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Occurrence of Sesbanimide in Seeds of Toxic Sesbania Species! Abstract

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Occurrence of Sesbanimide in Seeds of Toxic Sesbania Species! Abstract Weed Science. 1990. Volume 38:148-152 Occurrence of Sesbanimide in Seeds of Toxic Sesbania Species! RICHARD G. POWELL. RONALD D. PLAITNER. and MATIHEW SUFFNESS2 Abstract. A tandem mass spectrometric procedure was sheep (Ovis spp.). and pig (Sus spp.) (10). Reports of natural developed to detect sesbanimide A and its isomers in plant poisonings have appeared in the veterinary literature from the materials. Analysis of seed extracts from 10 Sesbania late 1800s to the present (1, 11, 18). and results of species using this procedure readily detected sesbanimides experimental poisonings have been described (3. 4, 5). in Drummond rattlebush, rattlebush, and bagpod ses· Clinical signs and lesions are similar in all cases and include bania. The toxic sesbanimides were not detected in hemp various internal hemorrhages and degenerative changes in sesbania or in other species with no known history of vital organs. Seeds of these plants tend to remain in the pods animal toxicity. Nomenclature: Sesbanimide A, 4-(5'­ and attached to erect woody stems long after the leaves have hydroxy - 6'·(2" - hydroxy - 3"-methyl-4"-methylene­ fallen; natural poisonings usually occur only when animals tetrahydrofuran • 2" - yl) - 1',3' • dioxan-4' - yl)­ have no other choice of food. piperidine - 2,6 - dione; Drummond rattlebush, Sesbania Attempts to characterize the Sesbania toxin occupied drummondii (Rydb.) Cory 13 SEBDR; rattlebush, Sesbania many investigators over the years. Weedon (19) reported that punicea (Cav.) Benth. # SEBPU; bagpod sesbania, bagpod sesbania contained no alkaloids or cyanogenic Sesbania vesicaria (Jacq.) Ell. # SEBVI; hemp sesbania, glycosides. Others (6. 17) indicated that saponins might Sesbania exaltata (Raf.) Rydb. ex A. W. Hill # SEBEX. account for the toxicity; however, attempts to purify saponins Additional index words. Fabaceae, poisonous weed, mass resulted in near or total loss of the toxic factor (10, 13, 14). spectrometry, glutarimide derivative, Sesbania drummon­ Thus. in contrast to impressions from the earlier literature. dii, Sesbania vesicaria, Sesbania punicea, Sesbania exaltala, Sesbania saponins appear to be relatively harmless. SEBDR, SEBEX, SEBPU, SEBVI. Isolation of sesbanimide. an antitumor-active compound from Drummond rattlebush. was reported in 1983 (15). The INTRODUCTION isolation was guided using cytotoxicity of fractions in tumor cell cultures and toxicity of fractions in leukemic mice Three legumes. usually regarded as Sesbania species and according to National Cancer Institute protocols (7). This commonly occurring in disturbed areas along the Southern report was quickly followed by another from South Africa (9) Atlantic and Gulf Coastal Plains, have long been known to be that sesbanirnide had also been isolated from rattlebush. The toxic to livestock and fowl (11). Some confusion exists in the data in both instances clearly demonstrated that sesbanirnide taxonomic literature, as several Latin names and many A was the primary toxin. although two analogs. sesbanirnides common names have been used for their identification (8, B and C; were also reported. The sesbanimides are 11). A few of the more common synonyms are as follows: structurally related to the glutarimide group of antibiotics. Drummond rattlebush [So drummondii (Rydb.) Cory # including cycloheximide and streptimidone (Figure 1). which SEBDR = Daubentonia longifolia DC. (in part) = D. are commonly present in cultures of various Streptomyces drummondii], coffeebean. rattlebush. rattlebox; rattlebush [So species. Sesbanimide A is relatively unstable. and consider­ punicea (Cav.) Benth. # SEBPU = D. punicea (Cav.) DC. = able losses may be encountered during isolation (16). The D. longifolia DC. (in part)]. purple sesbane, purple rattlebox; maximum amount recovered from rattlebush was reported to bagpod sesbania [So vesicaria (Jacq.) Ell. # SEBVI = S. be 102 mg from 4.5 kg of seed (9). platycarpa Pers. = Glottidium vesicarium (Jacq.) Harper], Occurrence of sesbanimide A in seeds at such very low bagpod. bladderpod, and coffeebean. These species are often levels. combined with observations of its inherent instability found along roadsides or in unimproved pastures. and under conditions often encountered during isolation of natural Drummond rattlebush is beginning to appear in some soybean products. led to the present study to confirm the presence and [Glycine max (L.) Merr.] fields (2). Rattlebush is also estimate the concentration of sesbanimide A in seed extracts. considered to be a noxious weed in southern Africa (9). Since there are no published methods to rapidly identify Seeds of Drummond rattlebush. rattlebush. and bagpod sesbanimide in plant extracts. we decided to employ tandem sesbania are toxic to chicken (Gallus spp.), cattle (Bos spp.). mass spectrometry for this purpose. This technique is sensitive and rapid, and can be used to identify target compounds in relatively crude plant extracts (12). lReceived for publication May 21, 1988. and in revised form February 3, 1990. MATERIALS AND METHODS 2Res. Leaaer and Res. Chern., U.S. Dep. Agric.. Agric. Res. Serv.• North Reg. Res. Ctr.. 1815 N. University St.. Peoria, IL 61604; Program Seeds from 11 accessions of Sesbania and one other Coordinator for Natural Products. Nat. Cancer Inst.. Room 832 E.P.N., NIH, species (Senecio abrotanifolius. L.. NU 45644) were selected Bethesda. MD 20892. 3Letters following this symbol are a WSSA-approved computer code from the collection at the Northern Regional Research Center. from Composite List of Weeds, Weed Sci. 32. Suppl. 2. Available from Reference numbers and origins of the Sesbania samples are WSSA. 309 West Clark Street. Champaign, lL 61820. listed in Table 1. These were obtained and their identifica- 148 WEED SCIENCE O/"'.-O O/"'.-O 0 ..-...- OH 0 0 Sesbanimide A O/"'.-O CH 0 CH 2 2 Sesbanimide B Sesbanimide C Cycloheximide Streptimidone Figzue 1. Structures of sesbanimide A and related compounds. tions confinned by botanists at the Beltsville Agricultural hexane in a soxhlet apparatus to remove lipids and then Research Center. Beltsville. Maryland. further extracting the seed meals with 95% (v/v) ethanol. Sample preparation. Seed samples. routinely 50 g, were Animal tests were conducted in accordance with protocol fmely ground and extracted with methanol in a soxhlet 1.200 as described by Geran et al. (7). apparatus. Methanol solubles were then partitioned between Analytical procedures. All mass spectrometry (MS)4 experi­ hexane and 50% aqueous methanol (v/v). The resulting ments were conducted in a triple-stage quadrupole mass aqueous methanol solutions were extracted with dichloro­ spectrometerS. Samples were introduced into the mass methane; dichloromethane solubles were evaporated to spectrometer by means of a solids probe which was dryness, weighed, and then redissolved in 1 ml dichlorometh­ ballistically heated to 300 C. Ions were generated by ane. Samples of IJ.11 each, 50-J.1g equivalents of the original chemical ionization with isobutane (at about 0.3 Torr). For seed samples, were then analyzed by mass spectrometry. tandem MS experiments (MS/MS), the selected parent ions Ethanol extracts submitted to the National Cancer Institute were mass selected by the fIrst quadrupole, and collision­ were prepared by ftrst extracting ground seed samples with activated dissociation daughters were generated at an ion kinetic energy of 20 eV by collision with argon gas at a pressure of 1 mTorr. Daughter spectra were obtained by scanning the third quadrupole over the mass range 40 to 350. 4Abbreviations: MS. mass spectrometry; CI. chemical ionization. Estimates of the quantity of sesbanimide in seed extracts were 5Finnigan MAT 4535fTSQ. 355 River Oaks Parkway. San Jose. CA 95134. The mention of ftrm names or trade products does not imply that they obtained by comparison of m/z 139 ion intensities, in are endorsed or recommended by the U.S. Dep. Agric. over other firms or daughter spectra of mlz 310, to the mlz 139 ion intensity similar products not mentioned. obtained in like manner from 100 ng of pure sesbanimide. Volume 38. Issue 2 (March) 1990 149 POWELL ET AL.: SESBANIMlDE IN SEEDS OF SESBANIA Table 1. Occurrence of sesbanimide in seed of Sesbania species. Table 2. Toxicity of defatted ethanol exuacts of Sesbania seed and purified sesbanimide Aa. Species Sesbanimidea Accession no.bOrigin Species Survivors/tested' (~g/g of seed) S. bispinosa (Jacq.) W. F. (rng/kg/day) Wight n.d. PR43532 India Drummond rattlebush 400 0f3 Drummond rattlebush 200 Of3 S. drummondii (Rydb.) 100 3f3 Cory 10. 52 NU40670 Texas S. emenJ.S 400 6/6 S. emerus (Aubl.) Urb. n.d. NU49341 Mexico 200 6/6 100 6/6 Hemp sesbania S. e:wlrara (Raf.) Rydb. n.d. NU42422 Mexico Hemp sesbania 400 6/6 200 6/6 S. exaltata (Raf.) Rydb. n.d. NU54761 Commercial 100 6/6 S. grand/flora (L.) Pers. n.d. PR48413 Thailand S. grandiflora 200 6/6 Rattlebush 100 6/6 S. punicea (Cav.) Benth. 100. 90 NU53275 Georgia 50 6/6 (L.) NU42624 S. sesban Merr. n.d. Pakislall Rattlebush 100 0/6 S. sonorae Rydb. n.d. P116563 Arizona 66 1/6 P1321747 S. spec/osa Taub. n.d. Pakislall 44 5/6 Bagpod sesbania 29 6/6 S. ves/caria (Jacq.) Ell. 30. 18 NU25380 Texas S. sesban 300 5/6 2As determined by MS/MS; n.d. =not detected at the 0.1 ~g/g level (the 200 6/6 lower limit ofdetection). The first value reponed was obtained on a sample that 133 5/6 was stored at -10 C for 2 yr; the second value reponed is a mean obtained on Bagpod sesbaniad 100 0/6 freshly prepared samples obtained from the same seed lot. The method does not 66 1/6 distinguish isomers such as sesbanimides A and B. Coefficient of variation for 44 6/6 replicate determinations on freshly prepared samples was 11 % (n = 3). Sesbanimide A 0.12 0/6 bAccession numbers referenced to the seed collection at the North. 0.06 1/6 Regional Res. Ctr.. Peoria. IL. 0.03 6/6 aData obtained from a.TJ.titumor tests (P-388 letL1<emia in mice) conducted under conuact according to Nat Cai1cer Inst.
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