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Wood preservation is carried out to increase the service life of wood with low natural durability. Factors such as wood structure, preservatives, and methods of preservation influence the preservation processes. The aim of this study was to evaluate retention, penetration, and distribution of tuba (Derris elliptica) leaves extract into the candlenut wood (Aleurites molluccana) and agathis (Agathis sp.) wood structures. The wood samples were treated with hot and cold soaking. The duration of hot soaking were 3, 5, and 7 hours, while for cold soaking were 3, 5, and 7 days. The result showed that the highest retention of extract was achieved by cold soaking for 7 days at 9.4 kg m-3, and the lowest retention was achieved by hot soaking for 3 hours at 1.9 kg m‑3. The highest penetration occured by cold soaking for 7 days at 8.08 mm and the lowest was that with hot soaking for 3 hours at 2.81 mm. However, the distribution of the extract in the agathis wood structures could not be detected by stereo microscope. In the the case of the candlenut wood, the extract was distributed in the parenchyma cell.

[THE INFLUENCE OF BOTANICAL INSECTICIDES BASED ON CROTON OIL AND DERRIS ROOT AGAINST BROWN PLANTHOPPER]. Brown planthopper (BPH) (Nilaparvata lugens Stall) is a serious pest in rice. Using synthetic insecticide to control BPH is harmful for human health and can caused environmental pollution. The objective of this research is to find out ecofriendly insecticide to control BPH. Research has been conducted at Entomological laboratory, Indonesian Spice and Medicinal Crops Research Institute (ISMECRI), Bogor. It was designed with CRD, 16 treatments and 3 replications. Treatments consisted of botanical insecticides based on Croton tiglium and Derris elliptica. Each material was extracted by water, methanol, and xylene, and then tested by individually and combination, so there were 15 formulas and 1 control treatment (water). Third nymph BPH and IR64 rice variety were used in this research. Research was done in two methods, i.e. contact application and residual application. The result shows that there are 11 formulas which are prospective to be further developed i.e aqueous extraction (6 formulas) and combination extraction (aqueous with xylene and methanol (5 formulas). The aqueous extraction maybe the most prospective formulation since the technique could easily be adopted by farmers. Botanical pesticide based on Croton tiglium and Derris elliptica are very promising, therefore the research should be continued to find out the best formula of botanical insecticides for controlling BPH).

Derris elliptica (Wall.) Benth. is one of the wild plants found in farmland of Southeast Asia. The root of the tuba plant was traditionally used as the fish poison and crop pest insecticide. It has many kinds of toxic chemical compounds as rotenone, toxicarol, elliptone, sumatrol, tephrosin, and deguelin. Recently, root extract has developed in various bioactive compounds exploration not only for the agricultural field but also public health intervention, especially in Dengue control programs. Derris elliptica (Wall.) Benth. root extract have larvacidal potential to control the temephos-resistant Aedes aegypti larvae.

Application of extract tuba root bioactive (Derris elliptica L.) as a natural insecticide on the Crocidolomiabinotalis caterpillar on mustard plants ( Brassica juncea L.) has been carried out. The test results indicate that there are differences in antifeedant activity of the Crocidolomiabinotalis caterpillar on mustard plants ( Brassicajuncea L.) which is significant (significant) at various levels of concentration. The research was carried out in several stages, starting from the tubal root extraction stage, phytochemical testing, preparation of caterpillar tests, testing of antifeedant activity. As the treatment is the level of methanol concentration of 50 ppm, 100 ppm, 500 ppm and 1000 ppm. The parameter observed was the percentage of Feeding Reduction (FR). The test results showed the antifeedant activity of Crocidolom he binotalis caterpillars, which is best at concentrations of 500 ppm and 1000 ppm because it is able to inhibit the feeding power or Feeding R eduction of caterpillars test 30.16% and 44.00 %

Brown planthopper (Nilaparvata lugens Stal.) is one of rice plants' pests that attack from the nursery to the harvest stage. Controls carried out by farmers generally use synthetic insecticides. Reducing the impact caused by synthetic insecticides, an alternative that can be used to controlling the brown planthopper is by using botanical insecticide tuba root. Tuba root plants have been widely reported to control pests and contain the active ingredient rotenone. Rotenone works as a stomach poison and selective. This study aims to examine the ability of tuba root plant parts extracts (leaves, branches, and roots) with organic solvents to control brown planthopper pests in rice plants. The study was conducted in February-April 2019 at the Plant Pest Laboratory, Faculty of Agriculture, University of Riau. The study was conducted experimentally using a Completely Randomized Design (CRD) with three treatments and six replications to obtain 18 experimental units. The tuba root plant trial test consists of 3 levels: root extract, branch extract, and leaf extract with organic solvents. The parameters observed were the time of death of brown planthopper (hour), lethal meantime (LT50) (hour), daily mortality (%), and total mortality (%). The results showed that the application of root extract caused an initial death of 2.33 hours after application, LT50 17.33 hours after application with a total mortality rate of 100%. Application of botanical insecticide tuba root is effective for controlling brown planthopper pests in rice plants because it causes the death of brown planthopper above 80%.

The research purposed was compared of two extracts as molluscicidal activities from root of Derris elliptica Wallich. and Pangium edule Reinw seed, that assessed to 3-month old snails Pomacea canaliculata L. The Golden apple snails is widely regarded as worst invasive pest species in the rice growing area. It normally destroys the young stems and leaves paddy and could consume 7 – 24 rice seedlings per day. The experiment research started with the mortality test of the golden apple snail, meanwhile hexane extract fraction and etanol extract fraction have completely jumble mode; using the lethal concentration (LC) have mean to describe short term potency of poisonous (toxicity) from materials and can gave little effect or impact for environment; processing phytochemical test from n-hexane extract and etanol extract of root D.elliptica and P.edule showed positive to contain tanin, saponin and fenol. The data of LC 50 from n-hexane fraction measure with probit analyze (9,905 mg L -1 ) by D.elliptica L . with high toxic category, and n-hexane fraction (11,574 mg L -1 ) by P.edule Reinw. with toxic category are more effective for golden apple snail control. The golden apple snail mortality was highest using 5000 ppm n-hexane fraction showed 93,3% from D.elliptica and using 5000 ppm n-hexane fraction from P.edule showed 63,3%. In conclusion, both of extracts from D.elliptica roots and P.edule seeds was showed potency as botanical mollusicicides and it can be apply in the field

Promoting the organic farming, much of the plant extracts used for controlling pests and fungi have been imported from China, India and Myanmar. But, it is so worrisome that aquatic animals such as muddy loach inhabiting in paddy field and common carps in river exposed to the pests and fungi likely be harmed. This study was conducted in order to evaluate the risks of aquatic animals influenced by the three plant extracts, i.e. Sophora flavescens, Azadirachta indica and Derris elliptica. The toxicities of common carp (Cyprinus Carpio), muddy loach (Misgurnus anguillicaudatus) and PEC (Predicted environmental concentration) exposed to the three plant extracts were estimated by the typical spray volume method. Risks were determined by the toxicity value as 48-hr LC50 (Lethal concentration, median) or NOEC (No observed effect concentration) into PEC. 48-hr LC 50 of Common carp and NOEC by Sophora flavescens extracts was 7.9 and 6.2 mg/L, 26.8 and 21.8 mg/L by Azadirachta indica extracts and 47.0 and < 24.0 mg/L by Derris elliptica extracts, respectively. 48-hr LC50 of Muddy loach and NOEC by Sophora flavescens extracts was 16.9 and 10.0 mg/L, 35.6 and 30.0 mg/L by Azadirachta indica extracts, and 73.9 and < 40 mg/L by Derris elliptica extracts, respectively. Therefore, acute toxicities of the three plant extracts for aquatic animals were proved to be very low level. PEC of Sophora flavescens extracts in paddy, drainage and river water was 68.0~3.0, 11.33~0.50 and 3.0~0.0018 mg/L, respectively. TER of Sophora flavescens extracts in the three water was 0.2~5.6, 1.5~33.8 and 2.6~4388.9, respectively. PEC of Azadirachta indica extracts in paddy, drainage and river water was 90.9~1.2, 15.2~0.2 and 4.8~0.00075 mg/L, respectively. TER of Azadirachta indica extracts in the three water was 0.4~29.7, 2.3~178.0 and 4.5~35733.3, respectively. PEC of Derris elliptica extracts in river water was 0.0063 mg/L. TER of Derris elliptica extracts in river water was 5222~15667.

Chili ( Capsicum annnum L.) is one of the horticultural commodities that has economic value. The aim of the research was to determine the effect of root extract of tubal ( Derris elliptica ) on various concentration levels to control Trips pavispinnus in red chili plants. The treatment tried is three extra concentrations of the tubal root; 10, 20, and 30 g of tubal root / water and one treatment without tubal roots as a control. The treatment was designed using a randomized block design with three replications. Rensposes observed were percentages of Trips pavispinnus mortality. The results showed that the extract of the root of the tuba can control the pest of Trips pavispinnus. The concentration of 10 g / L of water can kill the Trips pavispinnus to 74.42% on the day after application. To be able to prevent the loss of red chilli plants due to a series of Trips pavispinnus , farmers can take advantage of extracts from the root of the tube, and are an environmentally friendly pest control method. Keywords: Chili, Derris elliptica , Tuba root, Trips pavispinnus

Pests that attack the corn crop are cob borers (Helicoverpa armigera Hubner). The pest control can be done using tubal root botanical insecticide (Derris elliptica Benth.). This study aims to obtain the best concentration of tuba root powder extract in controlling the corn cob borer pests H. armigera. Research has been carried out at the Plant Pest Laboratory of Agriculture Faculty, University of Riau. This study used a completely randomized design (CRD) with 6 treatments and 4 replications. The treatments given were several concentrations of tuba root powder extract, namely 0 gr.l−1 of water, 20 gr.l−1 of water, 40 gr.l−1 of water, 60 gr.l−1 of water, 80 gr.l−1 of water and 100 gr.l−1 of water. The parameters observed were initial death, lethal time 50, lethal concentration 50 and 95, daily mortality and total mortality. Daily mortality data obtained from the results of the study were analyzed descriptively and displayed in graphical form, data lethal concentration (LC50 and LC95) were probit analyzed using the POLO-PC program, while other data such as initial death, total mortality, lethal time (LT50), statistically analyzed using a variance. Data from analysis of variance will be continued using the smallest significant difference (LSD) test at the 5% level. The application concentration of tuba root extract with 100 g.l-1 of water is the best concentration to control larvae of H. armigera with an initial time of death 26.50 hours, 67.50 hours of LT50, highest daily mortality on the fourth day by 40% and total larval mortality by 87.5%.

Derris elliptica (Fabaceae) is one of the most important sources of the insecticide rotenone. This plant was first introduced from different Southeast Asian countries to China in the early decades of last century. The purpose of this study is to assess genetic diversity of D. elliptica in China for the conservation of its germplasm resources and for future breeding programs. Genetic diversity and population structure of 14 cultivated populations of D. elliptica in China were detected using 25 microsatellite markers. A moderate level of genetic diversity was found across the whole sample (expected heterozygosity, He = 0.529), indicating a history of multiple sources of introduction and a broad genetic base for the crop cultivated by cuttings. The genetic diversity at the population level (Mean He = 0.31) was relatively lower. Repeated bottlenecks or founder effects in its short cultivated history and also its vegetative reproduction mode may explain the results. FST (Wright F-statistic) values and AMOVA (analysis of the molecular variance) indicated large genetic differentiation among populations (FST = 0.461; 44.1%, AMOVA), while the cluster analysis showed that the collections belong to two major groups of genotypes. The initial difference in the introduced germplasm from the primary center of origin and the limited gene flows among populations may have played important roles in shaping the genetic variation pattern in D. elliptica of China.

The study was designed to evaluate the inhibitory effects of selected herbs on plant growth. Three insecticides containing plants (leaf of Azadirachta indica A. Juss var indica (AI), Nicotiana tabacum L. (NT), and root of Derris elliptica (Roxb.) (DE) were selected for various solvent extractions. Five extraction solvents: methanol, hexane, dichloromethane, butanol and aqueous were used in this study. The test method was lemna phytotoxicity assay which measured the inhibitory effect on duckweed, Lemna minor growth. This toxicity test proved to be a practical bioassay method because this method is simple, sensitive and cost effective. Butanol extracts of AI were shown to have more inhibition activity on duckweed growth than NT (% inhibition growth rate is 66.08, 27.08 respectively). Butanol extracts of AI had inhibitory effect (EC10) of 40.87 μg/ ml while dichloromethane extracts had EC10 of 131.72 μg/ ml. It could therefore be concluded that butanol extracts of AI showed the greatest inhibitory effects. The results from this study suggest that butanol extracts of AI were the most promising candidates for biological weed control and might be used as potential natural herbicides or as alternatives for the reduction of chemical herbicides. The study is worthy of further investigation since this could provide potential bioherbicide and may lead to the discovery of new effective and applicable bioherbicide.

Operationally simple, stereocontrolled semisyntheses of the anticancer rotenoids elliptone and 12aβ-hydroxyelliptone, isolated from Derris elliptica and Derris trifoliata, respectively, are described. Inspired by the work of Singhal, elliptone was prepared from rotenone via a dihydroxylation-oxidative cleavage, chemoselective Baeyer-Villiger oxidation, and acid-catalyzed elimination sequence. Elaboration of elliptone to 12aβ-hydroxyelliptone was achieved via a diastereoselective chromium-mediated Étard-like hydroxylation. The semisynthesis of elliptone constitutes an improvement over previous methods in terms of safety, scalability, and yield, while the first synthesis of 12aβ-hydroxyelliptone is also described.

Medicinal plants and the drugs derived from them constitute great economic and strategic value for the African continent. Most of the truly effective medicinal plants and drugs were kept secret by the practitioners and knowledge was handed down only to their descendants and favorite apprentices. African scientists started rather late to evaluate their traditional pharmacopoeias, by exploring the potentialities of the African medicinal plants used through the centuries. The rich flora of Africa of medicinal plants offers good raw material for the pharmaceutical industry, particularly as certain plants grow only in Africa. The fixed oils and fats are important products used pharmaceutically, industrially, and as foods. Several species of Macrocystis, Laminaria, and Fucus are numerous in African waters and algins can be prepared from them. The roots of Derris elliptica L. (Fam. Compositae) produce an important insecticide due to their rotenone content. Rutin from Ruta graveolens is used to treat varicose veins and in retinopathy of the eyes.

Derris elliptica (Wall.) Benth is a wild plant or weed in agricultural fields that was traditionally used for poisoning fish and plant pests. Several studies showed the low lethal concentration of Derris elliptica root extract to control the laboratory strain Aedes aegypti larvae. This study aimed to evaluate the effectiveness of Derris elliptica root extract against the temephos-resistant Aedes aegypti larvae from the Dengue endemic areas. This experimental study used post-test only control group design with five different concentrations of methanolic Derris elliptica root extract, namely 0.09%, 0.13%, 0.17%, 0.21%, and 0.25%, respectively. Twenty-five of F1 temephos-resistant of wild-caught Aedes aegypti larvae were subjected to each group of the five different concentrations, and two control groups with aquadest. The temephos-resistant strain of Aedes aegypti larvae was determined by bioassay test with temephos -0.02 ppm compound. Mortality rate and lethal concentration (LC50 and LC90) of the larvae were calculated after 24-h contact. Average of mortality rate in each concentration after 24-h contact with Derris elliptica root extract were 32.8%, 49.6%, 72.0%, 95.2%, and 100% with LC50 and LC90 were 1,600 and 2,040 ppm, respectively. The methanolic Derris elliptica root extract have larvacidal potential to control the temephos-resistant Aedes aegypti larvae. Further research to obtain secondary metabolites is needed.

Tuba (Derris elliptica) is one of the insecticide-producing plant which can reduce the pest population due to its active compound, rotenone (C23H2206). The rotenone is deposit in all parts of tuba plant, as such as roots, stems, and leaves. The aim of this research aims was to evaluate the effectiveness of tuba bark extract against subterranean termite Coptotermes sp. The powder of tuba bark extract with 40-60 mesh size macerated with the ethanol by solvent obtains the extract. The extract was made into varions concentration namely 0,5%, 1%, and 1,5%, and applied to the paper disc. There are two types of termite test in this study, namely toxicity test and respiratory test. The mortality of termite and the weight loss of the paper disc were used as indicators of extract activity. The result showed that the concentration of 1,5% indicated the highest mortality from both of two types of test. This study was similar for the lowest weight loss of sample which was also given by concentration 1,5%.

Derris elliptica (Fabaceae) is one of the most important sources of the insecticide rotenone. The present study was aimed at developing microsatellite markers and evaluating their potential for use in germplasm genetics. There were 37 microsatellite markers specific for D. elliptica developed from an AC-enriched genomic library using the Fast Isolation by AFLP of Sequences Containing repeats (FIASCO) method. All markers were polymorphic amongst 16 accessions of the cultivated D. elliptica and four accessions of wild relatives, providing evidence for cross-species transferability within the genus Derris. These markers amplified a total of 159 alleles with a range of 2–8 and an average of 4.3 per locus. The polymorphic information content (PIC) value across all loci was 0.53 with a range of 0.05–0.75. There was similar genetic variability within cultivated and wild accessions (both with average expected heterozygosity of 0.54). Cluster analysis clearly distinguished all wild relatives from each other and from the cultivated genotypes. These markers should be used for genetic diversity studies and breeding programs in D. elliptica.

A new coumaronochromone, 6,4'-dihydroxy-7,5' -dimethoxy-coumaronochromone (1), together with eleven known flavonoids (2-12) were isolated from the ethanol extract of the aerial part of Derris elliptica. Their structures were elucidated on the basis of spectroscopic analysis. Compounds 2, 4, 7, 8 and 9 exhibited moderate insecticidal activities against larvae of Aedes albopictus. All compounds showed strong cytotoxic activities against Spodoptera litura (SL) and Trichoplusia ni BTI-Tn-5B1-4 (Hi-5) cells comparison to positive control of rotenone.

Denaturing Gradient Gel Electrophoresis (DGGE) was used to study the impact of rhizobial inoculants on the rhizosphere bacterial communities of three medicinal legumes: Indigofera tinctoria, Pueraria mirifica and Derris elliptica Benth. Rhizosphere soils were collected from these legumes grown naturally in 11 provinces of Thailand. The host-specific rhizobial strains were inoculated to their hosts planted in the collected rhizosphere soils of each legume. Four months after planting, total bacterial communities DNA was extracted from the uninoculated rhizosphere soils and the inoculated rhizosphere soils. DGGE fingerprints of PCR-amplified 16S rDNA were obtained from the bacterial communities. PCR-DGGE analysis showed that the bacterial community structures in native rhizospheres of the three legumes were different from each other based on the generated dendrogram and Sorensen’s index. These results suggest that different plant species and soil characteristics synergically affected the rhizosphere bacterial communities. The bacterial diversity of I. tinctoria and P. mirifica native rhizospheres were significantly different from that of D. elliptica Benth. native rhizosphere. Our results also showed that the inoculants contributed to the slight changes in rhizosphere community structures. In comparison with each other, the plants appeared to have a much stronger influence on the bacterial communities rather than the inoculants. Hierarchical cluster analysis revealed that the community structure of the inoculated rhizosphere of D. elliptica Benth. was more divergent from those of inoculated rhizospheres of I. tinctoria and P. mirifica. The ribotype richness which indicates species diversity, was highest in I. tinctoria rhizosphere, followed by P. mirifica rhizosphere and D. elliptica Benth. rhizosphere, respectively.

The solubility, stability, and synergistic activity of mandarin oil, extracted from peels of Citrus reticulata Blanco, combined with rotenone (extracted from roots of Derris elliptica (Roxb.) Benth.) for use against citrus red mite, Panonychus citri (McGregor), were measured under laboratory conditions. Results showed that the solubility of rotenone in mandarin oil was 2.29% (W/W). A positive synergistic acaricidal activity against citrus red mite occurred at a 7:3 ratio of 50% lethal concentration (LC50) of rotenone to mandarin oil, with a synergistic coefficient of 403.71. At ambient conditions, a degradation rate of 71.99% over 14 days was found for rotenone in mandarin oil, which was markedly higher than the rate of 61.44% in benzene. Experiments on mandarin oil revealed a 2.48% extraction rate of rotenone in mandarin oil compared to an extraction rate of 1.47% in benzene solvent. When used against adult red mites, the mandarin oil rotenone extract had an LC50 of 0.88 mg/mL which is considera...

AIM: To study the chemical constituents of Derris elliptica (Roxb.) Benth. METHOD: The chemical constituents were isolated by various chromatographic methods, and the chemical structures were elucidated on the basis of spectral analysis. RESULTS: Seven rotenoids were obtained and their structures were identified as 7'-hydroxy-6a, 12a-dehydrodeguelin (1), 6-hydroxy-6a, 12a-dehydrodeguelin (2), (6aR, 12aR, 4'R, 5'S)-4', 5'-dihydro-4', 5'-dihydroxytephrosin (3), 6'-hydroxy-6a, 12a- dehydrorotenone (4), (-)-rotoic acid (5), (-)-deguoic acid (6), 12-deoxo-12α-acetoxyelliptone (7). CONCLUSION: Compound 1 is a new compound, compounds 2-6 were isolated from this genus for the first time, and compound 7 was isolated from Derris elliptica (Roxb.) Benth. for the first time.

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

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 degrees 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).

A strain of endophytic Pencillium sp., which might produce rotenone or its analogues and showed bioactivity against aphids, was isolated from the fresh roots of Derris elliptica Benth. A total of 12 fractions, isolated from the chloroform extract of endophytic Pencillium sp. mycelia by silica gel column, were tested by bioassay and high-performance liquid chromatography (HPLC), and the more bioactive fractions were found to be D, E and J. Against the adult turnip aphid, Lipaphis erysimi, by dipping at a concentration of 1 mg/ml, the corrected mortalities of fraction D, E and J were 57.68, 63.28 and 69.74% after 48 h of treatment respectively. The three fractions also showed strong antifeeding activity against third instar larvae of Plutella xylostella in a laboratory bioassay. One absorption peak was detected in the HPLC picture of fraction D, it had a similar retention time as that of rotenone, and the chemical constituent, related to the absoption peak, had the same ultraviolet absorption picture as that of rotenone. Then it could be further concluded that the bioactive compounds in the fraction D could be rotenone or its analogous compounds.

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...

Two new rotenoids 4′,5′-dihydroxy-6a,12a-dehydrodeguelin ( 1 ), 11,4′,5′-trihydroxy-6a,12a-dehydrodeguelin ( 2 ), along with two known rotenoids rotenone and deguelin were isolated from the root of Derris elliptica collected in Guangdong Province, China. Their structures were established by extensive spectroscopic analysis.

Using the natural rotenoids rotenone, amorphigenin, deguelin, rotenonic acid, dalpanol and munduserone as examples, their phytochemical biosynthesis has been examined in Derris elliptica, Amorpha fruticosa and Tephrosia vogelii. The rotenoids are advanced isoflavonoids, and construction of their angular Az.drule;Bz.drule;Cz.drule;D-ring systems has been studied experimentally starting out from simple primary metabolites and passing through a series of mainly oxidative phases. The oxidative reactions of rot-2'-enonic acid which biosynthetically form the E-rings of rotenone, amorphigenin, dalpanol and deguelin have been studied in both chemical and stereochemical detail using seedling preparations and the enzyme deguelin cyclase. This investigation has extensively employed substrates isotopically labelled with (14)C, (13)C, (2)H and (3)H and, particularly in connection with E-ring biosynthesis, required new approaches to the demanding chemical and stereochemical requirements of the experimentation.

An overview is presented on recent (1989–19911 investigations on insecticidal plants in China, specially in South China. The main emphasis was laid on studies of Meliaceae including Azadirachta indica, Melia azedarach and M. toosendan, as well as on Rhododendron molle, Derris elliptica, Tephrosia voglii, Ajuga nipponensis, Plumbago idea and Celastrus anplatus. Research work on the bioactivities and application of essential oils from plants for the control of stored-grain insects is also discussed. The results of these investigations reveal a great potential of the active ingredients of a number of Chinese plants for integrated pest management, as well as for using these natural product models as guides for the synthesis of a novel class of insecticides.

Derris elliptica Benth. extracts containing rotenone have long been used as natural insecticides, but time-consuming preparation processes and the short shelf life of the extract limit their use in pest control. In this study, stable water-dispersible granules and emulsifiable concentrate liquids containing Derris extract (equivalent to 5% w/w of rotenone) were developed with simple techniques. Accelerated degradation kinetics of rotenone in the Derris extract, and in both formulations, indicated that its degradation followed first-order kinetics. The predicted half-life (t(1/2)) and shelf life (t(90%)) at 30 degrees C of rotenone in Derris extract were 520 and 79 days, respectively. Derris granules and emulsifiable concentrate clearly prolong the stability of rotenone 8-fold (t(90%) = 633 days) and 1.4-fold (t(90%) = 110 days), respectively. The study of rotenone degradation after application onto plants indicated that both formulations would be effective for up to 3 days after spraying. Preliminary efficacy testing indicated that the Derris emulsifiable concentrate was clearly more effective than Derris water-dispersible granules in controlling Spodoptera litura (Fabricius) (Lepidoptera: Noctuidae).

In Nigeria, fish farmers have traditionally harvested fish by persistently and indiscriminately abusing the use of natural plant piscicides. In particular Derris elliptica , which contains rotenone which is toxic to fish when it is used in higher concentrations than necessary, causing contamination of fresh water bodies and thereby affecting non target organisms. Toxicity studies of Derris elliptica root powder were carried out with juveniles of Clarias gariepinus using sublethal concentrations of the root extracts Derris elliptica in 96 h static bioassay. Estimated numbers of healthy C. gariepinus juveniles were obtained from artisanal fishermen in Ondo State, Nigeria and were transported to the Federal University of Technology, Akure. The 96 h LC50 of Derris elliptica to juveniles of C. gariepinus was observed to be 15.0g/ml. Behavioural activities such as erratic swimming, loss of reflex, hyperventilation, increased surfacing frequency and jerky movements were observed. Values of some haematological parameters of C. gariepinus juveniles were analysed to determine the influence of D. elliptica root powder on the test fish. The range values obtained for the Packed Cell Volume (PCV), Haemoglobin (Hb), Erythrocyte (RBC) for C. gariepinus in higher concentration of D. elliptica root powder were significantly higher; PCV 40.0% - 45.0%, Hb 12.8 – 14.3g /100ml, RBC count 38.5 – 47.4 x 106mm3 than those obtained for Clarias in lower concentrations :PCV 25.0 – 31.2%, Hb 8.3 – 9.8g/100ml, RBC count 21.6 – 32.96 x 106mm2 3 respectively. Erythrocyte Sedimentation Rate (ESR) decreased than those obtained at lower concentrations of the powder. Erythrocyte Sedimentation Rate (ESR) decreased with increase in D. elliptica concentrations. The increase in PCV with increase in D. elliptica concentration indicated positive absorption of Derris solution by the fish while the increase of haemoglobin concentration (Hb) and Erythrocyte count (RBC) in C. gariepinus at higher concentration of D. elliptica may be associated with erythrocytes synthesis.

Two new rotenoids, 2-hydroxy-5-aminorotenonone (1) and elliptoic acid (2), were isolated from the roots of Derris elliptica collected in Guangdong Province, China. Their structures were established by extensive spectral analysis. Compound 1 is the first N-containing rotenoid and compound 2 is the third rotenoid with the cleavage of C(12)-C(12a).

Various parts of Derris elliptica, Derris indica and Derris trifoliata on fractionation with a number of solvents (petrol, dichloromethane, ethyl acetate, butanol and methanol) gave fractions which demonstrated a varied level of broad spectrum antibacterial activity. Good activity was exhibited by the methanol fractions of the leaves and root heart-wood, petrol, butanol and methanol fractions of the root bark of D. indica and petrol and ethyl acetate fractions of D. trifoliata. None of the plants showed antifungal activity.

Callus induction was carried out by tissue culture using leaves of Derris elliptica to obtain rotenoids. A small amount of rotenoids (2.9 µg/gDW) was detected in the callus tissue thus induced and subcultured for 4 months. Rotenoid biosynthesis, however, decreased with frequent subcultures of callus tissue, and was finally lost. Then, a callus with imperfectly differentiated rootlets was induced from the leaves or stems of derris by regulating plant hormones. This root-like organ was found to contain rotenoids which were identified as rotenone and deguelin by GC-MS. The content was 160 µg/gDW as rotenone.

IN THE LAST two decades Derris Lour. and Lonchocarpus HBK have assumed an important commercial position as sources of the insecticide rotenone, and have been subjects of a great number of taxonomic, chemical and agronomic investigations. However, there are few available reports of cytological studies. Chromosome numbers of 2n20 for Derris elliptica and 2n -_ 22 for D. malaccensis were reported by Heyn (1938), who expected to find further differences in number in other species of the same genus. Skalinska (1945) found a 2n number of 22 for D. elliptica; the present study confirms this as the correct number. Cytological studies involving nine species of Lonchocarpus and four species of Derris will be considered here. Lonchocarpus and Derris are continuously recurring sources of taxonomic debate. The two genera are combined under Derris by MacBride (1943), separated by Killip and Smith (1930), Krukoff and Smith (1937), and Hermann (1947). Bentham (1860) in setting up the tribe Dalbergieae suggested that Lonchocarpus, Pongamia, Piscidia, and Muellera should probably be combined under Derris; yet he retained them as separate genera. The principal reason for retaining both Lonchocarpus and Derris is apparently geographical, Louichocarpus being the new world, Derris the old world genus. However, species of each have been described from both regions. Failure of collectors to find flowering or fruiting specimens of various high rotenone species has resulted in descriptions from leaf characters only, so that the nomenclature of these species is especially confusing. For example, L. utilis A. C. Smith, described from a sterile specimen originally determined as L. nicou (Aubl.) DC., is now referred to L. utilis A. C. Smith, L. nicou var. utilis (A. C. Smith) Hermann, or Derris utilis (A. C. Smith) MacBride. Cytological study may aid in clarifying some of the taxonomic problems, as well as contribute useful information toward practical breeding problems. Lonchocarpus utilis, L. nicou, L. urucu, Derris elliptica and D. malaccensis are the principal specific sources of commercial rotenone. Of the two genera Lonchocarpus is considered the better source (Jones, 1942). Various species of no commercial importance are strikingly ornamental in their native habitats or under cultivation. L. punctatus from Venezuela and L. Dominguensis in I Received for publication December 8, 1948. Publication No. 2, Journal Series from the Atkins Garden and Research Laboratory of Harvard University, Soledad, Cienfuegos, Cuba. The problem was supported by the National Research Council and The Bussey Institution of Harvard University. The author is indebted to Dr. Karl Sax, Dr. P. C. Mangelsdorf, Dr. 0. E. White and Dr. A. G. Kevorkian for suggestions and criticisms. Cuba are usually found along stream banks where they produce an abundance of showy, rose-colored, perfumed flowers. Nigerian natives use L. cyanescens in making an indigo dye. Desirable clones of both genera are usually propagated by means of cuttings, since the species root easily. In this manner, under constant environmental conditions, the rotenone percentage of the original plant is preserved. Thus well-known clones with widely distributed members have arisen. MATERIALS AND METHODS.-All collections of Lonchocarpus and Derris included in this study are from permanent plantings at the Atkins Garden and Research Laboratory of Harvard University, Cienfuegos, Cuba. Original source of material, chromosome number, general distribution of the species and the author's collection number are included in table 1. The identity of the collections has been checked, in so far as possible, by comparison with specimens in the herbarium of the Arnold Arboretum and Gray Herbarium; triplicate specimens have been deposited in the Gray Herbarium, National Herbarium and Atkins Garden and Research Laboratory. It was not possible to make herbarium specimens of L. utilis, D. malaccensis, or the various clones of D. elliptica (GM 1, 2, 5, 7 and "Panama") because the cuttings from which chromosome counts were made had not grown sufficiently. Since these cuttings were obtained from clones which are under experimental study for rotenone content, and which have been subject of some of the taxonomic studies, their identities were accepted as reliable. Somatic chromosome determinations were made from acetic orcein smears of young leaves, petals, or root-tips, pretreated for 1 hr. with a saturated solution of paradichlorobenzene (Meyer, 1945) and fixed in Carnoy's solution. Meiotic studies were made on pollen mother cells smeared in acetic orcein without previous fixation. Camera lucida drawings (fig. 1-11) are reproduced at magnification of ca. 2000. OBSERVATIONS.-1.-L. cyanescens, n 11, 2n 22 (fig. 1, 2). Univalents were occasionally seen in metaphase I divis'ion, but anaphase separation was apparently regular. Pollen counts showed 98 per cent of the grains to be full. Although pollen development was apparently normal, the three plants observed are all sterile; they flowered four times in 11 months but no fruit set. Numerous attempts were made to force fruiting artificially: stigmas were bruised, pollen was transferred from other flowers on the same plant, from different plants of the same species, and from L. violaceus. None of these pollinations was successful.

Summary 1 All available parts at all available stages of growth, of twenty-two species of Papilionaceae have been examined microscopically for the presence of rotenoids: fourteen contain them, and Table V summarizes all the plant parts in which they occur. 2 The rotenoid content varies from mere traces in the seeds only of one species to appreciable quantities in nearly every organ of another species. 3 Seeds of twelve of the rotenoid-containing species were available: all contained rotenoids. It appears to be the rule that if any species contains rotenoids in any tissue it will contain them in its seeds. 4 Roots of thirteen of the species were available: twelve contained rotenoids. 5 In general, rotenoid cells in the roots and stems are normal ones, but in all other tissues they are usually morphologically distinct, and frequently relatively very large. 6 Rotenoids occur in the seeds of species of Millettia and Derris not in cells but in iysigenous cavities. 7 In many species rotenoids are first detected in the cortex of the root opposite the protoxylem and primary medullary rays. 8 In general, the roots contain rotenoids in the xylem parenchyma, especially in the medullary rays, and in the cortex. In stems they occur mainly in the pith, when not lignified, and also in the phloem, especially in the rays, and in the cortex. 9 At nodes there is frequently an increase in the number of rotenoid cells, especially in the pith. 10 On germination, the seeds of Mundulea and Tephrosia species at first produce new rotenoid cells, accompanied by an increase in total rotenoid content, in the growing radicle and in the cotyledons. Later, the rotenoids diminish to nil in the radicle and to between 45% and nil. for different species, in the cotyledons. With Millettia. new rotenoid cavities are at first formed in the radicle, and later all rotenoids disappear from it: only a small reduction in the rotenoid content of the oetyledons, however, occurs. With Derris, no new rotenoids are formed in the radicle: the amount in the cotyledons in one species diminished to 62 %. 11 Rotenoids in the plumules of Millettia and Derris species disappear soon after germination. 12 Two instances only of lability of rotenoids have been proved: in the germinating seeds of all species, and in the lignifying pith of the stems of two species. 13 Derris elliptica plants placed in the dark until dead show no reduction in the amount of rotenone per plant: indicating that the rotenone is not available as a food reserve. 14 The application of the sap from Derris roots and stems to Derris cuttings produces no increase in percentage rooting or in the speed of rooting. 15 The results suggest that rotenoids are of some direct use to the germinating seed and seedling, but that they are probably waste products in all other tissues.

The insecticidal principle of the root of Derris elliptica is "Rotenone," a white crystalline material, C23H22O6, melting point 163, solublein ether, acetone,and oils, but insoluble in water. It contains two methoxyl groups, and a ketone group, but its constitution is as yet unknown. It was called rotenone, from the Japanese name of the plant "Roh-ten," by Nagai, who first isolated it in 1902. Dried Derris root contains from 0.5 to 6 per cent rotenone. Rotenone is stable in the dried root or in solution in oil, but decomposes on contact with water or alkalies. For this reason soap emulsions containing rotenone should be prepared only shortly before using. According to Japanese experimenters, rotenone decomposes within 2 days after application to foliage, and hence, vegetables sprayed with it may be subsequently eaten with impunity. In connection with a study of the constitution of rotenone, the Insecticide Division of the Bureau of Chemistry and Soils has prepared from the Derris literature about 250 abstracts, many of which are from sources not readily available. Entomologists who desire to make tests with rotenone or who are interested in the literature of Derris are invited to communicate with the Insecticide Division of the Bureau of Chemistry and Soils, U. S. Department of Agriculture, Washington, D. C.

In rotenone-bearing crops, such as Derris elliptica (Wall.) Benth., in which the root is valued for insecticidal purposes, the yield of root as well as the rotenone content is important. Obviously yield could not be sacrificed to obtain high rotenone percentage, nor could high yield compensate for low rotenone content. A maximum yield of root of uniformly high rotenone content may be considered as a goal. Of the several types of D. elliptica available at this station, one, the St. Croix variety, is characterized by a high yield of root markedly low in rotenone. Another, Changi No. 3, is characterized by a lower yield of root which is relatively high in rotenone. A third variety, the Sarawak Creeping, occupies an intermediate position with regard to rotenone content. The extent to which grafting may modify the yield and rotenone content in Derris roots has never been investigated. The possibility of increasing the rotenone content of the more vigorous St. Croix roots by grafting on scions of the Changi No. 3 seemed promising. Likewise, St. Croix tops on Changi No. 3 roots might increase the yield of roots of the latter. An experiment testing these premises is here reported, the results of which, although negative with regard to the anticipated scion effect, are of interest. A hypothesis under test in this experiment concerned the possibility of the leafy part of the plant supplying some factor, perhaps an intermediate compound, similar to but simpler than rotenone, which was necessary for the completion of the synthesis of rotenone in the roots. This was suggested by the fact that compounds of the rotenone group are chemically related to compounds of the flavone group, of which at least two occur in the leaves of derris.2 Rotenone itself (I) can be considered as an isoflavanone nucleus (II) in which a methoxyl group on 6' is condensed with a hydroxyl group on 2 to result in a bridge. On 7 and 8 there is a pentose residue and on 3' and 4" methoxyl groups. That compounds related to rotenone exist in the root in glycosidic combination (probably acylated) is indicated by the fact that derris resin must be hydrolyzed by mild alkali treatment before crystalline deguelin can be isolated. Methods

RESP-1043

1. Derris elliptica was grown in Puerto Rico at elevations ranging from 50 to 2400 feet above sea level and in Guatemala at altitudes ranging from 910 to 4888 feet. 2. The temperature factor of altitude correlated positively with rotenone and inversely with reserve carbohydrates in derris roots. 3. At elevations favorable to growth of derris plants, the accumulation of rotenone was influenced by major variations in water supply, but reserve carbohydrates were altered by relatively minor variations in available moisture. 4. The varietal selection of Derris grown in Guatemala appeared to be more adapted to higher elevations, in an ecological sense, than the Sarawak Creeping variety grown in Puerto Rico. 5. The normal effect of age on the percentage of rotenone was apparently obscured at high altitudes. 6. Soil pH, ranging from values of 4.7 to approximately neutral, had no measurable effect on rotenone or carbohydrate reserves. 7. At favorable altitudes, derris plants flourished in soils having good physica...

The pyrethrins, nicotine, rotenone and a derris resin have been tested in the laboratory under standard conditions for their ovicidal effect. The test-subjects were : Pieris brassicae, Plutella maculipennis, Aphis rhamni, Ephestia kühniella and Sitotroga cerealella. Notes on the technique of egg production are given for these species. In the majority of the tests made a water medium containing acetone together with sulphonated lorol as a wetting agent was used.It has been shown that all these products are toxic to the species on which they were tested. Lauryl thiocyanate, β-butoxyβ'thiocyanodiethyl ether and 3 : 5 dinitro-o-cresol were included as substances of recognised ovicidal value for purposes of comparison.All the above insecticides derived from plants compared favourably in their toxic action with the synthetics. In two instances during tests on eggs of Ephestia kiihniella, data were obtained enabling a satisfactory statistical comparisdn of relative potency to be made. In the first of these, the pyrethrins were found to be 8·45±1·47 times as toxic as 3 : 5 dinitro-o-cresol, while in the second the pyrethrins were found to be 2·66±0·26 times as toxic as a Derris elliptica resin (rotenone content 37–40 per cent.). It therefore appears that both the pyrethrins and the derris resin were more toxic, weight for weight, than 3 : 5 dinitro-o-cresol which is recognised as one of the most potent ovicides.The above vegetable poisons were found to be toxic not only to eggs developing in a few days without a diapause, but also to those of Aphis rhamni, a species of overwintering egg. The tests on A. rhamni were made at the time the eggs were just starting to hatch. The same result might not have been obtained with eggs at an earlier stage of development.Observations were made on the effect of the different insecticides on the development of the egg. This effect appeared to differ with each substance, either qualitatively or quantitatively, but within the limits of the experiment it seemed to be independent of the species of the egg.

Studies over de veredeling van derris elliptica en derris malaccensis 2.Kruisingswerk, cytologische waarnemingen, genetisch systeem Met kruisingswerk werd in 1935 een aanvang gemaakt in de hoop zaailingen te verkrijgen, waarin het hoge rotenongehalte vanDerris elliptica is gecombineerd met het hoge gehalte verwante insecticiden vanDerris malaccensis. Later is ook massaal kruisingswerk verricht tussen gekweekt en wild materiaal vanDerris elliptica. Het kruisingswerk ondervond vele moeilijkheden, doordat de belangrijkste cloon „ngawi” in het geheel niet bloeit en enkele andere hoogwaardige clonen weliswaar bloeien, maar noch na zelfbestuiving, noch na kruising vrucht zetten. Enkele andere zijn wel te gebruiken, maar op een 1000 tal kruisingen worden toch niet meer dan 7–8 zaden gevormd. Wilde vormen zijn in het algemeen redelijk fertiel en laten zich ook met hoogwaardige gekweekte clonen kruisen. Een groep van de oudste soortshybriden produceerde reeds zoveel wortels, dat daarvan een analyse kon worden gemaakt (tabel 1). Van een jongere groep hybriden van kruisingen tussen gekweekte hoogwaardige en wilde varieteiten vanDerris elliptica en tussen wilde vormen onderling kon colorimetrisch het gehalte aan aetherextract worden bepaald. Op twee planten met 5–6% extract na, bevatte geen van de hybriden practisch enig rotenon. In beide soorten, onder de gekweekte zowel als onder de wilde planten, werden de somatische chromosoomgetallen 22 en 24 gevonden. Het type „pantu” van de soortD. elliptica was triploid met 36 chromosomen. Tevens werden enkele andere soorten onderzocht (tabel 2). Planten met verschillend aantal chromosomen komen willekeurig verspreid voor en morphologisch is er geen verschil tussen beide groepen te constateren. Naar alle waarschijnlijkheid hebben we bij derris te maken met structurele verschillen tussen de chromosomen. Hybriden tussen beide typen bezitien 23 chromosomen. Uit onderzoek van de zaaisels van een zestal willekeurige clonen bleek, dat alle planten vrij sterk heterozygoot zijn, niettegenstaande het zaad in het algemeen door zelfbestuiving ontstaat (tabel 4). Wanneer wordt aangenomen, dat voor het ontstaan van giftige planten enkele factoren recessief aanwezig moeten zijn, dan zullen deze zaailingen slechts door inteelt kunnen ontstaan. Ze zullen daardoor in het algemeen zwakke groeiers zijn, zodat slechts enkelen in de felle strijd om het bestaan tot volwassen planten zullen uitgroeien. De meeste gekweekte vormen zijn inderdaad relatief zwakke groeiers en zo is het te begrijpen, dat onder ± 400 in het wild verzamelde planten er geen enkele giftige is gevonden.

For the investigation of rotenone biosynthesis, acetate-2-14C, mevalonic acid-2-14C lactone and methionine-methyl-14C were administered to Derris elliptica plants, respectively, and the distribution of carbon-14 in the labeled rotenone was determined by degradation. When mevalonic acid-2-14C lactone was incorporated into rotenone, the radioactivity was found equally in the carbons at both C-7' and C-8', indicating that these carbons are derived from the carbon-2 of mevalonic lactone. In the case of methionine-methyl-14C about 80% of the total radioactivity was found to enter two methoxyl groups. This result demonstrates that methionine is an efficient precursor of the methoxyl group. Furthermore, it is also suggested that methionine may be a precursor of the carbon at C-6.

Two amino-acids derived from pipecolic acid have been isolated from leaves of Derris elliptica. Their structure was confirmed by synthesis. They are: 2S-carboxy-4R,5S-dihydroxypiperidine and 2S-carboxy-4S,5S-dihydroxypiperidine.