A New Taraxastane‐Type Triterpene from Vitex trifolia var. simplicifolia

3‐Oxotaraxer‐14‐en‐30‐al ( 1 ), a new taraxastane‐type triterpene, together with 14 known compounds, taraxerone ( 2 ), 3‐epiursolic acid ( 3 ), 2α,3β‐dihydroxyurs‐12‐en‐28‐oic acid ( 4 ), lupeol ( 5 ), betulinic acid ( 6 ), casticin ( 7 ), artemetin ( 8 ), luteolin ( 9 ), 4‐hydroxybenzoic acid ( 10 ), docosanoic acid ( 11 ), tetracosanoic acid ( 12 ), cerotic acid ( 13 ), β‐sitosterol ( 14 ), and β‐daucosterol ( 15 ), was isolated from the leaves and twigs of Vitex trifolia var. simplicifolia . Compounds 2 – 6 were found for the first time in this plant. Their structures were established by spectroscopic analysis, including 2D‐NMR techniques. Cytotoxic activities of compounds 3 , and 5 – 10 were tested on the three cancer cell lines, PANC‐1, K562, and BxPC‐3. Results revealed that 7 exhibited cytotoxicity against PANC‐1, K562, and BxPC‐3, with IC₅₀ values of 4.67, 0.72, and 4.01 μg/ml, respectively, whereas 8 was inactive against these cancer cell lines. The structure? activity relationship of compound 7 and 8 indicated that the 3′‐OH group in polymethoxyflavonoids is essential for antitumor activity.     

New sesquiterpene hydroperoxides with trypanocidal activity from Pogostemon cablin

Trypanocidal constituents of Pogostemon cablin were investigated. Activity guided isolation of the acetone extract resulted in isolation of three new sesquiterpene hydroperoxides 1-3, together with a known sesquiterpene, patchouli alcohol (4). In vitro minimum lethal concentrations of the hydroperoxides 1-3 against epimastigotes of Trypanosoma cruzi were 0.84 microM (1), 1.7 microM (2) and 1.7 microM (3). The activity of the corresponding alcohols and patchouli alcohol was very weak (MLC>200 microM).     

New norditerpenoids from Cespitularia hypotentaculata

Four new norditerpenoids, designated as cespihypotins A (1), B (2), C (3) and D (4), were isolated from Cespitularia hypotentaculata Roxas (Xeniidae) that was collected in Taiwan. Compounds 1 and 2 are unprecedented structures having 13- and 14-membered lactone ring, respectively. Their structures were elucidated on the basis of extensive spectroscopic analysis. A plausible biogenetic pathway for compounds 1-4 was also proposed.     

Four new halimane-type diterpenes, vitetrifolins D-G, from the fruit of Vitex trifolia

Four new halimane-type (rearranged labdane-type) diterpenes, vitetrifolins D-G were isolated from the fruit of Vitex trifolia L. (Verbenaceae). Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.     

Vitrifolin A: A Norlabdane Diterpenoid from the Fruits of Vitex trifolia Linn. var. simplicifolia Cham

A new norlabdane diterpenoid, named vitrifolin A, was isolated from the fruits of Vitex trifolia Linn. var. simplicifolia Cham. Its structure was elucidated by mean of spectroscopic methods, including HRESIMS, IR, 1D and 2D NMR. The inhibitory effect of vitrifolin A on nitric oxide production in lipopolysaccarideactivated mouse macrophages was also evaluated.     

Validated HPTLC method for the simultaneous quantification of diterpenoids in Vitex trifolia L.

Vitex trifolia L. is an important Indian medicinal plant with diverse pharmacological properties. In a recent study, we reported the isolation and antitubercular activity evaluation of three new diterpenoids from its leaves; here we have developed a validated rapid, simple, precise, and accurate high‐performance TLC method for the simultaneous quantification of isolated diterpenoids in V. trifolia. Diterpenoids, 6α,7α‐diacetoxy‐13‐hydroxy‐8(9),14‐labdadien ( A ), 13‐hydroxy‐5(10),14‐halimadien‐6‐one ( B ), and 9‐hydroxy‐13(14)‐labden‐16,15‐olide ( C ) were separated on silica gel 60F₂₅₄ high‐performance TLC plates using chloroform/acetone (98:2, v/v) as mobile phase. The quantitation of diterpenoids was carried out using densitometric reflection/absorption mode at 610 nm after postchromatographic derivatization using a vanillin/sulfuric acid reagent. A precise and accurate quantification can be performed for compounds A and B in the linear working concentration range of 333–1000 ng/band and for C in the range of 670–2000 ng/band with good correlations (r = 0.9984, 0.9991, and 0.9994, respectively). The method was validated for peak purity, precision, accuracy, robustness, LOD, and LOQ, as per the ICH guidelines. The method reported here is simple, reproducible and may be applied for the quantitative analysis of the above diterpenoids in the leaves of V. trifolia.     

Synthesis of conformationally constrained adamantane imidazolines with trypanocidal activity

Aiming at the development of new adamantano building blocks for treating African trypanosomiasis, we report on the synthesis of spiro adamantane 2‐imidazolines 8a‐f and 9a‐c , and their congeneric 5‐(1‐adamantyl)imidazolines 14 and 15 . The potency of these compounds against Trypanosoma brucei was compared to that of rimantadine and found, in the case of compound 14e , to be three fold higher. Together with the other active compounds, 14b and 15b , which were equipotent to rimantadine, the new molecules illustrate the synergistic effect of the lipophilic character of adamantane and the C1 amidine functionality on trypanocidal activity.     

Enzyme inhibiting lignans from Vitex negundo

Two new lignans trivially named negundins A (1) and B (2), were isolated along with (+)-diasyringaresinol (3), (+)-lyoniresinol (4), vitrofolal E (5) and vitrofolal F (6), reported for the first time from this species. The structures of the new compounds were established through spectral studies. Compound 2 showed potent inhibitory activity against lipoxygenase enzyme, while 5 showed moderate activity against butyryl-cholinesterase.     

A trypanocidal diterpene with novel skeleton from Dracocephalum komarovi

A new diterpene, komarovispirone (1) with a spiro-octahydroindene skeleton, was isolated from Dracocephalum komarovi. The structure was elucidated by extensive analyses of spectral data. Komarovispirone (1) showed trypanocidal activity against epimastigote of Trypanosoma cruzi, the causative agent of American trypanosomiasis, with a minimum lethal concentration of 23 μM.     

Two novel abietane norditerpenoids with anti-inflammatory properties from the roots of Salvia miltiorrhiza var. alba

Salvialba acid (1) with a novel abietane norditerpenoid skeleton and 2-hydroxydihydrotanshinone I (2), a new abietane norditerpenoid, were isolated from Salvia miltiorrhiza var. alba. Their structures were elucidated by spectroscopic analysis and X-ray diffraction. The absolute configuration of 1 was determined by an electronic circular dichroism (ECD) experiment and TDDFT ECD computations. A possible biosynthesis pathway is proposed for 1. Compounds 1 and 2 were demonstrated to have anti-inflammatory effects on vascular inflammation induced by TNF-α in human aortic endothelial cells (HAECs).     

Chemical composition and antimicrobial activity of the essential oil of Sagittaria trifolia

The essential oil of Sagittaria trifolia, a well-known famous medicinal foodstuff in China, was analyzed for the first time using GC-MS. Twenty-eight constituents were identified. The major components of the oil were hexahydrofarnesyl acetone (62.3%), tetramethylhexadecenone (5.8%), myristaldehyde (4.7%), n-pentadecane (2.9%), and 2-hexyldecanol (2.9%).The antimicrobial activity of the essential oil was evaluated against seven microorganisms, including two clinically isolated strains and five reference strains, using microbiological cylinder plate assay and broth microdilution methods. The results showed that the oil had a significant antimicrobial effect on four of them. This antimicrobial activity can partly explain why the oil is used medicinally during childbirth and for skin diseases in Chinese traditional medicine. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 419–420, September–October, 2006.     

New coumarin derivatives from Ferula pseudalliacea with antibacterial activity

In this study, the antibacterial activity of disesquiterpene coumarin and sesquiterpene coumarins obtained from Ferula pseudalliacea roots was evaluated by determination of minimum inhibitory concentration using the broth micro-dilution method against seven pathogenic bacterial strains (Staphylococcus aureus ATCC 25,923, vancomycin resistant clinical strain of Enterococcus faecium, Bacillus cereus PTCC 1015, Escherichia coli ATCC 25,922, Pseudomonas aeruginosa PTCC 1430, clinical strain of Klebsiella pneumoniae and a clinical strain of Helicobacter pylori). The overall inhibitory activities of the compounds were higher against Gram positive tested bacteria. Sanandajin and ethyl galbanate demonstrated significant activity against H. pylori strain, as well as S. aureus strain in concentration of 64 μg/ml. Methyl galbanate inhibited vancomycin resistant strain of E. faecium in concentration of 64 μg/ml. The results of the present investigation indicated that disesquiterpene and sesquiterpene coumarins isolated from F. pseudalliacea root extract can be considered as potent antibacterial agents for pharmaceutical and food industries.     

Two new monoterpene glycosides and trypanocidal terpenoids from Dracocephalum kotschyi

From the whole plant of Dracocephalum kotschyi BOISS., two new monoterpene glycosides (9, 10), together with seven known terpenoids and a phytosterol (1-8), were isolated. Their structures were determined to be limonen-10-al (1), geranial (2), neral (3), beta-sitosterol (4), oleanolic acid (5), ursolic acid (6), p-mentha-8-en-1,2-diol (7), colosolic acid (8), limonen-10-ol 10-O-beta-D-glucopyranoside (9), and limonen-10-ol 10-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside (10). Compounds 1 (3.1 microM), 2 (3.1 microM), 3 (3.1 microM), 5 (6.2 microM), 6 (6.2 microM), and 8 (6.2 microM) were effective against epimastigotes of Trypanosoma cruzi.     

黄荆子挥发性成分的分析

分别采用水蒸汽蒸馏法和超临界流体CO2萃取法提取黄荆子中的挥发性成分.利用气相色谱-质谱(GC/MS)联用技术对其化学成分进行了分析鉴定,并通过面积归一法测定了各成分的相对含量.对两种提取方法的结果进行了比较.结果表明,子午岭的黄荆子中含有多种药用成分,而超临界流体CO2萃取法更能有效地提取黄荆子中的有效成分.     

Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity

A new series of water-soluble tetravalent glycoclusters incorporating β-lactosyl residues attached to a central calix[4]arene core was synthesised using azide-alkyne Cu(I)-catalysed cycloaddition (‘click chemistry’). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14-21 atom spacer arms. The glycoclusters with a C₄-symmetrical arrangement of β-lactosyl residues showed trypanocidal activity, with one of them showing comparable activity to established anti-trypanosomal drug benznidazole in in vitro anti-parasite assays.