Huong Doan Thi Mai

Triterpenoid Saponins from Symplocos lancifolia

Three new bidesmosidic saponins (1-3) and a new ursane triterpenoid, 2α,3β,11α,23-tetrahydroxyurs-12-en-28-oic acid (4), along with seven known compounds, were isolated from a methanolic extract of the leaves of Symplocos lancifolia. The bidesmosidic saponins were found to possess the same sugar unit part, composed of two β-d-glucose moieties and one α-l-rhamnose moiety, linked to maslinic acid, arjunolic acid, and asiatic acid, respectively. Their structures were elucidated by interpretation of their 1D and 2D NMR spectra and completed by analysis of the HRESIMS data. The antibacterial activity of the isolated triterpenoids was evaluated against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa, and several showed activity against Gram-positive bacteria.

Acetylcholinesterase inhibitors from the leaves of Macaranga kurzii.

Bioassay-guided fractionation of an extract of leaves of Macaranga kurzii yielded four new compounds, a stilbene (furanokurzin, 1) and three flavonoids (macakurzin A-C, 2-4). Nine known compounds were also isolated (5-13). Their structures were determined by spectroscopic analyses including MS and 2D NMR. The isolates were all evaluated for acetylcholinesterase inhibitory activity. Compound 6 (trans-3,5-dimethoxystilbene) exhibited the greatest activity (IC50 9 μM). Cytotoxic evaluation against KB cells showed that compound 7 had an IC50 of 4 μM, followed by 11 (IC50 10 μM) and 3 (IC50 13 μM).

Endiandric acid analogues from Beilschmiedia ferruginea as dual inhibitors of Bcl-xL/Bak and Mcl-1/Bid interactions.

A rapid screening by (1)H and (1)H-(13)C HSQC NMR spectroscopy of EtOAc extracts of Endiandra and Beilschmiedia species allowed the selection of Beilschmiedia ferruginea leaves and flowers extract for a chemical investigation, leading to the isolation of 11 new tetracyclic endiandric acid analogues, named ferrugineic acids A-K (1-11). Their structures were determined by 1D and 2D NMR spectroscopic analysis in combination with HRMS data. These compounds were assayed for Bcl-xL and Mcl-1 binding affinities. Ferrugineic acids B, C, and J (2, 3, and 10) exhibited significant binding affinity for both antiapoptotic proteins Bcl-xL (Ki = 19.2, 12.6, and 19.4 μM, respectively) and Mcl-1 (Ki = 14.0, 13.0, and 5.2 μM, respectively), and ferrugineic acid D (4) showed only significant inhibiting activity for Mcl-1 (Ki = 5.9 μM).

Cytotoxic Steroidal Alkaloids from Kibatalia laurifolia

Four new steroids, 3-epi-gitingensine (1), N-acetylgitingensine (6), kibalaurifoline (7) and kibalaurifenone (8), along with the known paravallarine (2), 7α-hydroxyparavallarine (3), gitingensine (4), and N-methylgitingensine (5) were isolated from the leaves of Kibatalia laurifolia. Their structures were determined primarily from mass spectrometry and 2D NMR analyses. On the basis of the known absolute configurations of 2 and 4, the absolute configurations of the new compounds were proposed. Due to the structural relationships of compounds 1-8, a biosynthetic pathway was suggested. Compound 2 was cytotoxic to KB cells (IC50 12.8 μM), followed by 1 with IC50 21.2 μM.

Cytotoxic prenylated isoflavone and bipterocarpan from Millettia pachyloba.

Two new compounds, an isoflavone (1, 6-methoxybarbigerone) and a bipterocarpan (2, pachylobin) were isolated from the grains of Millettia pachyloba (Leguminosae), together with seven known compounds, 5-methoxybarbigerone (3), calopogoniumisoflavone B (4), durmillone (5), jamaicin (6), ichthynone (7), (-)-pisatin (8) and (-)-rotenone (9). The structures were established from spectroscopic analyses, including mass spectrometry and 2D-NMR. Absolute configuration of 2 was proposed based on that of the known compound (-)-pisatine (8). Compounds 1 and 2 exhibited cytotoxicity against KB cells with IC(50) values of 2.0 and 17.6 µM, respectively.

Lignans and other constituents from the roots of the Vietnamese medicinal plant Pseuderanthemum palatiferum.

Two new lignans, palatiferin A (1) and palatiferin B (2), were isolated from the roots of Pseuderanthemum palatiferum, together with five known triterpenes, epifriedelanol (3), lupeol (4), lupenone (5), betulin (6), pomolic acid (7), and a dipeptide asperglaucide (8). Their structures were established from 2D NMR and mass spectroscopy. The absolute configuration of 1 and 2 was proposed based on the comparison of their optical rotation activities with those of compounds with similar structures such as wodeshiol and paulownin. The new lignans, palatiferin A (1) and palatiferin B (2) exhibited a moderate cytotoxicity against KB and HepG2 cell lines. However, betulin and lupeol, two abundant compounds from the roots of P. palatiferum, showed cytotoxic and antimicrobial activities.

Two new sesquiterpenes from the fruits of Fissistigma villosissimum

Abstract Two new sesquiterpenes, namely fissistinone (1) and fissistinol (2), along with ten known compounds (3–12), were isolated from the fruits of Fissistigma villosissimum. Their structures were elucidated on the basis of spectral data analysis, including one-dimensional (1D), two-dimensional (2D)-nuclear magnetic resonance (NMR), and high-resolution–electrospray ionization–mass spectrometry (HR–ESI–MS). Compounds 1–8 were evaluated for their cytotoxic activities against KB cell line; however, all these compounds did not show cytotoxic activity.

Cytotoxic dammarane-type triterpenoids from the leaves of Viburnum sambucinum

Four new dammarane-type triterpenoids (1-4) and twelve known compounds (5-16) were isolated from the leaves of Viburnum sambucinum Reinw. ex Blume. Their structures were determined by spectral data analysis, including MS and 2D NMR. Cytotoxic activity evaluation in vitro against four cancer cell lines (KB, LU-1, HepG2 and MCF7) suggested that the octanor-dammarane derivatives were the main cytotoxic components of the leaves of V. sambucinum.

Two new linear acetogenins from the fruits of Goniothalamus gracilipes

Abstract Two new linear acetogenins, gracilipin A (1) and methylsaccopetrin A (2) along with seven known compounds, saccopetrin A (3), 7,3′,4′-trimethylquercetin (4), rhamnazin (5), casticin (6), isokanugin (7), melisimplexin (8) and 5-hydroxy-3,7-dimethoxy-3′,4′-methylenedioxyflavone (9) were isolated from the fruits of Goniothalamus gracilipes Bân. Their structures were established by spectral analysis, such as mass spectrometry, 1D-NMR, 2D-NMR and circular dichroism (CD). Compounds 1 and 3 showed cytotoxic activity against KB cell line with IC50 values of 14.6 and 15.3 μM, respectively.

New dianthramide and cinnamic ester glucosides from the roots of Aconitum carmichaelii

Abstract Four new compounds N-salicyl-3-hydroxyanthranilic acid methyl ester (1), N-(2′-dehydroxysalicyl)-3-hydroxyanthranilic acid methyl ester (2), methyl-4-β-D-allopyranosyl-ferulate (3), and methyl-4-β-D-gulopyranosyl-cinnamate (4), along with six known compounds (5–10), were isolated from the roots of Aconitum carmichelii Debx. Their structures were elucidated on the basis of spectral data analysis, including 1D, 2D-NMR, and HR-ESI-MS. Compounds 1 and 2 showed the inhibition of nitric oxide (NO) production with IC50 values of 9.13 and 19.94 μM, respectively.