Benzyl benzoates and o-hydroxybenzyl flavanones from Uvaria ferruginea

The isolation of benzyl benzoates and o-hydroxybenzyl flavanones from Uvaria ferruginea, in addition to the previously reported cyclohexene oxides, provides evidence in support of the proposed biogenetic route to these compounds via the common benzyl benzoate precursor.     

Aromatic constituents from Uvaria chamae

A novel monobenzylated monoterpene, chamanen, has been isolated from the root bark of Uvaria chamae. In addition, the dimethyl ether of thymoquinol     

1-Epizeylenol from Uvaria zeylanica roots

1-Epizeylenol was isolated from Uvaria zeylanica roots and characterized, largely by ¹H and ¹³CNMR spectral comparisons with zeylenol.     

Dihydrochalcones from Uvaria angolensis

An investigation of the roots of Uvaria angolensis has led to the isolation and identification of two new dihydrochalcones, angoletin and uvangoletin, and the known C-benzyldihydrochalcones, uvaretin and isouvaretin. The structures were established from ¹³C NMR comparisons with known dihydrochalcones.     

Cyclohexene long-chain fatty acid esters from Uvaria dulcis (Dunal)

Two new cyclohexene long-chain fatty acid esters, namely Dulcisenes A and B, were isolated from the twigs of the Uvaria dulcis together with seven known compounds, uvarigranol E, (−)-zeylenol, ellipeiopsol B, 5,7-dihydroxyflavone, 8-hydroxy-5,7-dimethoxyflavanone, lupeol, and benzyl benzoate. The structures of the isolated compounds were elucidated by spectroscopic and mass-spectrometric analyses, including 1D, 2D NMR and HR TOF MS. Several of these metabolites were tested for cytotoxicity against HepG2, A549, S102, HuCCA-1, HeLa, MDA-MB-231, T47D, HL-60, and P388 cell lines.     

Aromatic esters from Solidago decurrens

From Solidago decurrens several new benzyl benzoates and two cinnamyl angelates were variously isolated from stems, flower and root.     

Polyoxygenated seco-cyclohexenes and other constituents from Uvaria valderramensis

Phytochemical study on the Philippine endemic Annonaceae plant Uvaria valderramensis afforded a new highly oxygenated seco-cyclohexene derivative, valderepoxide (1), along with the six known compounds uvamalols D (2) and G (3), grandiuvarone (4), 2′-hydroxy-3′,4′,6′-trimethoxychalcone (5), valderramenol B (6) and benzoic acid. The structure of 1 was determined through extensive spectroscopic analyses including 1D, 2D NMR and HRESIMS. Its relative stereochemistry was established using 2D-NOESY. This is the first report on the isolation of polyoxygenated compounds 1–3 and chalcone 5 from U. valderramensis.     

(+/-)-Schefflone: a trimeric monoterpenoid from the root bark of Uvaria scheffleri

The trimeric monoterpene and mildly mosquito larvicidal agent, (+/-)-schefflone, that is an apparent derivative of the antiparasitic aromatic monoterpene espintanol, was isolated from the antimalarial extracts of the root bark of Uvaria scheffleri, together with espintanol. Structural determination of (+/-)-schefflone was achieved from spectroscopic data and confirmed by single-crystal X-ray diffraction analysis. (+/-)-Schefflone can be considered a product of a non-enzymatic Diels-Alder-type cycloaddition reaction of the quinonemethide derivative of espintanol as the diene and dienophile.     

Polyoxygenated cyclohexenes from the Chinese tree,Uvaria purpurea

Four new polyoxygenated cyclohexenes, 2-O-acetyl-6-O-methylzeylenol (2), 2-O-benzoyl-3-O-debenzoylzeylenone (5), 3-O-debenzoylzeylenone (6) and 3-O-debenzoylgrandiflorone (8), were isolated from the leaves of Uvaria purpurea. 2-O-acetyl-6-O-benzoylzeylenol (3) was also isolated for the first time as a natural product. Compounds 5-7 each showed inhibitory activity against the root growth of Lactuca sativa. Their structures were established by spectroscopic and chemical methods.     

Four polyoxygenated cyclohexenes from the Chinese tree, Uvaria purpurea

Two novel polyoxygenated cyclohexenes, 6-methoxyzeylenol (3) and 2-acetoxyzeylenone (4), together with two known compounds, zeylenol (1) and zeylenone (2), were isolated from the heartwood of the Chinese tree, Uvaria purpurea. Zeylenol (1) and zeylenone (2) both showed inhibitory activity toward the root growth of Lactuca sativa. Their structures were established by spectroscopic and chemical methods.     

紫玉盘中的新内酰胺

从紫玉盘(UvariamicrocarpaChamp.exBenth.)的茎枝分离到7个生物碱,经光谱数据分析鉴定为紫玉盘内酰胺(uvarilactam,1)、马兜铃内酰胺AⅡ(2)、马兜铃内酰胺BⅠ(3)、马兜铃内酰胺BⅡ(4)、马兜铃内酰胺AⅠa(aristololactamAⅠa,5)、4,5_dioxodehydroasimilobine(6)和oxoanolobin(7)。1～5属于菲甲酸内酰胺类化合物,6～7是阿扑菲生物碱类,化合物3与4以混合物出现。其中1是新化合物,其余化合物均首次从该植物中分离得到     

L-酪氨酸苄酯的合成及其影响因素研究

以L-酪氨酸和苯甲醇为原料合成一种新型的L-酪氨酸衍生物——L-酪氨酸苄酯。首先用苯甲醇与氯化亚砜反应生成氯化亚硫酸酯,合成物再与L-酪氨酸发生酯化反应得到L-酪氨酸苄酯,其结构经质谱(MS)分析法确证。在此基础上研究了影响该合成工艺的主要因素,即原料配比、反应温度、反应时间、pH值。结果显示合成L-酪氨酸苄酯的较佳工艺条件为:物料摩尔比mol(SOCl2)∶mol(L-酪氨酸)=1.3∶1.0,室温下反应3h,120℃下反应2h,后处理溶液pH为7.5。本工艺适宜于工业化大规模生产。     

Utilization of methoxylated benzoates and formation of intermediates by Desulfotomaculum thermobenzoicum in the presence or absence of sulfate

Desulfotomaculum thermobenzoicum strain TSB (DSM 6193) was found to utilize some methoxylated benzoates as carbon and energy source with or without sulfate. 3- or 4-Methoxybenzoate, vanillate (4-hydroxy-3-methoxybenzoate), syringate (3,5-dimethoxy-4-hydroxybenzoate) and 3,4,5-trimethoxybenzoate were converted to corresponding hydroxybenzoates. However, neither 2-methoxybenzoate nor 2,6-dimethoxybenzoate was utilized. The organism grew acetogenically on each of the methoxylated benzoates in the absence of sulfate.3,4-Dihydroxy-5-methoxybenzoate was detected during conversion of syringate, and syringate and 3,4-dihydroxy-5-methoxybenzoate were detected during conversion of 3,4,5-trimethoxybenzoate as intermediates.These findings indicate that 4-methoxyl-group is most readily cleaved, whereas 2-methoxyl-group is not utilized by the organism.     

Paleoequatorial rain forest of western India during the EECO: evidence from Uvaria L. fossil and its geological distribution pattern

During the early Eocene, Rajasthan was positioned near the equator and had a warm and humid tropical climate dominated by tropical rainforests like the present-day equatorial forests of South India. Many of the plants retrieved as fossils from Rajasthan are growing there as refugee. This study further strengthens this view as it reports a new species of Uvaria L. from the early Eocene sediments of Bikaner (Rajasthan) showing its best resemblance with the extant U. zeylanica Deless. ex DC., which is presently growing in the evergreen forests of South India and Sri Lanka. The genus is thought to have originated in Africa, and the present finding gives an idea about its geologic distribution in Asia and Australasia via India relying on ‘stepping stone’ hypothesis during the Early Eocene Climatic Optimum (EECO) when climatic conditions were favourable for the luxuriant growth of tropical vegetation. A general cooling trend after EECO and change in the configuration of land and sea affected the climate on the regional scale causing total devastation of tropical evergreen forests that existed in western India during the depositional time; this change is ultimately responsible for creating dry and desertic conditions prevailing in the area at present.     

Acyl donors for sterol esterification by cell-free preparations from Sinapis alba roots

Homogenates or crude 300-16 000 g membrane fractions from Sinapis alba roots catalysed esterification of [4-¹⁴C]cholesterol with utilization of endogenous acyl sources. With acetone powder preparations cholesterol esterification was distinctly stimulated by a neutral lipid fraction isolated from S. alba roots. Among neutral lipids triacylglycerols were the most active in this process. Experiments with various acyl-labelled acylglycerols as acyl donors and non-labelled sterols as acceptors confirmed that triacylglycerols are directly utilized as the source of fatty acids for sterol esterification. Di- and mono-acylglycerols were much less effective.     

Uvariastrol,a novel cycloartane triterpene from the stem bark of Uvariastrum zenkeri

Uvariastrol, a cycloartane triterpene with a novel tetrahydrofuran/furanone side-chain, has been isolated from the stem bark of Uvariastrum zenkeri and characterized using spectral characteristics, notably high-field ¹H NMR and ¹³C NMR spectroscopy.     

Bullatantriol,a sesquiterpene from annona bullata

Bullatantriol has been isolated from Annona bullata. Its constitution and relative configuration have been established by X-ray analysis. Its absolute configuration has been assigned by chiroptical investigation of the corresponding 7-ketone.     

Annonelliptine,an alkaloid from Annona elliptica

Annonelliptine has been isolated from Annona elliptica and its structure has been identified as (R)-7-hydroxy-1-(4′-hydroxybenzyl)-5,6-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline.