A series of quassinoids was tested for antifeedant activity against the aphidMyzus persicae (Hemiptera, Aphididae). Isobrucein B, brucein B and C, glaucarubinone, and quassin decreased feeding at concentrations down to 0.05% and isobrucein A was effective at 0.01%. Only quassin showed no phytotoxic effects and is therefore the most promising compound for further development.

aeEPILU -A new cell growth inhibitory acetogenin, designated mlliniastatin 2. has k e n isolated fmm seeds of the South American Rollinia mucosa (Annonaccae) and its structure determined.A diasareomeric relationship for rolliniastatin 1. mlliniasratin 2, and asimicin was proposed.Thc Rollinia genus (Annonaceac) is composed of some 65 species occurring principally fmm Central America to Argentina.Thr few species so far examined (chemically) fmm each of the Annona; Asimina.Rollinia, and Uvnria genera have been found m contain members of a new class of biologically active bistcmhydmfurans.Ourcrysral structure determination of mlliniastatin 12 pmvided the fmt definitive srmctun in this new series.3-10By x-ray nystzllography, the relative stereochemistry of mlliniastatin 1 was established as 4s'.15s'.16S*, 19R*, 20R*, 23S*, 24P.and 36111.2Asimicin, recently isolated fmm Asimina friloba?apparently differs fmm mlliniasudn I in its configuration at one or more of the c h i d c e n w associated with the bis-terr.khydrofuransystem Funher detailed fractionation of a hcxanc extract of Roliinia mucosa seeds has led us to uncover companions of rolliniastatin 1, including asimicin and a new diasterenmer of mlliniastatin 1. named mlliniastatin 2.Isolation of rolliniastatin 2 was effected by consecutive applications of solvent partitioning, flash chmmatography on silica gel, high-speed countercurrent distribution WCCD)I' with a multilayer mil planet centrifuge,12 column chromatography (LiChrom Si60).and W y hplc (semiprepmtivf with Panisill0 silica gel followed by analytical with Partisil5 silica gel) with the solvent system hexane -ethyl ethermethanol.With a hplc flow rate of 1.5 d m i n , emergence times (mi@ wen: mlliniasutin 1. 6.17; asimicin.6.57; rolliniaslatin 2. 6.70.High resolution sp-sims analysis of mlliniastatin 2 pmvided molecular formula C37H,&7 (mlz 623.4885; calcd for C37H6607 + H, 623.4866).The uv. ir. and eims spectra of rolliniastatin 2 wen similar w those reported for rolliniastatin 1.2 asimicin,g and 14-hydroxy-25-desoxyrollinicin.9By thin-layer chmmamgraphic comparison in dichloromethanemethanol (19:1), mlliniastalin 2 was hardly distinguishable

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTInsect Antifeedant and Growth Inhibitory Activity of Forty-Six Quassinoids on Two Species of Agricultural PestsZev Lidert, Keith Wing, Judith Polonsky, Yasuhiro Imakura, Masayoshi Okano, Shohei Tani, Yuh-Meei Lin, Hiroshi Kiyokawa, and Kuo-Hsiung LeeCite this: J. Nat. Prod. 1987, 50, 3, 442–448Publication Date (Print):May 1, 1987Publication History Published online1 July 2004Published inissue 1 May 1987https://pubs.acs.org/doi/10.1021/np50051a016https://doi.org/10.1021/np50051a016research-articleACS PublicationsRequest reuse permissionsArticle Views218Altmetric-Citations40LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Rolliniamucosa (Annonaceae), known in primitive medical practices of Indonesia and the West Indies as a treatment for tumors, has been investigated employing the seeds from a South American variety and the murine P388 lymphocytic leukemia (PS) for bioassay. The principal antineoplastic constituent (PS, 28% life extension, at 0.25 mg/kg and ED504.5 × 10−5 μg/mL) was found to be a new bis-tetrahydrofuran designated rolliniastatin 1. Structural elucidation of rolliniastatin 1 was accomplished by a combination of high resolution nuclear magnetic resonance (300 MHz), mass spectral, and X-ray crystal structure techniques.

The structure of a neoflavanoid isolated from Pityrogramma calomelanos was confirmed by an X-ray diffraction study.

Biologically inactive but easily available chaparrin 2a has been converted into potent antileukemic C-15 esters of glaucarubolone 2b and quassinoid analogs in which the C-15 ester side chain has been replaced by an alkyl or alkenyl group.The synthetic methodology developed has been applied to the preparation of C-15 ester derivatives 15, 16, 17 and quassinoid analogs 12, 13 and 14.

Two new sesquiterpene aryl esters 15-hydroxy-5′-O-methylmelledonal and 5′-O-methylmelledonal, were isolated from the culture broth extract

Incorporation of [1-13C]-, [2-13C]-, and [1,2-13C2]-acetates and [2-13C]-mevalonate into fomajorin D supports its biosynthetic derivation from a humulene-type precursor via cyclization of trans, trans-farnesyl pyrophosphate. [1,2-13C2]Acetate derived fomajorin D was not converted in vitro into fomajorin S. However, the stereochemistry of fomajorin S is proposed on the basis of its biosynthetic origin.

Two new quassinoids, 13, 18-dehydro-6 alpha-senecioyloxychaparrin (4) and 12-dehydro-6 alpha-senecioyloxychaparrin (5), have been isolated from Simaba multiflora fruits. Their structures were deduced from spectral data. 1H-13C 2-D chemical-shift correlation nmr was applied to the structural elucidation of the antileukemic quassinoid 4.

AbstractConformational factors have been found responsible for the dramatic change in odor between (−)‐deoxyambreinolide (12) and its (+)‐epi derivative 13. The presumably molecular event during the receptor interaction has been simulated by the diastereoisomeric 11‐methyl‐ambrox derivatives 3 and 5 as model compounds.

The antimalarial activity of sergeolide (a quassinoid from PICROLEMMA PSEUDOCOFFEA) was investigated both, IN VITRO on PLASMODIUM FALCIPARUM cultures and IN VIVO through a classical test of schizontocidal action against PLASMODIUM BERGHEI in mice. Sergeolide showed a very strong antiplasmodial activity IN VITRO as well as IN VIVO. Low concentrations (0.006 microg/ml) were able to fully inhibit the IN VITRO growth of chloroquine-sensitive and resistant strains of P. FALCIPARUM. Small amounts (0.26 mg/kg/day) markedly reduced the virulence of experimentally induced P. BERGHEI infection in mice. However, sergeolide, because of its high toxicity (LD 50: 1.8 mg/kg), does not seem, in its present form to be useful for malaria curative treatment.

Chemical ionization and fast atom bombardment mass spectra of a series of phospholipids related to PAF-acether are reported. The usefulness of these methods towards their structural determination is discussed. The mass spectra of sphingomyelin are also examined.

The structure of 15-O-benzoyl-brucein D, a new quassinoid isolated from Soulamea amara Lam., has been established from spectral data and by single-crystal X-ray analysis ; the previously known picrasin B, isobrucein A and B were also isolated.

The structure of 15-O-benzoyl-brucein D, a new quassinoid isolated from Soulamea amara Lam., has been established from spectral data and by single-crystal X-ray analysis ; the previously known picrasin B, isobrucein A and B were also isolated.

AbstractThe structure of boronolide (I) is established to be (6R, l ′R,2′R,3′S) by means of X‐ray diffraction analysis.

The structures and isolation of eight compounds from Dalbergia monetaria seeds are described. Four of them are known rotenoids. In addition to a new isoflavone and its 7-β-D-glucoside, the first 12-dihydrorotenone, 12-dihydrodalbinol, and its 8′-β-D-glucoside were identified.

Isolation of two new sesquiterpene aryl esters melledonal (6) and melledonol (8) from culture broth extract of Armillaria mellea are reported. Their structures were deduced from spectral and chemical data.

Investigation of the mycelial extract of Armillaria mellea led to the isolation of the known melleolide (2a) and two new sesquiterpene aryl eters, 4-O-methylmelleolide (2b) and judeol (1c). Their structures were deduced from spectral data and that of (2b) confirmed by X-ray analysis. The new esters (1c) and (2b) showed strong antibacterial activity against gram-positive bacteria.