Chemical constituents of Pithecellobium albicans

A new ent-kaurane diterpene glycoside identified as (-)19-beta-D-glucopyranosyl 6,7-dihydroxy kaurenoate, was isolated from the seeds of Pithecellobium albicans. The structure of the new compound was established by spectral data.     

Chemical constituents of Daphne oleoides

The isolation of daphnetin 8-O-β-d-glucopyranoside (1), 4-ethoxybenzoic acid, 4-hydroxybenzoic acid and grantioidin from Daphne oleides (whole plant) is reported along with ¹H- and ¹³C-NMR spectra of 1.     

Chemical constituents of Lobelia chinensis

Three new 2, 6-disubstituted piperidine alkaloids (1–3), one new polyacetylene (8), together with eight known compounds (4–7, 9–12) were isolated from the whole plants of Lobelia chinensis. Their structures were elucidated on the basis of spectroscopic data interpretation. The absolute configuration of 1 was established by a convenient Mosher ester procedure in which the sample was treated with MTPA chlorides in deuterated pyridine directly in NMR tube. Cytotoxicities of compounds 1–12 were tested against two human lung cancer cell lines, NCI-H292 and MSTO-211H. Compounds 8 and 9 exhibited moderate cytotoxic activity against the two cancer cell lines with the IC₅₀ values in the range of 9.31–12.36 μM.     

Chemical constituents of Roldana lineolata

The new eremophilanolide 1, the known eremophilane derivatives 2 and 3, already described as part of mixtures, the known compounds hyperin, 2'-acetylhyperin and two calenduladiol esters were isolated from Roldana lineolata. Their structures were determined by spectroscopic methods. Compounds 1 and 2 as well as their acetylated and oxidized derivatives were tested against several fungi strains. Eremophilanolide 1 showed a mild activity against Trichophyton mentagrophytes.     

Chemical constituents from Tillandsia recurvata

The CHCl3 extract of Tillandsia recurvata yielded 5,3'-dihydroxy-6,7,8,4'-tetramethoxyflavanone (1), 1,3-di-O-cinnamoyl-glycerol (2) and ethyl ester of caffeic acid. Their structures were elucidated by means of spectroscopic methods such as mass spectroscopy and 1 and 2D-NMR.     

Chemical constituents from Asparagus dumosus

The isolation and characterization of calonysterone (1), blechnoside B (2), 20-hydroxyecdysone and isovanillin from the whole plant of Asparagus dumosus are being reported for the first time from this source.     

Chemical constituents from Aphanamixis grandifolia

Four new terpenoids, nemoralisins D–G (1–4), were isolated from the leaves and stems of Aphanamixis grandifolia, along with two known diterpenoids, nemoralisin C and nemoralisin. Among them, compound 1 is the first example of norsesquiterpenoid with δ-lactone moiety, and nemoralisins E–G (2–4), are a class of acyclic diterpenoids, which are structurally related nemoralisin C and nemoralisin. These structures were established on the basis of spectroscopic methods and the absolute configuration of 1 was determined by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Nemoralisins D–G (1–4) were tested for their cytotoxicities on HL-60, SMMC-7721, A-549, MCF-7, and SW480 human tumor cell lines (IC₅₀ > 40 μM), as well as the antimicrobial activities on Staphylococcus aureus, Pseudomonas aeruginosa, MRSA92^# and MRSA98^# (MIC > 50 μg/mL).     

Chemical constituents from the linseed meal

One megastigmane derivative 1, one methyl jasmonate glycoside derivative 2, and two C-28 steroids with 3β,5β-cis-dihydroxyl conformation 3 and 4, together with eight known compounds 5–12 were isolated from the 70% ethanol extract of linseed meal (Linum usitatissimum L). Structures of 1–4 were elucidated by spectroscopic methods including NMR, HRESIMS, and Mo₂(OAc)₄-induced CD. The absolute configuration of 1 and 3 was determined by observing their induced circular dichroism after addition of Mo₂(OAc)₄ in DMSO. The absolute configuration of 2 was determined by NOESY experiment together with conformational analysis. The structure of 4a was corrected as 4 by an extensive analysis of its 1D and 2D NMR, in combination with the Mo₂(OAc)₄-induced CD in DMSO. The effect of all the isolates on nitric oxide (NO) generation by stimulated macrophages was evaluated, and none of them showed active.     

Chemical constituents of Tolpis species

Phytochemical research of two Tolpis species, T. webbii and T. sp., led to the isolation of three new compounds: 2,4′-dihydroxy-4-methoxybenzophenone (1) and the triterpenes 21α, 22α-epoxy-20α-hydroxy-20(30)-dihydrotaraxasterol (2) and 3β-hydroxytaraxaster-20-en-30-oic acid (3) together with 16 known compounds. The structures of the new compounds were elucidated by means of extensive IR, NMR, MS and X-ray analysis and by comparison of data reported in the literature.     

Chemical constituents of the bark of Gallesia gorazema

Chemical composition analysis of the essential oil from the bark of Gallesia gorazema was carried out by GC/MS. This analysis led to the identification of six non-sulfurated and 19 sulfurated compounds.     

Chemical constituents from endophytic fungus Fusarium oxysporum

A new oxysporidinone analogue (1) and a new 3-hydroxyl-2-piperidinone derivative (2), along with the known compounds (−)-4,6′-anhydrooxysporidinone (3), (+)-fusarinolic acid (4), gibepyrone D (5), beauvercin (6),cerevisterol (7), fusaruside (8), and (2S,2′R,3R,3′E,4E,8E)-1-O-D-glucopyranosyl-2-N-(2′-hydroxy-3′-octadecenoyl)-3-hydroxy-9-methyl-4,8-sphingadienine (9) were isolated from Fusarium oxysporum. Compounds 1-9 were evaluated for cytotoxicity using the MTT method against cancer cell lines, PC-3, PANC-1, and A549. Beauvericin showed cytotoxicity against PC-3, PANC-1, and A549 with IC₅₀ value of 49.5 ± 3.8, 47.2 ± 2.9, and 10.4 ± 1.6 μM, respectively. Beauvericin also exhibited anti-bacterial activity towards methicillin-resistant Staphylococcus aureus (MIC = 3.125 μg/mL) and Bacillus subtilis (MIC = 3.125 μg/mL).     

Chemical constituents investigation of Daphne tangutica

A phytochemical study of an ethanol-soluble extract from the root barks of Daphne tangutica Maxim., a traditional Tibetan herb medicine, led to the isolation of 30 compounds, including eight daphnane diterpenes, nine coumarines, six lignans, five phenylpropanoid derivatives, β-sitosterol and p-hydroxy benzonate. Two compounds out of these isolates are new daphne diterpene analogs, and their structures were established as 1,2α-dihydro-5β-hydroxy-6α,7α-epoxy-resiniferonol-14-benzonate, and 1,2β-dihydro-5β-hydroxy-6α,7α-epoxy-resiniferonol-14-benzonate, respectively, on the basis of spectroscopic methods. Additionally, this is the first time that 13 known compounds have been isolated and identified from this traditional Tibetan medicinal plant.     

Chemical constituents of the aerial part of Derris elliptica

A new coumaronochromone, 6,4'-dihydroxy-7,5' -dimethoxy-coumaronochromone (1), together with eleven known flavonoids (2-12) were isolated from the ethanol extract of the aerial part of Derris elliptica. Their structures were elucidated on the basis of spectroscopic analysis. Compounds 2, 4, 7, 8 and 9 exhibited moderate insecticidal activities against larvae of Aedes albopictus. All compounds showed strong cytotoxic activities against Spodoptera litura (SL) and Trichoplusia ni BTI-Tn-5B1-4 (Hi-5) cells comparison to positive control of rotenone.     

Chemical constituents of Ganoderma applanatum of British Columbia forests

A new compound, ganoderma aldehyde (1),was isolated from the fruiting body of Ganoderma applanatum. Its structure was elucidated on the basis of one-dimensional and two-dimensional NMR as well as MS spectroscopic analysis.     

Chemical constituents from the fruits of Gardenia jasminoides Ellis

A new lignan glucoside, (+)-(7S,8R,8'R)-lyoniresinol 9-O-β-D-(6″-O-trans-sinapoyl)glucopyranoside (1), and a new iridoid glucoside, 10-O-trans-sinapoylgeniposide (2), together with eight known compounds, were isolated from the fruits of Gardenia jasminoides Ellis. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D and 2D NMR, ESI-MS, HR-ESI-MS, and CD experiments. The short-term-memory-enhancement activities of some compounds were evaluated on an Aβ transgenic drosophila model.     

Chemical constituents of Anacolosa pervilleana and their antiviral activities

In an effort to identify novel inhibitors of Chikungunya (CHIKV) and Dengue (DENV) virus replication, a systematic study with 820 ethyl acetate extracts of Madagascan plants was performed in a virus-cell-based assay for CHIKV and a DENV NS5 RNA-dependant RNA polymerase (RdRp) assay. The extract obtained from the leaves of Anacolosa pervilleana was selected for its significant activity in both assays. One new (E)-tridec-2-en-4-ynedioic acid named anacolosine (1), together with three known acetylenic acids, the octadeca-9,11,13-triynoic acid (2), (13E)-octadec-13-en-9,11-diynoic acid (3), (13E)-octadec-13-en-11-ynoic acid (4), two terpenoids, lupenone (5) and β-amyrone (6), and one cyanogenic glycoside, (S)-sambunigrin (7) were isolated. Their structures were elucidated by comprehensive analyses of NMR spectroscopy and mass spectrometry data. The inhibitory potency of these compounds was evaluated on CHIKV, DENV RdRp and West-Nile polymerase virus (WNV RdRp). Both terpenoids showed a moderate activity against CHIKV (EC(50) 77 and 86 μM, respectively) and the acetylenic acids produced IC(50) values around 3 μM in the DENV RdRp assay.     

Chemical constituents from Euphorbia stracheyi and their biological activities

Three new diterpenoids, stracheyioids A–C (1–3), as well as 36 known compounds (4–39) were isolated from the whole plants of Euphorbia stracheyi. Compound 1 was a rare 13-deoxy tigliane diterpenoid and compound 2 was an ingenol diterpenoid characterized by an unique 2Z,4Z-decadienoyl acidic moieties. All the known compounds were isolated from E. stracheyi for the first time. Their structures were elucidated on the basis of extensive spectroscopic interpretation. Compounds 1–39 were tested for their cytotoxicity against five cancer cell lines (A-549, MCF-7, Hep G2, Hela and P388) and showed IC₅₀ values in the range 6.64–42.86 μM. The antiangiogenic activities of the isolated compounds were also evaluated using a zebrafish model.     

Chemical constituents of the Vietnamese liverwort Porella densifolia

From the ether extract of Porella densifolia, the first liverwort collected and chemically investigated in Vietnam, a kaurane diterpenoid, ent-kauren-15-one (1) and two sesquiterpene norpinguisone (2) and norpinguisone methyl ester (3) have been purified. Their structures were elucidated by spectroscopic analysis. In addition, an X-ray crystal structure of norpinguisone was obtained, allowing to determine its stereochemistry. Furthermore, the inhibitory activity of nitric oxide (NO) production in RAW 264.7 cells stimulated by lipopolysaccharide (LPS) of compounds 1–3 was examined with their IC₅₀ values of 69.4, 45.5 and 1.68 μM, respectively.     

Chemical constituents from the radix of Curcuma wenyujin

Phytochemical study on the ethanol extract of the radixes of Curcuma wenyujin Y. H. Chen et C. Ling led to the isolation of three new compounds curcuminol F (1) curcuminol G (2) and wenyujinoside (3) and a known compound aurantiamide (4). Their structures were elucidated on the basis of extensive spectroscopic analysis.     

Chemical constituents of Swertia yunnanensis and their anti-hepatitis B virus activity

Four new triterpenoids, sweriyunnangenin A (1), sweriyunnanosides A (2), B (3) and C (4), along with nineteen known compounds (5–23) were isolated from Swertia yunnanensis. Based on extensive spectroscopic analyses (1D- and 2D-NMR, HRESIMS, UV, IR, [α]_D), the structures of sweriyunnangenin A (1), sweriyunnanosides A (2), B (3) and C (4) were elucidated as taraxer-14-ene-3α,6β-diol, oleanolic acid 28-O-β-d-glucopyranosyl-(1 → 2)-O-β-d-glucopyranoside, 2α,3β-di-hydroxyolean-12-en-28-oic acid 28-O-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl (1 → 6)-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranoside and hederagenin 28-O-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranoside, respectively. Twenty-two compounds were evaluated for their anti-HBV activities on the HepG 2.2.15 cell line in vitro, of which nine compounds showed potent anti-HBV activities. Compounds 1, 5–6, 14–16 and 19 showed activities against the secretion of HBsAg (IC₅₀ values from 0.10 to 1.76 mM) and HBeAg (IC₅₀ values from 0.04 to 1.41 mM), and compounds 11 and 13–16 exhibited significant inhibition on HBV DNA replication (IC₅₀ values from 0.01 to 0.09 mM).