Table 3.

Mono and sesquiterpenic substances isolated from Kazakhstan Ziziphora species (N.f.—not found).

Monoterpenes
Name of Compound and ID	Isolation/Detection in Kazakhstan spp. of Ziziphora (Percentage Content when Given)	Biological Activity	Chemical Structure
Myrcene (syn. β-myrcene) (30)	Z. clinopodioides (0.6%–1.9%) [9,15,185]	Antibacterial, antitermitic, antifungal [187] Antioxidant (DPPH) [188] Some cytotoxic activity [189] Low fumigant activity against various species of insects [190,191] Sedative and motor relaxant effects in mice [192] Anti-inflammatory activity in the mouse model of pleurisy induced by LPS [193] Protective effect against t‑BOOH induced mutagenesis [194] Immunomodulatory and protective effects against the immunotoxicity induced by TCDD in rats [195]; antioxidant activity against TCDD‑induced oxidative stress in rats liver [196]; neuroprotective after global cerebral ischemia/reperfusion-mediated oxidative and neuronal damage in mouse [197] Gastroprotective effect against various ulcerogenic agents [198] Analgesic activity reviewed [199] Review on metabolism and toxicity [200]
	Z. clinopodioides subsp. rigida (0.2%) [21]
	Z. clinopodioides subsp. bungeana (0.3%) [201]
	Z. tenuior (0.1%) [179,202]
(Z)-β-Ocimene (31)	Z. clinopodioides (1.1%) [184]	Antibacterial [187] Antifungal (Candida strains, Cryptococcus neoformans, Epidermophyton floccosum, Microsporum canis and M. gypseum, Trychophyton mentagrophytes and T. verrucosum, Aspergillus flavus, A fumigatus, A. niger) [203,204]
	Z. clinopodioides subsp. bungeana [201]
(E)-β-Ocimene (32)	Z. clinopodioides (1.2%) [184]	Antifungal (Candida strains, Cryptococcus neoformans, Epidermophyton floccosum, Microsporum canis and M. gypseum, Trychophyton mentagrophytes and T. verrucosum, Aspergillus flavus, A fumigatus, A. niger) [203,204]
3,7-Dimethyl-1,3,7-octa-triene (33)	Z. tenuior [94]	n.f.
α-Thujene (34)	Z. clinopodioides (0.1%–1.2%) [15,184]	n.f.
	Z. clinopodioides subsp. rigida (0.1%) [21]
	Z. clinopodioides subsp. bungeana [201]
	Z. tenuior (0.48%) [94,179]
α-Phellandrene (35)	Z. clinopodioides (0.3%) [184]	Insecticidal activity against various species of insects [192,193]; larvicidal activity against various mosquito species [205,206] Antinociceptive activity assessed in various chemical‑induced nociception models in rodents [207,208] Antidepressant activity in rats [208] Induction of autophagy in human liver tumour cells [209]; induction of necrosis [210]; induction of apoptosis in mice leukaemia WEHI‑3 cells in vitro [211]; promotion of the immune response by increasing the level of T‑cells, monocytes and macrophages in BALB/c mice in vivo [212]
α-Terpinene (36)	Z. clinopodioides (2.0%) [184]	Inhibition of P-glycoprotein-mediated transport of different substances [213] Suppression of CNS in mice [214,215] Some topical anti-inflammatory activity in carrageenan‑induced paw edema in rats [216] Antioxidant activity in various free radical scavenging tests [217,218] Antifungal activity tested against some food spoilage yeasts [219] Larvicidal activity against mosquitoes Aedes aegypti and A. albopictus [206] Antiviral activity against herpes simplex virus type 1 in vitro [220] Review on some effects on cardiovascular system [221] Trypanocidal activity against Trypanosoma evansi [222]
	Z. clinopodioides subsp. rigida [21]
	Z. clinopodioides subsp. bungeana (0.1%) [201]
Terpinolene (37)	Z. clinopodioides (0.1%–0.2 %) [184]	Inhibition of P-glycoprotein-mediated transport of different substances [213] Anti-inflammatory (inhibition of NO production in LPS-stimulated RAW-264.7 macrophages) [223] Inhibition of acetylcholinesterase and butyrylcholinesterase [224] Suppression of CNS in mice [214,215,225] Antiproliferative (tested on primary rat neurons and N2a neuroblastoma cells) [226]; antiproliferative effect on K562 cells [227]; some cytotoxic activity [190]
	Z. clinopodioides subsp. rigida (0.5%) [21]
	Z. clinopodioides subsp. bungeana (0.1%) [201]
	Z. tenuior (0.19%) [94,179]
		Insecticidal activity against Callosobruchus chinensis and Sitophilus oryzae [228]; larvicidal activity tested against various mosquito species [205,206,229] Antioxidant activity in various free radical scavenging tests [217,218]; protective effect against LDL‑oxidation [230] Review on some effects on cardiovascular system [221] Antiviral activity against influenza A⁄PR⁄8 virus subtype H1N1 [231]
Limonene (38)	Z. tenuior (0.51%–7.82%) [232]	Insecticidal (against red imported fire ant) [233] Fumigation activity against stored-product pest insects [234] Anxiolytic effect in mice [225] Gastroprotective in rats [235] Pharmacological importance and properties reviewed [190,236,237] Analgesic activity reviewed [199] Review on some effects on cardiovascular system [221] Review on metabolism and toxicity [200]
	Z. clinopodioides [11,15]
p-Mentha-1(7,8)-diene (syn. pseudolimonene) (39)	Z. tenuior (0.04%) [179]	n.f.
p-Mentha-3,8-diene (40)	Z. tenuior (1.65%) [179]	n.f.
	Z. clinopodioides subsp. bungeana [201]
4-Methyl-1-(1-methyl-ethenyl)-cyclohexene (syn. 3,8-p-menthadiene) (41)	Z. tenuior [94]	n.f.
3-Methyl-6-(1-methyl-ethylidene)-cyclohexene (syn. Isoterpinolene, 2,4-p-menthadiene) (42)	Z. tenuior [94]	n.f.
3-Isopropenyl-5,5-di-methyl-cyclopentene (43)	Z. tenuior [94]	n.f.
Menthone (44)	Z. clinopodioides (6.2%–13.3%) [238]	Antifungal effect against C. albicans, synergy with fluconazol [239]; antimicrobial activity against tested strains of bacteria, yeast and pathogenic fungi [240,241] Insecticidal activity tested against various stored grain pests and vectors [242]; moderate insecticidal activity against Sitophilus zeamais [243] Antidepressant-like effects in an unpredictable chronic mild stress mouse model of depression [244]
Piperitone (45)	Z. clinopodioides (4.18%) [11]	Repellent activity against ants of the genus Crematogaster [245]; insecticidal activity against larvae of Spodoptera littoralis [246] and against Callosobruchus maculatus [247] Increase in antimicrobial activity of furazolidone and nitrofurantoin against bacteria of the family Enterobacteriaceae [248,249] Fungicidal activity against Aspergillus flavus [250]
	Z. clinopodioides subsp. rigida (1.4%) [21]
	Z. clinopodioides subsp. bungeana (0.6%) [201]
Piperitenone (46)	Z. clinopodioides (5.3%) [11]	Antibacterial activity against 52 Gram-positive and Gram-negative bacterial species, disc diffusion method [11] Insecticidal activity against Sitophilus zeamais [243]
	Z. clinopodioides subsp. rigida (17.4%) [21]
p-Menth-4-en-3-one (47)	Z. tenuior (0.5%) [202]	n.f.
Piperitone oxide (48)	Z. persica (0.32%) [251]	Antibacterial activity against 19 Gram-positive and Gram-negative bacterial species [252]
Piperitenone oxide (49)	Z. clinopodioides (0.16%) [11]	Antimicrobial activity against strains of bacteria, yeast and pathogenic fungi [241,252] Insecticidal activity against the West Nile virus mosquito Culex pipiens larvae [253] and against various stages of Anopheles stephensi [254] Antinociceptive activity in acetic acid‑induced writhing test and in the second phase of formalin test [255] Antiviral activity against herpes simplex virus type 1 [256]
Verbenone (50)	Z. clinopodioides subsp. rigida (0.2%) [21]	Antifungal activity against Botrytis cinerea [257] Fumigation activity against stored-product pest insects [234] Insecticidal activity against Acanthoscelides obtectus [258]
2-Acetyl-4,4-dimethyl-cyclopent-2-enone (51)	Z. tenuior (2.49%) [94]	n.f.
2-Isopropyl-5-methyl-3-cyclohexen-1-one (52)	Z. tenuior [94], Z. tenuior (1.6%) [179]	n.f.
Pulegone (53)	Z. tenuior (86.29%–87.06%) [259]	Insecticidal [260] Fumigation activity against stored-product pest insects [234] Anti-inflammatory activity reviewed [261] Analgesic activity reviewed [199] Review on metabolism and toxicity [200]
	Z. clinopodioides (45.8%) [21]
3-Methyl-6-(1-methyl-ethenyl)-2-cyclohexen-1-one (syn. Isopiperitenone) (54)	Z. tenuior (0.3%–1%) [94,259]	n.f.
Carvotanacetone (55)	Z. tenuior [94]	Cytotoxic activity against MCF‑7 and Hep‑G2 cells [262] Antifungal activity against tested phytopathogenic fungi [263]
Menthol (56)	Z. clinopodioides (9.13%) [11]	Antifungal effect against Candida albicans, synergy with fluconazol [239] Fumigant activity [264] Analgesic, antifungal, antibacterial, antipruritic, anticancer, anti-inflammatory, antitussive, antiviral, insecticidal activity reviewed in Kamatou et al. [265] Gastroprotective effect in gastric ulcers induced by ethanol or indomethacin in Wistar male rats and also antidiarrheal and antiperistaltic effect; anti-apoptotic, antioxidant and anti-inflammatory activities [266,267] Allosteric modulation of human α3β4 nicotinic acetylcholine receptors [268] Analgesic activity reviewed [199] Review on some effects on cardiovascular system [221] Review on metabolism and toxicity [200]
	Z. clinopodioides subsp. rigida (0.1%) [21]
Menthofuran (57)	Z. tenuior (0.1%) [182]	Acetyl and butyrylcholinesterase inhibitory activity [269]
Neomenthol (58)	Z. clinopodioides subsp. rigida (2.1%) [21]	Antibacterial activity against Escherichia coli [270] Acaricidal activity against Tyrophagus putrescentiae [271] Sedative in the pentobarbital‑induced sleep test in mice [272]
	Z. clinopodioides subsp. bungeana [201]
Neo-iso-menthol (59)	Z. clinopodioides subsp. bungeana (0.3%) [201]	n.f.
	Z. clinopodioides (0.12%–0.25%) [15]
Menthyl acetate (60)	Z. clinopodioides (0.1%) [184]	n.f.
Isomenthyl acetate (61)	Z. clinopodioides subsp. rigida (0.5%) [21]	n.f.
Thymol (62)	Z. clinopodioides (0.17%–53.6%) [15,184]	Antibacterial (Bacillus cereus, Micrococcus flavus, S. aureus, Listeria monocytogenes, E. coli, P. aeruginosa, Proteus mirabilis, Salmonella typhimurium) [261,273,274] Antifungal (Trichophyton mentagrophytes, T. interdigitale, T. rubrum, T. erinaceum, T. soudanense, T. violaceum, Microsporum canis, M. gypseum, Epidermophyton flocosum, A. fumigatus, Scopulariopsis brevicaulis, Scytalidium dimidiatum, C. albicans, Cryptococcus neoformans, Malassezia pachydermatis [273]); against Botrytis cinerea [275]; against Penicillium funiculosum and P. ochrochloron, Aspergillus fumigatus, A. niger, A. flavus, A. ochraceus, C. albicans, Trichoderma viride) [187]; antifungal (Candida albicans, C. tropicalis, Saccharomyces cerevisiae, Cryptococcus neoformans, Microsporum gypseum, Trichophyton rubrum, T. mentagrophytes), antimicrobial (E. coli, P. aeruginosa, Yersinia enterocolitica, Salmonella enteritidis) activity [276]; antifungal (yeasts, dermatophyte and Aspergillus strains) [277] Antifungal activity against various Candida strains and synergy with fluconazole [278] Review on possible synergy of 62 containing essential oils and thymol (62) with antibiotics [132] Antileshmanial (against L. chagasi) [279] Antimalarial (P. falciparum) [280] Low antinematocidal activity [281] Antiviral (HSV-1) [282] Cytotoxic (HeLa, B16, MCF-7, 3T3, MRC-5 cells) [283]; against P815 and PBMC [284]; induction of apoptosis [285]; cytotoxic effects on acute promyelotic cancer cell line HL‑60 [286]
	Z. clinopodioides subsp. rigida (8%) [21]
	Z. tenuior [94]
		Anti-genotoxic (bleomycin-induced DNA damage) [287] Anti-inflammatory activity in carrageenan-induced paw edema, MPO activity and peritonitis in rats [288]; anti-inflammatory activity in LPS‑stimulated mouse mammary epithelial cells via inhibition of the NF‑κB and MAPKs signalling pathways [289]; anti-inflammatory effect in ovoalbumin‑induced mouse asthma, possibly through inhibiting NF‑κB activation [290]; inhibition of S. aureus internalization into bovine mammary epithelial cells by inhibiting NF-κB activation [291] Review on anti-inflammatory, antioxidant, and immunological effects [292] Protective effect on radiation‑induced apoptosis in Chinese hamster lung fibroblast V79 cells [293]; DNA‑protective effects against H2O2-induced DNA lesions in human hepatoma HepG2 cells [294]; hepatoprotective effect against t‑BHP‑induced oxidative damage in Chang liver cells [84]; protective effect against cisplatin‑induced nephrotoxicity in rats [295]; protective effect against UVA‑ and UVB‑induced lipid peroxidation in NCTC 2544 cell line [296]; antioxidant [273,297,298,299] Review on some effects on cardiovascular system [221] Gastroprotective effects in the acute and chronic ulcer models in rats [300] Positive allosteric modulator of the GABAA receptors in primary cultures of mouse cortical neurons [301] Anti-hyperglycemic and anti-hyperlipidemic activity in high fat‑induced type 2 diabetic C57BL/6J mice [302] and protective effect in nephropathy [303] Analgesic activity reviewed [199] Review on metabolism and toxicity [200]; general review on thyme and 62 [304]
cis-Sabinene hydrate (63)	Z. clinopodioides (0.3%–2.2%) [184]	Antiviral (HSV-1) [282]
	Z. clinopodioides subsp. bungeana [201]
trans-Sabinene hydrate (64)	Z. clinopodioides subsp. rigida (0.1%) [21]	Antiviral (HSV-1) [282] Moderate repellent (against tick Amblyomma americanum) [305]
	Z. tenuior [94]
p-Menth-3-en-8-ol (65)	Z. clinopodioides (2.7%) [185]	n.f.
	Z. clinopodioides subsp. rigida (12.5%) [21]
	Z. tenuior (53.97%) [179]
Linalool (66)	Z. clinopodioides (1.8%–7.9%) [184]	Antibacterial [128,187,306] Antimycotic (Candida albicans) [307], against M. ramamnianus [308] Repellent against mosquitoes [309] Molluscicidal (against snail Oncomelania hupensis) and cercarcicidal (against Schistosoma japonicum) [310] Anti-inflammatory (in carrageenan‑induced edema and inhibition of hyperalgesia induced by L‑glutamate and prostaglandin E2 in rats) [311]; anti-inflammatory (through inhibition of the expression of TNF-α and IL-6 in LPS-stimulated RAW 264.7 cells) [312]; anti-inflammatory (in cigarette smoke-induced ALI in mice through inhibiting NF‑κB activation) [313] Cytotoxic (human amelanotic melanoma cell line C32, renal cell adenocarcinoma ACHN, hormone-dependent prostate carcinoma LNCaP) [314]; induction of apoptosis (variety of human leukaemia cells) [315,316,317] Hypocholesterolemic (through inhibition of HMG-CoA reductase and conversion of lanosterol to cholesterol) [318,319] Protective effect against t‑BOOH induced mutagenesis [194] Review on some effects on cardiovascular system [221] Sedative and anxiolytic [320]; antidepressant [321]; GABAA receptor modulation [322] Analgesic activity reviewed [199] Review on metabolism and toxicity [200]
	Z. clinopodioides subsp. rigida [21]
Borneol (67)	Z. clinopodioides (0.9%–1.2%) [184]	Inhibition of nicotinic acetylcholine receptor [323] DNA-protective effects against H2O2 in primary rat hepatocytes and testicular cells [324] Anti-inflammatory in an ALI model in mice through inhibition of the NF-κB and MAPKs signalling pathways [325]; suppression of expression of IL‑1β and IL‑6 in TNBS‑induced colitis in mice [326] Penetration enhancer [327]; increasing of the brain bioavailability of different drugs [328] Antibacterial (multi-drug resistant E. coli) [329] Antiviral (HSV-1) [282]
endo-Borneol (68)	Z. tenuior (0.14%) [202]	Vasorelaxant effect on rat thoracic aorta artery rings [330] Positive modulation of the activation of GABAA receptors [331] Potentiation of SeC-induced apoptosis in human hepatocellular carcinoma cells [332] Prolonging anaesthesia time of propofol by inhibiting its glucuronidation [333]
Bornyl acetate (69)	Z. clinopodioides (3.3%) [184]	Antifungal (against Pyrenophora avenae) [334] Insecticidal (against Callosobruchus chinensis and Sitophilus oryzae) [228] Anti-inflammatory in an ALI model in mice [335] and in human chondrocytes [336] Antiabortive in pregnant mice [337] Cytotoxic ((Eca-109, HepG2, HT29, MDA-MB-231, PC-3, SGC7901, SW1990 and U2-OS) and a normal cell line (HL-7702) [338]
Terpinen-4-ol (70)	Z. clinopodioides (0.36%–18.2%) [15,184]	Sedative and anaesthetic (on silver catfish juveniles) [339]; depressant effect on the CNS and significant anticonvulsant activity probably due to interaction with GABA receptors [340,341] Low inhibition of acetylcholinesterase and butyrylcholinesterase [224] Relaxant effect on vascular smooth muscle [342] Review on some effects on cardiovascular system [221] Anticancer (melanoma) [343]; antiproliferative activity in two murine cancer cell lines through induction of necrosis and cell cycle arrest [344]; induction of apoptosis in human non-small cell lung cancer [345]; anti-tumoral activity in human melanoma cells by induction of caspase-dependent form of apoptosis [346] Antiviral activity against influenza A⁄PR⁄8 virus subtype H1N1 [231] Anti-inflammatory (inhibition of NO production in LPS-stimulated RAW-264.7 macrophages) [223]; anti-inflammatory [216]; anti-inflammatory activity in a murine model of oral candidiasis [347]; suppression of the production of TNFα, IL‑1β, IL‑8, IL‑10 and PGE2 by LPS‑activated monocytes [348] Antibacterial against MRSA and CoNS [349] Low antinematocidal activity [281] Antimycotic (C. albicans) [307,350] Insecticidal (against L. serricorne) [351] Trypanocidal activity against Trypanosoma evansi [222]
	Z. clinopodioides subsp. rigida (0.4%) [21]
	Z. clinopodioides subsp. bungeana (0.6%) [201]
	Z. tenuior (0.08%) [202]
α-Terpineol (71)	Z. clinopodioides (0.3%–5.3%) [184]	Antifungal [187,350,352], antimicrobial activity [306] Antiviral activity against influenza A⁄PR⁄8 virus subtype H1N1 [231] Enhancement of GABA modulation [353] Anticancer (melanoma cells) [343] Insecticidal (against L. serricorne) [351] Inhibition of the acetic acid-induced writhing and formalin-induced nociception in mice [354] Analgesic activity reviewed [199] Review on metabolism and toxicity [200]
1,8-Cineol (72)	Z. clinopodioides (5.4%–21.6%) [185]	Antimicrobial activity (MDR resistant bacteria) [355] Hypocholesterolemic (through inhibition of HMG‑CoA reductase and conversion of squalene to lanosterol [319] Analgesic activity reviewed [199] Review on some effects on cardiovascular system [221] Review on metabolism and toxicity [200]
Carvacrol (73)	Z. clinopodioides (8.7%) [184]; Z. clinopodioides (52.7%) [183]	Antifungal (Penicillium funiculosum and P. ochrochloron, Aspergillus fumigatus, A. niger, A. flavus, A. ochraceus, C. albicans, T. viride) [187,273,277] Antibacterial (B. cereus, M. flavus, S. aureus, L. monocytogenes, E. coli, P. aeruginosa, P. mirabilis, S. typhimurium) [273,274]; against B. cinerea [275]; active against food spoilage microorganisms [356,357,358] Low antinematocidal activity [281] Antileishmanial (against L. chagasi) [279] Antiviral (HSV-1) [283]; antiviral activity on enteric viruses [359] Review on synergic effect with antibiotics [132] Cytotoxic (HeLa, B16, MCF-7, 3T3, MRC-5 cells) [284]; against P815 and PBMC [284]; antiproliferative effects on a human metastatic breast cancer cell line, MDA‑MB 231 [360]; induction of apoptosis in HL‑60 and Jurkat cells by mitochondria‑mediated pathway through the involvement of caspase‑3 [361] Cytotoxic effect on the intestinal cell line Caco‑2 [362]; inhibition of growth of N‑ras oncogene transformed mouse myoblast cells [363] DNA‑protective effects against H2O2-induced DNA lesions in human hepatoma HepG2 cells [295]; antioxidant [273,297,299] Anti-inflammatory (inhibition of NO production in LPS-stimulated RAW-264.7 macrophages) [223]; anti-inflammatory effect by reducing the production of IL‑1β and prostanoids, possibly through the induction of IL‑10 release [364] Anti-genotoxic [287] Anxiolytic, GABAA receptor modulation [322,365] Bronchodilatory effect in guinea pigs [366] Antinociceptive activity in mice in the acetic acid-induced abdominal constriction, formalin and hot-plate tests [367] Acetyl‑ and butyrylcholinesterase inhibitory activity [269,368] Analgesic activity reviewed [199] Review on anti-inflammatory, antioxidant, and immunological effects [292] Review on some effects on cardiovascular system [221] General reviews on 73 [369,370]
	Z. tenuior [94]
2-Methyl-5-(1-methyl-ethyl)phenol acetate (syn. carvacryl acetate) (74)	Z. tenuior [94]	Anthelmintic Haemonchus contortus [371] Anti-inflammatory effect through inhibition of edema induced by carrageenan, histamine, serotonin or PGE2 [372] Anxiolytic-like effect probably through acting on the GABAergic system [373,374]
trans-p-Mentha-2,8-di-enol (syn. trans-Isopiperitenol) (75)	Z. tenuior [94]	n.f.
cis-Verbenol (76)	Z. clinopodioides subsp. rigida (0.1%) [21]	Antibacterial (multi-drug resistant E. coli) [329] Insecticidal activity (against Lasioderma serricorne) [351] GABAA receptor modulation [322] Repellent activity against Anopheles gambiae [375] Anti-ischemic and anti-inflammatory activity [376]
trans-Verbenol (77)	Z. clinopodioides subsp. rigida (0.1%) [21]	Antibacterial (multi-drug resistant E. coli) [329] GABAA receptor modulation [322]
Cuminyl aldehyde (syn. cumaldehyde) (78)	Z. clinopodioides subsp. rigida (0.8%) [21]	Tyrosinase inhibitory activity [377] Suppression of melanin formation in cultured murine B16‑F10 melanoma cells [378]
	Z. clinopodioides (0.12%–0.24%) [15]
Ziziphoroside A (79)	Z. clinopodioides [4]	Weak inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4]
Ziziphoroside B (80)	Z. clinopodioides [4]	Weak inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4]
Ziziphoroside C (81)	Z. clinopodioides [4]	Weak inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4]
Schizonepetoside C (82)	Z. clinopodioides [4]	Weak inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4]
Schizonepetoside A (83)	Z. clinopodioides [4]	Some inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4]
9-O-Glucopyranosyl-p-menthan-3-one (84)	Z. clinopodioides [4]	Weak inhibitory activity on NO production stimulated by LPS and IFN-γ in RAW 264.7 cells [4]
4aα,7α,7aα-Nepeta-lactone (85)	Z. tenuior (0.5%) [94,179]	Some activity against Helicobacter pylori [379] and repellent activity against mosquitoes [380]
Sesquiterpenes
Name of Compound and ID	Isolation/Detection in Kazakhstan spp. of Ziziphora (Percentage Content When Given)	Biological Activity	Chemical Structure
Germacrene B (86)	Z. clinopodioides (1.1%) [11]	n.f.
Germacrene D (87)	Z. clinopodioides (0.24%–4.0 %) [15,184]	Effective aphid repellent [381]
	Z. clinopodioides subsp. rigida (1.1%) [21]
	Z. tenuior (0.13%) [94,179]
	Z. clinopodioides subsp. bungeana (0.3%) [201]
Bicyclogermacrene (88)	Z. clinopodioides (0.6%) [185]	Low antibacterial effect (S. aureus, B. cereus, A. baumanii, E. coli, P. aeruginosa) [382]
	Z. clinopodioides subsp. bungeana (0.1%) [201]
β-Bisabolene (89)	Z. clinopodioides (0.2%) [184]	Synergistic antibacterial activity with ampicillin against strain of S. aureus [383]
	Z. tenuior [94]
Caryophyllene oxide (β-caryophyllene oxide) (90)	Z. clinopodioides (0.5%) [184]	Antitermitic [187], antifungal [308,384], antimicrobial [385] Analgesic and anti‑inflammatory activity in tested mice [386] Modest cytotoxic activity against tested human tumor cell lines [387] Anti-cancer effects through the modulation of the PI3K/AKT/mTOR/S6K1 and MAPK signalling [388]
	Z. tenuior (0.11%–0.32%) [94,179,202]
Caryophyllene (syn. β-caryophyllene, trans-caryophyllene, (E)-caryophyllene) (91)	Z. tenuior (0.22%) [94,179]	Antifungal, antibacterial [187] Antiprotozoal (T. cruzi, L. infantum) [389] Fumigant against Lasioderma serricorne [390] Antihyperglycemic effect by decreasing blood glucose and increasing plasma insulin in diabetic rats [391] Antioxidant effect and inhibition of 5‑lipoxygenase in CCl4‑induced fibrosis in rats [392] Anti-inflammatory effect through the inhibition of TNFα and PGE2 and it is also effective in reducing PAF‑, bradykinin‑, ovoalbumin‑induced mouse paw edema [393,394] Low inhibition of acetylcholinesterase and butyrylcholinesterase [224] Review on metabolism and toxicity [200]
α-Humulene (syn. α-Caryophyllene) (92)	Z. clinopodioides (2.7%–4.5%) [184]	Antibacterial activity against Propionibacterium acnes (MIC of 3.13 μg/mL) [395] Antiproliferative activity against several cancer cell lines (MCF-7, PC-3, M4BEU, CT-26, human amelanotic melanoma cell line C32, renal cell adenocarcinoma ACHN, hormone-dependent prostate carcinoma LNCaP, A-549 and human colon adenocarcinoma cell line DLD-1) [396,397,398,399,400,401] Anti-inflammatory effect through the inhibition of TNFα, IL‑1β and PGE2 and it is also effective in reducing PAF‑, bradykinin‑, ovoalbumin‑ and histamine‑induced mouse paw edema [393,394]
δ-Cadinene (93)	Z. tenuior [94]	Antimicrobial activity against Streptococcus pneumoniae strains resistant to β-lactamic antimicrobials (MIC of 31.25 μg/mL) [402] Antibacterial activity against Propionibacterium acnes (MIC of 3.13 μg/mL) [395] Antileishmanial effect against L. donovani [403]
τ-Cadinol (94)	Z. tenuior [94]	Weak antimite activity against Dermatophagoides pteronyssinus [404] Good antifungal activity against brown rot fungi Laetiporus sulphureus and weak antifungal activity against white rot fungi Coriolus versicolor [405] Anti-wood-decay fungal activity [274,406]
Patchouli alcohol (95)	Z. clinopodioides (0.1%–1.04 %) [15]	Anti-inflammatory activity through inhibition of over-expression of iNOS and IL-6 in LPS-stimulated RAW264.7 and TNF-α HT-29 cells [407,408]; anti-inflammatory effect in vivo in rats [409] Gastroprotective [410] Review on metabolism and toxicity [200]
(Z)-6,10-dimethyl-5,9-undecadien-2-one (syn. Z-geranylacetone, nerylacetone) (96)	Z. tenuior [94]	n.f.
Cyclohexane, 1-ethenyl-1-methyl-2-(1-methylethenyl)-4-(1-methylethylidene) (97)	Z. tenuior [94]	n.f.
Spathulenol (98)	Z. tenuior [94]	Antimicrobial activity against S. aureus and P. mirabilis [385]
Bicyclo[5.2.0]no-nane, 2-methylene-4,8,8-tri-methyl-4-vinyl (99)	Z. tenuior [94]	Antimicrobial, anti-inflammatory, antihyperlipidemic, antioxidant activities [411] Repellent activity against Tribolium castaneum and Myzus persicae [412]
2-Methylene-6,8,8-trimethyl-tricyclo-[5.2.2.0(1,6)]undecan-3-ol (100)	Z. tenuior [94]	n.f.
Ar-turmerone (101)	Z. tenuior [94]	Significant repellent action against Sitophilus zeamais and toxic effect against Spodoptera frugiperda [413]; insecticidal activities against Nilaparvata lugens and Plutella xylostella [414] Inhibition of platelet aggregation induced by collagen (IC50, 14.4. μM) and arachidonic acid (IC50, 43.6. μM) and no effect on PAF and thrombin-induced platelet aggregation on washed rabbit platelets [415]; anti-inflammatory effects through blocking of NF-κB, JNK and p38 MAPK signalling pathways in amyloid β-stimulated microglia [416] Review on activity [417]