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Journal articles on the topic 'Limonoid Biosynthesis'

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Author: Grafiati

Published: 6 September 2023

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1

De La Peña, Ricardo, Hannah Hodgson, Jack Chun-Ting Liu, Michael J. Stephenson, Azahara C. Martin, Charlotte Owen, Alex Harkess, et al. "Complex scaffold remodeling in plant triterpene biosynthesis." Science 379, no. 6630 (January 27, 2023): 361–68. http://dx.doi.org/10.1126/science.adf1017.

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Triterpenes with complex scaffold modifications are widespread in the plant kingdom. Limonoids are an exemplary family that are responsible for the bitter taste in citrus (e.g., limonin) and the active constituents of neem oil, a widely used bioinsecticide (e.g., azadirachtin). Despite the commercial value of limonoids, a complete biosynthetic route has not been described. We report the discovery of 22 enzymes, including a pair of neofunctionalized sterol isomerases, that catalyze 12 distinct reactions in the total biosynthesis of kihadalactone A and azadirone, products that bear the signature limonoid furan. These results enable access to valuable limonoids and provide a template for discovery and reconstitution of triterpene biosynthetic pathways in plants that require multiple skeletal rearrangements and oxidations.

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2

Hodgson, Hannah, Ricardo De La Peña, Michael J. Stephenson, Ramesha Thimmappa, Jason L. Vincent, Elizabeth S. Sattely, and Anne Osbourn. "Identification of key enzymes responsible for protolimonoid biosynthesis in plants: Opening the door to azadirachtin production." Proceedings of the National Academy of Sciences 116, no. 34 (August 1, 2019): 17096–104. http://dx.doi.org/10.1073/pnas.1906083116.

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Limonoids are natural products made by plants belonging to the Meliaceae (Mahogany) and Rutaceae (Citrus) families. They are well known for their insecticidal activity, contribution to bitterness in citrus fruits, and potential pharmaceutical properties. The best known limonoid insecticide is azadirachtin, produced by the neem tree (Azadirachta indica). Despite intensive investigation of limonoids over the last half century, the route of limonoid biosynthesis remains unknown. Limonoids are classified as tetranortriterpenes because the prototypical 26-carbon limonoid scaffold is postulated to be formed from a 30-carbon triterpene scaffold by loss of 4 carbons with associated furan ring formation, by an as yet unknown mechanism. Here we have mined genome and transcriptome sequence resources for 3 diverse limonoid-producing species (A. indica, Melia azedarach, and Citrus sinensis) to elucidate the early steps in limonoid biosynthesis. We identify an oxidosqualene cyclase able to produce the potential 30-carbon triterpene scaffold precursor tirucalla-7,24-dien-3β-ol from each of the 3 species. We further identify coexpressed cytochrome P450 enzymes from M. azedarach (MaCYP71CD2 and MaCYP71BQ5) and C. sinensis (CsCYP71CD1 and CsCYP71BQ4) that are capable of 3 oxidations of tirucalla-7,24-dien-3β-ol, resulting in spontaneous hemiacetal ring formation and the production of the protolimonoid melianol. Our work reports the characterization of protolimonoid biosynthetic enzymes from different plant species and supports the notion of pathway conservation between both plant families. It further paves the way for engineering crop plants with enhanced insect resistance and producing high-value limonoids for pharmaceutical and other applications by expression in heterologous hosts.

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3

Pandreka, Avinash, Patil S. Chaya, Ashish Kumar, Thiagarayaselvam Aarthy, Fayaj A. Mulani, Date D. Bhagyashree, Shilpashree H. B, et al. "Limonoid biosynthesis 3: Functional characterization of crucial genes involved in neem limonoid biosynthesis." Phytochemistry 184 (April 2021): 112669. http://dx.doi.org/10.1016/j.phytochem.2021.112669.

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4

Herman, Zareb, Chi H. Fong, and Shin Hasegawa. "Biosynthesis of limonoid glucosides in navel orange." Phytochemistry 30, no. 5 (January 1991): 1487–88. http://dx.doi.org/10.1016/0031-9422(91)84193-v.

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5

Pandreka, Avinash, Patil S. Chaya, Ashish Kumar, Thiagarayaselvam Aarthy, Fayaj A. Mulani, Date D. Bhagyashree, H. B. Shilpashree, et al. "Corrigendum to “Limonoid biosynthesis 3: Functional characterization of crucial genes involved in neem limonoid biosynthesis” [Phytochemistry 184 (2021) 112669]." Phytochemistry 187 (July 2021): 112751. http://dx.doi.org/10.1016/j.phytochem.2021.112751.

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6

Fong, Chi H., Shin Hasegawa, Zareb Herman, and Peter Ou. "Biosynthesis of limonoid glucosides in lemon (Citrus limon)." Journal of the Science of Food and Agriculture 54, no. 3 (1991): 393–98. http://dx.doi.org/10.1002/jsfa.2740540310.

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7

Ou, Peter, Shin Hasegawa, Zareb Herman, and Chi H. Fong. "Limonoid biosynthesis in the stem of Citrus limon." Phytochemistry 27, no. 1 (1988): 115–18. http://dx.doi.org/10.1016/0031-9422(88)80600-9.

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8

Liu, Cuihua, Min He, Zhuang Wang, and Juan Xu. "Integrative Analysis of Terpenoid Profiles and Hormones from Fruits of Red-Flesh Citrus Mutants and Their Wild Types." Molecules 24, no. 19 (September 23, 2019): 3456. http://dx.doi.org/10.3390/molecules24193456.

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In citrus color mutants, the levels of carotenoid constituents and other secondary metabolites are different in their corresponding wild types. Terpenoids are closely related to coloration, bitterness, and flavor. In this study, terpenoid profiles and hormones in citrus fruits of two red-flesh mutants—Red Anliu orange and Red-flesh Guanxi pummelo—and their corresponding wild types were investigated using GC/MS, HPLC, and LC-MS/MS. Results showed that Red Anliu orange (high in carotenoids) and Anliu orange (low in carotenoids) accumulated low levels of limonoid aglycones but high levels of monoterpenoids; conversely, Red-flesh Guanxi pummelo (high in carotenoids) and Guanxi pummelo (deficient in carotenoids) accumulated high levels of limonoid aglycones but low levels of monoterpenoids. However, isopentenyl diphosphate was present at similar levels. A correlation analysis indicated that jasmonic and salicylic acids might play important roles in regulating terpenoid biosynthesis. Additionally, the similarities of carotenoid and volatile profiles between each mutant and its corresponding wild type were greater than those between the two mutants or the two wild types. The flux balance of terpenoid metabolism in citrus fruit tends toward stability among various citrus genera that have different terpenoid profiles. Bud mutations could influence metabolite profiles of citrus fruit to a limited extent.

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9

Hullin-Matsuda, Françoise, Nario Tomishige, Shota Sakai, Reiko Ishitsuka, Kumiko Ishii, Asami Makino, Peter Greimel, et al. "Limonoid Compounds Inhibit Sphingomyelin Biosynthesis by Preventing CERT Protein-dependent Extraction of Ceramides from the Endoplasmic Reticulum." Journal of Biological Chemistry 287, no. 29 (May 7, 2012): 24397–411. http://dx.doi.org/10.1074/jbc.m112.344432.

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10

Li, Wanshan, Li Shen, Torsten Bruhn, Patchara Pedpradab, Jun Wu, and Gerhard Bringmann. "Trangmolins A-F with an Unprecedented Structural Plasticity of the Rings A and B: New Insight into Limonoid Biosynthesis." Chemistry - A European Journal 22, no. 33 (July 7, 2016): 11719–27. http://dx.doi.org/10.1002/chem.201602230.

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11

Li, Wan-Shan, Attila Mándi, Jun-Jun Liu, Li Shen, Tibor Kurtán, and Jun Wu. "Xylomolones A–D from the Thai Mangrove Xylocarpus moluccensis: Assignment of Absolute Stereostructures and Unveiling a Convergent Strategy for Limonoid Biosynthesis." Journal of Organic Chemistry 84, no. 5 (February 5, 2019): 2596–606. http://dx.doi.org/10.1021/acs.joc.8b03037.

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12

Tsamo, Armelle Tontsa, Julio Issah Mawouma Pagna, Pamela Kemda Nangmo, Pierre Mkounga, Hartmut Laatsch, and Augustin Ephrem Nkengfack. "Rubescins F–H, new vilasinin-type limonoids from the leaves of Trichilia rubescens (Meliaceae)." Zeitschrift für Naturforschung C 74, no. 7-8 (July 26, 2019): 175–82. http://dx.doi.org/10.1515/znc-2018-0187.

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Abstract Three new limonoids, designated as rubescins F (1), G (2), and H (3), together with two known compounds of this type, TS1 (4) and trichirubine A (5), were isolated from methylene chloride/methanol extracts of Trichilia rubescens leaves. The structures of these compounds were elucidated based on 1D and 2D nuclear magnetic resonance (NMR) analysis and complemented by electrospray ionization high-resolution mass spectrometry results and by comparison to data of related compounds described in the literature and ab initio calculations. Rubescin F (1) is the first limonoid from Trichilia spp. with an oxetane ring between C-7 and C-14, which seems to be formed by the isomerization of TS1 (4). The γ-hydroxybutenolide rubescin G (2) is a potential precursor of trichirubine A (5), whereas rubescin H (3) is the first example of a triterpenoid with a single bond between C-7/C-14, forming a cyclopropane ring. The absolute configuration of these limonoids was derived from biosynthetic considerations and ab initio calculations of NMR and optical rotation dispersion data.

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13

Narender, Tadigoppula, Tanvir Khaliq, Shweta, Kancharla P. Reddy, and Ravi K. Sharma. "Occurrence, Biosynthesis, Biological activity and NMR Spectroscopy of D and B, D Ring Seco-limonoids of Meliaceae Family." Natural Product Communications 2, no. 2 (February 2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200219.

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Limonoids are modified tetranortriterpenoids, classified on the basis of which of the four rings (A, B, C and D) in the intact triterpene nucleus have been oxidized. The order Rutales produces a variety of seco-limonoids, such as A, B, C, D, AB, AD, and BD-ring seco-limonoids. The Meliaceae family, belonging to the order Rutales, has yielded several D-ring and B, D-ring seco-limonoids This review describes the occurrence, biosynthesis, biological activity and NMR spectroscopy of D ring seco-limonoids, such as gedunin derivatives and B, D-ring seco-limonoids, such as methyl angolensates, xyloccensins, methyl meliacates, phragmalins and modified phragmalins. The literature from 1990 to 2005 is reviewed.

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14

Hashinaga, Fumio, Chi H. Fong, and Shin Hasegawa. "Biosynthesis of Limonoids inCitrus sudachi." Agricultural and Biological Chemistry 54, no. 11 (November 1990): 3019–20. http://dx.doi.org/10.1080/00021369.1990.10870416.

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15

HASHINAGA, Fumio, Chi H. FONG, and Shin HASEGAWA. "Biosynthesis of limonoids in Citrus sudachi." Agricultural and Biological Chemistry 54, no. 11 (1990): 3019–20. http://dx.doi.org/10.1271/bbb1961.54.3019.

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16

Hasegawa, Shin, Zareb Herman, Ed Orme, and Peter Ou. "Biosynthesis of limonoids in Citrus: Sites and translocation." Phytochemistry 25, no. 12 (January 1986): 2783–85. http://dx.doi.org/10.1016/s0031-9422(00)83741-3.

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17

Jin, Jie, Xinhuang Lv, Ben Wang, Chenghao Ren, Jingtao Jiang, Hongyu Chen, Ximiao Chen, et al. "Limonin Inhibits IL-1β-Induced Inflammation and Catabolism in Chondrocytes and Ameliorates Osteoarthritis by Activating Nrf2." Oxidative Medicine and Cellular Longevity 2021 (November 9, 2021): 1–15. http://dx.doi.org/10.1155/2021/7292512.

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Osteoarthritis (OA), a degenerative disorder, is considered to be one of the most common forms of arthritis. Limonin (Lim) is extracted from lemons and other citrus fruits. Limonin has been reported to have anti-inflammatory effects, while inflammation is a major cause of OA; thus, we propose that limonin may have a therapeutic effect on OA. In this study, the therapeutic effect of limonin on OA was assessed in chondrocytes in vitro in IL-1β induced OA and in the destabilization of the medial meniscus (DMM) mice in vivo. The Nrf2/HO-1/NF-κB signaling pathway was evaluated to illustrate the working mechanism of limonin on OA in chondrocytes. In this study, it was found that limonin can reduce the level of IL-1β induced proinflammatory cytokines such as INOS, COX-2, PGE2, NO, TNF-α, and IL-6. Limonin can also diminish the biosynthesis of IL-1β-stimulated chondrogenic catabolic enzymes such as MMP13 and ADAMTS5 in chondrocytes. The research on the mechanism study demonstrated that limonin exerts its protective effect on OA through the Nrf2/HO-1/NF-κB signaling pathway. Taken together, the present study shows that limonin may activate the Nrf2/HO-1/NF-κB pathway to alleviate OA, making it a candidate therapeutic agent for OA.

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18

Hasegawa, Shin, and Zareb Herman. "Biosynthesis of limonoids: Conversion of deacetylnomilinate to nomilin in Citrus limon." Phytochemistry 25, no. 11 (January 1986): 2523–24. http://dx.doi.org/10.1016/s0031-9422(00)84500-8.

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19

Rodríguez Ceraolo, Cecilia, Valeria Vázquez, Ignacio Migues, María Verónica Cesio, Fernando Rivas, and Horacio Heinzen. "Flavonoids and Limonoids Profiles Variation in Leaves from Mandarin Cultivars and Its Relationship with Alternate Bearing." Agronomy 12, no. 1 (January 4, 2022): 121. http://dx.doi.org/10.3390/agronomy12010121.

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Alternate bearing in citrus trees has been extensively studied as a key feature for citrus growers. Although the genetic and the biochemical process occurring during alternate bearing has been studied extensively, there is a lack of information identifying the presence of metabolic indicators during “on” and “off” years. In citrus plants, leaves play a central role in the metabolic pathway triggering the flowering induction process. To investigate the changes during this transition, a liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS) analysis of the leaf profiles of 20 compounds (17 polyphenols, two limonoids, and one furanocoumarin), in bearing and non-bearing branches arising from four different mandarin genotypes, was performed. The same metabolites were found in all the genotypes at both stages: both limonoids and 11 polyphenols. Using these compounds, the chemotaxonomic differentiation between cultivars was assessed. The levels of flavanones and limonoids showed differences in both bearing stages and the transition from vegetative to flowering could be shown by the activation of the polyphenol biosynthetic pathway, from precursors like naringenin to metabolic end-points such as narirutin and polymethoxyflavones. Narirutin levels showed significant differences between both stages, suggesting it as a possible marker of the physiological status of the branch.

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20

Herman, Z. "Limonin biosynthesis from obacunone via obacunoate in Citrus limon." Phytochemistry 23, no. 12 (November 26, 1985): 2911–13. http://dx.doi.org/10.1016/s0031-9422(00)80603-2.

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21

Herman, Zareb, and Shin Hasegawa. "Limonin biosynthesis from obacunone via obacunoate in Citrus limon." Phytochemistry 24, no. 12 (November 1985): 2911–13. http://dx.doi.org/10.1016/0031-9422(85)80025-x.

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22

Hu, Wei-Min, and Jun Wu. "Protoxylogranatin B, a Key Biosynthetic Intermediate from Xylocarpus granatum: Suggesting an Oxidative Cleavage Biogenetic Pathway to Limonoid." Open Natural Products Journal 3, no. 1 (February 1, 2010): 1–5. http://dx.doi.org/10.2174/1874848101003010001.

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23

Izumi, Yuriko, Eri Kamei, Yoko Miyamoto, Kouhei Ohtani, Akira Masunaka, Takeshi Fukumoto, Kenji Gomi, et al. "Role of the Pathotype-Specific ACRTS1 Gene Encoding a Hydroxylase Involved in the Biosynthesis of Host-Selective ACR-Toxin in the Rough Lemon Pathotype of Alternaria alternata." Phytopathology® 102, no. 8 (August 2012): 741–48. http://dx.doi.org/10.1094/phyto-02-12-0021-r.

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The rough lemon pathotype of Alternaria alternata produces host-selective ACR-toxin and causes Alternaria leaf spot disease of the rootstock species rough lemon (Citrus jambhiri) and Rangpur lime (C. limonia). Genes controlling toxin production were localized to a 1.5-Mb chromosome carrying the ACR-toxin biosynthesis gene cluster (ACRT) in the genome of the rough lemon pathotype. A genomic BAC clone containing a portion of the ACRT cluster was sequenced which allowed identification of three open reading frames present only in the genomes of ACR-toxin producing isolates. We studied the functional role of one of these open reading frames, ACRTS1 encoding a putative hydroxylase, in ACR-toxin production by homologous recombination-mediated gene disruption. There are at least three copies of ACRTS1 gene in the genome and disruption of two copies of this gene significantly reduced ACR-toxin production as well as pathogenicity; however, transcription of ACRTS1 and production of ACR-toxin were not completely eliminated due to remaining functional copies of the gene. RNA-silencing was used to knock down the remaining ACRTS1 transcripts to levels undetectable by reverse transcription-polymerase chain reaction. The silenced transformants did not produce detectable ACR-toxin and were not pathogenic. These results indicate that ACRTS1 is an essential gene in ACR-toxin biosynthesis in the rough lemon pathotype of A. alternata and is required for full virulence of this fungus.

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24

Vasquez‐Ruiz, Vianey, M. Ángeles Ramírez‐Cisneros, and Maria Yolanda Rios. "Triterpenes and limonoids of Cedrela : Distribution, biosynthesis, and ¹ H and ¹³ C NMR data." Magnetic Resonance in Chemistry 60, no. 3 (November 21, 2021): 275–358. http://dx.doi.org/10.1002/mrc.5229.

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25

Villa-Ruano, Nemesio, Luis Ángel Morales-Mora, Jenaro Leocadio Varela-Caselis, Antonio Rivera, María de los Ángeles Valencia de Ita, and Omar Romero-Arenas. "Arcopilus aureus MaC7A as a New Source of Resveratrol: Assessment of Amino Acid Precursors, Volatiles, and Fungal Enzymes for Boosting Resveratrol Production in Batch Cultures." Applied Sciences 11, no. 10 (May 18, 2021): 4583. http://dx.doi.org/10.3390/app11104583.

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The chemical factors that regulate the synthesis of resveratrol (RV) in filamentous fungi are still unknown. This work reports on the RV production by Arcopilus aureus MaC7A under controlled conditions and the effect of amino acid precursors (PHE and TYR), monoterpenes (limonone, camphor, citral, thymol, menthol), and mixtures of hydrolytic enzymes (Glucanex) as elicitors for boosting fungal RV. Batch cultures with variable concentrations of PHE and TYR (50–500 mg L−1) stimulated RV production from 127.9 ± 4.6 to 221.8 ± 5.2 mg L−1 in basic cultures developed in PDB (pH 7) added with 10 g L−1 peptone at 30 °C. Maximum levels of RV and biomass were maintained during days 6–8 under these conditions, whereas a dramatic RV decrease was observed from days 10–12 without any loss of biomass. Among the tested volatiles, citral (50 mg L−1) enhanced RV production until 187.8 ± 2.2 mg L−1 in basic cultures, but better results were obtained with Glucanex (100 mg L−1; 198.3 ± 7.6 mg L−1 RV). Optimized batch cultures containing TYR (200 mg L−1), citral (50 mg L−1), thymol (50 mg L−1), and Glucanex (100 mg L−1) produced up to 237.6 ± 4.7 mg L−1 of RV. Our results suggest that low concentrations of volatiles and mixtures of isoenzymes with β-1, 3 glucanase activity increase the biosynthesis of fungal RV produced by A. aureus MaC7A in batch cultures.

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26

"Citrus Limonoid Glucosyltransferase: AKey Player For Natural Debittering And Anticancerous Potential." Archives of Life Science and Nurtitional Research, November 28, 2017, 1–16. http://dx.doi.org/10.31829/2765-8368/alsnr2017-1(1)-101.

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Citrus fruits and juices are rich source of health benefitting phytochemicals which play a vital role in balanced diet and disease prevention. Citrus limonoids and flavonoids are the major phytochemicals which are of great interest in pharmaceutical industries because of their demonstrated anticancerous, antioxidant, anti-inflammatory, hormonal stimulation, antibacterial and antiviral actions. Citrus limonoid biosynthetic pathway contains an important regulatory limonoid glucosyltransferase enzyme (LGT). LGT is the natural debittering enzyme encoded by a single copy gene which has been isolated from different Citrus spp. This enzyme is mainly responsible for conversion of all limonoid aglycones (mostly bitter) to their corresponding glucosides (mostly nonbitter) but only during late fruit developmental stage of citrus. Citrus LGT belongs to glycosyltransferase super family whose members are the wide managers to catalyze the transfer of sugar molecules to their acceptor molecules to play several key modifications in plant secondary metabolites. These reveal great significance value in plant cell metabolism especially in detoxification of xenobiotics, production and storage of natural products. Despite to the fact that over expression of LGT in citrus will lead to reduce the delayed bitterness caused by limonin (an aglycone) but in addition will enhance the accumulation of limonoid glucosides in fruits. Further, recent studies suggest that citrus limonoids especially glucosides have shown importance against brain, pancreas, colon, and breast cancers. Thus, future studies should be focused on utilizing the potential of LGT present in citrus plants in terms of anticancerous properties as well as reducing the delayed bitterness problem important for citrus juice industry

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27

Yu, Fang, Babu Gajendran, Ning Wang, Klarke M. Sample, Wuling Liu, Chunlin Wang, Anling Hu, Eldad Zacksenhaus, Xiaojiang Hao, and Yaacov Ben-David. "ERK activation via A1542/3 limonoids attenuates erythroleukemia through transcriptional stimulation of cholesterol biosynthesis genes." BMC Cancer 21, no. 1 (June 9, 2021). http://dx.doi.org/10.1186/s12885-021-08402-6.

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Abstract Background Cholesterol plays vital roles in human physiology; abnormal levels have deleterious pathological consequences. In cancer, elevated or reduced expression of cholesterol biosynthesis is associated with good or poor prognosis, but the underlying mechanisms are largely unknown. The limonoid compounds A1542 and A1543 stimulate ERK/MAPK by direct binding, leading to leukemic cell death and suppression of leukemia in mouse models. In this study, we investigated the downstream consequences of these ERK/MAPK agonists in leukemic cells. Methods We employed RNAseq analysis combined with Q-RT-PCR, western blot and bioinformatics to identify and confirm genes whose expression was altered by A1542 and A1543 in leukemic cells. ShRNA lentiviruses were used to silence gene expression. Cell culture and an animal model (BALB/c) of erythroleukemia induced by Friend virus were utilized to validate effects of cholesterol on leukemia progression. Results RNAseq analysis of A1542-treated cells revealed the induction of all 18 genes implicated in cholesterol biosynthesis. Expression of these cholesterol genes was blocked by cedrelone, an ERK inhibitor. The cholesterol inhibitor lovastatin diminished ERK/MAPK activation by A1542, thereby reducing leukemic cell death induced by this ERK1/2 agonist. Growth inhibition by cholesterol was observed both at the intracellular level, and when orally administrated into a leukemic mouse model. Both HDL and LDL also suppressed leukemogenesis, implicating these lipids as important prognostic markers for leukemia progression. Mechanistically, knockdown experiments revealed that the activation of SREBP1/2 by A1542-A1543 was responsible for induction of only a sub-set of cholesterol biosynthesis genes. Induction of other regulatory factors by A1542-A1543 including EGR1, AP1 (FOS + JUN) LDLR, IER2 and others may cooperate with SREBP1/2 to induce cholesterol genes. Indeed, pharmacological inhibition of AP1 significantly inhibited cholesterol gene expression induced by A1542. In addition to leukemia, high expression of cholesterol biosynthesis genes was found to correlate with better prognosis in renal cancer. Conclusions This study demonstrates that ERK1/2 agonists suppress leukemia and possibly other types of cancer through transcriptional stimulation of cholesterol biosynthesis genes.

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28

Chuang, Ling, Shenyu Liu, Dave Biedermann, and Jakob Franke. "Identification of early quassinoid biosynthesis in the invasive tree of heaven (Ailanthus altissima) confirms evolutionary origin from protolimonoids." Frontiers in Plant Science 13 (August 23, 2022). http://dx.doi.org/10.3389/fpls.2022.958138.

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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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Zhang, Pan, Xiaofeng Liu, Xin Yu, Fusheng Wang, Junhong Long, Wanxia Shen, Dong Jiang, and Xiaochun Zhao. "The MYB transcription factor CiMYB42 regulates limonoids biosynthesis in citrus." BMC Plant Biology 20, no. 1 (June 3, 2020). http://dx.doi.org/10.1186/s12870-020-02475-4.

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30

Cui, Gaofeng, Yun Li, Xin Yi, Jieyu Wang, Peifan Lin, Cui Lu, Qunjie Zhang, Lizhi Gao, and Guohua Zhong. "Meliaceae genomes provide insights into wood development and limonoids biosynthesis." Plant Biotechnology Journal, December 2022. http://dx.doi.org/10.1111/pbi.13973.

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31

Zhang, Pan, Xiaofeng Liu, Xin Yu, Fusheng Wang, Junhong Long, Wanxia Shen, Dong Jiang, and Xiaochun Zhao. "Correction to: The MYB transcription factor CiMYB42 regulates limonoids biosynthesis in citrus." BMC Plant Biology 20, no. 1 (July 6, 2020). http://dx.doi.org/10.1186/s12870-020-02491-4.

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32

Wang, Fusheng, Mei Wang, Xiaona Liu, Yuanyuan Xu, Shiping Zhu, Wanxia Shen, and Xiaochun Zhao. "Identification of Putative Genes Involved in Limonoids Biosynthesis in Citrus by Comparative Transcriptomic Analysis." Frontiers in Plant Science 8 (May 12, 2017). http://dx.doi.org/10.3389/fpls.2017.00782.

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33

Aarthy, Thiagarayaselvam, Fayaj A. Mulani, Avinash Pandreka, Ashish Kumar, Sharvani S. Nandikol, Saikat Haldar, and Hirekodathakallu V. Thulasiram. "Tracing the biosynthetic origin of limonoids and their functional groups through stable isotope labeling and inhibition in neem tree (Azadirachta indica) cell suspension." BMC Plant Biology 18, no. 1 (October 11, 2018). http://dx.doi.org/10.1186/s12870-018-1447-6.

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"Book reviews: Citrus Limonoids: Functional Chemicals in Agriculture and Food, ed. Mark A. Berhow, Shin Hasegawa and Gary D. Manners (reviewed by Robert A. Hill); Biosynthesis: Polyketides and Vitamins, ed. F. J. Leeper and J. C. Vederas (reviewed by Dr Alison Hill); Biosynthesis: Aromatic Polyketides, Isoprenoids and Alkaloids, F. J. Leeper and J. C. Vederas (reviewed by T. J. Simpson); Pharmaceuticals: Classes, Therapeutic Agents, Areas of Application, ed. J. L. McGuire (reviewed by Barrie Wilkinson); Medicinal Plants of the World: Chemical Constituents, Traditional and Modern Medicinal Uses. Vol. 2, Ivan A. Ross (reviewed by Thomas Hemscheidt); Amino Acids, Peptides and Proteins, J. S. Davies (reviewed by Douglas Young); Virtual Screening for Bioactive Molecules, H.-J. Böhm and G. Schneider (reviewed by Dr John B. O. Mitchell); Biologically Active Natural Products: Pharmaceuticals, S. J. Cutler and H. G. Cutler (reviewed by John Mann)." Natural Product Reports 18, no. 3 (2001): 356–60. http://dx.doi.org/10.1039/b103593m.

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