Studies on Monoterpene Glucosides and Related Natural Products. XVII. The Intermediacy of 7-Desoxyloganic Acid and Loganin in the Biosynthesis of Several Iridoid Glucosides

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

doi:10.1248/cpb.20.1287

Cited by 22 publications

(5 citation statements)

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“…1-[a,a-Bithienyl]-4-chloro-but-1-yn-3-yl acetate (4) The occurrence of these four known compounds is in good agreement with the biogenetically pathways previously described (4,5) and it confirms the original character of the Stigmaphyllon genus in the Malpighiaceae family. …”

supporting

confidence: 83%

Iridoids of Guyanese Species of Stigmaphyllon

Davioud¹,

Bailleul²,

Delaveau³

et al. 1985

Planta Med

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Planta Medica 1985 natural products has not been reported from species belonging to the subtribe Pectidinae where thiophene acetylenes are widespread. Experimental The plant material was collected near Monterrey, Mexico, in April 1984, voucher 1639/ 84. The air dried material was extracted at room temp. with methanol/ether/petrolether, 1: 1: 1, and the extracts obtained were separated first by column chromatography (Si02). The roots (145 g) gave a fraction with ether/petrolether, 1: 10, which gave by TLC (ether/ petrolether, 1:20)5mg 2 and 3.5 mg 6. The CC fraction obtained with ether! petrolether, 1: 1, afforded by TLC (ether! petrolether, 1: 1) 3 mg 4 and 3 mg 1. The extract of 450 g aerial parts gave by CC and TLC (s.a.)5mg2,4mg4,3mg3,3.Smg5and3.5 mg sakuranetin. The compounds were identified by comparing the 400 MHz 1H-NMR spectra with those of autentic material. 1-[a,a-Bithienyl]-4-chloro-but-1-yn-3-yl acetate (4): Yellow oil; IR

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supporting

confidence: 83%

Iridoids of Guyanese Species of Stigmaphyllon

Davioud¹,

Bailleul²,

Delaveau³

et al. 1985

Planta Med

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“…This research came almost a decade after one of the first studies evidencing, on a scientific basis, the positive effects exerted on human health by olive leaves infusions or decoctions [84]. In the 1970s, Inouye et al used NMR spectroscopy to describe the structures and assign the absolute configurations of oleuropein and of other secoiridoids found in leaves of different plants, namely loganin and nuzhenide (see Figures 2 and 3), opening the way to the first GC-MS systematic investigation on many secoiridoids and iridoid glucosides [85][86][87]. Indeed, 33 secoiridoids and iridoid glucosides present in leaves of Paederia scandes and Lonicera morrowii, plants belonging to the Rubiaceae and Caprifoliaceae families, respectively, were characterized.…”

Section: Olive Leavesmentioning

confidence: 99%

Bioactive Compounds in Waste By-Products from Olive Oil Production: Applications and Structural Characterization by Mass Spectrometry Techniques

Abbattista

Ventura

Calvano

et al. 2021

Foods

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In recent years, a remarkable increase in olive oil consumption has occurred worldwide, favoured by its organoleptic properties and the growing awareness of its health benefits. Currently, olive oil production represents an important economic income for Mediterranean countries, where roughly 98% of the world production is located. Both the cultivation of olive trees and the production of industrial and table olive oil generate huge amounts of solid wastes and dark liquid effluents, including olive leaves and pomace and olive oil mill wastewaters. Besides representing an economic problem for producers, these by-products also pose serious environmental concerns, thus their partial reuse, like that of all agronomical production residues, represents a goal to pursue. This aspect is particularly important since the cited by-products are rich in bioactive compounds, which, once extracted, may represent ingredients with remarkable added value for food, cosmetic and nutraceutical industries. Indeed, they contain considerable amounts of valuable organic acids, carbohydrates, proteins, fibers, and above all, phenolic compounds, that are variably distributed among the different wastes, depending on the employed production process of olive oils and table olives and agronomical practices. Yet, extraction and recovery of bioactive components from selected by-products constitute a critical issue for their rational valorization and detailed identification and quantification are mandatory. The most used analytical methods adopted to identify and quantify bioactive compounds in olive oil by-products are based on the coupling between gas- (GC) or liquid chromatography (LC) and mass spectrometry (MS), with MS being the most useful and successful detection tool for providing structural information. Without derivatization, LC-MS with electrospray (ESI) or atmospheric pressure chemical (APCI) ionization sources has become one of the most relevant and versatile instrumental platforms for identifying phenolic bioactive compounds. In this review, the major LC-MS accomplishments reported in the literature over the last two decades to investigate olive oil processing by-products, specifically olive leaves and pomace and olive oil mill wastewaters, are described, focusing on phenolics and related compounds.

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“…5.-Non obtenu á l'état cristallisé. [ ]20 = +11°(CHCL); uv: X MeOH max nm (log «): 225 (4,2), 278 (4,3); ir: x max cm"1: 1755, 1640, 1510, 1440, 1375; rmn >H (CDCL): : 1,93 k 2,30 (21H, 7s, 7 x OCOCHj), 2,65 (1H, t, _5 = _ = 8 , H-9), 3,25 (1H, td, _8 = _"=8 , -> = 1,5 Hz, H-5), 3,71 (3H, s, COOCH,), 3,73 (1H, m, H-5'), 4,17 (2H, systéme AB dédoublé, H-6'), 4,80 (1H, d, -8=8 , H-l), 4,92 (2H, systéme AB dédoublé, H-10), 4,94 (1H, d, H-l'), 5,05 á 5,23 (3H, 3t, H-2', 3', 4',), 5,74 (1H, dd, J«_5 = 8Hz, JV, = 2Hz, H-6), 6,07 (1H, d, 2Hz, H-7) 6,40 (1H, d, 7ß-=1ß , -ß), 7,20 (1H, d, »-,'=8,5 , H-5"), 7,36 (1H, d, = 2 Hz, H-2"), 7,41 (1H, dd, *-," = 8,5 , "-,»=2 , H-6"), 7,54 (1H, d, _6=1,5 Hz, H-3), 7,63 (1H, d, 7a-d = 16Hz, H-a).…”

Section: Partie Experimentale1mentioning

confidence: 99%

“…Constante physique ([a]) et caractéristiques spectrales (uv, ir, rmn 13C) identiques á celles précédemment décrites (10,11). L'acétylation de 3 foumit le pentaacétylgardénoisde (7) , H-9), 3,60 (1H, m, H-5), 3,71 (3H, s, COOCH,), 4,15 (2H, systéme AB dédoublé, H-10), 5,66 (1H, d, _8=1 Hz, H-l), 5,67 (1H, dd, /,-« = 5,5Hz, _5 = 1,5 Hz, H-7), 6,22 (1H, dd, -, = 5,5 Hz, /«_5=3 , H-6), 7,28 (1H, d, _, = 1 , H-3).…”

Section: Partie Experimentale1unclassified

10-Cafeyl Desacetyldaphylloside Nouvel Iridoide De Randia Formosa

Sainty¹,

Delaveau²,

Bailleul³

et al. 1982

J. Nat. Prod.

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From stem bark of Randia formosa (Rubiaceae) four iridoids are isolated: 10-caffeoyl-deacetyldaphylloside (1), which is a new compound, and feretoside (2), gardenoside (3) and deacetylasperulosidic acid (4), which are already known.Une recherche systématique sur les plantes á iridoides de la flore guyanaise a été entreprise dans le cadre d'une collaboration entre le centre ORSTOM de Cayenne et ce Laboratoire (1). L'étude des écorces de tiges de Randia formosa Schum. (Rubiacées) fait l'objet de la présente publication.Le R. formosa est un arbrisseau inerme á rameaux rigides. Les feuilles, lancéolées, de 2 á 7 cm de long, sont pubescentes á la face inférieure. Les fleurs blanches, terminales, donnent naissance á une bate ovoide (2). Le lot d'écorces de tiges étudié á été récolté á Montjoly (Guyane). Un échantillon d'herbier (CM 1170) est déposé au centre ORSTOM (Cayenne).

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Studies on Monoterpene Glucosides and Related Natural Products. XVII. The Intermediacy of 7-Desoxyloganic Acid and Loganin in the Biosynthesis of Several Iridoid Glucosides

Cited by 22 publications

References 0 publications

Iridoids of Guyanese Species of Stigmaphyllon

Iridoids of Guyanese Species of Stigmaphyllon

Bioactive Compounds in Waste By-Products from Olive Oil Production: Applications and Structural Characterization by Mass Spectrometry Techniques

10-Cafeyl Desacetyldaphylloside Nouvel Iridoide De Randia Formosa

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