Bufospirostenin A and Bufogargarizin C, Steroids with Rearranged Skeletons from the Toad <i>Bufo bufo gargarizans</i>

Tian, Hai‐Yan; Ruan, Li-Jun; Yu, Tong Lei; Zheng, Qingfei; Chen, Nanhao; Wu, Ruibo; Zhang, Xiaoqi; Wang, Lei; Jiang, Ren‐Wang; Ye, Wen‐Cai

doi:10.1021/acs.jnatprod.6b01018

Cited by 35 publications

(34 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It has a strong cardiotonic effect with potent Na + , K + -ATPase inhibitory activity. [4] But clinical application of bufalin is limited due to poor water solubility and large toxic side effects. [5,6] Glycosylation modification can enhance the water solubility, [7] targeting [8] and reduce the toxic and side effects of drugs.…”

Section: Introductionmentioning

confidence: 99%

“…Bufalin is one of the major constituents from Venenum Bufonis , a Traditional Chinese Medicine used for the treatment of heart failure. It has a strong cardiotonic effect with potent Na + , K + ‐ATPase inhibitory activity [4] . But clinical application of bufalin is limited due to poor water solubility and large toxic side effects [5,6] .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase

Liu

Xü

Huang

et al. 2020

Chemistry & Biodiversity

View full text Add to dashboard Cite

In this study, bufalin was glycosylated by an efficient chemo-enzymatic strategy. Firstly, 2-chloro-4nitrophenyl-1-O-β-D-glucoside (sugar donors) was obtained by chemical synthesis. Then, the glycosylation of the bufalin was achieved with the synthesized sugar donor under the catalysis of two glycosyltransferases (Loki and ASP). Finally, two glycosides, i. e., bufalin-3-O-β-D-glucopyranoside and bufalin-3-O-[β-D-glucopyranosyl-(1!2)-β-D-glucopyranoside)], were obtained by preparative HPLC. Compared to our previously reported sole chemical (total yield 10 % in four steps) or enzymatic methods (30 %), our combined chemo-enzymatic strategy in this article greatly improves the yields of monoglycoside (68 %) and diglycoside (21 %) and decreased the experimental cost (90 %). Furthermore, we tested the water solubility of these glycosides and found that the water solubilities of the two glycosides were 13.1 and 53.7 times of bufalin, respectively. In addition, the inhibitory activity of these glycosides against Na + , K +-ATPase were evaluated. The mono-glycosylated compound showed more potent activity than bufalin, while the diglycosylated compound was less potent.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase

Liu

Xü

Huang

et al. 2020

Chemistry & Biodiversity

View full text Add to dashboard Cite

show abstract

“…Therefore, the completed structure of 1 was established and given the trivial name bufogargarizin D. Compound 1 features an unusual C 23 skeleton with a 7/5/6/5/6 ring system, which is distinctly different from the common C 24 skeleton for 6/6/6/5/6 ring system bufadienolides. So far, only six A/B ring rearranged bufadienolides have been reported, and five of them were discovered by our research group. − A biosynthesis pathway was proposed in our previous research, involving the oxidation of the vicinal diols in the precursor compound 5 , followed by an intramolecular aldol condensation to form the 7/5 or 5/7 A/B ring system . The highly unsaturated 7/5 rings in 1 can be formed by further dehydration (Scheme S1, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Bufadienolides from the Eggs of the Toad Bufo bufo gargarizans and Their Antimelanoma Activities

Zhou

Quan

et al. 2021

J. Nat. Prod.

Self Cite

View full text Add to dashboard Cite

Toads produce potent toxins, named bufadienolides, to defend against their predators. Pharmacological research has revealed that bufadienolides are potential anticancer drugs. In this research, we reported nine bufadienolides from the eggs of the toad Bufo bufo gargarizans, including two new compounds (1 and 3). The chemical structures of 1 and 3, as well as of one previously reported semisynthesized compound (2), were elucidated on the basis of extensive spectroscopic data interpretation, chemical methods, and X-ray diffraction analysis. Compound 1 is an unusual 19-norbufadienolide with rearranged A/B rings. A biological test revealed that compounds 2 and 4–8 showed potent cytotoxic activities toward human melanoma cell line SK-MEL-1 with IC50 values less than 1.0 μM. A preliminary mechanism investigation revealed that the most potent compound, 8, could induce apoptosis via PARP cleavage, while 5 and 6 significantly suppressed angiogenesis in zebrafish. Furthermore, an in vivo biological study showed that 5, 6, and 8 inhibit SK-MEL-1 cell growth significantly.

show abstract

“…Compound (15) is an unusual bufadienolide with a cycloheptatriene B ring. [30] Caloncobalactone C (16) was isolated from the methanol extract of the leaves of Caloncoba glauca (Flacourtiaceae). [31] Several steroids (17)(18)(19)(20)(21)(22) produced by different fungal species.…”

Section: Introductionmentioning

confidence: 99%

“…Compound (27) showed anticancer activity, and kadsuphilactone B (28) exhibited in vitro anti-HBV activity with IC50 values of 6 μg/mL by HBsAg enzyme immunoassay. [38,39] The sedative triterpenes (30)(31)(32) were found in leaves and roots of the Galphimia glauca. [40] Longipedlactone J (33) showed the cytopathic effect (EC50 3.8 g/mL) of HIV-1 in C8166 cells, and cycloartane triterpenoid angustific acid A (34) from Kadsura angustifolia reaches EC50 values of 6 g/mL.…”

Section: Introductionmentioning

confidence: 99%

Highly oxygenated isoprenoid lipids derived from terrestrial and aquatic sources: Origin, structures and biological activities

Vil

Gloriozova

Terent’ev

et al. 2019

Vietnam Journal of Chemistry

View full text Add to dashboard Cite

This mini review is devoted to an interesting group of natural terpenoids called highly oxygenated isoprenoid lipids (HOIL). Their producers are microorganisms, as well as they are found in plants, fungi, animals and marine organisms. The present review consists of three parts. For all three groups of HOIL presented, the chemical structure and the calculated biological activity are given. The first is an overview of HOIL found in nature with a description of some of the pharmacological properties and activity. For the first group of terpenoids, the most characteristic activities are anti‐seborrheic, antineoplastic, and anti‐inflammatory, and they can be used as ovulation inhibitors with a certainty of 85 to 91 percent. In the second part, we present an interesting group of heterocyclic HOIL (or steroidal alkaloids) found in nature with an indication of their possible activity. For the second group of HOIL, the most characteristic activities are: hypolipemic, antifungal, and antineoplastic, and they can be used as lipid metabolism regulators with a confidence of 81 to 89 percent. And in the third group, we represent HOIL derived from marine microorganisms and invertebrates. For the third group of HOIL, the most characteristic activities are: antineoplastic and antipsoriatic and they can be used as cytochrome P450 inhibitors and hepatoprotectants with a confidence of 77 to 93 percent.

show abstract

Bufospirostenin A and Bufogargarizin C, Steroids with Rearranged Skeletons from the Toad Bufo bufo gargarizans

Cited by 35 publications

References 21 publications

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase

Bufadienolides from the Eggs of the Toad Bufo bufo gargarizans and Their Antimelanoma Activities

Highly oxygenated isoprenoid lipids derived from terrestrial and aquatic sources: Origin, structures and biological activities

Contact Info

Product

Resources

About

Bufospirostenin A and Bufogargarizin C, Steroids with Rearranged Skeletons from the Toad Bufo bufo gargarizans

Cited by 35 publications

References 21 publications

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na+, K+‐ATPase

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na+, K+‐ATPase

Bufadienolides from the Eggs of the Toad Bufo bufo gargarizans and Their Antimelanoma Activities

Highly oxygenated isoprenoid lipids derived from terrestrial and aquatic sources: Origin, structures and biological activities

Contact Info

Product

Resources

About

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase