A Journal of Zeitschrift für Naturforschung C

Founded 1946 in the Institutes of the Max-Planck-Gesellschaft

Volume 45 Number 6 June 1990

Z E I T S C H R I F T F Ü R N A T U R F O R S C H U N G

Section C

A Journa l of Biosciences

I S S N 0341-0382

M a n a g i n g E d i t o r :

H . Hausen , T ü b i n g e n

C o u n c i l :

E . B ü n n i n g , T ü b i n g e n A . Butenandt , M ü n c h e n M . E i g e n , G ö t t i n g e n H . H a k e n , Stuttgart

Ed i to r s :

A . Hager , T ü b i n g e n K . H a h l b r o c k , K ö l n W . Hasselbach, He ide lbe rg P . K a r l s o n , M a r b u r g F . Kaudewi t z , M ü n c h e n J . K l e i n , T ü b i n g e n J . St. Schel l , K ö l n

Associa te Ed i to r s :

N . Amrhe in , Zür ich B . A . A s k o n a s , L o n d o n W . B a r z , M ü n s t e r P . B ö g e r , Kons tanz G . B o r n k a m m , F re ibu rg D . B ü c k mann, U l m H . Budz ik i ewicz , K ö l n K . G . G ö t z , T ü b i n g e n G . Got t schalk , G ö t t i n g e n P . Gruss , He ide lbe rg G . Isenberg, K ö l n R . Jaenicke, Regensburg V . ter M e u l e n , W ü r z b u r g G . F . M e y e r , T ü b i n g e n M . Ra jewsky , Essen D . Schui te -Frohl inde ,

M ü h l h e i m / R . G . Schulz , F re ibu rg F . F . Seelig, T ü b i n g e n J . Seel ig, Base l H . S i m o n , M ü n c h e n W . Steglich, B o n n H . Stieve, A a c h e n J . S u k o , W i e n A . Trebst , B o c h u m G . W e i s s e n b ö c k , K ö l n G . W i e k , Innsbruck F . Wie l and , H e i d e l b e r g V . Z i m m e r m a n n , W ü r z b u r g

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Contents

31 07.90 Z. Naturforsch. Vol. 45 c, No. 6, June 1990

Invited Trends Article

Elicitor Recognition and Signal Transduction in Plant Defense Gene Activation D . S C H E E L and J . E . P A R K E R 569

Original Communications

Porin of Rhodobacter capsulatus: Biochemical and Functional Characterization D . W O I T Z I K , J . W E C K E S S E R , R. B E N Z , S. S T E V A -

N O V I C , G . J U N G , and J . P. R O S E N B U S C H 576

The Biflavonoid Pattern of Rhytidiadelphus squar-rosus (Hedw.) Warnst. T. S E E G E R , H . D . Z I N S M E I S T E R , and H . G E I G E R

583

Phenolic Composition of Bud Exudates ofPopulus deltoides W . G R E E N A W A Y , S. E N G L I S H , and F . R. W H A T -

L E Y 587

Hybrid Origin of Populus x j a c k i i Conflrmed by Gas Chromatography-Mass Spectrometry Analysis of Its Bud Exudate W . G R E E N A W A Y , C. G . D A V I D S O N , T. S C A Y S -

B R O O K , J . M A Y , and F . R. W H A T L E Y 594

Epicuticular Waxes from Leaves of Maple {Acer pseudoplatanus L.) R. B. N . P R A S A D and P . -G. G Ü L Z 599

Comparative Investigation on Formation and A c -cumulation of Rare Phenylpropanoids in Plants and in vitro Cultures of P i m p i n e l l a major B. M E R K E L and J . R E I C H L I N G 602

Adenylate Kinase from Maize Leaves: True Sub­strates, Inhibition by P ,,P 5-di(adenosine-5')pentaphosphate and Kinetic Mechanism L . A . K L E C Z K O W S K I , D . D . R A N D A L L , and

W. L . Z A H L E R 607

Ascorbic Ac id and Chlorophyll Content in Cell Cultures of Spruce ( P i c e a abies): Changes by Cell Culture Conditions and A i r Pollutants B. M E S S N E R and J . B E R N D T 614

Characterization of Conformers of D 1 of Photo­system II Using Site-Directed Antibodies R. T. B E S F O R D , B. T H O M A S , N . S. H U S K I S S O N ,

and G . W. B U T C H E R 621

Surface Charge Density Changes in Isolated Pho­tosystem II Membranes Induced by Depletion of the Extrinsic Polypeptides of the Oxygen Evolving System A . G . I v A N O v , M . C. B U S H E V A , and M . Y .

V E L I T C H K O V A 627

Ribulose-1,5-bisphosphate Carboxylase-Binding Chloroplast Thylakoid Membrane Proteins. In vitro Evidence that H + - A T P Synthase may Serve as a Membrane Receptor K . - H . Süss 633

UVA-Induced Genetic Effects of Thioridazine, Mesoridazine and Sulforidazine: an in vitro Study S. A . S C H O O N D E R W O E R D , G . M . J . B E U E R S B E R -

G E N V A N H E N E G O U W E N , and I. R. P A N D A Y 638

X-Ray Induced Inactivation of the Sulfhydryl En­zyme Malate Synthase in the Presence of Var-ious Additives. Probing the Extent of Primary and Post-Irradiation Inactivation and Repair by Rapid Screening on the Microlevel H . D U R C H S C H L A G and P. Z I P P E R 645

Ribonucleosides in Mi lk : Characterization and Determination of the Concentration Profile of these Minor Components throughout a Lacta-tion Period (In German) K . - P . R A E Z K E and E. S C H L I M M E 655

Stimulation of Calmodulin Binding to Skeletal Muscle Membrane Proteins by 1,25-Dihydroxy-Vitamin D 3

V . M A S S H E I M E R , L . M . F E R N A N D E Z , and A . R.

D E B O L A N D 663

On the Problem of Season and Cold Dependence of Calcium Transport by Skeletal Muscle Sarco-plasmic Reticulum B. A G O S T I N I , L . D E M A R T I N O , and W. H A S S E L ­

B A C H 671

Efficacy of Different Hexacyanoferrates(II) in Inhibiting the Intestinal Absorption of Radio-caesium in Rats B. D R E S O W , P. N I E L S E N , and H . C. H E I N R I C H 676

Continued overleaf

ISSN 0341-0382

Contents Z. Naturforsch. Vol. 45 c, No. 6, June 1990

Bioavailability of Iron and Cyanide from 5 9 Fe-and 1 4 C-Labelled Hexacyanoferrates(II) in Rats P. N I E L S E N , B. D R E S O W , R. F I S C H E R , and H . C.

H E I N R I C H 681

Morphology and Chemical Contents of Dufour Glands of Pseudomyrmex Ants (Hymenoptera: Formicidae) A . B. A T T Y G A L L E , J . P. J . B I L L E N , B. D . J A C K ­

S O N , and E . D . M O R G A N 691

Determination of Relative Volatility of Lepido-ptera Sex Pheromones by Closed Loop Strip­ping (In German) H . J . B E S T M A N N , J . E R L E R , and O. V O S T R O W S K Y

698

14-Deoxyecdysteroids in an Insect ( G r y l l u s hi-maculatus ) K . H . H O F F M A N N , E . T H I R Y , and R. L A F O N T 7 0 3

Ontogenetic Patterns in Amounts and Proportions of Dufour's Gland Volatile Secretions in Virgin and Nesting Queens of Lasioglossum m a l a c h u -r u m (Hymenoptera: Halictidae) M . A Y A S S E , W . E N G E L S , A . H E F E T Z , G . L Ü B K E ,

and W . F R A N C K E 7 0 9

Cytoplasmic Vibrations Due to Flagellar Beating in T r i c h o p l a x adhaerens F . E . Schulze (Placo-zoa) H . W E N D E R O T H 7 1 5

Dominance of Celestial Cues over Landmarks Disproves Map-Like Orientation in Honey Bees R. M E N Z E L , L . C H I T T K A , S. E I C H M Ü L L E R , K .

G E I G E R , D . P E I T S C H , and P. K N O L L 7 2 3

Notes

Production of ß-Carboline Alkaloids in Trans-formed Root Cultures of Peganum h a r m a l a L . I. N . K U Z O V K I N A , A . G O H A R , and I. E . A L T E R -

M A N 7 2 7

Short-Wavelength Absorbing Complexes of Chlorophyll a in Micellar Solution of Cationic Detergents A . S C H M I D T , J . G O T T S T E I N , H . S C H E E R , and A .

S C H E R Z 7 2 9

Notes 729

Short-Wavelength Absorbing Complexes of Chlorophyll a in Micellar Solution of Cationic Detergents A . Schmidt, J. Gottstein, and H . Scheer Botanisches Institut der U n i v e r s i t ä t , M e n z i n g e r S t r a ß e 67, D - 8 0 0 0 M ü n c h e n 19, Bundes repub l ik D e u t s c h l a n d

and

A . Scherz Biochemis t ry Depar tmen t , T h e W e i z m a n n Institute o f Science, IS-76 100 R e h o v o t , Israel

Z . Na tu r fo r sch . 45c, 7 2 9 - 7 3 2 (1990); received J anua ry 26, 1990

C h l o r o p h y l l , M i c e l i e s , Detergent , A g g r e g a t i o n , A b s o r p ­t i on , C i r c u l a r D i c h r o i s m , M o l e c u l a r O r b i t a l

M i c e l l a r aggregates have been prepared f rom Chloro­p h y l l a . Whereas mos t detergents i n c l u d i n g non - ion i c , zwi t te r ion ic a n d an ion i c ones, p roduce aggregates w i t h long-wavelength shifted and enhanced Q Y ab so rp t ion , the ca t ionic detergents h e x a d e c y l - t r i m e t h y l a m m o n i u m -bromide and hexadecy l -py r id in iumch lo r ide p roduce complexes w i th opposi te traits: T h e Q Y abso rp t ion is shifted to shorter wavelengths, a n d it is h y p o c h r o m i c . T h e opt ica l ac t iv i ty is increased as in the long-wave­length shifted complexes , but the cd bands are non-con-servative and co inc ide w i t h the absorp t ion m a x i m a . T h e complexes are most l ike ly sma l l aggregates o f Chloro­p h y l l wi th a changed geometry as compared to the "Standard" ones.

Introduction Micellar complexes of Chlorophylls and bac-

teriochlorophylls have gained attention due to the spectroscopic similarities with (bacterio)chloro-phyll proteins containing the same pigments [1-8]. It has been argued that these similar properties re-sult from the formation of aggregates with similar geometry, reflecting an inherent property of the large aromatic Systems, e.g. Chlorophyll. This view has been strengthened recently: Very similar types of aggregates have been found i) in the primary donor P960 or P870 of bacterial reaction centers as determined by X-ray crystallography [9-11], ii) in vacuo as calculated by molecular orbital methods [12], and iii) in aggregates formed in

A b b r e v i a t i o n s : C h i , Chlorophyll; B e h l , bac te r ioch lo ro -p h y l l ; C T A B , h e x a d e c y l - t r i m e t h y l a m m o n i u m b r o m i d e ; C P C , hexadecy l -pyr id in iumch lo r ide .

Rep r in t requests to Prof . D r . H . Scheer.

Verlag der Zeitschrift für Naturforschung, D-7400 T ü b i n g e n 0341 -0382/90/0600-0729 $ 01.30/0

mixed organic-aqueous solvent Systems as deter­mined by the analysis of optical spectra [2,4].

Exciton theory principally predicts both red-and blue-shifted spectra depending on the relative orientation of the monomers in Chlorophyll aggre­gates, and concomitant hyper- und hypochromism [see 2, 4]. A l l Chlorophyll proteins and in vitro Chlo­rophyll aggregates investigated to date exhibit nonetheless a red-shifted Q Y band. Here, we wish to report the formation of blue-shifted non-cova-lently linked aggregates of Chlorophyll a with hy­pochromic Q Y band, which are formed in micellar Solutions of cationic detergents.

Materials and Methods C h i a was extracted from spray-dried S p i r u l i n a

geitleri and purified by dioxan preeipitation [13] and subsequent chromatography on DEAE-ce l l u -lose [14]. The pigment was deposited on the walls of plastic vials by evaporating an etheral Solution in a stream of nitrogen, and then redissolved in de­tergent Solution (0.1% in tris buffer, 10 mM, p H 7.5, if not stated otherwise) with sonification (Bransonic model 220) until the spectra remained constant. The final Solutions had an optical densi­ty between 0.5 and 1 cm" [ in the red spectral band, corresponding to Chi a concentrations of 10-20 UM . The position of the near-infrared band of the complexes was not affected by the concen-tration in this ränge.

The following detergents were used: C T A B (hexadecyl-trimethylammoniumbromide), C P C (hexadecyl-pyridiniumchloride), L i D S (Lithium dodecylsulfate), and Triton X-100 (Octylphenoxy-polyoxyethylen-glycol) from Serva, Heidelberg; R D L 203/S (dodecanoic acid-ethanolamid), Brij 30 (Polyoxyethyleneglycol-monododecyl-ether), R - A M / V (N-3-hydroxyethyl-N-carboxy-methylfatty acid amidoethylamin, Na-salt), R - A M / 2 L (N-3-hydroxyethyl-N-carboxymethyl fatty acid ethylamin, Na-salt), R-IPL-203 (dode­canoic acid-isopropanolamid), R-B204 (Alkyl -amidopropyldimethylaminoxid), all from Rewo, Steinau; Tr i ton-H 66 (Alkylphosphatester, Na-salt), Triton-QS44 (Alkylphosphatester), from Bayrol , München. A l l detergents were used with-out further purification.

Absorption spectra were recorded in a model 320 spectrophotometer (Perkin-Elmer), cd spectra

730 N o t e s

in a dichrograph model V (Jobin-Yvon), and flu­orescence spectra in a fluorolog System (Spex). The fluorescence spectra are uncorrected.

Results The absorption maxima for the complexes

formed with the different detergents are listed in Table I. With most of the detergents, Chlorophylls form two types of complexes. One has absorptions similar to Chlorophyll in monomeric Solution, e.g. in methanol, the other one ansorbs around 740 nm in the red spectral region. A typical example is shown in Fig . 1. The oscillator strength of the Q Y

band of the latter is enhanced about two-fold. The optical activity is increased by Orders of magni-tude, but the s-shaped cd-band is nearly conserva-tive (not shown). The ratio of the two forms de-pends on the detergent concentration, with the 740 nm absorbing form favored at lower concen­tration, but is also dependent on the structure of the detergent used. Red-shifted complexes are also formed with pheophytin a (A.m a x around 700 nm, not shown). These spectral traits and concentra­tion dependencies are very similar to the Situation found with bacteriochlorophylls [1 —8].

A different Situation is observed with the two cationic detergents, C T A B and C P C . Again two

Tab le I. A b s o r p t i o n m a x i m a o f mice l l a r complexes o f Chlorophyll a w i t h several detergents o f different struc-tural types. See M a t e r i a l s and M e t h o d s for structures. A l l detergents were 0 . 1 % except for the cationic ones ( C T A B and C P C ) w h i c h were 0 .05%. C o m p l e x e s marked w i t h " + + " are essentially d e v o i d o f m o n o m e r s absorb ing a r o u n d 665 n m , the ones m a r k e d w i t h " + " give mixtures (see e.g. F i g . 1).

Detergent T y p e C o m p l e x A b s o r p t i o n fo rma t ion m a x i m u m [nm]

T r i t o n X - 1 0 0 non - ion i c + + 742 R D L 2 0 3 / S non - ion i c + + 742 R - I P L - 2 0 3 non - ion i c 742 Br i j30 non- ion ic + 744 R - B 2 0 4 non - ion i c + 742 T r i t o n H 6 6 an ion i c + 742 T r i t o n Q S 4 4 an ion i c + + 742 C P C ka t i on i c + 646 C T A B ka t i on i c + 646 R - A M / V zwi t t e r ion ic* + 742 R - A M / 2 L zwi t t e r ion ic* + + 740

* A m p h o t e r i c between p H 4 and p H 7.

X[nm] F i g . 1. A b s o r p t i o n spectrum o f a mice l l a r Solu t ion o f Chlorophyll a w i t h T r i t o n X - 1 0 0 (0 .1%) i n Tr i s buffer (10 M , p H 7.5).

complexes are formed, one of which absorbs like Chlorophyll in monomeric Solution. The second complex formed absorbs at 646 nm (Fig. 2),

_ , 1 1 — 1 1

400 600 800 X [nm]

F i g . 2. C i r c u l a r d i c h r o i s m (bot tom) a n d absorp t ion spectra (top) o f mice l l a r Solut ions o f C h l o r o p h y l l a w i t h h e x a d e c y l - t r i m e t h y l a m m o n i u m b r o m i d e in T r i s buffer (10 m M , p H 7.5). Detergent concen t ra t ion 0 .008% ( ) a n d 0 .05% ( ).

Notes

6Q0 700 800

X [nm] F i g . 3. Fluorescence spectra of a micellar Solution of Chlorophyll a with hexadecyl-trimethylammonium-bromide (0 .05% in T r i s buffer, 10 mM, p H 7.5) excited at 400 ( ) and 450 nm ( ). T h e absorption spectrum of this Solution is shown in F i g . 2, top, dashed line.

however, which corresponds to a blue-shift of 20-22 nm as compared to e.g. methanolic Solu­tion. The Soret band is blue-shifted as well to 420 nm. The oscillator strength of the Q Y band is decreased, and it is strongly optically active show-ing essentially a purely negative band peaking at the wavelength of maximum absorption (Fig. 2). The complex shows moderate fluorescence, and the emission band is blue-shifted as well (Fig. 3). As in the other detergents, the ratio of the two complexes depends on the detergent concentra­tion, with the short-wavelength form dominant at low concentrations. A t 0.008% C T A B , the blue-shifted form is essentially pure (Fig. 2), but already at .05% there is an equal absorption of the two species at 642 and 668 nm. The short-wavelength absorbing complex is also unstable towards deter­gents forming red-shifted complexes by them-selves. As an example, the addition of L i D S (0.5%) shifts the absorption to 658 nm, and higher concentrations give a mixture of two forms ab­sorbing at 672 and 746 nm, which is similar to the Situation with L i D S alone.

Discussion The red-shifted complexes formed with Behl

and Chi alike have been related to aggregation of

731

the pigments (see [5, 8]). In detergent Solution, aggregation numbers of the pigments are small. Using exciton theory, Scherz and Parson [2,4] sug-gested a dimeric strueture of the basic unit in which the two macroeycles are nearly parallel («15° angle between the planes of the macro­eycles) at a distance of ~3.5 Ä, and in which only part of the macrocyclic System overlaps due to a lateral displacement of both macroeycles from the center of the dimer. The Q Y axes form an angle of «145° .

It is surprising that this strueture, which is formed in micelles of a variety of detergents, and also in mixed aqueous-organic solvent Systems, closely resembles the strueture of the Bchl-special pair in reaction centers of Rhodopseudomonas v i r i ­dis and Rhodobacter sphaeroides, e.g. the primary donor involved in light-induced Charge Separation [9-11]. Moreover, a similar arrangement has been calculated by Plato et al. [12] as the minimum ener-gy arrangement in the absence of interactions with the solvent. These similar arrangement of the two Chlorophylls in very different environments - vac-uum, detergent micelle, pigment micelle, or protein - points to an inherent tendency of the bacterio-chlorophyll molecule in forming aggregates of this special geometry.

The present study was undertaken in part to test if the same type of complex can be formed as well with Chlorophyll a . This was indeed observed and further strengthens the hypothesis. Nearly inde-pendent of the detergent used, there is always the formation the same type of red-shifted complex as shown in Fig. 1 for Triton X-100, ifjudged from the similarities of their absorption and cd spectra. This is true but for two exceptions, viz. the cationic de­tergents C P C and C T A B , which form blue-shifted complexes. It is principally inherent to exciton theory, that both blue and red shifts (as well as none at all) can occur in dimers (or higher aggre­gates) of Chlorophylls, depending on the relative orientation and distance of the two pigment mole-cules (see e.g. [2]). The present example is to our knowledge nonetheless the first case among the many different aggregates of Chlorophylls formed by association or a Single covalent linkage, in which a blue-shifted species has actually been ob­served. A blue-shifted bis-chlorophyll-cyclophane has been reported, however, by Overfield et al. [16] in which the two pigments show little interaction.

732 N o t e s

Behl a complexes have been studied before with the same two cationic detergents [6]. Generally, the latter are strongly dissociating both to long-wave-length absorbing complexes of Behl a with other detergents, and to Behl a proteins. In our hands, of the two detergents, only C T A B does form a small Proportion of Behl a aggregates (besides mono­mers) at all at low detergent concentrations. How­ever, these complexes are red-shifted similar to the ones observed in any of the other non-ionic, anion­ic and zwitterionic detergents studied. This points to a somewhat different aggregation pattern in the

Behl as compared to the Chi chromophore, which may be related to the different oxidation states of the macroeycles, or the different Substitution pat­tern. Differences of this kind should be important in the interactions of Polypeptide and pigments in (bacterio)chlorophyll proteins as well.

A ckn o wledgemen ts

This work was supported by the Deutsche For­schungsgemeinschaft (SFB 143, project A I and A Z 140/9-1).

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