Limonoid biosynthesis 3: Functional characterization of crucial genes involved in neem limonoid biosynthesis

Pandreka, Avinash; Chaya, Patil S.; Kumar, Ashish; Aarthy, Thiagarayaselvam; Mulani, Fayaj A.; Bhagyashree, Date D.; B, Shilpashree H.; Cheruvathur, Jennifer; Ponnusamy, Sudha; Nagegowda, Dinesh A.; Thulasiram, Hirekodathakallu V.

doi:10.1016/j.phytochem.2021.112669

Cited by 13 publications

(20 citation statements)

References 49 publications

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“…To confirm the structure of the AaOSC2 product, we scaled up the expression to 17 N. benthamiana plants and isolated the resulting compound by chromatography. NMR analysis confirmed that the AaOSC2 product is tirucalla-7,24-dien-3βol, the same triterpene scaffold that has recently been identified as the key starting point in the biosynthesis of limonoids (Hodgson et al, 2019;Lian et al, 2020;Pandreka et al, 2021). Hence, we rename AaOSC2 as A. altissima tirucalla-7,24-dien-3β-ol synthase (AaTS).…”

Section: Metabolome and Transcriptome Profiling Of Ailanthus Altissim...mentioning

confidence: 66%

“…The Ailanthus altissima oxidosqualene cyclase AaOSC2 is a tirucalla-7,24-dien-3β-ol synthase With the transcriptome data in our hands, we set out to identify the first enzyme of the quassinoid pathway. Based on the structural similarities of quassinoids to limonoids, we anticipated that the first committed step should be catalysed by an oxidosqualene cyclase (OSC) related to tirucalla-7,24-dien-3β-ol synthase from limonoid biosynthesis (Hodgson et al, 2019;Lian et al, 2020;Pandreka et al, 2021). We therefore selected all 22 transcripts encoding oxidosqualene cyclases (sequences provided as Supplementary material) from our transcriptome dataset and generated a phylogenetic tree to enable functional predictions (Figure 3A and Supplementary Figure 1).…”

Section: Metabolome and Transcriptome Profiling Of Ailanthus Altissim...mentioning

confidence: 99%

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Identification of early quassinoid biosynthesis in the invasive tree of heaven (Ailanthus altissima) confirms evolutionary origin from protolimonoids

et al. 2022

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The tree of heaven, Ailanthus altissima (MILL.) SWINGLE, is a globally invasive plant known to secrete allelopathic metabolites called quassinoids. Quassinoids are highly modified triterpenoids. So far, nothing has been known about the biochemical basis of quassinoid biosynthesis. Here, based on transcriptome and metabolome data of Ailanthus altissima, we present the first three steps of quassinoid biosynthesis, which are catalysed by an oxidosqualene cyclase and two cytochrome P450 monooxygenases, resulting in the formation of the protolimonoid melianol. Strikingly, these steps are identical to the first steps of the biosynthesis of limonoids, structurally different triterpenoids from sister plant families within the same order Sapindales. Our results are therefore not only important to fully understand the biosynthesis of complex triterpenoids in plants, but also confirm the long-standing hypothesis that quassinoids and limonoids share an evolutionary origin. In addition, our transcriptome data for Ailanthus altissima will be beneficial to other researchers investigating the physiology and ecology of this invasive tree.

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Section: Metabolome and Transcriptome Profiling Of Ailanthus Altissim...mentioning

confidence: 66%

Section: Metabolome and Transcriptome Profiling Of Ailanthus Altissim...mentioning

confidence: 99%

Identification of early quassinoid biosynthesis in the invasive tree of heaven (Ailanthus altissima) confirms evolutionary origin from protolimonoids

et al. 2022

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“…Cochinchinoid K ( 41) is structurally similar to previously reported 24-epi-melianodiol 43 except at C3 reduction and C21 oxidation. Indicalilacol B (42) is C21 epimer of compound (41). Mesendanin M ( 43) is a C29 hydroxyl derivative of compound (42).…”

Section: Protolimonoid/tirucallanetriterpenoidmentioning

confidence: 99%

“…Indicalilacol B (42) is C21 epimer of compound (41). Mesendanin M ( 43) is a C29 hydroxyl derivative of compound (42). Compound (44) is C21 methylated and C24 acetylated derivative of Melianodiol.…”

Section: Protolimonoid/tirucallanetriterpenoidmentioning

confidence: 99%

“…Over the years with the development of genomic technology and resources, the mystery of limonoid biosynthesis is partially revealed. Very recently through genome mining and transcriptome sequence resources, an oxidosqualene cyclase producing Tirucalla-7,24-dien-3β-ol was identified in different limonoid producing plants like Azadirachta indica 41,42 , Melia azedarach and Citrus sinensis 41 . Also the cytochrome P450 enzymes when coexpressed with this oxidosqualene cyclase produced Dihydroniloticin, Tirucalla-7,24-dien-21,3βdiol and Melianol which are protolimonoids 41 .…”

Section: Introductionmentioning

confidence: 99%

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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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Proteomics Studies Indicate Differential Regulation of Key Metabolism, Energy, and Stress-Responsive Proteins in Azadirachta indica Callus Upon Exposure to Salinity and Jasmonic Acid Treatments

Ashokhan

Karsani

Yaacob

2023

J Plant Growth Regul

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Limonoid biosynthesis 3: Functional characterization of crucial genes involved in neem limonoid biosynthesis

Cited by 13 publications

References 49 publications

Identification of early quassinoid biosynthesis in the invasive tree of heaven (Ailanthus altissima) confirms evolutionary origin from protolimonoids

Identification of early quassinoid biosynthesis in the invasive tree of heaven (Ailanthus altissima) confirms evolutionary origin from protolimonoids

Chemistry and Biology of Novel Meliaceae Limonoids

Proteomics Studies Indicate Differential Regulation of Key Metabolism, Energy, and Stress-Responsive Proteins in Azadirachta indica Callus Upon Exposure to Salinity and Jasmonic Acid Treatments

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