Two new biflavonones from Coreopsis tinctoria.

Two new biflavonone compounds, sikokianin D (1) and sikokianin E (2), were isolated from the capitulum of Coreopsis tinctoria. The structures of these compounds were elucidated by spectroscopic techniques including NMR, HRESIMS and circular dichroism (CD).

Four new triterpenoid glycosides from the seed residue of Hippophae rhamnoides subsp. sinensis.

Four new triterpenoid saponins (1-4) were isolated from the seed residue of Hippophae rhamnoides subsp. sinensis, named 3-O-[ß-D-glucopyranosyl(1 → 2)-ß-D-glucopyranosyl-(1 → 3)]-[α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosyl-13-ene-19-one-28-oic acid 28-O-ß-D-glucopyranosyl ester (1), 3-O-[ß-D-glucopyranosyl(1 → 2)-ß-D-glucopyranosyl-(1 → 3)]-[α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosyl-13-ene-19-one-30-hydroxyolean-28-oic acid 28-O-ß-D-glucopyranosyl ester (2), 3-O-[ß-D-glucopyranosyl(1 → 2)-ß-D-glucopyranosyl-(1 → 3)]-[α-L-rhamnopyranosyl-(1 → 2)]-ß-D-glucopyranosyl-13-ene-19-one-28-oic acid 28-O-ß-D-glucopyranosyl ester (3), and 3-O-[ß-D-glucopyranosyl(1 → 2)-ß-D-glucopyranosyl-(1 → 3)]-[α-L-rhamnopyranosyl-(1 → 2)]-ß-D-glucopyranosyl-13-ene-19-one-30-hydroxyolean-28-oic acid 28-O-ß-D-glucopyranosyl ester (4), and their structures were elucidated on the basis of spectroscopic and chemical methods.

Studies on the flavone glycosides from Fructus Kochiae.

A series of flavone glycosides were isolated from Fructus Kochiae for the first time, including two new flavone glycosides. The structures were established by interpretation of their spectroscopic data. Two new flavone glycosides are quercetin 3-O-ß-d-apiofuranosyl-(1 â†’ 2)-ß-d-galactopyranosyl-7-O-ß-d-glucopyranoside (1) and quercetin 3-O-α-l-rhamnopyranosyl-(1 â†’ 6)-ß-d-galactopyranosyl-7-O-ß-d-sophoroside (2). The others are quercetin 7-O-ß-d-glucopyranoside (3), quercetin 3-O-ß-d-apiofuranosyl-(1 â†’ 2)-ß-d-galactopyranoside (4), quercetin 3-O-ß-d-galactopyranosyl-7-O-ß-d-glucopyranoside (5), and quercetin 7-O-ß-d-sophoroside (6).

Three new flavonoids, hippophins K-M, from the seed residue of Hippophae rhamnoides subsp. sinensis.

Three new flavonol glycosides (1-3), hippophins K-M, were isolated from the seed residue of Hippophae rhamnoides subsp. sinensis. The chemical structures of these three new compounds were identified by 1D, 2D NMR, mass spectroscopy and high resolution electrospray ionization mass spectrometry spectroscopic data and by comparison with the literature data. This report is a continuous research work on the systematic chemical investigation of plants of the genus Hippophae in our laboratory.

Hippophins C-F, four new flavonoids, acylated with one monoterpenic acid from the seed residue of Hippophae rhamnoides subsp. sinensis.

Four new flavonol glycosides (1-4), hippophins C-F, together with one known flavonoid (5), were isolated from the seed residue of Hippophae rhamnoides subsp. sinensis. The chemical structures of these compounds were characterized by 1D and 2D NMR, and HR-ESI-MS data. This report is a continuous research work on the systematic chemical investigation of plants of the genus Hippophae in our laboratory.

Depigmentation effect of kadsuralignan F on melan-a murine melanocytes and human skin equivalents.

The development of melanogenic inhibitors is important for the prevention of hyperpigmentation, and, recently, consideration has been given to natural materials or traditionally used ingredients such as Chinese medicine. The aim of this study is the evaluation of a new anti-melanogenic candidate, kadsuralignan F, from the natural plant Kadsura coccinea, as well as the determination of mechanisms of melanogenesis inhibition at a molecular level. Kadsuralignan F significantly reduced melanin synthesis in a dose-dependent manner in a murine melanocyte cell line and human skin equivalents. There was no direct inhibition on mushroom tyrosinase or cell-extract tyrosinase activity, and mRNA expression of tyrosinase and other melanogenic genes such as tyrosinase-related protein-1 (trp-1) or trp-2 were not affected by kadsuralignan F. Interestingly, the protein level of tyrosinase was dramatically downregulated with kadsuralignan F treatment. We found that a decrease of tyrosinase protein by kadsuralignan F was fully recovered by MG132, a proteasome inhibitor, but not by chloroquine, a lysosome inhibitor. In this study, we found that kadsuralignan F, a lignan from an extract of Kadsura coccinea, has an inhibitory activity on melanin synthesis through tyrosinase degradation. These findings suggest that kadsuralignan F can be used as an active ingredient for hyperpigmentation treatment.

Three new flavonoids from the seeds of Hippophae rhamnoides subsp. sinensis.

To study the chemical constituents of the seeds of Hippophae rhamnoides subsp. sinensis, three new flavonoids acylated with one monoterpenic acid, named 3-O-ß-D-glucosyl-kaempferol-7-O-{2-O-[2(E)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]}-α-L-rhamnoside (3), 3-O-ß-D-sophorosyl-kaempferol-7-O-{3-O-[2(E)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]}-α-L-rhamnoside (4), and 3-O-ß-D-sophorosyl-kaempferol-7-O-{2-O-[2(E)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]}-α-L-rhamnoside (5), together with four known compounds, were isolated from the seeds of H. rhamnoides subsp. sinensis. Compounds 1 and 2 are reported for the first time from this genus. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D and 2D NMR and HR-MS, and by comparison with literature data.

Three new flavonoid glycosides from Urena lobata.

Three new flavonoid glycosides, kaempferol-3-O-ß-D-apiofuranosyl(1 → 2)-ß-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (1), kaempferol-4'-O-ß-D-apiofuranosyl-3-O-ß-D-glucopyranosyl-7-O-α-l-rhamnopyranoside (2), and 5,6,7,4'-tetrahydroxy-flavone-6-O-ß-D-arabinopyranosyl-7-O-α-L-rhamnopyranoside (3), were isolated from the aerial parts of Urena lobata L., along with 10 known compounds (4-13). Their structures were determined based on spectroscopic methods including 1D and 2D NMR spectroscopy as well as HR-ESI-MS.

Miscellaneous terpenoid constituents of Abies nephrolepis and their moderate cytotoxic activities.

Three monoterpenoids and two triterpenoids were isolated from Abies nephrolepis together with 53 known terpenoids. The structures of the compounds were established by 1D and 2D NMR spectroscopy. The absolute configuration of 3-hydroxycamphane-2-carboxylic acid was established as (1S,2R,3S,4R) by Cu-Kα X-ray crystallography. All 58 isolates were tested for cytotoxic activity against four tumor cells viz. A549 (human lung adenocarcinoma), Colo205 (colon adenocarcinoma), QGY-7703 (human hepatoma) and THP-1 (human monocytic leukemia). α-Cadinol exhibited the best effects on A549, Colo205 and QGY-7703 with IC(50) values of 8.6, 8.1 and 4.6 µg/mL, respectively.

Two new dammarane monodesmosides from Centella asiatica.

Two new dammarane monodesmosides centellosides A (1) and B (2), and two new natural products ginsenosides Mc (10) and Y (11), together with 11 known compounds (3-9 and 12-15) reported for the first time from this genus, were isolated from the whole plants of Centella asiatica. All structures were elucidated by spectroscopic techniques and chemical methods, and compared with literature values. All the isolated compounds were evaluated in vitro for cytotoxicity.

Two new compounds from Urena lobata L.

Two new compounds 1 and 2 have been isolated from the aerial parts of Urena lobata L. The structures of the two new compounds were established as ceplignan-4-O-ß-d-glucoside (1) and 2,5-dihydroxy benzoic acid-7-(2,6-dimethyl-6-hydroxy-2,7-octadienoic acid) anhydride-5-O-ß-d-apiofuranosyl(1 â†’ 2)-ß-d-glucoside (urenoside A) (2), on the basis of chemical and spectral evidence, including 1D and 2D NMR spectroscopic data as well as mass spectrometry (HR-ESI-MS).

Pterosins from Pteris multifida.

A new C(14) pterosin sesquiterpenoid, named (2R)-pterosin P (1), and a new natural product, named dehydropterosin B (3), were isolated from the aerial parts of Pteris multifida Poir., along with nine known compounds (2, 4-11). By chiral HPLC, compounds 1 and 2 were isolated as a pair of enantiomeric pterosin sesquiterpenoids. The planar structure of 1 was elucidated on the basis of NMR spectroscopy analysis, and the absolute configuration was established by the CD spectrum. In addition, the absolute structure of 1 was further confirmed by single-crystal X-ray diffraction (CuK α). Compounds 3, 5, and 6 showed potent cytotoxicity against PANC-1 (human pancreatic cancer) and NCI-H446 (human small-cell lung cancer) cell lines, with IC(50) values in the range of 4.27-14.63 µM.

Antitumor activities of dammarane triterpene saponins from Bacopa monniera.

Bioassay-guided methods were used to test the antitumor activity of methanol extract of the whole plant of Bacopa monniera (L.) Wettst. and four different fractions (petroleum ether, CHCl(3), EtOAc, and n-BuOH fractions) of the methanol extract. Among the five crude samples, n-BuOH fraction was noted to have the highest antitumor activity. The dammarane triterpene saponins isolated from n-BuOH fraction, bacopaside E (1) and bacopaside VII (3), had potential antitumor effect. 1 and 3 showed cytotoxicity of all the tested human tumor cell lines MDA-MB-231, SHG-44, HCT-8, A-549 and PC-3M in MTT assay in vitro, and showed 90.52 % and 84.13 % inhibition in mouse implanted with sarcoma S180 in vivo at the concentration of 50 micromol/kg, respectively. The remaining two compounds, bacopaside II (2) and bacopasaponin C (4) were found to be much less potent compared with 1 and 3. 1 and 3 significantly inhibited human breast cancer cell line MDA-MB-231 adhesion, migration and Matrigel invasion in vitro at the concentration of 50 micromol/L. Since no antitumor activities about the monomers from Bacopa monniera (L.) Wettst. have been reported, these results indicate that the mechanism of action of 1 and 3 needs further study.

5 alpha-reductase and aromatase inhibitory constituents from Brassica rapa L. pollen.

In the screening of biologically active constituents from Brassica rapa pollen, the supercritical CO(2) fluid extract (SFE-CO(2)) showed potent 5 alpha-reductase and aromatase inhibiting activity. The SFE-CO(2) extract was separated by various chromatographic methods to give two new phytosterol derivatives, 24-methylenecholesterol linolenate (1) and cycloeucalenol linolenate (2), as well as eight known compounds, 24-methylenecholesterol palmitate (3), cycloeucalenol (4), pollinastanol (5), 24-methylenecholesterol (6), linolenic acid (7), palmitic acid (8), monolinolein (9) and monopalmitin (10), compounds 7 and 9 showed potent 5 alpha-reductase inhibitory activity; compounds 1-6 and 10 showed potent aromatase inhibitory activity.

Effect of triterpenoid saponins from Bacopa monniera on scopolamine-induced memory impairment in mice.

Three new saponins, bacopasides IX-XI (1- 3), together with their known analogues bacopaside I (4), bacopaside II (5), bacopasaponsin C (6), and bacopasaponsin D (7), were isolated from the whole plant of Bacopa monniera. Compounds 3, 4, and 6 showed nootropic activity when tested in the Morris water maze test and step-down test of scopolamine-induced memory impairment in mice.

[Influence of traditional Chinese compound recipes with different efficacy on body weight, tumor weight and immune function in H22 cancer-bearing mice].

OBJECTIVE: To compare the influence of traditional Chinese compound recipes (TCCRs) with different efficacy on body weight, tumor weight and immune function in H22 cancer-bearing mice. METHODS: H(22) cancer-bearing mice were chosen to observe the effects of TCCRs with different efficacy on tumor growth inhibition and detect the proliferation function of T lymphocytes, the activity of natural killer (NK) cells, the changes of T lymphocytes and the content of interferon-gamma (IFN-gamma)and interleukin-4 (IL-4). RESULTS: Tumor weight of H(22) cancer-bearing mice in Yidu Gongdu Recipe (YDGDR, a compound traditional Chinese herbal medicine using poison as an antidote for poison)-treated group was obviously lighter than that in the other TCCR-treated groups and the tumor inhibition rate in YDGDR-treated group was 65.76% (P<0.01). The tumor inhibition rates in other TCCR-treated groups were ranged from 10.1% to 17.1% . Body weight of mice in YDGDR-treated group was obviously decreased and depilation was observed at the same time. Pelage of mice in Fuzheng Peiben Recipe (FZPBR, a compound traditional Chinese herbal medicine for supporting the healthy energy)-treated group grew well, and behavior of the mice was active. Stimulation index (SI) of T lymphocyte transformation in YDGDR-treated group was obviously increased (SI=4.34, P<0.01), which showed the proliferation function of T lymphocyte was very strong. The SI of T lymphocyte transformation in the other groups was less than three, which showed the proliferation function of T lymphocytes was not significant. Compared with normal saline (NS)-treated group, percentages of NK cells in Qinre Jiedu Recipe (QRJDR, a compound traditional Chinese herbal medicine for clearing away heat and toxic substances)-treated, Huxue Huayu Recipe (HXHYR, a compound traditional Chinese herbal medicine for activating blood circulation to dissipate blood stasis)-treated and YDGDR-treated groups were obviously increased and 5.05, 4.07 and 5.17 times more than the NS-treated group, respectively (P<0.01). The activity of NK cells wasn't increased in the FZPBR-treated and HXHYR-treated groups. The production of IFN-gamma induced by T cells in YDGDR-treated group was obviously raised (P<0.05), and the production of IL-4 induced by T cells in QRJDR-treated, HXHYR-treated, Huatan Sanjie Recipe (a compound traditional Chinese herbal medicine for eliminating phlegm and resolving masses)-treated and YDGDR-treated groups was also raised obviously (P<0.01). CONCLUSION: YDGDR has a good effect of inhibiting tumor growth and can reinforce cellular and humoral immune function in tumor-bearing mice. FZPBR can strengthen the body.

[Tumor inhibiting and immunoloregulation effects of Mylabris Mixture on H22 cancer-bearing mice].

OBJECTIVE: To investigate the mechanisms of tumor inhibiting and immunoloregulation of Mylabris Mixture on H22 cancer-bearing mice. METHODS: H22 cancer-bearing mice were chosen to observe the effects of tumor inhibiting and detect the proliferation function of T lymphocytes, the toxicity function of NK cells, the changes of T lymphocytes and the contents of interferon-gamma and interleukin-4. RESULTS: Mylabris Mixture could obviously inhibit the growth of H22 cancer in mice, and the tumor inhibition rat was 65.76%. The stimulation index of T lymphocyte transformation and percentage of NK cells in Mylabris Mixture-treated group were obviously higher than those in the normal control group. The subpopulation proportion of T lymphocytes in Mylabris Mixture-treated group was changed more than the normal control group. The production of interferon-gamma and interleukin-4 by T lymphocytes obviously increased in Mylabris Mixture-treated group (P<0.05, P<0.001). CONCLUSION: Mylabris Mixture has the effect of inhibiting the growth of tumor constitution, and regulating immunological function on mice with tumor. Its mechanisms include the reinforcement of T lymphocyte immune function, NK cell killing function and humoral immune function.

[Structure identification of two new cerebrosides from Helicia nilagirica Beed].

AIM: To study the bioactive components from Helicia nilagirica. METHODS: Compounds were separated with a combination of multi-chromatography. Their chemical structures were determined on the basis of spectral analysis and chemical evidence. RESULTS: Two compounds were isolated from the leaves of Helicia nilagirica. Compound 1 was elucidated as 1-O-3-D-glucopyranosyl-(2S,3S,4R,8Z)-2-[(2'R)-2'-hyd roxylignocenoyl-amino]-8-octadecene-1, 3, 4-triol. Compound 2 was an analogue of 1. CONCLUSION: The two compounds are new cerebrosides.

[Identification of the structure of two new nitro group phenolic glycosides from Schisandra propinqua (Wall. ) Baill var. intermidia A. C. Smith].

AIM: To study the bioactive components from Schisandra propinqua (Wall.) Baill var. intermidia A. C. Smith. METHODS: Compounds were separated with a combination of multichromatography. Their chemical structures were determined on the basis of spectral analysis and chemical evidence. RESULTS: Seven compounds were isolated from the leaves of Helicia nilagirica. The structures were elucidated as 6'-O-alpha-L-arabinofuranosylthalictoside (1), 6'-O-beta-D-apiofuranosylthalictoside (2), thalictoside (3), icariside D2 (4), prinsepiol (5), (+)-1-hydroxypinoresinol (6) and (+)-medioresinol (7). CONCLUSION: Two compounds are new nitro phenolic glycosides.