Eupomatia Species Research Articles

ChemInform Abstract: Constituents of Eupomatia Species. Part 12. Isolation of Constituents of the Tubers and Aerial Parts of Eupomatia bennettii and Determination of the Structures of New Alkaloids from the Aerial Parts of E. bennettii and Minor Alkaloids

ChemInform Abstract: Constituents of Eupomatia Species. Part 12. Isolation of Constituents of the Tubers and Aerial Parts of Eupomatia bennettii and Determination of the Structures of New Alkaloids from the Aerial Parts of E. bennettii and Minor Alkaloids

ChemInform Abstract: Constituents of Eupomatia Species. Part 13. The Structures of New Lignans from the Tubers and Aerial Parts of Eupomatia bennettii.

ChemInform Abstract: Constituents of Eupomatia Species. Part 13. The Structures of New Lignans from the Tubers and Aerial Parts of Eupomatia bennettii.

Synthetic Studies of Imbiline 1 (I), a Constituent of Eupomatia Species.

Synthetic Studies of Imbiline 1 (I), a Constituent of Eupomatia Species.

Synthetic studies of imbiline 1, a constituent of Eupomatia species

Imbiline 1 ( 1a ), a constituent of Eupomatia species, was synthesized from 4-methoxy-1-naphthylamine hydrochloride ( 8 ) in seven steps. A reaction of aldehydes and methyl methylthiomethyl sulfoxide was also studied.

ChemInform Abstract: Constituents of Eupomatia Species. Part 11. New Eupodienone Lignans from the Flowers of Eupomatia laurina

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Chemical basis of a highly specific mutualism: Chiral esters attract pollinating beetles in Eupomatiaceae

Eupomatia species are pollinated exclusively by weevils of the genus Elleschodes (Col., Curculionidae), which may have their entire lifecycle linked to the host plant. Flowers produce potent fragrances, which serve as attractants for the weevils. Chemical analyses showed that the volatiles almost entirely consist of short chain, fatty acid esters; in E. laurina, methyl (2 S)-2-methylbutanoate made up over 97% of the fragrance, whereas methyl (2 R)-2-acetoxy-4-methylpentanoate dominates the blend in E. bennettii. In E. bennettii, qualitative and quantitative differences, including enantiomeric composition, were found between the sexual phases. The chemical nature of other weevil attractants, and functional properties of the floral esters are discussed.

Constituents of Eupomatia Species. XIII. The Structures of New Lignans From the Tubers and Aerial Parts of Eupomatia bennettii

The structures of new extractives from the tubers and aerial parts of Eupomatia bennettii F. Muell. have been assigned as follows: eupomatenoid-15, 2-(4′-methoxyphenyl)-3-methyl-5-(E)-propenylbenzofuran (1); eupomatenoid-16, 7-methoxy-2-(4′-methoxyphenyl)-3-methyl-5-(E)- propenylbenzofuran (3); eupomatenoid-17, 5-allyl-7-methoxy-2-(4′- methoxyphenyl)-3-methylbenzofuran (5); eupomatenoid-18, 5-allyl-2- (3′,4′-dimethoxyphenyl)-7-methoxy-3-methylbenzofuran (6). Eupobennettin was shown to be (2′α,3′α,4̸β,5′α)-5-[3′,4′-dimethyl-5′-(3′,4′,5′-trimethoxyphenyl)tetrahydrofuran-2′-yl]-2,3-dimethoxyphenol (7). Spectroscopic studies and a biomimetic synthesis proved that bennettinone was 2-(4′-allyl-2′-methoxyphenoxy)-1-(3′,4′-dimethoxyphenyl)propan-1-one (10).

Constituents of Eupomatia Species. XII. Isolation of Constituents of the Tubers and Aerial Parts of Eupomatia bennettii and Determination of the Structures of New Alkaloids From the Aerial Parts of E. bennettii and Minor Alkaloids of E. laurina

Extraction of the aerial parts of Eupomatia bennettii F. Muell . yielded liriodenine, eupomatenoid-1, -3, -5 and -6, eupodienone-4 and -6, and the new compounds eupomatenoid-15 and -16, eupobennettin, eupomatilone-1, -2, -3, -4, -5 and -6, and four alkaloids imbiline-1, -2 and -3 and eupomatidine-1. From the tubers, eupomatenoid-1, -3, -4, -5 and -6, eupodienone-4 and -6 were isolated along with new products eupomatenoid-15, -16, -17 and -18, bennettinone and eupomatilone-3, -4, -6 and -7. Chemical and spectroscopic evidence is used to assign the structures of imbiline-1 (1), imbiline-2 (3), imbiline-3 (5) and eupomatidine-1 (6). The previously reported alkaloids from E. laurina R. Br., EL base-4 and EL base-5, were shown to be mixtures of imbiline-1, -2 and -3, and of eupomatidine-2 (10) and eupomatidine-3 (11), respectively. 3-Methoxyeupolauridine (15) was isolated from eupolauridine mother liquors.

Constituents of Eupomatia Species. XI. New Eupodienone Lignans From the Flowers of Eupomatia laurina

On the basis of spectroscopic evidence, eupodienone-8 and -9, isolated from the flowers of Eupomatia laurina R. Br., are assigned the structures (5R, 7R, 8R)-3′,4-dimethoxy-7,8-dimethyl-2,3-methylenedioxy-6,7,8,9-tetrahydrospiro[5H-benzocycloheptene-5,1′-cyclohexa-2′,5′-dien]-4′-one (9) and (5S,7R,8R)-3′,4-dimethoxy-7,8- dimethyl-2,3-methylenedioxy-6,7,8,9-tetrahydrospiro[5H-benzocycloheptene-5,1′-cyclohex-2′,5′-dien]-4′-one (10) respectively. The products of dienone-phenol rearrangement of these substances are characterized; eupodienone-8 unexpectedly rearranges with aryl group migration. Eupomatenoid-1 and -7, eupodienone-6 and (-)- dihydroguaiaretic acid were also isolated.

Constituents of Eupomatia species. IX. N.M.R. evidence for the structure of eupolauramine and hydroxyeupolauramine

The 1H and 13C n.m.r. spectra of eupolauramine, 6-methoxy-5-methylbenzo[h]pyrrolo[4,3,2-de]-quinolin-4(5H)-one (3), have been assigned. Hydroxyeupolauramine was shown to be the 10-hydroxy derivative (4). The biogenesis of eupolauramine and eupolauridine (2) is discussed.

Constituents of Eupomatia species. X. The synthesis of 6-Methoxy-5-methylbenzo[h]pyrrolo[4,3,2-de]quinolin-4(5H)-one (eupolauramine)

Two syntheses of 6-methoxy-5-methylbenzo[h]pyrrolo[4,3,2-de]quinolin-4(5H)-one (eupolauramine) starting from 4-methoxynaphthylamine are described. One synthesis is highly efficient.

Constituents of Eupomatia species. VIII. The structures of eupodienone-4, -5,-6 and -7

On the basis of spectroscopic evidence structures (4), (5), (7) and (8) respectively are assigned to the neolignans eupodienone-4, -5, -6 and -7 isolated from Eupomatia laurina R.Br. The products of dienone-phenol and dienol-benzene rearrangement of the substances are characterized.

Constituents of Eupomatia species. VII. Dienone-phenol and dienol-benzene rearrangements in the eupodienone-1 series

Rearrangement of eupodienone-1 and derivatives, including certain dienols, under a variety of acidic conditions produced dibenzocyclooctene derivatives. Spectroscopic evidence and chemical degradation showed that in the rearrangements alkyl rather than aryl group migration had occurred. The stereochemistry of the products is discussed.

Constituents of Eupomatia species. VI. The structures of eupodienone-1, -2 and -3

Eupodienone-1, from the bark of Eupomatia laurina, has been shown by spectroscopic and degradative studies to have the novel neolignan structure (2), (7R,8S,9R)-9-acetoxy-2,3,3',4,5'-pentamethoxy-7,8- dimethyl-6,7,8,9-tetrahydrospiro[5H-benzocycloheptene-5,1'-cyclohexa- 2',5'-dien]-4'-one. Eupodienone-2 is the corresponding 9-hydroxy derivative (3) and eupodienone-3, the 9-benzoyloxy derivative (4). The substance EL3 is the 9-ethoxy derivative (5), an artefact.

Constituents of Eupomatia Species. V. The Isolation of Eupomatenoid-13 (a New Neolignan), (±)-trans-Dehydrodiisoeugenol, and Other Extractives from the Bark of Eupomatia laurina

A further extraction of the bark of Eupomatia laurina R. Br.from North Queensland yielded 17 substances: liriodenine, norushinsunine, β-sitosterol, eupomatenoid-1,-7 and -8, (�)-trans-dehydrodiisoeugenol(2), eupolauridine, eupolauramine and hydroxyeupolauramine, together with the seven new substances, eupomatenoid-13, eupodienone-4, -5, -6 and -7, and EL-base-4 and -5.Eupomatenoid-13 was shown to be 2-(4'-hydroxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran (1). Extraction of a sample of bark from New Guinea yielded eupolauramine, hydroxyeupolauramine, Β-sitosterol, eupomatenoid-1, -2, -3 and -11, and eupodienone-1, -2, -3, -4, -5, -6 and -7.

Constituents of Eupomatia species. IV. Structure and synthesis of eupolauridine (EL base-1) and some observations on the structures of eupolauramine (EL base-2) and hydroxyeupolauramine (EL base-3)

On the assumption that eupolauridine (EL base-1), eupolauramine (EL base-2) and hydroxyeupolaur-amine (EL base-3) were structurally related, a consideration of the spectral properties of the alkaloids suggested that eupolauridine was 3,4-diazafluoranthene. This base was synthesized but found to be different from eupolauridine. However, 1,6- diazafluoranthene, which was also synthesized, was identical with eupolauridine. With the two synthetic bases available in quantity it was possible to show that eupolauramine and hydroxyeupolauramine were not related to either of them.

Constituents of Eupomatia Species. 3. New Eupomatenoid Lignans From the Leaves and Wood of Eupomatia laurina

The leaves of Eupomatia laurina R.Br. gave seven substances previously isolated from the bark together with a flavone identified as 3,7,3?- trimethylquercitin, and the new lignans, eupomatenoid-9 and -10, which were shown to be erythro-5-(1?,2?-dihydroxypropyl)-2-(4?-hydroxy-3?- methoxyphenyl)-3-methylbenzofuran and 2-(4?-hydroxy-3?-methoxyphenyl)-3-methylbenzofuran-5-carbaldehyde, respectively. ��� The wood yielded seven substances which also occur in the bark, together with eupomatenoid-11 and -12, and eupodienone-2 and -3. Eupomatenoid-11 was found to be (R)-5-(2?-hydroxypropyl)-2-(3?,4?- methylenedioxyphenyl)-3-methylbenzofuran and eupomatenoid-12 to be the methyl ether of eupomatenoid-7.

Constituents of Eupomatia Species. II. Isolation and Structure Determination of Further Eupomatenoid Lignans From the Bark of Eupomatia laurina

A further extraction of the bark of Eupomatia laurina R.Br. has yielded 16 substances: liriodenine (as before), norushinsunine, three new bases, benzoic acid, sitosterol, eupodienone-1 (previously EL2; but not EL3 which is an artefact from EL2), eupomatene (ELl), and seven related substances. ��� The last eight substances, which are closely related, ere named ?eupomatenoids?. The structures of the eupomatenoids -2 to -8 have been established. Like eupomatenoid-1 (eupomatene), they are derivatives of 3-methyl-2-phenyl-5-(E)-propenylbenzofuran and are classified as lignans.

Constituents of Eupomatia species. The structure and synthesis of eupomatene, a lignan of novel type from Eupomatia laurina R. Br

The bark of Eupomatia laurina R. Br. yielded the known alkaloid, liriodenine, and four new substances. One of these, eupomatene, was shown by degradation to be 7-methoxy-3-methyl-2-(3?,4?- methylenedioxyphenyl)-5-trans-propenylbenzofuran. The dihydro derivative and eupomatene itself were synthesized. It is proposed that the term ?lignan? be extended to cover all natural products of low molecular weight that arise primarily from the oxidative coupling of p- hydroxyphenylpropene units and that eupomatene be then classified as a lignan. ��� A chlorotropolone has been isolated from a Reimer-Tiemann reaction on a simple phenol.