Diterpenes with potential treatment of vitiligo from the aerials parts of Euphorbia antiquorum L.

Six new diterpenes Euphonoids A-F including one ingenol (1), three lathyrane (2-5), one ent-abietane (6) and fifteen known derivatives (7-21) were isolated from the aerial parts of Euphorbia antiquorum L. Their structures were elucidated by physical data analysis. Compounds 1, 12, and 16 improve the melanogenesis in B16 cells in vitro.

Two new bioactive lignans from leaves and twigs of Cleistanthus concinnus Croizat.

Two new lignans (1-2), along with five known compounds (3-7) with different structures were isolated from leaves and twigs of Cleistanthus concinnus Croizat. The new lignans were elucidated as (7'R,8'S)-3,3',5'-trimethoxy-4,4'-dihydroxy-7-en-7',9- epoxy-8,8'-lignan (1) and (7'R,8'S)-3,3'-dimethoxy-4,4'-dihydroxy-7-en-7',9-epoxy-8, 8'-lignan (2) by comprehensive spectroscopic analysis including 1D and 2D NMR as well as HREIMS and comparing their NMR data with known compounds in the literature. Among these isolated compounds, compound 1, 2, 3, and 6 were tested for anti- inflammatory effects by inhibiting NO production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Compound 1, 2, and 6 exhibit NO inhibitory activity.[Formula: see text].

Stelleraguaianone B and C, two new sesquiterpenoids from Stellera chamaejasme L.

Two new sesquiterpenoids were isolated from Stellera chamaejasme L., known as the traditional Chinese herb 'Rui Xiang Lang Du'. The compounds were elucidated as stelleraguaianone B (1) and C (2) by comprehensive spectroscopic analysis, including 1D and 2D NMR as well as HRESIMS, and by comparing their NMR data with known compounds. In addition, the structure of 1 was further confirmed by single-crystal X-ray diffraction analysis. Both the compounds were evaluated for their cytotoxicity on common tumour cell lines in vitro, which revealed that compound 1 exhibits cytotoxic activity on A549 cells, while 2 has no activity.

Hypermonins A and B, two 6-norpolyprenylated acylphloroglucinols with unprecedented skeletons from Hypericum monogynum.

Two new 6-norpolycyclic polyprenylated acylphloroglucinols (PPAPs), hypermonins A (1) and B (2), featuring an undescribed decahydroindeno[1,7-bc]furan ring system, were isolated from the leaves and twigs of Hypericum monogynum. These compounds are a pair of epimers with opposite configurations at the C-5 position. Their structures, including their absolute configurations, were determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. A plausible biosynthetic pathway of 1 and 2 was also proposed. Compound 1 exhibited a significant protective effect against corticosterone-induced injury in PC12 cells.

Cytotoxic indole alkaloids from Melodinus khasianus and Melodinus tenuicaudatus.

Four new indole alkaloids, melodinusines A-D (1, 2, 6, and 7), along with 26 known indole alkaloids, were isolated from Melodinus tenuicaudatus and Melodinus khasianus (Melodinus genus). Among them, 1 and 2 are aspidospermine-aspidospermine-type bisindole alkaloids while 7 is a novel melodinus-type alkaloid. Their structures were established on the basis of comprehensive spectroscopic data analysis and the structure of 7 was further confirmed by single-crystal X-ray diffraction analysis. Their cytotoxic activities against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7, and SW480 were also evaluated.

Two novel diterpenoid heterodimers, Bisebracteolasins A and B, from Euphorbia ebracteolata Hayata, and the cancer chemotherapeutic potential of Bisebracteolasin A.

Rare ent-abietane-rosane diterpenoid heterodimers, Bisebracteolasins A and B (1 and 2, respectively), were isolated from the roots of Euphorbia ebracteolata Hayata. Their structures and absolute configurations were elucidated from spectroscopic data and X-ray diffraction analysis. Compounds 1 and 2 exhibited moderate cytotoxic effects against five cancer cell lines. Compound 1 showed more effective antiproliferative activities against human tumour cells, HL-60 and SMMC-7721, with IC50 values of 2.61 and 4.08 µM, respectively, than 2. Both compounds 1 and 2 inhibit the colorectal cancer stem cell line P6C with IC50 values of 16.48 and 34.76 µM, respectively. Moreover, preliminary biological tests showed compound 1 exhibited inhibitory activity towards tumoursphere formation and migration of the P6C cell line. Overall, we identified two novel diterpenoid heterodimers, and Bisebracteolasin A exhibits therapeutic potential in impeding tumour growth and metastatic ability of cancer stem cells.

(±)-Perforison A, A Pair of New Chromone Enantiomers from Harrisonia perforata.

(+)-Perforison A and (-)-perforison A, a new pair of chromone enantiomers, along with four known compounds, were isolated from the leaves and stems of Harrisonia perforata. Their structures and absolute configurations were determined on the basis of extensive analysis of spectroscopic data and electronic circular dichroism (ECD) calculations. The cytotoxic activities in vitro of these compounds were evaluated, but none showed significant activity.

Four new tetracyclic alkaloids with cis-decahydroquinoline motif from Myrioneuron effusum.

Four new Myrioneuron alkaloids, mysumamides A-D (1-4), along with three known ones were isolated from the twigs and leaves of Myrioneuron effusum. All of these alkaloids possessed the tetracyclic skeleton and contained the decahydroquinoline (cis-DHQ) moiety. Their structures and relative configurations were elucidated on the basis of spectroscopic methods, especially 2D NMR techniques. The absolute configuration of 1 was determined by single-crystal X-ray diffraction. The cytotoxic activities of these compounds were also evaluated in vitro.

Bioactive Limonoid Constituents of Munronia henryi.

Fourteen new limonoids, munronins A-N (1-14), and eight known limonoids (15-22) were isolated from the whole plants of Munronia henryi. The structures of the new compounds were elucidated by 2D NMR spectroscopy and mass spectrometry, and the structure of 8 was confirmed by single-crystal X-ray diffraction analysis. Compound 1 represents the first limonoid found with a novel 7-oxabicyclo[2.2.1]heptane moiety produced by incorporating C-11 and C-14 via an oxygen atom. All compounds were evaluated for their anti-tobacco mosaic virus (TMV) activity and in vitro cytotoxicity against the human cancer HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines. Among them, compounds 2, 8, 9, 10, 11, 12, 18, and 20 showed significant anti-TMV activity, with IC50 values in the range 19.6-44.4 µg/mL. Compounds 1 and 18 exhibited cytotoxic effects for all five cancer cell lines, with IC50 values between 0.4 and 4.8 µM.

Spiramine derivatives induce apoptosis of Bax(-/-)/Bak(-/-) cell and cancer cells.

Spiramine C-D, the atisine-type diterpenoid alkaloids isolated from the Chinese herbal medicine Spiraea japonica complex, are shown to have anti-inflammatory effects in vitro. In this study, we report that spiramine derivatives of spiramine C-D bearing α,ß-unsaturated ketone induce apoptosis of Bax(-/-)/Bak(-/-) MEFs cell, which is positively corresponding their cytotoxicity of tumor cell lines including multidrug resistance MCF-7/ADR. The results indicated that oxazolidine ring is necessary, and derivatives bearing double 'Michael reaction acceptor' group would significantly increased activities both of inducing apoptosis of Bax(-/-)/Bak(-/-) cells and cytotoxicity of tumor cells. The result indicated that spiramine derivative with α,ß-unsaturated ketone group is a new anti-cancer agent with a capability of inducing apoptosis of cancer cells in Bax/Bak-independent manner.

Limonoids from Aphanamixis polystachya and their antifeedant activity.

Eight new aphanamixoid-type aphanamixoids (C-J, 1-8) and six new prieurianin-type limonoids, aphanamixoids K-P (9-14), along with 10 known terpenoids were isolated from Aphanamixis polystachya, and their structures were established by spectroscopic data analysis. Among the new limonoids, 13 compounds exhibited antifeedant activity against the generalist Helicoverpa armigera, a plant-feeding insect, at various concentration levels. In particular, compounds 1, 4, and 5 showed potent activities with EC50 values of 0.017, 0.008, and 0.012 µmol/cm(2), respectively. On the basis of a preliminary structure-activity relationship analysis, some potential active sites in the aphanamixoid-type limonoid molecules are proposed.

Two new sphingolipids from the leaves of Piper betle L.

Two new sphingolipids, pipercerebrosides A (1) and B (2), were isolated from the leaves of Piper betle L. Their structures, including absolute configurations, were determined by spectroscopic analysis and chemical degradation. These two compounds did not show significant cytotoxic activity against the cancer cell lines K562 and HL-60 in a MTT assay.

A new Amaryllidaceae alkaloid from the bulbs of Lycoris radiata.

AIM: To study the Amaryllidaceae alkaloids of the bulbs of Lycoris radiata. METHODS: The chemical constituents were isolated and purified by various chromatographic techniques, and the chemical structures were elucidated on the basis of spectroscopic methods. In addition, the antiviral activities of alkaloids 1-10 were evaluated using flu virus A. RESULTS: One new homolycorine-type alkaloid 2α-methoxy-6-O-ethyloduline (1), together with nine known alkaloids 2α-methoxy-6-O-methyloduline (2), trispherine (3), 8-O-demethylhomolycorine (4), homolycorine (5), 9-O-demethylhomolycorine (6), oduline (7), lycorenine (8), 6α-O-methyllycorenine (9) and O-ethyllycorenine (10) were obtained. CONCLUSION: Alkaloid 1 is a new compound, and 1-3 were major alkaloids in this plant. Alkaloids 1-3 showed weak antiviral activities against flu virus A with IC50 values of 2.06, 0.69, and 2.71 µg·mL-1 and CC50 values of 14.37, 4.79, and 80.12 µg·mL-1, respectively.