Insect Antifeedants from Tropical Plants:  Structures of Dumnin and Dumsenin

Nihei, Keiji; Asaka, Yukihiro; Mine, Yoshihiro; Ito, Chihiro; Furukawa, H; Ju‐ichi, Motoharu; Kubo, Isao

doi:10.1021/jf049819c

Cited by 17 publications

(51 citation statements)

References 19 publications

(25 reference statements)

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“…Although other alternative methods have been investigated on the biological control, as well as the development of resistant transgenic plants, the control of S. frugiperda still relies mainly on the use of chemical pesticides, easily inducing resistance and causing severe damage to the environment and consumers. However, some natural products with higher selectivity and safety become an important potential source of new biopesticides for the control of S. frugiperda [ 1 , 2 , 3 , 4 , 5 ]. Sf9 cells are clonal isolates of S. frugiperda Sf21 cells (IPLB-SF21-AE) [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri

Lan

et al. 2016

Marine Drugs

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The marine fungus Neosartorya pseudofischeri was isolated from Acanthaster planci from the South China Sea. In a preliminary bioactivity screening, the crude methanol extract of the fungal mycelia showed significant inhibitory activity against the Sf9 cell line from the fall armyworm Spodoptera frugiperda. Five novel compounds, including 5-olefin phenylpyropene A (1), 13-dehydroxylpyripyropene A (4), deacetylsesquiterpene (7), 5-formyl-6-hydroxy-8-isopropyl-2- naphthoic acid (9) and 6,8-dihydroxy-3-((1E,3E)-penta-1,3-dien-1-yl)isochroman-1-one (10), together with eleven known compounds, phenylpyropene A (2) and C (3), pyripyropene A (5), 7-deacetylpyripyropene A (6), (1S,2R,4aR,5R,8R,8aR)-1,8a-dihydroxy-2-acetoxy-3,8-dimethyl-5- (prop-1-en-2-yl)-1,2,4a, 5,6,7,8,8a-octahydronaphthalene (8), isochaetominine C (11), trichodermamide A (12), indolyl-3-acetic acid methyl ester (13), 1-acetyl-β-carboline (14), 1,2,3,4-tetrahydro-6-hydroxyl-2-methyl-l,3,4-trioxopyrazino[l,2-a]-indole (15) and fumiquinazoline F (16), were obtained. The structures of these compounds were determined mainly by MS and NMR data. The absolute configuration of 9 was assigned by the single-crystal X-ray diffraction studies. Compounds 1–11 and 15 showed significant cytotoxicity against the Sf9 cells from S. frugiperda.

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Section: Introductionmentioning

confidence: 99%

Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri

Lan

et al. 2016

Marine Drugs

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“…These five Croton species have high pharmaceutical value due to alkaloids [14,15], diterpenoids [14,16], esters [14,15], furanoditerpenoids [23,24], limonoids [25][26][27][28][29], methylcyclohexane [14,15,30], steroids [15] and triterpenoids [14,15] that have been isolated from bark, leaves and roots. Chhabra et al…”

Section: Phytochemistry and Pharmacological Activitiesmentioning

confidence: 99%

“…Ndunda [14] and Ndunda et al [15] isolated methylcyclohexane, pentacyclic triterpenoid, ester, alkaloid and steroid compounds, namely crotepoxide, dideacetylcrotepoxide, monodeacetylcrotepoxide, αsenepoxide, β-senepoxide, (+)-(2S, 3R)-diacetoxy-1benzoyloxymethylenecyclohex-4, 6-diene, acetyl aleuritolic, alienusolin, benzyl benzoate, crotonimide C, julocrotine and 24-ethylcholesta-4,22-dien-3-one24ethylcholesta-4,22-dien-3-one24-ethylcholesta-4,22dien-3-one from leaves and roots of C. alienus (Table 3). Limonoids, namely dumsin, zumsin, zumketol, zumsenin, zumsenol, dumnin, dumsenin, musidunin and musiduol were isolated from root bark of C. jatrophoides [25][26][27][28][29] (Table 3). Mbwambo et al [23] and Magadula et al [24]…”

Section: Phytochemistry and Pharmacological Activitiesmentioning

confidence: 99%

“…Nihei et al [26][27][28][29] evaluated insect antifeedant activities of compounds dumnin, dumsenin, musidunin, musiduol, zumketol and zumsinisolated from C. jatrophoides using leaf disk assay and second-instar larvae of Pectinophora gossypiella and Spodoptera frugiperda as test organisms. The two compounds showed antifeedant activities with 50% protective concentration (PC 50 ), PC 90 and PC 95 values ranging from 0.5 µg/mL to 36 µg/mL against the larvae of Pectinophora gossypiella and Spodoptera frugiperda [26][27][28][29]. Similarly, Kinyoda et al [36] evaluated antifungal activities of hexane, ethyl acetate and methanol root, bark and leaf extracts of C. jatrophoides against Fusarium oxysporum f. sp.…”

Section: Ent-clerodane Diterpenoidsmentioning

confidence: 99%

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A Review of Phytochemistry and Pharmacological Properties of Threatened Croton Species Used as Herbal Medicines in East Africa

Maroyi

2018

J. Pharm. Nutr. Sci.

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Some rare and threatened Croton species have a long history of medicinal usage in East Africa. The objective of this study was to review the phytochemistry and pharmacological properties of five Croton species that are threatened with extinction in East Africa but widely used as herbal medicines in the region. Information on medicinal uses, phytochemistry and pharmacological properties of C. alienus, C. dictyophlebodes, C. jatrophoides, C. megalocarpoides and C. talaeporos was obtained from databases such as Scopus, Web of Science, Science Direct, Google Scholar, PubMed, BioMed Central (BMC), Springerlink and Scielo. Other sources of information included scientific publications, conference proceedings, theses, books and book chapters obtained from libraries. Literature search revealed that the bark, fruits, leaves and roots of these five Croton species are commonly used as traditional medicines for gastro-intestinal disorders, colds and influenza, body pains and weaknesses and intestinal worms. Phytochemical compounds isolated from these species include alkaloids, anthraquinones, diterpenoids, esters, flavonoids, furanoditerpenoids, limonoids, methylcyclohexanes, phenolics, steroids, tannins and triterpenoids. Pharmacological studies indicate that these species have antifungal, anti-leishmanial and insect antifeedant activities. Preliminary phytochemical and pharmacological research done so far on Croton species is promising, but too general to corroborate some of the medicinal uses of the species.

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“…In addition chemical constituents with interesting biological activities have been obtained from this genus, such as insect antifeedant, antitumor and antifungal agents, and compounds active against digestive disorders, inflammation, fever, and malaria [3]. From Croton jatrophoides, a series of limonoids with insect antifeedant properties has been isolated [4], [5], [6], [7]. As part of our continuing studies on Tanzanian plants with medicinal interest [8], [9], [10], we examined the extract of roots of C. jatrophoides.…”

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confidence: 99%

New Furanoditerpenoids fromCroton jatrophoides

Mbwambo¹,

Foubert²,

Chacha³

et al. 2008

Planta Med

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Four furanoditerpenoids were isolated from roots of Croton jatrophoides (Euphorbiaceae) collected in Tanzania. In addition to the known compounds penduliflaworosin and teucvin (mallotucin A), a new teucvin isomer, which was named isoteucvin, and a furanoditerpenoid with a new skeleton, for which the name jatrophoidin was adopted, were isolated. Their structures were elucidated by spectroscopic methods such as ESI-MS and NMR, including (1)H-, (13)C-, and two-dimensional NMR. The crystal structures of isoteucvin and jatrophoidin were solved using single-crystal X-ray diffraction, by which we also established the absolute configuration of jatrophoidin. The refined crystal structure of isoteucvin has the same (absolute) configuration as jatrophoidin, although the X-ray diffraction data of isoteucvin were not conclusive with respect to the absolute configuration.

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Insect Antifeedants from Tropical Plants: Structures of Dumnin and Dumsenin

Cited by 17 publications

References 19 publications

Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri

Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri

A Review of Phytochemistry and Pharmacological Properties of Threatened Croton Species Used as Herbal Medicines in East Africa

New Furanoditerpenoids fromCroton jatrophoides

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