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PubMed1991

Steroidal and phenolic constituents of Lilium speciosum.

Phytochemical examination of the fresh bulbs of Lilium speciosum forma vestale has led to the isolation of a new phenolic glycoside and a new steroidal saponin. The respective structures of the new compounds have been shown by spectral analysis to be 6'-O-feruloylsucrose and (25R,26R)-26-methoxyspirost-5-en-3 beta-o1 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside. Several known phenolic glycosides and saponins have also been isolated and identified.

Acetylation↗
PubMed1992

Steroidal glycosides from the bulbs of Lilium dauricum.

The bulbs of Lilium dauricum yielded 11 compounds, including six new steroidal glycosides. The structures have been determined by spectral analysis and hydrolysis to be (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L-arabinopyranosyl-( 1----3)]- beta-D-glucopyranoside, (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----4)]- beta-D-glucopyranoside, (25R)-spirost-5-en-3 beta-ol (diosgenin) 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L-arabinopyranosyl- (1----3)]-beta-D-glucopyranoside, (25R)-3 beta,17 alpha-dihydroxy-5 alpha-spirostan-6-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside, (25R)-3 beta, 17 alpha-dihydroxy-5 alpha-spirostan-6-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L- arabinopyranosyl-(1----3)]-beta-D-glucopyranoside and (20R,22R)-3 beta,20,22-trihydroxy-5 alpha-cholestan-6-one (tenuifoliol) 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside. The absolute configurations of C-20 and C-22 of tenuifoliol were further confirmed by detailed analysis of the NOE difference spectrum of the corresponding isopropylidene derivative. Several known compounds were also isolated and identified.

Carbohydrate Sequence↗
PubMed1992

Jatropham derivatives and steroidal saponins from the bulbs of Lilium hansonii.

Two new jatropham derivatives and three new steroidal saponins were isolated from the fresh bulbs of Lilium hansonii, along with previously known compounds. The structures of the new compounds were elucidated, on the basis of spectroscopic data and chemical evidence, and by comparing them with those of known compounds, as (-)-5-hydroxy-3-methyl-3-pyrrolin-2-one (jatropham) 5-O-beta-D-glucopyranosyl-(1----3)-beta-D-glucopyranoside, (2S*,4R*)-1-(3-methyl-2-oxo-3-pyrrolinyl)-4-methyl-5-oxo-2-pyrr olidinecarboxyli c acid, 26-O-beta-D-glucopyranosyl-(25R)-5 alpha-furostan-3 beta,22 zeta-diol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----4)]- beta-D-glucopyranoside, (25R)-5 alpha-spirostan-3 beta,12 alpha-diol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----4)]- beta-D-glucopyranoside and (25R)-spirost-5-en-3 beta,12 alpha-diol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----4)]- beta-D-glucopyranoside, respectively. The stereostructure of jatropham dimer, the plain structure of which was presented previously, was confirmed by X-ray crystallographic analysis. The inhibitory activity on cyclic AMP phosphodiesterase of the steroidal saponins was evaluated.

3',5'-Cyclic-AMP Phosphodiesterases↗
PubMed1993

Steroidal saponins from the bulbs of Lilium regale and L. henryi.

Two new and three known steroidal saponins were isolated from the fresh bulbs of Lilium regale and two known saponins from those of L. henryi. The structures of the new saponins were established by extensive spectral data, hydrolysis and chemical correlation as (25R)-27-O-[(S)-3-hydroxy-3-methylglutaroyl]-spirost-5 -ene-3 beta,27-diol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]- beta-D-glucopyranoside and (25S)-spirost-5-ene-3 beta,17 alpha,27-triol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->2)-O- beta-D-glucopyranosyl-(1-->4)]-beta-D-glucopyranoside. Inhibitory activity of the saponins on cyclic AMP phosphodiesterase was evaluated.

3',5'-Cyclic-AMP Phosphodiesterases↗
PubMed1994

Steroidal saponins from the bulbs of Lilium longiflorum and their antitumour-promoter activity.

Two new spirostanol saponins and two new furostanol saponins were isolated from the fresh bulbs of Lilium longiflorum together with several known saponins. The structures of new compounds were determined to be (25S)-spirost-5-ene-3 beta, 27-diol 3-O-(O-alpha-L-rhamnopyranosyl-(1-->2)-O- [alpha-L-arabinopyranosyl-(1-->3)]-beta-D-glucopyranoside), (25R)-27-O-[(S)-3-hydroxy-3-methylglutaryl]-spirost-5-ene-3 beta,27 diol 3-O-(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[alpha-L-arabinopyranosyl -(1-->3)] - beta-D-glucopyranoside), 22-O-methyl-26-O-beta-D-glucopyranosyl-(25R)-furost-5-ene-3 beta,22 xi, 26-triol 3-O-(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[alpha-L- arabinopyranosyl-(1-->3)]-beta-D-glucopyranoside) and 22-O-methyl-26-O-beta-D-glucopyranosyl-(25R)-furost-5-ene-3 beta, zeta, 26-triol 3-O-(O-alpha-L-rhamnopyranosyl-(1 --> 2)- O-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-glucopyranoside). The isolated saponins and their derivatives were examined for inhibitory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to find new antitumour-promoter compounds.

Antineoplastic Agents, Phytogenic↗
PubMed1991

Subunit structure of the hemocyanins of some of the Muricidae and Fasciolariidae families: Chicoreus florifer dilectus (A. Adams), Muricanthus fulvescens (Sowerby), Urosalpinx cinerea (Say), Fascilaria lilium hunteria (Perry), and Pleuroploca gigantea (Kiener).

1. The hemocyanins of the Muricidae and Fasciolariidae families of marine gastropods: Chicoreus florifer dilectus, Muricanthus fulvescens, Urosalpinx cinerea, Fasciolaria lilium hunteria, and Pleuroploca gigantea were investigated by sedimentation velocity, scanning transmission electron microscopy, light-scattering, and other physical techniques. 2. The hemocyanins of these species are characterized by sedimentation coefficients close to 100 S and molecular weights of 8.2 x 10(6)-9.0 x 10(6). 3. The hemocyanins have di-decameric structures, with tail-to-tail arrangement of the decameric halves of the cylindrical particles. Only the hemocyanin of U. cinerea was found to contain about 30% higher, tri-, and tetra-decameric particles, with one or two decameric units added in a tail-to-head manner to a central di-decameric particle of the Mellema and Klug tail-to-tail arrangement. 4. The influence of pH, and the urea and Hofmeister salt series of reagents on the subunit structure and denaturation of P. gigantea hemocyanin were also investigated.

Animals↗
PubMed2005

Effect of cysteine on methionine production by a regulatory mutant of Corynebacterium lilium.

The production of methionine by submerged fermentation using a mutant strain of Corynebacterium lilium was studied to determine suitable conditions for obtaining high productivity. The mutant strain resistant to the methionine analogues ethionine, norleucine, methionine sulfoxide and methionine methylsulfonium chloride produced 2.34 g l(-1) of methionine in minimal medium containing glucose as carbon source. The effect of cysteine on methionine production in a 15 l bioreactor was studied by supplementing cysteine intermittently during the course of fermentation. The addition of cysteine (0.75 g l(-1)h(-1)) every 2 h to the production medium increased the production of methionine to 3.39 g l(-1). A metabolic flux analysis showed that during cysteine supplementation the ATP consumption reduced by 20%. It also showed that the increase in flux from phosphoenol pyruvate to oxaloacetate leads to higher methionine production. Results indicate that controlling the respiratory quotient close to 0.75 will produce the highest amount of methionine and that regulatory mutants also resistant to analogues of cysteine would be better methionine over producers.

Adenosine Triphosphate↗
PubMed1994

Steroidal saponins from the bulbs of Lilium speciosum x L. nobilissimum 'Star Gazer' and their antitumour-promoter activity.

The fresh bulbs of the oriental hybrid lily, Lilium speciosum x L. nobilissimum 'Star Gazer' yielded a new steroidal saponin, (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-[O-alpha-L-rhamnopyranosyl-(1-->2)-O-[6-O-acetyl-beta-D-glucopyranos yl- (1-->4)]-beta-D-glucopyranoside], along with four known steroidal saponins, (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-[O-alpha-L-rhamnopyranosyl-(1-->2)-O-]beta-D-glucopyranosyl-(1-->4)] - beta-D-glucopyranoside], (25R)-27-O-[(S)-3-hydroxy-3-methylglutaryl]- spirost-5-ene-3 beta, 27-diol 3-O-[O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D- glucopy-ranoside] and (25R)-27-O-[(S)-3-hydroxy-3-methylglutaryl]- spirost-5-eene-3 beta, 27-diol 3-O-[O-alpha-L-rhamnopyranosyl-(1-->2)-O- O-[beta-D-glucoyranosyl-(1-->4)]-beta-D-glucoyranoside]. The structure of The structure of the new saponin was determined by means of spectroscopic analysis and hydrolysis. The methyl ester of 5 showed potent inhibitory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated 32P incorporation into phospholipids of HeLa cells.

Antineoplastic Agents, Phytogenic↗
PubMed1999

Steroidal saponins from the bulbs of Lilium candidum.

Five new spirostanol saponins and a new furostanol saponin were isolated from the fresh bulbs of Lilium candidum. Their structures were elucidated on the basis of spectroscopic analysis, including two-dimensional NMR spectroscopic techniques and the result of acid hydrolysis. The isolated saponins contained a branched triglycoside moiety assigned as O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->6)]-beta - D-glucopyranose with the formation of an O-glycosidic linkage to C-3 of the aglycone as the common structural feature. The inhibitory activity of the saponins on Na+/K+ ATPase was evaluated.

Carbohydrate Conformation↗
PubMed2000

Decrease in the regeneration potential of long-term cell suspension cultures of Lilium formosanum Wallace and its restoration by the auxin transport inhibitor, 2,3,5-triiodobenzoic acid.

Cell suspension cultures of Lilium formosanum Wallace were initiated from bulb scale-derived calli and subcultured every 2 weeks using a medium containing 5 µM 4-amino-3,5,6-trichloropicolinic acid (picloram). Almost all cell clumps from the suspension cultures developed numerous somatic embryos following their transfer onto a plant growth regulator-free medium, while they vigorously produced shoot buds on media containing 0.5 or 5 µM 6-benzyladenine (BA). The high regeneration potential on a plant growth regulator-free medium was maintained for up to 54 months, but it gradually decreased thereafter, and only a few adventitious shoots and embryos were obtained from 75-month-old cultures. For restoring the regeneration potential of these cultures, various treatments with plant growth regulators were applied, among which about 10-fold increases in the number of regenerated shoot buds were obtained with 0.5 or 5 µM 2,3,5-triiodobenzoic acid (TIBA) in combination with 0.5 or 5 µM BA or N-(1,2,3-thiadiazol-5-yl)-N'-phenylurea (thidiazuron). Only shoot buds were produced from the cell clumps cultured on TIBA-containing media, and these shoot buds developed into complete plantlets after they were excised from the calli and transferred to a plant growth regulator-free medium.

Journal Article↗
PubMed1998

Organochlorine compounds from a terrestrial higher plant: structures and origin of chlorinated orcinol derivatives from diseased bulbs of Lilium maximowiczii.

Seven chlorine-containing orcinol derivatives (2-8) and orcinol (9) have been isolated from diseased bulbs of the edible lily Lilium maximowiczii, and their structures have been elucidated. Six of the chlorinated orcinol derivatives (2, 4-8) showed antifungal activity. Because organochlorine compounds are rare in terrestrial higher plants, their biosynthetic origin was examined. These compounds were shown to be induced in intact bulb scales by UV irradiation or by inoculation with the pathogenic fungus Fusarium oxysporum f. sp. lilii. Biosynthetic studies suggested that these "natural organochlorine pesticides" are produced by enzymatic chlorination of orcinol (9) with chloroperoxidase and hydrogen peroxide, which are both induced in the plant tissue under stress conditions.

Antifungal Agents↗
PubMed1999

Attachment of kinetochores to spindle microtubules during meiosis I of Lilium microsporocytes.

Kinetochores and microtubules were visualized simultaneously during spindle formation at the first meiotic division in microsporocytes of Lilium longiflorum (2n = 24) under a confocal laser-scanning microscope, after immunofluorescence staining with centromere-recognizing antiserum and tubulin-specific antibody. During early prometaphase I, each kinetochore of bivalent chromosomes appeared to be an amorphous flat structure upon its initial attachment to microtubules. It became compact and spherical with the development of the spindle. From late prometaphase I, when the bipolar spindle was nearly complete, each kinetochore resembled a double disk that was suggestive of a pair of sister kinetochores and the homologous kinetochores were oriented towards opposite poles. Thus, the bipolar spindle at metaphase I included 12 bivalent chromosomes with a total of four kinetochores each. At anaphase I, the sister kinetochores moved to the same spindle pole as a paired unit. In microsporocytes arrested at prometaphase I by colchicine treatment, the sister kinetochores also came to be distinguishable. These results suggest that the change of kinetochore structure during meiosis I may be under chromosomal control but be somewhat associated with its attachment to spindle microtubules.

Kinetochores↗
PubMed1999

Occupational IgE-mediated asthma, rhinoconjunctivitis, and contact urticaria caused by Easter lily (Lilium longiflorum) and tulip.

BACKGROUND: We report on IgE-mediated asthma, rhinoconjunctivitis, and contact urticaria to two Liliaceae plants, tulip and Easter lily (Lilium longiflorum), diagnosed in a floral shop worker. METHODS: Occupational asthma was diagnosed according to patient history, PEF monitoring, and a work-simulating provocation test. Flower-specific IgE was studied, and RAST inhibition tests were performed. RESULTS: Skin prick testing showed positive reactions to tulip, Easter lily, and chrysanthemum. Total IgE was 180 kU/I, and specific IgE to tulip was 2.6 and to Easter lily 6.5 kU/I. In the RAST-inhibition test, no cross-reactivity was found. Occupational asthma was diagnosed by peak flow monitoring at work and at home, as well as specific inhalation challenge with Easter lily, with an immediate 18% reduction in PEF. In addition, contact urticaria and conjunctivitis were diagnosed. After a 9-year follow-up without exposure to lilies, the skin prick tests to L. longiflorum and tulip were still positive, but the specific IgE had disappeared. CONCLUSIONS: A case of IgE-mediated occupational asthma, rhinoconjunctivitis, and contact urticaria caused by L. longiflorum and tulip is presented. RAST inhibition tests indicated concomitant sensitization to the two Liliaceae plants.

Allergens↗
PubMed1999

Partial purification and characterization of a novel endo-beta-mannosidase acting on N-linked sugar chains from Lilium longflorum thumb.

An enzyme catalyzing the hydrolysis of the Manbeta1-4GlcNAc linkage of N-linked sugar chains was partially purified and characterized. Endo-beta-mannosidase activity was detected using pyridylaminated (PA-) Manalpha1-6Manbeta1-4GlcNAcbeta1-4GlcNAc as the substrate in a homogenate of lily flowers (Lilium longflorum Thumb). The enzyme was partially purified by ammonium sulfate precipitation, and Q-Sepharose, Superdex 200, hydroxyapatite, Poros PE/M, Mono Q, and Superdex 200 column chromatographies. The optimum pH was 5.0 and the estimated molecular weight of the enzyme was 78,000, as determined by gel filtration. The Km value found for Manalpha1-6Manbeta1-4GlcNAcbeta1-4GlcNAc-PA was 1.4 mM. The enzymatic activity was not influenced by the addition of 10 mM EDTA or 2 mM Ca2+. Experiments on the hydrolysis of several PA-N-linked sugar chains revealed that the enzyme hydrolyzed MannManalpha1-6Manbeta1-4GlcNAcbeta1-4GlcNAc-PA (n = 0-2) into a mixture of MannManalpha1-6Man and GlcNAcbeta1-4GlcNAc-PA, indicating that it is an endoglycosidase in nature. However, the enzyme did not hydrolyze beta1-4mannohexaose or p-nitrophenyl beta-mannopyranoside.

Carbohydrate Metabolism↗
PubMed2000

A pollen-specific and desiccation-associated transcript in Lilium longiflorum during development and stress.

A cDNA clone encoding a desiccation-induced protein (LLA23) has been isolated from the mature pollen of a Lilium longiflorum cDNA library. Sequence analysis revealed significant similarity between the predicted LLA23 polypeptide, particularly at the C-terminal half of the sequence and a group of water-deficit/ripening-induced proteins. The expression of LLA23 gene is pollen-specific and the transcript accumulates only at the later stage of pollen maturation prior to anthesis. Premature drying of developing pollen confirmed that the accumulation of LLA23 transcripts was associated with desiccation. The LLA23 proteins decreased their levels when pollen/pollen tubes grew in the germination buffer. Treatments of pollen with abscisic acid (ABA) and polyethylene glycol (PEG)-8000 during germination greatly retarded the disappearance of LLA23 proteins and mRNAs. The LLA23 transcripts decreased their levels in pollen tubes grown both in vitro and in vivo, but the disappearance of LLA23 transcripts in tube cells grown in vivo was slower than those grown in vitro. In situ localization using anti-chicken immunoglobulin G conjugated with gold particles confirmed that LLA23 was located in the cytoplasm of pollen grains. The protective function of the desiccation-related proteins in the cytoplasm of pollen grains is proposed.

Amino Acid Sequence↗
PubMed2001

Relationship between the self-incompatibility and cAMP level in Lilium longiflorum.

The elongation of pollen tubes in Lilium longiflorum cv. Hinomoto after self-incompatible pollination stopped halfway, but that after cross-compatible pollination (cross with cv. Georgia) did not. The elongation of pollen tubes after self-pollination was enhanced by exogenous cAMP and by pertussis toxin or cholera toxin, which activates adenylate cyclase. The level of endogenous cAMP in pistils after self-pollination was approximately one half of that after cross-pollination. Furthermore, the activity of adenylate cyclase in pistils after self-pollination was also approximately one half of that after cross-pollination. By contrast, cAMP phosphodiesterase in pistils after self-pollination was approximately 2 times as high as that after cross-pollination. A possible correlation between self-incompatibility and the low level of endogenous cAMP in lily pistils is discussed on the basis of these results.

3',5'-Cyclic-AMP Phosphodiesterases↗
PubMed1993

Expression of the [beta]-Glucuronidase Gene in Pollen of Lily (Lilium longiflorum), Tobacco (Nicotiana tabacum), Nicotiana rustica, and Peony (Paeonia lactiflora) by Particle Bombardment.

A [beta]-glucuronidase (GUS) gene that is under the control of the anther-specific LAT52 promoter of tomato (Lycopersicon esculentum) and the nopaline synthetase polyadenylation terminator was successfully expressed in pollen of Lilium longiflorum, Nicotiana tabacum, Nicotiana rustica, and Paeonia lactiflora using a pneumatic particle gun. The GUS gene in plasmid pBI221 was also expressed, to a lesser extent, in pollen of all of these species. The presence of methanol in the substrate solution for histochemical GUS assay and the incubation time in this solution influenced successful detection of GUS expression in bombarded pollen. Cytological analysis of GUS-expressing pollen of lily showed that introduced gold particles were seen in intracellular compartments of pollen, including the vegetative cytoplasm, vegetative nucleus, and generative cytoplasm.

Journal Article↗
PubMed1994

Two classes of proteins and mRNAs in Lilium longiflorum L. indentified by human vitronectin probes.

Vitronectin (VN) is a substrate adhesion molecule, an extracellular matrix glycoprotein that facilitates cell adhesion and cell movement in animals. We have reported the cross-reactivity of a 55-kD protein in plants with rabbit anti-human VN antibodies and the presence of VN-like sequences in plant genomes using a human VN cDNA probe. We have extended these studies by using human VN riboprobes to detect VN-like mRNAs in lily (Lilium longiflorum L.) and soybean. In both species, two mRNAs were detected. We have also identified a new cross-reactive protein (41 kD) using a different preparation of human VN antiserum. In lily roots five 41-kD isoforms were observed, whereas only three of these isoforms accumulated in leaves. Monospecific antibodies prepared against the plant proteins cross-reacted with the human VN protein and vice versa. We have purified the 41-kD protein using two-dimensional gel electrophoresis, and amino acid composition analysis indicates that it is similar in composition to human VN.

Amino Acids↗