Rearranged limonoids with unique 6/5/6/5 tetracarbocyclic skeletons from Toona ciliata and biomimetic structure divergence

Luo, Jun; Huang, Wansha; Hu, Sheng-Mou; Zhang, Panpan; Zhou, Xu-Wei; Wang, Xiaobing; Yang, Ming‐Hua; Luo, Jian‐Guang; Wang, Chen; Liu, Chang; Yao, Hequan; Zhang, Can; Sun, Hongbin; Chen, Yijun

doi:10.1039/c7qo00678k

Cited by 19 publications

(12 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…More importantly, it is also a medicinal plant as a result of the rich chemical substances in its roots, stems and leaves [3]. Compounds that have been isolated from T. ciliata include ketones, steroids, and coumarins, many of which have antifungal, antiglycation, or anti-tumor activities [4][5][6][7], and its flower extract has a therapeutic effect on gastric ulcers [8]. However, the yield of compounds isolated from T. ciliata is low.…”

Section: Introductionmentioning

confidence: 99%

Selection and validation of reference genes for measuring gene expression in Toona ciliata under different experimental conditions by quantitative real-time PCR analysis

et al. 2020

View full text Add to dashboard Cite

Background Before studying gene expression of different organisms, it is important to determine the best reference gene. At present, the most accurate method of detecting gene expression is quantitative real-time PCR (RT-qPCR). With this method, reference genes that are stable in different biological systems and under different conditions can be obtained. Toona ciliata Roem (T. ciliata). is a valuable and fast-growing timber specie. In this study, 20 reference genes were identified using RT-qPCR, as a primary prerequisite for future gene expression analysis. Four different methods, geNorm, NormFinder, BestKeeper, and RankAggreg were used to evaluate the expression stability of the 20 candidate reference genes in various tissues under different conditions. Results The experimental results showed that TUB-α was the most stably expressed reference gene across all samples and UBC17 was the most stable in leaves and young stems under Hypsipyla robusta (H. robusta) and methyl jasmonate (MeJA) treatments. In addition, PP2C59 and UBC5B were the best-performing genes in leaves under H. robusta treatment, while HIS1 and ACT7 were the best reference genes in young stems. The two best reference genes were 60S-18 and TUB-α after treatment at 4 °C. The expression of HIS6 and MUB1 was the most stable under PEG6000 treatment. The accuracy of the selected reference genes was verified using the transcription factor MYB3 (TcMYB3) gene. Conclusions This is the first report to verify the best reference genes for normalizing gene expression in T. ciliata under different conditions, which will facilitate future elucidation of gene regulations in this species.

show abstract

Section: Introductionmentioning

confidence: 99%

Selection and validation of reference genes for measuring gene expression in Toona ciliata under different experimental conditions by quantitative real-time PCR analysis

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Oxidation of OH-6 generates 2 with a carbonyl at C-6, which can be recognized as the direct precursor of 1 . A vital intermediate carbocation i was produced by an acetolysis of OAc-1 under acid conditions and enol tautomerism of carbonyl at C-6 of 2 , and then, a plausible electrophilic cyclization reaction between C-1 carbocation and electron-rich C-5 may form the unprecedented C1/5/10-cyclopropanen and obtain 1 …”

Section: Results and Discussionmentioning

confidence: 99%

Aglatestine A, a Rearranged Limonoid with a 3/6/6 Tricarbocyclic Framework from the Fruits of Aglaia edulis

et al. 2021

Self Cite

View full text Add to dashboard Cite

Aglatestine A (1), an unprecedented 3/6/6 tricarbocyclic limonoid framework along with four biogenic A/D-seco limonoid analogues with rare β-substituents at C-6 (2−5), was discovered from the fruits of Aglaia edulis. The structures of 1−5 along with their absolute configurations were clarified using methods of HRMS(ESI), NMR, electronic circular dichroism, X-ray diffraction crystallography, and quantum chemical calculations. The plausible biogenetic speculation suggested that an electrophilic cyclization between C-1 carbocation from acetolysis and electron-rich C-5 from enolization of CO of 2 may play a key role. The biological evaluation showed that 5 exhibited anti-inflammatory activity indicated by inhibiting NO release in LPS-activated RAW 264.7 macrophages (IC 50 : 35.72 ± 1.96 μM).

show abstract

“…In compounds (219)(220)(221)(222)(223)(224)(225)(226)(227)(228)(229) there is change in orientation of the γ-lactone ring. The olefinic double bond in substituted tetrahydrofuran ring of compound (230) is hydroxylated in Yunnanol A (231). The C14/15 oxirane and acetyl moiety in compound (201) are absent in Dysoxylumosin M (232) as indicated by NMR spectrum.…”

Section: Cedrelone Classmentioning

confidence: 97%

Chemistry and Biology of Novel Meliaceae Limonoids

Mulani

Nandikol

Thulasiram

2022

Preprint

View full text Add to dashboard Cite

Nature has bestowed us with abundant bioactive/drug molecules for various uses in our everyday life. One such group of plant specialized molecules is limonoids, which are structurally characterized as 4,4,8-trimethyl-17-furanyl steroidal skeleton. Limonoids are well known for their various biological activities such as potent anti-feedent, anti-cancer, anti-inflammatory, insecticidal, anti-diabetic, anti-viral, anti-microbial etc. These tetranortriterpenes are highly oxygenated and structurally diversified molecules majorly found in Meliaceae and Rutaceae and less frequently in the Cneoraceae families in the plant kingdom. Many of these plants have been used in traditional medicine from ages. One of the well-known limonoid, azadirachtin A is highly valued and widely popular for its outstanding insecticidal properties. Till date, nearly 2500 limonoids with over 35 unique carbon frameworks have been observed. In recent times, these molecules have dig a great interest among researchers due to their myriad biological properties. With the advancement of analytical techniques, the limonoid research is aced to explore more different molecules from their sources. In our review we cover all the Meliaceous limonoids isolated during July 2010 to Dec 2020. We found over 1502 new limonoids, which are reported from various Meliaceae plants after Jun 2010. We have classified them based on their skeletal structure rearrangements and functional groups into various classes such as protolimonoids, Apoprotolionoid, Azadirone, Vilasinin, Cedrelone, Havanensin, Trichilin, Nimbin, Salannin, Azadirachtin, Nimbolidin, Nimbolinin, Obacunol, Evodulone, Trijugin, Cipadesin, Andirobin, Mexicanolide, Phragmalin, Khayanolide, Preieurianin, Aphanamixoid, Nor Limonoid and N-containing derivatives. Further we have discussed their biological activities in detail.

show abstract

Rearranged limonoids with unique 6/5/6/5 tetracarbocyclic skeletons from Toona ciliata and biomimetic structure divergence

Abstract: Rearranged limonoids with 6/5/6/5 carbon skeletons, were characterized as metabolite and biomimetic products.

Cited by 19 publications

References 31 publications

Selection and validation of reference genes for measuring gene expression in Toona ciliata under different experimental conditions by quantitative real-time PCR analysis

Selection and validation of reference genes for measuring gene expression in Toona ciliata under different experimental conditions by quantitative real-time PCR analysis

Aglatestine A, a Rearranged Limonoid with a 3/6/6 Tricarbocyclic Framework from the Fruits of Aglaia edulis

Chemistry and Biology of Novel Meliaceae Limonoids

Contact Info

Product

Resources

About