Two novel nortriterpenoids, cyclopalitins A and B (1 and 2), were isolated from aerial parts of Cyclocarya paliurus. Their structures were elucidated on the basis of extensive spectroscopic analyses including high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D NMR and 2D NMR. Compounds 1 and 2 were tested for their cytotoxicity towards B16F10. The results revealed that they didn't show cytotoxic activity against B16F10 with 10 ug/mL treatment for 48 h.
目的 研究中药枳壳(Citrus aurantium L.)的化学成分.方法 采用甲醇提取,应用现代色谱技术分离纯化,依据化合物理化性质和光谱数据鉴定化合物结构.结果 从中药枳壳体积分数95%甲醇提取物中分离鉴定了16个化合物,分别为:pyrrolezanthine.6-methyl ether(1),3-羟基-4-甲氧基苯甲酸甲酯(2),3-羟基-4-甲氧基苯甲酸(3),3,4-二羟基苯甲酸甲酯(4),3-(4-乙酰氧基苯基)丙酸酯(5),对羟基苯甲酸(6),7-羟基-6-甲氧基香豆素(7),5-羟甲基呋喃-2-甲醛(8),橙皮苷(9),柚皮苷(1O),gossypetin-8,3’-dimethylether-3-O-β-D-galactosid(11),2-homoeriodictyol-7-O-β-D-glucopyranoside(12),6-去甲氧基桔皮素(13),柚皮素(14),红橘素(15)和5-O-去甲基川陈皮素(16).结论 化合物1、2、4、8、11~13均为首次从该属植物中分离得到.
Phytochemical study of the ethanol extract of stems and leaves of Cyclocarya paliurus (Batal.) Iljinsk (Juglandaceae) led to the isolation of 22 compounds, including seventeen triterpenes (1–17), two sterides (18,19), one straight chain diterpene (20) and two naphthoquinones (21,22). The structures of all isolated compounds were identifed by extensive spectroscopic analyses including NMR, MS, and by comparison with the related literature. These compounds have shown the relationship between this plant and other species from the Juglandaceae family.
The present study carried out a phytochemical investigation of the methanol extract of the branches and leaves of Clausena lansium and afforded nine carbazole alkaloids (compounds 1-9) including two new carbazole alkaloids, claulansiums A and B (compounds 1 and 2). The new compounds were elucidated on the basis of extensive spectroscopic data (MS, NMR, IR, and UV) and the known compounds were identified by comparing spectroscopic data with those reported in literature. All the isolated compounds were tested for their cytotoxic activity against A549 and Hela cancer cell lines. Our results showed that compounds 2-6 exhibited varying degrees of cytotoxicity to cancer cells, with IC50 values ranging from 8.67 to 98.89 μmol·L-1.
The extraction, fractionation and recognition of flavonoids from the ethanolic extract of young twigs and leaves of C. bonduc were carried out. In addition, cytotoxic study of the flavonoids on two cancer cell lines, BGC-823 and HeLa was carried our using sulphorhodamine B assay. Seven flavonoids, six of which are being reported for the first time in this plant, were isolated. Their structures were identified by MS and NMR spectroscopic methods. Petroleum ether, ethyl acetate and water fractions exhibited moderate cytotoxic activity against HeLa cells. Five compounds showed cytotoxic activity against HeLa cell in comparison with Paclitaxel, while only one compound showed a good degree of cytotoxic activity against BGC-823 cell in comparison to Paclitaxel. The results obtained showed a structure - activity relationship.
Five flavone C-glycosides were isolated from the methanol extract of the degrease seeds of Ziziphus jujuba var. spinosa though various column chromatography methods including silica gel, MPLC, and HPLC. The structures were elucidated as 6"-feruloyl- 6'''-vanillylspinosin(1), 6",6'"-diferuloylspinosin(2), spinosin(3), swertisin(4) and isoswertisin(5) based on the NMR and MS spectral data. 1 is a new compound.
A new prenylated xanthone, butyraxanthone F (1) together with 20 known compounds were isolated from the leaves of Pentadesma butyracea. Their identification was achieved by spectroscopic means and comparison of the data with literature or by direct comparison on TLC with authentic samples. To the best of our knowledge, this is the first report of 2-hydroxy-2,3-dihydrosqualene (17) from a natural source. Compounds 2–6 and 11–16 were found for the first time in this genus. The antiproliferative activity of the crude extract, fractions and some isolated compounds was evaluated against three human cancer cell lines, BGC-823, Hela and A549. The crude extract, fractions B and C showed weak activities. Globuxanthone (2) and 30-epi-cambogin (7) were found to be the most active compounds on the three cancer cells. The effect of 2 on Hela cells and that of 7 on BGC-823 cells were noteworthy. The antiproliferative potential of allanxanthone A (3), ergosta-4,6,8(14),22-tetraen-3-one (14) and 2-hydroxy-2,3-dihydrosqualene (17) against BGC-823 and Hela cells could be classified as moderate-to-weak.
AbstractThree novel nortriterpenes (I)—(III) with a unique A‐nor‐E‐seco spiro‐lactone ceanothane‐type triterpene skeleton are isolated from the roots of Ziziphus mauritiana together with three known triterpenes.
Two new coumarins, clauexcavatins A (1) and B (2), along with seven known ones (3-9), were isolated from the roots of Clausena excavata Burm. f. (Rutaceae). Their structures were elucidated on the basis of spectral data.
Plant cyclopeptides,cyclic compounds formed mainly by the peptidic bonds of 2-37 protein and non-protein amino acids(mainly Z-amino acids) and found in higher plants,have been attractive for their extensive bioactivities and distinctive molecular architectures.During the last half century's study...
Plant cyclopeptides, cyclic compounds formed mainly by the peptidic bonds of 237 protein and non-protein amino acids (mainly L-amino acids) and found in higher plants, have been attractive for their extensive bioactivities and distinctive molecular architectures. During the last half century's study, about 500 cyclopeptides divided into eight types have been isolated from over 120 species, which belong to over 20 families and 60 genera. Some cyclopeptides showed potential anti-tumor, sedative, immunosuppressive, and uterotonic activities. In the Chinese Pharmacopoeia (CP, 2010 Version), 23 species (14 families, 18 genera) containing cyclopeptides have been recorded in the origins of 24 traditional Chinese medicines (TCMs). Heterophyllin B (64), first reported by us from Pseudostellaria heterophylla in 1993 was cited for the first time in CP as the standard substance of cyclopeptides for quality control. In this review, we highlight the progress in the chemical studies of these cyclopeptide-containing TCMs, in particular recent results in our group's publications.
Chemical constituents in ethyl acetate and butanol fractions of ethanol extracts from Acorus tatarinowii were separated by column chromatography. Bufo skeletal muscle fatigue model was established to study the anti-fatigue activity of separated compounds. Five compounds were separated and identified by spectroscopic analysis as acoramone(1),cycloartenone(2),2,4,5-trimethoxyl-2'-butoxy-1,2-phenyl propandiol(3),5-hydroxymethyl furfural(4), and 5-butoxymethyl furfural(5). Compound 3 was a new compound, and compounds 2 and 5 were separated from this plant for the first time. Compound 4 exhibited a notable anti-fatigue activity.
Labdane diterpene glycosides cathargyroside A and cathargyroside B, monoterpene glycosides vervenone-10-O-β-d-glucopyranoside and vervenone-10-O-β-d-apiofuranosyl-(1″→6′)-β-d-glucopyranoside, as well as lignan glycosides cedrusinin-4-O-α-l-rhamnopyranoside and (+)-cyclo-olivil-9′-O-β-d-xylopyranoside, along with 39 known compounds, were obtained from the methanol extract of the twigs and leaves of Cathaya argyrophylla. These compounds were identified mainly by analyzing their NMR and MS data. Almost all of these compounds were hitherto unknown in this genus. The isolated compounds were screened against Candida albicans and Staphylococcus aureus for antimicrobial assay, and against K562, HT-29, BEL-7402, SGC-7901, B16, BGC-823, U251 and A549 cancer cell lines for cytotoxic activities. One compound showed antimicrobial activity against C. albicans, and four of them displayed cytotoxicity. Similarity analysis on the chemical constituents of the genera Cathaya, Picea and Pinus supported their close phylogenetic relationships.
Zizimauritic acids A–C (1–3), three novel nortriterpenes with a unique A-nor-E-seco spiro-lactone ceanothane-type triterpene skeleton, together with 3 known triterpenes ceanothenic acid (4), betulinic acid (5), and ceanothic acid (6), were isolated from the roots of Ziziphus mauritiana. Compounds 1–4 showed cytotoxicities with the IC50 values ranging from 5.05 to 11.94μg/ml, and compounds 1 and 3 showed an inhibitory effect on the growth of Staphylococcus aureus with the IC50 values 2.17 and 12.79μg/ml. A plausible biosynthetic pathway of compounds 1-3 was proposed.
Sixteen eudesmane-type sesquiterpenes including seven new compounds oxyphyllanene A-G (1-2 and 5-9) were isolated from the fruits of Alpinia oxyphylla. Among them, compounds 1-2 are novel trinoreudesmane sesquiterpenes, and 5 is a noreudesmane one. Their structures were established by spectroscopic analysis, including 2D-NMR techniques. Inhibitory activity of compounds 3-8 and 10-16 were tested against nitric oxide production in LPS and IFN-γ-induced RAW 264.7 murine macrophages, and their IC(50) values ranged from 9.85 to 13.95 μg/ml.
Bigelovin is a sesquiterpene lactone isolated from the plant Inula helianthus-aquatica which was traditionally used in cancer treatment in Yunnan, China. The potent apoptotic activities of bigelovin in human leukemia U937 cells were shown in our previous study. The present study investigated the anti-angiogenic and immunomodulatory effects of bigelovin using transgenic zebrafish Tg(fli1a:EGFP)y1 with fluorescent blood vessels and human peripheral blood mononuclear cells (PBMCs), respectively. Furthermore, the inhibitory activities of bigelovin on the human endothelial cell adhesion molecules (CAMs) were also examined. Our results showed that the growth of subintestinal vessels of the bigelovin-treated zebrafish embryos was significantly inhibited and the gene expressions in angiogenesis signaling pathways (e.g. Ang2 and Tie2) of the zebrafish were down-regulated after bigelovin treatment. Besides, the proliferation and Th1 cytokines productions (e.g. IFN-γ, IL-2 and IL-12) were suppressed in bigelovin-treated PBMCs. On the other hand, bigelovin was shown to significantly inhibit the human monocyte adhesion to human endothelial cells and the gene expressions of inflammation-related CAMs (e.g. ICAM-1, VCAM-1 and E-selectin) were significantly down-regulated in bigelovin-treated human endothelial cells. In summary, our data provide the first evidence that bigelovin possesses anti-angiogenic and immunomodulatory activities, suggesting bigelovin may exert multi-target functions against cancer in animal models.
AbstractThree new benzoic acid allopyranosides (I) and four new lignan glycosides (II)—(IV) are isolated along with five known compounds from the twigs of the Chinese conifer mentioned above.
Twelve new arborinane-type triterpenoids (1-12) and four new anthraquinones (13-16), together with 50 known compounds, were isolated from the roots of Rubia yunnanensis. The structures of 1-16 were elucidated by spectroscopic data analysis and chemical methods. All compounds were evaluated for their cytotoxic, antibacterial, and antifungal activities. Rubiyunnanol C (5) is the first example of an arborinane-type triterpenoid with a double bond at C-8-C-9.
OBJECTIVETo study the chemical constituents of the whole plants of Pedicularis densispica.METHODThe chemical constituents were isolated by various chromatographic methods and their structures were determined by chemical evidences and spectral data.RESULTTen compounds were isolated and identified as acacetin (1), apigenin-7-0-beta-glucopyranoside (2), kaempferol-3,7-O-alpha-dirhamnopyranoside (3), scutellarein-7-0-beta-glucopyranoside (4), chrysoeriol-7-O-beta-glucopyranoside (5), pedicutricone A (6), dearabinosyl pneumonanthoside (7), salidroside (8), darendoside B (9), and maltol-beta-D-glucopyranoside (10).CONCLUSIONThese compounds were isolated from the titled plant for the first time. Except compounds 6 and 8, the others were obtained for the first time from the genus Pedicularis.
AbstractShionane‐type triterpenes (I) and (II) are isolated from the title herb which is used in traditional Chinese medicine for the treatment of cough.