Two lignans derivatives and two fusicoccane diterpenoids from the whole plant of Hypoestes verticillaris (L.F.) Sol. Ex roem. &amp; schult

Omole, Ruth Anyango; Moshi, Mainen J.; Heydenreich, Matthias; Malebo, Hamisi M.; Gathirwa, Jeremiah; Ochieng, Sharon Alice; Omosa, Leonidah Kerubo; Midiwo, Jacob O.

doi:10.1016/j.phytol.2019.02.019

Cited by 11 publications

(3 citation statements)

References 23 publications

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“…To examine divergence of "core" intermediate 3 towards C18-α-Me fusicoccanes, we chose 3(11)-epoxyhypoestenone (2) as our target molecule. 3(11)-Epoxyhypoestenone ( 2) was recently isolated from Hypoestes forsskaolii [3g] and Hypoestes verticillaris, [17] respectively and was reported to exhibit strong Hsp90α binding affinity. [3g] Structurally, it features a transannular oxa-bridge.…”

Section: Methodsmentioning

confidence: 99%

A Two‐Phase Approach to Fusicoccane Synthesis To Uncover a Compound That Reduces Tumourigenesis in Pancreatic Cancer Cells

Chen

et al. 2022

Angewandte Chemie

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Alterbrassicicene D (1) and 3(11)‐epoxyhypoestenone (2) were synthesised via a two‐phase approach featuring concise construction of the 5‐8‐5 tricyclic intermediate and a tandem base‐mediated epoxide opening–transannular oxa‐Michael addition cascade to forge the complex skeleton of 2. The route is scalable and we generated 15 g of the tricyclic intermediate in 8 steps from (R)‐limonene and 720 mg of the penultimate bioactive intermediate in a protecting‐group‐free manner. Our synthesis enabled the structural determination of 2 and provided materials for preliminary anticancer evaluation. The penultimate intermediate showed therapeutic potential in terms of its ability to dramatically reduce the tumourigenic potential of PANC‐1 pancreatic cancer cells according to a limiting dilution tumour‐initiating assay. Our synthetic approach will facilitate unified access to naturally occurring fusicoccanes and their derivatives for anticancer evaluation.

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Section: Methodsmentioning

confidence: 99%

A Two‐Phase Approach to Fusicoccane Synthesis To Uncover a Compound That Reduces Tumourigenesis in Pancreatic Cancer Cells

Chen

et al. 2022

Angewandte Chemie

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“…Other examples of fusicoccan derivatives are represented by alterbrassicicene D (54) and 3(11)-epoxyhypoestenone (55), recently isolated from Hypoestes verticillaris [32]. Structurally, alterbrassicicene D (54) comprises an α,β-unsaturated ketone C-ring, and a single hydroxy group on the central eight-membered ring and 3(11)-epoxyhypoestenone (55) shows a surprising oxa-bridge between the A and C rings, an α,β-unsaturated ketone on ring C, and an endo-alkene into the cyclooctene ring.…”

Section: Strategymentioning

confidence: 99%

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

Alleman¹,

Gadais²,

Legentil³

et al. 2023

Beilstein J. Org. Chem.

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Terpene compounds probably represent the most diversified class of secondary metabolites. Some classes of terpenes, mainly diterpenes (C20) and sesterterpenes (C25) and to a lesser extent sesquiterpenes (C15), share a common bicyclo[3.6.0]undecane core which is characterized by the presence of a cyclooctane ring fused to a cyclopentane ring, i.e., a [5-8] bicyclic ring system. This review focuses on the different strategies elaborated to construct this [5-8] bicyclic ring system and their application in the total synthesis of terpenes over the last two decades. The overall approaches involve the construction of the 8-membered ring from an appropriate cyclopentane precursor. The proposed strategies include metathesis, Nozaki–Hiyama–Kishi (NHK) cyclization, Pd-mediated cyclization, radical cyclization, Pauson–Khand reaction, Lewis acid-promoted cyclization, rearrangement, cycloaddition and biocatalysis.

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“…6 In higher plants, fusicoccane diterpenoids were almost isolated from the Hypoestes species (Acanthaceae) except for liverworts. 7,8 In recent years, some rearranged fusicoccane diterpenoids with 5/9/5, 5/9/4, or 5/8/6-fused carbocyclic skeletons were also reported from fungi. [9][10][11] These compounds have been reported to exhibit remarkable anti-inflammatory, antitumor, and butyrylcholinesterase inhibitory activities.…”

Section: Introductionmentioning

confidence: 99%

Hypoestins A–D: highly modified fusicoccane diterpenoids with promising Ca_v3.1 calcium channel inhibitory activity from Hypoestes purpurea

Wu¹,

Ding²,

Li³

et al. 2022

Org. Chem. Front.

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Two lignans derivatives and two fusicoccane diterpenoids from the whole plant of Hypoestes verticillaris (L.F.) Sol. Ex roem. & schult

Cited by 11 publications

References 23 publications

A Two‐Phase Approach to Fusicoccane Synthesis To Uncover a Compound That Reduces Tumourigenesis in Pancreatic Cancer Cells

A Two‐Phase Approach to Fusicoccane Synthesis To Uncover a Compound That Reduces Tumourigenesis in Pancreatic Cancer Cells

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

Hypoestins A–D: highly modified fusicoccane diterpenoids with promising Ca_v3.1 calcium channel inhibitory activity from Hypoestes purpurea

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Two lignans derivatives and two fusicoccane diterpenoids from the whole plant of Hypoestes verticillaris (L.F.) Sol. Ex roem. & schult

Cited by 11 publications

References 23 publications

A Two‐Phase Approach to Fusicoccane Synthesis To Uncover a Compound That Reduces Tumourigenesis in Pancreatic Cancer Cells

A Two‐Phase Approach to Fusicoccane Synthesis To Uncover a Compound That Reduces Tumourigenesis in Pancreatic Cancer Cells

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

Hypoestins A–D: highly modified fusicoccane diterpenoids with promising Cav3.1 calcium channel inhibitory activity from Hypoestes purpurea

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Hypoestins A–D: highly modified fusicoccane diterpenoids with promising Ca_v3.1 calcium channel inhibitory activity from Hypoestes purpurea