A new flavonol glucoside from the aerial parts of Sida glutinosa

Phytochemical investigation on the dried aerial parts of Sida glutinosa has led to the isolation of a new flavonol glucoside, glutinoside (1), along with seven known compounds, 24(28)-dehydromakisterone A (2), 1,2,3,9-tetrahydropyrrolo[2,1-b]-quinazolin-3-amine (3), docosanoic acid, 1-triacontanol, campesterol, stigmasterol, and β-sitosterol. The structures of these compounds were elucidated by means of extensive spectroscopic techniques as well as GC/MS analysis (for sterols) and comparison with the literature data. All these seven known compounds are reported from this plant for the first time.     

Guaiacin A and B from the Leaves of Guaiacum officinale

Guaiacin A and B, two new saponins, have been isolated from the leaves of G. OFFICINALE and were characterised on the basis of (13)C-NMR and FAD mass spectroscopy as 3- O-(beta- D-glucopyranosyl (1-->3)-alpha- L-arabinopyranosyl]-30-nor-olean-12,20(29)-dien-28- O-beta- D-glucopyranosyl ester ( 1) and 3- O-[ D-glucopyranosyl-(1-->3)-alpha- L-arabinopyranosyl] oleanolic acid-28- O-beta- D-glucopyranosyl ester ( 2).     

A new flavonol glucoside from the aerial parts of Sida glutinosa

Phytochemical investigation on the dried aerial parts of Sida glutinosa has led to the isolation of a new flavonol glucoside, glutinoside (1), along with seven known compounds, 24(28)-dehydromakisterone A (2), 1,2,3,9-tetrahydropyrrolo[2,1-b]-quinazolin-3-amine (3), docosanoic acid, 1-triacontanol, campesterol, stigmasterol, and β-sitosterol. The structures of these compounds were elucidated by means of extensive spectroscopic techniques as well as GC/MS analysis (for sterols) and comparison with the literature data. All these seven known compounds are reported from this plant for the first time.     

A New Bidesmosidic Triterpenoidal Saponin from the Roots of Symphytum officinale

A new triterpenoidal saponin having hederagenin as the aglycone was isolated from the roots of SYMPHYTUM OFFICINALE L. The structure of this saponin was elucidated by FAB-MS, (1)H-, (13)C-NMR, 2D-NMR analyses and chemical studies as 3- O-[beta- D-glucopyranosyl-(1-->4)-alpha- L-arabinopyranosyl]-hederagenin 28- O-[beta- D-glucopyranosyl-(1-->6)-beta- D-glucopyranosyl] ester.     

New dammaranes, esterified with malonic acid, from leaves of Betula pendula

Three known and five new dammarane triterpenes, esterified with malonic acid at C-3 with hemolytic activity were identified from the ethanol-water extract of leaves of Betula pendula Roth: 12-O-acetyl-3alpha,12beta,20(S),24(R)-tetrahydroxydammar-25-en-3-yl hydrogen propanedioate, 12-O-acetyl-3alpha,12beta20(S),24(S)-tetrahydroxydammar-25-en-3-yl hydrogen propanedionate, 12-O-acetyl-3alpha,12beta,17alpha,20(S),24(R)-pentahydroxydammar-25-en-3-yl hydrogen propanedioate, [12beta-acetoxy-4,4,8,10,14-pentamethyl-17-(2-methyl-5-oxotetrahydrofuran2(S)-yl)-hexadecahydrocyclopenta[A]phenanthren-3alpha-yl] hydrogen propanedioate, 12- O-acetyl-3alpha,12beta,20(S),25-pentahydroxydammar-23(E)-en-3-yl hydrogen propanedioate, and one which was new for Betula pendula but found in other Betula species: 12-O-acetyl-20,24-epoxy-3alpha,12beta,20(S),24(R),25-pentahydroxydammar-3-yl hydrogen propanedioate. The structures were elucidated by MS, (1)H-NMR, (13)C-NMR, (1)H-(1)H-COSY, DEPT, (1)H-(13)C-NMR (HMQC, HMBC) experiments.     

小红参的化学成分研究

Six compounds were isolated from the ethyl ether extract of Rubia yunnanensis(Franch)Diels. Based on spectroscopic means(UV,IR,MS,¹H-NMR and ¹³C-NMR)five of themwere identified as rubiarbonol A,rubiarbonol G,rubiarbonone A,1,3,6-trihydroxy-2-methylanthr-aquinone β-sitosterol and one new compound identified as 7β,19α,28-trihydroxyarbor-9(11)-3-one,named rubiarbonone B.     

Cussonosides A and B, two Triterpene-saponins from Cussonia barteri.

Two major saponins have been isolated from the stem bark of CUSSONIA BARTERI Seem (Araliaceae). Structural elucidation employing mainly (1)H- and (13)C-NMR, FAB-MS and GC-MS spectroscopic methods revealed a new hederagenin 28- O-[alpha- L-rhamnopyranosyl (1 --> 4)-beta- D-glucopyranosyl (1 --> 6)]-beta- D-glucopyranosyl ester (Cussonoside A), and the corresponding oleanolic acid analogue (Cussonoside B). Cussonoside A exhibits a pronounced sedative effect.     

Ortho-Effekte in 1-(o-Aminomethylaryl)-(buten(1)-3-onen und ihren Hydrierungsprodukten, 3. Mitt. o-Aminomethyl-benzalacetone und ihre Hydrierungsprodukte,Teil 2

Ortho-effects in 1-(2-Aminomethylaryl)-1-buten-3-ones and Their Hydrogenation Products, III: 2-(Aminomethyl)phenylmethylenacetones and Their Hydrogenation Products, II The preparations of the phenylmethylenacetones and their (deuterated) hydrogenation products (compounds 2 – 28 ) are described; anomalies in some of the ¹³C-NMR spectra are explained by increment calculations.     

NMR-Spektroskopie an Heterocyclen, 5. Mitt. 13C-NMR- und massenspektrometrische Untersuchung N-substituierter Methoxy- und Hydroxy-äthylimidazole

NMR-Spectroscopy of Heterocyclic Compounds, V: ¹³C-NMR and Mass Spectrometry of N-Substituted (2-Methoxyethyl)- and (2-Hydroxyethyl)-imidazoles The ¹³C-NMR and mass spectra of various N-substituted (2-methoxyethyl)- and (2-hydroxyethyl)imidazoles are described. A scheme for the fragmentation of 1,2-diethyl-4-(2-hydroxyethyl)imidazole is reported.     

Constituents of the herb ofIsodon excisus var.coreanus

The studies were carried out to evaluate the constituents in the aerial part ofIsodon excisus var.coreanus (Labiatae). From the aqueous fraction of methanol extract, compound 1 (alpha-[[3-(3, 4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-benzenepropanoic acid), compound II (9-methyl-dihydroferulic acid-4-O-beta-D-glucopyranosyl (1-->2)-alpha-L- rhamnopyranosyl (1-->4)-beta-D-glucopyranoside), compound III (ent-7alpha, 11alpha, 15beta-trihydroxy-kaur-16-en-1-O-beta-D-glucopyranoside) and compound IV (2alpha, 3beta, 7alpha, 23-tetrahydroxy-olean-12-en-28-oic acid 28-O-beta-D-glucopyranoside) were isolated and identified on the basis of their physicochemical and spectroscopic evidences[IR, FAB(-)MS,(1)H-NMR,(13)C-NMR, HMQC,(1)H-(1)H COSY and HMBC (Heteronuclear Multiple Bond Connectivity)]. Especially, New compounds II and III were named isodonin A and Isodonin B respectively.     

一些天然产香豆素类化合物的13C核磁共振谱的研究

本文报道了四种基本骨架类型的十八种天然产香豆素(Ⅱ～ⅩⅨ)的¹³C NMR光谱数据。其中包括法落海素、长前胡素-甲、长前胡素-乙、长前胡素-丙等新香豆素化合物的¹³CNMR数据。对这些数据进行了研究,总结了一些取代效应的规律。这些光谱数据和规律对于这四类型天然产香豆素化合物的结构鉴定和¹³C信号的指定是有价值的。     

绞股蓝皂苷Ⅸ的核磁共振研究

从加拿大产西洋参茎叶中分离得到一个化合物 ,为绞股蓝皂苷Ⅸ .利用1H NMR ,13C NMR和 2DNMR(2D HOHAHA ,HMBC)等谱学方法明确了其结构 ,并对其1H和13C谱数据进行了明确归属 ,为与绞股蓝皂苷Ⅸ结构类同的皂苷类化合物的结构研究提供了可靠的谱学方法和数据 .     

喙果绞股蓝中皂甙成分的研究

首次从喙果绞股蓝(Gymostemma yixingense CY Wu et SK Chen)中分得四个皂甙成分(Ⅰ～Ⅳ),经理化常数测定、光谱解析和化学方法确定了它们的结构。其中Ⅰ为新化合物,命名为喙果皂甙A(yixinosideA),Ⅱ,Ⅲ和Ⅳ分别鉴定为绞股蓝皂甙XLIVXLII(gypensideXLIV,XLII)和具明显调脂作用的人参皂甙Rb₁(ginsenosideRb₁)。此外,Ⅰ经酸水解得到一新皂甙元1β-羟基人参二醇(1β-hydroxylpanaxadiol)(Ⅴ)和一新次级甙,命名为喙果皂甙B(yixinosideB,VI)。     

Metabolism of glycyrrhetic acid by rat liver microsomes-II. 22 alpha- and 24-hydroxylation

18 beta-Glycyrrhetic acid (GA, an aglycone of glycyrrhizin) is converted to 3-oxo-18 beta-glycyrrhetic acid (3-oxoGA) in the presence of NADP+ by rat liver homogenates, but GA was converted in the presence of NADPH to two other metabolites showing lower Rf values on thin-layer chromatography (TLC) than those of GA and 3-oxoGA by postmitochondrial supernatant of rat liver. The GA-metabolizing activity in the presence of NADPH was localized in microsomes, similar to localization of GA-oxidizing activity to 3-oxoGA. The GA-metabolizing activity required NADPH as a cofactor and O2 for full activity and was inhibited with CO, suggesting the hydroxylation reaction of GA by cytochrome P450. Two metabolites (I and II, lower and higher Rf values on TLC, respectively) were purified on preparative TLC. Mass spectral (MS) analyses of II and methyl ester of acetylated I indicated the formation of monohydroxylated metabolites. On the basis of 3H- and 13C-NMR assignments I and II were identified to be 22 alpha- and 24-hydroxy-18 beta-glycyrrhetic acids, respectively. 3-OxoGA and 3-epi-18 beta-glycyrrhetic acid (3-epiGA) seem to be also hydroxylated at C-22 and C-24. A metabolite of 3-oxoGA showing a lower Rf value was also identified as 22 alpha-hydroxy-3-oxo-18 beta-glycyrrhetic acid by MS and 3H- and 13C-NMR spectral analyses. In 22 alpha-hydroxylation the best substrate was 3-oxoGA, followed by GA and 3-epiGA. On the other hand, for 24-hydroxylation the best substrate was GA, then 3-oxoGA, and 3-epiGA in order. However, 18 alpha-glycyrrhetic acid (18 alpha-GA) was a poor substrate for both 22 alpha- and 24-hydroxylation.     

New Ecdysteroids from Serratula tinctoria

Six new ecdysteroids have been isolated from SERRATULA TINCTORIA; these are: the 2,22- and 3,22-diacetates of 20-hydroxyecdysone, 5beta-hydroxyrubrosterone, 3-epi-poststerone, 3-epi-rubrosterone, and 22-oxo-20-hydroxyecdysone. These minor compounds were found together with the known ecdysteroids, 20-hydroxyecdysone, its 2-, 3-, and 22-monoacetates, rubrosterone, poststerone, polypodine B (5beta,20-dihydroxyecdysone), pterosterone (25-deoxy-20,24-dihydroxyecdysone), and makisterone C (24-ethyl-20-hydroxyecdysone). All these ecdysteroids were isolated by a combination of several chromatographic techniques (liquid chromatography on alumina, DCCC, and HPLC), then identified using standard mass spectrometric and 2D (1)H-NMR techniques.     

仙茅的酚性甙成分研究

从仙茅科仙茅(Curculigo orchioides Gaerth.)根茎的水溶性部位中,分离得到一个新的酚性甙和两个新的含氯酚性甙。经光谱(UV,IR.¹HNMR,^{13CNMR和MRMS,FAB-MS)解析及化学方法,确定了它们的结构,并且分别命名为仙茅甙乙(Curculigoside B),仙茅素B和C(curculigine B和C)。}     

A beta-Hydroxychalcone from Leptospermum scoparium

A beta-hydroxychalcone 1, so far not reported as a natural compound, was separated from the diethyl ether extract of LEPTOSPERMUM SCOPARIUM (Myrtaceae). Furthermore, three known flavonoids 2-4 were isolated. The (13)C-NMR spectra of 2-4 are reported, since they have as yet not been reported in the literature.     

甘草酸二铵18位差向异构体的核磁共振研究

目的对甘草酸二铵18位两种差向异构体的1HNMR、13CNMR谱信号进行全归属。方法应用COSY、TOCOSY、NOESY、HSQC、HMBC二维核磁共振技术,对甘草酸二铵两种异构体进行了测试。结果首次利用二维核磁共振技术对甘草酸二铵两种异构体的1HNMR、13CNMR谱信号进行了全归属。结论甘草酸二铵两种异构体的部分13CNMR谱数据差别较大,可作为区分两种异构体的一个指标。     

11Alpha,13-and 11beta,13-dihydro-4H-xanthalongin 4-O-beta-glucopyranosides: new sesquiterpene lactone glycosides from flowers of Arnica amplexicaulis and A. mollis

The flowers of A. amplexicaulis afforded, in addition to xanthalongin ( 1), 11beta,13-dihydroxanthalongin (2), its 11-epimer (3), and 11alpha,13-dihydro-4H-xanthalongin (4), the new xanthanolide glycosides 11alpha, 13-dihydro-4 H-xanthalongin 4- O-beta-D-glucopyranoside (5) and its 11-epimer (6). The glycosides were also isolated from the flowers of A. mollis. The structures were elucidated by NMR spectroscopy (1)H-NMR, COSY, (13)C-NMR, HETCOR, DEPT), MS (EI, FAB, FD), and enzymatic hydrolysis of the glycosides. The chemo-taxonomic importance is discussed.     

Three new iridoids from the roots of Valeriana jatamansi

Three new iridoids, valeriandoids D-F (1-3), have been isolated from the roots of Valeriana jatamansi. Structure elucidation, especially the positions of the acyloxy groups, and complete (1)H- and (13)C-NMR assignments of these new compounds were carried out using one- and two-dimensional NMR measurements, including (1)H- and (13)C-NMR, DEPT-135, (1)H-(1)H COSY, HMQC, HMBC, and HR-ESI-MS experiments.