New Guaiane-Type Sesquiterpene and Norsesquiterpene from Alisma plantago-aquatica and Their Xanthine Oxidase Inhibitory Activity.

A new sesquiterpene (1) and a new norsesquiterpene (2) belonging guaiane-type skeleton together with six known compounds (3-8) were isolated from the rhizomes of Alisma plantago-aquatica. Their structures were determined by HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Absolute configurations of new compounds were established by experimental and TD-DFT computational ECD spectra. Compounds 1-8 exhibited xanthine oxidase inhibitory activity with their IC50 values in range of 9.4-66.7 µM. The sesquiterpenoids 1-5 displayed the inhibitory activity and hence they could be potential xanthine oxidase inhibitors from A. plantago-aquatica.

Chemical Constituents from the Leaves of Pachyrhizus erosus Collected in Vietnam.

A phytochemical investigation of methanol extract from leaves of Pachyrhizus erosus (L.) Urban, a leguminous shrub distributed in Vietnam and other tropical and subtropical countries led to the isolation of a new prenylated chalcone, erosusone (1) and a new megastigmane glycoside epimer, 3-episedumoside F1 (9), together with thirteen known compounds including flavonoids (2-6), a 3-benzoxepine lactone (7), a pyridine-4,5-diol derivative (8), megastigmanes and megastigmane glycosides (10-15). Their structures were elucidated by means of high resolution-electrospray ionization (HR-ESI)-MS, one dimensional (1D) and two-dimensional NMR (2D-NMR) spectroscopy as well as comparison with the data reported in the literature. The cytotoxic effects on LU-1 (lung carcinoma), HepG2 (hepatocellular carcinoma), and MCF7 (breast carcinoma) cell lines were assessed. Prenylated chalcones 1-2 and isoflavone 3 exhibited cytotoxicity against all tested cell lines with IC50 values ranging from 22.04 to 45.03 µM.

New cycloartane coronalyl acetate and other terpenoids with anti-inflammatory activity from the leaves of Vietnamese Gardenia philastrei.

Phytochemical study on the methanolic extract of the leaves of Vietnamese plant Gardenia philastrei Pierre ex Pit. has led to the isolation of a new cycloartane coronalyl acetate (1) together with six known ones, coronlolide methyl ester (2), sootepin D (3), coronalolide (4), coronalolic acid (5), sootepin G (6) and 23-deoxojessic acid (7). Their structures were elucidated by a combination of 2 D NMR and HR-ESI-MS spectroscopies. These compounds (1-7) were tested for their anti-inflammatory activity. The result showed that six compounds (1-6) inhibit LPS-induced nitric oxide production in RAW264.7 macrophages with their IC50 values ranging from 3.76 - 75.47 µg/mL. This is the first report on the chemical constituents and anti-inflammatory activity of the G. philastrei.

Characterization of thymol derivatives from Eupatorium fortunei Turcz. aerial parts.

From the aerial parts of Eupatorium fortunei, four thymol derivatives (1-4) were isolated and structurally elucidated by NMR and mass spectroscopic methods. Of which, a new dimeric thymol derivative (1) was characterized and its absolute configuration was established by electronic circular dichroism quantum method. In addition, the 1D and 2D NMR as well as HR-ESI mass spectral data of 2 were provided for the first time. Compounds 2-4 were evaluated for their inhibitory activity against α-glucosidase and acetylcholinesterase enzymes. All tested compounds showed weak inhibition at the concentration range of 1-256 µg/mL in both enzymatic assays.

Sesquiterpenoids from Tithonia diversifolia (Hemsl.) A. Gray induce apoptosis and inhibit the cell cycle progression of acute myeloid leukemia cells.

Three sesquiterpene lactones (1-3) were isolated from the aerial part of Tithonia diversifolia (Hemsl.) A. Gray grown in the Hoa Binh province in Viet Nam. The structures of these three sesquiterpene lactones were identified as tagitinin A (1), 1ß-hydroxytirotundin 3-O-methyl ether (2), and tagitinin C (3) by analyzing spectroscopic data. For the first time, compound 2 was isolated from T. diversifolia growing in Viet Nam. Furthermore, contrary to existing literature, we determined that compound 1 was the major isolate. Compounds 1 and 3 significantly decreased numbers of acute myeloid leukemia OCI-AML3 cells by promoting apoptosis and causing cell cycle arrest at G0/G1 phase at concentrations as low as 2.5 µg/mL (compound 1) and 0.25 µg/mL (compound 3). Additionally, all three compounds showed cytotoxic activity against five human cancer cell lines (A549, T24, Huh-7, 8505, and SNU-1), with IC50 values ranging from 1.32 ± 0.14 to 46.34 ± 2.74 µM. Overall, our findings suggest that compounds 1 and 3 may be potential anti-cancer therapeutics and thus warrant further study.

Myobontioids A-D and antifungal metabolites from the leaves of Myoporum bontioides A. Gray.

A new sesquiterpene glucoside (1), two new norsesquiterpenes (2, 3), and a new homomonoterpene (4), named myobontioids A-D respectively, along with twelve known flavonoids and lignans (5-16) were isolated from Myoporum bontioides A. Gray. Flavanones 5-11 specifically inhibited Phytophthora capsici and Magnaoeporthe grisea at the concentrations of 125, 250 and 500 µg.mL-1. Notably, the new compound 4 possessed a strong activity against Phytophthora capsici with IC50 below 63.5 µg.mL-1 and 90.4% inhibition at 125 µg.mL-1.

Noncytotoxic 16,23-epoxycucurbitacin-type triterpenoids from Elaeocarpus hainanensis.

Phytochemical investigation of methanol extract from Elaeocarpus hainanensis Oliv. leaves and twigs led to the isolation and structural determination of three 16,23-epoxycucurbitacin-type triterpenoids, including a new hydroperoxide, 16α,23α-epoxy-3ß,20ß-dihydroxy-24α-hydroperoxy-10αH,23ßH-cucurbit-5,25-dien-11-one (elahainencin A, 1), and two known analogs (2 and 3). Their chemical structures were determined by the spectroscopic analyses, including 1 D-, 2 D NMR and HR ESI MS spectra. Compound 1 represents a cucurbitacin derivative incorporating a hydroperoxide. In addition, these isolated compounds have been found to be noncytotoxic when tested in vitro against five human cancer cell lines (A549, T24, 8505, Huh-7 and SNU-1) by using the SRB method.

Soluble epoxide hydrolase inhibitors from Docynia indica (Wall.) Decne.

Nine bioactive compounds, including one new dihydroisocoumarin glycoside, 3S-thunberginol C 6-O-ß-D-glucopyranoside (1a/1b), were isolated by chromatographic separation from the fruits of the Vietnamese medicinal plant Docynia indica (Wall.) Decne. 3S-thunberginol C 6-O-ß-D-glucopyranoside was determined as a mixture of boat-like conformers based on NMR evidence and density functional theory (DFT) calculations. The in vitro inhibition of soluble epoxide hydrolase (sEH) by the isolated compounds was comparable to that of AUDA (positive control), yielding IC50 values ranging from 10.0 ± 0.6 to 88.4 ± 0.2 µM. Among isolated compounds, 3-methoxy-4-hydroxy-benzoic acid (7) and 2',6'-dihydroxy 3',4'-dimethoxychalcone (9) were identified as a potent inhibitor of sEH, with IC50 values of 19.3 ± 2.2 and 10.0 ± 0.6 mM, respectively. These results suggest that the fruits of D. indica may be useful as daily supplements for the prevention of cardiovascular and other sEH-related diseases.[Figure: see text].

Optimizing outcomes for patients with metastatic prostate cancer: insights from South East Asia Expert Panel.

AIMS: Clinical decision making is challenging in men with metastatic prostate cancer (mPC), as heterogeneity in treatment options and patient characteristics have resulted in multiple scenarios with little or no evidence. The South East Asia Expert Panel 2019 addressed some of these challenges. METHODS: Based on evidence in the literature and expert interviews, 19 statements were formulated for key challenges in the treatment of men with castration-sensitive and -resistant prostate cancer in clinical practice. A modified Delphi process was used to reach consensus among experts in the panel and develop clinical practice recommendations. RESULTS: The majority of the panel preferred a risk-based stratification and recommended abiraterone or enzalutamide as first-line therapy for symptomatic chemotherapy naïve patients. Abiraterone is preferred over enzalutamide as a first-line treatment in these patients. However, the panel did not support the use of abiraterone in high risk lymph-node positive only (N+M0) or in non-metastatic (N0M0) patients. In select patients, low dose abiraterone with food may be used to optimize clinical outcomes. Androgen receptor gene splice variant status may be a useful guide to therapy. In addition, generic versions of approved therapies may improve access to treatment to a broader patient population. The choice of treatment, as well as sequencing are guided by both patient and disease characteristics, preferences, drug access, cost, and compliance. CONCLUSION: Expert recommendations are key to guidance for the optimal management of mPC. Appropriate choice, timing, and sequence of treatment options can help to tailor therapy to maximize outcomes in men with mPC.

First synthesis of 10 alpha-(trifluoromethyl)deoxoartemisinin.

[reaction: see text] A novel, nonacetal (trifluoromethyl)deoxoartemisinin was prepared with good stereoselectivity. This compound was obtained by debromination of the 10 alpha-CF3-10-bromodeoxoartemisinin in the presence of tributyltin hydride at reflux in toluene without alteration of the endoperoxide bridge. It presented a reasonable antimalarial activity.

Natural anti-HIV agents-part I: (+)-demethoxyepiexcelsin and verticillatol from Litsea verticillata.

The eudesmane sesquiterpenoid, verticillatol (1), as well as the lignan, (+)-5'-demethoxyepiexcelsin (2), and a known lignan, (+)-epiexcelsin (3), were isolated from Litsea verticillata Hance. Lignan 2 showed moderate anti-HIV activity with an IC(50) value of 16.4 microg/ml (42.7 microM), while the known lignan 3 was inactive up to a concentration of 20 microg/ml (48.3 microM). Compound 1 demonstrated weak activity with an IC(50) value of 34.5 microg/ml (144.7 microM) while being devoid of cytotoxicity at 20 microg/ml. The structures were elucidated by 1D and 2D NMR spectroscopy, and the absolute configuration of the new sesquiterpenoid was determined by the generation of Mosher esters.

A new chromone from Hymenocallis littoralis Salisb. (Amaryllidaceae).

A new chromone, 5,7-dihydroxy-6,8-dimethoxy-2-methyl-4H-chromen-4-one (1), together with seven known compounds, 5,7-dihydroxy-6-methoxy-2-methyl-4H-chromen-4-one (pisonin B) (2), 5,7-dihydroxy-2-methyl-4H-chromen-4-one (noreugenin) (3), 5-hydroxy-7-methoxy-2-methyl-4H-chromen-4-one (eugenin) (4), (2S)-7,4'-dihydroxyflavan (5), 3',7-dihydroxy-4'-methoxy-8-methylflavan (6), 3',7-dihydroxy-4'-methoxyflavan (7) and 6,8-dimethyl-5,7,4'-trihydroxyflavanone (( - )-farrerol) (8), were isolated from Hymenocallis littoralis Salisb. (Amaryllidaceae) growing in Vietnam. Their structures were determined based on spectroscopic and physicochemical analyses.

Magnetic chitosan nanoparticles for removal of Cr(VI) from aqueous solution.

A simple method was introduced to prepare magnetic chitosan nanoparticles by co-precipitation via epichlorohydrin cross-linking reaction. The average size of magnetic chitosan nanoparticles is estimated at ca. 30 nm. It was found that the adsorption of Cr(VI) was highly pH-dependent and its kinetics follows the pseudo-second-order model. Maximum adsorption capacity (at pH 3, room temperature) was calculated as 55.80 mg·g(-1), according to Langmuir isotherm model. The nanoparticles were thoroughly characterized before and after Cr(VI) adsorption. From this result, it can be suggested that magnetic chitosan nanoparticles could serve as a promising adsorbent for Cr(VI) in wastewater treatment technology.

Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea.

In a continuing search for anti-HIV compounds from plants of Vietnam, 19 compounds, including a new triterpene, were isolated from an extract of the leaves and stem of Vatica cinerea. The new triterpene was determined to be a cycloartane triterpenoid with 29 skeletal carbons and was assigned the name vaticinone (1). The known triterpenes included three cycloartanes, a lanostane, two dammaranes, three lupanes, an ursane, and an oleanane. A chlorophyll isolate was identified as pheophorbide a (13). The majority of the triterpenes, the sesquiterpene, 1-hydroxycyclocolorenone, and pheophorbide a showed anti-HIV activity, with the chlorophyll being the most active, demonstrating an IC(50) value of 1.5 microgram/mL (2.5 microM), while being completely devoid of toxicity up to a concentration of 20 microgram/mL (33.8 microM). Vaticinone (1) was found to inhibit the replication of HIV-1, with an IC(50) value of 6.5 microgram/mL (15.3 microM; selective index = 1.4). The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra.