Furanocoumarins from Heracleum canescens

The ethanolic extract of the fresh roots of Heracleum canescens has afforded, besides sitosterol, osthol, methyl 3,4,5-trimethoxybenzoate and 11 furanocoumarins.     

Plant growth regulators from Heracleum lanatum

The plant growth regulating substances, pimpinellin, isopimpinellin, bergapten, isobergapten, vaginidiol, sphondin, scopoletin, umbelliferone, ferulic     

Furocoumarins from Angelica pachycarpa

A novel furocoumarin isolated from unripe fruits of Angelica pachycarpa has been characterized as (+)-tert- O-methylbyakangelicin. (+)-tert-O-Methyloxypeucedanin hydrate, neobyakangelicol, (±)-byakangelicol, (+)-byakangelicin, phellopterin, isoimperatorin, oxypeucedanin, oxypeucedanin hydrate, pangeline and umbelliprenin were also identified along with (±)-byakangelicin monoacetate, which proved to be an artifact.     

Steroids,chromone and coumarins from angelica officinalis

From the ethyl acetate extract of the fresh roots of Angelica officinalis var. himaliaca, besides sitosterol, pregnenolone, peucenin-7-methyl ether, osthol and 18 furanocoumarins have been characterized by spectroscopic methods, including ¹³C NMR, and some chemical transformations.     

Furanocoumarins in seeds of wild and cultivated parsnip

The furanocoumarin content of ripe seeds of seven cultivars of Pastinaca sativa was compared to that of ripe seeds from a naturalized population in central Illinois. Five furanocoumarins were identified and quantified in the intact seeds. While seeds of wild and cultivated plants contain furanocoumarin components in identical proportions, seeds from wild plants contain almost three times the quantity of furanocoumarins on a dry weight basis as do seeds of cultivars.     

Furanocoumarin biosynthesis in Ruta graveolens cell cultures

The biosynthetic routes to four linear furanocoumarins—psoralen, xanthotoxin, bergapten. isopimpinellin-co-occurring in Ruta graveolens cell cultures have been investigated with six ¹⁴C-labelled compounds. Mevalonic acid was only poorly incorporated, in contrast to umbelliferone. In support of previous suggestions, 7-demethylsuberosin and (±)-marmesin were very good precursors of the linear furanocoumarins. 7-O-Prenylumbelliferone also was fairly well utilized, but this was probably owing to a prior ether cleavage yielding umbelliferone. Psoralen was well incorporated into bergapten and xanthotoxin, but not into the dimethoxylated isopimpinellin. Differences exist between the organized plant and its cell culture in terms of metabolic products and, by implication, precursor utilization. S(+)-Marmesin was obtained in small quantity from an acid-hydrolysable conjugate present in the culture medium. Syntheses of [2-¹⁴C]7-demethylsuberosin, [2-¹⁴C]osthenol, [2-¹⁴C]7-O-prenylumbelliferone, [3-¹⁴C] (±)-marmesin, and [3-¹⁴C]psoralen are described, as well as an improved method for separation of furanocoumarin mixtures by TLC and GLC.     

Polyacetyleniques en C17 des racines d'Heracleum mantegazzianum

Heracleum mantegazzianum roots were examined for polyacetylenes. The structures of two compounds, n-cis-heptadecene-(9)-diyne-(4,6)-ol-(8) and n-trans-cis-heptadecadiene-(2,9)-diyne-(4,6)-ol-(8) are definitively established.     

Stereochemical aspects of the biological oxidation of aryl isoprenoids. The asymmetric synthesis and absolute configuration of meranzin and of meranzin hydrate

The role of epoxides in the biological oxidation of aryl prenyl derivatives is discussed in terms of the stereochemistry of quinoline alkaloids and coumarins found in species of the Rutaceae and Umbelliferae. Asymmetric synthesis of the epoxide, meranzin and of the diol, meranzin hydrate, have been carried out and the absolute configurations of the two coumarins have been established.     

Furanosesquiterpenes from the fruits of Smyrnium cordifolium

In addition to two known furanogermacranes, a new furanogermacrane and a new and highly unstable furanoeremophilane were obtained from the fruits of Smyrnium cordifolium. The latter compound could be the precursor of a number of eremophilanolides obtained from some other Smyrnium species.     

Sesquiterpene lactones from Smyrnium cordifolium

In addition to previously obtained furanosesquiterpenes, two new eudesmanolides and a new glechomanolide were isolated from the fruits of Smyrnium cordifolium, while the roots gave two new eudesmanolides. The new compounds from the fruits were 1β-acetoxy-eudesman-4(15), 7(11)-dien-8,12-olide, 1β-acetoxy-8β-hydroxy-eudesman-4(15),7(11)-dien-8,12-olide, 1β,10α;4α,5β-diepoxy-8-hydroxy-glechomanolide, those obtained from the roots were smyrnicordiolide and the corresponding 8β-hydroxy derivative belonging to a new type of oxepine derivative.     

Typification of the Boissier names in Anthriscus Pers. (Apiaceae)

Boissier described several taxa in Anthriscus , summarized in his Flora orientalis account. The names include A. lamprocarpa, A. kotschyi, A. ruprechtii, A. tenerrima, A. t. var. leiocarpa, A. anatolica, A. macrocarpa, A. nemorosa var. mollis, A. n. var. glabra; the hst four are still recognized as separate species. These names are typified in this paper, based on the material in Boissier herbarium at G.     

Coumarin constituents of Selinum tenuifolium

Three furocoumarins, bergapten, heraclenin and heraclenol have been isolated from the roots of Selinum tenuifolium (Umbelliferae). Another coumarin, m.p. 85–86°, isolated from the same source and provisionally designated as ST-1, has been proved to be mixture of imperatorin, and 8-geranyloxypsolaren by analyses of various reaction products and separation by preparative TLC on silica gel G impregnated with silver nitrate.     

Bacteriostatic activity of some coumarin derivatives

The bacteriostatic effect of some mono- and dihydroxy-coumarins and isopropyldihydrofuranocoumarins have been examined and compared with other simple phenols. Most of the coumarins proved to be far more bacteriostatic than the simple phenols.     

Volatile aroma constituents of parsley leaves

The aroma volatiles of a desert parsley were analysed using routine procedures, and 45 constituents were positively identified, including 11 not previously reported as parsley leaf volatiles. One component, 2-(p-tolyl)propan-2-ol, is a new aroma volatile and, together with p-mentha- 1,3,8-triene, may be unique to parsley. Major constituents of the sample were 4-methoxy-6-(prop-2-enyl)benzo-1,3-dioxolan (myristicin) 4,7-dimethoxy-5-(prop-2-enyl)benzo-1,3 dioxolan (apiole), β-phellandrene, p-mentha-1,3,8-triene and 4-isopropenyl-1-methylbenzene. Aroma assessments during GC showed that apiole, in particular, had desirable parsley odour character.     

7-Demethylsuberosin and osthenol as intermediates in furanocoumarin biosynthesis

¹⁴C-Labelled 7-demethylsuberosin (DMS) was a precursor of linear furanocoumarins in Conium maculatum and Heracleum lanatum (Umbelliferae), and in Ruta graveolens (Rutaceae), but not in Coronilla glauca (Leguminosae). Trapping experiments with ¹⁴C-umbelliferone over 3- to 24-hr periods revealed that DMS is rapidly metabolized, and that in short experiments its specific activity relative to the linear furano- coumarins′ is that of an intermediate. The specific activity of umbelliferone exhibited anomalies attributed to pool compartmentation. Analogous but less extensive experiments established that osthenol is an intermediate in angular furanocoumarin biosynthesis, but is much less rapidly metabolized than DMS. No significant incorporation into furanocoumarins of ¹⁴C from labelled l-valine, l-leucine, acetate, 2,3-di-hydroxyisovaleric acid, senecioic acid, isopentenylpyrophosphate, or mevalonate could be demonstrated. A synthesis of [1-¹⁴C]2,3-dihydroxyisovaleric acid is described.