Tanacetamide D: A New Ceramide from Tanacetum artemisioides

Abstract

One new ceramide (=long‐chain base linked to a fatty acid via an amide bond), tanacetamide D (1), was isolated from Tanacetum artemisioides. Besides this, the two known constituents 5‐demethylnobiletin (2) and 5‐hydroxy‐3,6,7,8,3′,4′‐hexamethoxyflavone (3) were isolated for the first time from this species. The structure elucidation of the isolated compounds were based primarily on 2D‐NMR techniques including correlation spectroscopy (COSY), heteronuclear multiple‐quantum coherence (HMQC), heteronuclear multiple‐bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOESY) experiments.

Tanacetum species: Bridging empirical knowledge, phytochemistry, nutritional value, health benefits and clinical evidence

“…Frontiers in Pharmacology frontiersin.org 2004). Likewise, tanacetamides C and D (73, 74), with promising vasorelaxant properties, were isolated and identified from the chloroform fraction of the whole plant methanolic extract (Hussain et al, 2005;Hussain et al, 2010). However, the antihypertensive properties of these ceramides are still poorly understood.…”

“…The geographical restriction of T. artemisioides in Pakistan allowed the emergence and spread of rich beliefs and practical knowledge within the mountains tribes. In the Kurram Valley, the locals call this species “Zawil” and “Zoon in Gilgit” , and they are used to relieve the flu by mixing and consuming powdered flowers with oil and sugar ( Hussain et al, 2010 ; Ali et al, 2019 ). They also used powdered leaves and fruits to alleviate and treat diabetes, high blood pressure, kidney, headache, fever, hepatitis, abdominal disorders, ringworm, and flatulence ( Hussain et al, 2010 ; 2018 ; Ullah et al, 2019 ).…”

“…In the Kurram Valley, the locals call this species “Zawil” and “Zoon in Gilgit” , and they are used to relieve the flu by mixing and consuming powdered flowers with oil and sugar ( Hussain et al, 2010 ; Ali et al, 2019 ). They also used powdered leaves and fruits to alleviate and treat diabetes, high blood pressure, kidney, headache, fever, hepatitis, abdominal disorders, ringworm, and flatulence ( Hussain et al, 2010 ; 2018 ; Ullah et al, 2019 ). Moreover, a glance at the existing data gathered from different geo-cultural areas indicated a typical usage of several Tanacetum species for diabetes management, including T. artemisioides .…”

“…In the same study, tanacetamides A and B disclosed substantial in vitro acetylcholinesterase inhibitory properties, with IC 50 values of 67.1 ± 1.5 and 74.1 ± 5.0 μM, respectively, compared to the standard drug galanthamine (IC 50 = 8.5 ± 0.0001 μM) ( Ahmad et al, 2004 ). Likewise, tanacetamides C and D (73, 74) , with promising vasorelaxant properties, were isolated and identified from the chloroform fraction of the whole plant methanolic extract ( Hussain et al, 2005 ; Hussain et al, 2010 ). However, the antihypertensive properties of these ceramides are still poorly understood.…”