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Dioscorea Sp.) Genotypes Oliver Vendla, Christoph Wawroscha, Christian Noeb, Carlos Molinac, Günter Kahlc,D, and Brigitte Koppa,*

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Dioscorea Sp.) Genotypes Oliver Vendla, Christoph Wawroscha, Christian Noeb, Carlos Molinac, Günter Kahlc,D, and Brigitte Koppa,* Diosgenin Contents and DNA Fingerprint Screening of Various Yam (Dioscorea sp.) Genotypes Oliver Vendla, Christoph Wawroscha, Christian Noeb, Carlos Molinac, Günter Kahlc,d, and Brigitte Koppa,* a Department of Pharmacognosy, University of Vienna, Althanstr. 14, A-1090 Vienna, Austria. Fax: +43-1-4 27 75 52 55. E-mail: [email protected] b Department of Medicinal-Pharmaceutical Chemistry, University of Vienna, Althanstr. 14, A-1090 Vienna, Austria c Plant Molecular Biology, Biocenter, University of Frankfurt, Marie-Curie-Str. 9, D-60439 Frankfurt am Main, Germany d GenXPro, Frankfurt Innovation Centre Biotechnology, Altenhöfer Allee 3, D-60438 Frankfurt am Main, Germany * Author for correspondence and reprint requests Z. Naturforsch. 61c, 847Ð855 (2006); received July 28/August 23, 2006 Dedicated to Prof. Wilhelm Fleischhacker on the occasion of his 75th anniversary In addition to the importance of many Dioscorea species (yams) as starchy staple food, some representatives are known and still used as a source for the steroidal sapogenin diosge- nin, which, besides phytosterols derived from tall-oil, is an important precursor for partial synthesis of steroids for pharmaceutical research and applications. While in edible yams the diosgenin content should be as low as possible, a high yield of the compound is preferable for cultivars which are grown for the extraction of sterols. In the past, miscalculations and insufficiently precise techniques for quantification of diosgenin prevailed. Therefore we set out to re-evaluate the steroid content of a world collection of Dioscorea species, using leaves as sample material. We optimized diosgenin quantification techniques and fingerprinted the whole collection with the DNA amplification fingerprinting (DAF) technique. Total diosgenin contents ranged from 0.04 to 0.93% of dry weight within the collection. Several Dioscorea cultivars can be characterized via their DAF fingerprint pat- terns. Key words: Dioscorea, Diosgenin Production, DNA Amplification Fingerprinting Introduction posit them in their storage tubers. However, field cultures of Dioscorea have various limitations as Yams (Dioscorea sp.) are widely distributed. e.g. poor seed germination (Forsyth and Van Sta- They are economically important tuber and bulbil den, 1982) and continuous exposure to viral, bac- crops in tropical and subtropical regions world- terial and fungal pathogens and nematodes (Ng, wide. They have been used as aliment since ages, 1988) with inevitable yield losses. Moreover, the and 13 out of some 40 cultivars can be regarded extensive harvesting of wild plants for pharmaceu- as regional or worldwide important food plants tical use endangered several Dioscorea species in (Rehm and Espig, 1984). Apart from the tradi- regions such as Mexico and South Africa (Cour- tional importance as starchy staple food, some Di- sey, 1967). Therefore, and rather early in yam re- oscorea species are known and used as a source search, in vitro cell cultures have been established for the steroidal sapogenin diosgenin, a precursor as an alternative to field plantations. The produc- for the synthesis of steroid drugs (Djerassi, 1992; tion of diosgenin in such cell cultures, however, Chu and De Ca´ssia Leone Figueiredo Ribeiro, was variable (Aminuddin and Chowdhury, 1983; 2002). In fact, pharmaceutical phytosterols have C´ ulafic´ et al., 1999; Kaul and Staba, 1968). Yet the primarily been derived from tall-oil, a byproduct failure of achieving fully chemical synthesis of of wood processing in the cellulose industry (Dias steroids until now again made Dioscorea a very et al., 2002), but second in importance were (and attractive source for steroidal precursors. still are) field cultures of Dioscorea plants, that While edible Dioscorea species should lack ex- produce diosgenin derivatives in leaves and de- ceeding amounts of steroids, a preferably high 0939Ð5075/2006/1100Ð0847 $ 06.00 ” 2006 Verlag der Zeitschrift für Naturforschung, Tübingen · http://www.znaturforsch.com · D 848 O. Vendl et al. · Diosgenin Contents and DNA Fingerprinting of Yams content is of importance for those species which Materials and Methods serve as raw material for the isolation of diosgenin derivatives. From the early 1940 on, diosgenin con- Plant material tents of various Dioscorea species and several dif- The various Dioscorea species and cultivars em- ferent organs were repeatedly estimated, but the ployed are listed in Table I. They were either pro- values published by several authors are to be com- vided as bulbils, tubers or in vitro plantlets. Usu- pared with caution and should only partially be ally bulbils and tubers were germinated in moist considered as contribution to an overall diosgenin soil, in vitro plantlets were transferred to soil and screening of the whole genus, since analytical left in a mist chamber for 4 weeks. The emerging, methods as well as the tissue samples varied con- acclimatized plants were grown in the greenhouse siderably (Akahori, 1965; Anzaldo, 1956; Barua under normal day-night regimes prevailing in Cen- et al., 1954, 1956; Czikow and Łaptiew, 1983; tral Europe. Marker et al., 1943; Quigley, 1978; Wall et al., 1952a, b, 1954a, b, 1955, 1957). Also, in many cases the techniques were far from advanced. In his Diosgenin quantification book “Yams”, Coursey (1967) reported of diosge- Sample preparation, extraction and hydrolysis nin contents of several Dioscorea species, which were performed as described by Farnleitner had been estimated by the above-mentioned au- (2004), consisting of the following procedures: Ly- thors, on a percent basis. However, among others ophilized plant material was ground in a Retsch he quoted figures from publications by Marker ZM-100 centrifuge mill (0.5 mm mesh sieve). For et al. (1943), which were originally reported as Ð1 each sample, 1.00 g of ground material was sus- gkg , as percent, as well. Thus, those diosgenin pended in 20 mL water for 24 h at room tempera- values in the book “Yams” adopted from Marker ture for enzymatic pre-hydrolysis. For extraction and colleagues are tenfold too high. As this book of dioscin and already pre-hydrolyzed diosgenin, has been considered a standard for Dioscorea-re- 30 mL iso-PrOH were added, which resulted in a lated research since then, the incorrect values have 60% (v/v) aqueous iso-PrOH solution. After esti- been uncritically adopted by further authors. This mation of the exact weight, the mixture was combination of rather imprecise techniques, wrong heated to 100 ∞C in a water bath for 3 h and then quotations and inherent variability of diosgenin centrifuged at 3500 rpm for 7 min. The superna- contents led to much confusion and practically a tant was weighed again before additional iso- cessation of yam research. PrOH and H2SO4 were added in a proportion For all of these reasons we considered it essen- leading to a final concentration of 2 m H SO in tial to establish a collection of as many Dioscorea 2 4 70% (v/v) iso-PrOH/30% H2O. Hydrolysis pro- clones in vivo as we were able to procure as well ceeded for 4 h at 100 ∞C in a water bath. 3.0 mg as to develop a uniform procedure for sample progesterone (Sigma Aldrich; purity: 98.45%) as preparation and diosgenin analysis, which alto- an internal standard were added. The solution was gether aimed at retrieving reliable informations on diluted 50:50 (v/v) with distilled H2O and ex- the diosgenin content of various Dioscorea species tracted three times with 30 mL dichloromethane. and cultivars of several species. To our knowledge, The collected organic phases were first deacidified diosgenin screening has never been carried out with 30 mL and then 60 mL 5% (m/v) aqueous with a comparably large collection of Dioscorea NaHCO . The organic phase was dehydrated with accessions that are all grown under the same con- 3 Na2SO4. After filtration, the solvent was evapo- ditions in the same greenhouse. In order to moni- rated under reduced pressure and the residue was tor the reliability of classification of the accessions re-dissolved in 4 mL dichloromethane for GC we received from several regions worldwide, to analysis [apparatus: Perkin Elmer Auto System correct misclassifications and to examine the po- XL gas chromatograph; carrier gas: nitrogen; flow tential of genetic distinction between species and rate: 2 mL minÐ1; injection: splitless mode, 290 ∞C; cultivars within the same test setup, we set out a injection volume: 1 μL; column: HP-5 (crosslinked DNA fingerprint screening upon our entire collec- 5% Ph Me Silicone), 50 m ¥ 0.32 mm i. d. ¥ tion of Dioscorea clones, using the DAF (DNA 0.52 μm; temperature program: initial temperature amplification fingerprinting) procedure. 290 ∞C, 1 ∞C minÐ1, final temperature 310 ∞C, hold 10 min; detection: FID; quantification was accom- O. Vendl et al. · Diosgenin Contents and DNA Fingerprinting of Yams 849 Table I. An inventory of all Dioscorea species and cultivars used in the present study. Species Cultivar (subspecies) Origin (country) D. alata 7087a University of Frankfurt (Germany) D. alata E-1-04 Ventanas, Los Rios (Ecuador) D. alata E-1-06 Ventanas, Los Rios (Ecuador) D. alata TDa 289 Intl. Institute of Tropical Agriculture, IITA (Nigeria) D. alata TDa 1349 Intl. Institute of Tropical Agriculture, IITA (Nigeria) D. alata V-1-12 Maracay, Carabobo (Venezuela) D. alata V-1-30 Maracay, Carabobo (Venezuela) D. alata V-1-34 Maracay, Carabobo (Venezuela) D. alata V-1-51 Maracay, Carabobo (Venezuela) D. alata V-1-53 Maracay, Carabobo (Venezuela) D. alata V-1-55 Maracay, Carabobo (Venezuela) D. alata V-1-59 Maracay, Carabobo (Venezuela) D. alata V-1-60 Maracay, Carabobo (Venezuela) D. alata V-1-61 Maracay, Carabobo (Venezuela) D. alata V-1-63 Maracay, Carabobo (Venezuela) D. alata V-1-70 Maracay, Carabobo (Venezuela) D. alata V-1-87 Maracay, Carabobo (Venezuela) D. alata V-1-90 Maracay, Carabobo (Venezuela) D. alata V-1-95 Maracay, Carabobo (Venezuela) D.
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