Anti-neuroinflammatory constituents from Polygala tricornis Gagnep

Two new compounds (S)-(+)-butyl-4-methylene-5-oxo-pyrrolidin-2-carboxylate (1) and (5-formylfuran-2-yl)methyl 4-hydroxy-2-methylenebutanoate (2), together with four known compounds (3-6) were isolated from the roots of Polygala tricornis Gagnep. Their structures were determined on the basis of 1D- and 2D-NMR experiments and by comparison with physical data of known compounds. All the isolated compounds were examined for their inhibitory effect on the nitric oxide (NO) production induced by lipopolysaccharide (LPS) in BV-2 microglial cells, and compounds 1 and 2 exhibited pronounced inhibition on the NO production with IC(50) values of 14.1 μM and 1.77 μM, respectively.     

Antibacterial activity of tannin constituents from Phaseolus vulgaris, Fagoypyrum esculentum, Corylus avellana and Juglans nigra

Tannins were fractionated from acetonic extract preparations of phenolic compounds from Phaseolus vulgaris, Fagoypyrum esculentum, Corylus avellana and Juglans nigra. Wide variations in antibacterial activities ranging from MICs of 62.5 to 500 microg/ml were apparent. Of particular note was a relatively high level of activity (62.5 to 125 microg/ml) for all extracts against Listeria monocytogenes.     

Phenolics from Bidens bipinnata and their amylase inhibitory properties

A new chlorinated flavonoid, 3, 6, 8-trichloro-5, 7, 3', 4'-tetrahydroxyflavone (1), a new biscoumaric acid derivative, 4-O-(2″, 3″-O-diacetyl-6″-O-p-coumaroyl-β-d-glucopyranosyl)-p-coumaric acid (2), and 8, 3', 4'-trihydroxyflavone-7-O-β-d-glucopyranoside (3) together with twenty-four known compounds (4-27) were isolated from the whole plant of Bidens bipinnata. All chemical structures were established on the basis of UV-, MS- and NMR ((1)H, (13)C, (1)H-(1)H COSY, HMQC and HMBC) spectroscopic data. Some of the isolated compounds were tested for the inhibition of α-amylase. The result showed that isookanin (6) was a potent inhibitor of α-amylase (IC(50)=0.447mg/ml).     

Larvicidal and growth inhibition of the malaria vector Anopheles stephensi by triterpenes from Dysoxylum malabaricum and Dysoxylum beddomei

Secondary metabolites from Dysoxylum malabaricum and Dysoxylum beddomei were tested against mature and immature stage of the mosquito vector Anopheles stephensi under laboratory conditions. The triterpenes 3beta,24,25-trihydroxycycloartane and beddomeilactone from D. malabaricum and D. beddomei showed strong larvicidal, pupicidal and adulticidal activity. They also affected the reproductive potential of adults by acting as oviposition deterrents. The highest concentration tested (10 ppm) of both compounds evoked more than 90% mortality and oviposition deterrence.     

12个山茶属植物花的挥发性物质研究

应用顶空固相微萃取和气相色谱—质谱联用方法,对贵州、云南两省12种山茶属植物物种及类型花的挥发性物质及其相对含量进行分析.共分离鉴定出237种挥发性化合物,占总挥发性化合物种类的99.58％.主要包括醛类、酮类、醇类、酯类、萜烯类、烷烃类、酸类及其他类等8类化合物.以怒江山茶花的挥发物种类最多(88种),离蕊金花茶最少(41种).有51种化合物为12个物种及类型中的多数植物所共有.其中,100％共有的5种;90％共有的8种;80％共有的10种;70％共有的10种;50％共有的18种;50％以下共有的100种.有86种化合物为各物种所独有.归类分析表明,醇类比例最高,达29.87％;萜烯类次之,为27.79％;再次为酯类,为22.48％.化合物中相对含量第1为L-芳樟醇,相对含量达75.94％;第2为(Z)-3-己烯酯,为42.48％;第3为庚烷-2-酮,为31.67％;第4为(Z)-3-己烯-1-醇和(S)-2-庚醇,分别达23.79％和20.95％.     

The classical drug discovery approach to defining bioactive constituents of botanicals

In this review, several recently identified biologically active principles of selected botanical dietary supplement ingredients are described, and were isolated using classical phytochemical chromatographic methods, with various spectroscopic procedures used for their isolation and structure elucidation. A central component of such an approach is “activity-guided fractionation” to monitor the compound purification process. In vitro assays germane to cancer chemoprevention were used to facilitate the work performed. Bioactive compounds, including several new substances, were characterized from açai (Euterpe oleracea), baobab (Adansonia digitata), licorice (Glycyrrhiza glabra), mangosteen (Garcinia mangostana), and noni (Morinda citrifolia). Many of these compounds exhibited quite potent biological activity, but tended to be present in their plant of origin only at low concentration levels.     

Ent-trachyloban-19-oic acid isolated from Iostephane heterophylla as a promising antibacterial agent against Streptococcus mutans biofilms

From the roots of Iostephane heterophylla, six known compounds, namely, ent-trachyloban-19-oic acid (1), the mixture of ent-kaur-16-en-19-oic acid (2) and ent-beyer-15-en-19-oic acid (3), xanthorrhizol (4), 16α-hydroxy-ent-kaurane (5) and 16α-hydroxy-ent-kaur-11-en-19-oic acid (6) were isolated using a bioassay-guided fractionation method. The known compounds (1-6) were identified by comparison of their spectroscopic data with reported values in the literature. In an attempt to increase the resultant antimicrobial activity of 1 and 4, a series of reactions was performed on ent-trachyloban-19-oic acid (1) and xanthorrhizol (4), to obtain derivatives 1a, 1b, and 4a-4d. All the isolated compounds (1-6) and the derivatives 1a, 1b, and 4a-4d were evaluated for their antimicrobial activity against two oral pathogens, Streptococcus mutans and Porphyromonas gingivalis associated with caries and periodontal disease, respectively. Compounds 1, 1b, 2+3, 4 and 4d inhibited the growth of S. mutans with concentrations ranging from 4.1 μg/mL to 70.5 μg/mL. No significant activity was found on P. gingivalis except for 4 with an MIC of 6.8 μg/mL. The ability of 1, 1b, 2+3, 4 and 4d to inhibit biofilm formation by S. mutans was evaluated. It was found that 1, 1b, 4 and 4d interfered with the establishment of S. mutans biofilms, inhibiting their development at 32.5, 125.0, 14.1 and 24.4 μg/mL, respectively.     

Two new nortriterpenoid saponins from Salicornia bigelovii Torr. and their cytotoxic activity

Investigation of characteristic constituents of Salicornia bigelovii Torr. led to isolation of two new 30-nortriterpenoid glycosides, Bigelovii A (1), Bigelovii B (2), together with two known 30-nortriterpenoid glycosides 3-4 and three known oleanane-type triterpenoid glycosides 5-7. The structures of new compounds were elucidated by extensive 1D and 2D NMR, and MS spectroscopic analysis, and chemical evidences. All compounds were isolated for the first time from Chenopodiaceae. Thus compounds 1-4 were evaluated for their cytotoxicity and compouds 1, 3 showed moderate activity against four cell lines, HL-60 (promyelocytic leukemia), MCF-7 (breast carcinoma), HepG2 (liver carcinoma) and A549 (lung carcinoma), with IC(50) values of 6.18, 78.08, 13.64 and >100μM for 1; 31.87, >100, ~100, >100μM for 3, respectively.     

Heptaketides with antiviral activity from three endolichenic fungal strains Nigrospora sp., Alternaria sp. and Phialophora sp

Two new heptaketides, (+)-(2S,3S,4aS)-altenuene (1a) and (-)-(2S,3S,4aR)-isoaltenuene (2a), together with six known compounds, (-)-(2R,3R,4aR)-altenuene (1b), (+)-(2R,3R,4aS)-isoaltenuene (2b), 5'-methoxy-6-methyl-biphenyl-3,4,3'-triol (3), alternariol (4), alternariol-9-methyl ether (5), and 4-hydroxyalternariol-9-methyl ether (6) were isolated from the EtOAc extract of an endolichenic fungal strain Nigrospora sphaerica (No.83-1-1-2). Compounds 1a and 1b were separated from enantiomers 1 by chiral HPLC, and so were 2a and 2b from enantiomers 2. Interestingly, 1-6 were also obtained from other two endolichenic fungal strains Alternaria alternata (No.58-8-4-1) and Phialophora sp. (No.96-1-8-1). The structures of 1-6 were elucidated by means of MS, HR-MS, NMR, and X-ray diffraction. Furthermore, the absolute configurations of 1a-2b were determined by CD experiments and CD calculation. Of these compounds, 4 and 5 showed antiviral activity against herpes simplex virus (HSV) in vitro, with IC(50) values of 13.5 and 21.3 μM, and with selective index (SI) values of 26.5 and 17.1, respectively.     

Norditerpenoids from Salvia castanea Diels f. pubescens

Three new norditerpenoids, castanol A-C (1-3), along with eighteen known diterpenoids, were isolated from Salvia castanea Diels f. pubescens. Their structures were elucidated by extensive spectroscopic analysis. All compounds were evaluated for their cytotoxic activities against five human cancer cell lines. The known compounds neo-tanshinlactone (12) and methyltanshinoate (17) exhibited significant cytotoxic activities against some cells.     

Asterosaponins from the starfish Culcita novaeguineae and their bioactivities

Bioassay-guided fractionation of the n-BuOH extract of the starfish Culcita novaeguineae resulted in the isolation of one new sulfated steroidal glycoside (asterosaponin) (1), along with three known asterosaponins, thornasteroside A (2), marthasteroside A(1) (3) and regularoside A (4), as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. Their structures were elucidated by extensive spectral studies and chemical evidences. All the saponins showed moderate cytotoxicity against cancer cell lines K-562 and BEL-7402.     

Three new antibacterial active diarylheptanoids from Alpinia officinarum

Three new diarylheptanoids, together with ten known ones, were isolated from the ethanol extract from the rhizomes of Alpinia officinarum Hance. The structural identification of these compounds was mainly achieved by spectroscopic methods. The new compounds were elucidated as 7-(4″, 5″-dihydroxy-3″-methoxyphenyl)-1-phenyl -4-heptene-3-one (1), 1, 7-diphenyl-5-heptene-3-one (2) and 4-phenethyl-1, 7-diphenyl -1-heptene-3, 5-dione (3), respectively. All of the compounds showed antibacterial activity against Helicobactor pylori. Especially, the three new compounds showed strong antibacterial activity against Hp-Sydney strain 1 with the MIC values of 9–12 μg/mL, and against Hp-F44 with the MIC values of 25–30 μg/mL.     

Four new neolignans from the leaves of Tripterygium wilfordii

Four new neolignans, wilfordiols A-D (1-4), together with five known compounds (5-9), were isolated from an aqueous extract of the dried leaves of Tripterygium wilfordii. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRESIMS, and CD experiments. The anti-inflammation activities of compounds 1-9 were evaluated by the inhibitory effect on NO production, in vitro.     

Aromatic compounds from endophytic fungus Colletotrichum sp. L10 of Cephalotaxus hainanensis Li

Six aromatic compounds were isolated from the endophytic fungus Colletotrichum sp. of Cephalotaxus hainanensis Li [Cephalotaxus mannii Hook. f.]. Their structures were determined on the basis of chemical and spectroscopic methods. The compound 2 was the enantiomer of compound 1. The compound 4 was the epimeride of the compound 3. The compounds 1, 2, 4 and 5 were evaluated for cytostatic activity against HL-60 and PC-3 cells.     

Anti-HBV activities of Streblus asper and constituents of its roots

The extracts from leaves, heartwood, barks and roots of the Streblus asper were investigated for anti-HBV activities, separately. The results suggested that the MeOH extracts of the heartwood, barks, and roots exhibited good anti-HBV activities. Further investigations displayed that ethyl acetate and n-butanol soluble parts of their MeOH extracts showed more significant anti-HBV activities. Moreover, a new lignan, together with 11 known compounds, was isolated from n-butanol-soluble part of MeOH extract of the roots of S. asper. The structures were elucidated by spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC) and HR-EI-MS experiments. Compounds 1-3 were evaluated for their anti-HBV activities. Honokiol showed significant anti-HBV activity with IC(50) values of 3.14μM and 4.74μM for HBsAg and HBeAg with no cytotoxicity respectively, while lamivudine (3TC, positive control) exhibited weak anti-HBV activity with IC(50) values of 11.81μM and 25.80μM for HBsAg and HBeAg respectively.     

Three new water-soluble alkaloids from the leaves of Suregada glomerulata (Blume) Baill

Three new water-soluble alkaloids (1-3) together with twelve known compounds (4-15) have been isolated from the water extract of leaves of Suregada glomerulata. Their structures were determined by spectroscopic analysis and chemical method. Compounds 1-3 were evaluated for their in vitro inhibitory activity against α-glucosidase and HIV-1 replication. However, no significant activities were found.     

Molluscicidal activity of Aglaia duperreana and the constituents of its twigs and leaves

The methanol (MeOH) extract of the twigs and leaves of Aglaia duperreana was investigated for its molluscicidal activity against Pomacea canaliculata. The extract was found to exhibit significant molluscicidal activity. The ethyl acetate soluble fraction of the extract showed the most potent molluscicidal activity among different solvent fractions. The bioactivity-guided chemical investigation of the ethyl acetate soluble fraction led to a new triterpenoid along with 15 known compounds. Their structures were elucidated by spectroscopic methods, including one- and two-dimensional nuclear magnetic resonance techniques as well as mass spectroscopic analysis. The molluscicidal activities of compounds 2-16 against P. canaliculata were also investigated. Naringenin trimethyl ether showed significant molluscicidal activity with a median lethal concentration (LC(50)) of 3.9 μg/mL, which was indicated higher potency than the positive control, tea saponin (LC(50)=4.5 μg/mL).     

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.     

In vitro antifungal activities of longan (Dimocarpus longan Lour.) seed extract

Longan, Dimocarpus longan Lour., contains polyphenolic compounds which exhibit several pharmacological properties. This study aims to evaluate antifungal activities of longan fruit extract in comparison to its active compounds. The results showed that longan seed exhibited antifungal activity against the opportunistic yeasts (Candida species and Cryptococcus neoformans). In contrast, longan pulp and whole fruit did not demonstrate any inhibitory effects. Ellagic acid showed the most potent antifungal activity followed by corilagin and gallic acid, respectively. Ellagic acid inhibited Candida parapsilosis and C. neoformans more effectively than Candida krusei and also some Candida albicans clinical strains. Baidam cultivar possessed higher antifungal activity (MIC=500-4000 μg/ml) as it contained higher contents of ellagic acid and gallic acid than Edor (MIC=1000-8000 μg/ml). For antibacterial activity, only corilagin and gallic acid possessed weak to moderate inhibitory effects against Staphylococcus aureus and Streptococcus mutans, respectively. Longan seed was then applied in the oral care products. Longan effervescent granule (5% extract) significantly reduced adhesion of C. albicans to acrylic strips. Mouthwash containing 0.5% extract exhibited good antifungal activity compared to a commercial product. These findings indicated that longan seed extract and its polyphenolic compounds can be used as an antifungal agent in oral care products for the treatment of opportunistic yeast infection.     

Diarylheptanoids from the rhizomes of Alpinia officinarum and their anticancer activity

Two new diarylheptanoids (1, 2), together with two known analogs (3, 4), were isolated from the rhizomes of Alpinia officinarum. The new compounds were elucidated to be (5S)-5-hydroxy-7-(3, 4-dihydroxyphenyl)-1-phenyl-3-heptanone (1) and (5R)-5-hydroxy-7-(3-methoxy-4, 5-dihydroxyphenyl)-1-phenyl-3-heptanone (2) based on their spectral analysis. Compound 4 showed moderate cytotoxicity against human tumor cell lines, HepG2, MCF-7 and SF-268, while no significant effect were found for compounds 1-3.