Further constituents from the bark of Tabebuia impetiginosa

Further study on the constituents from the bark of Tabebuia impetiginosa (Mart. ex DC) Standley afforded twelve compounds, consisting of four iridoid glycosides, one phenylethanoid glycoside, five phenolic glycosides, and one lignan glycoside, along with seven known compounds. The structures of these compounds were determined based on the interpretation of their NMR and MS measurements and by chemical evidence.     

Antimicrobial constituents from the stem bark of Feronia limonia.

The stem bark of Feronia limonia (Fam. Rutaceae) yielded (-)-(2S)-5,3'-dihydroxy-4'-methoxy-6",6"-dimethylchromeno-(7,8,2",3")-flavanone along with several known compounds including an alkaloid, five coumarins, a flavanone, a lignan, three sterols and a triterpene. The structures of these compounds were determined by spectroscopic methods, mainly 1D and 2D NMR. The antimicrobial screening of compounds by a microdilution technique resulted in MICs in the range 25-100 microg/ml. Other biological activities of the known compounds are also discussed.     

二球悬铃木树皮的化学成分

二球悬铃木树皮的化学成分王静蓉段金廒周荣汉唐敏玲（中国药科大学植化分类及中药资源学研究室,南京２１００３８）ＣｈｅｍｉｃａｌｃｏｎｓｔｉｔｕｅｎｔｓｆｒｏｍｂａｒｋｏｆＰｌａｔａｎｕｓａｃｅｒｉｆｏｌｉａＷｉｌｄ．ＷａｎｇＪｉｎｇＲｏｎｇ,Ｄｕａｎ...     

Chemical constituents from the roots of cultivated Ilex pubescens

Phytochemical study of butanol extract from the roots of cultivated Ilex pubescens Hook. et Arn. obtained nine ursane triterpenes (1–9), two oleanane triterpenes (10–11) and three phenylpropanoids (12–14). All of the compounds were determined on the basis of MS and NMR and comparison with literature. Among them, compounds 2 and 13 were isolated from I. pubescens for the first time, of which 13 was a new finding in the Aquifoliaceae family. Our present study exhibited the taxonomic relationships between I. pubescens and other species in genus Ilex and those between Aquifoliaceae and other families. Furthermore, the study suggested the cultivated I. pubescens may be as an alternative for those wild resource collected freshly from mountain.     

Nitric oxide inhibitory constituents from Siegesbeckia pubescens

Two new sesquiterpenoids (1 and 2) and a new ent-pimarane type diterpenoid (3), together with eighteen known compounds (4–21), were isolated from the whole plants of Siegesbeckia pubescens. The structures of the new compounds were determined on the basis of 1D-, 2D NMR and HRESIMS data. All compounds were evaluated for their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages. Of these, highly oxygenated germacrane type sesquiterpenoids (1–2 and 13–14) showed significant inhibitory effects with IC₅₀ values ranging from 3.9 to 16.8 μM.     

Chemical constituents from the stem bark of Clausena excavata Burm. f

Phytochemical study on the stem bark of Clausena excavata Burm. f. led to the isolation and identification of 11 compounds, including four prenylated coumarins (1–4), three carbazole alkaloids (5–7), a limonoid (8), a sterol (9), a depside (10) and a xanthone (11). The chemical structures of the compounds were elucidated based on NMR and mass spectroscopic data, and further supported by comparison with previously literature values. This is the first report on the isolation of compounds 10 and 11 from the genus Clausena. The chemotaxonomic significance of the isolated compounds is discussed.     

Chemical constituents from the stem bark of Acer tegmentosum

A new phenolic glycoside, 4-hydroxyphenylethyl-1-O-β-D-[6′-O-(4-hydroxybenzoyl)]-glucopyranoside (1) was isolated from the stem bark of Acer tegmentosum, along with seven known phenolic compounds (2–8). The structure of compound 1 was determined by spectral analyses, including HR-ESI-MS, 1D and 2D NMR (COSY, HMQC and HMBC) experiments. Compounds 3 and 4 were found in the family Aceraceae for the first time.     

Further constituents from Caralluma negevensis

Two new megastigmane glycosides (1 and 2) and two new flavone glycosides (3 and 4) were isolated from the methanol extract of the whole plant of Caralluma negevensis Zohary (Asclepiadaceae). The structures of the isolated compounds were characterized as (9R)-2beta,9-dihydroxymegastigma-4,7-dien-3-one-9-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (1), 2beta,9-dihydroxymegastigma-4-en-3-one 9-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (2), luteolin 3'-O-beta-D-glucopyranoside-4'-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (3), and luteolin 3',4'-di-O-beta-D-glucopyranoside (4). The structures of the isolated compounds were established on the basis of spectral evidence and chemical transformation.     

Limonoids from the bark of Toona ciliata var pubescens and their anti-tumor activities

Two previously undescribed B-ring seco-limonoids named toonacilinatin I (1) and toonacilinatin J (2), together with ten known analogues (3–12), were isolated from the ethyl acetate extract of the bark of Toona ciliata var pubescens. All structures were elucidated by extensive spectroscopic analysis involving IR, MS, and NMR. Among them, compounds 1–10, and 12 were discovered from this plant for the first time. All the compounds except 7 and 8 were evaluated for their anti-tumor activity by MTT method of MDA-MB-231 and A-673 cell lines, the bioassay results showed that compounds 1, 2, 5, 9 and 11 exerted superior inhibitory activity with IC₅₀ values as 0.11–1.60 μM. Notably, those active compounds exhibited little effect on normal hepatocellular HL-7702 cells.     

Bioactive chemical constituents from the root bark of Morus australis

Two new pyranoflavonoids, morustralins A (1) and B (2), a new natural benzene derivative, one benzenoid (Z)-1-hydroxy-4-(2-nitroethenyl)benzene (3), and thirty known compounds were isolated and characterized from the root bark of Morus australis. The structures of the new compounds were established from spectroscopic and spectrometric analyses. Ten isolates (1–10) were examined for inhibitory effects on adenosine diphosphate (ADP)-, arachidonic acid (AA)-, and platelet-aggregating factor (PAF)-induced platelet aggregation. Among the tested compounds, compound 3 displayed the most significant inhibition of ADP- and AA-induced platelet aggregation with IC₅₀ values of 9.76 ± 5.54 and 9.81 ± 2.7 μM, respectively. In addition, eight purified compounds (3–10) were examined for inhibition of nitric oxide (NO) production in RAW 264.7 cells and six compounds (3–8) displayed significant inhibitory effects with IC₅₀ values ranging from 2.1 ± 0.3 to 6.3 ± 0.6 μM.     

Anti-hepatitis B virus constituents from the stem bark of Streblus asper

Seven compounds, (7′S,8′S)-trans-streblusol A, (7′R,8′S)-erythro-streblusol B, (7′S,8′S)-threo-streblusol B, 8′R-streblusol C, streblusquinone, (8R,8′R)-streblusol D, and streblusol E, along with 15 known compounds (8–22) were isolated from the n-butanol-soluble part of the MeOH extract of stem bark of Streblus asper. Their structures were elucidated through application of extensive spectroscopic methods, including ESI-MS and 2D NMR spectroscopy (HMQC and HMBC). The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans and allylbenzene derivatives were evaluated for their anti-HBV activities in vitro using the HBV transfected Hep G2.2.15 cell line. The most active compounds, magnolol and 9-β-xylopyranosyl-isolariciresinol, exhibited significant anti-HBV activities with IC₅₀ values of 2.03 and 6.58 μM for secretion of HBsAg, with no cytotoxicity, and of 3.76 and 24.86 μM for secretion of HBeAg, with no cytotoxicity.     

Antiplasmodial constituents from the stem bark of Polyalthia longifolia var pendula

Along with two known compounds (1 and 2), four new clerodane diterpenes were isolated and identified from the stem bark of Polyalthia longifolia: cleroda-3-ene pyrrole-15,16-dione (3), cleroda-3-ene, pyrrolidine-15,16-dione (4), cleroda-3,13(14)E-diene-15,16-diamide (5), and cleroda-3-ene-15,16-diamide (6). Their structures were elucidated by combinations of NMR, MS and IR. Using the WHO Mark III Microtest assay, the isolated compounds were evaluated for their antiplasmodial effects. They showed antiplasmodial effects, with IC₅₀s ranging from 4.5 to 213.8 μM.     

Chemical constituents from the bark of Annona salzmannii (Annonaceae)

1. Download : Download full-size image

Highlights? Bark of Annona salzmannii yielded sesquiterpenes, steroids, and isoquinoline alkaloids. ? Isoquinoline alkaloids are the chemotaxonomic marker of the genus Annona. ? The NMR data for reticuline (12) were revised. ? Selin-11-en-4α-ol (3) is reported for the first time in the genus Annona.     

水青树和昆栏树茎皮的化学成分

用化学和波谱分析方法从水青树（Ｔｅｔｒａｃｅｎｔｒｏｎ ｓｉｎｅｎｓｅ Ｏｌｉｖ．）茎皮中分离鉴定了５个化合物,分别为丁香甙（ｓｙｒｉｎｇａｎｉｄｅ）、儿茶素（ｃａｔｅｃｈｉｎ）、β－谷甾醇（β－ｓｉｔｏｓｔｅｒｏｌ）、胡萝卜甙（ｄａｕｃｏｓｔｅｒｏｌ）和白桦脂醇（ｂｅｔｕｌｉｎ）,均为从该种植物中首次分得。从昆栏树（Ｔｒｏｃｈｏｄｅｎｄｒｏｎ ａｒａｌｉｏｉｄｅ Ｓｉｅｂ．ｅｔＺｕｃｃ．）茎皮中     

Structural and stereochemical studies of five new pregnane steroids from the stem bark of Toona ciliata var. pubescens

Five new pregnane steroids, toonasterones A (1), B (2), (Z)-aglawone (3), (Z)-toonasterone C (4), and (E)-toonasterone C (5), were isolated from the stem bark of Toona ciliata var. pubescens. Their structures were elucidated by means of detailed spectroscopic (IR, MS, and 2D NMR) analysis, and the stereochemistry of 1 was secured by X-ray diffraction analysis. (Z)-aglawone (3) exhibited moderate inhibitory activity of protein tyrosine phosphatase 1B (PTP1B), a potential drug target for treatment of type-II diabetes and obesity, with an IC₅₀ value of 1.12 μg/mL.     

Antioxidant activity of pine bark constituents

A modified in vitro lipid peroxidation inhibition assay was used to guide the fractionation and the isolation of antioxidative principles of Fnnish pine bark extract. This approach yielded 3,4-dihydroxybenzoic acid (protocatechuic acid) and taxifolin-3-O-beta-glucopyranoside as major antioxidative compounds from the plant material. The structural elucidation of these compounds was undertaken with the help of HPLC-DAD and HPLC-ESI-MS analyses. Their IC50 values, in comparison to trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid), were: trolox (1.78 +/- 0.56 microM) < protocatechuic acid (5.77 +/- 1.63 microM) < taxifolin-3-O-beta-glucopyranoside (16.30 +/- 1.98 microM). The method for the determination of antioxidant activity proved reproducible and quick for routine analyses with 96 well plates.     

Chemical constituents from the bark of Juglans mandshurica Maxim. and their phenol oxidase inhibitory effects

Botanical insecticides investigation led to 21 compounds from the bark of Juglans mandshurica Maxim., in which, compounds 4, 10, 11, 13, 14 and 15 were isolated from Juglans genus for the first time. The inhibitory effect of dihydrokaempferol (6), naringenin (7) and rhoiptelol C (18) on phenol oxidase (PO) are 5–10 times more than arbutin, a well-known tyrosinase inhibitor. Thus, the selective and effective these inhibitors can be expected for using in the development of environment-friendly pesticide.     

Chemical constituents of the bark of Endlicheria oreocola (Lauraceae) from Colombia

1. Download : Download high-res image (467KB)
2. Download : Download full-size image