ChemInform Abstract: STICKSTOFFHALTIGE TRITERPENDERIVATE 3. MITT. LUPANDERIVATE 2. MITT.

Ludwiczak, Rufina Stella; Wrzeciono, U.; Szczawińska, K; Mroczkiewicz, Andrzej

doi:10.1002/chin.197144407

Cited by 2 publications

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“…In 1958, LUDWICZAK et al. 9 first isolated inotodiol from Inonotus obliquus, which is an unsaturated diol compound with white needle crystal ( Fig. 1a ).…”

Section: Introductionmentioning

confidence: 99%

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Inotodiol ameliorates the progression of osteoarthritis: An in vitro and in vivo study

Qian,

Ji,

et al. 2023

Drug Res (Stuttg)

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Osteoarthritis is a common chronic degenerative disease, of which the essence is the degenerative changes of bone and joint cartilage, involving damage in multiple structures such as bone, synovium and joints. In the mechanism of arthritis inflammation is closely related, and therefore the exploration to inhibit inflammatory mediators is crucial for the clinical prevention and treatment of osteoarthritis. Inotodiol is a lanostane triterpenoid isolated from Inonotus obliquus, which had been extensively reported to be an anti-inflammatory agent, but its effect on arthritis remains unknown. In this study, we firstly demonstrated that inotodiol significantly reduced IL-1β-induced chondrocyte injury and inhibited the release of inflammatory factors. At the same time, experiments in vivo showed that inotodiol could effectively improve the symptoms of joint injury in mice and reduce the area of cartilage destruction, indicating that inotodiol may be a potential therapeutic drug for osteoarthritis.

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“…In 1958, LUDWICZAK et al. 9 first isolated inotodiol from Inonotus obliquus, which is an unsaturated diol compound with white needle crystal ( Fig. 1a ).…”

Section: Introductionmentioning

confidence: 99%

“…1a ). After 16 years, the chemical structure of inotodiol was determined by chemical degradation and semi-synthesis, and its related physical constants were reported 10 11 12 .…”

Section: Introductionmentioning

confidence: 99%

Inotodiol ameliorates the progression of osteoarthritis: An in vitro and in vivo study

Qian,

Ji,

et al. 2023

Drug Res (Stuttg)

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“…The reaction of lupane derivatives with ozone and dimethyldioxirane has been studied [1,2]. It was shown that oxidation of betulin and its acetates by Cr(VI) oxide produced derivatives with keto-and carboxylic groups [3][4][5][6]. Thus, the formation of epimeric C20-acids from the reaction of betulin diacetate (1) with CrO 3 in acetic acid at 70°C was reported [5].…”

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confidence: 96%

Synthesis and molecular structure of 3β,28-diacetoxy-(20R)-lupan-29-oic acid

2012

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The methyl ester of 3E,28-diacetoxy-(20R)-lupan-29-oic acid was synthesized and its molecular structure was determined.Keywords: betulin, oxidation, 3E,28-diacetoxy-(20R)-lupan-29-oic acid, x-ray structure analysis.Oxidation is an effective method for modifying the isopropenyl group of lupane-type triterpenoids. The reaction of lupane derivatives with ozone and dimethyldioxirane has been studied [1,2]. It was shown that oxidation of betulin and its acetates by Cr(VI) oxide produced derivatives with keto-and carboxylic groups [3][4][5][6]. Thus, the formation of epimeric C20-acids from the reaction of betulin diacetate (1) with CrO 3 in acetic acid at 70°C was reported [5]. On the other hand, the product from the reaction of 1 with CrO 3 was purported to be a norketone (2) [6]. Herein data on the product composition from the oxidation of 1 by CrO 3 in refluxing acetic acid and an x-ray structure analysis (XSA) of one of the acids as the methyl ester are reported.The reaction of 1 and CrO 3 in acetic acid at 100°C for 3 h produced a mixture of the norketone (2) and two epimeric acids (3 and 4), which were isolated pure using column chromatography in yields of 50, 20, and 15%, respectively (Scheme 1). NMR spectra of 3 and 4 were identical. The structure of ketone 2 was confirmed previously by an XSA [7]. Methylation of acid 3 by diazomethane solution gave ester 5. An XSA established its molecular and crystal structure (Fig. 1). All six-membered rings had the chair conformation. The five-membered ring had a slightly distorted envelope conformation. This is usually observed for such compounds [8]. The absolute configuration of 5 was determined from the retention of configuration of the chiral atoms during the reaction (Fig. 1). This suggested that C20 had the R-configuration. According to the XSA of 5, it can be concluded that acids 3 and 4 were the 20R and 20S-epimers.Thus, the structure of the methyl ester of 3E,28-diacetoxy-(20R)-lupan-29-oic acid was determined. Pure (20R)-and (20S)-lupane acids are interesting as a platform for synthesizing triterpenoid derivatives at the C3, C28, and C29 positions.

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ChemInform Abstract: STICKSTOFFHALTIGE TRITERPENDERIVATE 3. MITT. LUPANDERIVATE 2. MITT.

Abstract: Es werden Versuche unternommen, um die Hydroxylgruppe im Aminolupenol (Ia) durch die Aminogruppe zu ersetzen.

Cited by 2 publications

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Inotodiol ameliorates the progression of osteoarthritis: An in vitro and in vivo study

Inotodiol ameliorates the progression of osteoarthritis: An in vitro and in vivo study

Synthesis and molecular structure of 3β,28-diacetoxy-(20R)-lupan-29-oic acid

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