Kadcotriones A–C: Tricyclic Triterpenoids from <i>Kadsura coccinea</i>

Liang, Cheng-Qin; Shi, Yi‐Ming; Li, Xing-Yao; Luo, Rong-Hua; Li, Yan; Zheng, Yong‐Tang; Zhang, Hongbin; Xiao, Wei‐Lie; Sun, Han‐Dong

doi:10.1021/np400546z

Cited by 41 publications

(31 citation statements)

References 19 publications

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“…A plausible biogenetic pathway from an intact lanostane, 12b-hydroxycoccinic acid, to 59 is suggested (Scheme 6). 28 2.1.8 14(13/12)-Abeo-12,13-secolanostane. Kadcotrione C (60), found in the stems of K. coccinea, presents with a 6/6/5-fused ring system that is similar to isomalabaricane-type triterpenoids.…”

Section: Structures Classifications and Distributionsmentioning

confidence: 99%

“…Kadcotrione C (60), found in the stems of K. coccinea, presents with a 6/6/5-fused ring system that is similar to isomalabaricane-type triterpenoids. 28 However, its skeleton is different from that of isomalabaricane due to a unique C 13 side chain and the position of Me-28. Scheme 6 shows that kadcotrione C (60) may arise from a 14(13/12)-abeolanostane-type triterpenoid (intermediate J) via oxidative cleavage.…”

Section: Structures Classifications and Distributionsmentioning

confidence: 99%

“…Therefore, compound 61 is a unique tricyclic bisnortriterpenoid with a C 11 side chain. 28 2.1.10 Schiglautane. Schiglautone A (62) has been isolated from the stems of S. glaucescens and is the rst to feature an exotic 6/7/9-fused tricyclic ring system.…”

Section: Structures Classifications and Distributionsmentioning

confidence: 99%

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Triterpenoids from the Schisandraceae family: an update

et al. 2015

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Several significant advances in the field of phytochemistry were made between 2008 and 2014 because of the high level of interest in Schisandraceae triterpenoids. In addition to a dramatic increase in the number of newly identified triterpenoids, the first complete synthesis of a schinortriterpenoid was accomplished. There has also been substantial progress in investigations of biological activity and mechanism of action. In this update, we review more than 250 new triterpenoids and describe their structures, classifications, biogenetic pathways, syntheses, and bioactivities.

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Section: Structures Classifications and Distributionsmentioning

confidence: 99%

Section: Structures Classifications and Distributionsmentioning

confidence: 99%

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Triterpenoids from the Schisandraceae family: an update

et al. 2015

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“…348 Three tricyclic triterpenoids with unusual skeletons, kadcotriones A 640 -C 642, have been isolated from Kadsura coccinea. 349 Biosynthetic pathways to the kadcotriones, from a common lanostane precursor, have been proposed. The biosynthesis of volvalerenol A 643, from the roots of Valeriana hardwickii, is thought to involve head-to-tail linkages of two units of farnesyl diphosphate.…”

Section: Miscellaneous Compoundsmentioning

confidence: 99%

Triterpenoids

Hill

Connolly

2017

Nat. Prod. Rep.

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“…To date, limonoids of other botanical origin have been described as active against HIV-1 [ 18 – 19 ], dengue virus [ 20 , 21 ], respiratory syncytial virus [ 22 ] and herpes simplex virus [ 23 ]. This is the first report on the antiviral activity of limonoids from M .…”

Section: Introductionmentioning

confidence: 99%

Limonoids from Melia azedarach Fruits as Inhibitors of Flaviviruses and Mycobacterium tubercolosis

et al. 2015

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The biological diversity of nature is the source of a wide range of bioactive molecules. The natural products, either as pure compounds or as standardized plant extracts, have been a successful source of inspiration for the development of new drugs. The present work was carried out to investigate the cytotoxicity, antiviral and antimycobacterial activity of the methanol extract and of four identified limonoids from the fruits of Melia azedarach (Meliaceae). The extract and purified limonoids were tested in cell-based assays for antiviral activity against representatives of ssRNA, dsRNA and dsDNA viruses and against Mycobacterium tuberculosis. Very interestingly, 3-α-tigloyl-melianol and melianone showed a potent antiviral activity (EC50 in the range of 3–11μM) against three important human pathogens, belonging to Flaviviridae family, West Nile virus, Dengue virus and Yellow Fever virus. Mode of action studies demonstrated that title compounds were inhibitors of West Nile virus only when added during the infection, acting as inhibitors of the entry or of a very early event of life cycle. Furthermore, 3-α-tigloyl-melianol and methyl kulonate showed interesting antimycobacterial activity (with MIC values of 29 and 70 μM respectively). The limonoids are typically lipophilic compounds present in the fruits of Melia azeradach. They are known as cytotoxic compounds against different cancer cell lines, while their potential as antiviral and antibacterial was poorly investigated. Our studies show that they may serve as a good starting point for the development of novel drugs for the treatment of infections by Flaviviruses and Mycobacterium tuberculosis, for which there is a continued need.

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Kadcotriones A–C: Tricyclic Triterpenoids from Kadsura coccinea

Cited by 41 publications

References 19 publications

Triterpenoids from the Schisandraceae family: an update

Triterpenoids from the Schisandraceae family: an update

Triterpenoids

Limonoids from Melia azedarach Fruits as Inhibitors of Flaviviruses and Mycobacterium tubercolosis

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