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This secondary metabolite was identified in the exudates of the mite fed either on wheat germ, dry yeast, onion powder or mouse food, but in none of the foodstuffs. Received April 19, 1990 1. Chemical Ecology of Astigmatid Mites (Formerly Pheromone Study on Astigmatid Mites), XXVI: Kuwahara, Y., et al.: Jap. J. Sanit. Zool. 41, 23 (1990) 2. Harborne, J. B.: Introduction to Ecological Biochemistry. London: Academic Press 1988 3. Leal, W. S., et al.: Agric. Biol. Chem, 53, 295, 875, 1193 (1989); Ayorinde, F. O., et al.: Tetrahedron Lett. 25, 3525 (1984) 4. Leal, W. S., et al.: Naturwissenschaften 76, 332 (1989); Kuwahara, Y., et al.: ibid. 76, 578 (1989) 5. Kuwahara, Y., et al.: Appl. Ent. Zool. 23, 76 (1988) 6. Baker, G. T., Krantz, G. W., in: Acarology VI, Vol. 2. Chichester: Horwood 1984 7. Howard, R. W., et al.: Appl. Ent. Zool. 23, 58 (1988) 8. Leal, W. S., et al.: Agric. Biol. Chem. 53, 3279 (1989); Kuwahara, Y., et al.: ibid. 51, 3441 (1987)

2932

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1
0 ' 4000 3000 I ' 2000 i . . . . 1709D ~ 1500 • • , • = 1000 , • 700 i em 1

Fig. 1. Infrared spectrum of robinal generated in the vapor phase and displayed with the ordinate scale expanded by a factor of 6.25. The signals of the aldehyde (D) and ketone (A) are indicated; the extended conjugation explains the unusually low absorption frequency of the latter

cyclohexene- 1-carboxaldehyde, which has not been previously reported. Both the occurrence of an aldehyde at C(1) and a ketone at C(3) and such a high degree of conjugation are novel in monoterpene chemistry. Although we have no direct evidence in this regard,

this compound could rationally be biosynthesized by cyclization of ot-acaridial. R. robini is the sole mite, from 15 astigmatid mites investigated (including Caloglyphus and Schwiebea spp. of the same subfamily), to secrete robinal.

Naturwissenschaften 77,388- 389 (1990) © Springer-Verlag 1990

Growth-Promoting Effect of a Brassinosteroid in Mycelial Cultures of the Fungus Psilocybe cubensis
J. Gartz Institut ft~r Biotechnologie der A d W der DDR, DDR-7050 Leipzig G. A d a m and H.-M. Vorbrodt Institut for Biochemie der Pflanzen der A d W der DDR, DDR-4010 Halle/S. Brassinosteroids represent a new class of steroidal plant-growth regulators regarded from several laboratories as a further group of phytohormones. Till now about 30 members have been detected in a wide variety of higher plants including Angiospermae and Gymnospermae as well as in a green alga [1, 2]. The strong growth-promoting activity of brassinosteroids involves complex physiological effects, including increase in cell elongation and cell division [3]. Promising results in the application of 388 such compounds to produce higher crop yields and anti-stress effects have also been reported [4, 5]. However, hitherto no studies on occurrence and activity of brassinosteroids on fungi have been published. Here, we report on a strong promoting effect of a brassinosteroid on mycelial growth and fruiting of the subtropical fungus Psilocybe cubensis (Earle) Singer. In our studies an earlier described strain of this fungus was used which is characterized by a high stability in

growth and fruiting with various substrates [6]. The cultivation of the mycelium was carried out on 6 % malt agar and a horse dung/rice grain mixture in water was used to produce fruiting. Additionally, the substrates contained 5 g KH2PO 4 per 1. As brassinosteroid, synthetic 22S,23S-homobrassinolide (Fig. 1) prepared from stigmasterol (see [2]) was applied. In both cultivation systems the influence of 10 -2 ppm brassinosteroid on growth of the fungus was investigated (ten runs each). In the experiments with agar we observed that growth of mycelia took place two to three times

OH

HO-.
0 Fig. 1• Structure of 22S,23S-homobrassinolide HO'"

Naturwissenschaften 77 (1990) © Springer-Verlag 1990

Yokohama 236. which in normal development forms epidermis. Uchiyama Department of Biology. b) with 22S. 389. J. 325. W.9 g/10 g substrate). NucleosilC8 and -CN (Machery a. normally present in mushroom cultivation. 3 . The inducing activity is partially re389 Naturwissenschaften 77 (1990) © Springer-Verlag 1990 . N. 29. K. Physiol. ed. Basic Microbiol. Maught.. Hamada. 33 (1981) 5. the observed strong growth-promoting effect of 22S. Takahashi. P. T. chromatography on Sephadex G 100 with 6M urea/1M formic acid as eluent.. D. Yokota. The steroid-treated cultures afforded also a remarkably higher dry mass than the control cultivations ( 3 . Adam. into other pathways [1].: Biochem. H. 4 . G. A factor isolated from chicken embryos induces the formation of meso. The formation of incomplete fruit bodies. 1990 1. Ser. J. Pfl. are in progress.: Phytochemistry 25. including commercially important species. V. Japan M. Nakano and H. The factor has therefore been called the vegetalizing factor [2].23Shomobrassinolide in mycelial cultures of Psilocybe cubensis suggests that brassinosteroids could also play a phys- Fig. Davids. 2). A factor. The factor has a relative molecular weight of ~ 25 kD as the factor from chicken embryos (determined by SDS-PAGE) and dissociates into biologically inactive subunits ( M r ~ 13kD) by reduction with mercaptoethanol or by size-exclusion H P L C with 50 % formic acid as the eluent. These factors can channel the differentiation of early gastrula ectoderm. B. with brassinosteroid four to seven mushrooms were produced in the first flush compared to one to three in the control (Fig.5 weeks. a) Five weeks after inoculation. In summary. isolated by Smith [3] from the Xenopus XTC-cell line and an inducing factor found in a smaller quantity in human blood platelets [4].: FFTC Book Ser. in: Plant Growth Substances. 337 (1989). H. Furthermore. 188 (1986) 6. 1787 (1986) 3. the addition of the brassinosteroid caused a fruiting of the mycelia already in 3 to 3. Dau and H.391 (1990) @ Springer-Verlag t990 The Vegetalizing Factor Belongs to a Family of Mesoderm-Inducing Proteins Related to Erythroid Differentiation Factor M. Asashima. Marquardt.). Further studies. e.3 . Received May 2. Tiedemann Institut f~ir Molekularbiologie und Biochemie der Freien Universitgt. and successive steps of reversed-phase H P L C on Lichrosorb-RP 8 (Merck). These organs develop in the embryo from the vegetal region.. was almost completely suppressed by the brassinosteroid. Gartz. Hoppe. 53 (1987) 4.and endodermal organs.2.23S-homobrassinolide 3 weeks after inoculation iological role in higher fungi.: ACS Syrup. : Science 212. S. Loppnow-Blinde. 2. Yokohama City University. Heidelberg: Springer 1986 2. 347 (1989) Naturwissenschaften 77. a variation of the number of formed fruit bodies in the five flushes during fructification was observed. Fruit bodies of Psilocybe cubensis on dung/grain substrate. Interestingly.. followed by extraction with phenol. Bopp. Thus. T. have similar chemical properties [5]. 184. 9 g versus 2 . H. 34. p. whereas in the control the first sporocarps were produced within 4 to 5 weeks. We have isolated from calf kidney a mesoderm-inducing factor by using the same procedure as for the factor from chicken embryos: extraction with acid/ ethanol. Meudt. In the dung/grain substrate the first flush of fruit bodies appeared remarkably earlier. isoelectric focusing.faster than in the control series without steroid. 129 (M.1000 Berlin Protein factors are involved in the organ determination of embryos. Nagel). J. and Polypore-phenyl (Applied Biosystems) columns. Plessow. the added brassinosteroid also influenced the morphology of the formed fruit bodies which lacked the typical membranous annulus on the stems.g.