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Planta Med 2017; 83(01/02): 143-150
DOI: 10.1055/s-0042-109778
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antifungal Amide Alkaloids from the Aerial Parts of Piper flaviflorum and Piper sarmentosum

Yan-Ni Shi   *
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
2   University of Chinese Academy of Sciences, Beijing, Peopleʼs Republic of China
,
Fang-Fang Liu   *
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
3   Yunnan University of Traditional Chinese Medicine, Kunming, Peopleʼs Republic of China
,
Melissa R. Jacob
4   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS, United States
,
Xing-Cong Li
4   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS, United States
,
Hong-Tao Zhu
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
5   Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, People's Republic of China
,
Dong Wang
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
5   Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, People's Republic of China
,
Rong-Rong Cheng
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
,
Chong-Ren Yang
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
,
Min Xu
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
,
Ying-Jun Zhang
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
5   Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, People's Republic of China
› Author Affiliations
Further Information

Publication History

received 30 October 2015
revised 11 May 2016

accepted 18 May 2016

Publication Date:
12 July 2016 (online)

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Abstract

Sixty-three amide alkaloids, including three new, piperflaviflorine A (1), piperflaviflorine B (2), and sarmentamide D (4), and two previously synthesized ones, (1E,3S)-1-cinnamoyl-3- hydroxypyrrolidine (3) and N-[7′-(4′-methoxyphenyl)ethyl]-2-methoxybenzamide (5), were isolated from the aerial parts of Piper flaviflorum and Piper sarmentosum. Their structures were elucidated by detailed spectroscopic analysis and, in case of 3, by single-crystal X-ray diffraction. Most of the isolates were tested for their antifungal and antibacterial activities. Ten amides (6–15) showed antifungal activity against Cryptococcus neoformans ATCC 90 113 with IC50 values in the range between 4.7 and 20.0 µg/mL.

Key words

Piper flaviflorum - Piper sarmentosum - Piperaceae - amide alkaloids - antifungal activity

* These authors contributed equally to this work.


Supporting Information

 

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