New cyclopeptide alkaloids from the whole plant of Justicia procumbens L.

Three novel 14-membered cyclopeptide alkaloids, justicianenes B-D (1-3), were isolated from the EtOH extract of the whole plant of Justicia procumbens L., and their structures were determined on the basis of detailed NMR spectroscopic data and the absolute stereochemistry of the ring-bonded α-amino acids in the cyclopeptide alkaloids were determined by ECD spectra. The isolated compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines, including brest cancer MCF-7, cervix carcinoma HeLa, lung cancer A549 and H460, and diphyllin (14) showed moderate cytotoxicity against the HeLa, A549 and H460 cells with IC50 of 9.13, 23.12, 42.34 µM, respectively, justicianene D showed weak cytotoxicity against the MCF-7 cell with inhibition rate of 50% at the concentration of 90 µM.

Anticancer Effects of Five Biflavonoids from Ginkgo Biloba L. Male Flowers In Vitro.

Ginkgo biloba L., an ancient dioecious gymnosperm, is now cultivated worldwide for landscaping and medical purposes. A novel biflavonoid-amentoflavone 7''-O-ß-D-glucopyranoside (1)-and four known biflavonoids were isolated and identified from the male flowers of Ginkgo. The anti-proliferative activities of five biflavonoids were evaluated on different cancer lines. Bilobetin (3) and isoginkgetin (4) exhibited better anti-proliferative activities on different cancer lines. Their effects were found to be cell-specific and in a dose and time dependent manner for the most sensitive HeLa cells. The significant morphological changes validated their anticancer effects in a dose-dependent manner. They were capable of arresting the G2/M phase of the cell cycle, inducing the apoptosis of HeLa cells dose-dependently and activating the proapoptotic protein Bax and the executor caspase-3. Bilobetin (3) could also inhibit the antiapoptotic protein Bcl-2. These might be the mechanism underlying their anti-proliferation. In short, bilobetin (3) and isoginkgetin (4) might be the early lead compounds for new anticancer agents.

Isocoumarin derivatives and monoterpene glycoside from the seeds of Orychophragmus violaceus.

Five new compounds, including four new isocoumarin derivatives [orychophramarin A-D (1-4)] and a new monoterpene glycoside [orychovioside A (5)], together with fourteen known compounds were isolated from the seeds of Orychophragmus violaceus. Their structures were established on the basis of chemical evidence and spectroscopic analysis. Compound 1 showed significant cytotoxicity against HCT-116 and Hela cell lines compared with the positive control group (Cisplatin) with IC50 values of 5.10 and 8.91µM, respectively. Compound 1 exhibited evident cell cycle retardation that arrested HCT-116 cells at G2 phase and induced apoptosis in HCT-116 cells in the further mechanism study.

New lignan glycosides from Justicia procumbens.

Four new lignan glycosides (1-4), named procumbenosides I, K, L, and M, together with cleistanthin B (5) reported for the first time in the genus Justicia, and 5 other known arylnaphthalene lignan glycosides (6-10) were isolated from the whole plant of Justicia procumbens. The structures of the new compounds were elucidated by extensive one-dimensional (1D) and two-dimensional (2D) NMR experiments and mass spectrometry. Procumbenoside M (4) was a rare sesquilignan glycoside never previously reported in the species of Justicia. The paper also provided insight into the conformational equilibria existing in the lignan glycosides of the plant.

New Anti-HBV C-Boivinopyranosyl Flavones from Alternanthera philoxeroides.

C-boivinopyranosyl flavones have rarely been isolated from nature. In the search for anti-HBV (hepatitis b virus) constituents of Alternanthera philoxeroides, two new compounds, luteolin-6-C-ß-D-boivinopyranosyl-3'-O-ß-D-glucopyranoside (1) and chrysoeriol-6-C-ß-D-boivinopyranosyl-4'-O-ß-D-glucopyranoside (2), along with three known C-boivinopyranosyl flavones (compounds 3-5) were isolated. Their structures were determined by spectroscopic analyses including 1D and 2D NMR, HR-ESI-MS, IR spectra. Compounds 1, 2 and 3 showed significant anti-HBV activities through specifically inhibiting the secretion of HBsAg in HepG2.2.15.

Sesquiterpenes and a monoterpenoid with acetylcholinesterase (AchE) inhibitory activity from Valeriana officinalis var. latiofolia in vitro and in vivo.

Acetylcholinesterase Inhibitor (AchEI) is the most extensive in all anti-dementia drugs. The extracts and isolated compounds from the Valeriana genus have shown anti-dementia bioactivity. Four new sesquiterpenoids (1-4) and a new monoterpenoid (5) were isolated from the root of Valeriana officinalis var. latiofolia. The acetylcholinesterase (AchE) inhibitory activity of isolates was evaluated by modified Ellman method in vitro. Learning and memory ability of compound 4 on mice was evaluated by the Morris water maze. The contents of acetylcholine (Ach), acetylcholine transferase (ChAT) and AchE in mice brains were determined by colorimetry. The results showed IC50 of compound 4 was 0.161 µM in vitro. Compared with the normal group, the learning and memory ability of mice and the contents of Ach and ChAT decreased in model group mice (P<0.01), while the AchE increased (P<0.01). Compared with the model group, Ach and ChAT in the positive control group, the high-dose group and the medium-dose group increased (P<0.01), while the AchE decreased (P<0.01). Compound 4 can improve the learning and memory abilities of APPswe/PSΔE9 double-transgenic mice, and the mechanism may be related to the regulation of the relative enzyme in the cholinergic system.

Three spirostanol saponins and a flavane-O-glucoside from the fresh rhizomes of Tupistra chinensis.

Four new compounds, including three new spirostanol saponins [tupistroside G-I (1-3)] and a new flavane-O-glucoside [tupichiside A (4)], together with ten known compounds, were isolated from the fresh rhizomes of Tupistra chinensis. The structures of the new compounds were elucidated by spectroscopic analysis and chemical evidence. All compounds were tested in vitro for their cytotoxic activities against the Human LoVo and BGC-823 cell lines, and six of them were found to possess potent cytotoxicity. Compounds 2, 8 and 9 showed significant cytotoxicity against the tested tumor cell lines with IC50 values ranging from 0.2 to 0.9µM.

New cyclopeptide alkaloid and lignan glycoside from Justicia procumbens.

This study reported a new cyclopeptide alkaloid, justicianene A (1), and a new lignan glycoside, procumbenoside H (2), isolated from Justicia procumbens. The structures of the new compounds were elucidated by means of spectroscopic analysis, including extensive 2D NMR studies and mass spectrometry. Cyclopeptide alkaloids were first observed from the genus Justicia. Compound 2 was cytotoxic against human LoVo colon carcinoma cells with an IC50 value of 17.908 ± 1.949 µM.

Two new flavonols from Cudrania cochinchinensis.

Two new flavonols, 6-p-hydroxybenzyl kaempferol (1) and 6-p-hydroxybenzyl quercetin (2), together with six known compounds were isolated from the roots of Cudrania cochinchinensis and their structures elucidated on the basis of spectroscopic methods. Their antioxidant capacities were evaluated by 1,1-diphenyl-2-picryl-hydrazyl and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical-scavenging assays. The results suggested that compounds 2, 4, and 7 showed significant radical-scavenging activities.

Cytotoxic activity of lignans from Justicia procumbens.

Three new lignans, Pronaphthalide A (1), Procumbiene (2), and Procumbenoside J (3), along with a novel natural product Juspurpudin (4), and twelve other known lignans were isolated from Justicia procumbens. The structures of the new compounds were elucidated by extensive spectroscopic analyses and the data of 3 provided insight into the conformational equilibria existing in it. All compounds were evaluated for their in vitro cytotoxic activity against Human LoVo and BGC-823 cell lines except for compound 2, and eight of them were found to possess potent cytotoxicity. The structure-activity relationship (SAR) analysis revealed that (i) the parent structure of 2-carbonyl arylnaphthalide lactone attached with 6 and 7-OMe was the essential element; (ii) the polarity of substituents on C-4 might significantly affect the activity; (iii) a proper cyclic lipophilic group at the C-3″ and C-5″ of apiofuranose on C-4 might enhance the activity, which could optimize the application of 3 similar to VP-16.

Two new coumarins from the seeds of Solanum indicum.

Two new coumarins, (E)-2-(4-hydroxy-3-methoxybenzylidene)-5-methoxy-2H-[1,4]dioxino[2,3-h]chromene-3,9-dione (indicumin E, 1) and 7-hydroxy-6,8-dimethoxy-3-(4'-hydroxy-3'-methoxyphenyl)-coumarin (2), together with two known coumarins isofraxidin (3) and fraxetin (4), were isolated from the Solanum indicum seeds. Their structures were established on the basis of 1D and 2D spectroscopic data. Compound 1 was the rarest coumarinolignoid known to date.

Three new germacrane-type sesquiterpenes with NGF-potentiating activity from Valeriana officinalis var. latiofolia.

Three new germacrane-type sesquiterpenoids, volvalerenal F (1), volvalerenal G (2) and volvalerenic acid D (3), along with five known compounds 4-8, were isolated from the CHCl3 soluble partition of the ethanol extract of Valeriana officinalis var. latiofolia. The structures of the new compounds were determined on the basis of spectroscopic evidence, including their 1D- and 2D-NMR spectra, as well as mass spectrometry. The eight germacrane-type sesquiterpenoids showed nerve growth factor (NGF) potentiating activity, which mediates the neurite outgrowth in PC 12D cells. This study intends to reveal the chemical basis of the use of V. officinalis var. latiofolia as a dietary supplement.

[Chemical constituents of Cudrania cochinchinensis].

OBJECTIVE: To study the chemical constituents of Cudrania cochinchinensis. METHODS: Compounds were isolated and purified by silica gel column, sephadex LH-20 chromatography and recrystallization. Their structures were elucidated by physicochemical properties and spectral data. RESULTS: Thirteen compounds were isolated from the 70% ethanol extract of the root of Cudrania cochinchinensis and identified as beta-sitosterol (1), butyrospermol (2), butyrospermol acetate (3), (+) syringarenol (4), 1, 3, 6-trihydroxy-7-methoxy xanthone (5), 1, 3, 6, 7-tetrahydroxy-8-prenylxanthone (6), kaempferol (7), dihydrokaempferol (8), umbelliferone (9),4-hydroxybenzyl ethyl ether (10), 2,4-dihydroxybenzaldehyde (11), 4-hydrox-ybenzaldehyde (12) and vanillin (13). CONCLUSION: Compounds 2 - 6, 10 - 13 are isolated from Cudrania cochinchinensis for the first time.

Four new coumarinolignoids from seeds of Solanum indicum.

Activity-guided fractionation of seeds of Solanum indicum for anti-HBV activity led to the isolation of two novel coumarinolignoid alkaloids (indicumines A-B, 1-2) and two new coumarinolignoids (indicumines C-D, 3-4), together with four known coumarins (5-8). Their structures were established on the basis of spectroscopic data. The two novel coumarinolignoid alkaloids shows anti-HBV activities through specifically inhibiting the secretion of HBsAg in HepG2.2.15.

Two novel secoiridoid glucosides from Tripterospermum chinense.

Two novel secoiridoid glucosides, tripterospermumcins C (1) and D (2), were isolated from the aerial parts of Tripterospermum chinense, along with four known compounds, tripterospermumcin B (3), sweroside (4), loganic acid (5), and 8-epi-kingiside (6). Their structures were determined by analysis of 1D and 2D NMR data, as well as by comparison with model compounds. Compound 1 was a rare iridoid tetramer with four glucosides.

A novel lactone from Tripterospermum chinense.

A novel lactone, tripterospermumcins E (1), along with four known compounds, sweroside (2), loganic acid (3), 8-epi-kingiside (4) and bergenin (5), were isolated from the aerial parts of Tripterospermum chinense. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, and chemical methods. Compound 1 is rare beta-lactone with a glucoside.

[A new triterpenoid fom Radix Pittospori].

To investigate chemical constituents from Radix Pittospori, chloroform extract of the roots was subjected to column chromatography with various chromatographic techniques. The structures were elucidated on the basis of physico-chemical property and spectral analysis. Two triterpenoids were identified as 22-acetyl-21-(2-acetoxy-2-methylbutanoyl)-R1-barrigenol(1) and 3alpha-hydroxyl-20-demethylisoaleuritolic-14(15)-ene-28, 30-dioic acid (2). Compound 1 is a new triterpene and compound 2 is isolated from this plant for the first time.

[Triterpenoid saponins of Alternanthera philoxeroides (Mart.) Griseb].

In order to find the anti-virus constituents of Alternanthera philoxeroides (Mart.) Griseb, the investigation was carried out. The paper reported the five triterpenoid saponins isolated from n-BuOH fraction: 3-O-beta-D-glucopyranosyl (1-->3)-O-[beta-D-glucopyranosyl-oleanolic acid]-28-O-beta-D-glucuronopyranoside (1), oleanolic acid-3-O-beta-D-glucuronopyranoside (calenduloside E, 2), oleanolic acid-3-O-beta-D-glucopyranosyl-28-Obeta-D-glucopyranosyl ester (chikusetsusaponin-IVa, 3), 3-O-(6'-O-butyl-beta-D-glucuronopyranosyl)-oleanolic acid-28-O-beta-D-glucopyranosyl ester (4) and hederagenin-3-O-beta-D-glucuronopyranoside (HN-sapoins K, 5). 1 is a new compound, saponins 4 and 5 were isolated from the plant for the first time.

New anti-HBV caryophyllane-type sesquiterpenoids from Euphorbia humifusa Willd.

Activity-guided fractionation of Euphorbia humifusa for anti-HBV activity led to the isolation of two novel sesquiterpenoids, named humifusane A (1) and humifusane B (2). Their structures were elucidated by spectral data to show that they have a caryophyllane-type precursor structure. The two new sesquiterpenoids showed anti-HBV activities through specifically inhibiting the secretion of HBsAg in HepG2.2.15.

Anti-HBV active flavone glucosides from Euphorbia humifusa Willd.

Thirteen flavone glucosides from the herb of Euphorbia humifusa were isolated and elucidated. Among them, five compounds including apigenin-7-O-ß-D-glucopyranoside (2), apigenin-7-O-(6''-O-galloyl)-ß-D-glucopyranoside (3), luteolin-7-O-ß-D-glucopyranoside (7), luteolin-7-O-(6''-O-trans-feruloyl)-ß-D-glucopyranoside (8) and luteolin-7-O-(6''-O-coumaroyl)-ß-D-glucopyranoside (9) showed anti-HBV activity in vitro. The structure-activity relationship showed that the parent structure was closely relevant to the anti-HBV activity of these compounds (agigenin>luteolin>quercetin). It was found that the number of glucoside in the structure may significantly influence their activities (flavone monoglucoside>flavone diglucoside) and cytotoxicity (flavone>flavone monoglucoside>flavone diglucoside). In addition, the substitution of acyl group on glucoside may be important to keep the anti-HBV activities of these compounds (galloyl>feruloyl>coumaroyl).