpha-L-arabinopyranosyl(1-->6)-[beta-D-glucopyranosyl(1-->2) ]-b eta-D-glucopyranosyl?-21-O-?(6R, 2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2'E)-6'-hydroxyl-2'-hydroxymet hyl-6'-methyl-2',7'-octadienoyl-beta-D-quinovopyranosyl]-2, 7-octadienoyl?acacic acid 28-O-alpha-L-arabinofuranosyl(1-->4)-[beta-D-glucopyranosyl(1-->3)]-a lpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl ester (1); 3-O-?alpha-L-arabinopyranosyl(1-->6)-[beta-D-glucopyranosyl(1-->2) ]-b eta-D-glucopyranosyl?-21-O-?(6S, 2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2'E)-6'-hydroxyl-2'-hydroxymet hyl-6'-methyl-2',7'-octadienoyl-beta-D-quinobopyranosyl]-2, 7-octadienoyl?acacic acid 28-O-alpha-L-arabinofuranosyl(1-->4)-[beta-D-glucopyranosyl(1-->3)]-a lpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl ester (2); and 3-O-?alpha-L-arabinopyranosyl(1-->6)-[beta-D-glucopyranosyl(1-->2) ]-b eta-D-glucopyranosyl?-21-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl- 2,7-octadienoyl]acacic acid 28-O-alpha-L-arabinofuranosyl(1-->4)-[beta-D-glucopyranosyl(1-->3)]-a lpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl ester (3), respectively. The new monoterpenoid 4 was determined as 4-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2, 7-octadienoyl]-D-quinovopyranose. Compounds 1-3 showed significant cytotoxicity against human HT-1080 fibrosarcoma cells.     

Acylated flavonoids from pseudognaphalium species

Two new acylated flavonoids have been isolated from the resinous exudates of Pseudognaphalium robustum and Pseudognaphalium cheirantifolium. Their structures were elucidated by high-resolution spectroscopic methods as 5,7,8-trihydroxy-3-methoxyflavone 8-O-[(E)-2-methyl-2-butenoate] (1) and 5,7,8-trihydroxy-3, 6-dimethoxyflavone 8-O-[(E)-2-methyl-2-butenoate] (2).     

花朱顶红中非生物碱类成分研究

目的研究石蒜科植物花朱顶红中非生物碱类成分。方法采用大孔树脂、硅胶、ODS柱色谱分离纯化,经理化常数、光谱学方法鉴定结构。结果分离得到了5个葡糖鞘脂类成分,其结构分别鉴定为(2S,3R,4E,8Z)-2-[(2R-2-羟基十六酰)氨基]-4,8-十八二烯-1,3-二醇1-O-β-D-吡喃葡萄糖苷()、(2S,3R,4E,8E)-2-[(2R-2-羟基十六酰)氨基]-4,8-十八二烯-1,3-二醇1-O-β-D-吡喃葡萄糖苷()、(2S,3R,4E,8Z)-2-[(2R-2-羟基十八酰)氨基]-4,8-十八二烯-1,3-二醇1-O-β-D-吡喃葡萄糖苷()、(2S,3R,4E,8E)-2-[(2R-2-羟基十八酰)氨基]-4,8-十八二烯-1,3-二醇1-O-β-D-吡喃葡萄糖苷()、(2S,3R,4E,8Z)-2-[(2R-2-羟基二十酰)氨基]-4,8-十八二烯-1,3-二醇1-O-β-D-吡喃葡萄糖苷()。结论它们均为首次从花朱顶红中分得。     

无梗五加果实中齐墩果酸苷的分离与鉴定

目的:研究无梗五加Acanthopanax sessiliflorus( Ruqr.et Maxim) Seem.果实的化学成分.方法:采用溶剂提取法、溶剂萃取法、硅胶柱色谱法、凝胶柱色谱法、重结晶法对无梗五加果实中的化合物进行分离纯化;根据光谱数据和理化性质确定化合物结构.结果:分离并鉴定了6个化合物,分别为齐墩果酸-3-O-β-D-葡萄醛酸甲酯苷(1),齐墩果酸-3 -O-α-L-阿拉伯糖苷(2),齐墩果酸-3-O-β-D-葡萄醛酸正丁酯苷(3),齐墩果酸-3-O-β-D-葡萄糖醛酸苷(4),齐墩果酸(5),3-0-[(α-L-arabinopyranosyl) -( 1→2)] -[ -β-D-glucuronopyranosyl-6-O-methyl ester] -olean-12-ene-28-olic acid(6).结论:化合物2,3为首次从无梗五加果实中分离得到.     

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.     

New triterpenoid saponins from Maesa japonica

New triterpenoid saponins, maejaposides A, B, C, D, and E, were isolated from the roots of Maesa japonica and were, respectively, defined to be 3-O-[beta-D-xylopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->2)-bet a-D-galactopyranosyl-(1-->3)] [beta-D-galactopyranosyl-(1-->2)]beta-D-glucuronopyranosides of 22alpha-[(Z)-2-hexenoyloxy]-13beta,28-oxido-olean++ +-16alpha, 28alpha-diol (1); 22alpha-[2'-methylbutanoyl]-13beta, 28-oxido-olean-16alpha,28alpha-diol (2a) and 22alpha-angeloyloxy-13beta,28-oxido-olean-16a lpha,28alpha-diol (2b); 21beta,22alpha-diangeloyloxy-13beta,28-oxido- olean-16alpha, 28alpha-diol (3); 21beta-angeloyloxy, 22alpha-(2'-methylbutanoyl)-13beta,28-oxido-olean++ +-16alpha, 28alpha-diol (4), and 21beta-angeloyloxy, 22alpha-[(Z)-2'-hexenoyl]-13beta,28-oxido-olean- 16alpha,28alpha-diol (5). Their structures were established on the basis of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC, and NOESY) and ESIMS/MS studies, along with chemical degradation.     

土贝母中一个新的三萜皂苷

目的对土贝母Bolbostemma paniculatum的三萜皂苷成分进行分离和结构鉴定。方法采用反复柱色谱方法进行分离,通过理化性质和波谱分析鉴定结构。结果从土贝母中分离并鉴定了1个新的三萜皂苷脱木糖土贝母苷丙(dexylosyltubeimoside Ⅲ)。结论化合物为新化合物。     

Acetals of three new cycloartane-type saponins from Egyptian collections of Astragalus tomentosus

Three new cycloartane-type saponin ethyl acetals, deacetyltomentoside I (2), tomentoside III (3), and tomentoside IV (4), were isolated along with the known acetal tomentoside I (1) from the aerial parts of Astragalus tomentosus of Egyptian origin. The saponins from which the acetals are most probably derived are also new compounds. The structures of the acetals were established as 6alpha-hydroxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-beta-d-xyloside (2), 6alpha-acetoxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-[beta-d-(4'-trans-2-butenoyl)]xyloside (3), and 6alpha-acetoxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-[beta-d-glucopyranosyl(1 --> 2)]-beta-d-xyloside (4), by detailed spectroscopic and chemical studies.     

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.     

Phytochemical investigation of Turnera diffusa

A phytochemical investigation of Turnera diffusa afforded 35 compounds, comprised of flavonoids, terpenoids, saccharides, phenolics, and cyanogenic derivatives, including five new compounds (1-5) and a new natural product (6). These compounds were characterized as luteolin 8-C-E-propenoic acid (1), luteolin 8-C-beta-[6-deoxy-2-O-(alpha-l-rhamnopyranosyl)-xylo-hexopyranos-3-uloside] (2), apigenin 7-O-(6' '-O-p-Z-coumaroyl-beta-d-glucopyranoside) (3), apigenin 7-O-(4' '-O-p-Z-coumaroylglucoside) (4), syringetin 3-O-[beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside] (5), and laricitin 3-O-[beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside] (6). Their structures were determined by spectroscopic and chemical methods.     

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).     

短管兔耳草化学成分的研究(Ⅱ)

目的研究短管兔耳草Lagotis brevituba Maxim.的化学成分。方法短管兔耳草70%乙醇提取物采用硅胶、Sephadex LH-20、MCI、HPLC制备柱进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到11个化合物,分别鉴定为baldaccioside(1)、globularin(2)、10-O-[3,4-二甲氧基-(Z)-肉桂酰基]-梓醇(3)、10-O-[3,4-二甲氧基-(E)-肉桂酰基]-梓醇(4)、globularidin(5)、10-O-对甲氧基-(E)-肉桂酰基-梓醇(6)、兔耳草苷B(7)、6-O-(E)-肉桂酰基-α/β-D-吡喃葡萄糖苷(8)、松脂酚-4-O-β-D-吡喃葡萄糖苷(9)、syringaresinol-4′-O-β-D-monoglucoside(10)、6-O-[3,4-二甲氧基-(Z)-肉桂酰基]-α/β-D-吡喃葡萄糖苷(11)。结论化合物2~4、6~7、10为首次从该植物中分离得到,化合物1、5、8~9、11首次从兔耳草属植物中分离得到。     

桫椤化学成分研究

目的:研究桫椤Cyathea spinulosa Wall.的化学成分。方法:采用各种柱色谱进行分离纯化,根据理化性质和光谱数据进行结构鉴定。结果:从桫椤的乙醇提取物中共分离鉴定了8个化合物,分别为:豆甾-4-烯-3,6-二酮(1)、豆甾-3,6-二酮(2)、麦角甾醇(3)、原儿茶醛(4)、1-O-β-D-glucopyranosyl-(2S,3R,4E,8Z)-2-[(2-hydroxyoctade-canoyl)amido]-4,8-octadecadiene-1,3-diol(5)、(2S,3S,4R)-2-[(2'R)-2'-hydroxytetracosanoylamino]-1,3,4-octade-canetriol(6)、β-谷甾醇(7)、胡萝卜苷(8)。结论:其中,化合物1～6为首次从该植物中分离得到。     

Separation of Five Quinolone Alkaloids from Fruits of Evodia rutaecarpa by High-speed Counter-current Chromatography

Objective To develop a suitable method for the large-scale separation of quinolone alkaloids from the fruits of Evodia rutaecarpa by high-speed counter-current chromatography(HSCCC).Methods Two solvent systems were developed for the separation method.The upper phase was used as the stationary phase,and the lower phase was used as the mobile phase at 35 oC with the flow rate of 2 mL/min and rotation speed of 855 r/min.Results Using the described method,1-methyl-2-undecyl-4(1H)-quinolone(1),evocarpine(2),1-methy-2-[(6Z,9Z)]-6,9-pentade-cadienyl-4-(1H)-quinolone(3),dihydroevocarpine(4),and the mixture(5)of 1-methyl-2-[(Z)-10-pentadecenyl]-4(1H)-quinolone(Va)and 1-methyl-2-[(Z)-6-pentadecenyl]-4(1H)-quinolone(Vb)could be isolated from a petroleum ether extract.They were identified by 1H-NMR,13 C-NMR,and MS/MS,and the purities were 94.3%,95.2%,96.8%,98.3%,and 96.8%,respectively.Conclusion Five quinolone alkaloids from the fruits of E.rutaecarpa could be systematically isolated and purified using HSCCC.The presented method is simple and efficient with good potentials on the preparation of reference substances,especially on the quality control of Chinese materia medica.     

A ceramide and cerebroside from the starfish asterias amurensis Lütken and their plant-growth promotion activities

The new phytosphingosine-type ceramide asteriaceramide A (1) and glucocerebroside asteriacerebroside G (2), together with two known cerebrosides, asteriacerebrosides A and B, were isolated from lipophilic fractions of the whole bodies of the Northern Pacific starfish Asterias amurensis Lütken. The water-soluble fraction afforded two known asterosaponins, glycoside B(2) and asterosaponin-1. The structures of 1 and 2 were determined on the basis of chemical and spectroscopic evidence as (2S,3S,4R,13Z)-2-[(2'R)-2-hydroxyhexadecanoylamino]-13-docosene-1,3,4-triol (1) and 1-O-(beta-d-glucopyranosyl)-(2S,3R,4E,13Z)-2-[(2'R)-2-hydroxytetradecanoylamino]-4,13-docosadiene-1,3-diol (2). Compounds 1, 2, and asteriacerebrosides A and B promoted plant growth in sprouts of Brassica campestris.     

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(19)、6-羟基-香豆素-7-O-α-L-鼠李糖基-(1→6)-O-β-D-葡萄糖苷(20)、(7S,8R)-二氢去氢二松柏醇-4-O-β-D-吡喃葡萄糖苷(21)。结论化合物1为新化合物,命名为紫丁葡芹苷,2为新天然产物,5~11和18为首次从堇菜属中分离得到,12和21为首次从紫花地丁中分离得到。     

Two major saponins from seeds of Barringtonia asiatica: putative antifeedants toward Epilachna sp. larvae

Two major saponins have been isolated from a methanol extract of the seeds of Barringtonia asiatica, and their structures elucidated (mainly by two-dimensional NMR spectroscopy) as 3-O-[[beta-D-galactopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->2)]-beta-D-glucuronopyranosyloxy]-22-O-(2-methylbutyroyloxy)-15,16,28-trihydroxy-(3beta,15alpha,16alpha,22alpha)-olean-12-ene (3) and 3-O-[[beta-D-galactopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->2)]-beta-D-glucuronopyranosyloxy]-22-O-[2(E)-methyl-2-butenyloyloxy]-15,16,28-trihydroxy-(3beta,15alpha,16alpha,22alpha)-olean-12-ene (4). The antifeedant properties of 3 and 4 toward Epilachna larvae are discussed.