Zur biosynthese der iridoidglucoside

Inouye, Hiroyuki; Ueda, Shinichi; Aoki, Yasuhiko; Takeda, Yoshio

doi:10.1016/s0040-4039(01)88162-4

Cited by 18 publications

(15 citation statements)

References 6 publications

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“…It has been shown elsewhere that 5 may be biosynthesized from loganic acid (16) in Daphniphyllum macropodum (Daphniphyllaceae) and Aucuba japonica (Aucubaceae). 21 Incorporation of 7-3 H-loganin (17) into secologanin (18) and into strictosidine (19) in Catharanthus roseus (Apocynaceae) corroborates that secologanin was formed via loganin 22 . In other studies on the subject it has been shown that secoiridoids are formed through this biosynthetic route 3,25,26 .…”

Section: Recent Trends In Iridoid Biosynthesismentioning

confidence: 85%

“…It was found also that deoxyloganic acid (8) was incorporated into asperuloside (9) in Theligonum cynocrambe (Rubiaceae) while 6 was not 16 . It could therefore be deduced that the tricyclic product 9 from the monocyclic monoterpene cyclization was not 1, but iridodial (10) 20 , meanwhile, in feeding experiments with Gardenia jasminoides (Rubiaceae) cell suspension cultures the following sequence was proved: tarennoside (11) → 12 → geniposide (13) → gardenoside (14), all of which are formed from 1 18,19 , as well as from 8 21 .…”

Section: Recent Trends In Iridoid Biosynthesismentioning

confidence: 99%

“…However this biosynthetic approach seems to be incoherent since there are compounds with double bonds at C 7 -C 8 , C 8 -C 9 e C 8 -C 10 , e.g. 5 may be originated from two different routes 13,21 . Nevertheless this fact has been explained tentatively as the result of phytotoxic effect of the precursor on the plant 15 or yet, due to the fact that the same iridoid glucoside may be biosynthesized by different cyclization processes in different plant species.…”

Section: Recent Trends In Iridoid Biosynthesismentioning

confidence: 99%

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Biosynthesis significance of iridoids in chemosystematics

Sampaio-Santos¹,

Kaplan²

2001

J. Braz. Chem. Soc.

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Iridóides são substâncias monoterpenoídicas formadas em plantas por uma ciclização alternativa do pirofosfato de geranila. A estrutura química dessas substâncias é baseada no esqueleto ciclopentano-[C]-pirano, iridóides carbocíclicos, e a clivagem oxidativa da ligação 7,8 do anel ciclopentano fornece os chamados secoiridóides. Sob o aspecto biogenético, os iridóides são biossintetizados a partir do cátion iridodial e diversificam-se em 27 vias diferentes. Iridóides têm sido usados como marcadores quimiotaxonômicos para as superordens Corniflorae, Gentianiflorae, Loasiflorae e Lamiiflorae. O número e a natureza dos iridóides encontrados no Reino Vegetal são indicativos da complexidade das vias envolvidas na sua biossíntese. Em Quimiossistemática, os iridóides representam um marcador importante em classificação vegetal, filogenia e evolução.Iridoids represent a large group of monoterpenoid compounds that apparently seem to be formed in plants by an alternative cyclization of geranyl diphosphate. The structures of these compounds are based on a cyclopentan-[C]-pyran skeleton, carbocyclic iridoids, and oxidative cleavage at the 7,8-bond of the cyclopentane moiety affords the so called secoiridoids. On biogenetic grounds the iridoid formation may be considered to start from iridodial cation and follow diversification through 27 different routes. Iridoids have been used as chemical markers for the Corniflorae, Gentianiflorae, Loasiflorae and Lamiiflorae superorders. The number and nature of the iridoids occurring in plants are a measure of the complexity of the routes involved in their biosynthesis. In chemosystematics, the value of iridoid character shows important significance in plant classification, phylogeny and evolution

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Section: Recent Trends In Iridoid Biosynthesismentioning

confidence: 85%

Section: Recent Trends In Iridoid Biosynthesismentioning

confidence: 99%

Section: Recent Trends In Iridoid Biosynthesismentioning

confidence: 99%

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Biosynthesis significance of iridoids in chemosystematics

Sampaio-Santos¹,

Kaplan²

2001

J. Braz. Chem. Soc.

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“…Desoxyloganin) und Loganin (od. Loganinsaure) entstehen [6,9,10,111, und dai3 die Secoiridoidglucoside wie Swerosid, Swertiamarin, Gentiopicrosid, Morronisid, Oleosid usw. aus Loga-nin (od.…”

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Neuere Ergebnisse über die Biosynthese der Glucoside der Iridoidreihe

Inouye¹

1978

Planta Med

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var. echinosperrnon was established by the administrztion experiments of seve-Intermediacy of iridodial for the bio-ral labeled precursors to these plants. synthesis of iridoid glucosides in La-Administration experiments of severnittrn arnplexicaule, Detttzia crenata, ral substances to the cultured cells of Patrinia gibbosa and Galium spuriurn Gardenia jasrninoides f. grandiflora de-Heruntergeladen von: University of Illinois. Urheberrechtlich geschützt. Schema I . Der Hauptbiosyntheseweg der Iridoid-und Secoiridoidglucoside sowie der Indolalkaloide Heruntergeladen von: University of Illinois. Urheberrechtlich geschützt. Biosynthesis of lridoidglucosides 195 SCANDOS ID AcO ASPERULOSID COOH HO AUCUBIN VERSCHIEDENE IRIDOIDGLUCOSIDE SWEROSID SWERT[AMAR[N GENTIOPICROSID C0OCH-j ' OOC

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“…Alternatively decarboxylation of corresponding carboxylic acids would provide a route to the CS cyclopentanoid monoterpenes such as aucubin (11) (Scheme 11). Inouye et al (1969a) has provided support for this hypothesis by labeling a 7-desoxyloganic acid (8), feeding it to various plants, and demonstrating direct conversion of this acid 8 into loganin (3), aucubin (11) (Scheme 11), asperuloside, and verbenalin.…”

mentioning

confidence: 92%

Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis

Coscia¹,

Guarnaccia²,

Botta³

1969

Biochemistry

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Gentiopicroside (l), a secoiridoid monoterpene glucoside, and loganic acid (2), a new naturally occurring iridoid monoterpene glucoside, have been isolated from the same higher plant, Swertia caroliniensis. These congeners have been characterized by chemical and spectral means. Doubleresonance nuclear magnetic resonance studies corroborated a recently revised structure 1 for gentiopicroside, isomeric to the previously designated one l a . Loganic acid has been identified by methylation to loganin (3), and acetylation to pentaacetate derivatives. Tracer experiments with acetate-2-14C, mevalonate-2-14C (6), and me~alonate-2-~H have established the mevalonoid origin of the aglucone moieties of the glucosides. Conversion of mevalonate-labeled gentiopicroside into genti-G entiopicroside (1) and loganic acid (2) belong to a class of highly oxygenated monoterpene glucosides referred to as secoiridoids and iridoids, respectively. (For a review of the iridoids (cyclopentanoid monoterpenes), see Bobbitt and Sege-

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Zur biosynthese der iridoidglucoside

Cited by 18 publications

References 6 publications

Biosynthesis significance of iridoids in chemosystematics

Biosynthesis significance of iridoids in chemosystematics

Neuere Ergebnisse über die Biosynthese der Glucoside der Iridoidreihe

Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis

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