Cytotoxic Sesterterpenes from Thai Marine Sponge Hyrtios erectus.

Four sesterterpenes, erectusolides B, C, D, and seco-manoalide-25-methyl ether, two 2-furanone derivatives, erectusfuranones A and B, together with thirteen known sesterterpenes, (6)-neomanoalide-24-acetate, two diastereomers of 24--methylmanoalide, luffariolide B, manoalide, (6)- and (6)-neomanoalide, seco-manoalide, scalarafuran, 12-acetylscalarolide, 12-epi--deacetyl-19-deoxyscalarin, 12-epi-scalarin, and 12--deacetyl-12-epi-scalarin, three indole alkaloids, 5-hydroxy-1-indole-3-carbaldehyde, hyrtiosine A, and variabine B, and one norterpene, cavernosine were isolated from the marine sponge . Their structures were determined by means of spectroscopic methods and the absolute configurations of the asymmetric centers were determined using the modified Mosher's method. The cytotoxic activities for the isolated compounds have been reported.

Antiplasmodial dimeric chalcone derivatives from the roots of Uvaria siamensis.

Four dimeric chalcone derivatives, 8″,9″-dihydrowelwitschin H, uvarins A-C, a naphthalene derivative, 2-hydroxy-3-methoxy-6-(4'- hydroxyphenyl)naphthalene, and the known dimeric chalcones, dependensin and welwitschin E, flavonoids, a cyclohexane oxide derivative, an aromatic aldehyde were isolated from the roots of Uvaria siamensis (Annonaceae). The structures of the compounds were elucidated by spectroscopic analysis, as well as by comparison with literature data. The isolated compounds with a sufficient amount for biological assays were evaluated for their antimalarial, antimycobacterial, and cytotoxic activities.

A new dihydrobenzofuran lignan and potential α-glucosidase inhibitory activity of isolated compounds from Mitrephora teysmannii.

A new dihydrobenzofuran lignan, (2R,3S)-2-(3',4'-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydrobenzofuran-3-methyl acetate, named as mitredrusin (1), was isolated from the leaves of Mitrephora teysmannii (Annonaceae) together with 12 known compounds including a related dihydrobenzofuran lignan: (-)-3',4-di-O-methylcedrusin (2), four polyacetylenic acids: 13(E)-octadecene-9,11-diynoic acid (3), 13(E),17-octadecadiene-9,11-diynoic acid (4), octadeca-9,11,13-triynoic acid (5) and octadeca-17-en-9,11,13-triynoic acid (6), five lignans: (-)-eudesmin (7), (-)-epieudesmin (8), (-)-phillygenin (9), magnone A (10) and forsythialan B (11) and two megastigmans: (3S,5R,6S,7E,9R)-7-megastigmene-3,6,9-triol (12) and annoionol A (13). The chemical structures of these compounds were established on the basis of their 1-D and 2-D NMR spectroscopic data. All compounds were evaluated for their α-glucosidase inhibitory activity.

Ent-pimarane and ent-trachylobane diterpenoids from Mitrephora alba and their cytotoxicity against three human cancer cell lines.

Bioassay-guided fractionation of the hexane extract of the branches of Mitrephora alba led to the isolation of five diterpenoids: ent-8β-hydroxypimar-15-en-18-oic acid, ent-15,16-dihydroxypimar-8(14)-en-18-oic acid, ent-3β-hydroxytrachyloban-18-oic acid, ent-3β-hydroxytrachyloban-18-al and methyl ent-3β-hydroxytrachyloban-18-oate, together with five related known diterpenoids. The structures were elucidated by spectroscopic analysis and comparison with literature data. All isolated compounds were evaluated for their cytotoxic activities against three human cancer cell lines.

Two new C-benzylated dihydrochalcone derivatives from the leaves of Melodorum siamensis.

Two new C-benzylated dihydrochalcone derivatives, 4,2',4'-trihydroxy-6'-methoxy-3'(2''-hydroxybenzyl)dihydrochalcone (1) and 2',4'-dihydroxy-4,6'-dimethoxy-3'(2''-hydroxybenzyl)dihydrochalcone (2), along with six known flavonoid derivatives (3-8), a known dihydrochalcone dimer (9), three known aromatic esters (10-12), and one known aromatic amide (13), were isolated from the leaves of Melodorum siamensis. The structures of the compounds were elucidated by spectroscopic analysis, mainly 1D and 2D NMR techniques (1H, 13C, COSY, HMQC, and HMBC), as well as by comparison with literature data. The isolated compounds with a sufficient amount for biological assays were evaluated for their antimalarial, antimycobactirial, and cytotoxic activities.

A new phenolic compound with anticancer activity from the wood of Millettia leucantha.

A new phenolic compound, 1-(3-hydroxy-4-methoxyphenyl)-3-(2,4-dihydroxy-5-methoxyphenyl) propan-1-ol, named as millettinol (1), along with six known compounds, medicarpin (2), 4-hydroxy-3-methoxy-8,9-methylenedioxypterocarpan (3), 5,4'-dihydroxy-7,8-dimethoxyisoflavone (4), physcion (5), (R)-(-)-mellein (6) and isoliquiritigenin (7), were isolated from the wood of Millettia leucantha. The structures of the compounds were determined by an analysis of their spectroscopic data. Some of the isolates were tested for anticancer activity.

N-(9,11-Dimeth-oxy-4-oxo-2,3,4,6,7,11b-hexa-hydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide.

The title schulzeine derivative, C(22)H(24)N(2)O(4), crystallizes with two crystallographically independent mol-ecules of almost identical conformation in the asymmetric unit. The tricyclic core of schulzeine has a fused-three-ring system comprising the tetra-hydro-isoquinoline and δ-lactam moieties. In both mol-ecules, the pyridine ring adopts a twisted-boat conformation, whereas the lactam ring is in a boat conformation.

Anthraquinones from the roots of Prismatomeris malayana.

A novel anthraquinone, 1,3-dihydroxy-5,6-dimethoxy-2-methoxymethyl-9,10-anthraquinone (9) and a new natural product, 2-hydroxymethyl-1-methoxy-9,10-anthraquinone (8) were isolated from the roots of Prismatomeris malayana together with seven known anthraquinones, tectoquinone (1), 1-hydroxy-2-methyl-9,10-anthraquinone (2), rubiadin (3), rubiadin-1-methyl ether (4), 1,3-dihydroxy-5,6-dimethoxy-2-methyl-9,10-anthraquinone (5), nordamnacanthal (6), and damnacanthal (7). Their structures were determined on the basis of spectroscopic data. Some of the anthraquinones were tested for anticancer, antifungal, and antimalarial activities.

Anti-inflammatory activity of 4-arylcoumarins from endophytic Streptomyces aureofaciens CMUAc130 in murine macrophage RAW 264.7 cells.

This research was undertaken to test the in vitro anti-inflammatory action of 5,7,4'-trimethoxy-4-phenylcoumarin and 5,7-dimethoxy-4-phenylcoumarin produced by Streptomyces aureofaciens CMUAc130. The effects of the two coumarins were investigated on the formation of NO, PGE2, and TNF-alpha and also on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in lipopolysaccharide (LPS)-induced murine macrophage RAW 264.7 cells.

Constituents of the leaves of Holarrhena pubescens.

The leaves of Holarrhena pubescens yielded a new naringenin glycoside (1), together with naringin, naringenin 7-O-beta-D-glucoside, lupeol, lupeol beta-hydroxyhexadecanoate and ursolic acid. The structure of 1 was determined by spectral analysis.

Chemical constituents of the roots of Piper sarmentosum.

Sixteen compounds were isolated from the fresh roots of Piper sarmentosum. Seven of these have been previously isolated from the fruits and leaves of this plant: the aromatic alkene (1), 1-allyl-2-methoxy-4,5-methylenedioxybenzene (4), beta-sitosterol, pyrrole amide (6), sarmentine (10), sarmentosine (13) and pellitorine (14). (+)-Sesamin (2), horsfieldin (3), two pyrrolidine amides 11 and 12, guineensine (15) and brachystamide B (16) are new for P.

Chromones from the branches of Harrisonia perforata.

Four new chromones, perforamone A, B, C, and D have been isolated together with six known compounds, peucenin-7-methyl ether, O-methylalloptaeroxylin, perforatic acid, eugenin, saikochromone A and greveichromenol, from the branches of Harrisonia perforata (Simaroubaceae). The structures were identified by spectroscopic data. The compounds were tested for antimycobacterial and antiplasmodial activities.

Cerebrosides and a monoacylmonogalactosylglycerol from Clinacanthus nutans.

A mixture of nine cerebrosides and a monoacylmonogalactosylglycerol were separated from the leaves of Clinacanthus nutans. The structures of the cerebrosides were characterized as 1-O-beta-D-glucosides of phytosphingosines, which comprised a common long-chain base, (2S,3S,4R,8Z)-2-amino-8(Z)-octadecene-1,3,4-triol with nine 2-hydroxy fatty acids of varying chain lengths (C(16), C(18), C(20-26)) linked to the amino group. The glycosylglyceride was characterized as (2S)-1-O-linolenoyl-3-O-beta-D-galactopyranosylglycerol.

Sulfur-containing compounds from Clinacanthus siamensis.

Two new sulfur-containing compounds, trans-3-methylsulfonyl-2-propenol (1) and trans-3-methylsulfinyl-2-propenol (2) were isolated together with trans-3-methylthioacrylamide (3), entadamide A (4) and entadamide C (5) from the leaves of Clinacanthus siamensis. The structures were established on the basis of the spectroscopic data. The compounds were tested for antimalarial and antimycobacterial activity.

New rearranged clerodane diterpenes from Tinospora baenzigeri.

Baenzigeroside B, a new rearranged clerodane diterpene glucoside, was isolated from the stems of Tinospora baenzigeri. The aglycone of baenzigeroside B, baenzigeride B (isolated as its acetate), was found together with baenzigeride A, baenzigerosides A and B in the leaves of the same plant. Baenzigeride B and baenzigeroside B are the first examples of a new class of rearranged clerodane diterpenes.

Anti-inflammatory activity of compound D {(E)-4-(3',4'-dimethoxyphenyl)but-3-en-2-ol} isolated from Zingiber cassumunar Roxb.

Compound D, (E)-4-(3',4'-dimethoxyphenyl)but-3-en-2-ol, is one of many compounds found in the hexane extract of Zingiber cassumunar Roxb. The anti-inflammatory activity of compound D was assessed using various inflammatory models in comparison with aspirin, indomethacin and prednisolone. The results obtained showed that the anti-inflammatory effect of compound D mediated prominently on the acute phase of inflammation.

A triterpenoid saponin from Maesa ramentacea.

The structure of a piscicidal triterpenoid saponin (saponin A) isolated from the leaves of Maesa ramentacea has been shown to be 3-O-[[(alpha-rhamnopyranosyl (1-->2)-alpha-L-rhamnopyranosyl(1-->2)-beta-D-galactopyranosyl (1-->3)]-[beta-D-glucopyranosyl(1-->2)]-beta-D-glucuronopyranosyl] barringtogenol C21, 22-O-diangeloate. Extensive use was made of homo- and heteronuclear 2D NMR techniques.

Cyanogenic and non-cyanogenic glycosides from Manihot esculenta.

In addition to lotaustralin and linamarin, a novel cyanogenic glycoside, 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)-2-met hylbutanenitrile , two novel non-cyanogenic glycosides, (2S)-((6-O-(beta-D-apiofuranosyl)-beta-D- glucopyranosyl)oxy)butane and 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)propane, and a simple non-cyanogenic glycoside, ethyl beta-D-glucopyranoside, were isolated from an ethanolic extract of the fresh root cortex of Manihot esculenta. From a methanolic extract of the fresh leaves of this species lotaustralin and linamarin, and two flavonoid glycosides, kaempferol-3-O-rutinoside and quercetin-3-O-rutinoside were isolated.

Antiinflammatory activity of flavonoids.

Fourteen flavonoids (flavones,- flavanones and chalcones) were assayed for oral antiinflammatory activity using carrageenan-induced hind paw edema in rats. The structural features necessary for antiinflammatory activity appear to be the presence of methoxyl groups at C5 and C7 of ring A and the pyrano ring B of the flavonoid molecule. Negligible or low antiinflammatory activities were found in the chalcone derivatives.

Triterpenoid glycosides from Schefflera lucantha.

Three new triterpenoid glycosides were isolated from the leaves of Schefflera lucantha Viguier. Based on the spectroscopic data, especially 2D NMR, the structures of glycosides have been established as 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucuronopyranosyl] betulinic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl (1-->2)-beta-D-glucuronopyranosyl]betulinic acid and 3-O-[alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucuronopyranosyl]oleanolic acid.