Amides, Isoquinoline Alkaloids and Dipeptides from the Aerial Parts of Piper mullesua

doi:10.1007/s13659-018-0180-z

Natural Products and Bioprospecting ›› 2018, Vol. 8 ›› Issue (6): 419-430.DOI: 10.1007/s13659-018-0180-z

• ORIGINAL ARTICLES • Previous Articles Next Articles

Amides, Isoquinoline Alkaloids and Dipeptides from the Aerial Parts of Piper mullesua

Meng-Yuan Xia^1,2, Jun Yang^1,2, Pan-Hua Zhang¹, Xiao-Nian Li³, Ji-Feng Luo¹, Chun-Lin Long^4,5, Yue-Hu Wang^1,2

1 Key Laboratory of Economic Plants and Biotechnology and the Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2 Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences, Yezin, Nay Pyi Taw 05282, Myanmar;
3 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
4 College of Life and Environmental Sciences, Minzu University of China, Beijing 100081, People's Republic of China

Received:2018-06-03 Revised:2018-07-03 Online:2018-11-21 Published:2018-12-24
Contact: Chun-Lin Long, Yue-Hu Wang
Supported by:
This work was funded by the Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences (Y4ZK111B01), the Natural Science Foundation of Yunnan Province, China (2011FZ205), the International Partneship Program of Chinese Academy of Sciences (153631KYSB20160004), the Key Laboratory of Ethnomedicine (Minzu University of China) of Ministry of Education of China (KLEM-ZZ201806), and the National Natural Science Foundation of China (31761143001 & 31161140345).

Amides, Isoquinoline Alkaloids and Dipeptides from the Aerial Parts of Piper mullesua

Meng-Yuan Xia^1,2, Jun Yang^1,2, Pan-Hua Zhang¹, Xiao-Nian Li³, Ji-Feng Luo¹, Chun-Lin Long^4,5, Yue-Hu Wang^1,2

1 Key Laboratory of Economic Plants and Biotechnology and the Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2 Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences, Yezin, Nay Pyi Taw 05282, Myanmar;
3 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
4 College of Life and Environmental Sciences, Minzu University of China, Beijing 100081, People's Republic of China

通讯作者: Chun-Lin Long, Yue-Hu Wang
基金资助:
This work was funded by the Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences (Y4ZK111B01), the Natural Science Foundation of Yunnan Province, China (2011FZ205), the International Partneship Program of Chinese Academy of Sciences (153631KYSB20160004), the Key Laboratory of Ethnomedicine (Minzu University of China) of Ministry of Education of China (KLEM-ZZ201806), and the National Natural Science Foundation of China (31761143001 & 31161140345).

Abstract

Abstract: One undescribed amide, pipermullesineA, two undescribed isoquinoline alkaloids, pipermullesines B and C, and six undescribed dipeptides, pipermullamides A-F, along with 28 known compounds, were isolated from the aerial parts of Piper mullesua. The structures of the undescribed compounds were elucidated based on the analysis of 1D and 2D NMR and MS data. Furthermore, the structures of pipermullesines A-C were confirmed by single crystal X-ray diffraction analysis. All isolates were evaluated for inhibitory activity against platelet aggregation induced by thrombin (Ⅱa) or platelet-activating factor (PAF). (-)-Mangochinine, pellitorine, and (2E,4E)-N-isobutyl-2,4-dodecadienamide showed weak inhibitory activity against rabbit platelet aggregation induced by PAF, with IC₅₀ values of 470.3 μg/mL, 614.9 μg/mL, and 579.7 μg/mL, respectively.

Key words: Piper mullesua, Piperaceae, Antiplatelet, Amides, Isoquinoline alkaloids

摘要： One undescribed amide, pipermullesineA, two undescribed isoquinoline alkaloids, pipermullesines B and C, and six undescribed dipeptides, pipermullamides A-F, along with 28 known compounds, were isolated from the aerial parts of Piper mullesua. The structures of the undescribed compounds were elucidated based on the analysis of 1D and 2D NMR and MS data. Furthermore, the structures of pipermullesines A-C were confirmed by single crystal X-ray diffraction analysis. All isolates were evaluated for inhibitory activity against platelet aggregation induced by thrombin (Ⅱa) or platelet-activating factor (PAF). (-)-Mangochinine, pellitorine, and (2E,4E)-N-isobutyl-2,4-dodecadienamide showed weak inhibitory activity against rabbit platelet aggregation induced by PAF, with IC₅₀ values of 470.3 μg/mL, 614.9 μg/mL, and 579.7 μg/mL, respectively.

关键词: Piper mullesua, Piperaceae, Antiplatelet, Amides, Isoquinoline alkaloids

Meng-Yuan Xia, Jun Yang, Pan-Hua Zhang, Xiao-Nian Li, Ji-Feng Luo, Chun-Lin Long, Yue-Hu Wang. Amides, Isoquinoline Alkaloids and Dipeptides from the Aerial Parts of Piper mullesua[J]. Natural Products and Bioprospecting, 2018, 8(6): 419-430.

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Amides, Isoquinoline Alkaloids and Dipeptides from the Aerial Parts of Piper mullesua

Amides, Isoquinoline Alkaloids and Dipeptides from the Aerial Parts of Piper mullesua

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