Three polyoxygenated cyclohexenes from Uvaria calamistrata

Three new polyoxygenated cyclohexenes, named uvacanols F, G, H (1–3), were isolated from the roots of Uvaria calamistrata (Annonaceae). Their structures were determined to be 2-acetoxyl-5-chlorine-benzoyloxymethylcyclohex-1 (6)-ene-4-ol-3-benzoate (1), benzoyloxy-methylcyclohex-1 (6)-ene-2,3,4-triols-5-benzoate (2), 3-acetoxyl-benzoyloxymethylcyclohex-1 (6)-ene-4,5-diols-2-benzoate (3) by spectroscopic methods and chemical derivatization.     

Two new polyoxygenated cyclohexenes from Uvaria kweichowensis

Two new polyoxygenated cyclohexenes, kweichowenols C and D, were isolated from the leaves of Uvaria kweichowensis, and their structures were established on the basis of their spectral data. The two new compounds showed some antitumor activity by the MTT assay.     

光叶紫玉盘多氧取代环己烯类成分研究

从番荔枝科紫玉盘属植物光叶紫玉盘(Uvaria boniana Finet)地上茎EtOH提取物中分离出7种新的多氧取代环己烯类化合物,用波谱分析和Mosher酯制备等方法确定了全部化学结构及其绝对构型,分别命名为光叶紫玉盘醇A～G(uvaribonolA～G,1～7)。体外抗肿瘤筛选表明,这些天然化合物均无活性,但部分半合成衍生物活性明显,其中尤以光叶紫玉盘醇B(2)的氧化物(2a)最为显著,抑制KB、Bel₇₄₀₂和A₂₇₈₀细胞的IC50值均小于1μg·ml^-1,抑制HCT-8的IC₅₀则小于0.1μg·ml^-1。     

New polyoxygenated cyclohexene and polyoxygenated seco-cyclohexene from Uvaria boniana

A new polyoxygenated cyclohexene bonianol A (1) and another new polyoxygenated seco-cyclohexene bonianol B (2) were isolated from the leaves of Uvaria boniana, and their structures were established on the basis of spectroscopic methods including IR, HR-ESI-MS, 1D, and 2D NMR.     

Uvamalols D-G: novel polyoxygenated seco-cyclohexenes from the roots of Uvaria macrophylla

Uvamalols D-F (1 - 4), novel polyoxygenated seco-cyclohexenes, were isolated from the roots of Uvaria macrophylla, and their structures were elucidated by interpretation of spectral data.     

Four new compounds from the roots of Uvaria macrophylla

Four new compounds, uvamalols A–C (1–3) and uvarimacrophin A (4), have been isolated from the roots of Uvaria macrophylla. Their structures have been elucidated by spectroscopic methods. The relative configurations of uvamalols A–C have been established by NOE experiments, and the relative stereochemistry of uvarimacrophin A inferred from the diagnostic NMR data by comparison with known model compounds.     

Four new compounds from the roots of Uvaria macrophylla

Four new compounds, uvamalols A-C (1-3) and uvarimacrophin A (4), have been isolated from the roots of Uvaria macrophylla. Their structures have been elucidated by spectroscopic methods. The relative configurations of uvamalols A-C have been established by NOE experiments, and the relative stereochemistry of uvarimacrophin A inferred from the diagnostic NMR data by comparison with known model compounds.     

大花紫玉盘中的多氧取代环己烯衍生物

从大花紫玉盘茎中分离得到5个新的多氧取代环己烯衍生物,根据光谱分析及与已知化合物比较确定了它们的结构,并分别命名为大花紫玉盘酮A（2）、B（3）、C（5）、D（7）及大花紫玉盘醇J（5）。同时,应用CD谱测定了化合物2、5、6、7的绝对构型。     

A new cerebroside from Uvaria tonkinensis var. subglabra

A new cerebroside, subglain A (1), together with five known compounds (2–6) have been isolated from the stems of Uvaria tonkinensis var. subglabra. The structure of 1 has been determined to be 1-O-β-D-glucopyranosyl-(2S,3S,4R,8Z,2′R)-2-[N-(2′-hydroxytetracosanyl)-N-(1″,2″-dihydroxyethyl)-amide]-8-tetradecene-1,3,4-triol by spectroscopic evidence. The known compounds were identified as schisandriside (2), erythritol (3), β-D-glucopyranose (4), kaempferol-3,7-O-α-L-dirhamnoside (5), and (+)-lyoniresinol (6).     

瘤果紫玉盘叶中的黄酮类成分

目的研究瘤果紫玉盘(Uvaria kweichowensis)的化学成分,为阐明其活性成分,开发其资源提供科学依据。方法应用多种色谱技术进行分离纯化,根据理化性质和波谱技术进行结构鉴定。结果从瘤果紫玉盘叶中分离得到7个黄酮类化合物,分别鉴定为槲皮素(Ⅰ)、山奈酚(Ⅱ)、大豆苷元(Ⅲ)、黄芩苷(Ⅳ)、山奈酚3O芸香糖苷(Ⅴ)、芦丁(Ⅵ)、山奈酚3OβD吡喃葡萄糖苷(Ⅶ)。结论化合物Ⅰ~Ⅶ均为首次从紫玉盘属植物中分离得到。     

Antihepatotoxic and Trypanocidal Effects of the Root Bark Extract of Uvaria chamae

Antihepatotoxic and trypanocidal activities of a root bark extract derived from Uvaria chamae were tested in vivo and in vitro. The plant material was defatted with n -hexane and extracted with 70% ethanol. The ethanol extract was recovered in a 6.13% w/w yield. The LD 50 of the ethanol extract in mice at 24 hr was 166 mg/kg (i.p.). Intraperitoneal injection of the ethanol extract into mice showed no significant effect on pentobarbitone-induced hypnosis. Pentobarbitone-induced sleep in CCl 4 -poisoned rats was significantly reduced (p<0.005) by oral administration of the extract (60 mg/kg). The elevation of serum GOT, GPT, alkaline phosphatase and urea induced by CCl 4 intoxication in rats was also significantly reduced (p<0.005) by the ethanol extract. Uvaria chamae ethanol extract showed a significant (p<0.005) trypanocidal effect which was comparable to that of diminazine aceturate (r= 0.89). Reduction of existing parasitaemia in mice experimentally infected with Trypanasoma brucei brucei was dose-dependent.     

大花紫玉盘中新多氧取代环己烯类的结构鉴定

从番荔枝科紫玉盘属植物大花紫玉盘( Uvaria grandiflora Roxb.)根茎中分得4种新的多氧取代环己烯及已知化合物zeylenol,应用波谱分析、X-射线衍射、园二色谱和 Mosher 酯制备等手段确定了全部新化合物的结构及其绝对构型,分别命名为大花紫玉盘醇A(1),B(2),E(3)和F(4)。     

In Vitro Antibacterial and Antifungal Activities of Extracts and Compounds from Uvaria scheffleri

Petroleum ether, dichloromethane, and ethanolic extracts of the stem bark and leaves of Uvaria scheffleri Diels (Annonaceae) exhibited antifungal activity against Aspergillus niger (wild strain), Aspergillus fumigatus (wild strain), and a Penicillium species (wild strain). The ethanol extract of the stem bark was also active against Candida albicans (Strain H6392). The dichloromethane extract of the leaves showed the highest antifungal activity and in addition it showed antibacterial activity against Staphylococcus aureus (NCTC 6571). Fractionation of the dichloromethane extract of the leaves yielded nine known compounds. They included a 1 : 1 mixture of stigmasterol (1) and β-sitosterol (2), which showed antifungal activity against Candida albicans. Others were 3-farnesylindole (3), 2′,6′-dihydroxy-3′,4′-dimethoxy-chalcone (4), 2′-hydroxy-3′,4′,6′-trimethoxychalcone (5), 5-hydroxy-7,8-dimethoxyflavanone (6), 5,7,8-trimethoxyflavanone (7), and a 3 : 2 mixture of 2′,6′-dihydroxy-4′-methoxychalcone (8) and 5,7-dihydroxyflavone (9). Compound 7 and the mixture of compounds 8 and 9 showed antibacterial activity against Escherichia coli (NCTC 10418, MIC 125 µg/ml) and Staphylococcus aureus (MIC 125 µg/ml), respectively. The mixture of compounds 8 and 9 was also active against Candida albicans (MIC 31.25 µg/ml), Aspergillus niger, Aspergillus fumigatus, and the Penicillium species (MIC 1000 µg/ml). We conclude that Uvaria scheffleri extracts contain compounds with antifungal and antibacterial activity. The activities observed in this study are weak. Based on previous studies, it is being speculated that, possibly, the most active compounds were lost during fractionation. Further work to isolate more antifungal and antibacterial compounds is suggested.     

New polyoxygenated steroids from the South China Sea gorgonian Echinogorgia aurantiaca

Three new polyoxygenated steroids, named 3beta,7alpha,9alpha-trihydroxy-cholestan-6-one (1), 3beta,5alpha,6beta-trihydroxycholestan-1-one (2) and cholestane-3beta,5alpha,6beta,11beta-tetrol (3), along with four known steroids (4-7) were isolated from the South China Sea gorgonian Echinogorgia aurantiaca. The structures of 1-3 were established by extensive spectroscopic analysis, including 1D and 2D NMR data.     

Assessment of the cytotoxicity and genotoxicity properties of Uvaria chamae P. Beauv (Annonaceae) and Morinda lucida Benth (Rubiaceae) in mice

The toxicity profile of medicinal plants is an important preclinical requirement in the development of phytomedicines. The cytotoxic and genotoxic effects of the leaf of Uvaria chamae P. Beauv (Annonaceae) and stem bark of Morinda lucida Benth (Rubiaceae) were investigated in order to provide information on their safety as antimalarial plants. The methanol extract of U. chamae and ethanol (70%) extract of M. lucida were separately orally administered (125, 250, and 750?mg/kg/day) to mice for 10 consecutive days. Cyclophosphamide (50?mg/kg, single dose) and distilled water were used as positive and negative controls, respectively. The mice were injected with colchicine (0.04%) intra-peritoneally 24?h after the last administration of the extracts and the bone marrows harvested. Giemsa-stained slides of bone marrow cells were microscopically assessed for dividing cells to determine the mitotic index (MI) and scored for chromosomal aberrations (CA) according to standard methods. chamae exhibited dose-dependent cytotoxicity. At 750?mg/kg, the MI was significantly (p?M. lucida was not significantly different (p?>?0.05) from that of the negative control. The total CA observed from treatment with both plants at all doses were significantly (p?U. chamae showed both cytotoxicity and genotoxicity while M. lucida exerted only genotoxic effect. Nevertheless, the two plants should be used with caution in antimalarial therapy.     

Cytotoxic C-benzylated chalcone and other constituents ofEllipeiopsis cherrevensis

A new natural C-benzylated chalcone, 2',4'-dihydroxy-3'-(2-hydroxybenzyl)-6'-methoxychalcone (2), along with two other flavonoids, tiliroside and kaempferol 3-O-rutinoside, and an oxoaporphine alkaloid, lanuginosine were isolated from the aerial parts of Ellipeiopsis cherrevensis (Annonaceae). Two known polyoxygenated cyclohexene derivatives, ferrudiol and zeylenol, and a new analog, ellipeiopsol D, were also isolated. The chalcone 2 exhibited cytotoxic activity against human small-cell lung-cancer (NCI-H187), epidermoid carcinoma (KB) and breast cancer (BC) cell lines with IC50 values of 1.40, 5.31 and 13.92 microg/mL, respectively. This compound also showed antimalarial activity against Plasmodium falciparum with an IC50 value of 7.1 microg/mL as well as antimicrobacterial activity against Mycobacterium tuberculosis with a MIC of 25 mg/mL.     

瘤果紫玉盘中的酰胺类化学成分

瘤果紫玉盘(Uvaria kweichowensis)为番荔枝科紫玉盘属植物，在民间广泛应用于癌症、贫血和炎症的治疗，通过研究瘤果紫玉盘的化学成分，阐明其活性成分，为开发其资源提供科学依据。应用溶剂提取法，硅胶和Sephadex LH-20等多种色谱技术进行反复分离纯化，根据理化性质和现代波谱技术(EI-MS，¹H NMR，¹³C NMR)进行结构鉴定，从瘤果紫玉盘茎中分离得到6个酰胺类化合物，分别鉴定为紫玉盘双酰胺(1)，赛法酮(2)，马兜铃酸内酰胺A II(3)，因特洛卡内酰胺II(4)，马兜铃酸内酰胺A Ia(5)和4,5-dioxodehydroasimilobine (6)。其中化合物1为新化合物，2～6均为首次从该植物中分离得到。     

Essential oil from fruit of Xylopia langsdorffiana: antitumour activity and toxicity

Context: The genus Xylopia L. (Annonaceae) includes aromatic plants that have both nutritional and medicinal uses. Essential oils of Xylopia species have antitumour effects. However, the efficacy of the essential oil from the fruit of Xylopia langsdorffiana St. Hil & Tul. (EOX) has not been examined.

Objective: EOX was evaluated to determine its chemical composition, antitumour activity and toxicity.

Materials and methods: EOX was obtained from fresh fruits of X. langsdorffiana subjected to hydrodistillation, and gas chromatography-mass spectrometry was used to characterize the chemical composition of EOX. The toxicity of EOX was evaluated using haemolysis, acute toxicity and micronucleus assays. The in vitro antitumour activity of EOX was investigated using the sulforhodamine B assay. The sarcoma 180 murine tumour model was used to evaluate the in vivo antitumour activity and toxicity of EOX (50 and 100?mg/kg) after 7 d of treatment.

Results: The major components of EOX were α-pinene (34.57%) and limonene (31.75%). The HC₅₀ (concentration producing 50% haemolysis) was 293.6?μg/ml. EOX showed greater selectivity for the leukaemia cell line K562, with total growth inhibition (TGI) (concentration producing TGI) of 1.8?μg/ml, and for multidrug-resistant ovarian tumour cell line NCI/ADR-RES (TGI of 45.4?μg/ml). The LD₅₀ was approximately 351.09?mg/kg. At doses of 50 and 100?mg/kg, EOX inhibited the in vivo growth of sarcoma 180 by 38.67 and 54.32%, respectively. EOX displayed minor hepatic alterations characteristic of acute hepatitis and induced no genotoxicity.

Conclusion: EOX showed in vitro and in vivo antitumour activity and low toxicity, which warrants further pharmacological studies.     

Two new sesquiterpenes from the fruits of Fissistigma villosissimum

Two new sesquiterpenes, namely fissistinone (1) and fissistinol (2), along with ten known compounds (3–12), were isolated from the fruits of Fissistigma villosissimum. Their structures were elucidated on the basis of spectral data analysis, including one-dimensional (1D), two-dimensional (2D)-nuclear magnetic resonance (NMR), and high-resolution–electrospray ionization–mass spectrometry (HR–ESI–MS). Compounds 1–8 were evaluated for their cytotoxic activities against KB cell line; however, all these compounds did not show cytotoxic activity.     

Anti-tumour clerodane-type diterpenes from Mitrephora thorelii

Bioassay-guided fractionation of the crude extract of Mitrephora thorelii (Annonaceae) led to the isolation of two clerodane-type diterpenes. Their structures were characterised on the basis of spectroscopic methods as 6α,16,18-trihydroxycleroda-3(4),13(14)-dien-15,16-olide (1) and 16-hydroxycleroda-3(4),13(14)-dien-15,16-olide (2). Compound 1 is a new compound. Compounds 1 and 2 exhibited inhibitory activity against the proliferation of human hepatoma BEL-7402 cells in vitro. Compound 2 also showed an in vivo anti-tumour effect against the growth of hepatoma H22 in mice.