Heterocyclic terpenes: linear furano- and pyrroloterpenoids

Wang, Bin; Wang, Li‐Shu; Li, Yinglei; Liu, Yonghong

doi:10.1039/c3ra48040b

Cited by 16 publications

(16 citation statements)

References 231 publications

(210 reference statements)

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“…The C-4 scission and furan ring installation are novel transformations that generate an important pharmacophore of the limonoids. Although likely the result of convergent evolution, furan rings are found in a variety of natural products ( 36, 37 ). Although furan-forming enzymes have been reported from other plants ( 38, 39 ), ( 40 ), the AKR, CYP716AD and 2-ODD module described here represents a new mechanism of furan formation via the oxidative cleavage of a C-4 moiety.…”

Section: Discussionmentioning

confidence: 99%

Complex scaffold remodeling in plant triterpene biosynthesis

Peña

Hodgson

Liu

et al. 2022

Preprint

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Triterpenes with complex scaffold modifications are widespread in plants yet little is known regarding biosynthesis. Limonoids are an exemplary family that includes the bitter taste in citrus (e.g., limonin) and the active constituents in neem oil, a widely used bioinsecticide (e.g., azadirachtin). Despite limonoid commercial value, a complete biosynthetic route has not been described. Here, we report the discovery of 22 enzymes that catalyze 12 unique reactions including the 4-carbon scission and furan installation that are a signature of the limonoid family and a pair of sterol isomerases previously unknown in plants. This gene set is then used for the total biosynthesis of kihadalactone A and azadirone in a heterologous plant. 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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Section: Discussionmentioning

confidence: 99%

Complex scaffold remodeling in plant triterpene biosynthesis

Peña

Hodgson

Liu

et al. 2022

Preprint

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“…Furan ring, as a critical pharmacophore, is widely present in many active natural products [14, 15] such as toosendanin (a known natural-product insecticidal agents) [16, 17] and limonin [18] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Furan-site transformations of obacunone as potent insecticidal agents

Xiang

Cao

Dong

et al. 2018

Heliyon

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Furan ring is a key pharmacophore for insecticidal activity of limoninoids. To develop natural-product-based insecticidal agents, a series of furan-site transformations (2, 3 and 3a–j) of obacunone were synthesized by selective bromination and following coupling reactions without altering other functional groups. Bioassays indicated that derivatives 3e, 3f and 3j displayed more potent insecticidal activity than obacunone and toosendanin against the instar larvae of Mythimna separate Walker. Besides, their structure–activity relationships were discussed.

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“…Linear terpenoids, represented by linear furano- and pyrrolo-terpenoids, are a unique family of natural products with widespread bioactivities [1,2]. Among all the isolated linear terpenoids, C 25 linear sesterterpenoids are the major components with more than 200 compounds been isolated, such as nitropyrrolins, heronapyrroles, fukanedones, and manoalide-type sesterterpenoids [3,4,5,6,7].…”

Section: Introductionmentioning

confidence: 99%

“…Inspiringly, the manoalide-type C 25 sesterterpenoids, which are frequently obtained from marine sponges, have been studied as topical antipsoriatic lead drug candidates for their potent anti-inflammatory activity [8,9]. Apart from the common C 15 sesquiterpenoids, C 20 diterpenoids, and C 25 sesterterpenoids, a few linear terpenoids take irregular C 17 or C 21 carbon skeletons [1,2,3,4,5,6,7]. To the best of our knowledge, there are only four C 17 terpenoids been isolated from red algae Laurencia viridis [10], marine spong Fasciospongia cavernosa [11], and Chloranthaceae plant Chloranthus sessilifolius [12].…”

Section: Introductionmentioning

confidence: 99%

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Isolation and Absolute Configurations of Diversiform C17, C21 and C25 Terpenoids from the Marine Sponge Cacospongia sp.

Zhang

Qin

et al. 2018

Marine Drugs

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Chemical investigation of MeOH extract of a South China Sea sponge Cacospongia sp. yielded 15 terpenoids belonging to three different skeleton-types, including the unusual C17 γ-lactone norditerpenoids (1–3), the rare C21 pyridine meroterpenoid (7), and the notable C25 manoalide-type sesterterpenoids (4–6, 8–10). Compounds 1–5 were initially obtained as enantiomers, and were further separated to be optically pure compounds (1a, 1b, 2a, 2b, 3a-r, 3b-r, 4a, 4b, 5a and 5b) by chiral HPLC, with a LiAlH4 reduction aid for 3. Compounds 3a/3b (a pair of inseparable enantiomers), 4a, 5a, 6, and 7 were identified as new compounds, while 1a/1b and 2a/2b were obtained from a natural source and were determined for their absolute configurations for the first time. This is also the first time to encounter enantiomers of the well-known manoalide-type sesterterpenoids from nature. The structures with absolute configurations of the new compounds were unambiguously determined by comprehensive methods including HR-ESI-MS and NMR data analysis, optical rotation comparison, experimental and calculated electronic circular dichroism (ECD), and Mo2(OAc)4 induced circular dichroism (ICD) methods. The cytotoxicity of the isolates against selected human tumor cell lines was evaluated, however, the tested compounds showed no activity against selected cell lines.

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Heterocyclic terpenes: linear furano- and pyrroloterpenoids

Cited by 16 publications

References 231 publications

Complex scaffold remodeling in plant triterpene biosynthesis

Complex scaffold remodeling in plant triterpene biosynthesis

Furan-site transformations of obacunone as potent insecticidal agents

Isolation and Absolute Configurations of Diversiform C17, C21 and C25 Terpenoids from the Marine Sponge Cacospongia sp.

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