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Artemisinin, a Constituent of Annual Wormwood (Artemisia annua), is a Selective Phytotoxin

Published online by Cambridge University Press:  12 June 2017

Stephen O. Duke ,
Kevin C. Vaughn ,
Edward M. Croom Jr.  and
Hala N. Elsohly
Stephen O. Duke
Affiliation:
U.S. Dep. Agric., Agric. Res. Serv., Southern Weed Science Lab., P.O. Box 350, Stoneville, MS 38776
Kevin C. Vaughn
Affiliation:
U.S. Dep. Agric., Agric. Res. Serv., Southern Weed Science Lab., P.O. Box 350, Stoneville, MS 38776
Edward M. Croom Jr.
Affiliation:
Res. Inst. of Pharmaceutical Sciences, School of Pharmacy, Univ. Mississippi, University, MS 38677
Hala N. Elsohly
Affiliation:
Res. Inst. of Pharmaceutical Sciences, School of Pharmacy, Univ. Mississippi, University, MS 38677
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Abstract

Artemisinin (qinghaosu), a sesquiterpenoid lactone peroxide constituent of annual wormwood (Artemisia annua L. # ARTAN) that is used as an antimalarial drug, was tested for phytotoxic properties. It inhibited germination of lettuce (Lactuca sativa L.) and annual wormwood, and growth of roots and shoots of lettuce, redroot pigweed (Amaranthus retroflexus L. # AMARE), pitted morningglory (Ipomoea lacunosa L. # IPOLA), annual wormwood, and common purslane (Portulaca oleracea L. # POROL) was inhibited at 33 μM. No effects of 33 μM artemisinin were detected on growth of velvetleaf (Abutilon theophrasti Medik. # ABUTH) and grain sorghum [Sorghum bicolor (L.) Moench.]. Chlorophyll content was not affected in lettuce, and chlorosis was not observed in any species tested. The probable biosynthetic precursors of artemisinin, arteannuin B and qinghao acid, had no effect on growth or chlorophyll content of lettuce; however, they inhibited lettuce seed germination. Artemisinin and cinmethylin {exo-1-methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-7-oxabicyclo [2.2.1] heptane} were equally effective in reducing growth of lettuce; however, cinmethylin had no effect on germination. Respiration of lettuce roots or cotyledons was not inhibited by artemisinin. Artemisinin only marginally increased the mitotic index of lettuce root tips at 33 μM. At the ultrastructural level, however, chromosomes were less condensed during mitosis in artemisinin-treated than control meristematic cells. The growth-inhibiting ability of artemisinin could not be reduced by feeding the plants with hydrolyzed protein or treatment with putrescine. Artemisinin is a selective phytotoxin that reduces growth by a mechanism other than mitotic disruption or inhibition of protein synthesis.

Keywords

Allelochemicalarteannuin Bcinmethylinqinghaosuqinghao acidterpenoid
Type
Weed Biology and Ecology
Information
Weed Science , Volume 35 , Issue 4 , July 1987 , pp. 499 - 505
Copyright
Copyright © 1987 by the Weed Science Society of America 

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References

Literature Cited

1. China Cooperative Research Group. 1982. Chemical studies on qinghaosu (artemisinin). J. Tradit. Chin. Med. 2:3–8.Google Scholar
2. Duke, S. O. 1978. Significance of fluence-response data in phytochrome-initiated seed germination. Photobiol. Photochem. 28:383–388.CrossRefGoogle Scholar
3. Duke, S. O. 1986. Microbial toxins as herbicides – a perspective. Pages 287–304 in Putnam, A. R. and Tang, C. S., eds. The Science of Allelopathy. Wiley-Interscience, New York.Google Scholar
4. Duke, S. O. 1986. Naturally occurring chemical compounds as herbicides. Rev. Weed Sci. 2:15–44.Google Scholar
5. El-Deek, M. H. and Hess, F. D. 1986. Inhibited mitotic entry is the cause of growth inhibition by cinmethylin. Weed Sci. 34:684–688.CrossRefGoogle Scholar
6. Gresshoff, P. M. 1979. Growth inhibition of Arabidopsis thaliana by glyphosate and reversal of its action by phenylalanine and tyrosine. Arabidopsis Inf. Serv. 16:73–75.Google Scholar
7. Gu, H. M., Warhust, D. C., and Peters, W. 1983. Rapid action of qinghaosu and related drugs on incorporation of [3H]isoleucine by Plasmodium falciparum in vitro. Biochem. Pharmacol. 32:2463–2466.CrossRefGoogle ScholarPubMed
8. Grümmer, G. 1961. The role of toxic substances in the interrelationships between plants. Pages 219–228 in Milthorpe, F. L., ed. Mechanisms in Biological Competition. Academic Press, New York.Google Scholar
9. Halligan, J. P. 1975. Toxic terpenes from Artemisia californica . Ecology 56:999–1003.CrossRefGoogle Scholar
10. Hiscox, J. D. and Israelstam, G. F. 1979. A method for the extraction of chlorophyll from leaf tissue without maceration. Can. J. Bot. 57:1332–1334.CrossRefGoogle Scholar
11. Holmsen, J. D. and Hess, F. D. 1985. Comparison of the disruption of mitosis and cell plate formation in oat roots by DCPA, colchicine, and propham. J. Exp. Bot. 36:1504–1513.CrossRefGoogle Scholar
12. Jeremic, D., Jokic, A., Behbud, A., and Stefanovic, M. 1973. A new type of sesquiterpene lactone isolated from Artemisia annua L. Arteannuin B. Tetrahedron Lett. 32:3039–3042.CrossRefGoogle Scholar
13. Klayman, D. L. 1985. Qinghaosu (Artemisinin): an antimalarial drug from China. Science 228:1049–1055.CrossRefGoogle ScholarPubMed
14. Klayman, D. L., Lin, A. J., Acton, N., Scovill, J. P., Hoch, J. M., Milhous, W. K., and Theoharides, A. D. 1984. Isolation of artemisinin (qinghaosu) from Artemisia annua growing in the United States. J. Nat. Prod. 47:715–717.CrossRefGoogle ScholarPubMed
15. McCahon, C. B., Kelsey, R. G., Sheridan, P. P., and Shafizadeh, F. 1973. Physiological effects of compounds extracted from sagebrush. Bull. Torrey Bot. Club 100:23–28.CrossRefGoogle Scholar
16. May, J. W., Goss, J. R., Moncorge, J. M., and Murphy, M. W. 1985. SD 95481 a versatile new herbicide with wide spectrum crop use. Proc. Br. Crop Protect. Conf. 12:265–270.Google Scholar
17. Muller, W. H. and Muller, C. H. 1964. Volatile growth inhibitors produced by Salvia species. Bull. Torrey Bot. Club 91:327–330.CrossRefGoogle Scholar
18. Smith, T. A. 1985. Polyamines. Annu. Rev. Plant Physiol. 36:117–143.CrossRefGoogle Scholar
19. Vaughn, K. C. 1986. Cytological studies of dinitroaniline-resistant Eleusine . Pestic. Biochem. Physiol. 26:66–74.CrossRefGoogle Scholar
20. Whaun, J., Brown, N., Milhous, W., Lambros, C., Scovill, J., Lin, A., and Klayman, D. 1985. Qinghaosu, a potent antimalarial, perturbs polyamine metabolism in human malaria cultures. Pages 301–310 in Imahori, et al., eds. Polyamines: Basic and Clinical Aspects. VNU Science Press, Utrecht, Netherlands.Google Scholar
21. You-you, T., Mu-yun, N., Yu-rong, Z., Lan-na, L., Shu-lian, C., Mu-qun, Z., Xiu-zhen, W., Zheng, J., and Xiao-tian, L. 1982. Studies on the constituents of Artemisia annua Part II. Planta Medica 44:143–145.CrossRefGoogle ScholarPubMed
22. Zhau, Y., Hauton, W. K., and Lee, K. -H. 1986. Antimalarial agents. 2. Artesunate, an inhibitor of cytochrome oxidase activity in Plasmodium berghei . J. Nat. Prod. 49:139–142.CrossRefGoogle Scholar