Lignans from the flower buds of Magnolia liliflora Desr

Six new lignans, 1- 6, along with six known compounds were obtained from the flower buds of Magnolia liliflora Desr. The new lignans were elucidated as (1 S*,2 R*,5 S*,6 S*)-2-(3,5-dimethoxyphenyl)-6-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (1), (1 R*,2 R*,5 R*,6 S*)-2-(3,5-dimethoxyphenyl)-6-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (2), (1 R*,?2 R*,5 R*,6 S*)-2,6-bis (3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (3), (1 R*,2 S*,5 R*,6 R*)-2-(3,4-methylenedioxyphenyl)-6-(3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane ( 4), (7' S*,8 R*,8' R*)-3,5'-dimethoxy-3',4,9'-trihydroxy-7',9-epoxy-8,8'-lignan (5), and (7' R*,8' S*)-3,3',4,5'-tetramethoxy-7-en-7',9-epoxy-8,8'-lignan (6), by the analysis of 1D and 2D-NMR as well as HRESIMS data. The capacity of compound 1 to protect against damages to the DNA of rat lymphocyte cells induced by UV irradiation was assessed by the comet assay. It showed stronger antigenotoxicity than ascorbic acid from 6×10(-3)?mmol·L(-1) to 6×10(-6)?mmol·L(-1).     

紫花前胡化学成分的研究

目的研究中药紫花前胡［Peucedanum decursivum(Miq.)Maxim］根的化学成分。方法用硅胶柱色谱和制备型高效液相色谱进行分离纯化,用光谱分析和化学方法鉴定其结构。结果从紫花前胡根中分得7个线型吡喃香豆素类化合物,其结构分别鉴定为3′(S)-hydroxy-4′(R)-angeloyloxy-3′,4′-dihydroxanthyletin(1);3′(S)-acetoxy-4′(R)-hydroxy-3′,4′-dihydroxanthyletin(2);3′(S)-acetoxy-4′(R)-angeloyloxy-3′,4′-dihydroxanthyletin(3);Pd-C-IV(4);Pd-C-II(5);(+)-3′S-Decursinol(6);(+)-trans-Decursidinol(7)。结论化合物1和2为新化合物,分别命名为紫花前胡素D和紫花前胡素F;6和7为首次从该植物中分得。     

穿心莲根的化学成分研究

为研究常用中药爵床科植物穿心莲(Andrographis paniculata)根的化学成分,运用各种色谱方法从安徽临泉产穿心莲根的80%乙醇提取物中分离并鉴定了28个化合物,其中20个黄酮:5,5'-二羟基-7,8,2'-三甲氧基黄酮(1)、5-羟基-7,8,2',6'-四甲氧基黄酮(2)、5,3'-dihydroxy-7,8,4',-trimethoxyflavone(3)、2'-羟基-5,7,8-三甲氧基黄酮(4)、5-羟基-7,8,2',3',4'-五甲氧基黄酮(6)、wightin(7)、5,2',6'-trihydroxy-7-methoxyflavone 2'-O-β-D-glucopyranoside(8)、5,7,8,2'-四甲氧基黄酮(10)、5-羟基-7,8-二甲氧基二氢黄酮(11)、5-羟基-7,8-二甲氧基黄酮(12)、5,2'-二羟基-7,8-二甲氧基黄酮(13)、5-羟基-7,8,2',5'-四甲氧基黄酮(14)、5-羟基-7,8,2',3'-四甲氧基黄酮(15)、5-羟基-7,8,2'-三甲氧基黄酮(16)、5,4'-二羟基-7,8,2',3'-四甲氧基黄酮(17)、二氢黄芩新...     

鸡血藤化学成分的分离与结构鉴定

目的对中药鸡血藤(Spatholobus suberectus Dunn)中化学成分进行分离及结构鉴定。方法采用正相硅胶、反相ODS、Sephadex LH-20等柱色谱及高效液相色谱等手段进行分离纯化,并通过理化性质与波谱分析方法鉴定了化合物的结构。结果从鸡血藤体积分数为95%的乙醇提取物中分离鉴定了9个单体成分,分别为blumenol A(1)、(6S,7E,9R)-roseoside(2)、(6S,7E,9R)-6,9-dihydroxy-4,7-megastigman-3-one-9-O-[α-L-arabinopyranosyl-(1→6)-(β-D-glucopyranoside](3)、7S,8R-erythro-4,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-7-O-β-D-glucopyranoside(4)、(7S,8R)-dihydrodehydrodiconiferyl alcohol-4-O-(β-D-glucopyranoside(5)、(7S,8R)-3,3',5-trimethoxy-4',7-epoxy-8,5'-neolignan-4,9,9'-triol(6)、次黄苷(hypoxanthine-9-β-D-ribofuranoside,7)、烟酸(nicotinic acid,8)和丁二酸(amber acid,9)。结论其中2-8均为首次从密花豆属中分离得到的化合物。     

Flavonoids from the leaves of Pleioblastus argenteastriatus

A new flavonoid, 5,7,3'-trihydroxy-6-C-beta-D-digitoxopyranosyl-4'-O-beta-D-glucopyranosyl flavonoside (1), along with four known flavonoids 5,7,4'-trihydroxy-3',5'-dimethoxy flavone (2), 5,3',4'-trihydroxy-7-O-beta-D-glucopyranosyl flavonoside (3), 5,4'-dihydroxy-3',5'-dimethoxy-7-O-beta-D-glucopyranosyl flavonoside (4), 5,3',4'-trihydroxy-6-C-[beta-D-glucopyranosyl-(1 --> 6)]-beta-D-glucopyranosyl flavonoside (5) were isolated from 95% EtOH extract of the leaves of Pleioblastus argenteastriatus. Their structures were determined on the basis of spectroscopic techniques and chemical methods.     

白花败酱草化学成分的分离与结构鉴定

目的研究白花败酱草的化学成分。方法利用溶剂萃取后进行硅胶柱和制备液相色谱分离纯化，根据理化性质和光谱数据鉴定结构。结果分离并鉴定了8个化合物：bolusanthol B (1)，(2S)-5,7,2′,6′-四羟基-6,8-二异戊烯基-二氢黄酮(2)，orotinin (3)，(2S)-5,7,2′,6′-四羟基-6-lavandulyl-二氢黄酮(4)，3′-异戊烯基-芹黄素(5)，木犀草素(6)，槲皮素(7)和洋芹素(8)。结论化合物2，4为新化合物，1，3，5为首次从败酱属植物中分离得到，6，7，8为首次从白花败酱草中分离得到。     

Taraxasterane-type triterpene and neolignans from Geum japonicum Thunb. var. chinense F. Bolle

The phytochemical investigation of the ethanolic extract of the whole plants of Geum japonicum Thunb. var. chinense F. Bolle yielded four new compounds: 20 β,28-epoxy-28-hydroxytaraxasteran-3 β-ol (1), (7R,8R)-4-hydroxy-9'-O-(α-L-rhamnopyranosyl)-3,3',5'-trimethoxy-8-O-4'-neolignan (2), (7R,8S)-4-hydroxy-9'-O-(α-L-rhamnopyranosyl)-3,3',5'-trimethoxy-8-O-4'-neolignan (3), and (7S,8S)-5-methoxycupressoside A (4), as well as 40 other known compounds. Structures were elucidated by physical, chemical, and spectroscopic methods, including 1D and 2D NMR, HRESIMS, and CD experiments. The taraxasterane-type triterpene (1) and lignans (2- 6) are reported for the first time from the GEUM genus. Moreover, all compounds were evaluated for anti-inflammatory activities against NO production in RAW264.7 macrophages, and only moderate activities were detected.     

Phenolic compounds from the aqueous extract of Acacia catechu

Two new phenolic compounds, 5-hydroxy-2-[2-(4-hydroxyphenyl) acetyl]-3-methoxylbenzoic acid (1) and (2S,3S)-3,7,8,3',4'-pentahydroxyflavane (2), were obtained from the aqueous extract of Acacia catechu, along with four known compounds identified as rhamnetin (3), 4-hydroxyphenyl ethanol (4), 3,3',5,5',7-pentahydroxyflavane (5), and fisetinidol (6). Their structures were determined on the basis of spectroscopic analysis. Free radical-scavenging activities of the new compounds were evaluated.     

Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents.

To explore the structural requirements of (+)-cis-khellactone derivatives as novel anti-HIV agents, 24 monosubstituted 3', 4'-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) derivatives were synthesized asymmetrically. These compounds included 4 isomeric monomethoxy analogues (3-6), 4 isomeric monomethyl analogues (7-10), 4 4-alkyl/aryl-substituted analogues (11-14), and 12 4-methyl-(+)-cis-khellactone derivatives (15-26) with varying 3', 4'-substituents. These (+)-cis-khellactone derivatives were screened against HIV-1 replication in acutely infected H9 lymphocytes. The results demonstrated that the (3'R,4'R)-(+)-cis-khellactone skeleton, two (S)-(-)-camphanoyl groups at the 3'- and 4'-positions, and a methyl group on the coumarin ring, except at the 6-position, were optimal structural moieties for anti-HIV activity. 3-Methyl- (7), 4-methyl- (8), and 5-methyl- (9) 3',4'-di-O-(S)-camphanoyl-(3'R, 4'R)-(+)-cis-khellactone showed EC(50) and therapeutic index values of <5.25 x 10(-5) microM and >2.15 x 10(6), respectively, in H9 lymphocytes, which are much better than those of DCK and AZT in the same assay. Furthermore, 8 and 9 also showed potent inhibitory activity against HIV-1 replication in the CEM-SS cell line, and most monosubstituted DCK analogues were less toxic than DCK in both assays.     

马尾松松针中木脂素苷的分离与结构鉴定

目的研究松科(Pinaceae)植物马尾松(PINUS MASSONIANA Lamb.)松针(pine needles)的化学成分。方法利用DIAION HP-20,TOYOPEARL HW-40等色谱技术分离纯化,根据化合物的理化性质和光谱数据(UV,IR,MS,^{1H-1<>/supH COSY,HMQC,DEPT,HMBC和ORD等)进行结构鉴定。结果从马尾松松针水煎液的正丁醇萃取部位分离得到3个化合物,分别鉴定为化合物4(massonianoside A):(7S,8R)-3,4,9′-三羟基-3-甲氧基-7,8-二氢苯并呋喃-1′-丙醇基新木脂素-9-o-α-L-鼠李糖苷;化合物5(massonianoside C):(7S,8R)-9,9′-二羟基-3,3′-二甲氧基-7,8-二氢苯并呋喃-1′-丙醇基新木脂素-4-o-α-L-鼠李糖苷;化合物6(cedrusin-4-o-β-glucoside):(7S,8R)-3,9,9′-三羟基-3-甲氧基-7,8-二氢苯并呋喃-1′-丙醇基新木脂素-4-o-β-D-葡糖苷。结论化合物4和5为新化合物。}     

Contribution of the adenine base to the activity of adenophostin A investigated using a base replacement strategy

Syntheses of 3'-O-alpha-D-glucopyranosyl-1-beta-D-ribofuranosidoimidazole 2',3', 4'-trisphosphate (7) and 3'-O-alpha-D-glucopyranosyl-9-beta-D-ribofuranosidopurine 2',3',4'- trisphosphate (8), two analogues of the superpotent 1D-myo-inositol 1,4,5-trisphosphate receptor agonist adenophostin A (2), are described. 5-O-Benzyl-1, 2-O-isopropylidene-alpha-D-ribofuranose was prepared by an improved route from 1,2-O-isopropylidene-alpha-D-xylofuranose and was coupled with 3,4-di-O-acetyl-2,6-di-O-benzyl-D-glucopyranosyl dimethyl phosphite to give 3',4'-di-O-acetyl-2',5, 6'-tri-O-benzyl-3-O-alpha-D-glucopyranosyl-1, 2-O-isopropylidene-alpha-D-ribofuranose. Removal of the isopropylidene acetal and subsequent acetylation gave the central disaccharide 1,2,3',4'-tetra-O-acetyl-2',5, 6'-tri-O-benzyl-3-O-alpha-D-glucopyranosyl-D-ribofuranose. Vorbrüggen condensation with activated imidazole or purine gave the required beta-substituted derivatives which were further elaborated to 7 and 8, respectively. Radioligand binding assays to hepatic InsP(3) receptors and functional assays of Ca(2+) release from permeabilized hepatocytes gave a rank order of potency of the ligands 2 approximately 8 > 7 approximately Ins(1,4,5)P(3) indicating that the N(6)-amino group of 2 is of little importance for activity and that a minimum of a two-fused-ring nucleobase is required for activity to exceed that of Ins(1,4,5)P(3). The role of the adenine base in the activity of the adenophostins is discussed. This general method should facilitate ready access to nucleobase-modified adenophostin analogues for SAR studies.     

Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents

Our recent studies demonstrated that d- and l-2'-fluoro-2',3'-unsaturated nucleosides (d- and l-2'-F-d4Ns) display moderate to potent antiviral activities against HIV-1 and HBV. As an extension of these findings, beta-d-3'-fluoro-2',3'-unsaturated nucleosides were synthesized as potential antiviral agents. The key intermediate (2S)-5-(1,3-dioxolan)-1-benzoyloxy-3,3-difluoropentan-2-ol 6 was prepared from 2,3-O-isopropylidene-d-glyceraldehyde 1, which was converted to 5-O-benzoxy-d-2-deoxy-3,3-difluoropentofuranosyl acetate 7 by the ring-closure reaction under acidic conditions. The acetate 7 was condensed with silylated purine and pyrimidine bases, which produced the alpha and beta isomers. The 3',3'-difluoro nucleosides were then treated with t-BuOK to give the desired 3'-fluoro-unsaturated nucleosides. We studied the structure-activity relationships of d-3'-fluoro-2',3'-unsaturated nucleosides against HIV-1 in human peripheral blood mononuclear cells, from which we found that the cytosine derivative 26 was the most potent among the synthesized compounds. To understand the mode of action and drug resistance profile, with particular regard to the role of fluorine, we performed the molecular modeling studies of the cytidine analogue d-3'F-d4C and found a good correlation between calculated relative binding energies and activity/resistance data. Our model also shows interactions of the 3'-fluorine and the 2',3' double bond, which can be correlated to the observed biological data. Differences between fluorine substitution at the 3' and 2' positions may account for the higher cross-resistance with lamivudine observed in the 2'-fluorinated series.     

多叶姜黄(Curcuma comosa Roxb.)的化学成分

目的对泰国产姜科姜黄属植物多叶姜黄(Curcuma comosaRoxb.)干燥根茎甲醇提取物的化学成分进行分离和结构鉴定。方法C.comosaRoxb.的甲醇提取物经乙酸乙酯-正丁醇-水依次萃取后,对各萃取部分采用正-反相硅胶柱色谱和制备型HPLC进行分离,经理化常数测定、核磁共振技术分析等方法鉴定了化合物的结构。结果分离得到8个化合物,分别被鉴定为异蓬莪术环二烯酮(isofuranodienone,1),蓬莪术环二烯酮(furanodienone,2),1(10)Z,4Z-蓬莪术二烯-6-酮[1(10)Z,4Z-furanodiene-6-one,3],泽泻醇(alismol,4),2,2,6-三甲基-1-氧螺[2,5]辛-5-烯-4-醇(2,2,6-trimethyl-1-oxaspiro[2,5]oct-5-en-4-ol,5),1-羟基-α,α,4-三甲基-3-环己烯-1-甲醇(1-hydroxy-α,α,4-trimethyl-3-cyclohexene-1-methanol,6),6-羟基-3(1-羟基-1-甲基乙基)-6-甲基-2-环己烯-1-酮(6-hydroxy-3(1-hydroxy-1-methylethyl)-6-methyl-2-cyclo-hexen-1-one,7),(1S,2S,4R)-1,8桉叶素-2-O-β-D-葡萄糖苷((1S,2S,4R)-2-hydroxy-1,8-cineoleβ-D-glucopyranoside,8)。结论化合物3~8为首次从该属植物中分离得到。     

Biosynthesis of the macrolide antibiotic patulolides by Penicillium urticae S11R59: identification of the origin of carbon atoms by 13C NMR spectroscopy

Patulolides are 12-membered macrolides produced by Penicillium urticae S11R59, and they are the simplest macrolide antibiotics. All carbon signals, including six methylene signals of patulolides A (1), B (2), and C (3), were completely assigned by use of the 13C two-dimensional INADEQUATE. The biosynthesis of patulolides was investigated with 13C labeled acetate. Feeding of [1-13C]acetate to a culture of P. urticae S11R59 gave patulolides A (1), B (2), C (3), each of which showed enrichment at carbons 1, 3, 5, 7, 9, and 11; enrichment at carbons 2, 4, 6, 8, 10, and 12 was observed upon feeding of [2-13C]acetate. These results showed that patulolides A (1), B (2), and C (3) are pure acetogenic hexaketides derived from six acetate units coupled in head-to-tail fashion.     

Toxicity and Microsomal Enzyme Induction Effects of Several Polybrominated Biphenyls of Firemaster

Toxicity and Microsomal Enzyme Induction Effects of SeveralPolybrominated Biphenyls of Firemaster. Dannan, G.A., Sleight,S.D. and Aust, S.D. (1982). Fundam. Appl. Toxicol. 2:313-321.Some toxicological and pharmacological effects of 2,4,5,2',5'-penta-(congener 1), 2,3,4,2',4',5'-hexa- (congener 5), 2,4,5,3',4',5'-hexa-(congener 6), 2,3,4,5,3',4',-hexa- (congener 7), and 2,3,4,5,2',3',4'-hepta-bromobiphenyl(congener 9) were evaluated in male rats given a single 90 mg/kgip injection and killed seven days later. Only congener 7 depressedbody weight gain, spleen and thymus weights, and caused severehistopathological changes in the thymus. Congener 7 caused thelargest increase in liver weight and the most changes in liverpathology while congener 1 failed to enlarge this organ andcaused the mildest ultrastructural changes. Liver microsomeswere isolated and evaluated for enzyme induction from all treatedrats except those administered congener 6, which was previouslyidentified as a mixed-type enzyme inducer (Dannan et al. 1978b).All congeners increased the liver microsomal cytochrome P-450content, but only congener 7 shifted the carbon monoxide differencespectrum absorption maximum to 448.0 nm. The microsomal ethylisocyanide difference spectrum 455/430 nm ratio was increasedthe most by congener 7 (3 fold). All congeners increased cytochromeP-450 reductase and microsomal epoxide hydrase activities bynearly 1.5–3 fold. Congener 7 failed to induce amino-pyrine-N-demethylaseactivity but the remaining congeners increased it by 2 fold.Congener 7 was the most effective inducer of benzo[a]pyrenehydroxylase and p-nitrophenol UDP-glucuronyl transferase. Theseresults add to the suggestion that the presence of an orthohalogen on a polyhalo-genated biphenyl does not completely abolishtoxicity or 3-methylcholanthrene-type microsomal enzyme induction.     

剑叶血竭素国产血竭中一个新的二聚查耳酮

目的　研究国产商品血竭的活性成分。方法　用甲醇提取,SephadexL-20,MCIgel和硅胶柱色谱进行分离纯化,用现代波谱学方法进行结构鉴定。结果　从国产雨林牌血竭的甲醇浸提物中得到9个查耳酮化合物,分别鉴定为:1-［5-(2,4,4′-三羟基二氢查耳酮基)］-1-对羟基苯基-3-(2-甲氧基-4-羟基苯基)-丙烷(1),2′-methoxysocotrin-5′-ol(2),socotrin-4′-ol(3),2-甲氧基-4,4′-二羟基二氢查耳酮(4),2,4,4′-三羟基二氢查耳酮(5),2,4,4′-三羟基-6-甲氧基二氢查耳酮(6),2′,4′,4-三羟基查耳酮(7),2-甲氧基-4,4′-二羟基查耳酮(8),2′-甲氧基-4′,4-二羟基查耳酮(9)。结论　1为一新的查耳酮二聚体,命名为剑叶血竭素(cochinchinenin),2-9为首次从该血竭中分离得到。     

New sesquiterpene lactone and neolignan glycosides with antioxidant and anti-inflammatory activities from the fruits of Illicium oligandrum

Phytochemical investigations of the fruits of Illicium oligandrum resulted in a new sesquiterpene lactone, 3 beta-benzoyloxy-10-deoxyfloridanolide (1), and three new neolignan glycosides, including two dihydrobenzofuran neolignan glycosides, (7 R,8 S)-9-O-beta-D-xylopyranosyl-9'-O-alpha- L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (2) and (7 R,8 S)-9-O-shikimoyl-4-O-beta-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (3) and one 8- O-4' neolignan glycoside, (7 S,8 R)-1-[4-O-(beta-D-glucopyranosyl)-3-methoxyphenyl]-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]-1,3-propanediol (4), together with three known sesquiterpene lactones (5 - 7) and two known neolignan glycosides (8 and 9). Their structures were elucidated on the basis of 1D, 2D NMR, HR-MS and chemical evidence. Compounds 3 and 4 showed moderate antioxidant activity with the inhibitory rates 13.30% and 9.30% at 1.0 x 10(-5) M, respectively. Compounds 3 and 9 exhibited anti-inflammatory activity with the inhibitory rates 67.0% and 51.0% at 1.0 x 10(-5) M, respectively.     

芝麻花化学成分的研究

芝麻花为胡麻科植物胡麻Sesamum indicum L.(S.orientale L.)的干燥花,有生发、消肿之功效,可治疗脱发、冻疮、便秘等。民间单方芝麻花治疗寻常疣、扁平疣等,均有满意的疗效。目前人们对芝麻种子的化学成分研究较多,但尚没有人对芝麻花的化学成分进行系统研究。本研究运用硅胶柱、凝胶柱、反相柱等多种色谱方法进行分离纯化,并根据理化性质和波谱数据鉴定化合物的结构。从其乙醇提取物的乙酸乙酯和正丁醇部位分别得到10个化合物,分别鉴定为latifonin (1),苦瓜脑苷(momor-cerebroside,2),大豆脑苷II(soya-cerebroside II,3),1-O-β-D-葡糖-(2S,3S,4R,5E,9Z)-2-n-(2′-羟基二十四碳酰氨基)-1,3,4-三羟基-十八碳-5,9-二烯［1-O-β-D-glucopyranosyl-(2S,3S,4R,5E,9Z)-2-n-(2′-hydroxytetra-cosanoyl) 1,3,4-trihydroxy-5,9-octadienine,4］,1-O-β-D-葡糖-(2S,3S,4R,8Z)-2N-(2′-羟基二十四碳酰氨基)-3,4-二-羟基-8-十八碳烯［1-O-β-D-glucopyranosyl-(2S,3S,4R,8Z)-2-n-(2′R) 2′-hydroxytetracosanoyl)-3,4-dihydroxy-8-octadene,5］,2-乙酰橙酰胺［(2S,1″S)-aurantiamide acetate,6］,苯基乙醇-O-(2′-O-β-D-吡喃鼠李糖,3′-O-β-D-吡喃葡糖)-β-D-吡喃葡糖［benzyl alcohol-O-(2′-O-β-D-xylopyranosyl, 3′-O-β-D-glucopyranoside)-β-D-glucopyranoside,7］,β-谷甾醇(8),胡萝卜苷(9),D-半乳糖醇(10)。其中化合物4为新化合物,所有化合物均为首次从该植物的花中分离得到。     

Flavonoid constituents of Melicope triphylla MERR.II

From the leaves of Melicope triphylla MERR., three new flavonoids (1-3) were isolated, together with nine known flavonoids, 4',5-dihydroxy-3,3',7- trimethoxyflavone (4), 5-hydroxy-3,3',4',7-tetramethoxyflavone (5), 3,3',4',5,7-pentamethoxyflavone (6), 7-hydroxy-3,3',4',5,8-pentamethoxyflavone (7), 3,3',4',5,7,8-hexamethoxyflavone (8), 5-hydroxy-3,7,8-trimethoxy-3',4'-methylenedioxyflavone (9), 7-hydroxy-3,5,8- trimethoxy-3',4'-methylenedioxyflavone (10), 3,5,7,8-tetramethoxy-3',4'-methylenedioxyflavone (11), and 5-hydroxy- 3,6,7,8-tetramethoxy-3',4'-methylenedioxyflavone (12). The structures of 1, 2, and 3 were established as 5-hydroxy-3,7-dimethoxy-3',4'-methylenedioxyflavone, 5-hydroxy-7-isopentenyloxy-3,8-dimethoxy-3',4'-methylenedioxyfl avone, and 4'-hydroxy-7-isopentenyloxy-3,3',5,8-tetramethoxyflavone by their respective chemical and spectral data. The 20 flavonoids isolated from this plant were examined for the piscicidal activities.