Monoterpene Glucosides from Ziziphora clinopodioides (Labiatae)

Abstract

Three new monoterpene glucosides, ziziphoroside A (1), B (2), and C (3), together with fifteen known compounds were isolated from the whole herb of Z. clinopodioides. The structures of new compounds were determined primarily from 1D-, 2D-NMR and circular dichroism (CD) spectroscopic analyses. The isolated compounds were evaluated for their inhibitory activity against nitric oxide (NO) production by lipopolysaccharide (LPS) and interferon (IFN)-γ activated macrophages, RAW 264.7. Shizonepetoside A (8) and flavones (11, 12, 13) showed potent inhibitory activity against NO production.

Kazakh Ziziphora Species as Sources of Bioactive Substances

“…[39] Toxicity against Artemia salina larvae [62] Antiradical [63] Weak antibacterial effect [61] OH OCH3 OCH3 OCH3 OH H Acacetin (5) Z. clinopodioides [39] Low vasorelaxant activity (IC50 not calc.) [39] Inhibition of angiogenesis [64,65] Induction of apoptosis in different cancer cell lines [66][67][68][69][70] Inhibition of TNF-related apoptosis [71] Anticancer [72,73] Induction of melanogenesis in B16F10 cells [74] Cytotoxic against HL-60 cells cells [75] Interaction with telomeres [76] Antimetastatic effect [77,78] Diosmetin (6) Z. clinopodioides [4] Some inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4] Cytotoxic against HL-60 cells cells [75] Induction of melanogenesis in B16F10 cells [73,74] Review on bioactivity [79] H OH H OH OCH 3 H Diosmin (7) Z. clinopodioides [80] Antidiabetic activity (reviewed by Abdurrazak et al [81]) Review on clinical use [82] H O-Glc-Rha H OH OCH 3 Hf Linarin (8) Z. clinopodioides [44,80] Inhibition of mucin production and secretion in airways epithelial cells [83] Hepatoprotective [84] Potential inhibitor of CDK4 in retinoblastoma [85] Neuroprotective [86] Inhibition of acetylcholinesterase [87] Anti-inflammatory [88]...…”

“…Benzoic acid (21) Z. clinopodioides [4] Weak inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4] Properties reviewed here [119] HOOC (Z)-3-Hexen-1-ol benzoate (22) Z. tenuior [94] n.f. …”

“…clinopodioides ( [4,44] Weak inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4] Glucosidase inhibitor (review by Benalla et al [97])…”

“…Caffeic acid (17) Z. clinopodioides [80] Anticancer potential reviewed [98] Protection of endothelial cells (review by Fuentes and Palomo [99]) General review on applications [100] O H O OH Ethyl ester of caffeic acid (18) Z. clinopodioides [4] Weak inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4] Antihypertensive [101,102] Anti-inflammatory [103][104][105] Antidiabetic [106] Inhibitory activity against amyloidogenesis [107] Antioxidative [108][109][110][111] Anticancer [112] O H…”

“…Benzylalcohol glucoside (23) Z. clinopodioides [4] Weak inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4] Antihypertensive effect [120] Low anti-inflammatory activity [121] Neuroprotective effect [122] Weak inhibition of TPA-induced EBV-EA activation [123] …”