Limonoids from the Seeds of Swietenia macrophylla and Their Anti-Inflammatory Activities.

A new limonoid, swietemacrophin (1), was isolated from the seeds of Swietenia macrophylla, together with five known compounds 2-6. The structure of 1 was determined through extensive 1D/2D-NMR and mass-spectrometric analyses. Swietemacrophin (1), humilinolide F (2), 3,6-O,O-diacetylswietenolide (3), 3-O-tigloylswietenolide (4), and swietemahonin E (5) exhibited inhibition (IC50 values≤45.

Biphenyl-Type Neolignan Derivatives from the Twigs of Magnolia denudata and Their Anti-Inflammatory Activity.

Two new biphenyl-type neolignan derivatives, 2-[2-(hydroxymethyl)-1-benzofuran-5-yl]-4-(prop-2-en-1-yl)phenol (1) and 2'-ethoxy-5,5'-di(prop-2-en-1-yl)biphenyl-2-ol (2), were isolated from the twigs of Magnolia denudata, together with six known compounds (3-8). The structures of 1 and 2 were determined through extensive 1D- and 2D-NMR and mass-spectrometric analyses. Magnolol (6) and honokiol (7) exhibited potent inhibition (IC50 values=4.

New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses.

Three new coumarin derivatives, 8-formylalloxanthoxyletin (1), avicennone (2), and (Z)-avicennone (3), have been isolated from the stem bark of Zanthoxylum avicennae (Z. avicennae), together with 15 known compounds (4-18). The structures of these new compounds were determined through spectroscopic and MS analyses.

Biflavans, Flavonoids, and a Dihydrochalcone from the Stem Wood of Muntingia calabura and Their Inhibitory Activities on Neutrophil Pro-Inflammatory Responses.

Muntingia calabura (Tiliaceae) is commercially used in healthcare for the improvement of hypertension, myocardial infarction, spasm, and inflammatory conditions. Its fruits can be processed into jam and the leaves can be used for making tea. In the work reported herein a new biflavan, (M),(2S),(2''S)-,(P),(2S),(2''S)-7,8,3',4',5',7'',8'',3''',4''',5'''-decamethoxy-5,5'' biflavan (1), a new flavone, 4'-hydroxy-7,8,3',5'-tetramethoxyflavone (2), and a new dihydrochalcone, (R)-2',β-dihydroxy-3',4'-dimethoxydihydrochalcone (3), have been isolated from the stem wood of M.

New thymol derivatives and cytotoxic constituents from the root of Eupatorium cannabinum ssp. asiaticum.

Two new thymol (=5-methyl-2-(1-methylethyl)phenol) derivatives, 8,10-didehydro-9-(3-methylbutanoyl)thymol 3-O-tiglate (1) and 9-O-angeloyl-8-methoxythymol 3-O-isobutyrate (2), were isolated from the root of Eupatorium cannabinum ssp. asiaticum, together with six known compounds, 3-8. The structures of 1 and 2 were determined through extensive 1D/2D-NMR and MS analyses.

Microjaponin, a new dihydroagarofuranoid sesquiterpene from the stem of Microtropis japonica with antituberculosis activity.

A new dihydroagarofuran-based sesquiterpene, microjaponin (1), was isolated from the stem of Microtropis japonica. Its structure was determined by in-depth spectroscopic and mass-spectrometric analyses. Microjaponin (1) exhibited potent in vitro antituberculosis activity, with an MIC value of 12.

New benzo[c]phenanthridine and benzenoid derivatives, and other constituents from Zanthoxylum ailanthoides: Effects on neutrophil pro-inflammatory responses.

A new benzo[c]phenanthridine, oxynorchelerythrine (1), and two new benzenoid derivatives, methyl 4-(2-hydroxy-4-methoxy-3-methyl-4-oxobutoxy)benzoate (2) and (E)-methyl 4-(4-((Z)-3-methoxy-3-oxoprop-1-enyl)phenoxy)-2-methylbut-2-enoate (3), have been isolated from the twigs of Zanthoxylum ailanthoides, together with 11 known compounds (4-14). The structures of these new compounds were determined through spectroscopic and MS analyses. Among the isolated compounds, decarine (4), (-)-syringaresinol (6), (+)-episesamin (8), glaberide I (9), (-)-dihydrocubebin (10), and xanthyletin (11) exhibited potent inhibition (IC50 values ≤ 4.

Biphenyl-type neolignans from Magnolia officinalis and their anti-inflammatory activities.

Reactive oxygen species (ROS) and granule proteases produced by human neutrophils contribute to the pathogenesis of inflammatory diseases. The MeOH extract of the stem bark of Magnolia officinalis showed potent inhibitory effects on superoxide anion generation and elastase release by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Five biphenyl-type neolignan derivatives, 5-allyl-5'-(1″-hydroxyallyloxy)biphenyl-2,2'-diol, 5,5'-diallyl-2'-(allyloxy)biphenyl-2-ol, 5,5'-diallyl-2'-(3-methylbut-2-enyloxy)biphenyl-2-ol, (E)-5-allyl-3'-(prop-1-enyl)biphenyl-2,4'-diol, and 4-allyl-2-(2'-methylbenzofuran-5'-yl)phenol, have been isolated from the stem bark of M.

Aporphine alkaloids and cytotoxic lignans from the roots of Illigera luzonensis.

Six aporphine alkaloids, (+)-(S)-N-butyrylcaaverine (1), (+)-(S)-N-propionylcaaverine (2), (+)-(S)-N-acetylcaaverine (3), (+)-(6aR,7R)-N-butyrylnorushinsunine (4), (+)-(6aR,7R,E)-N-(but-2-enoyl)norushinsunine (5), and N-formyldehydrocaaverine (6) were isolated from the roots of Illigera luzonensis, together with 16 known compounds. Their structures were determined through spectroscopic and MS analyses. Among the isolates, (-)-deoxypodophyllotoxin (13) was the most cytotoxic, with IC(50) values of 0.