New pterosin sesquiterpenes and antitubercular constituents from Pteris ensiformis.

Two new pterosin sesquiterpenes, (2S)-13-hydroxypterosin A (1) and (2S,3S)-12-hydroxypterosin Q (2), were isolated from the whole plants of Pteris ensiformis, together with six known compounds. The structures of 1 and 2 were determined through extensive 1D/2D-NMR and MS analyses. Compound 2 exhibited antitubercular activity (MIC 6.25 µg/ml) against Mycobacterium tuberculosis H37 Rv in vitro.

Secondary metabolites from the unripe pulp of Persea americana and their antimycobacterial activities.

The fruits of Persea americana (Avocado) are nowadays used as healthy fruits in the world. Bioassay-guided fractionation of the active ethyl acetate soluble fraction has led to the isolation of five new fatty alcohol derivatives, avocadenols A-D (1-4) and avocadoin (5) from the unripe pulp of P. americana, along with 12 known compounds (6-17). These structures were elucidated by spectroscopic analysis. Among the isolates, avocadenol A (1), avocadenol B (2), (2R,4R)-1,2,4-trihydroxynonadecane (6), and (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (7) showed antimycobacterial activity against Mycobacterium tuberculosis H(37)R(V)in vitro, with MIC values of 24.0, 33.8, 24.9, and 35.7 µg/ml, respectively.

Secondary metabolites from the stems of Engelhardia roxburghiana and their antitubercular activities.

Bioassay-guided fractionation of stems of Engelhardia roxburghiana led to isolation of: four diarylheptanoids, engelheptanoxides A-D (1-4); two cyclic diarylheptanoids, engelhardiols A (5) and B (6); one naphthoquinone dimer, engelharquinonol (7); and one 1-tetralone, (4S)-4,6-dihydroxy-1-tetralone (8), along with 24 known compounds (9-32). The structures of 1-8 were by spectroscopic analysis. Compounds 5, 6, 13, 22, and 23 showed antitubercular activity against Mycobacterium tuberculosis H(37)Rv with MIC values of 72.7, 62.1, 9.1, 15.3, and 70.1µM, respectively.

Secondary metabolites from the root of Ehretia longiflora and their biological activities.

Bioassay-guided fractionation of the methanolic extract of the root of Ehretia longiflora (Boraginaceae) afforded eight compounds, ehretiquinone (1), ehretiolide (2), ehreticoumarin (3), ehretilactone A (4), ehretilactone B (5), ehretiamide (6), ehretine (7), and ehretiate (8), together with 12 known compounds (9-20). The relative configuration of 1 was determined by single crystal X-ray diffraction. Among the isolates, 1 and prenylhydroquinone (14) showed antitubercular activity against Mycobacterium tuberculosis strain H37Rv with MIC values of 25.0 and 26.2 µg/mL, respectively. Moreover, 1 exhibited inhibitory effects on N-formylmethionylleucylphenylalanine (fMLP)-induced superoxide production, with IC50 value of 0.36±0.03µM.

Secondary metabolites from the root wood of Zanthoxylum wutaiense and their antitubercular activity.

Bioassay-guided fractionation of the root wood of Zanthoxylum wutaiense led to the isolation of five new compounds, wutaipyranol A (1), 8-methoxywutaipyranol A (2), demethoxywutaiensal (3), demethoxywutaiensol (4), and dihydrodemethoxywutaiensol (5), together with six known compounds. Their structures were elucidated by 1D- and 2D-NMR, as well as MS analyses. Among the isolates, wutaipyranol A (1), 8-methoxywutaipyranol A (2), and demethoxywutaiensal (3) exhibited antitubercular activities against Mycobacterium tuberculosis H(37) Rv in vitro, with MIC values of 52.4, 55.6, and 45.8 µg/ml, respectively.

Chemical constituents and antitubercular activity of Formosan Pisonia umbellifera.

Bioassay-guided fractionation of the methanolic extract of the stem of Pisonia umbellifera (Nyctaginaceae) afforded the three new compounds, secopisonic acid (1), 6,8-dimethylisogenistein (2), and (+)- ENT-ficusol (3), and four first isolates from nature, pisoninol I (4), pisoninol II (5), pisoquinoline (6), and pisodienone (7), together with fifteen known compounds. Their structures were elucidated by analysis of spectroscopic data. Seven of these isolates, 3, 7, 12, 16, 18, 20, and 21 showed antitubercular activities against Mycobacterium tuberculosis H37R (V) in vitro, with MIC values ≤ 50 µg/mL.

Antitubercular resorcinol analogs and benzenoid C-glucoside from the roots of Ardisia cornudentata.

Bioassay-guided fractionation of the roots of Ardisia cornudentata Mez (Myrsinaceae) led to the isolation of three new compounds, 3-methoxy-2-methyl-5-pentylphenol (1), 3-methoxy-2-methyl-5-(1'-ketopentyl)phenol (2), and cornudoside (3), together with twenty-six known compounds. Their structures were elucidated by analysis of spectroscopic data. Thirteen of these isolates, 1, 2, 4- 6, 9- 15, and 21 showed antitubercular activities against Mycobacterium tuberculosis H37R (V) IN VITRO, with MIC values of 2.5-60 µg/mL. Two alkyl benzoquinones, ardisianone (7) and cornudentanone ( 8), were reported for their selective cytotoxic activity against the NCI-H460 cancer cell line (IC (50) values of 2.3, 2.5 µg/mL).

Secondary metabolites and antimycobacterial activities from the roots of Ficus nervosa.

Bioassay-guided fractionation of the active AcOEt-soluble layer led to the isolation of two new pyranocoumarins, 3-hydroxyxanthyletin (1) and 3-methoxyxanthyletin (2), along with 22 known compounds including four simple coumarins, i.e., xanthyletin (3), umbelliferone (4), scopoletin (5), and (+)-(S)-marmesin (6); nine flavonoids, i.e., carpachromene (7), parvisoflavone B (8), alpinumisoflavone (9) genistein (10), 2'-hydroxygenistein (11), prunetin (12), cajanin (13), apigenin (14), and (2S)-naringenin (15); three benzenoids, i.e., 4-hydroxybenzaldehyde (16), vanillin (17), and (S)-lasiodiplodin (18); five steroids, i.e., ergosterol peroxide (19), a mixture of 6beta-hydroxystigmast-4-en-3-one (20) and 6beta-hydroxystigmasta-4,22-dien-3-one (21), and a mixture of beta-sitosterol (22) and stigmasterol (23); and one triterpenoid, i.e., oleanolic acid (24) from the roots of Ficus nervosa. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR as well as MS analyses. Among these isolates, 3-hydroxyxanthyletin (1), genistein (10), prunetin (12), and (2S)-naringenin (15) showed antimycobacterial activities against Mycobacterium tuberculosis H(37)R(V) in vitro with MIC values of 16, 35, 30, and < or =2.8 microg/ml, respectively.

seco-Abietane diterpenoids, a phenylethanoid derivative, and antitubercular constituents from Callicarpa pilosissima.

Six new compounds, including five new seco-abietane diterpenoids, 12-deoxy-seco-hinokiol methyl ester (1), 12-deoxy-11,12-dihydro-seco-hinokiol methyl ester (2), callicarpic acid A (3), 9alpha-hydroxycallicarpic acid A (4), and callicarpic acid B (5), and a new phenylethanoid derivative, 4-hydroxyphenethyl tetradecanoate (6), have been isolated from the leaves and twigs of Callicarpa pilosissima, together with 14 known compounds (7-20). The structures of these new compounds were determined through analyses of physical data. 12-Deoxy-11,12-dihydro-seco-hinokiol methyl ester (2), callicarpic acid B (5), and alpha-tocopherol trimer B (15) exhibit antitubercular activities (MICs

Endiandric Acid Analogues from the Roots of Beilschmiedia erythrophloia.

Investigation of the roots of Beilschmiedia erythrophloia has led to the isolation of seven new endiandric acid analogues, erythrophloins A-F (1-6) and beilcyclone A (7), together with 11 known compounds. The structures of 1-7 were determined using spectroscopic techniques. Two constituents, erythrophloin C (3) and suberosol B (8), exhibited antitubercular activity against Mycobacterium tuberculosis H37Rv, showing MIC values of 50 and 28.9 microg/mL, respectively.

Dihydroagarofuranoid sesquiterpenes, a lignan derivative, a benzenoid, and antitubercular constituents from the stem of Microtropis japonica.

Four new compounds, including two new dihydroagarofuranoid sesquiterpenes, 8-benzoyloxymutangin (1) and 15-acetoxyorbiculin G (2), a new lignan derivative, 9,9'- O-di-(Z)-feruloyl-(-)-secoisolariciresinol (3), and a new benzenoid, 5'-methoxyevofolin B (4), have been isolated from the stem of Microtropis japonica, together with 20 known compounds (5- 24). 3-Ethoxy-4-hydroxybenzaldehyde (5) was identified from a natural source for the first time. The structures of these new compounds were determined through analyses of physical data. 15-Acetoxyorbiculin G (2), celahin C (6), and salasol A (7) exhibit antituberculosis activities (MICs < or = 39.6 microM) against Mycobacterium tuberculosis H 37Rv in vitro.

A new dihydroagarofuranoid sesquiterpene from Microtropis fokienensis with antituberculosis activity.

A new dihydroagarofuran-based sesquiterpene, 8-acetoxymutangin (1), was isolated from the stems of Microtropis fokienensis, together with eight known compounds, including mutangin (2). Their structures were determined through in-depth spectroscopic and mass-spectrometric analyses. Among the isolated compounds, 1 exhibited potent in vitro antituberculosis activity, with an MIC value of 10.0 microg/ml against Mycobacterium tuberculosis 90-221387, which is considerably better than that of mutangin (2). The activity of 1 lies in the same range as that of the clinic drug ethambutol (MIC 6.25 microg/ml), despite completely different chemical structures, which indicates different modes of action.

Novel epoxyfuranoid lignans and antitubercular constituents from the leaves of Beilschmiedia tsangii.

Three new epoxyfuranoid lignans, 4alpha,5alpha-epoxybeilschmin A (1), 4alpha,5alpha-epoxybeilschmin B (2), and beilschmin D (3), together with nine known compounds have been isolated from the leaves of Beilschmiedia tsangii. The structures of these new compounds were determined through spectral analyses. Among the isolates, beilschmin A (4) and beilschmin B (5) exhibited potent antitubercular activities (MICs = 2.5 and 7.5 microg/mL, respectively) against Mycobacterium tuberculosis 90 - 221387 in vitro.

Antitubercular dihydroagarofuranoid sesquiterpenes from the roots of Microtropis fokienensis.

Four new dihydroagarofuranoid sesquiterpenes (1-4) and a new hydroxybenzylsalicylaldehyde, forkienin (5), together with nine known compounds have been isolated from the roots of Microtropis fokienensis. The structures of the new compounds were determined through analyses of physical data. Compounds 3, 4, 7, and 8 exhibited potent antitubercular activities (MICs < or = 26.0 microM) against Mycobacterium tuberculosis 90-221387 in vitro.

Benzopyrans, biphenyls and xanthones from the root of Garcinia linii and their activity against Mycobacterium tuberculosis.

A new benzopyran, (S)-3-hydroxygarcibenzopyran, and three new biphenyls, garcibiphenyl C, garcibiphenyl D, garcibiphenyl E, together with thirteen known compounds have been additionally isolated from the root of Garcinia linii. The structures of these new compounds were determined through spectral analyses. Among the isolates, 1,7-dihydroxy-3-methoxyxanthone and 1,5-dihydroxy-3-methoxyxanthone showed antitubercular activities with MICs of 3.1 +/- 0.5 and 6.3 +/- 1.0 microg/mL against Mycobacterium tuberculosis 90-221,387 in vitro, respectively.

Antitubercular constituents from the stem wood of Cinnamomum kotoense.

Five new compounds, kotolactone A (1), kotolactone B (2), secokotomolide (3), kotodiol (4), and 2-acetyl-5-dodecylfuran (5), and 36 known compounds have been isolated from the stem wood of Cinnamomum kotoense. The structures of these new compounds were determined by means of spectroscopic analysis. The known butanolides, isoobtusilactone A (6) and lincomolide B (7), showed in vitro antitubercular activities with MIC values of 22.48 and 10.16 microM, respectively, against Mycobacterium tuberculosis 90-221387.

Antitubercular constituents from the roots of Engelhardia roxburghiana.

Three new compounds, engelhardione, (-)-5-hydroxy-4-methoxy-1-tetralone, and 3-methoxycarbonyl-1,5-dihydroxyanthraquinone, together with twelve known compounds have been isolated from the roots of Engelhardia roxburghiana. The structures of these new compounds were determined through spectral analyses. Engelhardione, 3-methoxyjuglone, and (-)-4-hydroxy-1-tetralone showed antitubercular activities with MIC values=3.125, 3.125, and 6.25 microg/mL against Mycobacterium tuberculosis 90-221,387, respectively, and with MIC values=0.2, 0.2, and 4.0 microg/mL against M. tuberculosis H37Rv, individually.