Artaboterpenoids A and B, Bisabolene-Derived Sesquiterpenoids from <i>Artabotrys hexapetalus</i>

Xi, Feng‐Min; Ma, Shuang‐Gang; Liu, Yun‐Bao; Li, Li; Yu, Shi‐Shan

doi:10.1021/acs.orglett.6b01519

Cited by 37 publications

(20 citation statements)

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“…[ 8–14 ] They have been shown to exhibit significant biological activities, [ 15–17 ] including antifungal, [ 13,18 ] antibacterial, [ 9 ] antiviral, [ 19,20 ] and anticancer. [ 21,22 ] In lieu of the above mentioned activities, the synthesis of different furanones, their derivatives, and their applications in the area of medicine have drawn considerable attention in recent years. [ 23–28 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives

Husain

Bhutani

Parveen

et al. 2020

J Chinese Chemical Soc

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A series of benzimidazole‐derived–furanones (4a–l) were synthesized, characterized, and explored for their in vitro anticancer activities. The pharmacokinetic parameters assessed revealed that all the compounds followed the Lipinski's rule of five, making them potential drug candidates. Further, the results of anticancer activity revealed that (E)‐5‐(1H‐benzo[d]imidazol‐2‐yl)‐3‐(3,4,5‐trimethoxybenzylidene)furan‐2(3H)‐one (4a), was active against A549, MCF7, and DU145 with an IC50 values of 10.4 ± 0.39, 11.1 ± 0.43, and 10.7 ± 0.19 μM, respectively. While another compound (E)‐5‐(1H‐benzo[d]imidazol‐2‐yl)‐3‐([5‐phenyl]furan‐2‐yl)furan‐2(3H)‐one (4k) also exhibited good activity against A549, MCF7, and DU145 with IC50 values of 11.4 ± 0.39, 9.1 ± 0.43, and 12.7 ± 0.19 μM, respectively. Doxorubicin was used as the standard drug. Further, molecular docking studies were carried out to provide binding mode into the binding sites of vascular endothelial growth factor receptor (VEGFR). Docking scores and binding energies corroborated well with the results of experimental anticancer activity. Pharmacokinetic (ADME) parameters of the potent derivatives were also found to be in an acceptable range. The benzimidazole‐furanonone conjugates seem to be a potential source for the further development of potent cytotoxic agents.

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Section: Introductionmentioning

confidence: 99%

Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives

Husain

Bhutani

Parveen

et al. 2020

J Chinese Chemical Soc

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“…Bisabolenes are a type of sesquiterpenoid with diverse bioactivities, including an anticonvulsant effect [1], inhibition of H 2 O 2 -induced apoptosis [2], and anticancer activity [3,4]. Many bisabolene-type sesquiterpenoids have been isolated and identified in various plants, such as β-bisabolenol and β-bisabolenal in Neocallitropsis pancheri [5], artaboterpenoids A and B in Artabotrys hexapetalus [6], and halichonic acid from a marine sponge Halichondria sp. [7].…”

Section: Introductionmentioning

confidence: 99%

Molecular Cloning and Functional Characterization of Bisabolene Synthetase (SaBS) Promoter from Santalum album

Yan

Xiong

Silva³

et al. 2020

Forests

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Bisabolene-type sesquiterpenoids, which have multiple bioactivities, including anticancer activity, are one of the main groups of compounds in the essential oil extracted from Santalum album L. and other Santalum species. Bisabolene synthetase (SaBS) is a key enzyme for the synthesis of bisabolene in S. album, but the regulation of the SaBS gene’s expression is poorly understood. In this study, a 1390-bp promoter sequence of the SaBS gene was isolated from the leaves of six-year-old S. album. A bioinformatics analysis showed that certain environment stresses and phytohormone-activated cis-acting elements were distributed in different regions of the SaBS promoter (PSaBS). Transgenic Arabidopsis carrying full-length PSaBS had significantly higher β-glucuronidase (GUS) activity than the untreated control after treatment with salicylic acid (SA), suggesting that PSaBS is a SA-inducible promoter. Histochemical GUS staining and GUS fluorometric assays of transgenic Arabidopsis showed that the GUS activity directed by PSaBS was mainly expressed in stem tissue, followed by leaves and flowers. Moreover, different regions of PSaBS showed significantly different GUS activity. A 171-bp fragment upstream of the transcriptional initiation codon (ATG) is the core promoter region of PSaBS. Our results provide insight into and a greater understanding of the transcriptional regulation mechanism of the SaBS gene, which could serve as an alternative inducible promoter for transgenic plant breeding.

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“…5 The modified bisabolane sesquiterpenoids artaboterpenoids A 8 and B 9 have been found in the roots of Artabotrys hexapetalus. 6 Artaboterpenoid A 8 has a 2,8-cyclised structure and the racemic artaboterpenoid B 9 is the first example of a 2,3-cleaved bisabolane derivative. Caesalpinone A 10, from pods of Caesalpinia spinosa, is the first example of a 1,15-cyclised gorgonane sesquiterpenoid.…”

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Hill

Sutherland

2016

Nat. Prod. Rep.

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Artaboterpenoids A and B, Bisabolene-Derived Sesquiterpenoids from Artabotrys hexapetalus

Cited by 37 publications

References 15 publications

Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives

Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives

Molecular Cloning and Functional Characterization of Bisabolene Synthetase (SaBS) Promoter from Santalum album

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