Bioactive aporphine alkaloids from the stems of Dasymaschalon rostratum

Zhangxin Yu; Changri Han; Xiaoping Song; Guangying Chen; Jinxiong Chen

doi:10.1016/j.bioorg.2019.103069

Bioactive aporphine alkaloids from the stems of Dasymaschalon rostratum

Bioorg Chem. 2019 Sep:90:103069. doi: 10.1016/j.bioorg.2019.103069. Epub 2019 Jun 17.

Authors

Zhangxin Yu¹, Changri Han², Xiaoping Song³, Guangying Chen⁴, Jinxiong Chen⁵

Affiliations

¹ Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China; Hainan Provincial Key Laboratory of Resources Conservation and Development of Southern Medicine, Hainan Branch of the Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Haikou 570311, China.
² Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China; Key Laboratory of Medicinal and Edible Plant Resources of Hainan Province, School of Chemical and Material Engineering, Hainan Institute of Science and Technology, Haikou 571126, China.
³ Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China; Key Laboratory of Medicinal and Edible Plant Resources of Hainan Province, School of Chemical and Material Engineering, Hainan Institute of Science and Technology, Haikou 571126, China. Electronic address: sxp628@126.com.
⁴ Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China. Electronic address: chgying123@163.com.
⁵ Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China.

PMID: 31271945
DOI: 10.1016/j.bioorg.2019.103069

Abstract

Three undescribed aporphine alkaloids dasymaroine A (1), 3-methoxyoxoputerine N-oxide (2), and dasymaroine B (3), along with nine known analogues (4-12) were isolated from the stems of Dasymaschalon rostratum Merr. The structures were elucidated using spectroscopic methods and by comparison with published NMR spectroscopic data. Compound 1 is a rarely reported nitro aporphine alkaloid and its absolute configuration was defined based on negative specific rotation and single-crystal X-ray diffraction. Compound 2 represents the first example of oxoaporphine alkaloid N-oxide. All compounds were evaluated for their activities of six pathogenic bacteria, 1 exhibited significant inhibition against Escherichia coli and Saphylococcus aureus with MIC values of 1.2 and 2.5 μM, respectively. As well as compounds 1-5, 7, 10, 12 were evaluated for their anti-HIV activities with EC₅₀ ranged from 1.93 to 9.70 μM.

Keywords: Anti-HIV; Dasymaschalon rostratum; Nitro aporphine alkaloid; Oxoaporphine N-oxide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / pharmacology*
Annonaceae / chemistry*
Anti-Bacterial Agents / pharmacology*
Anti-HIV Agents / pharmacology*
Aporphines / chemistry*
Bacteria / drug effects
HIV / drug effects
Molecular Structure
Plant Extracts / pharmacology*
Plant Stems / chemistry*

Substances

Alkaloids
Anti-Bacterial Agents
Anti-HIV Agents
Aporphines
Plant Extracts