Ulva and Enteromorpha are cosmopolitan and familiar marine algal genera. It is well known that these green macroalgae lose their natural morphology during short-term cultivation under aseptic conditions and during long-term cultivation in nutrient-added seawater and adopt an unusual form instead. These phenomena led to the belief that undefined morphogenetic factors that were indispensable to the foliaceous morphology of macroalgae exist throughout the oceans. We characterize a causative factor, named thallusin, isolated from an epiphytic marine bacterium. Thallusin induces normal germination and morphogenesis of green macroalgae.

Many green algae cannot develop normally when they are grown under axenic conditions. Monostroma oxyspermum, for example, proliferates unicellularly in an aseptic culture, but develops into a normal foliaceous gametophyte in the presence of some marine bacteria. More than 1000 bacterial strains were isolated from marine algae and sponges and assayed for their ability to induce the morphogenesis of unicellular M. oxyspermum. Fifty bacterial strains exhibiting morphogenesis-inducing activity against unicellular M. oxyspermum were isolated. The partial gyrB (approximately 1.2 kbp) and 16S rDNA (approximately 1.4 kbp) sequences of about 40 active strains were determined, and their phylogenetic relationships were analysed. All these strains were located within the Cytophaga-Flavobacterium-Bacteroides (CFB) complex, and most of these strains were clustered in a clade comprising Zobellia uliginosa. On the other hand, these bacteria also exhibited morphogenetic activity against germ-free spores of Ulva pertusa, Ulva conglobata and Enteromorpha intestinalis. Moreover, these bacteria induced the release of spores from the leafy young gametophyte of M. oxyspermum. These results indicate that strains belonging to several groups in the CFB complex play an important role in the normal development of green algae in the marine coastal environment.

We isolated three orange or yellow pigment-producing marine bacteria, strains 04OKA-13-27 (MBIC08261), 04OKA-17-12 (MBIC08260), and YM6-073 (MBIC06409), off the coast of Okinawa Prefecture in Japan. These strains were classified as novel species of the family Flavobacteriaceae based on their 16S rRNA gene sequence. They were cultured, and the major carotenoids produced were purified by chromatographic methods. Their structures were determined by spectral data to be (3R)-saproxanthin (strain 04OKA-13-27), (3R,2'S)-myxol (strain YM6-073), and (3R,3'R)-zeaxanthin (strains YM6-073 and 04OKA-17-12). Saproxanthin and myxol, which are monocyclic carotenoids rarely found in nature, demonstrated significant antioxidative activities against lipid peroxidation in the rat brain homogenate model and a neuro-protective effect from L-glutamate toxicity.

A new cytotoxic substance named mechercharmycin A was isolated from marine-derived Thermoactinomyces sp. YM3-251. The structure of mechercharmycin A was determined by an X-ray crystallographic analysis to be cyclic peptide-like and bearing four oxazoles and a thiazole. Mechercharmycin B, a linear congener of mechercharmycin A, was also isolated from the same bacterium. Mechercharmycin A exhibited relatively strong antitumor activity, whereas mechercharmycin B exhibited almost no such activity.

Urukthapelstatin A, a novel cyclic peptide, was isolated from the cultured mycelia of marine-derived Thermoactinomycetaceae bacterium Mechercharimyces asporophorigenens YM11-542. The peptide was purified by solvent extraction, silica gel chromatography, ODS flash chromatography, and finally by preparative HPLC. Urukthapelstatin A dose-dependently inhibited the growth of human lung cancer A549 cells with an IC 50 value of 12 nM. Urukthapelstatin A also showed potent cytotoxic activity against a human cancer cell line panel.

The new cyclic peptide antibiotic, urukthapelstatin A, has been isolated from a culture of Thermoactinomycetaceae bacterium Mechercharimyces asporophorigenens YM11-542. The structure of urukthapelstatin A was elucidated by NMR, MS, Marfey analysis, chiral HPLC and X-ray crystal analyses. Keywords urukthapelstatin A, cyclic peptide, cytotoxic, Thermoactinomyces IntroductionUrukthapelstatin A (1) is a thiopeptide antibiotic which contains three oxazoles and two thiazoles in its cyclic structure and is structurally related to mechercharstatin (former name, mechercharmycin) [1,2] and YM-216391 [3, 4]. The fermentation, isolation and biological properties of 1 (Fig. 1) have been reported in the preceding paper [5]. This report describes the physico-chemical properties and structural determination of 1, which was produced by Mechercharimyces asporophorigenens YM11-542. Results Physico-chemical PropertiesThe physico-chemical properties of 1 are summarized in The relationship of the spin networks was established from 1 H-13 C long-range correlations in the HMBC spectrum and yielded three partial structures, which were assigned to a bithiazole-benzyloxazole moiety (C 15 H 7 N 3 OS 2 , partial structure A), one oxazole (C 3 HNO, partial structure B), and an alanine and isoleucinecontaining part (C 16 H 22 N 4 O 4 , partial structure C, Fig. 2). The HMBC correlations when n J CH was set to 2 Hz, were observed from H-34 (d H 8.59) to C-2 (d C 135.50), and from H-6 (d H 8.88) to C-4 (d C 155.11). Consequently, C-1 of partial structure A was connected to C-2 of partial structure B, and C-4 of partial structure B was connected to C-6 of partial structure C. In addition, the ROESY correlation of H-10 (d H 1.82) and N4-H (d H 9.49) revealed that a vinylmethyl part in partial structure C had a Z configuration (Fig. 2).Although there is no signal between partial structure A and C in HMBC spectrum, the C-20/C-21 connection can be brought about by the comparison of the molecular formula C 34 H 30 N 8 O 6 S 2 with a tolal of each partial structures (A; C 15 H 7 N 3 OS 2 , B; C 3 HNO, C; C 16 H 22 N 4 O 4 ), enabling the planer structure of 1 to be obtained.The absolute configuration of the alanine and isoleucine residues was determined by a Marfey analysis [6] and chiral HPLC analysis of the acid hydrolysate of 1. The Marfey analysis clarified the existence of L-Ala in the acid hydrolysate of 1, but D-Ile and D-allo-Ile were indistinguishable from the reversed-phase HPLC analysis of their FDAA derivatives. The chiral HPLC analysis successfully defined the absolute configuration of isoleucine as D-allo-Ile. Finally, the absolute stereochemistry of 1 was determined as shown in Fig. 1.An X-ray crystallographic analysis was also performed to confirm the full structure of 1. An adequate crystal was obtained by crystallization from CH 2 Cl 2 /MeOH (1 : 1). The crystal data and measurement conditions are summarized in the experimental section, and the ORTEP drawing shown in Fig. 3. The absolute configuration of 1 was ascertained ...

The volatiles isolated by solvent extraction and solvent-assisted flavor evaporation (SAFE) from roasted barley tea, prepared from either hulled barley or naked barley, were subjected to a comparative aroma extract dilution analysis, which resulted in 27 odor-active compounds with flavor dilution factors (FD factors) of 64–1024. An additional 5 odorants were detected by static headspace analysis. Quantitation of these 32 compounds revealed 22 and 23 odorants in the naked barley tea and in the hulled barley tea, respectively, that exceeded their odor-threshold values. On the basis of these data, the aromas of both barley tea variants were successfully reconstituted with reference compounds. The calculation of odor-activity values (OAVs = concentration/odor-threshold value) and omission tests suggested 2-methoxyphenol (OAVs 69 and 160) and trans-isoeugenol (OAVs 1.4 and 31) as key compounds responsible for the stronger smoky note in the hulled barley tea. Further important odorants in the naked and hulled barley teas included 2-acetylpyrazine (OAVs 23 and 16), 2-acetyl-1-pyrroline (OAVs 19 and 16), and 3-methylbutanal (OAVs 12 and 15).

Chelates of Schiff Bases of Pyridoxal Phosphate 2011 additional 483 mg. of DL-lysine-l-C14 was obtained, making a total average yield of 77.5% for the two Schmidt reactions. The over-all yield of pure DL-lysine-l-C14 from KC14N was 66.5%.All of the portions of DL-lysine-l-C14 monohydrochloride were chemically and radioactively pure as shown by paper chromatography and radioautography; m.p. 263-264°dec. Berkeley 4, California