Terpenoids. XXIV.<sup>1</sup> The Structure of the Cactus Triterpene Queretaroic Acid

Djerassi, Carl; Henry, John A.; Lemin, A. J.; Ríos, Tirso; Thomas, Glyn V.

doi:10.1021/ja01596a060

Cited by 33 publications

(9 citation statements)

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“…The aforementioned apparently homogeneous minor reaction product from Sa was a mixture. Its UV spectrum showed four peaks at 242,251,261 and 280nm, among them the former triple peaks suggested the existence of a heteroannular diene system (5) and the latter, a homoannular diene system (11). Evidence from the mass spectral fragmentation patterns also supported the above suggestion.…”

Section: Ho5mentioning

confidence: 52%

“…In general, chemical reactions (4), chemical transformations (5) as well as several spectral data (6,7) have been used for the establishing the presence of a primary hydroxyl group at C-17 or C-20 position of DIE rings of olean-12-enes. However, such chemical reactions and chemical transformations are sometimes very tedious and require large amounts of samples.…”

Section: Introductionmentioning

confidence: 99%

“…The disease can be thought of as producing three main types of abnormalities, namely, anaemia, the sickle cell pain crises, and organ damage. Because of this debilitating effect of the disease, a lot of clinical attempts are being constantly made to at least prophylactically prevent or considerably reduce the occurrence Recently, considerable interest has been shown in the antisickling property of the extracts from the root of Fagara zanthoxyloides (4,5). The possibility of deriving some remedy from medicinal plants is therefore clearly exciting.…”

Section: Introductionmentioning

confidence: 99%

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Cycloetherification of Hydroxyoleanenes byN-Bromosuccinimide

Woo¹,

Kang²,

Jew³

1985

Planta Med

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Treatment of 28-hydroxyolean-12-enes with N-bromosuccinimide (NBS) in acetonitrile at room temperature afforded 12 alpha-bromooleanan-13beta, 28-epoxides in high yield. This reaction resulted in the formation of olean-9 (11), 12-diene-18alpha, 29-epoxides from 29-hydroxy isomers but recovered only starting materials from 30-hydroxy isomers. NBS will be used a reagent for diagnostic tool to distinguish between isomers bearing a primary hydroxyl group on D/E rings of olean-12-enes.

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Section: Ho5mentioning

confidence: 52%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cycloetherification of Hydroxyoleanenes byN-Bromosuccinimide

Woo¹,

Kang²,

Jew³

1985

Planta Med

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“…Abundantly found in nature, Rhizomucor miehei CECT 2749 partially metabolized OA (approximately 0.5 g/L) for 13 days to form of 1β,30-dihydroxy-OA (47), 7β,30-dihydroxy-OA (48), and 30-hydroxy-OA (25) in equivalent amounts (5.0-6.0%) [108]. Compound 25, known as queretaroic acid, was first isolated from Lemaireocereus queretaroensis and L. beneckei endemic to Mexico [109]. This compound was shown to exhibit a moderate antitumor activity against HeLa cells [110].…”

Section: Fungal Transformationmentioning

confidence: 99%

“…Compound 25 , known as queretaroic acid, was first isolated from Lemaireocereus queretaroensis and L . beneckei endemic to Mexico [ 109 ]. This compound was shown to exhibit a moderate antitumor activity against HeLa cells [ 110 ].…”

Section: Biological Transformationmentioning

confidence: 99%

Biotransformation of Oleanane and Ursane Triterpenic Acids

2020

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Oleanane and ursane pentacyclic triterpenoids are secondary metabolites of plants found in various climatic zones and regions. This group of compounds is highly attractive due to their diverse biological properties and possible use as intermediates in the synthesis of new pharmacologically promising substances. By now, their antiviral, anti-inflammatory, antimicrobial, antitumor, and other activities have been confirmed. In the last decade, methods of microbial synthesis of these compounds and their further biotransformation using microorganisms are gaining much popularity. The present review provides clear evidence that industrial microbiology can be a promising way to obtain valuable pharmacologically active compounds in environmentally friendly conditions without processing huge amounts of plant biomass and using hazardous and expensive chemicals. This review summarizes data on distribution, microbial synthesis, and biological activities of native oleanane and ursane triterpenoids. Much emphasis is put on the processes of microbial transformation of selected oleanane and ursane pentacyclic triterpenoids and on the bioactivity assessment of the obtained derivatives.

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Weitere Triterpene aus Melissa officinalis L.

Brieskorn¹,

Krause²

1974

Archiv der Pharmazie

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Melissa off. L. enthalt als weitere Triterpene: Pomolsaure, drei 2-Hydroxy-und eine 20-Hydroxytiterpensaure. In der Wurzel kommen Betulindure, Betulin und drei 2-Hydroxytriterpen-sSuren vor. Die Konfiguration der 2,3-Dihydroxytriterpensiuren wird durch Synthese der vier isomeren 2-Hydroxydcrivatc von Olcanolsiure, Ursolsiure und @Arnyrin bewiesen.Further Triterpenes from Melissa officinalis L.Melissa off. contains as further triterpenes pomolic acid, three 2-hydroxy-and one 29-hydroxytriterpenic acid. The root contains betulinic acid, betulin and three 2-hydroxytriterpenic acids.The configuration of the 2,3-dihydroxytriterpnic acids was proved by synthesis of the four isomeric 2-hydroxy-derivatives of oleanolic acid, ursolic acid and cu-amyrin. Brieskorn und Krouse Arch.Pharmaz. Tabelle 1: Fortsetzung Wurzel: Mengenverhaltnis % von Gesamttriterpencn Betulinsiiure 9 3 Betulin 1 2-~-Hydroxyoleanolsiure 2 3 395 24-Hydroxyoleanolsiure 2 2-ct-Hydroxyursolsiiurc 1 Die Identifizierung der Sauren erfolgte uber lhre Methylester. In den oberirdischen Pflanzenteilen machen Oleanol-und Ursolsaure mit 94 7% der Gesamttriterpene und im Verhaltnis 1 : 4 den Hauptanteil aus. In der Wurzel sind beide Sauren nicht enthalten. Hier uberwiegt die dem Lupantyp zugehorende Betulindure. Die in den oberirdischen Pflanzenteilen enthaltene 29-Hydroxyoleanoldure ( l ) , bisher nur als Bestandteil eines Cacteen-Saponins beschrieben3), liegt in Melisse als Aglykon vor. Das Massenspektrum von l a zeigt einen Molekiilpeak bei m/e 486 und eine fur A"-Triterpene typische RDA-Spaltung des Ringes C4) mit den Fragmenten m/e 278 und 207. Der Base-peak m/e 247 spricht fur die Abspaltung einer Hydroxymethylgruppe aus m/e 278. Das NMR-Spektrum beweist die Olean-12-en-struktur. Das vinylische Proton erscheint als Triplett bei 5,31 ppm. Das Singulett bei 3,28 ppm mit der Intensitat von 2 H und das Auftreten von nur 6 Signalen fur tertiare Methylgruppen bestatigen eine CH2 OH-Gruppe. Die Lage der hochsten Methylgruppe bei 0,71 ppm beweist nach Shammas einen C-17-Methylester. Fiir die primare alkoho lische OH Gruppe bleiben somit nur die Positionen C-29 und C-306'. Alle ermittelten Werte stimmen mit der von 7'ursch3) beschriebenen 29-Hydroxyoleanol~ure uberein.Pomoldure (19a-Hydroxyursoldure) scheint uberall dort voaukommen, wo Oleanol-und Ursoldure vorliegen. So konnte sie auch bereits in mehreren Labiaten nachgewiesen werden').2a-Hydroxyoleanoldure und 2a-Hydroxyursoldure sind in den oberirdischen Pflanzenteilen und, trotz des Fehlens von Oleanol-und Ursoldure, auch in der Wurzel enthalten. 2~-Hydroxyoleanolsaure, die in der Wurzel reichlich, in den oberirdischen Pflanzenteilen nur in Spuren vorkommt, haben wir bereits friiher im Blatt von 3 B. Tursch, J. Leclerg und G. Chiurdoglu, Tetrahedron Letters (London) 1965, 4161.

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Terpenoids. XXIV.¹ The Structure of the Cactus Triterpene Queretaroic Acid

Cited by 33 publications

References 0 publications

Cycloetherification of Hydroxyoleanenes byN-Bromosuccinimide

Cycloetherification of Hydroxyoleanenes byN-Bromosuccinimide

Biotransformation of Oleanane and Ursane Triterpenic Acids

Weitere Triterpene aus Melissa officinalis L.

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Terpenoids. XXIV.1 The Structure of the Cactus Triterpene Queretaroic Acid

Cited by 33 publications

References 0 publications

Cycloetherification of Hydroxyoleanenes byN-Bromosuccinimide

Cycloetherification of Hydroxyoleanenes byN-Bromosuccinimide

Biotransformation of Oleanane and Ursane Triterpenic Acids

Weitere Triterpene aus Melissa officinalis L.

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Product

Resources

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Terpenoids. XXIV.¹ The Structure of the Cactus Triterpene Queretaroic Acid