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Analysis of the root extract of Peucedanum formosanum (Taiwan Qian-Hu) led to the isolation of 32 known compounds. The structures of these isolates were determined by spectral data. Some of them displayed strong anti-platelet aggregation activities. Analysis showed that most of the constituents found in P. formosanum were the same as those found in P. praeruptorum (Bai-Hua Qian-Hu), in that many isolates of both plants' roots belong to seselin-type dihydropyranocoumarins and psoralen-type furanocoumarins.

Two new triterpenoids, 2α,3β-dihydroxyolean-11,13(18)-dien-19β,28-olide (1) and 3β,5β-dihydroxyglutinol (2), together with eight known compounds (3–10) were isolated from the roots of Rhaphiolepis indica var. tashiroi (Rosaceae). The structures of 1–10 were determined by spectroscopic techniques. Among these isolates, 2α,3β-dihydroxyolean-13(18)-en-28-oic acid (9) exhibited inhibitory effect on N-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced superoxide production, with an IC50 value of 16.50 μM.

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.

Three new chromones, pisonins A (1), B (2), and D (4), two new flavonoids, pisonivanone [(2S)-5,7,2′-trihydroxy-8-methylflavanone] (7) and pisonivanol [(2R,3R)-3,7-dihydroxy-5,6-dimethoxyflavanone] (8), one new isoflavonoid, pisonianone (5,7,2′-trihydroxy-6-methoxy-8-methylisoflavone) (9), and five compounds first isolated from nature, namely, pisonins C (3), E (5), and F (6), pisoniamide (10), and pisonolic acid (11), together with 18 known compounds have been isolated from the methanol extract of the combined stem and root of Pisonia aculeata. Among these isolates, 2, 7, 14, 16, and 19 exhibited antitubercular activities (MICs ≤ 50.0 μg/mL) against Mycobacterium tuberculosis H37Rv in vitro.

Bioassay-guided fractionation of the methanolic extract of the roots of Rhaphiolepis indica var. tashiroi afforded four new dibenzofurans, 2-hydroxy-3,4,6-trimethoxydibenzofuran (1), 2-hydroxy-3,4,9-trimethoxydibenzofuran (2), 2-hydroxy-3,4,6,9-tetramethoxydibenzofuran (3), and 1,2-methylenedioxy-3,4,6-trimethoxydibenzofuran (4), two new biphenyls, 3-hydroxy-2',5-dimethoxybiphenyl (5) and 2',3-dihydroxy-5-methoxybiphenyl (6), and 3-hydroxy-5-methoxybiphenyl (7). Among the isolates, 3, 5, and 6 exhibited inhibitory effects on N-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced superoxide production, with in vitro IC50 values < 8.36 μM.

Androgen refractory prostate cancer is a major clinical challenge. Treatment approaches to prostate cancer are based on various mechanisms that cause malignant cell apoptosis. Of these strategies the anticancer effect of triggering death receptors is well substantiated.Several pharmacological and biochemical assays were used to characterize the apoptotic signaling pathways of the natural dihydrochalcone cryptocaryone in prostate cancer cells.Cryptocaryone induced antiproliferative and apoptotic effects in human androgen independent prostate cancer cells. It induced caspase-8 and 3 activation but did not change total protein levels of death receptors and their ligands. DR5 surface expression was moderately increased by cryptocaryone. Confocal immunofluorescence examination showed that cryptocaryone induced Fas clustering and the association of downstream signaling molecules, including FADD and procaspase-8. DR4 and DR5 aggregation was also induced by cryptocaryone. Data were confirmed by protein profile analysis of detergent resistant membranes showing that Fas, DR4, DR5, FADD and procaspase-8 levels were increased 1.3, 3.5, 4.1, 13.1 and 4.1-fold, respectively, in the lipid raft compartment. Cryptocaryone mediated clustering of death receptors and associated molecules was also detected in nonraft compartments. The distribution between lipid raft and nonraft compartments was validated by the cholesterol depleting agent methyl-beta-cyclodextrin. Cryptocaryone significantly potentiated FasL induced apoptosis in PC-3 cells.We suggest that cryptocaryone has anticancer activity via the stimulation of death receptor and associated molecule clustering, leading to caspase-8 and 3 activation, and apoptosis in prostate cancer cells.

Bioassay-guided fractionation of roots and stems of Ardisia virens Kurz (Myrsinaceae) led to isolation of fourteen compounds, (2'R)-6-(2'-acetoxypentadecyl)-5-hydroxy-2-methoxy-1,4-benzoquinone (1), (2'R)-6-(2'-acetoxytridecyl)-5-hydroxy-2-methoxy-1,4-benzoquinone (2), (2'R)-6-(2'-acetoxytridecyl)-2-methoxy-1,4-dihydroxybenzene (3), (2'R)-6-(2'-acetoxytridecyl)-5-formyl-2-methoxy-1,4-dihydroxybenzene (4), 1-(3,5-dihydroxyphenyl)nonan-1-one (5), 1-(3-hydroxy-5-methoxyphenyl)pentan-1-one (6), (2'S)-3-hydroxy-5-methoxyphenyl-2'-tridecanol (7), (2'S)-3-hydroxy-5-methoxyphenyl-2'-pentadecanol (8), (2'S)-5-acetoxy-3-hydroxyphenyl-2'-tetradecanol (9), 1-acetoxy-2-methoxy-6-pentadecyl-4-hydroxybenzene (10), 1-acetoxy-2-methoxy-6-tridecyl-4-hydroxybenzene (11), (2'R)-1-acetoxy-6-(2'-acetoxy-tridecyl)-2-methoxy-4-hydroxybenzene (12), (2'R)-1-acetoxy-6-(2'-acetoxypentadecyl)-2-methoxy-4-hydroxybenzene (13), and 1-acetoxy-6-(2'-ketopentadecyl)-2-methoxy-4-hydroxylbenzene (14), together with thirty-four other known compounds, of which three, 1-(3,5-dihydroxyphenyl)pentan-1-one (15), 1-(3,5-dihydroxyphenyl)heptan-1-one (16), and 1-(3,5-dihydroxyphenyl)pentadecan-1-one (17), were isolated for the first time from a natural source. Their structures were elucidated by analyses of spectroscopic data. Seven cytotoxic constituents were found to be 3, 10-12, ardisianone (18), cornudentanone (19), and ardisianol (31) with cytotoxic properties (IC(50) values < or =4 microg/mL) against MCF-7, NCI-H460 and SF-268 cancer cell lines in vitro.

Bioassay-guided fractionation of the root wood of Zanthoxylum wutaiense led to the isolation of 11 new compounds, wutaiensol methyl ether (1), demethoxywutaiensol methyl ether (2), methyl wutaiensate (3), methyl 7-hydroxyanodendroate (4), methyl 7-methoxyanodendroate (5), wutaifuranol (6), 7-methoxywutaifuranol (7), 7-methoxywutaifuranal (8), methyl wutaifuranate (9), methyl 7-methoxybenzofuran-5-carboxylate (10), and wutaipyranol (12), together with another 37 known compounds, of which one, 7-methoxybenzofuran-5-carboxaldehyde (11), was not previously known as a plant constituent. The structures of these isolates were identified by means of spectroscopic analysis. Five of these isolates were found to be antitubercular constituents, namely, methyl 7-methoxyanodendroate (5), 7-methoxywutaifuranal (8), wutaiensal (13), dictamnine (14), and gamma-fagarine (15), which exhibited antitubercular activity against Mycobacterium tuberculosis H37Rv, showing MIC values of 35, 35, 30, 30, and 30 microg/mL, respectively.

Investigation of the root extract of Antidesma pentandrum var. barbatum led to the isolation of seven new compounds, antidesmol (1), antidesmanins E (2) and F (3), antidesnone (4), antidesnol (5), barbatumols A (6) and B (7), together with 14 known compounds including sodium aristolochate-I (10) and aristolochic acid-I methyl ester (11).

Two new phenylpropanoids, integrifoliolin (1) and integrifoliodiol (2), together with 23 known compounds, have been isolated from the root wood of Zanthoxylum integrifoliolum. The structures of these compounds were determined by means of spectral analyses. The reported anti-HIV constituents of decarine and γ-fagarine were also isolated from the root wood of this plant.

Engelharquinone (1), engelharquinone epoxide (2), engelharolide (3), and engelhardic acid (4), were isolated as naturally occurring products from a plant source, Engelhardia roxburghiana together with 20 previously known compounds, four of which were hitherto not known as plant constituents. Their structures were identified by means of spectroscopic analysis. A biological evaluation showed that three of the previously isolated antitubercular constituents [(-)-4-hydroxy-1-tetralone, 3-methoxyjuglone and engelhardione] and engelharquinone (1) exhibited moderate antitubercular activity against Mycobacterium tuberculosis 90-221387.

Continuous investigation of the CHCl3-soluble and n-hexane fractions of the leaves of Litsea acutivena Hayata (Lauraceae) led to the isolation of one new butanolide, acutilactone (1), one new lactone, 4-nonacosyl-dihydrofuran-2-one (2), together with 15 known compounds. The known compounds included one butanolide, one norisoprenoid, one quinone, two steroids, one triterpenoid, one coumarin, two fatty acids, one amide, and five other compounds. The structures of these compounds were determined by means of spectral analyses.

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.

A steryl epoxide, machillene (1), a secobutanolide, secomahubanolide (2), and two butanolides, zuihoenalide (3), and 3-(1-methoxyoctadecyl)-5-methylene-5H-furan-2-one (4), together with 12 known compounds, were isolated from stem wood of Machilus zuihoensis. Their structures were determined by means of spectroscopic analyses. Machillene (1) showed cytotoxic activity against NUGC-3 and HONE-1 cancer cell lines in vitro.

Four new cerebrosides, gynuramides I˜IV (1-4), together with 37 known compounds were isolated from the rhizome of Gynura japonica. The structures of cerebrosides 1-4 were determined by chemical and spectroscopic examination to be: (2S,3S,4R,8E)-2-[(R)-2-hydroxypentacosanoylamino]-8-en-1,3,4-octadecanetriol, (2S,3S,4R,8E)-2-[(R)-2-hydroxytetracosanoylamino]-8-en-1,3,4-octadecanetriol, (2S,3S,4R,8E)-2-[(R)-2-hydroxytricosanoylamino]-8-en-1,3,4-octadecanetriol, and (2S,3S,4R,8E)-2-[(R)-2-hydroxydocosanoylamino]-8-en-1,3,4-octadecanetriol.

Four new coumarinolignans, antidesmanin A (=7-(1,1-dimethylallyl)-2,3-dihydro-3-(4-hydroxy-3,5-dimethoxyphenyl)-10-methoxy-2-methyl-6H-1,4,5-trioxaphenanthren-6-one; 1), antidesmanin B (=3,7-bis(1,1-dimethylallyl)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-10-methoxy-6H-1,4,5-trioxaphenanthren-6-one; 2), antidesmanin C (=2,7-bis-(1,1-dimethylallyl)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-10-methoxy-6H-1,4,5-trioxaphenanthren-6-one; 3) and antidesmanin D (=2-(3,4-dihydroxyphenyl)-3,7-bis(1,1-dimethylallyl)-2,3-dihydroxy-10-methoxy-6H-1,4,5-trioxaphenanthren-6-one or 3-(3,4-dihydroxyphenyl)-2,7-bis(1,1-dimethylallyl)-2,3-dihydro-10-methoxy-6H-1,4,5-trioxaphenanthren-6-one; 4) have been isolated from the root of the Formosan Antidesma pentandrum var. barbatum. The structures of these new compounds were elucidated by spectroscopic data. Compounds 1–3 exhibited marginal cytotoxicity against MCF-7 (breast) and SF-268 (CNS) cancer cell lines in vitro.

One new cinnamamide, beecheyamide (1) and one new lignan, (+)-beechenol (2), together with fifty-six known compounds, have been isolated from the stem of Zanthoxylum beecheyanum. The known compounds included seven coumarins, six benzo[c]phenanthridines, ten quinoline derivatives, five benzenoids, three aporphines, four amides, seven lignans, four steroids, one chlorophyll, five terpenoids, and five other compounds. The structures of these compounds were determined by means of spectral analyses. Several isolates exhibited significant antiplatelet activities.

Two new N-isobutylamides, hydroxy lanyuamide I (1) and hydroxy lanyuamide II (2), together with one hundred and ten known compounds, have been isolated from the root bark of Formosan Zanthoxylum ailanthoides. These known compounds include twenty coumarins, twenty-one benzo[c]phenanthridines, ten quinoline derivatives, one aporphine, one purine, seven amides, twelve benzenoids, one lactone, four flavonoids, nine lignans, eight steroids, two chlorophylls, eleven terpenoids and three other compounds, which were determined by means of spectral analyses.

Six new compounds, including the two long-chain esters balansenate I (=6,8,11-trimethyldodecanoic acid (2E)-3-methylhexadec-2-enyl ester; 1) and balansenate II (=10,12,15-trimethylhexadedecanoic acid (2E)-3-methylhexadec-2-enyl ester; 2), the eburicane-like triterpenoid bridelone (=hexadecahydro-4,4,10,13,14-pentamethyl-17-(5-methyl-1,4-dimethylenehexyl)-3H-cyclopenta[a]phenanthren-3-one; 3), the ‘deimino-xanthine', bridelonine (=5-(3-methylbut-2-enyl)pyrrolo[3,4-d]imidazole-4,6(1H,5H)-dione; 6), and the two adenine analogs 9-(3-methylbut-2-enyl)adenine (7) and 1-(3-methylbut-2-enyl)adenine (8), besides three known compounds, i.e., N6-(3-methylbut-2-enyl)adenine (4), 3-(3-methylbut-2-enyl)adenine (5), and adenine (9), were isolated from the leaves of Formosan Bridelia balansae. The novel skeleton of 6 consists of a fused pyrrolidine-2,5-dione and imidazole moiety. The already known adenines 7 and 8 were isolated for the first time from a plant. The structures of the isolated compounds were elucidated by spectroscopic analyses.

Bioassay-guided fractionation of the chloroform-soluble fraction from the stem wood of Formosan Lindera communis led to the isolation of two new cytotoxic butanolides, lincomolide C (1), lincomolide D (2), as well as two new secobutanolides, secolincomolide A (3), secolincomolide B (4), together with four known compounds, including one butanolide, isoobtusilactone A (5), and one secobutanolide, secoisolancifolide (6), one sesquiterpene, epi-cubenol (7), one steroid: beta-sitosterol (8). Compound 4 existed in enol [(2E)-2-[(1R)-1-hydroxy-2-oxo-propyl]-6,9-dimethyl-8-hydroxy-hexadec-2,7-dienoic acid methyl ester] (4a) and keto [(2E)-2-[(1R)-1-hydroxy-2-oxo-propyl]-6,9-dimethyl-8-oxo-hexadec-2-enoic acid methyl ester] (4b) tautomers. Compound 2 showed significant cytotoxicity against P-388 and HT-29 cancer cell lines. Also, 2 exhibited marginal activity against A549, 5 against P-388, and 1 against P-388, A549 and HT-29 cancer cell lines. Their structures were determined by spectroscopic analyses.

cis-Fagaramide (1), a new amide, together with fifty known compounds, have been isolated from the leaves of Zanthoxylum schinifolium. These known compounds include twenty-one coumarins, eleven alkaloids, one furan, four benzenoids, three chlorophylls, four triterpenoids, one diterpenoid, one sesquiterpenoid, and four steroids. The structures of these compounds were determined by means of spectral analyses.

Three new quinoline alkaloids, 2-acetylevolitrine (1), 2-acetylpteleine (2), and semecarpifoline (3), along with 26 known compounds were isolated from the root bark of Melicope semecarpifolia. The structures of 1-3 were elucidated by means of spectral analysis. In addition, (2S)-(--)-7,8-dimethoxyplatydesmine (4), cis-(+)-7,8-dimethoxymyrtopsine (5), and (3R)-(--)-8,9-dimethoxygeibalansine (6) were isolated as new natural products. Several of these isolates were determined as exhibiting significant antiplatelet aggregation activities in vitro.

Further investigations of the CHCl3-soluble fraction of the fruit of Zanthoxylum integrifoliolum led to the isolation of three new N-isobutylamides: lanyuamide IV (1), lanyuamide V (2), and lanyuamide VI (3), along with lanyulactone (4), a new butyrolactone derivative. The structures of these new compounds were elucidated by spectroscopic data.

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.

Further study on the chloroform-soluble portion of the root bark of Zanthoxylum schinifolium led to the isolation of eight new coumarins: methylschinilenol (1), hydroxyepoxycollinin I (2), 8-methoxyanisocoumarin H (3), hydroxyschininallylol (4), hydroxyepoxycollinin II (5), schinitrienin (6), schininallylone (7), and isoschinilenol (8), along with twenty-six known compounds including fourteen coumarins, and nine alkaloids. The structural elucidation was determined by spectroscopic data. Among the isolates, terpenyl-coumarins and furoquinolines were the active constituents with antiplatelet aggregation in vitro and collinin (10) showed significant anti-HBC DNA replication activity.

Examination of the leaves of Zanthoxylum integrifoliolum led to the isolation of a new bishordeninyl alkaloid, integramine, along with alfileramine, α-allocryptopine, pseudoprotopine and (+)-sesamin from the tertiary non-phenolic base fraction. The structures of these compounds were elucidated by spectral evidence.

Four new cytotoxic neolignans, machilusol A (1), machilusol C (3), machilusol D (4), machilusol E (5) as well as two new inactive neolignans, machilusol B (2) and machilusol F (6), were isolated from the stem wood of Machilus obovatifolia. All structures were identified by means of spectroscopic analysis.

Utilization of a novel carbanion-olefin intramolecular 6-endo-trig cyclization reaction to provide 2-aroyl-3,4-dihydro-2H-benzopyrans is described. Through a sequence of a Wittig reaction, O-alkylation, and carbanion-olefin intramolecular cyclization, salicylaldehydes were converted into a series of new 2-aroyl-3,4-dihydro-2H-benzopyrans in two steps or in one-pot reaction.

New syntheses of haginin E, equol, daidzein, and formononetin are described in this Letter. Through a sequence of a Wittig reaction, O-alkylation, and another Wittig reaction, 4-benzyloxysalicylaldehyde, which was prepared from resorcinol in two steps, was converted into the desired diene in one pot. Subsequently, the prepared diene was subjected to ring-closing metathesis using Grubbs’ catalyst (II) to construct the desired isoflavene intermediate. Using the prepared isoflavene, certain isoflavonoids such as haginin E, equol, daidzein, formononetin, and other related compounds were derived smoothly and in good overall yields.

Investigation of the fruit of Zanthoxylum integrifoliolum led to the isolation of three new isobutylamides, lanyuamide I–III and six known isobutylamides, tetrahydrobungeanool, γ-sanshool, hydroxy γ-sanshool, mixture of (2E,4E,8Z,11E)- and (2E,4E,8Z,11Z)-2′-hydroxy-N-isobutyl-2,4,8,11-tetradecatetraenamide and hazaleamide which was mixed with lanyuamide III. These amides were all with a (2E,4E)-dienamide moiety and their structures were elucidated on the basis of spectral analyses.

The genus Pourthiaea Decaisne (Rosaceae) belongs to subfamily Maloideae. There are about 20 species in temperate regions of eastern and southeastern Asia and the three species in Taiwan are Pourthiaea beauverdiana, Pourthiaea lucida and Pourthiaea villosa (Chang and Hartley, 1993). P. lucida is a small deciduous tree, endemic in Taiwan. The root of P. lucida Decaisne was collected in Mutan, Pingtung County, Taiwan, in April 2004. A voucher specimen (Chen, 6116) was deposited in the Herbarium of the School of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan, identified by Ih-Sheng Chen, corresponding author of this paper.

In this Letter, naturally occurring dalbergichromene and dalbergin were synthesized from a common neoflavene intermediate, which was derived from vanillin. The giving neoflavene intermediate was debenzylated with AlCl3 to yield dalbergichromene in 39% total yield, and it was oxidized by DDQ, and subsequently debenzylated by Pd(OH)2/C and cyclohexene in refluxing ethanol to give dalbergin in 31% total yield.

Four new butanolides, akolactone A, akolactone B, litseakolide A and litseakolide B, along with four known butanolides, litsenolide B 2 , litsenolide C 1 , litsenolide C 2 and hamabiwalactone A were isolated from the stem bark of Litsea akoensis . Their structures were elucidated from spectral evidence. These butanolides showed cytotoxic activity against P-388, KB16, A 549 and HT-29 cancer cell lines.

Four additional neolignans, comprising obovatifol [(2S,3S)-2,3-dihydro-2- (3,4-dihydroxy-5-methoxyphenyl)-7-methoxy-3-methyl-5-trans-propenyl benzofuran], obovaten [2-(3,4-dihydroxy-5-methoxyphenyl)-7-methoxy-3- methyl-5-trans-propenyl benzofuran], perseal C [(2S,3R)-2,3-dihydro-2-(3,4-methylenedioxyphenyl)-5- formyl-3-hydroxymethyl-7-methoxy benzofuran] and perseal D [2-(3,4-dihydroxy-5-methoxyphenyl)-5-formyl-7- methoxy-3-methyl benzofuran] were isolated in a continuing study of the leaves of Persea obovatifolia. Obovatifol had been reported previously in a mass spectrometric analysis without any other spectroscopic data. Obovaten and perseals C and D are new compounds, bearing a C-1' formyl side-chain, instead of a propenyl group. Their structures were elucidated from spectroscopic data; they showed significant cytotoxic activities against P-388, KB16, A549 and HT-29 cancer cell lines in vitro.

Continuing examination on the chloroform-soluble part of the bark of Zanthoxylum schinifolium , two new terpenyl coumarins, 7-(5′,6′-dihydroxy-3′,7′-dimethylocta-2′,7′-dienyloxy)-coumarin and 7-(2′,6′-dihydroxy-7′-methyl-3′-methyleneocta-7′-enyloxy)-8-methoxycoumarin, along with three coumarins, anisocoumarin H, 7-[( E )-7′-hydroxy-3′,7′-dimethylocta-2′,5′-dienyloxy]-coumarin, scopoletin; two alkaloids, 4-methoxy-1-methyl-2-quinolone and oxynitidine and a lignan, (+)-matairesinol, were isolated as additional constituents. The structures of these compounds were elucidated by spectral analyses. Among the isolates of the bark, collinin and oxynitidine showed significant activity of anti-HBV DNA replication. © 1997 Elsevier Science Ltd. All rights reserved

A new dibenzylbutyrolactone lignan, (−)-6′-hydroxyyatein, along with two new furanoid lignans, (−)-hernone [(2 R ,3 S ,4 R )-(−)-3-hydroxymethyl-4-(3″,4″,5″-trimethoxybenzoyl)-2-(3′,4′-dimethoxyphenyl) tetrahydrofuran] and (−)-nymphone [(2 R ,3 S ,4 R )-(−)-3-hydroxymethyl-4-(3″,4″,5″-trimethoxybenzoyl)-2-(3′,4′-methylenedioxyphenyl)tetrahydrofuran], have been isolated and characterized from the trunk bark of Formosan Hernandia nymphaeifolia . The structures of these compounds were determined by means of spectral analyses. These three lignans exhibited cytotoxic activities against P-388, KB16, A549 and HT-29 cell lines. © 1997 Elsevier Science Ltd. All rights reserved

Six new alkaloids, (+)-ovigerdimerine, 4-methoxyoxohernandaline, 7-formyldehydrohernangerine, 5,6-dimethoxy-N-methylphthalimide, 7-hydroxy-6-methoxy-1-methylisoquinoline and (+)-vateamine-2′-β-N-oxide, along with one new dialdehyde, hernandial, have been isolated and characterized from the trunk bark of Hernandia nymphaeifolia. The structures of these compounds were elucidated by spectral analyses.

Four new khellactone esters, (-)-trans-3'-acetyl-4'-senecioylkhellactone, (+-)-cis-3'-acetyl-4'-tigloylkhellactone, (+-)-cis-4-tigloylkhellactone, (+)-trans-4'-tigloylkhellactone, together with 14 known coumarins, isoimperatorin, psoralen, bergapten, xanthotoxol, cnidilin, (-)-selinidin, (-)-deltoin, (+)-pteryxin, (+)-peucedanocoumarin III, xanthotoxin, imperatorin, (+)-marmesin, (+)-oxypeucedanin hydrate, (+)-peucedanol and three chromones, eugenin, (-)-hamaudol, (+)-visamminol, have been isolated from the root of Formosan Peucedanum japonicum. The structures of the new compounds were elucidated by spectral data. The identities of (+)-trans-3'-tigloyl-4'-acetylkhellactone, formerly reported as a new compound, and (+)-cis-3'-angeloyl-4'-acetyl-khellactone, with the known (+)-peucedanocoumarin III and (+)-pteryxin, respectively, are discussed. Among the isolates, seven compounds, eugenin, (-)-selinidin, (+)-pteryxin, imperatorin, bergapten, cnidilin and (+)-visamminol, show strong antiplatelet aggregation activity in vitro.

Three new aporphine alkaloids, 7-formyldehydroovigerine, 7-formyldehydronornantenine and dehydrohernandaline, along with 10 known compounds, ( + )-ovigerine, ( + )-hernangerine, ( + )- N -methylhernangerine, N -methyl-6,7-dimethoxyisoquinolone, hernandonine, ( + )-malekulatine, isovanillin, backebergine, atheroline and ( + )-corytuberine, were isolated and characterized from the trunk bark of Hernandia sonora . The structures of these compounds were elucidated by spectral analyses.

Six new coumarins, schinicoumarin, acetoxyaurapten, epoxycollinin, schininallylol, schinilenol and schinindiol, along with seven known coumarins, aurapten, collinin, epoxyaurapten, hydrangetin, umbelliferone, acetoxycollinin and aesculetin dimethyl ether, three known alkaloids, norchelerythrine, dictamnine and skimmianine, and two triterpenoids, β-amyrin and friedelin, were isolated and characterized from the chloroform-soluble part of the bark of Zanthoxylum schinifolium . The structures of these compounds were elucidated by spectral analyses. Separation accompanied by bioassay-guided fractionation resulted in the isolation of seven compounds with strong inhibitory activity on platelet aggregation in vitro . These are schinicoumarin, acetoxyaurapten, schininallylol, aurapten, collinin, (−)-acetoxycollinin and dictamnine.

Two new butanolides, lincomolide A (1), lincomolide B (2), along with seven known compounds, isolinderanolide E, sepesteonol, beta-sitosterol, beta-sitosterol-beta-glucoside, tetradecane, nonanoic acid and decanol, were isolated from the chloroform-soluble portion of the stem bark of Lindera communis. Compound 1 showed cytotoxicity against P-388, KB16 and A549, and 2 exhibited cytotoxicity against P-388 cancer cell lines. Moreover, 1 showed marginal activity against HT-29, and 2 against KB16, A549 and HT-29 cancer cell lines. The structures of these compounds were determined by spectral analyses.

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.

A new phenolic furoquinoline alkaloid, evomerrine, was isolated from the leaves of Melicope semecarpifolia . Its structure was elucidated from spectral data and chemical evidence. Six other known furoquinoline alkaloids, platydesmine, skimmianine, kokusaginine, haplopine, heliparvifoline and confusameline, along with one flavonoid, ayanin, were also isolated.

Four new butanolides, akolactone A, akolactone B, litseakolide A and litseakolide B, along with four known butanolides, litsenolide B 2 , litsenolide C 1 , litsenolide C 2 and hamabiwalactone A were isolated from the stem bark of Litsea akoensis . Their structures were elucidated from spectral evidence. These butanolides showed cytotoxic activity against P-388, KB16, A 549 and HT-29 cancer cell lines.

Further investigations of the CHCl3-soluble fraction of the fruit of Zanthoxylum integrifoliolum led to the isolation of three new N-isobutylamides: lanyuamide IV (1), lanyuamide V (2), and lanyuamide VI (3), along with lanyulactone (4), a new butyrolactone derivative. The structures of these new compounds were elucidated by spectroscopic data.

Five new compounds, including a novel lactone, machilactone (=rel-(2R,3aR,6E,6aS)-2-heptadecyl-3a-methyl-6-octadecylidene-6,6a-dihydrofuro[2,3-d][1,3]dioxol-5(3aH)-one; 1), a new sesquiterpene, 3,4-dihydroxy-β-bisabolol (=rel-(1R,2S,4R)-1-[(1R)-1,5-dimethylhex-4-enyl]-1-methylcyclohexane-1,2,4-triol; 2), a new secobutyrolactone, methyl (2E)-2-(1-hydroxy-2-oxopropyl)eicos-2-enoate (3), two new butyrolactones, machicolide A (4) and machicolide B (5) (=3E,4R,5R)- and (3Z,4R,5R)-4,5-dihydro-4-hydroxy-5-methoxy-5-methyl-3-octadecylidenefuran-2(3H)-one, resp.) as a mixture, together with known caryophyllene oxide (=4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane), hexacosane, tetracosanoic acid, isomahubanolide-23 (=(3E,4R)-4,5-dihydro-4-hydroxy-5-methylidene-3-octadecylidenefuran-2(3H)-one), and β-bisabolol (=(1S)-1-[(1S)-1,5-dimethylhex-4-enyl]-4-methylcyclohex-3-en-1-ol) were isolated from the stem wood of Machilus zuihoensis. The structures of these compounds were established by spectroscopic studies. The eicos-2-enoate (3) and β-bisabolol exhibited marginal cytotoxicity against NUGC and HONE-1 cancer cell lines in vitro.

Utilization of a novel carbanion-olefin intramolecular 6-endo-trig cyclization reaction to provide 2-aroyl-3,4-dihydro-2H-benzopyrans is described. Through a sequence of a Wittig reaction, O-alkylation, and carbanion-olefin intramolecular cyclization, salicylaldehydes were converted into a series of new 2-aroyl-3,4-dihydro-2H-benzopyrans in two steps or in one-pot reaction.