Emodin, a protein tyrosine kinase inhibitor from Polygonum cuspidatum.

Bioassay-directed fractionation of a Chinese medicinal plant, Polygonum cuspidatum (Polygonaceae), has led to the discovery of an anthraquinone, emodin [1], as a strong inhibitor of a protein tyrosine kinase (p56lck) partially purified from bovine thymus. Comparison of the IC50 values of emodin for protein tyrosine kinase inhibitory activity with physcion [2] and emodin-O8-D-glucoside [3], also isolated from the same plant, reveal the importance of the hydroxyl groups at C-6 and C-8 for the observed activity.     

一种提高大黄饮片中结合型蒽醌的原药材炮制方法研究

[目的]建立一种提高大黄饮片中结合型蒽醌原药材的炮制方法。[方法]将大黄原药材置密闭蒸锅内,采用隔水蒸方式将大黄蒸透,进行切片,同时应用高效液相色谱(HPLC)法对饮片中蒽醌类成分进行测定比较。[结果]大黄炮制的饮片中总蒽醌含量与传统炮制的饮片基本一致,结合型蒽醌含量显著高于传统炮制饮片。[结论]提高大黄饮片中结合型蒽醌的原药材炮制方法生产周期短,节约成本,适宜大生产,可作为其炮制方法之一。     

Isolation of potential cancer chemopreventive agents from Eriodictyon californicum.

Activity-based fractionation of Eriodictyon californicum resulted in the isolation of 12 flavonoids that inhibit the metabolism of the carcinogen benzo[a]pyrene by hamster embryo cells in tissue culture. One was identified as a new flavanone, 3'-methyl-4'-isobutyryleriodictoyol [1], on the basis of spectroscopic analysis and alkaline hydrolysis. The seven other active flavanones were identified as eriodictyol [2], homoeriodictyol [3], 5,4'-dihydroxy-6,7-dimethoxyflavanone [4], pinocembrin [5], sakuranetin [6], 5,7,4'-trihydroxy-6,3'-dimethoxyflavanone [7], and naringenin 4'-methyl ether [8]. Four active flavones were also isolated: cirsimaritin [9], chrysoeriol [10], hispidulin [11], and chrysin [12]. The high inhibition of benzo[a]pyrene metabolism and the activation of benzo[a]pyrene to ultimate carcinogenic DNA-binding metabolites by cirsimaritin and chrysoeriol at a concentration of only 10 micrograms/ml indicates that these flavones warrant further investigation in vivo as potential chemopreventive agents.     

大黄蒽醌致泻作用及其机理的初步研究

目的比较大黄结合蒽醌、游离蒽醌致泻作用的强度并探讨其相关机制。方法通过灌服高浓度的奶粉溶液以营造高营养性环境,在此基础上考察了大黄结合蒽醌及游离蒽醌对小鼠的致泻作用;并运用析因设计分析了奶粉在这些致泻作用中的作用,同时还考察了大黄结合蒽醌及其游离蒽醌体外对胃蛋白酶活性的影响。结果大黄游离蒽醌500,1000mg/kg均可使小鼠胃内容物和小肠内容物显著增加;大黄结合蒽醌500,1000 mg/kg也可显著增加小鼠小肠内容的重量,但对小鼠胃内容重量的影响作用较弱;各药物组均可显著增加小鼠各肠段内的蛋白质浓度。析因设计的实验结果显示,无论是大黄游离蒽醌或是结合蒽醌均可显著增加正常小鼠(未加用奶粉)的胃、小肠及全胃肠道的内容物及蛋白质的含量,并可显著降低小鼠小肠、结肠Cl-浓度和升高小鼠结肠K 浓度;奶粉本身也具有与大黄蒽醌类似的作用,与之合用可增强大黄蒽醌的作用。体外实验结果显示,无论是大黄游离蒽醌或是结合型蒽醌对胃蛋白酶的活性均无明显影响。结论大黄游离蒽醌和结合蒽醌均具有显著的致泻作用;其机理可能是通过刺激胃肠道分泌、增加胃肠道内蛋白质浓度而产生容积性导泻。     

Novel secoiridoid lactones from Jasminum multiflorum

Four new secoiridoid lactones, jasmolactones A [1], B [2], C [3], and D [4], were isolated from the aerial part of Jasminum multiflorum. The structures of these compounds, which contain a novel bicyclic 2-oxo-oxepano[4,5-c]pyran ring system, were established by spectral analyses and chemical correlations. Pharmacological testing revealed that jasmolactones B and D possess coronary vasodilating and cardiotropic activities.     

Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography

Ten 12-membered macrocyclic pyrrolizidine alkaloids, all of them esters of the necines, retronecine or otonecine, have been isolated from Senecio anonymus. The separation, carried out by droplet counter-current chromatography, afforded senecionine [1], integerrimine [2], retrorsine [3], senkirkine [5], neosenkirkine [6], otosenine [10], hydroxysenkirkine [7], and a new alkaloid given the trivial name anonamine [9]. Traces of usaramine [4] and another new alkaloid, hydroxyneosenkirkine [8], were detected by 1H nmr. In addition, the previously unreported 3a beta-hydroxy-4-ethoxy-2,6-perhydroindoledione [11] was isolated. X-ray structures were obtained for neosenkirkine [6], hydroxysenkirkine [7], anonamine [9], and [11]. 1H-13C heteronuclear shift correlated nmr (HETCOR) provided unambiguous chemical shift assignments for 13C-nmr data. Antitumor activity was assayed using the A204-rhabdomyosarcoma cell line in soft agarose.     

Additional bioactive heptenes from Melodorum fruticosum

Four additional new bioactive heptenes, melodorinol [2], homomelodienone [4], 7-hydroxy-6-hydromelodienone [5], and homoisomelodienone [7] have been isolated from Melodorum fruticosum. These compounds were slightly to significantly cytotoxic to human tumor cell lines. Their structures have been determined by comparison of their 1H-nmr, 13C-nmr, and mass spectral data with those of prototype compounds (acetylmelodorinol [1], melodienone 3, and isomelodienone [6]).     

Sesquiterpene furans and thiosesquiterpenes from the nudibranch Ceratosoma brevicaudatum

Six furanosesquiterpenes have been isolated from an Australian nudibranch, Ceratosoma brevicaudatum, and their structures were determined by spectral analysis. The metabolites include the known terpenes dehydrodendrolasin [1], dehydrolasiosperman [3], and thiofurodysinin acetate [7]. The remaining metabolites were determined to be an unreported cis isomer 2 of dehydrodendrolasin, (methylthio) furodysinin [4], and dithiofurodysinin disulfide [5], derivatives of thiofurodysinin acetate that had been isolated earlier from a sponge. 13C-nmr data were obtained for all compounds.     

煎煮时间对决明子中蒽醌类浸出量影响的研究

目的：研究煎煮时间对决明子中蒽醌类浸出量的影响。方法：用分光光度法测定不同煎煮时间的决明子（分整粒和１２目粗粉两种）煎液中蒽醌类的含量。结果：决明子煎液的吸收度煎煮时间曲线分为非线性快速浸出区、线性低速浸出区及浸出停滞区;将决明子适当粉碎有利于蒽醌类浸出。结论：决明子中蒽醌类煎出最佳时间应为非线性快速浸出区的终了时间,且第２煎不可弃之。     

Inhibition of angiotensin-I-converting enzyme by tetrahydroxyxanthones isolated from Tripterospermum lanceolatum.

Five tetrahydroxyxanthones, 3,4,6,7-tetrahydroxyxanthone [1], 1,3,5,6-tetrahydroxyxanthone [2], 3,4,5,6-tetrahydroxyxanthone [3], 1,3,6,7-tetrahydroxyxanthone [4], and 2,3,6,7-tetrahydroxyxanthone [5] isolated from Tripterospermum lanceolatum inhibited angiotensin-I-converting-enzyme activity in a dose-dependent manner. The mode of inhibition of the tetrahydroxyxanthones (THXs) was found to be competitive inhibition. When the tetrahydroxy groups of THXs were blocked with acetyl groups, the angiotensin-I-converting-enzyme inhibitory activity was abolished, suggesting that the tetrahydroxy groups are indispensible for the inhibitory activity.     

大黄中蒽醌衍生物的构效关系

从构效关系角度对大黄中存在的天然蒽醌衍生物进行综述。该类蒽醌衍生物具有相同的母核，因此体现出一些相同的药理活性，但因取代基的不同而表现出活性强度的不同。这些蒽醌衍生物在抗氧化，抗菌，抗癌，对免疫功能的影响等方面存在明显的构效关系，表现为活性的强度与取代基的氧化程度。     

煎煮时间对决明子中蒽醌类浸出量影响的研究

目的：研究煎煮时间对决明子中蒽醌类浸出量的影响。方法：用分光光度法测定不同煎煮时间的决明子（分整粒和１２目粗粉两种）煎液中蒽醌类的含量。结果：决明子煎液的吸收度煎煮时间曲线分为非线性快速浸出区、线性低速浸出区及浸出停滞区;将决明子适当粉碎有利于蒽醌类浸出。结论：决明子中蒽醌类煎出最佳时间应为非线性快速浸出区的终了时间,且第２煎不可弃之     

New ketodienes from the integumental lipids of the Guam brown tree snake, Boiga irregularis

A mixture of six new long chain ketodienes, (6Z,26Z)-pentatriacontadien-2-one [1], (8Z,26Z)-pentatriacontadien-2-one [2], (6Z,27Z)-hexatriacontadien-2-one [3], (8Z,27Z)-hexatriacontadien-2-one [4], (6Z,28Z)-heptatriacontadien-2-one [5], and (8Z,28Z)-heptatriacontadien-2-one [6], has been separated from the cuticular lipids of the Guam brown tree snake Boiga irregularis. Their structures were determined by chemical and spectral means.     

泻心汤有效组分及其配伍配比对大鼠腹腔巨噬细胞释放一氧化氮的影响

目的:观察泻心汤有效组分对巨噬细胞释放NO的影响,并对有效组分进行最佳配伍配比研究。方法:采用MTT法观察有效组分对巨噬细胞生长的影响,采用G riess法观察有效组分及其配伍配比对LPS诱导巨噬细胞产生NO的影响。结果:各组分在0.01~0.1 mg/ml剂量能明显抑制NO分泌,在LPS刺激细胞前1 h加入有效组分对NO的抑制作用弱于同时加药和LPS刺激后1 h加药;有效组分配伍后对NO分泌的抑制作用增强。结论:有效组分及其配伍配比均能抑制LPS诱导的巨噬细胞释放NO,且有效组分配伍后具有协同增效的特点。     

New hydroxylated benzo[c]phenanthridine alkaloids from Eschscholtzia californica cell suspension cultures

From cell cultures of Eschscholtzia californica and their spent medium, three new benzo[c]phenanthridine alkaloids--namely 10-hydroxysanguinarine [2a], 12-hydroxychelirubine [4a], and 10-hydroxychelerythrine [7a]--and two new dihydrobenzo[c]phenanthridine alkaloids--10-hydroxydihydrosanguinarine [2b] and 12-hydroxydihydrochelirubine [4b]--together with the known constituents sanguinarine [1a], chelirubine [3a], macarpine [5a], dihydrosanguinarine [1b], dihydrochelirubine [3b], and dihydromacarpine [5b], were isolated and characterized. Structure elucidations were done by 1H nmr, decoupling experiments, and NOESY spectra. Isolated microsomes from E. californica, the site of hydroxylation activity within the cells, contained the whole set 1b to 8b of 5,6-dihydrobenzo[c]phenanthridines. A scheme for the biosynthesis of macarpine [5a] from protopine [9] via dihydrosanguinarine [1b] is presented.     

Pyrrolizidine alkaloids from Heliotropium rotundifolium

Heliotropium rotundifolium was shown to contain, in addition to the previously isolated europine [1], three other alkaloids: heliotrine [2], lasiocarpine [3], and a new alkaloid identified as 5'-acetyleuropine [4]. The alkaloids were isolated by dccc and the structures established by spectroscopic means (1H and 1H- 13CHETCOR nmr and ms), physical properties (melting points and/or optical rotations), comparison with authentic samples, or by semi-synthesis.     

Minor sesquiterpenes from Maytenus chubutensis

Four new minor dihydro-beta-agarofuran-skeleton sesquiterpenes, 9 beta-benzoyloxy-1 alpha,2 alpha,6 beta-triacetoxy-15-hydroxydihydro-beta- agarofuran [1], 9 beta-benzoyloxy-1 alpha,2 alpha,6 beta,15-tetracetoxydihydro-beta-agarofuran [6], 9 alpha-benzoyloxy-1 alpha,2 alpha,6 beta-triacetoxy- 8 alpha,15-dihydroxydihydro-beta-agarofuran [7], and 9 alpha-benzoyloxy-1 alpha,2 alpha,6 beta,8 alpha-tetracetoxy-15- hydroxydihydro-beta-agarofuran [8] were isolated from the aerial parts of Maytenus chubutensis and identified by spectroscopy and chemical reactions.     

Isolation and structure of cytostatic steroidal saponins from the African medicinal plant Balanites aegyptica.

Bioactivity-guided separation of a CH2Cl2/MeOH extract of Balanites aegyptica afforded four new cytostatic saponins, named balanitins 4 [1], 5 [2], 6 [3], and 7 [4]. On the basis of enzymatic hydrolyses and glycosidation nmr chemical shifts employing the peracetates, structures 1-4 were established as yamogenin 3 beta-O-beta-D-glucopyranosyl-(1----3)-beta-D-glucopyranosyl-(1----4)-[al pha- L-rhamnopyranosyl-(1----2)]-beta-D-glucopyranoside [1], yamogenin 3 beta-O-alpha-L-rhamnopyranosyl-(1----3)-beta-D-glucopyranosyl-(1----4)- [alpha-L-rhamnopyranosyl-(1----2)]-beta-D-glucopyranoside [2], yamogenin 3 beta-O-beta-D-glucopyranosyl-(1----4)-[alpha-L- rhamnopyranosyl-(1----2)]-beta-D-glucopyranoside [3], and diosgenin 3 beta-O-beta-D-xylopyranosyl-(1----3)-beta-D-glucopyranosyl-(1----4)-[alp ha- L-rhamnopyranosyl-(1----2)]-beta-D-glucopyranoside [4].     

Further bioactive acetylenic compounds from the Caribbean sponge Cribrochalina vasculum.

In addition to the known 3-hydroxydocosa-(4E, 15E)-dien-1-yne [1], 3-hydroxy-16-methyleicos-(4E)-en-1-yne [2], and 3-hydroxy-19-methyleicos-(4E)-en-1-yne [3], the lipophilic extract of the Caribbean sponge Cribrochalina vasculum was shown to contain four new bioactive acetylene metabolites, (3R)-hydroxy-14-methyldocos-(4E)-en-1-yne [4], (3R)-hydroxy-16-methyleicos-1-yne [7], (3R)-hydroxy-19-methyleicos-1-yne [8], and docosa-(3E, 15Z)-dien-1-yne [9], whose structures were elucidated on the basis of chemical and spectral studies. The previously unassigned chirality at C-3 of the known compounds 1-3 has been also established as R.