- Discovery of Glycosylated Genipin Derivatives as Novel Antiviral, Insecticidal, and Fungicidal Agents
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A series of novel genipin glycoside derivatives incorporating 11 glycosidic moieties at either the 1 or 10 position of genipin were designed and synthesized. These compounds exhibited moderate to excellent inhibitory activities against tobacco mosaic virus. Especially, the in vitro and in vivo activities of compounds 6e, 7c, 7d, 7f, 7h, and 7i were comparable to that of ribavirin. In particular, compound 7c, the mannosyl derivative of genipin at the 10 position, showed the best activity. The series of genipin glycosyl derivatives also displayed fungicidal activities against 14 kinds of phytopathogenic fungi, especially for Rhizoctonia cerealis and Sclerotinia sclerotiorum. Moreover, compound 6h exhibited good insecticidal activity against diamondback moth; compounds 7b, 7c, and 7g exhibited moderate insecticidal activity against three kinds of Lepidoptera pests (oriental armyworm, cotton bollworm, and corn borer); and compound 7e showed excellent larvacidal activities against mosquito.
- Xia, Qing,Dong, Jianyang,Li, Ling,Wang, Qiang,Liu, Yuxiu,Wang, Qingmin
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- Asymmetric total synthesis of the iridoid β-glucoside (+)-geniposide via phosphine organocatalysis
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Phosphine-catalyzed [3 + 2] cycloaddition of ethyl-2, 3-butadienoate with enone (S)-3b occurs with high levels of regio- and stereocontrol to deliver the c/s-fused cyclopenta[c]pyran 4 characteristic of the iridoid family of natural products. Cycloadduct 4 was converted to the iridoid glycoside (+)-geniposide in 10 steps.
- Jones, Regan A.,Krische, Michael J.
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supporting information; experimental part
p. 1849 - 1851
(2009/09/06)
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- Hair dyeing by iridoid glycosides and aglycons thereof
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A method of dyeing hair which comprises contacting hair with an iridoid glycoside or an aglycon thereof.
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- IRIDOID GLUCOSIDES IN AVICENNIA MARINA
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Key Word Index - Avicennia marina; Verbenaceae; iridoids; geniposidic acid; mussaenosidic acid; 2'-cinnamoylmussaenosidic acid; 10-O-(5-phenyl-2,4-pentadienoyl)-geniposidic acid; 7-O-(5-phenyl-2,4-pentadienoyl)-8-epiloganic acid. - 2'-Cinnamoyl-mussaenoside , 10-O-(5-phenyl-2,4-pentadienoyl)-geniposide, 7-O-(5-phenyl-2,4-pentadienoyl)-8-epiloganin, and the known iridoids geniposide and mussaenoside have been isolated from a methylated extract of the leaves of Avicennia marina.Evidence is presented that the iridoids occur as the free acids in the plant.The taxonomic significance of these findings is discussed.
- Koenig, Gabriele,Rimpler, Horst
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p. 1245 - 1248
(2007/10/02)
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- Red coloring composite and the method for its production
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PCT No. PCT/JP78/00054 PCT Filed Dec. 14, 1978 Sec. 371 Date Aug. 9, 1979 Sec. 102(e) Date Aug. 9, 1979 PCT Pub. No. WO79/00394 PCT Pub. Date Jul. 12, 1979. Novel reddish coloring compounds of varying hue and the method for its production, obtained by reaction between iridoid compounds contained in biological substances, where if necessary, by pretreatment with chemical or enzymic means to form --COOH at the C-4 position, and in the case of glycosides by hydrolysis of iridoid compounds to aglycones with chemical or microbial or enzymic means, and a substance possessing a primary amino group under acidic condition.
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