New diarylheptanoids from the stems of Carpinus cordata

Two new diarylheptanoids, carpinontriols A (1) and B (2), were isolated from the stems of Carpinus cordata, along with the known diarylheptanoid, casuarinondiol (3), and five known compounds, (+)-catechin (4), methyl gallate (5), methyl gallate 3-O-beta-D-glucopyranoside (6), methyl gallate 4-O-beta-D-glucopyranoside (7), and methyl gallate 3-O-beta-D-(6'-O-galloyl)-glucopyranoside (8). The structures of 1 and 2 were elucidated by spectral methods. Among the isolated compounds, compounds 4-6 and 8 showed radical-scavenging activity in the DPPH assay.     

Flavonoids from Dalbergia louvelii and their antiplasmodial activity

Four new flavonoids (1-4), along with 13 known compounds, were isolated from the heartwood of Dalbergia louvelii by following their potential to inhibit in vitro the growth of Plasmodium falciparum. Of the isolated compounds, four known compounds showed antiplasmodial activity with IC(50) values ranging from 5.8 to 8.7 microM, namely, (R)-4' '-methoxydalbergione (5), obtusafuran (6), 7,4'-dihydroxy-3'-methoxyisoflavone (7), and isoliquiritigenin (8). The structures of the new compounds were determined using spectroscopic techniques as 1-(3-hydroxyphenyl)-3-(4-hydroxy-2,5-dimethoxyphenyl)propane (1), spirolouveline (2), (3R)-7,2'-dihydroxy-4',5'-dimethoxyisoflavanone (3), and 3-(2,4-dihydroxy-5-methoxy)phenyl-7-hydroxycoumarin (4), respectively.     

紫玉盘化学成分的研究

目的：从紫玉盘Uvaria macrophylla var. microcarpa中分离具有抗癌活性成分。方法：用色谱方法分离紫玉盘中化学成分,用波谱技术（IR,ESI-MS,1H-NMR,13C-NMR,HMQC,COSY,HMBC, NOESY)进行鉴定结构。结果：从紫玉盘中分离得到4个化合物, uvarimacrins A （1）, B（2）and C（4）和uvamalols D（3）。结论：化合物（1）,（2）,（4）均为新化合物,（3）首次从紫玉盘中分离得到。     

Constituents of the stigmas of Crocus sativus and their tyrosinase inhibitory activity

Four new compounds, crocusatins F (1), G (2), H (3), and I (4a), together with 21 known compounds, were isolated from an aqueous extract of the stigmas of Crocus sativus (saffron). The structures of 1-4 were established by spectral methods. The tyrosinase inhibitory activities of all 25 compounds isolated were evaluated in vitro using mushroom tyrosinase. Among them, crocusatin H (3), crocin-1 (5), and crocin-3 (6) showed significant tyrosinase inhibitory activity.     

Phenolic compounds of Dragon's blood from Dracaena draco

Three new compounds, 2,4,4'-trihydroxydihydrochalcone (1), 3-(4-hydroxybenzyl)-5,7-dimethoxychroman (2), and 7-hydroxy-3-(4-hydroxybenzyl)chromone (3), were isolated from the resin "Dragon's blood" obtained from Dracaena draco along with 18 known compounds. The structures of 1, 2, and 3 were determined using MS and NMR techniques.     

Alpha-glucosidase inhibitory anthranols, kenganthranols A-C, from the stem bark of Harungana madagascariensis

One new prenylated 1,4-anthraquinone and three new prenylated anthranols, named kengaquinone (1) and kenganthranols A (2), B (3), and C (4), were isolated from a hexane extract of the stem bark of Harungana madagascariensis. Six known compounds including anthraquinones, anthrones, and xanthones were also isolated and identified. The structures of the new compounds were determined by analysis of spectroscopic data and comparison with data of previously known analogues. Some isolated compounds (3-5, 7-11) were evaluated for their alpha-glucosidase inhibition activity. Compounds 3, 4, 8, and 11 showed significant activity, whereas compounds 7, 9, and 10 were inactive in this test.     

Potent cytotoxic lignans from Justicia procumbens and their effects on nitric oxide and tumor necrosis factor-alpha production in mouse macrophages

A new lignan glycoside, 4-O-alpha-L-arabinopyranosyl-(1' "-->2' ')-beta-D-apiofuranosyldiphyllin (2), named procumbenoside A, and 11 known compounds were isolated from the whole plant of Justicia procumbens. The structure of 2 was established by spectral analysis and chemical methods. The known compounds justicidin A (1), diphyllin (3), and tuberculatin (4) showed potent cytotoxic effects against a number of cancer cells in vitro. Compounds 1 and 4 also strongly enhanced tumor-necrosis factor-alpha (TNF-alpha) generation from mouse macrophage-like RAW 264.7 cells stimulated with lipopolysaccharide (LPS).     

New 4-methoxybenzoyl derivatives from the ascidian Polycarpa aurata.

From the hydrophilic extract of the ascidian Polycarpa aurata three new compounds, N-(4-methoxybenzoyl)-N'-methylguanidine (1), butyl 2-(4-methoxyphenyl)-2-oxoacetate (2), and 2-(4-methoxyphenyl)-N-methyl-2-oxoacetamide (3), together with the known compounds methyl 2-(4-methoxyphenyl)-2-oxoacetate (4) and 4-methoxybenzoic acid were isolated. The structures of all isolates were determined from their spectroscopic data (NMR, MS, IR, UV).     

Anthraquinones with quinone reductase-inducing activity and benzophenones from Morinda citrifolia (noni) roots

Two new benzophenones, morintrifolins A ( 1) and B ( 2), together with 14 known anthraquinones and four other known compounds, were isolated from a chloroform-soluble extract of Morinda citrifolia roots. Of the isolated compounds, four known anthraquinones, namely, 1,2-dihydroxyanthraquinone ( 3), 1,3-dihydroxy-2-methylanthraquinone ( 4), 2-hydroxy-3-(hydroxymethyl)anthraquinone ( 5), and 1,3,6-trihydroxy-2-methylanthraquinone ( 6), exhibited quinone reductase (QR)- inducing activity in Hepa lclc7 cells, with concentrations required to double QR activity of 12.0, 8.1, 0.94, and 0.56 microM, respectively.     

Cytotoxic diacetylenic spiroketal enol ethers from Plagius flosculosus

Three new diacetylenic spiroketal enol ethers named flosculins A (1), B (2), and C (3), along with five known compounds (4-8) of the same structural class, were isolated from the leaves of Plagius flosculosus. The structures were deduced by extensive 1D and 2D NMR spectroscopy and mass spectrometry. All isolated compounds exhibited significant cytotoxic activity against leukemia cells (Jurkat T and HL-60). Compounds 5-8 induced apoptosis in HL-60 cells with corresponding IC(50) values ranging from 4 to 6 microM.     

Three new sesquiterpenes from roots of Curcuma longa

Objective: To study the chemical constituents from the roots of Curcuma longa. Methods: The structures of the new compounds were elucidated based on extensive spectral analysis, including 1D and 2D NMR, MS, UV, and CD analysis. Results: Two new sesquiterpene compounds (1S,2R,5R,7S,8R)-2,8-epoxy-5-hydroxybisabola-3,10-dioen-9-one (1), (1R,2R,5R,7S,8R)-2,8-epoxy-5-hydroxybisabola-3,10-dioen-9-one (2), and a new natural product 6-(4-Hydroxymethylphenyl)-2-methyl-hept-2-ene-4-one (3) together with three known compounds ar-turmerone (4), 2-methyl-6-(4-hydroxyphenyl-3-methyl)-2-hepten-4-one (5) and 2-methyl-6-(4-hydroxyphenyl)-2-hepten-4-one (6) were isolated from C. longa root extract with 95% ethanol. Conclusion: In the study, three new compounds were isolated from C. longa, and their absolute configurations were determined.     

Antiinflammatory constituents from Heterotheca inuloides

Three new compounds, cadalen-15-oic acid (1), 3,7-dihydroxy-3(4H)-isocadalen-4-one (2), and dicadalenol (3), were isolated from the aerial parts of Heterotheca inuloides (Mexican arnica), together with the known compounds 7-hydroxycadalene (4), 7-hydroxy-4alphaH-3,4-dihydrocadalene (5), 1alpha-hydroxy-1(4H)-isocadalen-4-one (6), 1alpha-hydroxy-4alphaH-1,2,3,4-tetrahydrocadalen-15-oic acid (7), 7-(3,3-dimethylallyloxy)coumarin, caryolan-1,9beta-diol, and quercetin. The structures of the new compounds were elucidated by spectroscopic methods. The antiinflammatory activities of the extracts and the isolated compounds were evaluated by determining the inhibition of TPA-induced mouse ear edema. The natural products 3, caryolan-1,9beta-diol, and quercetin were the most active substances tested and displayed dose-dependent activities.     

Batzelline D and isobatzelline E from the indopacific sponge Zyzzya fuliginosa

Two new pyrroloquinoline alkaloids, isobatzelline E (1) and batzelline D (2), together with the known compounds batzelline C (3), isobatzelline C (4), and makaluvamine D (5), were isolated from an Indopacific collection of the marine sponge Zyzzya fuliginosa; the known compounds makaluvamines A (9), H (10), J (7), K (8), and P (6) were obtained from Z. fuliginosa collected in Papua New Guinea. The structures were elucidated by interpretation of 1D (1)H and (13)C NMR spectra and 2D HSQC and HSQC-LR spectra. Compounds 1-10 were isolated because the crude extracts of both Zyzzya species inhibited HIV-1 envelope-mediated cell fusion. However, the inhibition profile observed for the pure compounds 1-10 mirrors that reported for the inhibition of topoisomerase II by other pyrroloquinolines, leaving open the possibility that the activity results from interactions with DNA-modifying enzymes.     

Furan metabolites from the sponge-derived yeast Pichia membranifaciens

Five new compounds, pichiafurans A-C (1-3) and pichiacins A and B (4 and 5), along with five known compounds (6-10), have been isolated from the yeast Pichia membranifaciens derived from a marine sponge Petrosia sp. Their structures were elucidated by 1D and 2D NMR and mass spectrometry techniques. Pichiafurans are rare examples of monofurano metabolites isolated from yeast.     

Cytotoxic steroidal alkaloids from Kibatalia laurifolia

Four new steroids, 3-epi-gitingensine (1), N-acetylgitingensine (6), kibalaurifoline (7) and kibalaurifenone (8), along with the known paravallarine (2), 7α-hydroxyparavallarine (3), gitingensine (4), and N-methylgitingensine (5) were isolated from the leaves of Kibatalia laurifolia. Their structures were determined primarily from mass spectrometry and 2D NMR analyses. On the basis of the known absolute configurations of 2 and 4, the absolute configurations of the new compounds were proposed. Due to the structural relationships of compounds 1-8, a biosynthetic pathway was suggested. Compound 2 was cytotoxic to KB cells (IC50 12.8 μM), followed by 1 with IC50 21.2 μM.     

冬凌草中的一个新生物碱

目的:研究冬凌草(Rabdosia rubescens (Hemls.) Hara)地上部分的化学成分。方法:利用大孔吸附树脂色谱进行分离纯化,根据化合物的理化性质和光谱数据鉴定结构。结果:从冬凌草地上部分分离得到7个化合物,分别为:冬凌草碱(1),黄嘌呤(2),芹菜素-6,8-二-C-β-D-葡萄糖苷(3),7-羟基-4(1H)-喹啉酮(4),1,5-二-(3,4-二羟基苯基)-乙烯醚(5),3-(3,4-二羟基苯基)-2-异丙氧基-丙酸(6),邻苯二甲酸双-(2-乙基己基)酯(7)。结论:化合物1为新化合物,其余化合物均为首次从该属植物中分离得到。     

Cytotoxic isomalabaricane triterpenes from the marine sponge Rhabdastrella globostellata

Fourteen isomalabaricane triterpenes were isolated from the marine sponge Rhabdastrella globostellata. In addition to the known compounds globostellatic acids A (1) and D (4) and stelliferin riboside (13), 11 of the compounds were new natural products, which included globostelletin (3), eight new globostellatic acid congeners, F to M (2, 5-11), and two new stelliferin ribosides (12 and 14). The isolated compounds were tested against three different cancer cell lines, L5178Y (mouse lymphoma), HeLa (human cervix carcinoma), and PC-12 (rat pheochromocytoma). The isomalabaricane derivatives were found to be selectively active toward the mouse lymphoma cell line L5178Y. The structures were determined by 1D and 2D NMR data and by comparison with spectroscopic data of known related compounds.     

Cytotoxic lavandulyl flavanones from Sophora flavescens

Two new lavandulylated flavanones, (2S)-2'-methoxykurarinone (1) and (-)-kurarinone (2), were isolated from the root of Sophora flavescens, together with two known lavandulyl flavanones, sophoraflavanone G (3) and leachianone A (4), and two known isoflavonoids, formononetin and l-maakiain. The structures of 1 and 2 were determined on the basis of optical rotation and spectral evidence and by comparison with known compounds. Compounds 1-4 exhibited cytotoxic activity against human myeloid leukemia HL-60 cells.     

藏药樱草杜鹃中的酚类成分

 目的 研究藏药樱草杜鹃（Rhododendron primulaeflorum Bur.et Franch.）的嫩枝和嫩叶中的酚类成分。方法 利用色谱方法分离和纯化化合物,并通过光谱方法及理化性质鉴定其结构。结果 从樱草杜鹃中分离得到8个酚类化合物,分别鉴定为cannabichromeorcinic acid(1)、苔色酸甲酯(2)、苔色酸(3)、苔黑酚-O-β-D-吡喃葡萄糖苷(4)、2,6-二甲氧基-4-羟基苯酚-1-O-β-D-吡喃葡萄糖苷(5)、lyoniside(6)、4,6-二羟基-2-O-(β-D-吡喃葡萄糖苷)苯乙酮(7)、3,5-二羟基-4-O-(β-D-吡喃葡萄糖苷)苯乙酮(8)。结论 除化合物2外,其余化合物均为首次从该植物中分离得到。     

Two new minor polybrominated dibenzo-p-dioxins from the marine sponge Dysidea dendyi

Two new minor tribromodibenzo-p-dioxins, spongiadioxin C (1) and its methyl ether (2), were isolated from an Australian marine sponge Dysidea dendyi, together with the known minor metabolites methyl ethers of spongiadioxins A (4) and B (6) and polybrominated diphenyl ethers (7-9). The structures of the new compounds were established by 1D and 2D NMR spectroscopy and confirmed by synthesis of 2 from diphenyl ether 9. All isolated compounds inhibited the cell division of fertilized sea urchin eggs.