Furan fragment isomerized andirobin-type limonoids from the stem barks of <i>Khaya senegalensis</i>

Bu, Yun-Ge; Zhang, Wenyan; Lu, Qinpei; Luo, Jun; Kong, Ling–Yi

doi:10.1080/10286020.2020.1767080

Cited by 3 publications

(2 citation statements)

References 10 publications

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“…Ceramicine J (311) is analog of previously reported ceramicine B 193 except in the substituent variation at C14 and C15. There is an additional hydroxyl and tigloyl group at C11 and C12 respectively in Walsuronoid E (312) when compared to compound (311). Limonoid (313) closely resembles previously reported toosendone 195 but differs in ether linkage between C6/28.…”

Section: Vilasininsupporting

confidence: 83%

Chemistry and Biology of Novel Meliaceae Limonoids

Mulani

Nandikol

Thulasiram

2022

Preprint

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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.

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Section: Vilasininsupporting

confidence: 83%

Chemistry and Biology of Novel Meliaceae Limonoids

Mulani

Nandikol

Thulasiram

2022

Preprint

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“…In the structure of the ring- seco limonoids, in addition to the single ring, can be cracked; there are also cases where the two and even the three rings are cleaved at the same time, such as rings A,B- seco ( B291–B402 ), 60,86,102,107,126,142,155,156,158,182,192–197 rings B,D- seco ( B403–B457 ), 56,85,90,97,135,188,190,198–210 rings A,D- seco ( B458–B481 ), 37,43,127,161,162,211,212 and rings A,B,D- seco ( B482 ) 213 limonoids (Tables S1.8–S1.10†). Different rotations of the C-9/C-10 single bonds of rings A,B- seco limonoids in steric crowding might cause broad or missing NMR signals, which can be solved by building new 1, n -oxygen bridges through biomimetic alkaline hydrolysis.…”

Section: Latest Limonoids Discovered From the Meliaceae Familymentioning

confidence: 99%

Research progress of meliaceous limonoids from 2011 to 2021

Luo

Sun

et al. 2022

Nat. Prod. Rep.

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Isolation and Bioactivities of Limonoids from Meliaceae Family: A Review

Duc

Trung

Thuy

2022

COC

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Limonoids are the most representative metabolites present in the order Rutales, which includes the families Rutaceae, Meliaceae and Cneoraceae. They are tetranortriterpenoids with a 4,4,8-trimethyl-17-furanylsteroidal skeleton, containing several oxygenated functions. The Meliaceae family consists of 50 genera with more than 1400 species distributed in tropical and subtropical regions worldwide. Plants of this family are found to be rich in limonoids. Limonoids from Meliaceae family exhibit a diverse range of bioactivities cytotoxic, antioxidant, anti-inflammatory, antimicrobial, antimalarial, and antifeedant, activities and some of them have been commercially used for different purposes. Numerous studies on limonoids from Meliaceae family and their bioactivities have been reported recently. This review covers the isolation and structure determination of limonoids reported during 2012–2022. 1172 novel limonoids in 118 papers have been summarized. Furthermore, important biological activities of these limonoids have also been outlined. This review can provide useful information for medicinal and pesticidal chemistry and phytochemistry researchers who are interested in the chemistry and biology of limonoids.

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Furan fragment isomerized andirobin-type limonoids from the stem barks of Khaya senegalensis

Cited by 3 publications

References 10 publications

Chemistry and Biology of Novel Meliaceae Limonoids

Chemistry and Biology of Novel Meliaceae Limonoids

Research progress of meliaceous limonoids from 2011 to 2021

Isolation and Bioactivities of Limonoids from Meliaceae Family: A Review

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