Kazuko Kawanishi

Long chain esters of Virola species

Abstract The esters of n -fatty acids and ω-hydroxy n -fatty acids of β-sitosterol, D -glucose and ferulic acid ( trans and cis ) as well as β-sitosterol, fatty acids and β-sitosteryl-β- D -glucoside were isolated from three Virola species and identified by optical data and chemical reactions. A novel series of acidic esters derived from C 22 C 29 ω-hydroxy fatty acids and cis - and trans -ferulic acid is reported for the first time. These compounds also occurred as the corresponding diester 1-monoglycerides whereas the ω-hydroxy acids themselves were also present as the corresponding glucosyl esters.

Free primary alcohols in oils and waxes from germs, kernels and other components of nuts, seeds, fruits and cereals

The composition of free primary alcohols in oils and waxes obtained from the germ, kernel, seed coat, shell and skin (peel) of various nuts, seeds, fruits and cereals and from the chrysalis of silkworm was examined. These alcohols are usually present in small amounts, along with large quantities of hydrocarbons, esters and glycerides in oils and waxes. Thus, it is necessary to remove hydrocarbons, esters and glycerides to analyze the alcohols. We found that preparative reverse-phase thin-layer chromatography (TLC) was the best way to isolate alcohols from oils and waxes. Gas liquid chromatography (GLC) then detected hexacosanol, octacosanol and triacontanol in the oils and waxes. Octacosanol usually was the predominant alcohol. Relationships between the organs from nuts, seeds, fruits and cereals and the contents of octacosanol are suggested. For example, degermed kernels contained two times more octacosanol than the germ, and the skin coat and shell contained one-half and one-fortieth the octacosanol of the germ, respectively.

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

Abstract From the bark of Virola carinata two neolignans have been isolated: (−)-carcinatone, [(2 S )-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].

The neolignans, carinatidin, dihydrocarinatidin, carinatidiol and dehydrodieugenol B from Virola carinata

Abstract Seven neolignans have been isolated from the bark of virola carinata . Four more neolignans were found to be 5-allyl-7-methoxy-3-methyl-2-(3′-methoxy-4′-hydroxyphenyl)benzofuran, (2 S ,3 S )-5-allyl-7-methoxy-3-methyl-2-(3′-methoxy-4′-hydroxyphenyl)dihydrobenzofuran, threo -1-(3′,4′-dimethoxyphenyl)-2-(2″-methoxy-4″-allylphenoxy) propane diol (1, 3) and 4,5′-diallyl-2′-hydroxy-2,3′-dimethoxy diphenyl ether. The first three compounds were newly isolated and called carinatidin, dihydrocarinatidin and carinatidiol, respectively. The last one, known as dehydrodieugenol B, has been isolated before from Ocotea cymbarum .

Neolignans of Virola carinata bark

Abstract 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.

Dehydrodieugenol and its monomethyl ether from Virola carinata

Abstract The constituents of Virola carinata were established as dehydrodieugenol, its monomethyl ether and sitosterol.

Alkaloids from the hallucinogenic plant Virola sebifera

Abstract Bark of Virola sebifera used in the preparation of hallucinogenic snuffs and drinks in Venezuela has yielded N -methyl- N -formyltryptamine and N -methyl- N -acetyltryptamine, which exist in two rotameric forms reflecting hindered rotation around the carbon—nitrogen bond of the amide function. They were detected by HPLC as well as NMR. 2-Methyl-1,2,3,4-tetrahydro-β-carboline, N,N -dimethyltryptamine, its oxide and N -monomethyltryptamine were also identified.

Dihydrochalcones from Iryanthera sagotiana

Abstract Bark of Iryanthera sagotiana yields two dihydrochalcones; 2′,4′-dihydroxy-6′-methoxy-3,4-methylenedioxydihydrochalcone and 2′,4′-dihydroxy-4,6′-dimethoxydihydrochalcone, which were identified on the basis of their spectroscopic properties.

Separation of the pentacyclic triterpenes tylolupenols a and b from tylophora kerrii

Abstract Tylolupenols A and B from Tylophora kerrii were separated and identified as D:C-friedolup-8(9)-en-3β-ol and D:C-friedolup-9(11)-en-3β-ol, respectively.

Triterpenes from periandra dulcis roots

Three oleanane triterpenes were isolated from the roots of Periandra dulcis,and identified as 3β-hydroxy-25-al-olean-18-en-30-oic acid (periandric acid I), 3β-hydroxy-25-al-olean-12-en-30-oic acid (periandric acid II) and 3-oxo-25-hydroxy-olean-12-en-30-oic acid. The former two compounds (periandric acids I and II) were identical with the aglycones obtained by hydrolysis of periandrin I and II, respectively and the latter one was a new triterpene.