Unusual naphthoquinones, catechin and triterpene from Byrsonima microphylla

The new triterpene Delta1-lupenone (1), together with lupeol, beta-amyrin and betulin were isolated from the wood of Byrsonima microphylla (Malpighiaceae). The new compounds 3-hydroxy-2-methoxy-8,8,10-trimethyl-8H-antracen-1,4,5-trione (2), 3,7-dihydroxy-2-methoxy-8,8,10-trimethyl-7,8-dihydro-6H-antracen-1,4,5-trione (3), (2S*,10aR*)-2,8-dihydroxy-6-methoxy-1,1,7-trimethyl-2,3,10, 10a-tetrahydro-1H-fenantren-9-one (4) and (2S,3S)-3'-hydroxy-4',5,7-trimethoxy-flavan-3-ol (5) were also isolated through monitored TLC using the antioxidant beta-carotene reagent. The antioxidant potential of the compounds 2-5 was measured and none of them showed activity. The structures of these compounds were elucidated by chemical and spectroscopic analysis based on NMR techniques (1H, 13C NMR, COSY, nOe difference, HMQC and HMBC), UV and MS.     

东当归化学成分研究及定量分析

从当归属植物东当归的根的乙醇溶液中分离得到了4个化合物,通过理化特性和波谱分析分别鉴定为双(5-甲酰基糠基)醚(bis(5-formylfurfuryl)ether,1)、5-羟甲基糠醛(5-hydroxymethyl-2-furaldehyde,2)、豆甾醇(stigmasterol,3)、十七烷酸(heptadecanoic acid4,)。所有化合物均为首次从该植物中分离得到,其中1为首次从该属植物中分离得到。采用高效液相色谱法对东当归所含该属特征活性成分紫花前胡素进行了定量分析。     

珠子草化学成分的研究

利用大孔树脂吸附和多种柱层析方法,从珠子草中分离得到5个化合物,根据理化数据和波谱学等方法鉴定为柯里拉京(1)、芦丁(2)、isobubbialine(3)、丁二酸(4)和没食子酸(5)。根据2D-NMR修正了化合物3的部分碳信号归属,归属了化合物1的碳氢谱数据。     

Chemical constituents from Celastrus aculeatus Merr.

Phytochemical investigation of Celastrus aculeatus Merr. led to the isolation of nine compounds. Their structures were identified to be dulcitol (1), β-sitosterol (2), n-tritriacontane (3), nimbidiol (4), pristimerin (5), p-hydroxybenzoic acid (7), vanillic acid (8), 3, 5-dimethoxy-4-hydroxybenzoic acid (9) and a new compound named pristimerol (6) on the basis of mass and NMR spectra. This is the first report of phenolic acids (compounds 7–9) from C. aculeatus Merr. We present the HR-MS, 1D NMR (¹H, ¹³C NMR, DEPT) and 2D NMR (HMBC) data of the new compound (6).     

Alpha-pinene-type monoterpenes and other constituents from Artemisia suksdorfii

Two alpha-pinene-type monoterpenes, 7-hydroxymyrtenol (1) and 7-hydroxymyrtenal (2), a inositol derivative, (+)-quebrachitol (3) and two p-menthene triols (4 and 5), in addition to two known compounds were isolated from the aerial parts of Artemisia suksdorfii. The structures of the isolated compounds were established by analysis of spectroscopic data (IR, HR-MS, (1)H and (13)C NMR), including high-field 2D NMR techniques ((1)H-(1)H COSY, HMQC, HMBC and NOE) and in case of 3 was confirmed by X-ray analysis.     

齐墩果酸氧化产物的成分研究

以齐墩果酸为原料,分别用高锰酸钾和SeO2/H2O2(30%)进行氧化。从产物中分离得到3个化合物,经1H NMR、13C NMR、2D-NMR、MS等波谱分析,分别鉴定为3,11-二羰基-12,17-二烯-28-去甲基齐墩果烷(1)、3β-羟基-11-烯-13,28-内酯-齐墩果烷(2)和3α,12β,13α-三羟基-28-羧基齐墩果烷(3),收率依次是4.5%、6.4%、2%,其中化合物1和3为新化合物。     

Studies on the Chemical Constituents of Gnetum montanum Markg

Six compounds had been isolated from the stem of Gnetum montanum Markgr, on the basis of spectral analysis (UV, IR, 1H NMR, 13C NMR and MS), physico-chemical constants and preparation of the derivative. They were identified as 2-hydroxy-3-methoxyl-4-methoxycarbonyl pyrrole (1), 2-hydroxy-3-methoxymethyl-4-methoxycarbonyl pyrrole (2), 3,4′-dihydroxy-4-methoxy-dibenzyl ether (3), 3, 3′,4′-trihydroxy-4-methoxy-dibenzy ether (4), 2,3-diphenyl-pyrrole (5) and aminemethyl-methyl alcohol (6). (1)—(4) are new compounds,     

New anti-inflammatory ergostane-type ecdysteroids from the sclerotium of Polyporus umbellatus

Bioassay-guided fractionation of the ethyl acetate extract from the sclerotium of Polyporus umbellatus resulted in the isolation of three new ergostane-type ecdysteroids, named polyporoid A (1), B (2), and C (3), together with five known ecdysteroids. The structures of the new compounds were determined on the basis of extensive spectroscopic data (IR, MS, (1)H and (13)C NMR, and 2D NMR) analyses. All compounds (1-8) exhibited potent anti-inflammatory activity in the test of TPA-induced inflammation (1 microg/ear) in mice, with ID(50) values in the range of 0.117-0.682 microM/ear.     

Tetralones and flavonoids from Pyrola calliantha

Two new tetralones, pyrolones A (1) and B (2), and a new flavonol glycoside, 2'-O-(4-hydroxybenzoyl)hyperin (3), were isolated from Pyrola calliantha (whole plant), together with six structurally related compounds, including 2'-O-galloylhyperin (4), hyperin (5), formononetin (6), quercetin 3-O-alpha-L-arabinopyranoside (7), quercetin 3-O-alpha-L-arabinofuranoside (8), and kaempferol 3-O-beta-D-galactopyranoside (9). The structures and absolute configurations of the new compounds were elucidated on the basis of spectroscopic (UV, ORD, CD, NMR) and mass-spectrometric (HR-ESI-MS) analyses.     

Chalconoids from Fissistigma bracteolatum

Phytochemical studies on the leaves of Fissistigma bracteolatum yielded besides the two known compounds 2-hydroxy-3,4,6-trimethoxychalcone (1) and 5,7,8-trimethoxyflav-3-ene (2), five new chalconoids 2-hydroxy-3,4,6-trimethoxychalcene (3), 2-hydroxy-3,4,6-trimethoxydihydrochalcone (4), 2'-hydroxy-3',4',6'-trimethoxydihydrochalcone (5), 2'-hydroxy-3',4',6'-trimethoxy-beta'-methoxychalcane (6) and 2'-hydroxy-3',4',6'-trimethoxy-beta'-ethoxychalcane (7). The structures of these compounds were determined by mass and NMR spectroscopic methods.     

Phenolic derivatives from Aster indicus

Investigation of the constituents of whole herbs of Aster indicus L. led to isolation of 4-hydroxy-3-[1-(methoxycarbonyl)vinyloxy]benzoic acid (1), 5-(1-carboxylvinyloxy)-2-hydroxybenzoic acid (2), 4-allyl-2,6-dimethoxyphenyl 3-methylbutanoate (3), and 4-allyl-2-methoxyphenyl 2-methylbutanoate (4), together with 27 previously known compounds. The structures of compounds 1-4 were established by application of spectroscopic (NMR and MS) analyses.     

土壤真菌Curvularia affinis HS-FG-196抗肿瘤化学成分的再研究

为对土壤真菌Curvularia affinis HS-FG-196的次级代谢产物及其体外抗肿瘤活性进行进一步研究。实验采用大孔吸附树脂HP-20树脂柱、硅胶柱、凝胶LH-20柱及半制备高效液相色谱柱从Curvularia affinis HS-FG-196的发酵培养物中分离得到六个单体化合物(1～6)。利用~1H NMR、¹³C NMR、~1H-~1H COSY、HMQC、HMBC、IR、UV和MS等波谱分析方法对其进行了结构鉴定,分别是:pyrenocine S (1)、pyrenocine B (2)、pyrenocine E (3)、pyrenocine I (4)、pyrenochaetic acid B (5)和pyrenochaetic acid C (6),其中化合物1是新化合物。对所得单体化合物进行了体外抗肿瘤活性测试,结果显示化合物1、2、3对肿瘤细胞A549、HCT-116、ACHN、K562和HepG2表现出较强的活性。     

黄鞘蕊花中的艾里莫芬烷型倍半萜(英文)

从黄鞘蕊花 (ColeusxanthanthusC .Y .WuetY .C .Huang)的乙酸乙酯部分首次分离得到 3个艾里莫芬烷型倍半萜类化合物 ( 1～ 3) ,其结构由NMR波谱技术及单晶X衍射分析确定。其中 ,化合物 1为新化合物 ,命名为 8,9_断裂_艾里莫芬_1 ( 1 0 ) ,7( 1 1 )_二烯_8,1 2_内酯_9_酸。首次对化合物 2 ( 2 ,9_二氧代优瑞坡森 )和 3( 9_氧代宽眼菊素 )的1H NMR和13C NMR谱进行了全归属。     

Bafoudiosbulbins F and G, further clerodane diterpenoids from Dioscorea bulbifera L. var sativa and revised structure of Bafoudiosbulbin B

From the bulbils of Dioscorea bulbifera L. var sativa, two clerodane diterpenoids, Bafoudiosbulbins F (1) and G (2), together with five known compounds: Bafoudiosbulbins A-C, 3,5,4'-trihydroxy-3'-methoxybibenzyl, and kaempferol were isolated. Their structures were established by spectroscopic techniques, including (1)H, (13)C NMR, NOESY, ROESY, COSY, TOCSY, HSQC, and HMBC. The relative stereochemistry of compounds 1 and 2 was assigned on the basis of X-ray crystallographic diffraction analysis. Furthermore, the structure of Bafoudiosbulbin B was revised using extensive 2D NMR techniques as well as chemical transformation.     

中国红豆杉枝叶中的紫杉烷二萜

从中国红豆杉(Taxus chinensis)枝叶的乙醇提取物中分离得到8个紫杉烷二萜,通过波谱分析分别确定为：14p羟基巴卡亭Ⅵ(1),巴卡亭Ⅵ(2),巴卡亭Ⅳ(3),1β-去羟基巴卡亭Ⅳ(4),云南红豆杉酯甲(5),2α-去乙酰-2α-苯甲酰基-13α-乙酰基云南紫杉亭(6),5α-羟基-2α,7βp,9α,10β,13α-五乙酰氧基紫杉-4(20),11-二烯(7)和Taxaein(8)。其中化合物1为新化合物,并报道八个化合物在丙酮中测得的核磁共振信号,化合物8的数据属首次报道。     

Chemical constituents of rice (Oryza sativa) hulls and their herbicidal activity against duckweed (Lemna paucicostata Hegelm 381)

Four new compounds, stigmastanol-3beta-p-glyceroxydihydrocoumaroate (1), stigmastanol-3beta-p-butanoxydihydrocoumaroate (2), lanast-7,9(11)-dien-3alpha,15alpha-diol-3alpha-D-glucofuranoside (3) and 1-phenyl-2-hydroxy-3,7-dimethyl-11-aldehydic-tetradecane-2-beta-D-glucopyranoside (4), along with several known compounds were isolated from the methanol extract of hulls of Oryza sativa. The new structures were established by one- and two-dimensional NMR and in combination with IR, EI/MS, FAB/MS and HR-FAB/ MS. Compound (3) strongly inhibited the growth of duckweed (Lemna paucicostata Hegelm 381), whilst compounds (2) and (4) exhibited weak inhibition.     

小茴香根的化学成分研究

从小茴香(Foeniculum vulgare Mill.)根的乙醇提取物中分离得到了5个化合物,通过MS和NMR等方法鉴定为:莳萝脑(1),亚油酸蔗糖苷(2),镰叶芹二醇(3),β-谷甾醇(4),豆甾醇-β-D-吡喃葡萄糖苷(5),其中化合物2和3首次从该种植物中分离得到。     

Chemistry and weak antimicrobial activities of phomopsins produced by mangrove endophytic fungus Phomopsis sp. ZSU-H76

Three metabolites named phomopsin A (1), B (2) and C (3), together with two known compounds cytosporone B (4) and C (5), were isolated from the mangrove endophytic fungus, Phomopsis sp. ZSU-H76 obtained from the South China Sea. Their structures were elucidated by spectroscopic methods, mainly by 1D and 2D NMR spectroscopic techniques. The medium-sized cyclic phenol ether based on 1 or 2 is rare in natural products. In bioassays, compounds 1, 2, and 3 had no significant antibiotic activities, but compounds 4 and 5 inhibited two fungi Candida albicans and Fusarium oxysporum with an MIC ranging from 32 to 64 microg/ml.     

鞭檐犁头尖中的苯丙素甙类化合物

从天南星科植物鞭檐犁头尖的根茎中分离得到3个化合物,运用波谱技术(UV,IR,^1HNMR,^13C NMR and 2D NMR)对它们的化学结构进行解析,分别鉴定为松柏甙(1),甲基松柏甙(2)和硝酸钾(3)。从鞭檐犁头尖中分离得到苯丙素甙类化合物尚属首次。     

Synthesis, antimicrobial activity and cytotoxicity of novel oxadiazole derivatives

In the present study, 5-substituted-1,3,4-oxadiazolin-2-thiones (1a-b) were synthesized via the ring closure reactions of appropriate acid hydrazides with carbon disulphide. N-(Benzothiazol-2-yl)-2-[[5-substituted-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide derivatives (3a-j) were obtained by the nucleophilic substitution reactions of 5-substituted-1,3,4-oxadiazolin-2-thiones (1a-b) with N-(benzothiazol-2-yl)-2-chloroacetamides. The chemical structures of the compounds were elucidated by IR, (1)H NMR, (13)C NMR and FAB(+)-MS spectral data and elemental analyses. The synthesized compounds were screened for their antimicrobial activities against Micrococcus luteus, Bacillus subtilis, Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, Listeria monocytogenes and Candida albicans. All compounds except compound 3h exhibited the highest antibacterial activity against P. aeruginosa. Among all compounds (3a-j), the compounds bearing 4-methoxyphenoxymethyl moiety on oxadiazole ring (3a-e) exhibited the highest inhibitory activity against C. albicans. Although compound 3j did not possess 4-methoxyphenoxymethyl moiety on oxadiazole ring, this derivative also exhibited the same level of anti-candidal activity. The compounds were also investigated for their cytotoxic effects using MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Compound 3a exhibited the highest cytotoxic activity, whereas compound 3g possessed the lowest cytotoxic activity against NIH/3T3 cells.