Dehydroodorin, a cytotoxic diamide from the leaves of Aglaia formosana

Duh, Chang‐Yih; Wang, Shang‐Kwei; Hou, Rei Sheu; Wu, Yang Chang; Wang, Yu; Cheng, Ming Chu; Chang, Tai Tsung

doi:10.1016/0031-9422(93)85373-y

Cited by 20 publications

(15 citation statements)

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“…Based on HPLC−UV screening, both species, as well as the collections of A. edulis and A. silvestris were mainly characterized by an accumulation of bisamides and/or lignans. Derivatives from both classes of compound have already been reported for other Aglaia species, − and bisamides were shown to exhibit cytotoxic 12,14 and antiviral activity …”

Section: Resultsmentioning

confidence: 89%

“…Based on HPLC-UV screening, both species, as well as the collections of A. edulis and A. silvestris were mainly characterized by an accumulation of bisamides and/or lignans. Derivatives from both classes of compound have already been reported for other Aglaia species, [8][9][10][11][12][13][14][15] and bisamides were shown to exhibit cytotoxic 12,14 and antiviral activity. 13 Altogether the leaf extracts of the five Aglaia species investigated were shown to produce seven different bisamides containing either putrescine or the corresponding pyrrolidine ring as a diamine part always linked to two different acid moieties.…”

Section: Resultsmentioning

confidence: 99%

“…The pyrrolidine derivatives odorine (1) and odorinol (2), already described from A. odorata Lour. 9 and an Indian provenance of A. elaeagnoidea, 10 were now also isolated from a Thai collection of A. elaeagnoidea, and the related dehydroodorine (3) 12 was found as a minor constituent in the leaf extract of A. tomentosa collected in Malaysia. From this group, odorine (1) especially appears to be more widely distributed within Aglaia and has already been reported from A. argentea Blume and A. forbesii King 34 as well as from A. elliptica Blume (syn.…”

Section: Resultsmentioning

confidence: 99%

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Bisamides, Lignans, Triterpenes, and Insecticidal Cyclopenta[b]benzofurans from Aglaia Species

et al. 1998

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Twelve new derivatives of bisamides [piriferinol (5), edulimide (7)], lignans [lariciresinol acetat (10)], triterpenes [4-bis-norcycloartane-type triterpenes (11a, 12a+b, 13a+b)], cyclopenta[b]benzofurans [pannellin (15), pannellin 1-O-acetate (16), 3'-methoxypannellin (17)], and an aromatic butyrolactone [aglalactone (18)] were isolated and identified from lipophilic leaf, stem, and root extracts of Aglaia spp. elaeagnoidea, edulis, grandis, silvestris, and tomentosa. Two cyclopenta[b]benzofurans (flavaglines), pannellin (15) and pannellin 1-O-acetate (16), displayed very strong insecticidal activity against Spodoptera littoralis and Lymantria dispar, comparable with the activity of azadirachtin.

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Section: Resultsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Bisamides, Lignans, Triterpenes, and Insecticidal Cyclopenta[b]benzofurans from Aglaia Species

et al. 1998

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“…However, the structure was drawn in error showing the configuration at C-11 opposite to what had been established by the crystal structure. 10) Misinterpretation of the X-ray data and of the configuration at C-11 has led to confusion in the literature, and this error has been propagated in many of the later papers 11,12) and reviews. 13) Sato et al reported the C-11 epimer 14) and Shoji et al reported its C-5 epimer and named it sinuleptolide, 15) hence the name 5-episinuleptolide for compound 1.…”

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confidence: 99%

Microbial Transformation of 5-Episinuleptolide

Kamel

Fronczek

Khalifa

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…1, it represents the structural prerequisit for the incorporation of bisamides into flavaglines. As shown in Table 1A and B the cinnamic acid-derived bisamides are frequently linked with 2-methyl butyric acid as second acid part which shows further variation by different hydroxylations, dehydrations (tiglic acid), and stereochemistry (Hayashi et al 1982;Duh et al 1993;Saifah et al 1993;Duong Fig. 1 Proposed biogenetic correlation between flavagline skeletons (note the numbering of the benzopyran ring is used here for all structures) (Bacher et al 1999(Bacher et al ) et al 2007).…”

Section: Bisamidesmentioning

confidence: 99%

Comparative phytochemistry of flavaglines (= rocaglamides), a group of highly bioactive flavolignans from Aglaia species (Meliaceae)

Greger

2021

Phytochem Rev

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Flavaglines are formed by cycloaddition of a flavonoid nucleus with a cinnamic acid moiety representing a typical chemical character of the genus Aglaia of the family Meliaceae. Based on biosynthetic considerations 148 derivatives are grouped together into three skeletal types representing 77 cyclopenta[b]benzofurans, 61 cyclopenta[bc]benzopyrans, and 10 benzo[b]oxepines. Apart from different hydroxy, methoxy, and methylenedioxy groups of the aromatic rings, important structural variation is created by different substitutions and stereochemistries of the central cyclopentane ring. Putrescine-derived bisamides constitute important building blocks occurring as cyclic 2-aminopyrrolidines or in an open-chained form, and are involved in the formation of pyrimidinone flavaglines. Regarding the central role of cinnamic acid in the formation of the basic skeleton, rocagloic acid represents a biosynthetic precursor from which aglafoline- and rocaglamide-type cyclopentabenzofurans can be derived, while those of the rocaglaol-type are the result of decarboxylation. Broad-based comparison revealed characteristic substitution trends which contribute as chemical markers to natural delimitation and grouping of taxonomically problematic Aglaia species. A wide variety of biological activities ranges from insecticidal, antifungal, antiprotozoal, and anti-inflammatory properties, especially to pronounced anticancer and antiviral activities. The high insecticidal activity of flavaglines is comparable with that of the well-known natural insecticide azadirachtin. Comparative feeding experiments informed about structure–activity relationships and exhibited different substitutions of the cyclopentane ring essential for insecticidal activity. Parallel studies on the antiproliferative activity of flavaglines in various tumor cell lines revealed similar structural prerequisites that let expect corresponding molecular mechanisms. An important structural modification with very high cytotoxic potency was found in the benzofuran silvestrol characterized by an unusual dioxanyloxy subunit. It possessed comparable cytotoxicity to that of the natural anticancer compounds paclitaxel (Taxol®) and camptothecin without effecting normal cells. The primary effect was the inhibition of protein synthesis by binding to the translation initiation factor eIF4A, an ATP-dependent DEAD-box RNA helicase. Flavaglines were also shown to bind to prohibitins (PHB) responsible for regulation of important signaling pathways, and to inhibit the transcriptional factor HSF1 deeply involved in metabolic programming, survival, and proliferation of cancer cells. Flavaglines were shown to be not only promising anticancer agents but gained now also high expectations as agents against emerging RNA viruses like SARS-CoV-2. Targeting the helicase eIF4A with flavaglines was recently described as pan-viral strategy for minimizing the impact of future RNA virus pandemics.

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Dehydroodorin, a cytotoxic diamide from the leaves of Aglaia formosana

Cited by 20 publications

References 1 publication

Bisamides, Lignans, Triterpenes, and Insecticidal Cyclopenta[b]benzofurans from Aglaia Species

Bisamides, Lignans, Triterpenes, and Insecticidal Cyclopenta[b]benzofurans from Aglaia Species

Microbial Transformation of 5-Episinuleptolide

Comparative phytochemistry of flavaglines (= rocaglamides), a group of highly bioactive flavolignans from Aglaia species (Meliaceae)

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