Rotenone Content Research Articles

Spatiotemporal visualization of the synthesis and accumulation of rotenone in Derris elliptica roots using mass spectrometry imaging

The discovery of novel botanical pesticides as a preferred alternative to synthetic pesticides is regarded as an environmentally friendly strategy, yet it remains a great challenge due to limited insights into the synthesis and accumulation of active ingredient intermediates. Herein, we demonstrate the use of gold nanoparticle (AuNP)-assisted laser desorption/ionization mass spectrometry imaging (LDI-MSI) for the tissue-specific distribution and spatiotemporal accumulation effect of rotenone and active ingredient intermediates in its biosynthetic pathway within the roots of Derris elliptica. The MSI results revealed that rotenone was mainly concentrated in the epidermis, cortex, and xylem in the first two years and began to accumulate in the phloem since the 3rd year. Meanwhile, the rotenone contents increased in the epidermis, cortex, and xylem in the 4th year and finally decreased in the 5th year. The ultra-performance liquid chromatography (UPLC) results revealed that there was a significant difference in rotenone content between the root and non-root bark (p < 0.05) except for the 1st year. It reached its maximum value at 9.71% in the root bark in the 4th year and 7.98% in the non-root bark in the 1st year, which was in accordance with the MSI results. Additionally, the active ingredient intermediates in the Hydroxylation/Methylation and Rotenoid Phases of the biosynthetic pathway of rotenone were concentrated in the root region. Taken together, the collective results provide the scientific guidance for the scientific cultivation of D. elliptica and the efficient extraction of botanical pesticides.

Pharmacognostic Specification and Rotenone Content in Derris elliptica Stems

Pharmacognostic Specification and Rotenone Content in Derris elliptica Stems

A Poisoning Outbreak Caused by Millettia Pachycarpa - Chongqing Municipality, December 2020.

What is already known about this topic? Millettia pachycarpa belongs to the Fabaceae family and is widely distributed in the southern China. It is toxic for the rotenone contained in its roots and seeds, and ingesting its seeds could result in poisoning. What is added by this report? In December, 2020, a poisoning from plant seeds occurred in Chongqing Municipality. The etiological association was confirmed based on epidemiological investigation, clinical manifestation, plant species identification, and rotenone analysis. The patient rapidly developed central nervous and respiratory depression with metabolic acidosis. The plant was identified as Millettia pachycarpa, and toxin analysis indicated that the rotenone content contained in the seeds was high enough to cause intoxication. What are the implications for public health practice? Millettia pachycarpa poisoning is rare but could be fatal. Efforts should be made to educate and communicate with the public, doctors, and public health practitioners that the toxic effects the seeds could be life-threating when swallowed, both accidentally or intentionally.

Toxicities comparison of rotenone and acetone extract of Tephrosiavogelii and Derris trifoliate against Solenopsis invicta

The high rotenone content and the rotenone crude extract of Tephrosia vogelii and Derris trifoliata were evaluated for its efficacy in the control of red imported fire (RIFA), Solenopsis invicta under both laboratory and field conditions. The acetone extracts of D. trifoliata roots and T. vogelii leaves exhibited strong toxicity to macroergate and micrergate of RIFA. When active ingredients of the crude extracts were convert to rotenone, the activity of the acetone extracts were higher than that of rotenone technical material. At the same time, the extracts showed significant inhibitory effect on walking ability and grasping ability of worker ants and stronger than the effect of 98.6% rotenone technical material. Under field conditions, the 0.01% rotenone-bait, formulated with the acetone extract of D. trifoliata roots and T. vogelii leaves, had the same control effect on RIFA as that of 0.01% fipronil-bait when treated after 30 d. The bait formulated with the extract of D. trifoliata exhibited quicker and higher effect on RIFA than that of rotenone technical material. It was showed that the acetone extracts of D. trifoliata roots and T. vogelii leaves are able to control S. invicta under both laboratory and field conditions and can be used as an effective agent against RIFA.

A PRELIMINARY STUDY ON MOSQUITO LARVICIDAL EFFICACY OF ROTENONE EXTRACTED FROM MALAYSIA Derris sp.

Rotenone is a bio-active compound extracted from Derris elliptica (locally known as ‘Tuba’ plant). It has long been used as bio-pesticide, which is more environmental friendly than the commercially available pesticides and has the potential to be used in eliminating mosquito larvae. Therefore, the objective of this study is to determine the mosquito larvicidal activity (LC50) through the usage of liquid crude extract of Derris plant root. The rotenone liquid crude extract was extracted using normal soaking extraction (NSE) method. Two different solvent ratios were used to extract rotenone namely: (A) methyl chloride: methanol (1:1) and (B) methyl chloride: methanol (1:9). The extracts were concentrated using rotary evaporator at 40 oC with vacuum pressure of 800 mbar prior to the reverse-phase high performance liquid chromatography analysis (RP-HPLC) and biological activity (LC50) study. Next, the diluted extracts were subjected to the biological activity treatment for 6 hrs. The results showed that the concentrated liquid crude extracts of methyl chloride: methanol (1:1) which contained the highest rotenone content produced the lowest treatment concentration of 0.024 mg/ml to achieve 50% mortality within 3 hrs of treatment (p&lt;0.05). The rapid mortality (as indicated by the LC50 value) of the mosquitoes’ larvae against rotenone extracted from Derris plant roots has proven that it has the potential to be used as larvicide to control vector-borne diseases especially from mosquitoes.

Development of a New Binary Solvent System Using Ionic Liquids as Additives to Improve Rotenone Extraction Yield from MalaysiaDerrissp.

Rotenone is one of the prominent insecticidal isoflavonoid compounds which can be isolated from the extract ofDerrissp. plant. Despite being an effective compound in exterminating pests in a minute concentration, procuring a significant amount of rotenone in the extracts for commercialized biopesticides purposes is a challenge to be attained. Therefore, the objective of this study was to determine the best ionic liquid (IL) which gives the highest yield of rotenone. The normal soaking extraction (NSE) method was carried out for 24 hrs using five different types of binary solvent systems comprising a combination of acetone and five respective ionic liquids (ILs) of (1) [BMIM] Cl; (2) [BMIM] OAc; (3) [BMIM] NTf2; (4) [BMIM] OTf; and (5) [BMPy] Cl. Next, the yield of rotenone, % (w/w), and its concentration (mg/mL) in dried roots were quantitatively determined by means of RP-HPLC and TLC. The results showed that a binary solvent system of [BMIM] OTf + acetone was the best solvent system combination as compared to other solvent systems (P&lt;0.05). It contributed to the highest rotenone content of 2.69 ± 0.21% (w/w) (4.04 ± 0.34 mg/mL) at 14 hrs of exhaustive extraction time. In conclusion, a combination of the ILs with a selective organic solvent has been proven to increase a significant amount of bioactive constituents in the phytochemical extraction process.

English

Bio-pesticides are becoming increasingly important as pest management tools in various cropping systems in the tropics essentially to remedy problems associated with the indiscriminate use of 'hard' and non-environmental friendly inorganic pesticide. In these past few decades, many bio-pesticidal products, both microbial-based (bacteria, fungi, microsprodia, entomopathogenic nematodes and viruses) and plant-based botanicals (rotenone and azadiracthin) have been studied for their use against insect pests in the tropics. In this study, the effects of the concentration process with respect to the yield of rotenone (mg) and its concentration (mg/mL) are presented extensively. The raw plants were collected from Kota Johor Lama, Johor and sorted to obtain the roots and stems. Only the roots and stems were utilized as raw materials of the extraction process. The rotenone from roots and stems was extracted using the normal soaking extraction (NSE) at 28 to 30 degrees C with 95% (v/v) of acetone as a solvent and the solvent-to-solid ratio of 10 mL/g. The extraction was carried out for 24 h. Next, the liquid crude extract was concentrated using the rotary evaporator at 50 degrees C and 80 mbar of vacuum pressure to remove approximately 90% of solvent. The fractions of the liquid crude extract were collected (15 min/mL/fraction), diluted (1/100 with acetone) and cleaned up (to remove any fine debris) prior to determination of rotenone content (mg) and concentration (mg/mL) by using the reverse-phase high performance liquid chromatography (RP-HPLC). Finally, the results showed that there was a significant effect of thermal degradation or dissipation of rotenone content at higher operating temperature (greater than 40 degrees C) with a rapid rotenone reduction for the first 15 min of exposure. The possibilities for better exploitation and identification of the effective operating parameters based on the above mentioned results will be perhaps discussed in the future.

Oviposition deterrent activities of Pachyrhizus erosus seed extract and other natural products on Plutella xylostella (Lepidoptera: Plutellidae).

An extract of a rotenone-containing plant yam bean, Pachyrhizus erosus (L.) Urban, seeds was tested against the diamondback moth, Plutella xylostella (L.) in a greenhouse to determine its potential as an oviposition deterrent and compared with coumarin and rutin, known as diamondback moth oviposition deterrent compounds, rotenone, and an extract of Peruvian cube root, at a concentration of 0.5% (w/v). Oviposition deterrent index (ODI) was used to determine effects of extracts or compounds in inhibiting oviposition of diamondback moth. Coumarin showed a stronger deterrent effect than the yam bean seed extract with a higher ODI value. On the contrary, rotenone, rutin, and the cube root extract, containing 6.7% (w/w) of rotenone, showed no significant deterrent effects having low or negative ODI values, suggesting that the deterrent effect of the yam bean seed extract is not due to rotenone content of the yam bean seeds. The extract of yam bean seed and coumarin partially deterred the moth from laying eggs on treated leaves in a concentration-dependent manner. The effective concentration for 50% deterrency of coumarin and the yam bean seed extract were 0.11 and 0.83% (w/v), respectively. However, the yam bean seed extract showed a residual deterrent effect on the moth even at 3 d after the treatment and is probably because of its low volatile nature. A long-term deterrency of the yam bean seed extract is an advantage over coumarins. Both the yam bean seed extract and coumarin deterred diamondback moth from laying eggs in total darkness, indicating their nonvisual deterrent effect. This made the extract an effective deterrence to diamondback moth in light and in darkness. To conclude, this study revealed the potential of the crude extract of the yam bean seed to prevent diamondback moth from ovipositing on its plant host.

Ichthyotoxicity and Rotenone Stability of Derris trifoliata (Leguminosae) Acetone Formulations

The stability of the acetone extract of Derris trifoliata (as a more accessible piscicide for fishpond management) was compared with those of Derris elliptica (Leguminosae) for a duration of seven months with respect to toxicity and rotenone content to Oreochromis niloticus (Cichlidae). Extract formulation of D. elliptica was found to retain its fish toxicity throughout the duration of the experiment without exposure to sunlight while that of D. trifoliata was found to decrease after only about a month. The toxicity of D. trifoliata and D. elliptica formulations were maintained longer, when their extracts were refrigerated at around 9 – 10o C. Chromatographic analysis (HPLC) revealed that although fish toxicity is maintained, rotenone concentration continued to decrease in D. elliptica extracts much faster at conditions where the extracts were exposed to sunlight than if kept in a refrigerator or simply kept inside a room at ambient conditions. However, for the D. trifoliata extract, not much difference was found if it was kept exposed or not to sunlight, as the rotenone concentration in both conditions continued to drop. Placing the extract at 9 – 10o C in a refrigerator prevented this rapid degradation of rotenone. A better way of preventing the toxicity to decrease and the rotenone to degrade was by partitioning the acetone extract between chloroform and water, taking the chloroform extract, evaporating, collecting and reformulating it when needed. This new formulation showed better rotenone stability and consistent toxicity throughout the seven months of experimental observation.

Extraction of rotenone from Derris elliptica and Derris malaccensis by pressurized liquid extraction compared with maceration

The extraction of active compounds from plants is one of the most critical steps in the commercial development of natural products for medicinal, herbicidal or pesticidal use. The focus of this study was to compare conventional maceration and pressurized liquid extraction (PLE) techniques for the efficient extraction of rotenone from the stem and root of Derris elliptica Benth and Derris malaccensis Prain. The effects of experimental variables, such as solvent, temperature and pressure, on PLE efficiency have been studied. Chloroform was determined to be a good extraction solvent (rotenone content 40.6%, w/w) compared to commonly used solvent, 95% ethanol (rotenone content 15.0%, w/w). The optimal conditions for PLE were 50 °C and 2000 psi. PLE showed higher extraction efficiency (rotenone content 46.1%, w/w) as compared with conventional maceration method (rotenone content 40.6%, w/w). The order of rotenone content found in crude extract obtained by optimized method from the highest to the lowest was root (46.1%, w/w) and stem (9.4%, w/w) of D. elliptica and stem of D. malaccensis (5.2%, w/w), respectively. Moreover, the results from this study indicated that PLE was considerably less time and solvent consuming (30 min, 3 ml/g of dried sample) than the conventional maceration techniques (72 h, 10 ml/g of dried sample).

Use of Derris trifoliata (Leguminosae) Root Extracts for Fishpond Management

This study aims to determine whether Derris trifoliata (Leguminosae) locally known as “sila-sila”, can be used in a formulation for fishpond management, compared with the usual commercial source “tubli” (Derris elliptica, Leguminosae). Thus, prior to the formulation of the root extracts, the rotenone content of the roots of Derris trifoliata was determined and compared to two other Derris species, one of which is Derris elliptica. Of the three derris species, D. trifoliata was found to have the lowest rotenone content of 0.019% compared to that of Derris elliptica’s 5.09%. Although D. trifoliata has very low rotenone content, the extract of its root bark and formulation with acetone resulted in 1 L formulations with comparable toxicity as that of D. elliptica or that of a commercial insecticide (illegally used as piscicide). For example, formulations from about 15 kg of root or root bark and 20 L of acetone as extractant produced formulations of about 10 x 1 L for D. trifoliata (rotenone conc. = 0.180 mg•ml-1) and 12 x 1 L for D. elliptica (rotenone conc. = 4.90 mg•ml-1). Both formulations can kill fish such as Oreochromis niloticus (Cichlidae) fingerlings within 30 minutes comparable to a commercial insecticide Telothion 40. The median lethal concentration of the formulation for a 96-hour bioassay against O. niloticus for D. trifoliata was LC50 = 0.03 ppt while for D. elliptica, LC50 = 0.005 ppt. Sensitivity of nine different unwanted fishes near the location of the test fishponds was determined using a D. trifoliata reconstituted formulation. The unwanted fishes appeared more sensitive during summer months when the salinity of water was higher than during the rainy months when the salinity was much lower. Different species of unwanted fishes at different life stages appeared to have different tolerance to the toxicity of the extract. Application of the different formulations previously bioassayed was successful in cleaning several fishponds from unwanted fishes. Cost analysis showed that fish farmers (whose fishponds are located near colonies of D. trifoliata plants) could economize by using extracts of this Derris plant instead of insecticides harmful to the environment or dangerous poisons like sodium cyanide.

Rotenone and rotenoids in cubè resins, formulations, and residues on olives.

Rotenone and rotenoids (deguelin, beta-rotenolone (12a beta-hydroxyrotenone), tephrosin (12a beta-hydroxydeguelin), 12a alpha-hydroxyrotenone, and dehydrorotenone) were determined in cubè resins and formulations. Cubè resins from Lonchocarpus contain large quantities of deguelin (ca. 21.2%) and smaller quantities of tephrosin (ca. 3.5%) and beta-rotenolone (ca. 3.0%). The composition of commercial formulations may present very different rotenoid contents depending on the extracts used to prepare them. Because these rotenoids also present insecticide activity, the efficacy of these formulations may be very different. The storage stability and photodegradation of some rotenone formulations were studied. Rotenone and rotenoids are very sensitive to solar radiation, which degrades them rapidly, with half-lives in the order of a few tens of minutes. Some formulations show greater disappearance rates than that of cubè resin, indicating that not much attention has been paid to protecting the active ingredients from photodegradation in the formulation. A study on the residues on olives was also carried out to assess not only the rotenone content, but also that of the main rotenoids. At harvest, the residues of deguelin, tephrosin, and beta-rotenolone were 0.10, 0.06, and 0.10 mg/kg, respectively, very similar to rotenone (0.08 mg/kg), and though a few data indicate similar acute toxicity values for deguelin, only rotenone is taken into consideration in the legal determination of the residue.

Rotenone: Efficiency against Olive Fly (Bactrocera oleae Gmelin) and Residual Activity in Olive Oil

ABSTRACT Rotenone solution (root extract of Derris elliptica; 10% or 20% a.i.) was tested as a bait with 2% hydrolysate protein in field trials to determine its efficiency against olive fly (Bactrocera oleae Gmelin). Olive trees cvs. Koroneiki and Tsounati located in the Nerokorou District of Chania, Crete were sprayed. Rotenone toxicity was tested against both adult and immature stages of olive fly in laboratory trials. A notable repellent action of the high concentration of rotenone solution was found while no selective activity of rotenone was observed between the two olive fly sexes. Duration of insect contact with the sprayed surface was crucial for the effectiveness of rotenone. Residues of both 10% and 20% rotenone solutions were monitored in olive oil extracted from fruit harvested immediately, and 4, 8 and 25 days after spraying. The rate of rotenone degradation was linear and fast in both treatments, depending on doses. Residue in olive oil was also monitored during storage in a tank in the dark at 20–26°C for 5 months followed by storage in transparent glass bottles in darkness or light at 20–26°C or darkness at −20°C for 3 more months. Monitoring of the residual activity in olive oil during storage (December 1996-August 1997) showed that light plays a dominant role in rotenone degradation. Rotenone residues were relatively stable in the dark at both temperatures. The rate of degradation after a period of 8 months was very slow (16%). However, olive oil samples stored for 5 months in the dark, followed by a three-month storage in the light showed a 44% decline in rotenone content.

Analysis of Rotenone in Cube and Derris Root Powders and Formulations by Liquid Chromatography

Abstract A modified liquid chromatographic (LC) procedure, including an improved extraction, has been developed to analyze rotenone in root powders of derris and cube. The procedure is also applicable to formulations. Samples are sonicated for 5 min in chloroform or a mixed solvent of tetrahydrofuran-acetonitrile-water-glacial acetic acid, followed by liquid chromatography. Rotenone content of 4 lots of root powder samples showed good agreement between the new extraction and the AOAC official extraction; coefficients of variation ranged from 5 to 1.2%. Five formulations were also analyzed and showed good agreement with results for methanol extraction. Coefficients of variation were 4.5% or less. Purity of the rotenone peaks was tested by using a photodiode array detector in the spectrum and UV ratio modes. It is recommended that the new method be tested collaboratively.

Rotenoids of Lonchocarpus salvadorensis: Their effectiveness in protecting seeds against bruchid predation

Seeds of the legume Lonchocarpus salvadorensis, having unusually low bruchid predation, contain deguelin (0.29%) rotenone (0.22%), elliptone (0.06%) and α-toxicarol (0.003%). The relation between rotenone content and toxicity towards the generalist bruchid Callosobruchus maculatus is examined and quantified.

Recovery of natural insecticides fromtephrosia vogelii. iii. an improved procedure for sampling and assaying rotenoid content in leaves

Recent studies have shown Tephrosia vogelii Hook. f. to be a promising source of rotenone. It could conceivably give the United States a dependable domestic source of this natural insecticide. The roots of Derris and Lonchocarpus comprise the only present commercial source of rotenone. Tephrosia vogelii, on the other hand, produces its highest rotenoid content in the leaves (5). Though T. vogelii is a tropical plant, it has yielded well when grown as an annual in the southern United States and should lend itself to harvest by mechanical methods. Irvine and Freyre (6) reported that differences in total rotenoid content varied significantly among introductions of T. vogelii. A breeding and selection program was undertaken at the Federal Experiment Station in Mayaguez, Puerto Rico, to increase the rotenone content in the leaves. New techniques for assaying rotenoid content had to be devised because the established procedures previously used for root samples of Derris and Lonchocarpus were inadequate. The most commonly used assay procedure for quantitatively estimating rotenone and related compounds in these root crops has been the red-color test described by Gross and Smith (4), modified by Goodhue (3) and further refined by Jones (7). The method adapted for the early work with T. vogelii was described by Irvine and Freyre (5, 6) as briefly consisting of collecting the median pair of leaflets from each leaf of the plant,

Seleção e melhoramento do timbó: II - Estudo de uma população de 153 plantas de timbó macaquinho - Derris nicou (benth.)

Para fins de seleção foi estudada, no Instituto Agronômico do Norte, uma população de 153 plantas de timbó macaquinho - Derris nicou (Benth.). Depois de colhidas as raízes e postas a secar ao ar, foram analisadas para determinação de umidade, cinzas, extratos totais (etéreo e por gravimetria), rotenona + deguelina (por colorimetria) e rotenona (por gravimetria). Pelo estudo dos dados pôde-se verificar que havia dois grupos distintos de plantas: um constituído por 82 plantas (POPULAÇÃO A) contendo menos de 5% de rotenona nas raízes e outro, com 71 plantas (POPULAÇÃO B), com 9% ou mais de rotenona em suas raízes. Essas populações foram estudadas separadamente. Para um estudo mais detalhado dêsses grupos de plantas também foram calculados o peso líquido das raízes, bem como o rendimento líquido, por planta e em média, em extratos totais, rotenona + deguelina e rotenona. Foram também calculados os teores em deguelina e rotenona contidos nos extratos totais e outros extratos (que não rotenona e deguelina) contidos nos extratos totais e, finalmente, a rotenona contida no conjunto rotenona + deguelina. São apresentados os resultados referentes às melhores plantas selecionadas dessa população. Vários fatôres foram levados em consideração para a separação dessas plantas, tidas como os melhores. Os resultados mostram que mediante adequada multiplicação do material selecionado será possível a instalação de culturas de timbó com elevado rendimento em rotenona.

Reversal of Genetic Dwarfism in Tephrosia vogelii by Gibberellin

IN conjunction with a breeding programme designed to produce plants of Tephrosia vogelii Hook f. with a higher rotenone content, multiple crosses were made between two lines of similar morphology, but of separate geographical origin. Nine dwarf plants were obtained as segregants in an F 2 population of 103 individuals. These dwarfs were characterized by greatly reduced internodes, hypocotyls, petioles, and rachises. Leaflets were also much smaller, and leaf colour was a darker green than normal. The number of leaves per plant, the number of leaflets on corresponding leaves, and the size and colour of the cotyledons were unaffected.

Determination of rotenone in Lonchocarpus root and oleo‐resin

AbstractThe rotenone content of Lonchocarpus root and of the oleo‐resin have been determined by a standard method of direct crystallisation of the carbon tetrachloride solvate and also by the crystallisation of the solvate after the partial removal of other components by alkali extraction or column chromatography. The highest results were given by the chromatographic method and the lowest by the direct crystallisation procedure. Evidence is presented that direct crystallisation gives results that may be 20% lower than the true values, and revision of the standard method is desirable.

Seleção e melhoramento do timbó: I - Estudo de uma população de 235 plantas de timbó urucu (Derris urucu (killip &amp; smith)

Para fina de seleção foi estudada uma população constituída por 235 plantas de Timbó urucu - Derris urucu, plantada primitivamente no Hôrto "Cipriano Santos", na cidade de Belém, Pá. Colheram-se suas raízes que, após secagem ao ar, foram pesadas e analisadas para determinação de umidade, cinzas, extratos totais, rotenona e deguelina. Todos os dados individuais obtidos são apresentados, bem como os resultados de sua análise estatística. Também foram calculados o pêso líquido das raízes, bem como o rendimento líquido, por planta e em média, em extratos totais, rotenona + deguelina e rotenona. Calcularam-se, também, os teores em deguelina e outros extratos, e rotenona contida nos extratos totais, deguelina contida nos extratos totais, e outros extratos (que não rotenona e deguelina) contidos nos extratos totais e, finalmente, a rotenona contida no conjunto rotenona + deguelina. Dentre as 235 plantas estudadas foram escolhidas doze, com riqueza em rotenona variando de 8,7 a 11,2%, das quais colheram-se as raízes após 19 meses de plantio. Determinou-se o rendimento em raízes sêcas ao ar bem como a umidade contida nas raízes e, depois, sua riqueza em extratos totais e rotenona (determinada por dois métodos: cristalização e solvato). Tais seleções produziram, em média, 1717 gramas de raízes sêcas ao ar, por planta, com teor em extratos totais que variou de 17,2 a 33,2%, com média de 23,6%. A riqueza em rotenona (média dos resultados obtidos pelos dois diferentes métodos de determinação)