Carbazole Alkaloids from Clausena anisum-olens: Isolation, Characterization, and Anti-HIV Evaluation

Yang, Jing‐Hua; Wang, Xinyi; Zhong, Yiping; Lu, Rong; Chen, Chin Ho; Zhang, Menghan; Cheng, Yung Yi; Morris‐Natschke, Susan L.; Lee, Kuo Hsiung̀; Wang, Yunsong

doi:10.3390/molecules25010099

Cited by 22 publications

(11 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Additionally, the existence of four groups of hydrogen signals, which resonate at δ H 4.62 (2H, s, 4-CH 2 ), 4.08 (3H, s, 1-OCH 3 ), 2.47 (3H, s, 3-CH 3 ), and 1.67 (6H, s, H-4″,5′′), indicated the presence of a methylene group, a methoxy group, and three methyl groups. The detailed data analyses of 13 C NMR data and DEPT data of 1 revealed the presence of 32 carbons, containing 26 sp 2 carbons, 4 methyl groups, 1 sp 3 quaternary carbon along with 1 sp 3 methylene. Furthermore, the 26 sp 2 carbons were ascribed to the existence of 2 carbazole rings and 1 double bond group.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Previous chemical investigation of C. anisum-olens yielded various compounds, containing alkaloids, lignans, cyclic peptides, and coumarins, which exhibited diverse biological activities, such as hypolipidemic, anti-HIV, and human monoamine oxidase inhibitory activities. − Our rudimentary biological activity evaluation data indicated that the crude extract of the fruits of C. anisum-olens possessed a remarkable anti-HIV-1 effect holding an EC 50 value of 8.27 μg/mL in vitro .…”

Section: Introductionmentioning

confidence: 84%

See 1 more Smart Citation

Clausanisumine, a Prenylated Bicarbazole Alkaloid from the Fruits of Clausena anisum-olens and Its Potential Anti-HIV Activity

et al. 2021

View full text Add to dashboard Cite

A unique prenylated bicarbazole alkaloid, clausanisumine (1), and two biogenetically related known monomer carbazole alkaloids, mukonal (2) and 3-methylcarbazole (3), were isolated from the fruits of Clausena anisum-olens. Clausanisumine (1) was an uncommon prenylated bicarbazole alkaloid, possessing an unprecedented carbon skeleton, which was composed of a simple carbazole alkaloid and a prenylated carbazole alkaloid. The chemical structure of 1 was established by a combination of comprehensive spectral methods. A plausible biosynthetic pathway of 1 was also proposed. Additionally, the potential anti-HIV activities of all isolates 1–3 in vitro were evaluated. Compound 1 exhibited remarkable anti-HIV-1 reverse transcriptase effects showing an EC50 value of 18.58 nM. The discovery of the prenylated bicarbazole alkaloid from C. anisum-olens with notable anti-HIV activity would be meaningful to discovering and developing new anti-HIV drugs.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 84%

Clausanisumine, a Prenylated Bicarbazole Alkaloid from the Fruits of Clausena anisum-olens and Its Potential Anti-HIV Activity

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Carbazole alkaloids possess antibacterial, antiprotozoal, insecticidal, and antiviral activities due to their unique pharmacological activities and structural diversity [ 151 ]. Both natural and synthetic carbazole alkaloids have been reported to possess inhibitory activity against HIV, HCV, marsupial virus (CV), and HSV, etc., [ 152 , 153 , 154 , 155 , 156 , 157 ]. A recent study has reported that carbazole alkaloids and their analogs similarly possess antiviral activity.…”

Section: Other Potential Antiviral Agentsmentioning

confidence: 99%

The Advances of Broad-Spectrum and Hot Anti-Coronavirus Drugs

Zeng

Wang

et al. 2022

Microorganisms

View full text Add to dashboard Cite

Coronaviruses, mainly including severe acute respiratory syndrome virus, severe acute respiratory syndrome coronavirus 2, Middle East respiratory syndrome virus, human coronavirus OC43, chicken infectious bronchitis virus, porcine infectious gastroenteritis virus, porcine epidemic diarrhea virus, and murine hepatitis virus, can cause severe diseases in humans and livestock. The severe acute respiratory syndrome coronavirus 2 is infecting millions of human beings with high morbidity and mortality worldwide, and the multiplicity of swine epidemic diarrhea coronavirus in swine suggests that coronaviruses seriously jeopardize the safety of public health and that therapeutic intervention is urgently needed. Currently, the most effective methods of prevention and control for coronaviruses are vaccine immunization and pharmacotherapy. However, the emergence of mutated viruses reduces the effectiveness of vaccines. In addition, vaccine developments often lag behind, making it difficult to put them into use early in the outbreak. Therefore, it is meaningful to screen safe, cheap, and broad-spectrum antiviral agents for coronaviruses. This review systematically summarizes the mechanisms and state of anti-human and porcine coronavirus drugs, in order to provide theoretical support for the development of anti-coronavirus drugs and other antivirals.

show abstract

“…(Rutaceae) were evaluated on the HIV. They reported the highest antiviral activity against HIV virus for one of the new carbazole alkaloids [ 26 ]. Four pairs of enantiomers named (±)- β -myrifabral A, (±)- α -myrifabral A, (±)- β -myrifabral B, and (±)- α -myrifabral B were derived from Myrioneuron faberi Hemsl.…”

Section: Antiviral Activities Of Alkaloidsmentioning

confidence: 99%

Alkaloids as Potential Phytochemicals against SARS-CoV-2: Approaches to the Associated Pivotal Mechanisms

Majnooni

Fakhri

Bahrami

et al. 2021

Evidence-Based Complementary and Alternative Medicine

View full text Add to dashboard Cite

Since its inception, the coronavirus disease 2019 (COVID-19) pandemic has infected millions of people around the world. Therefore, it is necessary to find effective treatments against Severe Acute Respiratory Syndrome Coronavirus-2 (SARS-CoV-2), as it is the viral source of COVID-19. Alkaloids are one of the most widespread plant-derived natural compounds with prominent antiviral effects. Accordingly, these phytochemicals have been promising candidates towards discovering effective treatments for COVID-19. Alkaloids have shown potential anti-SARS-CoV activities via inhibiting pathogenesis-associated targets of the Coronaviridae family that are required for the virus life cycle. In the current study, the chemistry, plant sources, and antiviral effects of alkaloids, as well as their anti-SARS-CoV-2 effect with related mechanisms, are reviewed towards discovering an effective treatment against COVID-19.

show abstract

Carbazole Alkaloids from Clausena anisum-olens: Isolation, Characterization, and Anti-HIV Evaluation

Cited by 22 publications

References 34 publications

Clausanisumine, a Prenylated Bicarbazole Alkaloid from the Fruits of Clausena anisum-olens and Its Potential Anti-HIV Activity

Clausanisumine, a Prenylated Bicarbazole Alkaloid from the Fruits of Clausena anisum-olens and Its Potential Anti-HIV Activity

The Advances of Broad-Spectrum and Hot Anti-Coronavirus Drugs

Alkaloids as Potential Phytochemicals against SARS-CoV-2: Approaches to the Associated Pivotal Mechanisms

Contact Info

Product

Resources

About