Table 1.

Phenolic substances isolated from Kazakhstan Ziziphora species. (N.f.—not found).

Flavonoids
Name of Compound and ID	Isolation/Detection in Kazakhstan spp. of Ziziphora	Biological Activity	Chemical Structure
			R1	R2	R3	R4	R5	R6
Apigenin (1)	Z. tenuior [38]; Z. clinopodioides [4,39,40]	Vasorelaxant activity (IC50 189.4 ± 12.4 µM) [39]; Some inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4] Review on apigenin (1) on breast cancer [41] Anticancer activity review [42,43,44] Review on apigenin (1) impact on gastric cancer [45] General review on the impact of apigenin (1) on health and disease [46]	H	OH	H	H	OH	H
Chrysin (2)	Z. clinopodioides [39]	Vasorelaxant activity (IC50 347.8 ± 23.9 µM) [39] Neuroprotective activity reviewed [47] Anticancer activity reviewed [48,49] Recent general review on bioactivities of chrysin (2) and its derivatives [50]	H	OH	H	H	H	H
Luteolin (3)	Z. clinopodioides [4]	Some inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4] Anticancer [51,52] Review on anti-inflammatory and neuroprotective effect [53,54] Neurotrophic effects [55] Anti-allergic [56] Anti-atherogenic [57] Cardioprotective [58] General reviews on luteolin (3) [59,60]	H	OH	H	OH	OH	H
Thymonin (4)	Z. clinopodioides [39,61]	Low vasorelaxant activity (IC50 not calc.) [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]	H	OH	H	H	OCH3	H
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	OCH3	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	OCH3	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]; Anti-inflammatory in vivo [89] Depressant effect on CNS [90,91]	H	O-Glc-Rha	H	H	OCH3	H
Ziziphorin A (9)	Z. tenuior [39]	n.f.	H	OH	H	H	OCO(CH2)17CH3	H
Ziziphorin B (10)	Z. tenuior [39]	n.f.	H	OH	H	H	H	OCO(CH2)25CH3)
5,7,2′-trihydroxyflavone-2′-O-β-d-glucopyranoside (11)	Z. clinopodioides [44]	n.f.	H	OH	H	H	H	O-Glc
Other Phenolics
Name of Compound and ID	Isolation/Detection in Kazakhstan spp. of Ziziphora	Biological Activity	Chemical Structure
Acetovanillone (syn. apocynin) (12)	Z. clinopodioides [39]	Low vasorelaxant activity (IC50 not calc.) [39] Review on its potential in treatment of cardiovascular diseases [92] Review on its potential in treatment of neurodegenerative diseases [93]	R1			R2
			OH			OCH3
4-Hydroxyaceto-phenone (syn. piceol) (13)	Z. clinopodioides [39]	Low vasorelaxant activity (IC50 not calc.) [39]	OH			H
Acetophenone (14)	Z. tenuior [94]	Tyrosinase inhibition [95] Acaricidal effect [96]	H			H
Picein (15)	Z. 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])	O-Glc			H
2-Methoxy-4-vinylphenol (16)	Z. clinopodioides [15]	n.f.
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]
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]
Rosmarinic acid (19)	Z. clinopodioides [80]	Review on pharmaceutical and clinical usage [113] Neuroprotective—review [114] General review on applications [115] Review on anticancer potential [116]
Salicylic acid (20)	Z. clinopodioides [80]	Effect on cardiovascular system reviewed [117] Pharmacological importance reviewed [118]
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]
(Z)-3-Hexen-1-ol benzoate (22)	Z. tenuior [94]	n.f.
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]
Phenethylalcohol glucoside (24)	Z. clinopodioides [4]	Weak inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4] Neuroprotective effect [122] Antiradical activity, weak ACE-inhibitory activity [124] Inhibition of osteoclast differentiation [125]
Eugenol (25)	Z. tenuior [94]	Insecticidal (against L. serricorne) [126] Acaricidal activity [127] Antibacterial [128] Inhibition of tyrosine kinase [129] Review on possible antidepressive activity [130] Review on antibacterial effect against cariogenic bacteria [131] Review on possible synergy of eugenol containing essential oils and eugenol (25) with antibiotics [132] Review on antioxidative effect [133] General properties reviewed here [134]