Allelopathy in Mexican Plants - ACS Symposium Series (ACS

Chapter 17

Allelopathy in Mexican Plants

Downloaded by STANFORD UNIV GREEN LIBR on October 17, 2012 | http://pubs.acs.org Publication Date: December 9, 1994 | doi: 10.1021/bk-1995-0582.ch017

More Recent Studies A. L. Anaya, B. E. Hernández-Bautista, H. R. Pelayo-Benavides, M. Calera, and E. Fernández-Luiselli Instituto de Fisiologia Celular, Universidad Nacional Autónoma de México, Apartado Postal 70-243, México, 04510 D.F.

Research on allelopathy in Mexico has focused on plant species with ecological importance, some of them with medicinal use. Seeds, fungi and insects have been used in bioassays directed to assess activity of plant extracts and isolates. Allelochemicals can modify cellular structure and activities including respiration and division. Research priorities are based on the vast diversity of Mexican flora, its potential as a source of useful natural products, and the lack of knowledge in these areas. Researchers of different disciplines have found allelopathy increasingly interesting because of potential application of allelopathic compounds as herbicides, pesticides or growth regulators. Allelopathy may also be used to further manage biotic resources. The physiological effects of compounds with phytotoxic activity (allelochemicals, and/or herbicides) vary widely. Almost all of these compounds act with specificity on different groups of organisms. This characteristic renders them attractive in the search for new bio-active compounds (1). We are currently conducting studies on different species of Mexican plants with ecological or medicinal importance. Traditional knowledge, so rich in Mexico, has frequently suggested where to look for active compounds. Knowing that allelochemicals may affect different life organization levels -communities, organisms, tissues, cells, organelles and metabolic processes- plant extracts and isolated compounds have been evaluated using seeds, phytopathogenic fungi and insects as bioassays. Germination, growth, development, reproduction and survival are first determined, followed by the evaluation of the possible modes of action of tested compounds on processes such as respiration, cell division, enzymatic activities, and structural arrangements of tissues and cells.

0097-6156/95/0582-0224$08.00/0 © 1995 American Chemical Society In Allelopathy; Dakshini, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1994.

17.

ANAYAETAL.

Allelopathy in Mexican Plants: More Recent Studies

225


We try to focus our studies bearing in mind that Mexican biodiversity ranks fourth in the world, and hence represents a great chemical diversity. Yet, our knowledge of Mexican flora and fauna is incomplete, and the rate of disappearance of many species threatens its completion. Biotic and chemical impoverishment are equivalent. The loss of a species means loss of natural plant products which probably are unique in nature. There are also economic and social reasons that justify a search of active secondary metabolites. Regional issues could be identified and used to set research priorities. Chemical exploration could become part of biological conservation (2, 3, 4). Allelopathic potential of Mirabilis jalap a Mirabilis jalapa L. Nyctaginaceae (four o'clock) is an endemic Mexican plant that grows in disturbed sites. Roots and seeds are used as cathartics and the alkaloids jalapine and convolvuline are probably responsible for these effects. Other secondary compounds have been identified in M. jalapa such as quercetin, caffeic acid, trigonellin, alkaloids, tiramine and dopamine (5). Aqueous leachates of the plant have been shown to protect other plant from viral attack (6). Pelayo-Benavides (7) studied the effect of phytotoxic compounds of M. jalapa on cell division. The phytotoxic effects were determined by bioassays with several species of crops and weeds, using aqueous leachates and organic extracts. Alterations on cell division and root structure were evaluated in root tips of pea seedlings. The cell division was studied by measurements of mitotic index, phase index and cell cycle length. Cells were treated with colchicine to induced tetraploidy. The leachate of the dry aerial part (2% w/v) caused a significant decrease (31%) of mitotic activity. The duration of the cell cycle did not change, though fewer marked cells were found in the treated seedlings (Figure 1), probably due to a reduction in the number of meristematic cells in the roots.

Ratibida mexicana and Sesquiterpenic Lactones The species Ratibida mexicana (Wats.) Sharp (Asteraceae) is an endemic Mexican plant that has a scattered distribution in inaccessible areas along the Sierra Madre Occidental mountains in the state of Chihuahua. Tarahumara indians call this plant "Howinowa". They use its roots for the treatment of rheumatism and as an antiseptic agent. Certain sesquiterpenic lactones are implicated in allelopathy and possess a wide biological activity spectra, but their effects on phytopathogenic fungi have been scarcely studied. (8-12). Mata and collaborators (Mata, R., et al., Universidad Nacional Autonoma de Mexico, unpublished data) explored the effect of aqueous leachates and organic extracts of the root of Ratibida mexicana on the radicle growth of Amaranthus hypochondriacus (syn. A. leucocarpus) and Echinochloa crusgalli, and on the radial growth of some phytopathogenic fungi. Two sesquiterpenic lactones: Isoa/Zoalantolactone and Eleme-1,3-11-trien 8,12-olide (Figure 2) were isolated from hexane extracts of this plant. Figure 3 shows that Isoa/Zoalantolactone totally inhibited A. hypochondriacus growth at the three concentrations tested.

In Allelopathy; Dakshini, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1994.

ALLELOPATHY: ORGANISMS, PROCESSES, AND APPLICATIONS


226

9 10 11 TIME OF RECUPERATION (hours)

Figure 1.

Effect of the aqueous leachate of the dry aerial part (2% w/v) of Mirabilis jalapa on the cell cycle in the meristem of pea seedlings roots.

Elemenodienolide

lsoa//oalantolactone

Figure 2.

Chemical structure of the two sesquiterpenic lactones isolated from the hexanic extract of Ratibida mexicana.

0

_.

T

T

50

m 200

100 Treatment ug/ml

Figure 3.

Effect of isoalloalantolactone and elemenodienolide on the radicle growth of Amaranthus hypochondriacus and Echinochloa crusgalli.


17. ANAYA ET AL.


227

Elemenodienolide caused total inhibition of the radicle growth of this species at 100 and 200 |ig/ml. E. crusgalli was more resistant to both compounds. Table I shows that Isoa/Zoalantolactone and Elemenodienolide significantly inhibited the radial growth of Helminthosporium sp., and to a lesser extent, that of Pythium sp. Isoa//oalantolactone (200 |ig/ml) caused 50% inhibition of the radial growth of Fusarium oxyporum; this was the most resistant of the evaluated fungi.


Piqueria trinervia and Piquerols A and B Piqueria trinervia L (Compositae) is a ruderal species of the firsts stages of secondary succession in crop fields. It is used in herbal medicine as an antipyretic, antimalarian, antirheumatic, and to combat typhus and gallblader stones (13, 14). Gonzalez de la Parra et al. (15) demonstrated the phytotoxic activity of two diastereoisomers monoterpenes isolated by Romo et al. (16) from this species: Piquerol A and B. Jimenez-Estrada and collaborators (Jimenez-Estrada et al., Universidad Nacional Autonoma de Mexico, unpublished data), tested two derivatives of Piquerol A: 3isopropilen-2-methyl-l,4-benzenediol, and diacetyl-piquerol (Figure 4), and several synthetic phenols (Figure 5), on Amaranthus hypochondriacus and Echinochloa crusgalli. Table II shows the different effect of these compounds on growth. Piquerol A caused a significant stimulation of A. hypochondriacus at 10 jig/ml, and completely inhibited it at 100 |ig/ml. In general, benzenediol and diacetyl-piquerol exhibited a stronger inhibitory activity on A. hypochondriacus compared with Piquerol A. E. crusgalli was less sensitive to these compounds. The synthetic phenols were less active compared with Piquerol A and its derivatives. Gonzalez de la Parra et al. (17), tested piquerol A and B on larvae and gravid females of tick (Boophilus microplus), and confirmed their acaricide activity. This activity can be compared with that of the organophosphoric acaricides against larvae and gravid females of ticks. Piquerol A and B produced 100% of mortality after 3 days of application. However, these compounds do not prevent oviposition in ticks, as almost all synthetic acaricides do. Cruz-Ortega et al., (18) found that the H -ATPase activity of microsomes of Ipomoea purpurea radicle was inhibited (48.5%) by 500 J I M diacetyl-piquerol; this inhibition was higher in the plasma (67.2%) than in the tonoplast membranes (31.6%). In vivo, the plasma membrane ATPase might well be a more accessible target to the inhibitor than the tonoplast ATPase, given their respective cellular locations. These data suggest that the phytotoxicity of diacetyl-piquerol could be related to its effect on the plasma membrane H -ATPase. +

+

Corn Pollen and Phenylacetic Acid It has been shown that the practices used by some Mexican farmers to classify, select and use their weeds can be correlated with the allelopathic potential of these plants (19, 20, 21, 22). The allelopathic interaction between crops and weeds is carried out as a dynamic active release by aerial parts or roots and by decomposition.


228

ALLELOPATHY: ORGANISMS, PROCESSES, AND APPLICATIONS Table

I. Effect of Isoalloalantolactone and Elemenodienolide of Ratibida mexicana on the Radial Growth of Phytopathogenic Fungi


Treatments yMg/ml

Control 50 200

Isoalloalantolactone

2 days 100 40.9* 0*

Control 50 200

3 days 100 94.4* 55.0*

Control 50 200

3 days 100 0* 0*

Elemenodienolide

Radial growth (%) Pythium sp 3 days 2 days 3 days 100 100 82.2* 27.7* 78.5* 54.7* 0* 49.2* Fusarium oxyporum 8 days 3 days 8 days 100 100 100 91.4 87.7 92.5 86.0 59.0* 80.5* Helminthosporium sp. 8 days 3 days 8 days 100 100 100 0* 0* 0* 0* 0* 0*

*p < 0.05

\

OAc

OAc 3-lsopropilen-2-methyl-1,4-benzenediol Figure 4.

•acetyl - piquerol

Chemical structures of Piquerol A, 3-Isopropilen-2-methyl-l,4benzenediol and diacetyl-piquerol.


17. ANAYA ET AL.


OH

OH

O

229

O


OH 2,5-Dihydroxyacetophenone

OH

5-Allyloxy-2-hydroxyacetophenone

OH

O

O

OH 6-Allyl-2,5-dihydroxyacetophenone

Figure 5.

2,5-Dihydroxy-6-n-propylacetophenone

Phenols with chemical structures similar to Piquerol A .

Table II. Effect of Piquerol A and its Derivatives on Amaranthus hypochondriacus and Echinochloa crusgalli Treatment Radicle Growth (%) pglml A. hypochondriacus E. crusgalli Piquerol A 10 123.0* 82.0 30 70.6* 43.8* 100 0* 17.6* 3-isopropilen-2-methyl1,4-benzenediol 10 30 100 Diacetyl-piquerol 10 30 100 P < 0.001

50.5* 28.5* 0*

110.0* 78.6* 59.5*

45.8* 35.3* 0*

85.0* 62.0* 25.0*



230


Corn (Zea mays L) produces secondary compounds in leaves, roots, and pollen (hydroxarnic acids, phenylacetic, 4-phenylbutiric, benzoic, and o-hydroxyphenylacetic acids). Growth regulators (brassinosteroids: catasterone, typhasterol and teasterone), flavonoids (quercetine, isorhamnetine and kaempferol), and (3-carotene have been reported (23, 24, 25, 26). Some of these secondary metabolites posses allelopathic activity (27). Dzyubenko and Petrenko (28) described that root excretions of corn inhibit the growth of some weeds such as Amaranthus retroflexus. Chou and Patrick (29) reported that phenylacetic acid (PAA) and other compounds produced during decomposition of corn and rye residues in soil were highly inhibitory to the growth of lettuce. Jimenez-Osornio and Schultz (30) found that weed growth decreased in the middle of the crop cycle when corn was mature and flowering. Jimenez et al. (31) showed that the sprinkling of corn pollen over the seeds of Cassia jalapensis in sterilized and non sterilized soil, vermiculite and sand inhibited their growth. In this regard, some farmers in Mexico assert that the fruiting of squash, bottle gourd, and watermelon is reduced, and leaves of beans are "burnt" when corn pollen falls over them (32). Jimenez et al. concluded that the accumulation of pollen in the soil and its phytotoxic effects, particularly upon weeds, can give some advantage to corn over its potential competitors, especially during flowering. Some studies were conducted to identify the biochemical agents responsible for the allelochemical activity of corn pollen and their mode of action (32, 33). CruzOrtega et al. (33) found that an ethanolic extract of corn pollen acts as an inhibitor of the electron transport pathway, i.e., decreases oxygen consumption in watermelon mitochondria. A decrease of mitotic activity (more than 50%) of meristematic cells was also reported. The effects of a CH C1 extract of corn pollen, and six chromatographic fractions of this extract on Amaranthus hypochondriacus are shown in Table III. A l l the treatments (except fractions 5 and 6) produced significant reduction of radicle growth of A. hypochondriacus. Fraction 5 produced a stimulatory effect (28 %). The GC/EI-MS of fraction 3 confirmed the presence of phenylacetic acid (PAA) in it. Table IV shows the effects of fraction 3 and P A A on A. hypochondriacus and Echinochloa crusgalli. Fraction 3 showed the highest inhibitory activity on A. hypochondriacus, and P A A on E. crusgalli. These differences are probably due to different sensitivity in the two species tested and to the presence of other compounds, in addition to PAA, in fraction 3. Phenylacetic acid content in corn pollen probably contributed to the observed allelopathic effects (32). Fernandez-Luiselli (Fernandez-Luiselli, E., Universidad Nacional Autonoma de Mexico, unpublished data) carried out bioassays to establish the minimal dose of P A A needed to cause a significant inhibition (MID) on radicle growth of some crops and weeds. An average of 300 seeds of the tested species were sown in Petri dishes with agar (1.5%) and different concentrations of PAA. After 24 to 72 hours, depending on the species, germination and radicle growth were evaluated. Table V shows the MID on the tested species. A. hypochondriacus exhibited the highest sensitivity. Probably, the mode of action of P A A is related to its auxinic character. Pelayo-Benavides (Pelayo-Benavides, H.R., Universidad Nacional Autonoma de Mexico, unpublished data) compared the effect of P A A to those of other auxinic 2

2


17. ANAYA ET AL.



Table III. Effect of Methylene Chloride Extract of Corn Pollen and its Chromatographic Fractions on Amaranthus hypochondriacus Treatment jug/m\ Germination (%) Radicle Growth % Control

100

Methylene chloride extract 100

100

80.0

70.0*

80.0 82.0 76.6 96.6 90.0 90.0

44.2* 43.2* 23.2* 57.8* 128.4* 120.0

T L C fractions of CH C1 extract 100 2

1 2 3 4 5 6

2

R R R R R, R f

f

y

f

/

0.05 0.11 0.22 0.28 0.51 0.64

*P< 0.01

Table IV. Effects of a Thin Layer Chromatographic Fraction of CH C1 extract of Corn Pollen (Fraction 3) and PAA on Amaranthus hypochondriacus and Echinochloa crusgalli Treatments A. hypochondriacus E. crusgalli pglm\ Inhibition (%) Fraction 3 50 21.8* 52.7* 100 47.5* 75.6* 2

PPA 50 100 *P < 0.05

2

30.6* 62.2*

48.0* 53.0*


231


232


Table V. Minimal Inhibition Dose (MID) of PAA for the Tested Plant Species INHIBITION* % MID Species 6

13.66

5

5.88

5

5.23

4

9.16

4

21.76

4

53.62

4

18.58

Amaranthus hypochondriacus

7.35 x 10" M

Ipomoea purpurea

1.17 x 10" M

Cucurbita pepo

3.30 x 1 0 M

Zea mays

1.38 x 1 0 M

Echinochloa crusgalli

1.41 x 1 0 M

Phaseolus vulgaris

5.35 x 10" M

Cucurbita ficifolia

5.23 x 10- M

* Caused by MID, as compared to the control.



17. ANAYA ET AL.


233

compounds: IAA, 2,4-D and H P A A on the development (first 48 hours) of Amaranthus hypochondriacus. Figure 6 shows the response of radicle growth to different molar concentrations of the compounds. There is a sigmoidal inhibitory effect of IAA and 2,4-D on the growth of A. hypochondriacus. On the other hand, the inhibitory effect of P A A and H P A A is exponential. In relation to the IC50 (Table VI), the order of activity was the following: 2,4-D>IAA>PAA>HPAA. This seems to be related to the water solubility of these compounds (HPAA>PAA>IAA>2,4-D). Depending on concentration, these compounds (except HPAA) produced morphological changes in the radicle and negative geotropism. P A A promotes some structural changes, for example, displacement of the maturation point of the xylematic elements. Ipomoea tricolor and Tricolorin A The genus Ipomoea (Convolvulaceae) includes about 600 species. Its richness in secondary metabolites with biological activity is perhaps its most remarkable characteristic. In Mexico, the seeds of Ipomoea tricolor ("tlitlitzin", "badoh negro" or "dondiego de dia"), as well as those of the related species Turbina corymbosa (L.) Raf. ("ololiuqui" or snake plant), are used as hallucinogens in tribal rituals. This activity is due to their content of ergot type alkaloids. Other species of Ipomoea are widely used as powerful cathartics, an activity related to the presence of glycosidic resins. These glycosides have been reported as antimicrobials and antitumorals (34). The related species I. aquatica and /. batatas contain terpenoids and phenolic compounds with allelopathic activity (35). Anaya et al. (36) confirmed that in tropical Mexico, some farmers use certain weeds to control the growth of others. Some Ipomoea species are used for this purpose. In the sugar cane fields of the state of Morelos, I. tricolor is grown as a cover crop from August to October. This plant eliminate all other weeds in two or three months. After this time, the plant is reaped and incorporated into the soil. Anaya et al. (op cit.) described the phytotoxic activity of /. tricolor, testing aqueous leachates and organic extracts of the plant on seedling growth of Amaranthus hypochondriacus and Echinochloa crusgalli. Bioactivity-directed fractioning of the active CHCI3 extract of the plant led to the isolation of a phytotoxic compound, which turned out to be a mixture of the so-called "resin glycosides" of convolvulaceous plants. Pereda-Miranda et al., (37) elucidated the structure of tricolorin A as (11 S)-hydroxyhexadecanoic acid 11-O-oc L-rhamnopyranosyl-( l—>3) 0 - a - L - { 2-0- ( 2S - methylbutyryl ) - 4 - 0 - ( 2S-methylbutyryl ) } rhamnopyranosyl- ( 1^2 ) - 0 - (J - D - glucopyranosyl - ( l->2 ) - (3 -Dfucopyranoside-( 1,3"-lactone) (Figure 7). Tricolorin A significantly inhibited radicle growth of the tested plants. Figure 8 shows the effects of tricolorin A and 2,4-D on both tested species. Radicle growth was evaluated after 24 h for A. hypochondriacus, and 48 h for E. crusgalli. Staphylococcus aureus was sensitive to the compound; the minimal inhibition concentration (MIC) was 1.8 ^tg/ml. This compound exhibited significant cytotoxic activity on cultured P-388 and human breast cancer cells (ED50



234


MOLAR CONCENTRATION (log) HPAA - B - PAA

Figure 6.

— H - IAA

2,4-D

Effect of HPAA, P A A , I A A and 2,4-D on the radicle growth of Amaranthus hypochondriacus.

50

Table VI. IC of Tested Compounds on Radicle Growth of Amaranthus hypochondriacus Compounds IC50 HPAA

3.98 X 10 M

PAA

3.98 X 10- M

IAA

3.00 X 10" M

2,4-D

1.00 X 10" M

4

5

7

7



235


17. ANAYA ET AL.

Figure 8.

Effect of different concentrations of Tricolorin A and 2,4-D on the radicle growth of Amaranthus hypochondriacus and Echinochloa crusgalli.


236


2.2 |ig/ml), and inhibited phorbol 12,13-dibutyrate binding when calf brain homogenate was used as a source of protein kinase C (IC50 43 pM). Calera (Calera, M.R., Universidad Nacional Autonoma de Mexico, unpublished data), studied if the inhibitory effect of the resin glycoside from Ipomoea tricolor on radicle growth of Echinochloa crusgalli, was related to an effect on its plasma membrane H -ATPase activity. Table VII shows the effect of the resin glycoside on ATPase activity of vesicles at different levels of purification. In the U3 fraction, which constitutes a highly purified (about 90%) plasma membrane fraction, the resin glycoside inhibited ATP hydrolysis in about 30 % as compared to an inhibition of 10% in the microsomal fraction or 18% in the U2 fraction (less purified plasma membrane fraction). In consequence inhibition of ATP hydrolysis in the U3 fraction was due to an effect of the resin on the plasma membrane ATPase, since it is the major ATP hydrolytic component.


+

Brassicaceae and Glucosinolates Different species of Brassicaceae (Cruciferae) have been reported as allelopathic plants [Brassica oleraceae and B. campestris, (38)]. Plants of this family produce glucosinolates that do not have auto allelopathic effects (39). Glucosinolates of Cruciferae are of special interest because in this family there are several common edible plants as cabbage, broccoli and turnip. Glucosinolates are not volatile but their salts are with a characteristic strong odor. More than 20 volatile sulfur compounds have been identified in cabbage (isothiocyanates, sulfides, disulfides, trisulfides and mercaptanes) (40, 41, 42). These metabolites are toxic to Colletotrichum circinans and Botrytis alii. Mercaptanes prevent the germination of sclerotia of Sclerotium cepivorum. Isothiocyanates inhibit mycelial growth, and formation, motility and germination of zoospores in Aphanomyces euteiches. These compounds also modify larval activity of parasitic root nematodes Meloidogyne incognita and Nacobbus aberrans (43). Celaenodendron mexicanum. Terpenoids and Flavonoids Castaneda et al. (44) identified terpenoids and flavonoids (Figure 9) in Celaenodendron mexicanum (Euphorbiaceae), an endemic tree of the Pacific Coast of Mexico. The biological effects of aqueous leachates, a CHCl3-MeOH extract and the isolated compounds of leaves and twigs (100 pg/ml) were evaluated on the radicle growth of Amaranthus hypochondriacus and Echinochloa crusgalli, and on the radial growth of phytopathogenic fungi. Flavonoids (bilobetin and amentoflavone) inhibited approximately 18-25% the growth of A. hypochondriacus, and triterpenes (friedelin, maytensifolin B) inhibited almost 40% the growth of E. crusgalli. In natural conditions, C. mexicanum causes a significant ecological effect on different organisms in the community. The almost year around bearing of foliage causes a constant light reduction that necessarily affects the growth of other species. Its richness in secondary compounds could contribute to its influence on the micro environment.


17. ANAYA ET AL.

237


Table VII. Effect of the Resin Glycoside on ATP Hydrolysis from Purified Plasma Membrane Vesicles at Different Levels of Purification ATP HYDROLYSIS (nmol Pi min" mg protein-" ) M.F. U U 1

1


2

3

Control

566.0 ± 0.5 (100%)

432.0 ± 1.9 (100%)

843.0 ± 1.3 (100%)

Vanadate

462.0 ± 0.5 (82%) 506.5 ± 0.5 (90%)

106.0 ± 0.9 (24%) 358.8 ± 8.7 (83%)

101.4 ± 2.3 (12%)* 576.8 ± 0.6 (68%)*

Resin

*P < 0.05, A N O V A . Assays were conducted on microsomal fraction (M.F.) or U and U fractions of purified plasma membrane vesicles by succesive phase partitioning (1 jug of protein). ATP hydrolysis was measured as described under Materials and Methods. Each value represents the means of four samples ± SE. 2

R = O, R, = H

FRIEDELIN

R =R =O

MAYTENSIFOLIN

1

R = p-OH, R = O 1

Figure 9.

3

3-[3-HY DROXY-FRIE DE LAN-16-ONE

Chemical structures of terpenoids and flavonoids isolated from Celaenodendron mexicanum.


238

ALLELOPATHY:

ORGANISMS, PROCESSES, AND APPLICATIONS


Swietenia humilis and Limonoids Swietenia humilis Zuccarini (Meliaceae), locally known as "zopilote", "cobano", "caobilla", and "sopilocuahuitl" grows commonly in tropical Mexico. In some regions, the seeds of this plant are highly valued for their medicinal properties. Infusions of ground seeds are used as antihelminthic and to treat amebiasis. They are considered effective for treatment of chest pain, coughs, and cancer. S. humilis has recently been listed as an endangered species in need of protection. Segura-Correa et al. (45) isolated from the seeds of this species four new tetranortriterpenoids with the same limonoid type skeleton: humilinolides A, B, C, and D (Figure 10). Limonoids possess a wide range of biological activities, including insect antifeedant and growth regulating properties, a variety of medicinal effects in animals and humans, and antifungal, bacteriocidal, and antiviral activity. The effect of the MeOH extract of the seeds and the isolated terpenoids on the radicle growth of Amaranthus hypochondriacus and Echinochloa crusgalli was evaluated. The radicle growth inhibitory concentration (IC ) of the extract was 275.9 pg/ml for A. hypochondriacus, and 171.5 jig/ml for E. crusgalli. Humilinolides A and C inhibited the radicle growth of E. crusgalli with I C values of 99 Jig/ml and 163 |ig/ml respectively. A. hypochondriacus was less sensitive to these compounds with values of 199 jig/ml and 215 |Xg/ml respectively. When the MeOH extract of the seeds was administered to the third instar larvae of Tenebrio molitor on a diet containing 1% of the extract, both feeding and growth were significantly reduced. When the concentration of the extract was 0.5%, only a feeding deterrent action was obtained. No mortality was observed at these two concentrations tested. 50

5 0


17.

ANAYA ET AL.


239


Final Considerations It was until 1989 that research on Chemical Ecology in Mexico began to take more impulse. This is ironic because in the 60's Lincoln Brower's classic studies on the evolutionary ecology of toxic plants and their associates herbivores (46-47) were carried out with Mexican Monarch butterfly. This example of chemical interaction represents one of the most beautiful and spectacular in ecology and chemical evolution. Mexico should be a particularly propitious place for this kind of studies because of its great biological and ethnobiological richness which implies a diversity of management methods of natural resources practiced by the different ethnic groups of the country.(48).

Literature Cited 1. Einhellig, F.A. In Handbook of Natural Pesticides: Methods. Theory, Practice, and Detection. CRC Press, Inc.: Boca Raton, Fl, 1985, Vol. 1; pp. 161-200. 2. Eisner, T. In Ecology, Economics, and Ethics: The Broken Circle. Yale University Press: New Haven, Co., 1989; pp. 4-16. 3. Gómez-Pompa. A. Los Recursos Bióticos de México (Reflexiones). Instituto Nacional de Investigaciones sobre Recursos Bióticos. Ed. Alhambra Mexicana: México, D.F., 1985. 4. Anaya, A . L . ; Cruz Ortega, R ; and Nava Rodriguez, V. 1992. In Allelopathy: Basic and applied aspects; Rizvi, S.J.H., and Rizvi, V., Eds.; Chapman and Hall: London; pp. 271-301. 5. Hegnauer, R. Chemotaxonomie der Pflanzen. Verlag: Basel Birkhauser, Band 5., 1969. 6. Ikeda, T.; Takanami, Y.; Imaizumi, S.; Matsumoto, T.; Mikami, Y.; and Kubo, S. Plant Cell Rep. 1987, 6, 216-218. 7. Pelayo-Benavides, H.R. Efecto de los compuestos fitotóxicos de Mirabilis jalapa L. (Nyctaginaceae) sobre la división celular. Escuela Nacional de Ciencias Biológicas. Instituto Politécnico Nacional: México, D.F., 1991; 51 pp. 8. Amo, R. S. del; and Anaya, A . L . J. Chem. Ecol. 1978, 4, 305-313. 9. Rodriguez, E . ; Towers, G.H.N.; and Mitchell, J.C. Phytochemistry 1976, 15, 1573-1580. 10. Stevens, K . L . ; and Merrill, G.B. In The Chemistry of Allelopathy: Biochemical Interactions among Plants. Thompson, A.C., Ed.; ACS Symposium Series 268. Washington, D.C., 1985; pp. 83-98. 11. Fischer, N.H. J. Chem. Ecol., 1989, 15, 1785-1793. 12. Macías, F.A.; Galindo, J.C.G.; and Massanet, G.M. Phytochemistry 1992, 6, 1969-1977. 13. Martínez, M . Las Plantas Medicinales de México. Ediciones Andrés Botas: México, D.F., 1969. 14. Paray, L. Bol. Soc. Bot. Mex. 1953, 15,1-12 15. González de la Parra, M . ; Anaya, A.L.; Espinoza, F.J.; Jiménez, M . ; and Castillo, R. J. Chem. Ecol. 1981, 7, 509-515. 16. Romo, J.; Romo de Vivar, A.; Quijano, L.; Rios, T.; and Diaz, E . Rev. Latinoam. de Quím. 1970, 1, 72-81. In Allelopathy; Dakshini, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1994.


240


17. González de la Parra, M . ; Chávez-Peña, D.; Jiménez-Estrada, M . ; and RamosMundo, C. Pestic. Sci. 1991, 33, 73-80. 18. Cruz Ortega, R.; Anaya, A . L . ; Gavilanes-Ruíz, M . ; Sánchez Nieto, S.; and Jiménez Estrada, M . J. Chem. Ecol. 1990, 16, 2253-2261. 19. Chacon, J.C.; and Gliessman, S.R. Agro-Ecosystems. 1982, 8, 1-11. 20. Gliessman, S.R. J. Chem. Ecol. 1983, 9, 991-999. 21. Kahl, H . J. Agronomy &Crop Science, 1987, 158, 56-64 22. Anaya, A . L . ; Ramos, L.; Cruz-Ortega, R.; Hernández, J.; and Nava, V . J. Chem. Ecol., 1987, 13, 2083-2101. 23. Argadoña, H.V.; and Corcuera, J.L. Phytochemistry 1985, 24, 177-178. 24. Suzuki, Y.; Yamaguchi, I.; and Yokota, T. Agric. Biol. Chem. 1986, 12, 31333138. 25. Ceska, O.; and E.D. Styles. Phytochemistry 1984, 23, 1822-1823. 26. Stanley, R . G . ; and Linskens, H.R. Pollen: Biology, Biochemistry and Management. Springer-Verlag: Berlin, 1974. 27. Anaya, A . L . , Cruz Ortega, R., y Nava Rodriguez, V. In: Allelopathy: Basic and applied aspects. Rizvi S.J.H. and V . Rizvi (Eds.). Chapman and Hall: London., 1992; pp. 271-301. 28. Dzyubenko; N.N.; and Petrenko, N.I. In Physiological-Biochemical Basis of Plant Interactions in Phytocenosis. Vol. 2. Naukova Dumka: Kiev (in Russian with English summary)., 1971; pp. 60-66. 29. Chou, Ch-H.; and Patrick, Z.A. J. Chem. Ecol. 1976, 2,369-387. 30. Jiménez-Osornio, J. J.; and Schultz, K., Interacciones entre lasplantas cultivadas y las plantas arvenses en una chinampa. Facultad de Ciencias, U N A M : México, D.F., 1981; 75 pp. 31. Jiménez-Osornio, J.J.; Anaya, A.L.; Schultz, K.; Hernandez, J.; and Espejo, O. J. Chem. Ecol. 1983, 9, 1011-1025. 32. Anaya, A . L . ; Hernández-Bautista, B.E.; Jiménez-Estrada, M . ; and Velasco-Ibarra, L. J. Chem. Ecol. 1992, 18, 897-905. 33. Cruz-Ortega, R.; Anaya, A.L.; and Ramos, L. J. Chem. Ecol. 1988, 14, 71-86. 34. Bieber, L.W.; Alves Da Silva Filho, A.; Correa Lima, R.M.O.; De Andrade Chiappeta, A.; Carneiro Do Nascimento, S.; De Souza, I.A; De Mello, J.F.; and Veith, H.J. Phytochemistry 1986, 25,1077-1081. 35. Howard, F.H.; and Peterson, J.K. Weed Sci. 1986, 4, 623-627. 36. Anaya, A . L . ; Calera, M.R.; Mata, R.; and Pereda Miranda, R.. J. Chem. Ecol. 1990, 16, 2145-2152. 37. Pereda-Miranda, R.; Mata, R.; Anaya, A.L.; Wickramaratne, D.B.; Pezzuto, J.M.; and Douglas Kinghorn,, A. J. Natural Products, 1993, 56, 571-582. 38. Jiménez-Osornio, J.J.; and Gliessman, S.R. In: Allelochemicals: Role in Agriculture and Forestry. Waller, G.R. Ed.; American Chemical Society: Washington, D.C., 1987; pp. 262-274. 39. Cole, A.R. Phytochemistry. 1976, 15, 759-762. 40. Bailey, S.D.; Bazinet, M . L . , Driscolland, J.L.; and McCarthy, A.I. J. Food Sci. 1960, 26,163-170. 41. MacLeod, A.J.; and MacLeod, G. J. Sci. Food. Agr. 1968, 19, 273-277. 42. Lewis, J. A.; and Papavizas, G.C. Soil Biol. Biochem. 1970, 2, 239-246.



17. ANAYA ET AL.


241

43. Zavaleta-Mejia, E . ; Reyna, I.; Rojas, M . ; and Zavaleta, L . M . In Report on the Workshop on Chemica Interactions Betwen Organisms. International Foundation for Science (IFS): Santiago, Chile, 1989, pp. 118-123. 44. Castañeda, P.; García, M.R.; Hernández, B.E.; Torres, B.A.; Anaya, A . L . ; and Mata, R. J. Chem. Ecol. 1992, 18, 1025-1037. 45. Segura-Correa, R.; Mata, R.; Anaya, A . L . ; Hernandez-Bautista, B.; Villena, R.; Soriano-Garcia, M . ; Bye, R.; and Linares, E . J. Nat. Prod. 1993, 56, 1567-1574. 46. Brower, L.P.; Brower, J.V.Z.; and Collins, C.T. Zoologica (N.Y.) 1963, 48; 6584. 47. Brower, L.P.; Ryerson, W.N.; Coppinger, L . L . ; and Glazier, S.C. Science 1968, 161, 1349-1351. 48. Dirzo, R.; and Anaya, A.L. In Resumenes de la I Reunión Nacional de Ecología Quimica. Instituto de Fisiología Celular y Centro de Ecología. Universidad Nacional Autónoma de México. México, D.F., 1989; pp. 9-10. RECEIVED May 17,

1994


Allelopathy in Mexican Plants - ACS Symposium Series (ACS

Recommend Documents