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

Yan-Ni Shi; Fang-Fang Liu; Melissa R. Jacob; Xing-Cong Li; Hong-Tao Zhu; Dong Wang; Rong-Rong Cheng; Chong-Ren Yang; Min Xu; Ying-Jun Zhang

doi:10.1055/s-0042-109778

Planta Medica, Inhaltsverzeichnis

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^*

¹State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China

²University of Chinese Academy of Sciences, Beijing, Peopleʼs Republic of China

,

Fang-Fang Liu^*

¹State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China

³Yunnan University of Traditional Chinese Medicine, Kunming, Peopleʼs Republic of China

,

Melissa R. Jacob

⁴National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS, United States

,

Xing-Cong Li

⁴National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS, United States

,

Hong-Tao Zhu

¹State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China

⁵Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, People's Republic of China

,

Dong Wang

¹State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China

⁵Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, People's Republic of China

,

Rong-Rong Cheng

¹State 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

¹State 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

¹State 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

¹State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China

⁵Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, People's Republic of China

› Institutsangaben

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

Volltext

Referenzen

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