Synthesis and anti-hepatitis B virus activity of C4 amide-substituted isosteviol derivatives

Huang, Tsurng Juhn; Yang, Cheng Lin; Kuo, Yi Chun; Chang, Yu Han; Yang, Liming; Chou, Bo Hon; Lin, Shwu Jiuan

doi:10.1016/j.bmc.2014.12.064

Cited by 19 publications

(17 citation statements)

References 26 publications

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“…In-vitro synthesis of the isosteviol derivative having C4-amide moiety is designed as an antiviral HBV agent. Among them, IN-4 [ N -(propyl carbonyl)-4-amino-19-nor- ent -16-ketobeyeran] (Figure 3D) displayed inhibition of not only HBV DNA replication but also that of secretion of HBsAg and HBeAg [111]. It significantly inhibits HBV gene regulation by disrupting nuclear factor (NF)-B-associated promoter activity that halts viral gene expression and DNA replication [111].…”

Section: Pharmacological Activities Of Isosteviol Derivativesmentioning

confidence: 99%

“…Among them, IN-4 [ N -(propyl carbonyl)-4-amino-19-nor- ent -16-ketobeyeran] (Figure 3D) displayed inhibition of not only HBV DNA replication but also that of secretion of HBsAg and HBeAg [111]. It significantly inhibits HBV gene regulation by disrupting nuclear factor (NF)-B-associated promoter activity that halts viral gene expression and DNA replication [111]. The stevioside is the raw material for the synthesis of (−)-Tripterifordin and (−)-Neotripterifordin that are potential inhibitors of the HIV replication process [112].…”

Section: Pharmacological Activities Of Isosteviol Derivativesmentioning

confidence: 99%

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Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

et al. 2019

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Steviosides, rebaudiosides and their analogues constitute a major class of naturally occurring biologically active diterpene compounds. The wide spectrum of pharmacological activity of this group of compounds has developed an interest among medicinal chemists to synthesize, purify, and analyze more selective and potent isosteviol derivatives. It has potential biological applications and improves the field of medicinal chemistry by designing novel drugs with the ability to cope against resistance developing diseases. The outstanding advancement in the design and synthesis of isosteviol and its derivative has proved its effectiveness and importance in the field of medicinal chemical research. The present review is an effort to integrate recently developed novel drugs syntheses from isosteviol and potentially active pharmacological importance of the isosteviol derivatives covering the recent advances.

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Section: Pharmacological Activities Of Isosteviol Derivativesmentioning

confidence: 99%

Section: Pharmacological Activities Of Isosteviol Derivativesmentioning

confidence: 99%

Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

et al. 2019

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“…Isosteviol (STV) is a synthetic steviol glycoside derivative, which belongs to diterpene molecule 1 . STV exhibited a wide range of biological activities and pharmacological effects, including anti-fungal 2 , anti-neoplastic 3 , 4 , 5 , anti-viral 6 , 7 , improving insulin sensitivity, reducing plasma triglycerides 8 , 9 . It also reduces vasoconstriction by the regulation of the ion channels and has cardioprotective effect against coronary reperfusion damage with little toxicity 10 , 11 , 12 .…”

Section: Introductionmentioning

confidence: 99%

Simultaneous improvement to solubility and bioavailability of active natural compound isosteviol using cyclodextrin metal-organic frameworks

Chen

Guo

Zhang

et al. 2021

Acta Pharmaceutica Sinica B

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Cyclodextrin metal-organic framework (CD-MOF) as a highly porous supramolecular carrier could be one of the solutions to the insolubility of isosteviol (STV). The solubility of STV was lower than 20.00 ng/mL at pH 1.0 and pH 4.5, whilst its solubility increased to 20,074.30 ng/mL at pH 6.8 and 129.58 ng/mL in water with a significant pH-dependence. The in vitro release profiles of STV from STV@CD-MOF (0.5:1) were pH-independent in distinct pH media and closed to be thoroughly released but no such release profiles were observed for STV@CD-MOF (1:1) owing to nanoclusters formation. The bioavailability of STV@CD-MOF (1:1) in rats was 8.67-fold higher than that of STV, and was 1.32- and 1.27-fold higher than that of STV@CD and STV@CD-MOF (0.5:1). Our results indicated that the inclusion mechanism played a primary role when STV in CD-MOF was at a low loading ratio, while the increasement in bioavailability at a high loading ratio, which was attributed to the nanocluster mechanism. This was confirmed by molecular simulation. In conclusion, CD-MOF is a promising system for STV loading, overcoming the insolubility and to improve the bioavailability of this natural compound.

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“…Previous studies have revealed the biological effects of isosteviol derivatives, including anti-hypertension, anti-inflammation, anti-diarrhea, anti-cancer, anti-viral, and anti-bacterial activity 12 – 16 , 26 . Specifically, isosteviol derivatives were found to inhibit the NF-κB signaling pathway 14 , 26 , 27 , which is closely associated with osteoclast differentiation 18 , 28 , 29 . Therefore, we set out to investigate the effects of an isosteviol derivative, NC-8, in RANKL-induced osteoclastogenesis, which is activated through the NF-κB and MAPK signaling pathways.…”

Section: Discussionmentioning

confidence: 99%

Isosteviol Derivative Inhibits Osteoclast Differentiation and Ameliorates Ovariectomy-Induced Osteoporosis

Tzeng

Huang

Tsai

et al. 2018

Sci Rep

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NC-8 (ent-16-oxobeyeran-19-N-methylureido) is an isosteviol-derived analogue with multiple biological effects, including anti-inflammation and anti-bacterial activities and inhibition of HBV viral surface antigen gene expression. In this study, we explored the effects of NC-8 on the formation of osteoclasts from RAW 264.7 cells. We found that NC-8 exerts the novel effect of inhibiting osteoclast-like cell formation. Our experiments showed that RANKL-induced ERK, p38, and JNK phosphorylation were inhibited by NC-8. An ovariectomy-induced osteoporosis animal model was used to examine the protective effects of oral treatment with NC-8. Serum analysis was used to examine markers of osteoblasts, osteoclasts, and renal and hepatic function in rats. Micro CT scanning and histological analysis were used to measure bone loss in ovariectomized rats. Oral administration of NC-8 effectively decreased excess bone resorption and significantly antagonized trabecular bone loss in ovariectomized rats. Serum analysis of C-terminal telopeptide of type-I collagen, an osteoclast marker, also showed that NC-8 administration inhibited excess bone resorption. Furthermore, serum analysis showed that renal and liver function were not affected by these doses of NC-8 during long-term treatment. Our results demonstrate that NC-8 inhibits osteoclast differentiation and effectively ameliorates ovariectomy-induced osteoporosis.

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Synthesis and anti-hepatitis B virus activity of C4 amide-substituted isosteviol derivatives

Cited by 19 publications

References 26 publications

Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

Simultaneous improvement to solubility and bioavailability of active natural compound isosteviol using cyclodextrin metal-organic frameworks

Isosteviol Derivative Inhibits Osteoclast Differentiation and Ameliorates Ovariectomy-Induced Osteoporosis

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