Lignans from Nectandra turbacensis

Bark and wood of Nectandra turbacensis (Lauraceae) contain, besides the known furofuran lignans (+)-sesamin, (+)-demethoxyexcelsin and (+)-piperitol, the novel (1R,5R,2S,6S)-2-(3′-methoxy-4′,5′-methylenedioxyphenyl)-6-(4″-hydroxy-3″-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane [(+)-methoxypiperitol] and (1R,2S,5R)-2-(3′-methoxy-4′,5′-methylenedioxyphenyl)-3,7-dioxa-6-oxobicyclo[3.3.0]octane.     

Flavonoids from Iryanthera laevis

Trunk wood of Iryanthera laevis Markgr. (Myristicaceae) contains 2′,4′-dihydroxy- 4,6′dimethoxydihydrochalcone, three 2′-hydroxy-4′,5′-methylenedioxyflavans with differently substituted A-rings (7-OH-6,8-diMe; 7-OH-5,8-diMe; 5-OH-7-OMe-6,8-diMe) and 1-(2′-hydroxy-4′-methoxy-5′-methylphenyl)-3(2″-hydroxy-4″,5″-methylenedioxphenyl)- propane, as well as three additional known diarylpropanes.     

A substituted 1,2-diarylethane from Cymbidium giganteum

In addition to sitosterol and taraxerone, a new substituted 1,2-diarylethane, gigantol has been isolated from Cymbidium giganteum and characterized as 1-(3′-hydroxy-5′-methoxyphenyl-2-(4″-hydroxy-5″-methoxyphenyl)ethane on the basis of physicochemical data and through synthesis of its derivative.     

Dilignol glycosides from needles of Picea abies

(2R,3R)-2 3-Dihydro-2-(4′-hydroxy-3′-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-5-benzofuranpropanol 4′-O-β-d-glucopyranoside [dihydrodehydrodiconiferyl alcohol glucoside], (2R,3R)-2 3-dihydro-7-hydroxy-2-(4′-hydroxy-3′-methoxyphenyl)-3-(hydroxymethyl)-5-benzofuranpropanol 4′-O-β-d-glucopyranoside and 4′-O-α-l-rhamnopyranoside, 1-(4′-hydroxy-3′-methoxyphenyl)-2- [2″-hydroxy-4″-(3-hydroxypropyl)phenoxy]-1, 3-propanediol 1-O-β-d-glucopyranoside and 4′-O-β-d-xylopyranoside, 2,3-bis[(4′-hydroxy-3′-methoxyphenyl)-methyl]-1,4-butanediol 1-O-β-d-glucopyranoside [(?)-seco-isolariciresinol glucoside] and (1R,2S,3S)-1,2,3,4-tetrahydro-7-hydroxy-1-(4′-hydroxy-3′-methoxyphenyl)-6-methoxy-2 3-naphthalenedimethanol α²-O-β-d-xylopyranoside [(?)-isolariciresinol xyloside] have been isolated from needles of Picea abies and identified.     

Diarylpropanes from the wood of Iryanthera grandis

Trunk wood of Iryanthera grandis contains 1(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3″,4″-methylenedioxyphenyl)-propane and 1(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3″-methoxy-4″-hydroxyphenyl)-propane, as well as three additional known diarylpropanes, a new flavan (±)-5,7-dimethoxy-4′-hydroxyflavan and the known (±)-7,4′-dihydroxy-3′-methoxyflavan.     

Synthesis of dihydrochalcones of Myrica gale

4,4,6-Trimethyl-2-(3-phenylpropionyl)cyclohexane-1,3,5-trione, 2′-hydroxy-4′,6′-dimethoxy-3′-methyldihydrochalcone, 2′,6′-dihydroxy-4′-methoxy-3′,5′-dimethyldihydrochalcone and 2,2,5-trimethyl-4(3-phenylpropionyl)cyclopent-4-ene-1,3-dione, constituents of Myrica gale, have been synthesized.     

柯拉斯那沉香中2-(2-苯乙基)色酮类化学成分研究

为研究柯拉斯那(Aquilaria crassna Pierre ex Lecomte)沉香的化学成分。实验采用多种柱色谱方法从该沉香中分离得到9个2-(2-苯乙基)色酮类化合物,通过现代波谱学技术分别鉴定为6-甲氧基-2-[2-(3′-羟基-4′-甲氧基苯基)乙基]色酮(1)、5-羟基-6-甲氧基-2-[2-(3′-羟基-4′-甲氧基苯基)乙基]色酮(2)、tetrahydrochromone F(3)、6-甲氧基-2-[2-(3′-甲氧基-4′-羟基苯基)乙基]色酮(4)、6-甲氧基-7-羟基-2-[2-(4′-甲氧基苯基)乙基]色酮(5)、6,7-二甲氧基-2-[2-(3′-羟基-4′-甲氧基苯基)乙基]色酮(6)、6,7-二甲氧基-2-[2-(4′-甲氧基苯基)乙基]色酮(7)、6-羟基-2-[2-(4′-羟基苯基)乙基]色酮(8)、5-羟基-2-[2-(2′-羟基苯基)乙基]色酮(9)。化合物2、3和5～9均为首次从柯拉斯那所得沉香中分离得到。采用MTT法对单体化合物的细胞毒活性进行测试,测试结果表明,化合物1,2和4具有微弱的细胞毒活性。     

Neolignans from Nectandra miranda

Seven neolignans, isolated from a C₆H₆ extract of Nectandra miranda (Lauraceae) trunk wood, included the hitherto undescribed (2S, 3S, 3aS)- and (2S, 3S, 3aR)-5-allyl-3a-methoxy-2-(3′, 4′, 5′-trimethoxyphenyl)-3-methyl-2, 3, 3a, 6-tetrahydro-6-oxobenzofurans (respectively mirandin-A and mirandin -B), 7-allyl-6-hydroxy-5-methoxy-2-(3′, 4′, 5′-trimethoxyphenyl)-3-methylbenzofuran and (2R, 3R)-7-methoxy-2-(3′, 4′, 5′-trimethoxyphenyl)-3-methyl-5 -(E)-propenyl-2, 3-dihydrobenzofuran (licarin C).     

Neolignans of Virola carinata bark

Four neolignans, dehydrodieugenol, its monomethylether, carinatone and carinatin have been isolated from the hexane fraction of the bark of Virola carinata. Three new neolignans were separated from the chloroform fraction and examined by spectroscopy and chemical reactions. Their structures were determined as (2S, 3S)-5-allyl- 7-methoxy-3-hydroxymethyl-2-(3′,4′-dimethoxyphenyl)-2,3-dihydrobenzofuran, (2S)- 1-(3′,4′-dimethoxyphenyl)-2-(3″-allyl-5″-methoxy-6″-hydroxyphenyl)propanone(1) ol(3), (1S,2S)-1-(3′,4′-dimethoxyphenyl)-2-(3″-allyl-5″-methoxy-6″-hydroxyphenyl) propanol(1) and called dihydrocarinatinol, carinatonol and carinatol, respectively.     

The neolignans (−)-carinatone and carinatin from Virola carinata

From the bark of Virola carinata two neolignans have been isolated: (?)-carcinatone, [(2S)-1-(3′,4′-dimethoxyphenyl)-2-(3″-allyl-5″-methoxy-6″-hydroxyphenyl) propanone] and carinatin, [5-allyl-7-methoxy-3-methyl-2-(3′,4′-dimethoxyphenyl)benzofuran].     

Diarylpropanoids from Iryanthera polyneura

The trunk wood of Iryanthera polyneura Ducke (Myristicaceae) contains pinocembrin, 1-(2′,4′-dihydroxyphenyl)-3-(3″,4″-methylenedioxyphenyl)-propane, 1-(2′,4′-dihydroxy-3′-methylphenyl)-3-(2″-methoxy-4″, 5″-methylenedioxyphenyl)-propane and 4,2′,4′-trihydroxy-3-methoxydihydrochalcone.     

Phenols bromes d'une algue rouge, Halopytis incurvus: Acides carboxyliques

Extracts of Halopytis incurvus yielded, after methylation, the esters of 3,5-dibromo-4-methoxy-phenylacetic acid and 2-methoxy-3-(3′,5′-dibromo-4′-methoxyphenyl)acrylic acid.     

Bicyclo[3,2,1]octanoid,neolignans from Aniba simulans

Six bicyclo[3,2,1]octanoid neolignans, isolated from the benzene extract of Aniba simulans Allen (Lauraceae) trunk wood, are shown to derive from two basic structures: 1-allyl-8-hydroxy-6-(3′-methoxy-4′,5′-methylenedioxyphenyl)-7-methyl-3-oxobicyclo[3,2,1]octane, substituted by 4-hydroxy, 4-hydroxy-5-methoxy, 4-methoxy or 4,5-dimethoxy groups; and 1-allyl-8-hydroxy-6-(3′-methoxy-4′,5′-methylenedioxyphenyl)-7-methyl-4-oxobicyclo[3,2,1]oct-2-ene, substituted by 3-hydroxy or 3-hydroxy-5-methoxy groups. The structural proposals are based on spectral data, interconversions synthesis of a derivative from the known (2R,3S,3aS)-3a-allyl-5-methoxy-2-(3′-methoxy,4′,5′-methylenedioxyphenyl)-3-methyl-2,3,3a,6-tetrahydro-6-oxobenzofuran.     

Xanthones from Tovomita pyrifolium

The wood of Tovomita pyrifolium (Guttiferae) contains the novel tovopyrifolins A [1,6-dihydroxy-7-methoxy-5-prenyl-6′,6′-dimethylpyrano (2′,3′:3,2)xanthone], B (1,5-dihydroxy-3,4-dimethoxyxanthone) and C (1,3,5-trihydroxy-2-methoxyxanthone) and also the known tovophyllins A and B [structure revised to 1,6-dihydroxy-5-prenyl-6′, 6′-dimethylpyrano(2′,3′:3,2)-6″,6″-dimethylpyrano(2″,3″:7,8)xanthone].     

A chalcone and an isoflavone from Millettia pachycarpa seeds

Chemical examination of the seeds of Millettia pachycarpa has yielded a new prenylated isoflavone and a new prenylated chalcone in addition to the previously reported isoflavones 5-hydroxy-4′-methoxy-6″,6″-dimethylpyrano (2″,3″:7,8)isoflavone, 5,7,4′-trihydroxy-6,8-diprenylisoflavone, 5,7,3′,4′-tetrahydroxy-6,8-diprenyl-isoflavone and pomiferin.     

Benzofuranoid neolignans from Aniba simulans

Forteen neolignans, isolated from the benzene extract of Aniba simulans (Lauraceae) trunk wood, included the hitherto undescribed (2S, 3S, 5R)-5-allyl-5,7-dimethoxy-2-(3′,4′,5′-trimethoxyphenyl)-3-methyl-2,3,5,6-tetra-hydro-6-oxobenzofuran, (2R,3S,5R) -5-allyl-5-methoxy-2-(3′-methoxy-4′,5′-methylenedioxyphenyl)-3-methy1-2,3,5, 6-tetrahydro-6-oxobenzofuran, (2S,3S)-6-O-allyl -5-methoxy-2-(3′-methoxy-4′-5′-methylenedioxyphenyl)-3-methyl-2,3-dihydrobenzofuran, (2R,3S)-6-O-allyl-5-methoxy-2- (3′-methoxy-4′,5′-methylenedioxyphenyl)-3-methyl-2,3-dihydrobenzofuran and 7-allyl-6-hydroxy-5-methoxy-2-(3′-methoxy-4,5′ -methylenedioxyphenyl)-3-methylbenzofuran.     

Macrophyllin,a neolignan from Licaria macrophylla

The trunk wood of Licaria macrophylla (A. C. Smith) Kosterm. (Lauraceae) contains, in addition to sitosterol, terpene (borneol) and sesquiterpene (nerolidol, elemol) alcohols, a novel neolignan, macrophyllin, for which the structure of 3-allyl-8-hydroxy-1,5-dimethoxy-7-methyl-4(or 2)-oxo-6-(3′,4′-methylenedioxy-5′-methoxyphenyl)-bicyclo [3,2,1] oct-2(or 4)-ene is proposed.     

Neolignans from an Aniba species

The trunk wood of an Amazonian Aniba (Lauraceae) species contains, besides dillapiol and the benzodioxane-type neolignan eusiderin, four bicyclo(3.2.1)octanoid neolignans. These comprise representatives of the canellin-type: the known methoxycanellin-A and the novel compounds characterized as (1R, 3S, 4S, 5S, 6S, 7R)-1-allyl-4-hydroxy-3, 5-dimethoxy-7-methyl-6-(3′-methoxy-4′, 5′-methylenedioxyphenyl)-8-oxo-bicyclo(3.2.1)octane; (1R, 3S, 4S, 5S, 6S, 7R)-1-allyl-4-hydroxy-3, 5-dimethoxy-7-methyl-6-(3′, 4′, 5′-trimethoxyphenyl)-8-oxobicyclo(3.2.1)octane and (1R, 4R, 5R, 6S, 7R, 8S)-1-allyl-4, 8-dihydroxy-5-methoxy-7-methyl-6-(3′-methoxy-4′,5′-methylenedioxyphenyl)-3-oxobicyclo(3.2.1)octane.     

Four new coumarins from the roots of Peucedanum arenarium

The roots of Peucedanum arenarium var. arenarium revealed the presence of 4 new natural coumarins. By spectral data their structures were elucidated as follows: peuarin, 3′-angeloyl-4′-methylisokhellactone; peuchlorin, 3′-angeloyl-4′-(2″-hydroxy-2″-methyl-3″-chloro)-butyroylisokhellactone; peuchlorinin, 3′-(2″-methylepoxy)-butyroyl-4′-(2″-hydroxy-2″-methyl-3″-chloro)-butyroylisokhellactone; peucloridin 3′,4′-di-(2″-hydroxy-2″-methyl-3″-chloro)-butyroylisokhellactone.     

Neolignans from Aniba burchellii

Seven neolignans, isolated from the benzene extract of Aniba burchellii Kosterm. (Lauraceae), included the hitherto unknown (2S,3S,5S)-5-allyl-5-methoxy-3-methyl-2-(3′,4′-methylenedioxyphenyl)-2,3,5,6-tetrahydro-6-oxobenzofuran and (1R,5R,6R,7R)-1-allyl-6-(4′-hydroxy-3′-methoxyphenyl)-3-methoxy-7-methyl-4,8-dioxobicyclo-[3,2,1]oct-2-ene. The former structure was previously assigned to a constituent of A. terminalis Ducke which is in fact the 5R-epimer. In addition to the latter constituent, all other previously described 4-oxobicyclo[3,2,1]oct-2-ene neolignans had their absolute configuration established.