[Chemical constituents from fruits of Morinda citrifolia and their inhibitory effects on proliferation of synoviocytes in vitro].

The chemical constituents from the fruits of Morinda citrifolia were systematically explored by chromatographic fractionation methods including silica gel, octadecylsilyl(ODS) gel, Sephadex LH-20 gel, and preparative high performance liquid chromatography(pre-HPLC). The chemical structures of all isolated compounds were identified on the basis of their physicochemical properties, spectroscopic analyses, as well as the comparisons of their physicochemical and spectroscopic data with the reported data in literature. As a result, 22 isolated compounds from the 90% ethanol extract of the fruits of M. citrifolia were identified, which were moricitritone(1), 2'-deoxythymidine(2), cyclo-(L-Pro-L-Tyr)(3), methyl-5-hydroxy-2-pyridinecarboxylate(4), methyl pyroglutamate(5), bisbenzopyran(6), epipinoresinol(7), 3, 3'-bisdemethyl pinoresinol(8), 3, 3'-bisdemethyltanegool(9), trimesic acid(10), crypticin B(11), kojic acid(12), vanillic acid(13), protocatechoic acid(14), 5-hydroxymethyl furfural(15), blumenol A(16), 1-O-(9Z, 12Z-octadecadienoyl) glycerol(17), mucic acid dimethylester(18), methyl 2-O-ß-D-glucopyranosylbenzoate(19), 2-phenylethyl-O-ß-D-glucoside(20), scopoletin(21), and quercetin(22). Among them, compound 1 was a new pyrone derivative, compounds 2, 4-7, 10-12, and 17 were isolated from the plants belonging to Morinda genus for the first time, and compound 18 was obtained from M. citrifolia for the first time. Moreover, on the basis of testing the activities of all isolated compounds on inhibiting the proliferation of synovial fibroblasts in vitro by MTS assay, the anti-rheumatoid arthritis activities of all isolated compounds were initially evaluated. The results showed that compounds 1-6, 9, 19, and 20 exhibited remarkable anti-rheumatoid arthritis activities, which displayed the inhibitory effects on the proliferation of MH7A synovial fibroblast cells with the IC_(50) values in the range of(3.69±0.08) to(168.96±0.98) µmol·L~(-1).

Syzysamalactone, an Unusual 11-Carbon δ-Lactone Derivative from the Fresh Ripe Fruits of Syzygium samarangense (Wax Apple).

To study the chemical constituents from the ripe fresh fruits of Syzygium samarangense (wax apple) and their potential health effects, a phytochemical investigation was undertaken. A new δ-lactone derivative, syzysamalactone (1), along with a known biogenetically related δ-lactone derivative, 6-pentyl-α-pyrone (2), were isolated from the fresh ripe fruits of S. samarangense. Syzysamalactone (1) is an unusual 11-carbon δ-lactone derivative, and its chemical structure and absolute configuration were elucidated by spectroscopic data analysis. A plausible biogenetic pathway for 1 was also proposed. Furthermore, the potential neuroprotective effects of compounds 1 and 2 were assessed. As a result, compounds 1 and 2 displayed notable neuroprotective effects with EC50 values of 0.29 ± 0.03 and 1.28 ± 0.06 µM, respectively, using the SH-SY5Y human neuroblastoma cell line. This is the first report of δ-lactone derivatives showing significant neuroprotective activities.

[Chemical constituents from Artocarpus incisus and their inhibitory effects on proliferation of synoviocytes in vitro].

The chemical constituents from the branches and leaves of Artocarpus incisus were isolated and purified via silica gel, ODS, and Sephadex LH-20 column chromatography as well as preparative HPLC. The chemical structures of all isolated compounds were identified in the light of their physicochemical properties, spectroscopic analyses, and comparisons of their physicochemical and spectroscopic data with the reported data in literature. As a result, 20 compounds were isolated and characterized from the 90% ethanol extract of the branches and leaves of A. incisus, which were identified as tephrosin(1), 6-hydroxy-6 a, 12 a-dehydrodeguelin(2), sarcolobin(3), lupiwighteone(4), 12-deoxo-12α-methoxyelliptone(5), 6 aα,12 aα-12 a-hydroxyelliptone(6), homopterocarpin(7), 3-hydroxy-8,9-dimethoxypterocarpan(8), pterocarpin(9), maackiain(10), medicarpin(11), calycosin(12), genistein(13), formononetin(14), 5-hydroxy-4',7-dimethoxy isoflavone(15), liquiritigenin(16), 4(15)-eudesmene-1ß,7α-diol(17), ent-4(15)-eudesmene-1ß,6α-diol(18), 1α-hydroxyisodauc-4-en-15-al(19), and guaianediol(20). Except compounds 13 and 16, all other compounds were isolated from the Artocarpus plants for the first time. Additionally, using MTS assay, compounds 1-20 were eva-luated for their anti-rheumatoid arthritis activities by measuring their anti-proliferative effects on synoviocytes in vitro. As a consequence, compounds 1-16 showed notable anti-rheumatoid arthritis activities, which displayed inhibitory effects on the proliferation of MH7 A synovial fibroblast cells, with the IC_(50) values in range of(9.86±0.09)-(218.07±1.96) µmol·L~(-1).

Clausanisumine, a Prenylated Bicarbazole Alkaloid from the Fruits of Clausena anisum-olens and Its Potential Anti-HIV Activity.

A unique prenylated bicarbazole alkaloid, clausanisumine (1), and two biogenetically related known monomer carbazole alkaloids, mukonal (2) and 3-methylcarbazole (3), were isolated from the fruits of Clausena anisum-olens. Clausanisumine (1) was an uncommon prenylated bicarbazole alkaloid, possessing an unprecedented carbon skeleton, which was composed of a simple carbazole alkaloid and a prenylated carbazole alkaloid. The chemical structure of 1 was established by a combination of comprehensive spectral methods. A plausible biosynthetic pathway of 1 was also proposed. Additionally, the potential anti-HIV activities of all isolates 1-3 in vitro were evaluated. Compound 1 exhibited remarkable anti-HIV-1 reverse transcriptase effects showing an EC50 value of 18.58 nM. The discovery of the prenylated bicarbazole alkaloid from C. anisum-olens with notable anti-HIV activity would be meaningful to discovering and developing new anti-HIV drugs.

Artapilosines A and B, Unusual Phenanthrene Derivatives Related to Aporphine Alkaloids from Artabotrys pilosus.

Two unusual phenanthrene derivatives related to aporphine alkaloids, artapilosines A (1) and B (2), as well as two biogenetically related known aporphine alkaloids, (-)-anonaine (3) and (-)-N-acetylanonaine (4), were separated and purified from Artabotrys pilosus. Artapilosine A (1) is the first compound representative of a new class of phenanthrene derivatives having an unprecedented carbon skeleton, in which the six-membered nitrogen-containing heterocyclic structure in a typical aporphine alkaloid was substituted with a unique five-membered carbocyclic ring. This is the first report of the formation of a carbon-carbon bond between C-5 and C-6a in 1 with the loss of the nitrogen atom N-6 in the classic aporphine alkaloid. Artapilosine B (2) is a novel phenanthrene derivative having a hydroxyethyl as a substituent on the phenanthrene ring. Their chemical structures as well as absolute configurations were determined based on analysis of spectroscopic data. Additionally, the potential anti-HIV activities of all isolates 1-4 were appraised. Artapilosines A (1) and B (2) showed notable anti-HIV reverse transcriptase affects, with EC50 values of 20.93 and 125.29 nM, respectively. These results suggested that the discovery of these novel phenanthrene derivatives from A. pilosus with remarkable anti-HIV effects could be essentially important for the researching and developing of new anti-HIV agents.

Anthraquinones with potential antiproliferative activities from the fruits of Morinda citrifolia.

The phytochemical investigation on the fruits of Morinda citrifolia led to the isolation and characterization of a new anthraquinone, moricitrifone (1), along with seven known anthraquinones (2-8). The chemical structure of 1 was elucidated by extensive spectral analyses. The known compounds (2-8) were identified by comparing their spectral data with those reported in the literature. The antiproliferative activities of all isolated anthraquinones (1-8) against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 were evaluated in vitro. Compounds 1-8 exhibited remarkable antiproliferative activities with IC50 values ranging from 0.26 ± 0.05 to 16.58 ± 0.18 µM, which were comparable to those of doxorubicin.