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A new flavonoid, macatanarin D (1), together with five known stilbenes (2-6), was isolated from fruit glandular trichomes of Macaranga tanarius. Their structures were elucidated on the basis of spectroscopic methods and through comparison with data reported in the literature. All isolated compounds were evaluated for their cytotoxic activities against KB and MCF-7 cell lines. Compounds 3, 4, and 5 showed the strongest activities against both cell lines with IC50 values in the range of 0.03–0.12 μM, and compound 2 only showed a significant cytotoxicity against KB cell line (IC50 = 0.26 μM) and a moderate cytotoxicity against MCF-7 (IC50 = 10.4 μM). Compounds 1 and 6 showed weak cytotoxic activities against KB cell line with IC50 values of 29.3 and 24.7 μM, respectively.

Marine microorganisms are an invaluable source of novel active secondary metabolites possessing various biological activities. In this study, the extraction and isolation of the marine sediment Penicillium species collected in Vietnam yielded ten secondary metabolites, including sporogen AO-1 (1), 3-indolecarbaldehyde (2), 2-[(5-methyl-1,4-dioxan-2-yl)methoxy]ethanol (3), 2-[(2R-hydroxypropanoyl)amino]benzamide (4), 4-hydroxybenzandehyde (5), chrysogine (6), 3-acetyl-4-hydroxycinnoline (7), acid 1H-indole-3-acetic (8), cyclo (Tyr-Trp) (9), and 2’,3’-dihydrosorbicillin (10). Their structures were identified by the analysis of 1D and 2D NMR data. Among the isolated compounds, 2-[(5-methyl-1,4-dioxan-2-yl)methoxy]ethanol (3) showed a strong inhibitory effect against Enterococcus faecalis with a minimum inhibitory concentration value of 32 µg/mL. Both 2-[(2R-hydroxypropanoyl)amino]benzamide (4) and 4-hydroxybenzandehyde (5) selectively inhibited E. coli with minimum inhibitory concentration values of 16 and 8 µg/mL, respectively. 2’,3’-Dihydrosorbicillin (10) potentially inhibited α-glucosidase activity at a concentration of 2.0 mM (66.31%).

Three new lavandulylated flavonoids, (2S,2″S)-6-lavandulyl-7,4′-dimethoxy-5,2′-dihydroxylflavanone (1), (2S,2″S)-6-lavandulyl-5,7,2′,4′-tetrahydroxylflavanone (2), and (2″S)-5′-lavandulyl-2′-methoxy-2,4,4′,6′-tetrahydroxylchalcone (3), along with seven known compounds 4−10 were isolated from culture broth of Streptomyces sp. G248. Their structures were established by spectroscopic data analysis, including 1D and 2D nuclear magnetic resonance (NMR), and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). The absolute configurations of 1−3 were resolved by comparison of their experimental and calculated electronic circular dichroism spectra. Compounds 1−3 exhibited remarkable antimicrobial activity. Whereas, two known compounds 4 and 5 exhibited inhibitory activity against Mycobacterium tuberculosis H37Rv with minimum inhibitory concentration (MIC) values of 6.0 µg/mL and 11.1 µg/mL, respectively.

Chemical investigation of the methanol extract of the Vietnamese marine sponge Ircinia echinata led to the isolation of six new 9α-hydroxy-5α,6α-epoxysterols: 5α,6α-epoxycholesta-7,22(E)-dien-3β,9α-diol (1), 5α,6α-epoxycholesta-7,24(28)-dien-3β,9α-diol (2), (24R)-5α,6α-epoxy-24-ethyl-cholesta-7-en-3β,9α-diol (3), 5α,6α-epoxycholesta-7-en-3β,9α-diol (4), (24S)-5α,6α-epoxyergosta-7,22-dien-3β,9α-diol (5), and (24R)-5α,6α-epoxy-24-methyl-cholesta-7-en-3β,9α-diol (6) along with the known 5α-6α-epoxysterols: 5α,6α-epoxystigmasta-7-en-3β-ol (7), 5α,6α-epoxystigmasta-7,22-dien-3β-ol (8), and 5α,6α-epoxyergosta-7-en-3β-ol (9). Their structures and their configurations were established on the basis of high resolution mass spectra and extensive 1D and 2D NMR spectroscopic data and by comparison with the literature. Their cytotoxic activity, evaluated against three human cancer cell lines, MCF-7, Hep-G2 and LU-1, revealed that only compounds 3 and 4 exhibited significant antiproliferative activity and compound 3 showed a selective inhibition towards the MCF-7 human breast cancer cells.

Six new acylated flavonoid glycosides namely barringosides J - O (1-6) along with tephrokaempferoside and barringoside D were isolated from the branches and leaves of Barringtonia pendula. The structural elucidation was confirmed by extensive analysis of their spectroscopic data including HRQTOFMS, 1D and 2D NMR experiments. Moderate inhibitory effects on LPS-induced NO production in RAW264.7 cells were observed for barringosides M (4) and N (5) with IC 50 values of 48.40 ± 3.01 and 56.61 ± 3.87 μM, whereas weak inhibition was found for compounds 1-3, 6, and 7 with IC 50 values ranging from 64.91 ± 3.68 to 79.80 ± 3.90 μM., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier B.V. All rights reserved.)

Using various chromatographic separations, two new cembranoids, ehrenbergols F and G ( 1 and 2 ), along with three known analogs ehrenbergol D ( 3 ), (+)-isosarcophine ( 4 ) and sinulariol Z 2 ( 5 ) were isolated from the soft coral Sarcophyton ehrenbergi . The structural elucidation was done by extensive analysis of the 1 D and 2 D NMR, HR-ESI-QTOF-MS as well as CD experiments. In addition, compounds 1 (IC 50 of 38.38 ± 2.89 µM), 3 (IC 50 of 37.14 ± 3.22 µM) and 4 (IC 50 of 45.01 ± 2.49 µM) revealed moderate inhibitory activity on LPS-induced NO production in RAW264.7 cells, whereas 2 (IC 50 of 73.32 ± 1.95 µM) and 5 (IC 50 of 64.48 ± 4.93 µM) exhibited weak effect.

In the present study, 14 phenolic glycosides, including one new neolignan glycoside, iodescirrhoside A (1), three new flavonol glycosides, iodescirrhosides B-D (2-4), and 10 known metabolites were obtained from the methanol extract of Iodes cirrhosa leaves. Structural elucidation was performed by interpretating the 1D- and 2D- NMR, HR-ESI-MS, and CD spectra in comparison with literature data. All compounds were noncytotoxic to LU-1, HepG2, MCF-7, SK-Mel-2, and LNCaP cancer cell lines. Compound 11 significantly inhibited the growth of E. faecalis. In contrast, weak inhibition was observed for 1-9 and 14 against E. faecalis, for 1, 6-8, and 11 against S. aureus, for 6 and 13 against B. cereus, and 2, 4, and 6-9 against C. albicans., (© 2022 Wiley-VHCA AG, Zurich, Switzerland.)

Two new phenolic glycosides, oroxylumosides A ( 1 ) and B ( 2 ), along with four known compounds darendoside A ( 3 ), leucosceptoside A ( 4 ), acteoside ( 5 ) and decaffeoylacteoside ( 6 ) were isolated from the stem bark of Oroxylum indicum . Their structures were elucidated by extensive analysis of the 1 D and 2 D NMR as well as HR-ESI-QTOF-MS. In addition, compounds 1  -  4 exhibited inhibitory effects on NO production in LPS-stimulated BV2 microglial cell line with IC 50 values of 58.2 ± 2.9, 70.6 ± 3.5, 56.8 ± 2.8 and 61.1 ± 3.1 µM, respectively.

Chemical investigation of the marine-derived endophytic fungus Ascomycota sp. VK12 resulted in isolation and identification of a new compound, (3 R )-(3',5'-dihydroxyphenyl)butan-2-one ( 1 ) and five known ones: AGI-7 ( 2 ), sescandelin ( 3 ), sescandelin-B ( 4 ), 4-hydroxybenzaldehyde ( 5 ), and hydroxysydonic acid ( 6 ). The absolute configuration of 1 was determined by time-dependent density functional theory electronic circular dichroism, specific optical rotation, and NMR calculations. Compounds 1 and 2 showed cytotoxicity towards HepG2, MCF-7, and SK-Mel2 carcinoma cells, with IC 50 values ranging from 48.6 to 96.5 µM. Compounds 1 , 2 , 4-6 displayed NO inhibitory effects in LPS-stimulated BV2 cells, with IC 50 values in a range from 24.2 to 76.5 µM. Compound 2 further inhibited PGE 2 overproduction, with an IC 50 value of 25.3 µM. The inhibitory effects of 2 towards NO and PGE 2 overproduction were found to have a close relationship with its suppression of iNOS and COX-2 protein expression, respectively.

Four new pregnane glycosides, gymlatifosides A - D ( 1 - 4 ) and one known pregnane glycoside, verticilloside J ( 5 ) were isolated from the leaves of Gymnema latifolium Wall. ex Wight. Their chemical structures were elucidated on the basis of extensive spectroscopic methods, including 1D, 2D NMR, HR-ESI-MS, and in comparison with the reported data. All these compounds were tested for α -glucosidase and α -amylase inhibitory activities. Compound 5 exhibited the most anti α -glucosidase activity with inhibitory percentage of 37.8 ± 1.5% at the concentration of 200 μM. Compounds 1-4 showed moderate anti α -glucosidase activity with inhibitory percentage ranging from 7.0 to 30.1%. In addition, all compounds 1-5 showed moderate/weak anti α -amylase activity in the investigated test.

Four new prenylated flavonoids, macarindicins I-IV ( 1-4 ) together with ten known compounds, broussoflavonol F ( 5 ), vedelianin ( 6 ), schweinfurthin E ( 7 ), vitexin ( 8 ), 2″-rhamnosyl vitexin ( 9 ), isovitexin ( 10 ), (6 R ,7 E ,9 R )-9-hydroxy-megastigman-4,7-dien-3-one-9- O - β -D-glucopyranoside ( 11 ), 6 S ,9 R )-roseoside ( 12 ), (6 S ,9 S )-roseoside ( 13 ), and bridelionoside B ( 14 ) were isolated from the leaves of Macaranga indica. Their structures were determined on the basis of extensive spectroscopic methods, including 1D-, 2D-NMR, and MS data. All the isolated compounds were evaluated for their cytotoxic activities against four human cancer cell lines including KB, MCF-7, HepG-2, and LU. As a result, compound 6 significantly exhibited cytotoxic activity against all tested human cancer cell lines with IC 50 values ranging from 4.7 to 11.0 μM. Compounds 2 , 5 , and 7 showed moderate cytotoxic activity with IC 50 values ranging from 7.0 to 38.7 μM.

Three new muurolane type sesquiterpene glycosides, named balanoindicosides A - C ( 1  -  3 ), were isolated from the whole plant of Balanophora fungosa subsp . indica using various chromatographic methods. Their structures were determined by extensive analysis of HR-ESI-MS and NMR spectroscopy. The stereochemistry of muurolane sesquiterpene backbone was demonstrated by NOESY analysis. Configuration of C-12 in compounds 2 and 3 could be distinguished by chemical shift value of C-14. Compounds 1 - 3 exhibited weak cytotoxic activity towards HepG-2, HL-60, LU-1, and MCF-7 cell lines.

Six undescribed sesquiterpene glucosides, fissispallins A-F, and one known sesquiterpene glucoside, fissispallin, were discovered in the leaves of Fissistigma pallens (Finet & Gagnep.) Merr. The structures were determined using spectroscopic methods, including 1D, 2D NMR, and MS. All compounds were evaluated for cytotoxic activity against three human cancer cell lines, HT-29, A-2058, and A-549. Fissispallin A showed potent activity with the IC 50 values less than 1.5 μM against all tested human cancer cell lines. Fissispallin also showed potent activity with IC 50 value of 0.4 ± 0.3 on the A-2058 cancer cell lines. Fissispallins B-D showed significant cytotoxic activity against all the tested cancer cell lines with IC 50 values ranging from 3.8 to 7.2 μM., Competing Interests: Declaration of competing interest No potential conflict of interest was reported by the authors., (Copyright © 2020 Elsevier Ltd. All rights reserved.)

Three new flavonol glycosides, fissflavosides A-C (1-3), together with six known flavonol glycosides, kaempferol 3- O-α -L-rhamnopyranosyl-(1→2)- β -D-galactopyranoside (4), kaempferol 3- O-α -L-rhamnopyranosyl-(1→6)- β -D-galactopyranoside (5), kaempferol 3- O-α -L-rhamnopyranosyl-(1→6)- β -D-glucopyranoside (6), rhamnetin 3- O-α -L-rhamnopyranosyl-(1→2)- β -D-glucopyranoside (7), rutin (8), and isorhamnetin 3- O-α -L-rhamnopyranosyl-(1→2)- β -D-galactopyranoside (9) were isolated from the methanol extract of the Fissistigma pallens leaves. Their chemical structures were determined by 1D-, 2D-NMR, and MS data as well as in comparison with reported data in the literature. Compounds 1-9 showed weak cytotoxic activity on three human cancer cell lines, HT-29, A-2058, A-549 with IC 50 ranging from 134.6 to 162.6 µM. In addition, the antioxidant capacities of compounds were also tested by ORAC assay. All compounds showed significant antioxidant with trolox equivalents ranging from 4.4 to 8.6 µM at the concentration of 1.0 µM. The results indicated 7 and 8 having meaningful reducing capacity of copper (I) ions of 2.7 to 6.9 µM at the concentrations of 1 and 2 µM.

Two new steroid glycosides, granulatosides D ( 1 ) and E ( 2 ), belonging to the group of bi- and monoglycosides of polyhydroxysteroids, respectively, were isolated from the ethanolic extract of the starfish Choriaster granulatus along with thirteen previously known glycosides of polyhydroxysteroids ( 3 - 15 ) and one steroid heptaol ( 16 ). The structures of the new compounds were elucidated by extensive NMR and ESIMS techniques. Cytotoxic and immunomodulatory activities of compounds 1 , 3 - 8 , and 10 - 16 using murine splenocytes and peritoneal macrophages were studied. At a dose of 0.1 μM new glycoside 1 showed immunomodulatory properties, increasing the intracellular ROS (reactive oxygen species) level in peritoneal murine macrophages by 20% and decreasing intracellular ROS level by 21% in pre-treated with endotoxic lipopolysaccharide from E. coli (LPS) peritoneal macrophages.

Until 2004, the secondary metabolites of marine organisms of the Vietnamese territorial waters had been studied very poorly. Only four new compounds were isolated from 1977 to 2003. Joint Russian-Vietnamese expeditions aboard the research vessel 'Akademik Oparin' made it possible to study in detail the chemical diversity of marine micro- and macroorganisms. As a result of five expeditions, more than 250 low-molecular weight natural compounds, including 117 new metabolites, were isolated from marine invertebrates and microfilamentous fungi. Their biological activities, such as cytotoxic, cytoprotective, and antioxidant activities, were investigated. Information about the structure and biological activity of the compounds, the source for their isolation and the geographical location of the objects is summarized in this review., (© 2019 Wiley-VHCA AG, Zurich, Switzerland.)

In a search for anti-inflammatory activity in resources from Vietnamese mangroves, we found that a methanolic extract from the leaves of Calophyllum inophyllum (CIL) showed significant anti-inflammatory effects in vitro. Using various chromatographic techniques, we subsequently isolated 12 compounds (1-12) from a methanolic extract of CIL, including two novel compounds (1-2). The inhibitory effects of these compounds on lipopolysaccharide-induced nitric oxide (NO) production in RAW264.7 cells were also evaluated. Compound 1 significantly suppressed NO production (IC 50  = 2.44 ± 0.88 µM), the secretion of pro-inflammatory cytokines (including interleukin-1 beta and tumor necrosis factor alpha), and the expression of inducible nitric oxide synthase through downregulation of nuclear factor-kappa-B signaling cascades. These results suggest that C. inophyllum leaves might be a useful resource for the development of drugs for the treatment of inflammation., (Copyright © 2019 Elsevier Inc. All rights reserved.)

Background: Many bone-related diseases such as osteoporosis and rheumatoid arthritis are commonly associated with the excessive activity of osteoclasts. Polyscias fruticosa has been used as traditional medicine for the treatment of ischemia and inflammation and also eaten as a salad. However, its effect on the bone related diseases has not been investigated yet., Purpose: This study aimed to investigate the effect of ethanol extract of P. fruticosa on RANKL-induced osteoclastogenesis in vitro and LPS-induced bone loss in mouse, and evaluate anti-osteoclastogenic activities of its major constituents., Methods: BMMs or RAW264.7 cells were treated with ethanol extract from P. fruticose leaves (EEPL), followed by an evaluation of cell viability, RANKL-induced osteoclast differentiation, actin-ring formation, and resorption pits activity. Effects of EEPL on RANKL-induced phosphorylation of MAPKs were evaluated by Western blotting. The expression levels of NFATc1 and c-Fos were evaluated by Western blotting or immunofluorescence assay. The expression levels of osteoclast-specific marker genes were evaluated by Western blotting and reverse transcription-qPCR analysis. A LPS-induced murine bone loss model was used to evaluate the protective effect of EEPL on inflammation-induced bone loss. HPLC analysis was performed to identify the major constituents of EEPL., Results: EEPL significantly inhibited RANKL-induced osteoclast differentiation by decreasing the number of osteoclasts, osteoclast actin-ring formation, and bone resorption. EEPL suppressed RANKL-induced phosphorylation of p38 and JNK MAPKs, as well as the expression of c-Fos and NFATc1. EEPL decreased the expression levels of osteoclast marker genes, including MMP-9, TRAP and CtsK. Mice treated with EEPL significantly protected the mice from LPS-induced osteoclast formation and bone destruction as indicated by micro-CT and histological analysis of femurs. We also identified 3-O-[β-d-glucopyranosyl-(1→4)-β-d-glucuronopyranosyl] oleanolic acid 28-O-β-d-glucopyranosyl ester (1) and quercitrin (3) as the active constituents in EEPL for inhibiting RANKL-induced osteoclast differentiation., Conclusion: The results showed that EEPL exerted anti-osteoclastogenic activity in vitro and in vivo by inhibiting RANKL-induced osteoclast differentiation and function, and suggested that EEPL could have beneficial applications for preventing or inhibiting osteoclast-mediated bone diseases., (Copyright © 2019 Elsevier GmbH. All rights reserved.)

Background: Many bone-related diseases such as osteoporosis and rheumatoid arthritis are commonly associated with excessive activity of the osteoclast. Ganomycin I (GMI), a meroterpenoid isolated from Vietnamese mushroom Ganoderma lucidum, possesses a variety of beneficial effects on human health. However, its impact and underlying mechanism on osteoclastogenesis remain unclear. In the present study, we investigated the effect of GMI on RANKL-induced osteoclast formation in mouse BMMs and RAW264.7 cells., Methods: BMMs or RAW264.7 cells were treated with GMI followed by an evaluation of cell viability, RANKL-induced osteoclast differentiation, actin-ring formation, and resorption pits activity. Effects of GMI on RANKL-induced phosphorylation of MAPKs as well as the expression levels of NFATc1 and c-Fos were evaluated by Western blot analysis. Expression levels of osteoclast marker genes were evaluated by Western blot analysis and reverse transcription-qPCR., Results: GMI significantly inhibited RANKL-induced osteoclast differentiation by decreasing the number of osteoclasts, osteoclast actin-ring formation, and bone resorption in a dose-dependent manner without affecting cell viability. At molecular level, GMI inhibited the RANKL-induced phosphorylation of ERK, JNK, and p38 MAPKs, as well as the expression levels of c-Fos and NFATc1, which are known to be crucial transcription factors for osteoclast formation. In addition, GMI decreased expression levels of osteoclastogenesis specific marker genes including c-Src, CtsK, TRAP, MMP-9, OSCAR, and DC-STAMP in RANKL-stimulated BMMs., Conclusion: Our findings suggest that GMI can attenuate osteoclast formation by suppressing RANKL-mediated MAPKs and NFATc1 signaling pathways and the anti-osteoclastogenic activity of GMI may extend our understanding of molecular mechanisms underlying biological activities and pharmacological use of G. lucidum as a traditional anti-osteoporotic medicine., (Copyright © 2018. Published by Elsevier GmbH.)

Five new secondary metabolites, modiolides D-G (1-4) and 1-(2,5-dihydroxyphenyl)-3-methoxy-butan-1-one (8), one new natural product, 1-(2,5-dihydroxyphenyl)-3-hydroxybutan-1-one (7), along with three known compounds, modiolides A (5) and B (6), and 1-(2,5-dihydroxyphenyl)-2-buten-1-one (9) were isolated from a fermentation culture of the marine endophytic fungus Paraconiothyrium sp. VK-13. Their chemical structures were elucidated by the NMR and MS spectroscopic analysis as well as the modified Mosher's method. Compounds 7 and 9 inhibited the overproduction of proinflammatory mediators NO and PGE 2 in LPS-stimulated RAW264.7 cells, with IC 50 values ranging from 3.9 to 12.5 µM. The inhibitory effects of 7 and 9 on the release of NO and PGE 2 were correlated with their significant suppression of iNOS and COX-2 protein expression, respectively. Furthermore, both compounds 7 and 9 inhibited the mRNA expression of proinflammatory cytokines, including TNF-α, IL-1β, IL-6, and IL-12, with IC 50 values in a range of 2.4-12.5 µM.

Eight compounds were isolated from the leaves of Clerodendrum inerme, including one new rearranged abietane diterpene, crolerodendrum B (1). Their structures were determined by means of spectroscopic methods including one-dimensional and two-dimensional nuclear magnetic resonance (1-D and 2-DNMR), high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) and circular dichroism (CD). The DPPH radical scavenging and cytotoxic activities of isolated compounds against MCF7 (breast), HCT116 (colon) and B16F10 (melanoma) cancer cell lines were evaluated. Compounds 1, 3 and 4 exhibited strong DPPH radical-scavenging effects (ED 50 values of 17.6 ± 2.1, 10.1 ± 0.8 and 11.3 ± 0.3 μM, respectively) and 4 showed strong cytotoxicity against the HCT116 cell line (IC 50  = 3.46 ± 0.01 μM).

Phytochemical investigation of the methanol extract of Vitex limonifolia leaves led to the isolation of three new labdane-type diterpenoids, vitexlimolides A-C (1-3) and eight known compounds, 5,4'-dihydroxy-3,7-dimethoxyflavone (4), vitecetin (5), 5,4'-dihydroxy-7,3'-dimethoxyflavone (6), verrucosin (7), 2α, 3α-dihydroxy-urs-12-en-28-oic acid (8), euscaphlic acid (9), 18,19-seco, 2α, 3α-dihydroxy-19-oxo-urs-11,13(18)-dien-28-oic acid (10), and maslinic acid (11). Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for antiviral activities against CVB3, HRV1B, and EV71 viruses. As a result, compounds 4 and 6 showed potent antiviral activity against CVB3 infection with IC 50 values of 0.12 ± 0.06 and 1.86 ± 0.18 (µM), respectively.

Using various chromatographic methods, one new sesquiterpene quinone named smenohaimien F (1) and five known, neodactyloquinone (2), dactyloquinone C (3), dactyloquinone D (4), isoamijiol (5), and amijiol (6), were isolated from the marine sponge Smenospongia cerebriformis Duchassaing & Michelotti, 1864. Their structures were elucidated by ID-, 2D-NMR spectroscopic analysis, HR-ESI-MS, and by comparing with the NMR data reported in the literature. The cytotoxic activities of the all compounds were evaluated on five human cancer cell lines, LU-1, HL-60, SK-Mel-2, HepG-2, and MCF-7. Compound 4 was found to exhibit significant cytotoxic activities on all tested human cancer cell lines with IC50 values ranging from 0.7 to 1.6 μg/mL.

Using various chromatographic methods, two new alkaloids, antidesoic acids A (1) and B (2) along with fourteen known compounds (3-16) were isolated from the leaves of Antidesma ghaesembilla Gaertn. Their chemical structures were elucidated by physical and chemical methods. All the isolated compounds were evaluated for their inhibitory activity on LPS-stimulated nitric oxide (NO) production in BV2 cells and RAW 264.7 macrophages. Bisflavone 8 significantly inhibited LPS- stimulated NO production in BV2 cells and RAW 264.7 macrophages with IC₅₀ values of 5.4 and 8.0 μM, respectively. Compounds 1-3, 7, 10, 12, 14, and 16 showed moderate inhibitory activities with IC₅₀ values ranging from 11.7 to 77.4 μM.

Two new guaiane derivatives (1 and 2) along with six known sesquiterpenoids (3-8) were isolated from the gorgonian Menella woodin. Their structures -were elucidated by ID and 2D NMR and HRESIMS data as well as by comparison of their spectra with those in the literature. Relative configurations of asymmetric centers in 1 and 2 were suggested on the basis of NOESY and ID NOE correlations, absolute stereochemistry of these compounds was proposed in result of comparison of calculated (for both enatiomers) and experimental ECD. Some suggestions were made regarding a biosynthesis of guaiane sesquiterpenoids in this species. All the compounds were firstly isolated from M woodin.

One new oleanane triterpene glycoside, ardinsuloside (1), and twelve known compounds, demethoxybergenin (2), norbergenin (3), bergenin (4), 4-O-galloylbergenin (5), quercitrin (6), myricitrin (7), myricetin 3-O-(3''-O-galloyl)-α-L-rhamnopyranoside (8), desmanthine-2 (9), epicatechin 3-O-galloyl ester (10), 3'-methoxyepicatechin 3-O-galloyl ester (11), gallic acid (12), and methyl galloate (13) were isolated from the leaves of Ardisia insularis. Their structures were established on the basis of spectral and chemical evidence, which were in agreement with those reported in literature. The cytotoxic activities of these compounds were evaluated on three cancer cell lines namely A-549 (human lung cancer), HT-29 (Human colon adenocarcinoma), and OVCAR (human ovarian carcinoma). The results revealed that compound 1 inhibited A-549, HT-29, and OVCAR cell lines with IC50 values of 8.5 ± 1.2, 16.4 ± 3.1, and 13.6 ± 2.4 μM, respectively. The remaining compound showed weak cytotoxic activity. This result indicated that compound 1 could be useful in the treatment of cancer disease.

Based on our previous finding that certain cembranoid diterpenes possess selective toxicity against protozoan pathogens of tropical diseases such as Trypanosoma and Plasmodium, we have subjected a series of 34 cembranes isolated from soft corals living in the Vietnamese sea to an in vitro screening for anti-protozoal activity against Trypanosoma brucei rhodesiense (Tbr), T. cruzi (Tc), Leishmania donovani (Ld), and Plasmodium falciparum (Pf). Twelve of the tested compounds displayed significant activity against at least one of the parasites. Specifically, 7S,8S-epoxy-1,3,11-cembratriene-16-oic methyl ester (1), (1R,4R,2E,7E,11E)-cembra-2,7,11-trien-4-ol (2), crassumol D (12), crassumol E (13), and (1S,2E,4S,6E,8S,11S)-2,6,12(20)-cembrantriene-4,8,11-triol (16) from Lobophytum crassum, L. laevigatum, and Sinularia maxima showed the highest level of inhibitory activity against T. b. rhodesiense, with IC50 values of about 1 µM or less. Lobocrasol A (6) and lobocrasol C (8) from L. crassum and L. laevigatum exhibited particularly significant inhibitory effects on L. donovani with IC50 values < 0.2 µM. The best antiplasmodial effect was exerted by laevigatol A (10), with an IC50 value of about 3.0 µM. The cytotoxicity of the active compounds on L6 rat skeletal myoblast cell was also assessed and found to be insignificant in all cases. This is the first report on anti-protozoal activity of these compounds, and points out the potential of the soft corals in discovery of new anti-protozoal lead compounds.

Background: In the present study, we examined the inhibitory effects of a methanolic extract, dichloromethane fraction, water layer, and polyhydroxylated sterols (1-4) isolated from the Vietnamese starfish Protoreaster nodosus on pro-inflammatory cytokine (IL-12 p40, IL-6, and TNF-α) production in LPS-stimulated bone marrow-derived dendritic cells (BMDCs) using enzyme-linked immunosorbent assays (ELISA)., Results: The methanolic extract and dichloromethane fraction exerted potent inhibitory effects on the production of all three pro-inflammatory cytokines, with IC50 values ranging from 0.60 ± 0.01 to 26.19 ± 0.64 μg/mL. Four highly pure steroid derivatives (1-4) were isolated from the dichloromethane fraction and water layer of P. nodosus. Potent inhibitory activities were also observed for (25S) 5α-cholestane-3β,4β,6α,7α,8β,15α,16β,26-octol (3) on the production of IL-12 p40 and IL-6 (IC50s = 3.11 ± 0.08 and 1.35 ± 0.03 μM), and for (25S) 5α-cholestane-3β,6α,8β,15α,16β,26-hexol (1) and (25S) 5α-cholestane-3β,6α,7α,8β,15α,16β,26-heptol (2) on the production of IL-12 p40 (IC50s = 0.01 ± 0.00 and 1.02 ± 0.01 μM). Moreover, nodososide (4) exhibited moderate inhibitory effects on IL-12 p40 and IL-6 production., Conclusion: This is the first report of the anti-inflammatory activity from the starfish P. nodosus. The main finding of this study is the identification oxygenated steroid derivatives from P. nodosus with potent anti-inflammatory activities that may be developed as therapeutic agents for inflammatory diseases.

Nine new chromonylthiazolidine derivatives were successfully semi-synthesized from paeonol. All of the compounds, including starting materials, the intermediate compound and products, were evaluated for their cytotoxic effects toward eight human cancer cell lines. The synthesized chromonylthiazolidines displayed weak cytotoxic effects against the tested cancer cell lines, but selective cytotoxic effects were observed. Compounds 3a and 3b showed the most selective cytotoxic effects against human epidermoid carcinoma (IC50 44.1 ± 3.6 μg/mL) and breast cancer (IC50 32.8 ± 1.4 μg/mL) cell lines, respectively. The results suggest that chromoylthiazolidines are potential low-cost, and selective anticancer agents.

A new ent-kaurane glycoside, annoglabasin H (1), and three known ent-kauranes, annoglabasin E (2), annoglabasin B (3), and 19-nor-ent-kaurent-4-ol-17-oic acid (4) were isolated from the fruits of Annona glabra. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparison with the NMR data reported in the literature. The cytotoxic activities of these compounds were evaluated on four human cancer cell lines, LU-1, MCF-7, SK-Mel2, and KB. Compound 1 exhibited significant cytotoxic activity on all tested human cancer cell lines with IC50 values ranging from 3.7 to 4.6 μM.

Six secondary metabolites, including two novel iridoids, longifolides A (1) and B (2), were isolated by various chromatographic methods from a methanol extract of branches and leaves of Morinda longifolia Craib. The structures of the compounds were determined on the basis of NMR spectroscopic (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY) and FTICR-MS data, as well as by comparison of them with literature values.

Marine-derived natural products from invertebrates comprise an extremely diverse and promising source of the compounds from a wide variety of structural classes. This study describes the discovery of five marine natural products with activity against Trypanosoma species by natural product library screening using whole cell in vitro assays. We investigated the anti-trypanosomal activity of the extracts from the soft corals and echinoderms living in Vietnamese seas. Of the samples screened, the methanolic extracts of several marine organisms exhibited potent activities against cultures of Trypanosoma brucei and T. cruzi (EC50 < 5.0 μg/mL). Among the compounds isolated from these extracts, laevigatol B (1) from Lobophytum crassum and L. laevigatum, (24S)-ergost-4-ene-3-one (2) from Sinularia dissecta, astropectenol A (3) from Astropecten polyacanthus, and cholest-8-ene-3β,5α,6β,7α-tetraol (4) from Diadema savignyi showed inhibitory activity against T. brucei with EC50 values ranging from 1.57 ± 0.14 to 14.6 ± 1.36 μM, relative to the positive control, pentamidine (EC50 = 0.015 ± 0.003 μM). Laevigatol B (1) and 5α-cholest-8(14)-ene-3β,7α-diol (5) exhibited also significant inhibitory effects on T. cruzi. The cytotoxic activity of the pure compounds on mammalian cells was also assessed and found to be insignificant in all cases. This is the first report on the inhibitory effects of marine organisms collected in Vietnamese seas against Trypanosoma species responsible for neglected tropical diseases.

Two new isoflavone glycosides, dalspinosin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1) and caviunin 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), and two known compounds, caviunin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3) and caviunin (4) were isolated from the stems of Dalbergia vietnamensis. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparing with the NMR data reported in the literature.

Using a combination of chromatographic methods, one new flavonol glycoside, myricetin 3,7-di-O-alpha-L-rhamnopyranoside (1), and nine known compounds myricitrin (2), quercetin 3,7-di-O-alpha-L-rhamnopyranoside (3), quercitrin (4), desmanthin-l (5), myricetin 3-O-(3"-O-galloyl)-alpha-L-rhamnopyranoside (6), (+)-catechin (7), benzyl O-1-D-glucopyranoside (8), 2-phenylethyl O-beta-D-glucopyranoside (9), and corilagin (10) were isolated from the leaves of Ardisia splendens Pit. Based on an in vitro test against Coxsackie viruses A16 by SRB assay, only compounds 2, 5, and 10 exhibited activity against Coxsackie viruses A16 with IC50 values of 40.1, 32.2, and 30.5 microM, respectively. This result suggested that compounds 2, 5, and 10 might be potential agents for treating hand, foot and mouth diseases.

Sea cucumbers have been used as a dietary delicacy and important ingredient in Asian traditional medicine and functional foods over many centuries. Using combined chromatographic methods, six triterpene saponins (1-6), including a new compound, stichloroside F (1), were isolated from a methanol extract of the sea cucumber Stichopus chloronotus Brandt. Their structures were determined on the basis of spectroscopic (1H and 13C NMR, HSQC, HMBC, 1H-1lH COSY, ROESY) and FTICR-MS data and by comparison with literature values.

One new flavonol glycoside, 4'-O-methylmyricitrin 3'-O-beta-D-glucopyranoside (1), one new sesquiterpene, reynoudiol (11), as well as the 12 known compounds (2-10, 12-14) quercetin 3-O-methyl ether (2), quercitrin (3), isorhamnetin 3-alpha-L-rhamnopyranoside (4), tamarixetin 3-alpha-L-rhamnopyranoside (5), myricitrin (6), 4'-O-methylmyricitrin (7), isorhamnetin 3-O-beta-D-xylopyranosyl (1-2)-O-beta- D-glucopyranoside (8), isorhamnetin 3-O-beta- D-apiofuranosyl(1-2)-O-beta- D-glucopyranoside (9), (+)-catechin (10), 7-drimene-3,11,12-triol (12), clovane-2 beta,9 alpha-diol (13), and a-cadinol (14), were isolated from the methanol extract of Reynoutria japonica roots. Based on in vitro screening of the anti-influenza activity of the isolated compounds, reynoudiol showed significantly higher activity than that of oseltamivir phosphate at the same concentration, and did not induce any detectable cytopathic effect in MDCK cells. The CC50 of reynoudiol was above 50 micro M and could inhibit influenza virus infection with an IC50 of 0.29 +/- 0.01 microM. The therapeutic index (TI) of reynoudiol against influenza infection was 172.4, and thus, this compound can be potentially used to treat oseltamivir-resistant influenza virus infection.

One new schiartane-type triterpene, heteroclitalactone N (1), and four known compounds (2-5), seco-coccinic acid F, dihydroguaiaretic acid, schizanrin F, and kadsuralignan B were isolated from the stems of Kadsura heteroclita. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D-, 2D-NMR, and CD spectra as well as by comparing with the NMR data reported in the literature. The cytotoxic activities of all isolated compounds were evaluated on three human cancer cell lines. Compound 3 exhibited moderate to weak cytotoxic activities on three human cancer cell lines, OVCAR, HT-29, and A-549, with IC50 values ranging from 16.2 to 36.4 microM.

Four new cucurbitane-type triterpene glycosides, charantosides D-G (1-4) were isolated from a methanol extract of Momordica charantia fruits. The structures of these compounds were determined by chemical and spectroscopic methods to be (19R)-5 beta,19-epoxy-25-methoxycucurbita-6,23-diene-3 beta,19-diol 3-O-beta-D-glucopyranoside, (19R)-5 beta, 19-epoxy-25-methoxycucurbita-6,23-diene-3 beta,19-diol 3-O-beta-D-allopyranoside, 7 beta-methoxycucurbita-5,23E,25-triene-3 beta-ol 3-O-beta-D-allopyranoside, and 3 beta,7 beta-dihydroxycucurbita-5,23E,25-triene- 19-al 3-O-beta-D-allopyranoside.

Two new butenolide and pentenolide derivatives, dysideolides A-B, were isolated from the marine sponge Dysidea cinerea. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, and CD spectra, as well as by comparing with the NMR data reported in the literature.

Inflammation is important in biomedical research, because it plays a key role in inflammatory diseases including rheumatoid arthritis and other forms of arthritis, diabetes, heart disease, irritable bowel syndrome, Alzheimer's disease, Parkinson's disease, allergies, asthma, and even cancer. In the present study, we describe the inhibitory effect of crude extracts and steroids isolated from the starfish Astropecten polyacanthus on pro-inflammatory cytokine (Interleukin-12 (IL-12) p40, interleukin-6 (IL-6), and tumor necrosis factor α (TNF-α)) production in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs). Among those tested, compounds 5 and 7 showed potent inhibitory effects on the production of all three pro-inflammatory cytokines with IC50 values ranging from 1.82 ± 0.11 to 7.00 ± 0.16 μM. Potent inhibitory activities were also observed for compound 1 on the production of IL-12 p40 and IL-6 with values of 3.96 ± 0.12 and 4.07 ± 0.13 μM, respectively, and for compounds 3 and 4 on the production of IL-12 p40 with values of 6.55 ± 0.18 and 5.06 ± 0.16 μM, respectively. Moreover, compounds 2 (IC50 = 34.86 ± 0.31 μM) and 6 (IC50 = 79.05 ± 2.05 μM) exhibited moderate inhibitory effects on the production of IL-12 p40, whereas compounds 3 (IC50 = 22.80 ± 0.21 μM) and 4 (IC50 = 16.73 ± 0.25 μM) moderately inhibited the production of TNF-α and IL-6, respectively.

Kalopanax pictus (Araliaceae) is a deciduous tree distributed in Korea, Japan, and China. The stem bark of K. pictus has been functionally used as a traditional crude drug for the treatment of various inflammatory diseases. In the present study, we describe the inhibitory effects of oleanane-type triterpenes and saponins isolated from the stem bark of K. pictus on production of pro-inflammatory cytokines in LPS-stimulated bone marrow-derived dendritic cells. Of the compounds tested, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside (3), nipponogenin E (6), 3β,6β,23-trihydroxyolean-12-en-28-oic acid (7), and caulophyllogenin (19) significantly inhibited the production of IL-12 p40 and IL-6 with IC50 values ranging from 3.3 to 9.1 μM. Compounds 2, 3, 7, and 19 significantly suppressed the secretion of TNF-α with IC50 ranging from 8.8 to 20.0 μM. These data provide scientific support for the use of K. pictus stem bark and its triterpene and saponin components in the inhibition of pro-inflammatory cytokine secretion, including IL-12 p40, IL-6, and TNF-α, and for prevention and treatment of inflammatory diseases.

The anticancer activity of ten compounds from the aerial parts of Glochidion eriocarpum were evaluated on two human cancer cell lines, HL-60 and HCT-116. Compounds 1-4 displayed highly potent cytotoxic activity on the HCT-116 cancer cell line with IC(50) values ranging of 0.41∼1.16 μM. Compounds 1-4 significantly inhibited the HL-60 cell line with IC(50) values ranging of 4.51∼6.33 μM. These results suggested that the benzoyl group at the C-22 position in oleane-type triterpene saponins was essential for cytotoxicity towards tumor cells. Moreover, compounds 2 and 3 showed more potent cytotoxicity than compounds 1 and 4 against HL-60 and HCT-116 cells. With respect to the mechanism underlying cytotoxicity, compounds 1-4 increased chromatin condensation, a typical apoptotic characteristic in HL-60 and HCT-116 cells. In the mechanism of apoptosis induction, compounds 1-4 reduced Bcl-2 expression, whereas the expression of Bax was increased compared to controls in HCT-116 cells. In addition, compounds 1-4 decreased the level of procaspase-3. The cleavage of poly (ADP-ribose) polymerase (PARP), a vital substrate of effector caspase, was observed in HCT-116 cells. Furthermore, the induction of apoptosis was also accompanied by an activation of extracellular signal-regulated kinase (ERK) and p38 kinase in HCT-116 cells. These findings provide evidence demonstrating that the pro-apoptotic effects of compounds 1-4 are mediated through the activation of ERK and p38 in HCT-116 cells.