Practical Synthesis of α‐Amyrin, β‐Amyrin, and Lupeol: The Potential Natural Inhibitors of Human Oxidosqualene Cyclase

Chen, Dongyin; Xu, Fengguo; Zhang, Pu; Deng, Jie; Sun, Hongbin; Wen, Xiaoan; Li, Jun

doi:10.1002/ardp.201700178

Cited by 12 publications

(8 citation statements)

References 33 publications

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“…Therefore, over three steps, we were able to convert oleanolic acid to β-amyrin in an 81% overall yield. This represents a good improvement to the previously reported 42% [ 19 ]. Unfortunately, this approach did not work with ursolic acid; due to its limited reactivity on C-28, the substitution reaction with iodine at C-28 did not proceed well.…”

Section: Resultssupporting

confidence: 73%

“…This approach yielded α-amyrin in 64% overall yield, while β-amyrin was formed in around 69% overall yield. The latter yield is a significant improvement to known procedures for the synthesis of β-amyrin [ 19 ]. Upon scaling up of the reactions by a factor of 5, the overall yield drops slightly (62 and 66%, respectively).…”

Section: Resultsmentioning

confidence: 99%

“…Until now, there has been no publication describing the total synthesis of α-amyrin. A recent partial synthesis, starting from easily accessible starting materials—oleanolic acid ( OA ) and ursolic acid ( UA )—made α-amyrin, β-amyrin, and lupeol accessible [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

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An Improved Scalable Synthesis of α- and β-Amyrin

Serbian

Csuk

2018

Molecules

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Section: Resultssupporting

confidence: 73%

Section: Resultsmentioning

confidence: 99%

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An Improved Scalable Synthesis of α- and β-Amyrin

Serbian

Csuk

2018

Molecules

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“…R. tomentosa has been reported to contain various phytochemical compositions in many parts of the plant (Table 1). Earlier, Hui and colleagues isolated several triterpenoids from R. tomentosa leaves including lupeol, β-amyrin, β-amyrenonol, and botulin [7] that have potential inhibitory activity against human oxidosqualene cyclase [8]. The repetition of an investigation of the petrol extracts of R. tomentosa led to the isolation of the new triterpenoid, 3β-hydroxy-21α-hop-22(29)-en-30-al [9].…”

Section: Phytochemical Compositionmentioning

confidence: 99%

The Health Beneficial Properties of Rhodomyrtus tomentosa as Potential Functional Food

Ngo

2019

Biomolecules

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Rhodomyrtus tomentosa (Aiton) Hassk. is a flowering plant belonging to the family Myrtaceae, native to southern and southeastern Asia. It has been used in traditional Vietnamese, Chinese, and Malaysian medicine for a long time for the treatment of diarrhea, dysentery, gynecopathy, stomachache, and wound healing. Moreover, R. tomentosa is used to make various food products such as wine, tea, and jam. Notably, R. tomentosa has been known to contain structurally diverse and biologically active metabolites, thus serving as a potential resource for exploring novel functional agents. Up to now, numerous phenolic and terpenoid compounds from the leaves, root, or fruits of R. tomentosa have been identified, and their biological activities such as antioxidant, antibacterial, anti-inflammatory, and anticancer have been evidenced. In this contribution, an overview of R. tomentosa and its health beneficial properties was focused on and emphasized.

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“…Phytosterols are known to decrease LDL-cholesterol concentrations and inflammatory responses . Amyrins reduce biosynthesis of cholesterol and have hepatoprotective, anti-hyperglycemic, and hypolipidemic activity . Policosanol, tocopherol, and sterol composition in milk thistle (Silybum marianum L.) seed oils, and tocopherol contents in Onopordum acanthium seeds have been analyzed previously, but the secondary metabolites in different organs of C.…”

Section: Resultsmentioning

confidence: 63%

Integrated Analysis of Transcriptome and Metabolome in Cirsium japonicum Fisch ex DC

et al. 2020

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Cirsium japonicum Fisch ex DC belongs to the Compositae family and has been used as a folk remedy source in Asian countries because of its health-promoting properties. It is known that C. japonicum contains flavonoids, furans, long-chain alcohols, sterols, and volatile oils. Nevertheless, the molecular mechanism of secondary metabolite biosynthesis remains poorly understood. Therefore, transcriptome analysis and metabolic profiling were performed using different parts of C. japonicum to investigate phenylpropanoid metabolism. Based on the BLASTX search results, we identified 29 orthologs of enzymes responsible for phenylpropanoid biosynthesis. Additionally, 75 metabolites were identified in C. japonicum. Most of the flavonoid biosynthetic genes were significantly expressed ranging from 2.6-to 500-fold higher in the flowers than those in the leaves. Correspondently, the total content of flavonols was 21-fold higher in the flowers than in the roots. However, the total level of flavones showed 58-fold higher amounts in the leaves than in the flowers. Additionally, the total content of flavanols was 19-fold higher in the leaves than in the roots. The results of this study provide transcriptomic and metabolic information to elucidate the tissue-specific phenylpropanoid metabolism of C. japonicum.

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Practical Synthesis of α‐Amyrin, β‐Amyrin, and Lupeol: The Potential Natural Inhibitors of Human Oxidosqualene Cyclase

Cited by 12 publications

References 33 publications

An Improved Scalable Synthesis of α- and β-Amyrin

An Improved Scalable Synthesis of α- and β-Amyrin

The Health Beneficial Properties of Rhodomyrtus tomentosa as Potential Functional Food

Integrated Analysis of Transcriptome and Metabolome in Cirsium japonicum Fisch ex DC

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