Secondary metabolites, cytotoxic response by neutral red retention and protective effect against H2O2 induced cytotoxicity of Sedum caespitosum

The EtOAc, n-BuOH and H20 subextracts of the crude MeOH extract of the aerial parts of Sedum caespitosum (cav.) Dc. were screened for cytotoxicity using the neutral red assay in Chinese hamster ovary cells as well as their protective effect against H2O2 induced cytotoxicity in human red blood cells. While the extracts did not show cytotoxicity, they displayed a protective effect compared to a blank and ascorbic acid. Gallic acid (1), kaempferol 3-O-alpha-rhamnopyranoside (2), quercetin 3-O-beta-glucopyranoside (3), quercetin 3-O-alpha-rhamnopyranoside (4) and myricetin 3-O-alpha-rhamnopyranoside (5) were isolated from the EtOAc extract and identified by 1D- and 2D-NMR. The protective effects of the isolated compounds against H2O2 induced cytotoxicity in human red blood cells were evaluated and 5 was the most active.     

Biological activities of phenolic compounds isolated from galls of Terminalia chebula Retz. (Combretaceae)

The aqueous extract of galls from Terminalia chebula Retz. (Combretaceae) was fractionated on Diaion and refractionated on octadecyl silica column. Six phenolic compounds were isolated and identified as gallic acid (1), punicalagin (2), isoterchebulin (3), 1,3,6-tri-O-galloyl-β-D-glucopyranose (4), chebulagic acid (5) and chebulinic acid (6). All of the compounds showed stronger 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and melanin inhibitory activities than ascorbic acid, butylated hydroxytoluene, α-tocopherol, arbutin and kojic acid, the reference compounds. Gallic acid (1) exhibited inhibitory activity against nitric oxide production in lipopolysaccharide-activated macrophages. However, all isolated compounds exhibited less activity than the reference compounds in mushroom tyrosinase inhibition and human tumour cytotoxicity assays. This study has demonstrated that the phenolic compounds isolated from galls of T. chebula might contribute significantly due to their antioxidant and whitening activities.     

大叶鱼骨木茎的化学成分研究

Chemical constituents of the stems of Canthium simile were studied.Seven compounds were isolated from ethyl acetate extract of the stem,and their structures were elucidated by various spectroscopic methods.They were identified as syringic acid (Ⅰ),isovanillic acid (Ⅱ),Caruilignan D (Ⅲ),(3β)-28-Norlup-20(29)-ene-3,17-diol(Ⅳ),3,4-dimethoxy-2,4-hexadienedioic acid (Ⅴ),dibutyl phthalate (Ⅵ) and diisobutyl phthalate(Ⅶ).The seven compounds were isolated from this genus for the first time.     

Constituents of Salvia microphylla

A new phenolic ester 2-( p-hydroxyphenyl)ethyl eicosaheptanoic acid ester (1) and a known one hexacosylferulate (2) were isolated from the acetone extract of Salvia microphylla. In addition, two sesquiterpenes beta-eudesmol (3) and 8alpha-hydroxy-beta-eudesmol (4), a diterpene carnosic acid 12-methyl ether (12-methoxycarnosic acid) (5), three triterpenes erithrodiol 3-acetate, oleanolic acid, lupeol and beta-sitosterol were obtained as known compounds from this plant extract. The structures of the isolated compounds were elucidated by spectroscopic methods, including one- and two- dimensional 1H- and 13C-NMR and MS spectroscopies. The selected compounds were tested for antimicrobial activity against standard bacterial strains, and only carnosic acid 12-methyl ether showed antimicrobial activity against S. aureus at 78 microg mL(-1).     

Pharmacological activities of the prenylcoumarins, developed from folk usage as a medicine of Peucedanum japonicum THUNB

In connection with the chemical structure of coumarin 1 (a mixture of acetylangeloylkhellactone and acetyltigloylkhellactone), a compound isolated from Peucedanum japonicum THUNB., we synthesized eight coumarin compounds (3-10) and performed pharmacological studies on these nine compounds, as well as on another coumarin, praeruptorin A (= Pd-Ia) (2), a compound isolated from Peucedanum praeruptorum DUNN. We studied the effects of compounds 1-5 on isolated smooth muscle and of compounds 1-10 on the cardiovascular system. These compounds showed dose-related antagonistic effects on histamine- and Ca(2+)-induced contractions in smooth muscle and the potencies were in the order 2 greater than 1 greater than seselin (3) greater than xanthyletin (4) = 2.2.10-trimethyl-2H,8H-benzo[1,2-b: 3,4-b']dipyran-8-one (5). All the compounds except 7-geranyloxy-4-methylcoumarin (10) produced a dose-related increase in vertebral, carotid and femoral blood flow. Compounds 1, 5, and 4-methyl-7-(3-methyl-2-butenyloxy)coumarin (8) caused an increase in blood pressure, but 3 and 4 caused a slight decrease. Compounds 2, 3, 4, 5, and 8 increased heart rate. Jatamansinone (6) and jatamansinol (7) caused only slight changes in blood pressure. All the compounds except 10 increased heart rate. Compound 1 also increased blood flow in the cerebral cortex. Thus, compound 1 was confirmed to have an inhibitory effect on contraction in isolated smooth muscle and an action increasing arterial blood flow. Among the compounds tested in this study, 3, as well as 6 and 7 synthesized on the basis of 3, showed actions similar to those of Ca2+ blockers and some compounds had papaverine-like activities.(ABSTRACT TRUNCATED AT 250 WORDS)     

A new diphenyl ether from Phoma sp. strain, SHZK-2

A new diphenyl ether methyl 2-(2-formyl-3-hydroxy-5-methylphenoxy)-5-hydroxy-3-methoxybenzoate (3), together with four known compounds, asterric acid (1), methyl asterrate (2), 9(Z),12(Z)-nonadecadienoic acid (4) and orsellinic acid (5), were isolated from the Phoma sp. strain SHZK-2, which was isolated from a polluted environment in southern China. The structures of these compounds were determined by spectroscopic methods. Cytotoxicities of compounds against HEPG2 cell and Raji cell lines were preliminarily evaluated by the MTT method.     

New triterpenoids isolated from the root bark of Ulmus pumila L

Three new triterpenoids, 1-3, were isolated from the dried root bark of Ulmus pumila. Along with the three new compounds, six known triterpenoids, epifriedelanol (4), friedelin (5), oleanolic acid (6), maslinic acid (7), camaldulenic acid (8), and arjunolic acid (9) were also isolated. The structures of new compounds were established as ulmudiol (bauer-7-ene-1alpha,3beta-diol, 1), dehydroulmudiol [bauer-7,9(11)-diene-1alpha,3beta-diol, 2], and ulmuestone [3alpha-hydroxy-11alpha-(4'-hydroxy-3'-methoxy)benzoyloxybauer-1-one, 3], on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. In addition, the cytotoxic activities of these compounds are also reported.     

A new labdane diterpene from the flowers of Solidago canadensis

A new labdane diterpene, 9alpha,16xi-dihydroxy-6-oxo-7,13-labdadien-15,16-olide (solicanolide, 1) and six known compounds identified as quercetin (2), 3-O-caffeoylquinic acid (3, neochlorogenic acid), 5-O-caffeoylquinic acid (4, chlorogenic acid), 4,5-di-O-caffeoylquinic acid (5), 3,5-di-O-caffeoylquinic acid (6) and 3,4-di-O-caffeoylquinic acid (7) were isolated from the flowers of Solidago canadensis. To our knowledge, compound 7 was isolated for the first time in S. canadensis. This work describes the isolation of compounds 1-7 and the structure elucidation of a new compound identified as compound 1. Solicanolide (1) showed cytotoxic activity against A549 (IC(50): 13+/-2 microM), DLD-1 (IC(50): 26+/-2 microM) and WS1 (IC(50): 17+/-1 microM) cell lines.     

A new labdanic norditerpene from Pinus sylvestris

A new labdanic norditerpene and six known labdanic diterpenes were isolated from the petroleum ether extract of the needles of Pinus sylvestris. By spectroscopic methods, the isolated compounds were determined as 15-norpinifolic acid (1), pinifolic acid (2), 4-eplimbricataloic acid (3), monomethyl pinifolate (4), 18α-acetoxylabd-8(17)-en-15-oic acid (5), 2-pentenoic acid (6) and 3β-hydroxy-8(17),E-13-labdadien-15-oic acid (7), respectively. Compound 1 showed significant anti-tumour activity.     

New glycosides from the Japanese fern Hymenophyllum barbatum

Thirteen glycosides and methyl (3R,5R)-5-hydroxy-(beta-D-glucopyranosyloxy)-hexanoate were newly isolated from the Japanese fern Hymenophyllum barbatum, although our previous work revealed the isolation of hemiterpene glycosides, hymenosides A-J, from the same species. The structures of the newly isolated glycosides were elucidated by extensive two-dimensional (2D) NMR and/or chemical evidence. The structures of those aglycones were divided into four types, 2-methyl-but-2-ene-1,4-diol, 2-hydroxymethyl-but-2-ene-1,4-diol, 2-methylene-butane-1,3,4-triol, and 3-hydroxy-5-hexanolide. The sugar moieties, which were acylated by phenylacetic acid derivatives, were also established by chemical and spectroscopic methods. Eight glucosides of the isolated compounds in the present investigation had a bitter or weakly pungent taste. It is clear that a phenylacetyl group attached to glucose or allose as an ester is necessary for the bitter taste.     

A new antibacterial diterpene from the roots of Salvia caespitosa

From the roots of Saliva caespitosa Montbret and Aucher ex. Bentham a new diterpene 6beta-hydroxyisopimaric acid (1) has been isolated together with four known diterpenes, one new triterpenoid, 3-acetylvergatic acid (2), as well as five known triterpenoids, two steroids and a flavone. The structures of the compounds were established by spectroscopic analyses. The isolated compounds were tested against standard bacterial strains. Only the new diterpene, 6beta-hydroxyisopimaric acid has strong activity (MIC 9 microg/ml) against S. aureus and (MIC 18 microg/ml) against S. epidermidis as well as against B. subtilis (MIC 9 microg/ml).     

Chemical Constituents from Strychnos Cathayensis

Secostrychnosin ( 1 ), a new secoiridoid, as well as seven compounds never before isolated from nature: 4‐tert‐butyl‐2‐oxazolidinone ( 2 ), 3‐acetoxyindole ( 3 ), indole‐2‐carboxylic acid ( 4 ), benzocaine ( 5 ), 3‐acetylindole ( 6 ), butylparaben ( 7 ) and 2‐hydroxy‐3‐methoxybenzaldehyde ( 8 ), together with fifty other known compounds, have been isolated from the stem of Strychnos cathayensis. These compounds include twenty‐three alkaloids, twelve benzenoids, four steroids, three flavonoids, three iridoids, two triterpenoids, two secoiridoids, two fatty acids, one lignan, one acetophenone, one coumarin, one chromane, one tetraterpenoid, one tannin, and one organic acid. The structures of these compounds were determined by means of spectralanalyses.     

Pentacyclic triterpenoids from the aerial parts of Lantana camara

Three new pentacyclic triterpenoids, camaryolic acid (1), methylcamaralate (2) and camangeloyl acid (3) and six known compounds beta-sitosterol 3-O-beta-D-glucopyranoside (4), octadecanoic acid (5), docosanoic acid (6), palmitic acid (7), camaric acid (8) and lantanolic acid (9) were isolated from the aerial parts of Lantana camara. Structures of the new compounds were elucidated by spectroscopic and chemical methods.     

Antioxidant secondary metabolites from Geranium lasiopus Boiss. & Heldr

Chromatographic studies on the EtOAc soluble portion of the MeOH extract of Geranium lasiopus led to the isolation of eight flavonoids (kaempferol (1), quercetin (2), quercetin 3-O-β-glucopyranoside (3), quercetin 3-O-β-galactopyranoside (4), kaempferol 3-O-α-rhamnopyranosyl-(1?→?6)-β-glucopyranoside (5), quercetin 3-O-α-rhamnopyranosyl-(1?→?6)-β-glucopyranoside (6), kaempferol 3-O-α-rhamnopyranosyl-(1?→?2)-β-glucopyranoside (7) and quercetin 3-O-α-rhamnopyranosyl-(1?→?2)-β-glucopyranoside (8)), two simple phenolic compounds (gallic acid (9) and its methyl ester (10)) and a hydrolysable tannin (pusilagin (11)). The structures of the compounds were elucidated by 1- and 2-dimensional NMR techniques ((1)H, (13)C, COSY, HMBC, HMQC) and ESI-TOF-MS spectrometry. Inhibitory effects on H(2)O(2)-induced lipid peroxidation in human red blood cells of the different extracts of G. lasiopus, as well as isolated compounds, were investigated. All tested compounds showed comparable or higher activity than that of ascorbic acid and trolox.     

Phytochemical and biological studies on Saudi Commiphora opobalsamum L

The aerial part of Commiphora opobalsamum L. (Burseraceae) growing in Saudi Arabia was subjected to a phytopharmacological investigation in order to identify its major chemical constituents and to evaluate its extracts and isolated compounds in preliminary in vitro assays for antimicrobial, antimalarial, antitumor, anti-inflammatory (COX-2 inhibition), antioxidant and estrogenic activity. Six compounds were isolated and identified as the triterpenes friedelin, canophyllal, and oleanonic acid; the flavonols mearnsetin and quercetin; and syringic acid. The ethyl acetate extract was moderately active against Staphylococcus aureus, Pseudomonas aeruginosa, and Plasmodium falciparum; while the petroleum ether and chloroform extracts inhibited COX-2 at 5 and 10 microg mL(-1), respectively. Of the isolated compounds, syringic acid showed moderate antimalarial, anticandidal, and antimycobacterial activity; while mearnsetin and quercetin exhibited antioxidant activity comparable to ascorbic acid and trolox. This is the first detailed phytochemical investigation of C. opobalsamum L. growing in Saudi Arabia and elsewhere. The isolated compounds are reported from this plant for the first time and their full (1)H and (13)C NMR assignments are included.     

Endodesmiadiol, a friedelane triterpenoid, and other antiplasmodial compounds from Endodesmia calophylloides

From the ethyl acetate extract of the stem bark of Endodesmia calophylloides (Guttiferae), a novel friedelane triterpenoid named endodesmiadiol (1), as well as the known compounds friedelin (2), canophyllol (3), canophyllal (4), cerin (5), morelloflavone (6), volkensiflavone (7), 8-deoxygartanin (8), 3 beta-acetoxyoleanolic acid (9) and 1,8-dihydroxy-3-isoprenyloxy-6-methylxanthone (10) have been isolated. The structures of these compounds were established by spectroscopic analysis, and the relative configuration of endodesmiadiol (1) was confirmed by X-ray diffraction. The antiplasmodial activity of the isolated compounds was evaluated against the W2 strain of Plasmodium falciparum which is resistant to chloroquine and other antimalarial drugs. All the compounds were found to be active with IC50 values ranging from 7.2 to 23.6 microM. The IC50 of endodesmiadiol was found to be 11.8 microM.     

Seimatoric acid and colletonoic acid:Two new compounds from the endophytic fungi,Seimatosporium sp.and Colletotrichum sp.

A new metabolite,named seimatoric acid(1),representing a new oxobutanoic acid derivative has been isolated from Seimatosporium sp., in addition to four known compounds viz.,2-hydroxymethyl-4β,5α,6β-trihydroxycyclohex-2-enone(2),(-)-phyllostine(3),(+)-epiepoxydon(4) and(+)-epoxydon monoacetate(5).Similarly one new benzoic acid derivative,named colletonoic acid(6) was isolated from the ethyl acetate fraction of Colletotrichum sp.The structures of the new compounds were elucidated by detailed ~1 H NMR,~(13)C NMR,COSY,HMQC.HMBC spectroscopic analysis,and HR-E1-MS.Seimatoric acid(1)was also isolated from another taxonomical unidentified fungal strain 4295 in ourgroup.The structures of the known compounds were elucidated by their spectral data comparison to literature data.Preliminary studies showed that colletonoic acid(6) showed good antibacterial,antifungal,and antialgal activities.     

Triterpenoids from Eugenia grandis: structure elucidation by NMR spectroscopy

A new pentacyclic triterpenoid, 2alpha,3beta-dihydroxylup-12-en-28-oic acid (1) and a rarely encountered pentacyclic triterpenoid, 3beta-hydroxylup-12-en-28-oic acid (2), together with five known compounds, friedelin (3), 3beta-friedelinol (4), betulinic acid (5), oleanolic acid (6) and beta-sitosterol (7) were isolated from the chloroform extract of stem bark of Eugenia grandis (Syn: Syzygium grande). The structure and stereochemistry of the new compound (1) and the rarely encountered compound (2) were established by 1D and 2D NMR spectroscopic techniques. All the above isolated compounds from this plant are reported for the first time.     

Caffeic acid oligomers with hyaluronidase inhibitory activity from Clinopodium gracile

Eight new caffeic acid oligomers, clinopodic acids J-Q (1-8), were isolated from whole plants of Clinopodium gracile, together with nine known caffeic acid oligomers. The caffeic acid oligomers with two to four dihydrobenzofuran rings were isolated as natural products for the first time. Clinopodic acid M (4) showed the strongest hyaluronidase inhibitory activity, IC(50) (19 μM) among the 22 compounds isolated from this plant.     

New galloyl derivative from winged sumac (Rhus copallinum) fruit

Twelve compounds were isolated from Winged Sumac (Rhus copallinum) fruit and their structures were elucidated on the basis of NMR and mass spectral data. The isolates included a new galloyl derivative, (R)-galloyl malic acid dimethyl ester (1), and eleven known compounds, gallic acid (2), methyl gallate (3), glucogallin (4), methyl m-digallate (5), methyl p-digallate (6), quercetin (7), myricetin (8), rhamnazin (9), kaempferol (10), betulinic acid (11), and oleanolic acid (12). All of the compounds were evaluated for antiproliferative effects against human colon tumorigenic (HCT-116, Caco-2) and nontumorigenic (CCD18-Co) cell lines.