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Shikonin production by Lithospevmum cell cultures is induced by transferring the cells into production medium. Six phenolic compounds, p-hydroxybenzoic acid, caffeic acid, sinapic acid, ferulic acid, syringaldehyde, and salicyclic acid, were detected in both shikonin-producing and non-producing cells. Their contents in the former were much lower than those in the latter except for salicylic acid, the content of which strongly increased when cells were producing shikonin. The cell wall fraction, after alkaline hydrolysis, gave two phenolic compounds, p-hydroxybenzoic acid and caffeic acid. Their contents were much higher in shikonin-producing cells than in shikonin-free cells. Of these compounds, exogenous addition of p-hydroxybenzoic acid increased shikonin production in the production medium. Although it is a precursor of shikonin, the increment of shikonin produced was much larger than the administered p-hydroxybenzoic acid, suggesting this compound has a stimulatory effect on shikonin biosynthesis at a low concentration.

Various natural and synthetic compounds including alkaloids, terpenoids and phenolics were tested for inhibition of the cell surface expression of intercellular adhesion molecule-1 (ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1), both of which are crucial in the regulation of immune response and inflammation. Of 40 compounds tested, two compounds significantly downregulated the expression of VCAM-1 on murine endothelial cells (F-2) and ten compounds that of ICAM-1 on mouse myeloid leukemia cells (M1). Sanguinarine chloride (5) and isoliquiritigenin (13) were capable of lowering the levels of both ICAM-1 and VCAM-1. The structure-activity relationships study on chalcone and flavone derivatives related to 13 suggested that the inhibitory activity of the chalcone derivatives is attributable to the 4-hydroxy group as well as the possible coplanarity between the phenyl ring and the adjacent conjugated ketone.

This review deals with the biological aspects of monoterpene biosynthesis with special reference to the genetic nature of chemical variations (chemotypes) and a number of genes controlling biosynthetic reaction steps leading to the terpenoid components of essential oils in Perilla frutescens. Genetic analyses revealed the existence of two dominant genes of basic importance: gene G required for the induction of the whole monoterpene biosynthesis and gene H controlling a monoterpene cyclase (limonene synthase) necessary for the formation of cyclic monoterpenes. The nature and biochemical roles of these interesting genes are discussed in detail.

Traditional drugs used in the east Anatolia including Erzurum, Erzincan, Agri, Kars, Igdir, and Ardahan provinces have been surveyed. In this report, 169 remedies obtained from 87 plant species belonging to 38 families and 10 animal species are listed with their vernacular names, parts used, methods of preparing drugs, and traditional usages.

Methyl jasmonate, when administered to Lithospermum erythrorhizon cell suspension cultures, was found to induce the production of shikonin derivatives (the red naphthoquinone pigments of the root) and dihydroechinofuran (an abnormal metabolite of geranylhydroquinone). Culture experiments showed that methyl jasmonate caused a rapid increase in the activities of enzymes involved in the biosynthesis of shikonin such asp-hydroxybenzoate geranyltransferase, which was followed by the rapid accumulation of dihydroechinofuran and the delayed production of shikonin. The induction patterns observed were similar to those elicited by oligogalacturonides in Lithospermum cells, suggesting that jasmonic acid or its derivative may act as a signaling molecule in the elicitation of shikonin biosynthesis. Interestingly, however, the copper ion, which is essential for inducing shikonin biosynthesis by oligogalacturonides, was not required for shikonin induction by methyl jasmonate.

Two hundred and one folk remedies of West Anatolia derived from 91 plant species in 40 families and 2 animal species are presented, each with vernacular names, method of preparation of drugs and traditional uses.

An aqueous extract of the traditional herbal prescription, Zyumi-Haidoku-San-Ka-Rengyo (ZSR), was examined for antiallergic activity. Its oral administration to rats significantly inhibited homologous passive cutaneous anaphylaxis (PCA) induced by ovalbumin. The bioassay-directed fractionation of the extract followed by GC/MS analysis revealed that β-caryophyllene, a sesquiterpenoid component of the oil, was four times as active as the antiallergic drug tranilast against PCA induced in the ears of mice. β-Caryophyllene proved to be more effective than its structural isomer, α-humulene (α-caryophyllene), suggesting that the peculiar bicyclic system with four- and nine-member rings is of importance in enhancing the antiallergic activity of the sesquiterpene molecule.

Traditional medicine in the middle and west Black Sea regions: Amasya, Bilecik, Bolu, Cankin, Samsun, Sinop and Tokat provinces has been studied and 194 remedies obtained from 96 plant and 5 animal species are compiled. Vernacular names, parts used, methods of preparation, and medicinal usages are listed. Orta ve Bati Karadeniz Bolgelerinde Amasya, Bilecik, Bolu, Cankin, Samsun, Sinop ve Tokat illerinde halk tababeti incelenerek, 96 ’si bitkisel ve 5’i hayvansal olmak uzere 194 halk ilaci tespit edilmi§tir. Kullamlan materyalin mahalli ismi, tedavide kullanilan kisimlari, ilacin hazirlani§ §ekli ve tedavideki kullamli§ amaci He ilgili bilgiler liste halinde verilmi§tir.

A new chemotype (C type) ofPerilla frutescens (Labiatae) that accumulatestrans-citral as a main component of the essential oil in the leaf was crossed with five other chemotypes containing perillaldehyde (PA), elsholtziaketone (EK), perillaketone (PK), perillene (PL), and phenylpropanoid (PP) as their respective major components for comparison of genetic differences. The analyses of F1 and F2 progenies showed thattrans-citral is accumulated when its metabolism is blocked in the simultaneous absence of a dominant geneN, which is involved in the conversion oftrans-citral into naginataketone viacis-citral, and two polymeric genesFr 1 andFr 2 , which are involved in the conversion oftrans-citral into perillene. On the basis of new data obtained from various intercrosses involving the C type as one of the parents, the genotypes of different chemotypes as well as the sites of action of several genes controlling reaction steps in the biosynthesis of monoterpenes inPerilla have been revised.

Folk medicine in the inner region of the Taurus Mountains in south Anatolia has been studied; 256 remedies prepared from 124 plant and 3 animal species are listed. Data include vernacular names, the parts used, the methods of preparation of the drugs and the medicinal use.

S- Adenosyl- l -methionine (SAM): norcoclaurine 6- O -methyltransferase (NCMT), which controls berberine biosynthesis in Thalictrum minus cell cultures, was purified to homogeneity. The purified NCMT had a native M r of 72000 consisting of two subunits of 37000 each, a pH optimum of 9.0 and a p I of 4.3. The enzyme did not require Mg 2+ for activation, but was strongly inhibited by divalent cations of heavy metals and by SH reagents. Kinetic studies indicated a sequential mechanism with K m values of 56 μM for norcoclaurine and 260 μM for SAM. S- Adenosyl- l -homocysteine (SAH) was a potent inhibitor of NCMT and its K i value for SAH vs SAM was 89 μM.

Intracellular localization of p-O-β-d-glucosylbenzoic acid (PHBOG) and its aglycone, p-hydroxybenzoic acid (PHB), a key intermediate of shikonin biosynthesis, was investigated in Lithospermum erythrorhizon cell cultures. The glucoside, which is characteristically accumulated in shikonin-free Lithospermum cell cultures, proved to be localized mainly in the vacuoles of cells. p-Hydroxybenzoate glucosyltransferase, however, was not detected in the vacuoles but exclusively in the cytosol of cells. Furthermore, β-d-glucosidase, which hydrolyses PHBOG to yield PHB, was also located in the cytosol. These results suggest that PHB glucosylated in the cytosol is transported into the vacuole to be stored in a large quantity under protection from β-d-glucosidase in shikonin non-producing cells, until utilization as a precursor upon induction of shikonin biosynthesis.

14C-labelled l -phenylalanine administered to shikonin-producing cell cultures of Lithospermum erythrorhizon was incorporated rapidly into deoxyshikonin and then into fatty acid esters of shikonin. A gradual increase in the radioactivity of shikonin derivatives was accompanied by a decrease in that of deoxyshikonin. Furthermore, 14C-labelled deoxyshikonin supplied to cell cultures was incorporated into shikonin derivatives, e.g. acetyl- and β-hydroxyisovaleryl-shikonin, although 14C-labelled shikonin was hardly converted into shikonin derivatives. 14C-labelled deoxyshikonin incubated with a cell-free extract was also converted into esterified shikonin derivatives including acetylshikonin. These data strongly suggested that shikonin derivatives are biosynthesized from deoxyshikonin by hydroxylation and esterification at the C-1 position of its side chain both in cultured cells and in cell-free extracts of L. erythrorhizon.

Three forms of cytokinin-induced tetrahydroberberine (THB) oxidase from Thalictrum minus cell suspension cultures were individually separated by chromatography using DEAE-TOYOPEARL. Two of them were (S)-THB-specific oxidases, whereas the third was found to be a non-stereopecific one. The stereospecific oxidases were different from each other not only in the Km value, but also in the time course of activation induced by 6-benzylaminopurine (BAP). The substrate specificity of these oxidases from T. minus cells was more similar to that reported for the (S)-THB oxidase of Coptis japonica than that for Berberis stolonifera cell cultures.

Two new labdane diterpenoids, marrubinones A (1) and B (2), were isolated from aerial parts of Marrubium astracanicum collected in Turkey. Compounds 1 and 2 were mostly characterized by two-dimensional NMR. For determination of the absolute configuration, the modified Mosher's method was applied to the 12-hydroxy forms of 1 and 2. Compounds 1 and 2 are pentacyclic diterpenoids, which differ from each other only in the stereochemistry at C-13, and they were identified as 9α, 13S : 15, 16-diepoxy-12-oxo-14-labden-19, 6β-olide and 9α, 13R : 15, 16-diepoxy-12-oxo-17-labden-19, 6β-olide, respectively.

3H-Labelled berberine, a quaternary benzylisoquinoline alkaloid, was shown to bind specifically to a microsomal fraction prepared from cultured cells of Coptis japonica capable of accumulating the alkaloid in the vacuole. The Scatchard plot of the data suggested the existence of a single berberine-binding site with a dissociation constant (Kd) of 1.67 μM for berberine. The binding of [3H]berberine to the membrane fraction was reversible, the optimum pH for binding being between 9 and 10. An addition of either coptisine or jatrorrhizine, which are congeners of berberine, to the assay mixture significantly decreased [3H] berberine-binding, indicating that the binding is highly specific for protoberberine-type alkaloids indigenous to the C. japonica. An SH-blocking reagent, iodoacetate, as well as an excess amount of inorganic cation almost completely inhibited the binding. Further fractionation of the microsomes by sucrose density-gradient centrifugation suggested that the binding site was not associated with plasma membrane, endoplasmic reticulum or tonoplast, but with an unidentified membrane (ϱ = 1.08–1.10 g cm−3), which might be involved in the transport of berberine to the vacuole.

A field survey of traditional medicine in Turkey, specifically medicinal plants in East-Anatolia (Van-Bitlis Provinces), is discussed. Interviews with inhabitants, elder people, traditional practit...

18β-Glycyrrhetinic acid 24-hydroxylase activity was detected in the microsomal fraction prepared from Glycyrrhiza glabra cell suspension cultures. The enzymatic activity required both NADPH and O 2 . The participation of cytochrome P-450 in the reaction was demonstrated by inhibitor experiments including the light reversibility of CO inhibition. The 24-hydroxylation of 18β-glycyrrhetinic acid was shown to be prerequisite to forming its 3- O -glycoside by glucuronylation which is catalysed by a glucuronyltransferase localized also in the microsomal fraction of cultured licorice cells.

The effects of oligogalacturonides on the production of shikonin and its related metabolites as well as on enzyme activities involved in shikonin biosynthesis were investigated. Administration of oligogalacturonides (degree of polymerization; 12–20) to cell cultures of Lithospermum erythrorhizon rapidly activated the first half of the biosynthetic reactions which gave rise to a by-product, dihydroechinofuran via geranylhydroquinone. After a lag time, it promoted the latter half of the reactions, leading to the formation of shikonin from the key intermediate, geranylhydroquinone. Dihydroechinofuran production could be induced by oligogalacturonides irrespective of cell age, whereas shikonin production was inducible only when cells were over seven-days-old after inoculation. These results suggest that, even though the biosynthesis of the key intermediate is readily induced by oligogalacturonides, certain subcellular differentiation or aging is required for the formation of shikonin.

Cultured cells of Coptis japonica (Ranunculaceae) were shown to take up exogenously added, quaternary benzylisoquinoline alkaloids of the protoberb

Bryonolic acid, a pentacyclic triterpene having an anti-allergic activity, was biosynthesized from R-[2-14C]mevalonate or [2-14C]acetate administered to cell cultures of watermelon (Citrullus lanatus). The radioactivity of the labelled mevalonate added to cell-free extracts in the presence of ATP, Mg2+ and NADPH was also incorporated into bryonolic acid as well as into the possible intermediates, isomultiflorenol, bryonolol and bryonolal. Furthermore, [14C]2,3-oxidosqualene added to the microsomal solution of the same cell-free extracts was converted enzymatically into isomultiflorenol, which is considered to be the first cyclization product in the biosynthesis of bryonolic acid. These results indicate that bryonolic acid is biosynthesized from 2,3-oxidosqualene via isomultiflorenol and subsequent oxidations of the methyl group at C-29.

The traditional utilization of plants as medicine in the Mediterranean region has been investigated. Field surveys were carried out among the people who live in the Taurus Mountains. Sixty-nine medicinal plants have been identified, which are listed with the vernacular names, the parts used, the methods of preparing the drugs and their traditional usages.

The intracellular localization of p-hydroxybenzoate geranyltransferase, a key enzyme involved in shikonin biosynthesis in Lithospermum cell cultures was investigated. Fractionation of the microsomal components by continuous sucrose density gradient centrifugation showed that the enzyme was localized in a membrane fraction with a density of ϱ = 1.09– 1.10 g cm−3, which was distinctly different from those of the plastid and plasma membranes and tonoplast but was similar to that of the endoplasmic reticulum. Electron microscopic examination of the fraction having the p-hydroxybenzoate geranyltransferase activity revealed the presence of numerous vesicles (0.1–0.5 μm in diameter) which probably correspond to the secretion vesicles that are known to be derived from rough ER and responsible for excreting shikonin from the cells.

Cell suspension cultures of Luffa cylindrica, Citrullus lanatus, and related cucurbitaceous plants accumulate large quantities of bryonolic acid (3 beta-hydroxy-D:C-friedoolean-8-en-29-oic acid) [1], an acidic, pentacyclic triterpene found exclusively in the roots of the intact plants. This compound could readily be isolated from cultured cells with CHCl3 and purified simply by recrystallization. Pharmacological tests using mice demonstrated that bryonolic acid or its derivative is active against at least three types of allergies and that its activity could be increased significantly by preparing synthetic derivatives, in particular a potassium salt of its succinate ester. The biosynthesis of bryonolic acid from mevalonic acid via isomultiflorenol has been elucidated by tracer and enzymological experiments using cultured cells of watermelon both in vitro and in vivo. Furthermore, cell fractionation and electron microscopic studies on subcellular structures of luffa cells suggested that minute vesicles originating from elongated, rough endoplasmic reticulum probably play an important role in the transport of bryonolic acid which largely accumulates in the cell wall of cultured cells. The results obtained from the present study indicate that plant cell culture would be useful not only as a biological system for elucidating biosynthetic mechanisms but also as a potential source of new pharmacologically active compounds.

Shikonin biosynthesis in cell suspension cultures of Lithospermum erythrorhizon, which fails to occur under either white or blue light, proved to b

Two new labdane diterpenoids, marrubinones A (1) and B (2), were isolated from aerial parts of Marrubium astracanicum collected in Turkey. Compounds 1 and 2 were mostly characterized by two-dimensional NMR. For determination of the absolute configuration, the modified Mosher's method was applied to the 12-hydroxy forms of 1 and 2. Compounds 1 and 2 are pentacyclic diterpenoids, which differ from each other only in the stereochemistry at C-13, and they were identified as 9α, 13S : 15, 16-diepoxy-12-oxo-14-labden-19, 6β-olide and 9α, 13R : 15, 16-diepoxy-12-oxo-17-labden-19, 6β-olide, respectively.

The capability of cultured cells of Coptis japonica for accumulating a supersaturated solution of berberine (more than 70 mM) in vacuoles was investigated in relation to the solubility of various berberine salts. The results of experiments showed that the solubility of berberine is dependent on its paired anion, varying from 3 mM for nitrate to 640 mM for malate, suggesting that a high concentration of malic acid 168 mM found in the vacuole greatly contributes to the formation of a highly water-soluble salt of berberine. The production of berberine in cultured cells was accompanied by a steady increase of malic acid during the entire culture period. The present study has demonstrated an important role of a specific organic acid in solubilizing an excess of quarternary alkaloid in the vacuole.

Endogenous oligogalacturonides capable of inducing the biosynthesis of naphthoquinone pigments, shikonin derivatives, in cell cultures of Lithospermum erythrorhizon have been isolated and chemically elucidated. Analyses of the chemical composition and linkage of these sugars revealed that the active principle is an α-1,4-linked linear oligogalacturonide consisting of an average of 18 galacturonic acid units. Bioassays using a series of oligogalacturonides with various degrees of polymerization (2–15) indicated that the minimum degree of polymerization required for the induction of shikonin biosynthesis is 12.

The structures of seven triterpenoid metabolites including new compounds, 3-O-β-d-glucuronopyranosyl-24-hydroxy-18β-glycyrrhetinic acid and 24-hydroxy-18β-glycyrrhetinic acid 30-β-d-glucopyranosyl ester, derived from exogenous 18β-glycyrrhetinic acid administered to glycyrrhizin-free cell suspension cultures of Glycyrrhiza glabra, were determined. Studies on the time course of metabolism, as well as the pattern of chemical conversion of intermediate metabolites administered to cultured cells, showed that hydroxylation of the C-24 methyl group of 18β-glycyrrhetinic acid occurs as the first step of biotransformation, which is followed by glycosylation of the hydroxyl group at C-3 with glucuronic acid and arabinose, or by glucosylation of the C-30 carboxyl group. These results suggest a characteristic difference in the mode of glycosylation of 18β-glycyrrhetinic acid between liquorice roots and cultured cells of the same plant.

The activities of the two key enzymes involved in monoterpenoid biosynthesis, in various chemotypes of Perilla frutescens were examined to clarify the sites of action of two dominant genes, G and H, that are essential for the formation of cyclic monoterpenoids. GPP synthase activity was found in all chemotypes irrespective of the genotypes, but limonene synthase activity was found only in the PA chemotype (GGHH) that produces the cyclic monoterpenoid, perillaldehyde, as the main component of the essential oil. These results indicate that both genes, G and H, control separate enzymatic reactions in the cyclization of geranylpyrophosphate to yield limonene, a cyclic intermediate in the biosynthesis of perillaldehyde.

Twenty-one species or varieties of cucurbitaceous plants belonging to nine genera, and their cell cultures, were investigated with respect to their capability of producing bryonolic acid, a pentacyclic triterpene having anti-allergic activity. Bryonolic acid was found in all but two species, being localized exclusively in the roots of mature plants or in the radicles of seedlings. Tracer experiments using watermelon seedlings have shown that the radicle is the sole site of bryonolic acid biosynthesis in the seedling. On the other hand, cultured cells derived from bryonolic acid-containing plants were capable of producing a substantial amount of bryonolic acid, irrespective of the original organs used for callus induction.

The anti-allergic activity of bryonolic acid (1) isolated from the cultured cells of Luffa cylindrica L. (Cucurbitaceae) was compared with that of glycyrrhetinic acid (2), the aglycone of glycyrrhizin from licorice. Compound 1, when administered to rats intraperitoneally at a dose of 600 mg/kg, inhibited homologous passive cutaneous anaphylaxis more strongly than 2 at the same dose. Compound 1 also significantly inhibited delayed hypersensitivity in mice which could not be inhibited by 2. In contrast to 2, 1 showed not only little toxicity but no visible side effects on mice, without impairing the activity of the hepatic enzyme (4,5 beta-dihydrocortisone:NADP+ delta 4-oxidoreductase) involved in steroid catabolism.

Ethylene regulates berberine production in cell suspension cultures of Thalictrum minus , by activating the biosynthesis of berberine from the key intermediate ( S )-reticuline. In the late stage of culture, however, ethylene promoted the formation of bound polyphenolics, which was associated with cell browning.

The enzymatic formation of p -hydroxybenzoic acid from p -coumaric acid has been detected in cell free extracts of Lithospermum erythrorhizon cell cultures. In the absence of NAD, p -hydroxybenzaldehyde is formed instead of p -hydroxybenzoic acid. The reaction is specific to p -coumaric acid. In addition, a p -hydroxybenzaldehyde dehydrogenase activity is also found. The results suggest that the reaction mechanism is non-oxidative.

Inheritance of the color and the hardness of fruits was investigated in the progenies of intercrosses between two varieties, Egoma and Shiso, which belong to Perilla frutescens. The results of experiments showed that the fruit color (white vs. brown) is controlled by an incomplete dominant gene W, which is responsible for the thickening of the epidermal cell wall of pericarp. On the other hand, the hard fruit proved to be due to duplicate genes, T1 and T2, which cause the unusual thickening of the stone cell layer in pericarp.

Two biotransformation products formed from 18 beta-glycyrrhetinic acid by cell suspension cultures of Glycyrrhiza glabra were isolated and their structures determined by chemical and spectral data as 3-O-[alhpa-L-arabinopyranosyl-(1----2)-beta-D-Glucuronopy ranosyl]-24- hydroxy-18 beta-glycyrrhetinic acid and 30-O-beta-D-glycopyrano-syl-18 beta-glycyrrhetinic acid. The formation of glycyrrhizin, the main triterpene glucuronide of the licorice root, was not detected among the biotransformation products. This is the first report of the glucuronylation of an exogenous triterpene in plant cell cultures.

Cultured cells of Mallotus japonicus converted exogenous o -hydroxybenzoic acid into its O -glucoside after a lag period of 8 hr during which time the aglycone was taken up rapidly by the cells, partly excreted and then re-absorbed. The glucosylation of the aglycone into o - O -β- d -glucosylbenzoic acid began almost simultaneously with the induction of glucosyltransferase activity, and ca 78% of the aglycone administered was transformed into the glucoside in 12 hr. On the other hand, m - and p -hydroxybenzoic acids were glucosylated immediately after administration, the latter yielding both its O -glucoside and glucose ester. Inhibitor experiments suggested the possible participation of either 70S or 80S ribosomes in the glucosylation of isomeric hydroxybenzoic acids.

Soyasaponins were detected by GC and GC-MS in different organs of GLYCYRRHIZA GLABRA, particularly in the seed, hypocotyl and rootlet, whereas glycyrrhizin was detected exclusively in the thickening root and the stolon. An inverse relationship was found between the soyasaponins content and the glycyrrhizin content in the growing stolon and in the roots at different stages of growth.

Our field surveys on the traditional medicine in Turkey revealed that several plants are used for the treatment of ulcers; Cedrus libani, Centaurea solstitialis ssp. solstitialis, Cistus laurifolius, Hypericum scabrum, Plantago major, Sambucus ebulus and Spartium junceum. Various extracts prepared from these plants were tested by using a water immersion-stress ulcer model in rats to confirm the claimed activities. Pharmacological experiments clearly demonstrated that the aqueous extracts of all the plants given orally showed significant antiulcerogenic activity.

In the search for agents effective against immune-mediated disorders and inflammation, we have screened Malaysian medicinal plants for the ability to inhibit the expression of intercellular adhesion molecule-1 (ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) on the surface of murine endothelial cells (F-2), and mouse myeloid leukaemia cells (M1), respectively. Of 41 kinds (29 species, 24 genera, 16 families) of Malaysian plants tested, 10 and 19 plant samples significantly downregulated the expression of ICAM-1 and VCAM-1, respectively. Bioassay-directed fractionation of an extract prepared from the bark of Goniothalamus andersonii showed that its ingredients, goniothalamin (1) and goniodiol (2) inhibited the cell surface expression of both ICAM-1 and VCAM-1. The present results suggest that Malaysian medicinal plants may be abundant natural resources for immunosuppressive and antiinflammatory substances.

Lithospermum erythrorhizon cell suspension cultures in a growth medium produced no shikonin but an unusual metabolite, dihydroechinofuran (2-[4-(4-methyl-3-pentenyl)-2,5-dihydrofuran-2-yl]-1,4-benzoquinone), which is thought to be derived from geranylhydroquinone, a key intermediate in the biosynthesis of shikonin. This new compound was mostly released from the cells into the medium.

To study the genetic control of perillene formation in the glandular trichomes of Perilla frutescens, a novel chemotype (PL) containing perillene as a major component of the volatile oil was crossed with plants of the perillaketone (PK) and elsholtziaketone (EK) types. Analysis of F1 and F2 progenies showed that perillene is accumulated in plants lacking a dominant gene J which presumably controls the oxidative conversion of perillene into egonmaketone.

Cell suspension cultures of licorice (Glycyrrhiza glabra) have been shown to produce soyasaponins I and II, oleanane-type triterpene glycosides, which are known to exist in certain leguminous plants. The soyasaponin content in the licorice cell cultures varied from 0.017 to 1.1% of the dry weight of cells depending on culture strains and were also greatly influenced by plant growth hormones.

Incorporation of 14C-labeled sucrose, acetate, butyrate, and mevalonate into the terpenoid components of essential oils was examined using the detached cotyledons and foliage leaf discs of Perilla frutescens. Althought the radioactivity of sucrose administered was incorporated into the mono- and sesquiterpenoids of both tissues, that of acetate or butyrate was hardly detectable in the lower terpenoids of any foliage leaves except cotyledons. These results suggest that the conversion of acetyl CoA derived from fatty acids into lower terpenoids in the cotyledons does not occur in the foliage leaves.

From the aerial parts of Salvia nemorosa, three new megastigmane glycosides, salvionosides A-C, were isolated, along with the known compounds, (6S,9R)- and (6S,9S)-roseosides, (6R,9R)- and (6R,9S)-3-oxo-alpha-ionol glucosides and blumeol C glucoside. The structures of the new compounds were elucidated on the basis of spectral and chemical evidence. Copyright (C) 1996 Elsevier Science Ltd