Phytochemical study of Seriphidium khorassanicum (syn. Artemisia khorassanica) aerial parts: sesquiterpene lactones with anti-protozoal activity

• Published in: Natural product research Vol. 38; no. 1; pp. 16 - 27
• Main Authors: Fattahian, Maryam, Ghanadian, Mustafa, Zolfaghari, Behzad, Abdeyazdan, Sara, Saberi, Sedigheh, Zulfiqar, Fazila, Khan, Ikhlas A, Ali, Zulfiqar
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 01.01.2024; Taylor & Francis Ltd
• Subjects: Amastigote; Amastigotes; Animals; Artemisia; Artemisia khorassanica; asteraceae; Asteraceae - chemistry; Data analysis; eudesmanolide; glucantime; Lactones; Lactones - chemistry; Lactones - pharmacology; Leishmania major; Macrophages; Meglumine antimoniate; Mice; NMR; Nuclear magnetic resonance; Phytochemicals - pharmacology; Plant Components, Aerial; Promastigotes; Seriphidium khorassanicum; sesquiterpene lactone; Sesquiterpene lactones; Sesquiterpenes - chemistry; Sesquiterpenes - pharmacology; Toxicity; Artemisia khorassanica; asteraceae; glucantime; eudesmanolide; Seriphidium khorassanicum; sesquiterpene lactone; Amastigote; Leishmania major
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2022.2102630

Two new eudesmane-type sesquiterpene lactones, 1β,3α,8α-trihydroxy-11β,13-dihydroeudesma-4(15)-en-12,6α-olide (1) and 1β,4α,8α-trihydroxy-11β,13-dihydroeudesma-12,6α-olide (2), and an unprecedented elemane-type sesquiterpene lactone, 1β,2β,8α-trihydroxy-11β,13-dihydroelema-12,6α-olide (3) along with a known eudesmanolide artapshin (4) were isolated from Seriphidium khorassanicum. Structures were elucidated by NMR, HR-ESI-MS, and ECD spectral data analysis. The anti-protozoal activity was evaluated against Leishmania major promastigotes and amastigote-infected macrophages. They showed dose- and time-dependent activity against L. major amastigotes with IC 50 values in the range of 4.9 to 25.3 μM being favourably far below their toxicity against normal murine macrophages with CC 50 values ranging from 432.5 to 620.7 μM after 48 h of treatment. Compound 3 exhibited the strongest activity and the highest selectivity index (SI) with IC 50 of 4.9 ± 0.6 μM and SI of 88.2 comparable with the standard drug, meglumine antimoniate (Glucantime), with IC 50 and SI values of 15.5 ± 2.1 μM and 40.0, respectively.