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Volume 56—1976

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PLANTS OF OKLAHOMA AND TEXAS CAPABLE OF PRODUCING CYANOGENIC COMPOUNDS

David S. Seigler

Department of Botany, The University of Illinois, Urbana, Illinois

We have surveyed the distribution of cyanogenic compounds in plants from Oklahoma and Texas. Approximately 135 species of plants from 46 families are known to contain compounds capable of liberating hydrogen cyanide upon hydrolysis. These are primarily found in the Gramineae, Rosaceae, Leguminosae, Polypodiaceae, and Euphorbiaceae. The chemical structures of the cyanogens have been studied in only a small number of the species included and investigation of the biology and chemistry of these plants should prove profitable.

INTRODUCTION

A study of the distribution of cyanogenic plants of Oklahoma and Texas was begun for several reasons. Our principal interest in this study arose because we felt these compounds could be useful as taxonomic characters for the study of plant groups found in North America. The literature of cyanogenic plants from the northeastern United States has previously been surveyed (1). Several reports in the literature point to the utility of these compounds for this purpose (2-16). Although their chemotaxonomic value is considerable, perusal of the literature reveals that structures of specific compounds responsible for this activity are known in but a small percentage of the plants listed (see Table 1). Thus, at the present time we do not have adequate data to utilize these chemical characters for taxonomic study except in a few cases.

A second reason for making this investigation may be even more important to the average reader — these compounds and plants which contain them are poisonous to both humans and livestock. Kingsbury (17) has discussed the toxic nature of cyanogenic glycosides. Generally, plants which contain more than 20 mg HCN/100 grams of fresh plant material may be considered potentially dangerous, but several factors determine whether poisoning will actually take place (17).

Plants which are capable of producing cyanogenic compounds are distributed widely in the plant kingdom and are known from at least 1000 species in 90 families. The known chemical types have recently been reviewed (18). Although plants containing these compounds are widespread, the structures of only about 30 compounds have appeared in the literature and specific compounds have been isolated from fewer than 100 species. Most literature accounts are based on the color test using paper impregnated with sodium picrate solution, suspended in a vial over plant material to which a b-glucosidase has been added. A change from yellow to a brick-red color constitutes a positive test (19).

In this study I have considered only the states of Oklahoma and Texas, which because of their large and diverse flora will add a major section to the contemplated goal of preparing a listing of cyanogenic plants of the entire United States. For information concerning the distribution of certain plant species, I have consulted Correll and Johnston (20), Waterfall (21), Vines (22), Bailey (23), and Warnock (24). Of the records of cyanogenic nature included, many are doubtful and should be verified. Among these are: Nerium oleander, Impatiens balsamina, Borago officinalis, Heliotropium indicum, Campanula rotundifolia, Cleome hassleriana, Carica papaya, Beta vulgaris, Ipomoea spp., members of the Cruciferae, Ricinus communis, Zea mays, Cinnamomum camphorum, Pisum sativum, Medicago sativa, Cassia alata, Cicer arietinum, Glycine max, Arachis hypogaea, Dolichos lablab, Lagerstroemia speciosa, Melia azedarach, Psidium guajava, Oenothera biennis, Guara biennis, Oxalis corniculatus, Dryopteris filix-max, Reseda alba, Rhamnus frangula, Solanum melongena, and Lycium halmifolium.

Considerable changes in cyanogenic properties occur with diurnal, seasonal, and ecological variations. Many plants appear

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[Pages 96, 97 and 98 consists entirely of Table 1.]

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to respond to stress conditions by increased synthesis of these compounds; Sorghum halepense is known to be especially poisonous to livestock after a light frost or during drought (17). Often some plant parts are cyanogenic whereas others may be completely devoid of any cyanogens. Because of these variations, it is clear that positive records are more important than negative reports. Most workers, with the exception of Gibbs (16) and Seigler (1, 18), have examined materials from continents other than North America and the occurrence of cyanide-producing materials should be confirmed in material from this continent. A tabulation of plants which have been reported as cyanogenic or have been found so in our laboratory (as indicated by the sodium picrate method) is given below (Table 1). This is not a complete list and, no doubt, additions will be made. Several species, as suggested above, should probably be deleted if the presence of cyanide cannot be confirmed. In most cases, the reference cited represents the most complete chemical work on characterized compounds. It usually represents the first record in plants with uncharacterized cyanogens.

TABLE 1. Plants of Oklahoma and Texas known to be capable of producing cyanogenic compounds.

Family and species Compound Reference
Apocynaceae
     Nerium oleander L.a,b unknown 16
Araceae
     Colocasia esculenta Schott.a,b unknown 25
Araliaceae
     Aralia spinosa L. unknown 1
Balsaminaceae
     Impatiens balsamina L.a unknown 16
Berberidaceae
     Nandina domestica Thunb.a,b p (glucosyloxy) mandelonitrile 26,27
Boraginaceae
     Borago officinalis L.a unknown 3,4
     Heliotropium indicum L.b unknown 16
Calycanthaceae
     Calycanthus floridus L.a unknown 3, 4
Campanulaceae
     Campanula rotundifolia L. unknown 16
Capparidaceae
     Cleome hassleriana Chod.a,b unknown 16
Caricaceae
     Carica papaya L.a unknown 16
Chenopodiaceae
     Atriplex semibaccata R.Br.a,b unknown 6
     Beta vulgaris L.a,b unknown 16
     Chenopodium album L.b unknown 16
     Suckleya suckleyana (Torr.) Rydb. unknown 6
Convolvulaceae
     Ipomoea batatas (L,) Lam.a,b unknown 16
     Ipomoea cairica (L.) Sweeta,b unknown 16
     Ipomoea quamoclit L.a unknown 16
     Ipomoea sinuata Ort. unknown 26
Compositae
     Achillea millefolium L.b unknown 3, 4
     Centaurea americana Nutt. unknown 28
     Dimorphotheca ecklonis D.C.a linamarin and lotaustralin 29
     Dimorphotheca pluvialis Moench.a linamarin and lotaustralin 29
Cruciferae
     Armoracia lapathifolia Gilib.a,b unknown 30
     Brassica oleracea L. unknown 16
     Eruca sativa Mill.b unknown 30
     Nasturtium officinale R.Br.b unknown 16
     Thlaspi arvense L.b unknown 30
     Stanleya pinnata (Pursh.) Britt.? unknown 16
Cycadaccae
     Cycas revoluta Thunb.a The pseudocyanogenic
compounds, cycasin and
neocycasin A
31,32
Droseraceae
     Drosera intermedia Hayne. unknown 29
Euphorbiaceae
     Cnidoscolus texanus (Muell. Arg.) linamarin 16,33
           Small
     Codiaeum variegatum Blumea unknown 16
     Euphorbia hirta L. unknown 16
     Manihot walkerae Croizat. unknown 20, 34 this study
     Phyllanthus niruri L. unknown 16
     Ricinus communis L.a,b unknown 26
     Sapium sebiferum (L.). Roxb.a,b unknown this study
     Stillingia texana I.M. Johnst. unknown 28
          (or S. dentata)
Garryaceae
     Garrya wrightii Torr. unknown 16
Gramineae
     Agrostis stolonifera L.b unknown 35
     Bambusa arundinacea Willd.a unknown 36
     Bothriochloa intermedia (R.Br.)a,b unknown 37
           A. Camus
     Bothriochloa ischaemum (L.) Keng.a,b unknown 37
     Bouteloua gracilis (HBK.) Griffiths unknown 37
     Briza minor L.b unknown 37
     Cortaderia argentea Stapf.a unknown 37
     Dactylotaenium, aegypticu m (L.) Beauv.b unknown 37
     Eleusine indica (L.) Gaertn.b unknown 37
     Festuca elatior L. unknown 35
     Glyceria septentrionalis Hitch. unknown 28
     Holcus lanatus L. unknown 37
     Leptochloa dubia (HBK.) Nees unknown 37
     Lolium perenne L.b unknown 37
     Panicum maximum Jacq.b? unknown 37
     Poa pratensis L. unknown 51
     Sorghum almum Parodia,b unknown 17
     Sorghum bicolor (L.) Moench.a,b,c dhurrin 37, 38
     Sorghum halepense (L.) Pers.a dhurrin 17,38,39
     Tridens flavus (L.) Hitch. unknown 37
     Zea mays L.a unknown 40

 

     Avena, Hordeum, Triticum, Oryza, Saccharum and Secale have also been reported as cyanogenic (43). The cyanogenic principles are all unknown.

 

Grossularicaeae
     Ribes odoratum Wendl. unknown 41
Haloragaceae
     Myriophyllum brasiliense Camb.b unknown 3, 4
Hydrocharitaceae
     Vallisneria americana Michx. unknown 16
Hydrophyllaceae
     Phacelia congesta Hood unknown 16, this study
Iteaceae
     Itea virginica L. unknown 42
Lauraceae
     Cinnamomum camphora Nees & Eberm.a,b unknown 16
Leguminosae
     Acacia berlandieri Benth. unknown this study
     Acacia constricta Gray acacipetalin 44
     Acacia farnesiana (L.) Willd. linamarin and lotaustralin (?) 45
     Acacia greggii Gray unknown 17
     Acacia roemeriana Scheele unknown this study
     Arachis hypogaea L. unknown 16
     Cassia alata L. unknown 16
     Cicer arietinum L. unknown 6
     Dolichos lablab L.a unknown 6,26
     Glycine max Merr. unknown 16
     Lotus corniculatus L.a,b linamarin and lotaustralin 46
     Lupinus texensis Hook. unknown this study
     Medicago sativa L.a,b unknown 6
     Phaseolus lunatus L.a linamarin and lotaustratin 25
     Phaseolus vulgaris L. linamarin and lotaustralin ? 50
     Pisum sativu L.a unknown 16
     Prosopis glandulosa Torr.
           (juliflora)
unknown 3,4,6
     Trifolium repens L.a,b linamarin and lotaustralin 47,48
     Trifolium pratense L. unknown 35
     Vicia angustifolia L.b vicianin 49
     Vicia sativa L.b unknown 26
Linaceae
     Linum lewisii Pursh. unknown 28
     Linum usitatissimum linamarin and lotaustralin 46,52
Lythraccae
     Lagerstroemia speciosa Pers.a unknown 16
Magnoliaccae
     Liriodendron tulipifera L. unknown 3,29
Meliaceae
     Melia azedarach L.b unknown 16
Menispermaceae
     Menispermum canadense L. unknown 16
Myrtaccae
     Psidium guajava L.a unknown 16
Onagraceae
     Guara biennis L. unknown 16
     Oenothera biennis L. unknown 4,5
Oxalidaceae
     Oxalis corniculata L.b unknown 16
Papaveraceae
     Eschscholtzia californica Cham.a unknown 4, 5, 30
     Eschscholtzia mexicana Greene unknown this study
     Papaver nudicaule L.a linamarin and lotaustralin 53
Passifloraceae
     Passiflora foetida L. unknown 16
     Passiflora incarnata L. unknown 16
     Passiflora lutea L. unknown 54
     Passiflora suberosa L. unknown 55
Platanaceae
     Platanus acerifolia Willd.a,b unknown 29
     Platanus occidentalis L. unknown 29
Polypodiaceae
     Asplenium septentrionale (L). Hoffm. unknown 38
     Cheilanthes aemula Maxon. unknown this study
     Cheilanthes alabamensis (Buckl.) Kunze unknown 1
     Cheilanthes lanosa (Michx.) D.C. Eat. unknown 1
     Cystopteris bulbifera (L.) Bernh. unknown 1
     Cystopteris fragilis (L.) Bernh. prunasin 1, 29, 56
     Davallia braziliensis Hook.a unknown 26
     Davallia fijeensis Hook.a vicianin 56
     Dryopteris filix-max (L.) Schott. unknown 4, 5
     Pteridium aquilinum (L.) Kuhn prunasin 57,58
Ranunculacea
     Aquilegia canadensis L. unknown 1
     Aquilegia vulgaris L.a unknown 26
     Isopyrum biternatum (Raf.) T. & G. unknown 1
     Myosurus minimus L. unknown 16
     Ranunculus repens L. unknown 4,5
     Thalictrum aquilegifolium L.a proteacin, triglochinin methyl ester, p-(glucosyloxy)mandelonitrile 26,59,60
     Thalictrum dasycarpum Fisch. and All. unknown 16
Resedaceae
     Reseda alba L.a unknown 16
Rhamnaceae
     Rhamnus frangula L.a unknown 16,26
Rosaceae
     Amelanchier arborea (Michx. F.) Fern. unknown 6
     Aronia arbutifolia (L.) Ell. unknown 16
     Cotoneaster spp.a prunasin and amygdalin 61
     Eriobotrya japonica Lindl.a amygdatin 16,26
     Malus angustifolia (Ait.) Michx. unknown 16
     Photinia serrulata Lind.a unknown 16
     Photinia villosa D.C.a unknown 16
     Prunus armeniaca L.a prunasin and amygdalin 17
     Prunus caroliniana (Mill.) Ait. unknown 16
     Prunus cerasus L. prunasin and amygdalin 16
     Prunus laurocerasus Lind.a,b prunasin and amygdalin 62,63
     Prunus persica (L.) Batsch.a prunasin and amygdalin 62
     Prunus serotina Ehrh. prunasin 64
     Prunus virginiana L. unknown 1,17
     Pyracantha coccinea Roem.a,b unknown 16
     Sorbus aucuparia L. prunasin and amygdalin 1, 9
     Spiraea prunifolia Sieb. & Zucc.a,b unknown 16
     Spiraea japonica L.f.a,b unknown 16
Sapindaceae
     Cardiospermum halicacabum L. cyanolipids and an unknown glycoside 65,66
     Koelreuteria paniculata Laxm.a cyanolipids 68
     Sapindus drummondii H. & A. cyanolipids 66,67
     Ungnadia speciosa Endl. cyanolipids and two unknown glycosides 5,6,69
     Urvillea ulmacea HBK. cyanolipids 70
Solanaceae
     Datura stramonium L. unknown 16
     Lycium halimifolium Mill.a,b unknown 6
     Solanum, nigrum L.b unknown 16
     Solanum melongenaa unknown 72
Taxaceae
     Taxus cuspidata Sieb. & Zucc.a taxiphyllin 6,71
Turneraceae
     Turnera diffuse Willd. unknown 55, this study
Typhaceae
     Typha angustifolia L. unknown 16

a=cultivated
b=introduced
c=Sorghum vulgare and Sorghun sudanense are considered conspecific with or synonymous to Sorghum bicolor.

ACKNOWLEDGMENTS

I wish to acknowledge the financial support of NSF Grant BMS 75-02323 and Biomedical Research Funds HEW PHS RR 07030 toward the completion of this work.

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