Sesquiterpene Lactones from Artemisia Genus: Biological Activities and Methods of Analysis

Table 1

Summary of HPLC conditions for sesquiterpene lactones.

Sample	Extraction, derivatization	Detected sesquiterpene lactones	Detection	Chromatographic conditions	Reference
Sandy, clayey, and humic soil	(i) Supercritical fluid extraction (SFE); (ii) Supercritical fluid: CO2(iii) Extraction time: 20 minutes; (iv) Precolumn derivatization (0.2% NaOH, 50°C, 30 min, then acidified 0.08 M acetic acid)	Artemisinin	UV, 260 nm	(i) Column: C18 Bio Wide Pore (25 cm 4.6 mm, 5 μm); (ii) Column temperature: 30°C; (iii) Elution type: isocratic; (iv) The mobile phase: methanol/acetonitrile/0.9 mM Na2HPO4–3.6 mM NaH2PO4 buffer (pH 7.76) solution (45/10/45 v/v/v); (v) Injection volume: 20 μL; (vi) Flow rate: 1 mL/min; (vii) Retention time: 7.5 min	[154]
A. santonicum L.,; A. taurica Willd.,; A. spicigera K. Koch,; A. herba-alba Asso,; A. haussknechtii Boiss.,; A. campestris L.,; A. araratica Krasch.,; A. armeniaca Lam.,; A. austriaca Jacq., and; A. abrotanum L.	(i) Extraction with n-hexane at room temperature for 2 days with a laboratory-scale shaker; (ii) Precolumn derivatization (0.2% NaOH, 50°C, 30 min, then acidified 0.08 M acetic acid)	Artemisinin	DAD, 254 nm	(i) Column: ACE-5 C18 column (250 4.6 mm, 5 μm); (ii) Column temperature: 30°C; (iii) Elution type:  isocratic; (iv) The mobile phase: formic acid (0.2% v/v) : acetonitrile (50 : 50 v/v); (v) Flow rate: 1 mL/min.; (vi) Retention time: 5.58 min	[155]
Artemisia annua L	(i) Extraction in Soxhlet extractor with petroleum ether (30–60°C) for 6 h; (ii) Precolumn derivatization (0.2% NaOH, 45°C, 30 min, and then acidified 0.08 M acetic acid)	Artemisinin	UV, 260 nm	(i) Column: RP-C18 silica column (250 4.6 mm, 5 μm); (ii) Column temperature: 30°C; (iii) Elution type: isocratic; (iv) The mobile phase: methanol/acetonitrile/0.9 mM Na2HPO4–3.6 mM NaH2PO4 buffer (pH 7.76) solution (45/10/45 v/v/v); (v) Injection volume: 10 μL; (vi) Flow rate: 0.5 mL/min; (vii) Retention time: 16.85 min	[156]
A. absinthium leaves	(i) Extraction with various solvent types: 100% methanol, 75% methanol, 50% methanol, 25% methanol, 75% acetonitrile in a thermostatic rotary shaker, and various temperatures (30–60°C) for various time intervals; (ii) Precolumn derivatization (0.25% NaOH, 50°C, 1 hour and then being acidified with 0.2 M acetic acid solution)	Anabsinthin and derivatized artemisinin	DAD, 205 and 258 nm	(i) Column: C8 (250 mm 4.6 mm, 5 μm); (ii) Column temperature: 30°C; (iii) Flow rate: 1 mL/min; (iv) Elution type: gradient elution: 90% A/10% B, hold for 5 min, to 60% B in the next 13 min; (v) The mobile phase: A: methanol/0.1% trifluoroacetic acid (TFA) (15/85), B: methanol/0.1% TFA (85/15); (vi) Artemisinin not detected	[157]
A. annua leaves	(i) Dipping dried leaves in 100% chloroform, 8 s; (ii) Precolumn derivatization (0.2% NaOH and then acidified with 0.08 M acetic acid solution)	Artemisinin	260 nm	(i) Column: RP-C18 silica column (250 4.6 mm); (ii) Elution type:  isocratic; (iii) The mobile phase: methanol/acetonitrile/0.9 mM Na2HPO4–3.6 mM NaH2PO4 buffer (pH 7.76) solution (45/10/45 v/v/v); (iv) injection volume: 1 μL	[158]
A. annua leaves	(i) Solid phase extraction; (ii) Liquid-liquid extraction method; (iii) Purification procedures	Artemisinin	IR	(i) Column: LC-CN column (25 mm 4 mm 5 μm); (ii) Column temperature: 35°C; (iii) Elution type:  isocratic; (iv) The mobile phase: methanol : water (60 : 40 v/v); (v) Injection volume: 20 μL; (vi) Flow rate: of 1 mL/min; (vii) Retention time: 6.932 min	[159]
A. annua	Extraction by refluxing with hexane at 75°C for 1 hour	Artemisinin	ELSD	(i) Column: C18-RP (250 mm × 4.0 mm, 5 μm); (ii) Column temperature: room temperature; (iii) Elution type:  isocratic; (iv) The mobile phase: water adjusted to pH 3.0–3.5 with trifluoroacetic acid (TFA) : acetonitrile (65 : 35); (v) Flow rate: 1.0 mL/min; (vi) Retention time: 7.63 min	[138]
A. herba alba and A. monosperma aerial parts	Extraction in Soxhlet extractor with methanol at 60°C	α, β-Dihydroartemisinin, dihydroartemisinic aldehyde, arteannuin B, dihydroartemisinic acid, dihydroartemisinic alcohol, artemisitene, artemisinin, and artemisinic acid	HPLC-DAD (215, 254, 294, and 334 nm), LC-positive mode ESI-MSn	(i) Column: C18 column (50 mm 2.1 mm, 1.8 μm); (ii) Column temperature: 30°C; (iii) Elution type: gradient, 0 min—A : B 10 : 90; 36 min—A : B 100 : 0; 40 min—A : B 100 : 0; (iv) The mobile phase: A: methanol, B: 0.2% formic acid; (v) Injection volume: 10 μL; (vi) Flow rate: 0.2 mL/min; (vii) Retention time: 12.4 min α-dihydroartemisinin, 12.8 min β-dihydroartemisinin, 15.2 min dihydroartemisinic aldehyde, 15.5 min arteannuin B, 15.7 min dihydroartemisinic acid, 18.8 min dihydroartemisinic alcohol, 36.6 min artemisitene, 37.7 min artemisinin, and 23.7 min artemisinic acid	[160]
A. annua	(i) Extracted twice with scintanalyzed toluene in a ultrasonic bath, in ice-cold water, for 30 minutes; (ii) Precolumn derivatization	Artemisinin	260 nm	(i) Column: C-18 column (15 cm 4.6 mm, 5 μm); (ii) Elution type: isocratic; (iii) The mobile phase: 0.01 M sodium phosphate buffer: methanol [55 : 45 (v/v)] pH 7.0; (iv) Flow rate: 1 mL/min; (v) Retention time: 12.0 min	[161]
A. annua leaves	Extraction in Soxhlet extractor with petroleum ether : n-hexane (2 : 1) for 4 hours	Artemisinin	DAD, 258 nm	(i) Column: C8 (250 4.6 mm, 5 μm); (ii) Column temperature: 30°C; (iii) Elution type: gradient, 5 min—70% A: 30% B to 60% B in the next 13 min; (iv) The mobile phase: A: 0.9 mM Na2HPO4, 3.6 mM NaH2PO4 buffer (pH 7.76); B: acetonitrile; (v) Injection volume: 20 μL; (vi) Flow rate: 1 mL/min; (vii) Retention time: 6.476 min	[136]
A. annua leaves	(i) Sonication with toluene; (ii) Precolumn derivatization (0.2% NaOH, 50°C, 45 min and then acidified 0.2 M acetic acid)	Artemisinin	DAD, 258 nm	(i) Column SB C18 column (150 4.6 mm) 5 μm; (ii) Elution type: isocratic; (iii) The mobile phase: 45% (v/v) methanol and 55% 0.01 M sodium phosphate buffer (pH7.0); (iv) Flow rate: 1 mL/min; (v) Retention time: 12 min	[162]
A. annua L leaves, flower buds, stems, and roots	(i) Room temperature extraction; (ii) Heat-reflux extraction at 50°C; (iii) Soxhlet extraction at 50°C; (iv) MAE (microwave-assisted extraction); (v) Solvent: petroleum ether : acetone (4 : 1, v/v)	Artemisinin	ELSD	(i) Column: RP-C18 column (150 mm × 4.6 mm i.d., 5 μm); (ii) Column temperature: 30°C; (iii) Elution type: isocratic; (iv) The mobile phase: water : acetonitrile (40 : 60 v/v); (v) Injection volume: 10 μL; (vi) Flow rate: 1 mL/min; (vii) Retention time: 9 min	[113]
A. annua L	Extraction with methanol by sonication, 45 minutes	Artemisinin	LC-MS with SIM	(i) Column: ODS3 column (250 4.6 mm, 5 μm); (ii) Elution type: gradient, 72% B for 6 min, and it was then increased to 100% B in 1 min; (iii) The mobile phase: water (0.1% formic acid) and (B) acetonitrile; (iv) Injection volume: 2 L; (v) Flow rate: 1.2 mL/min; (vi) 265.3	[163]
A. annua seeds, aerial parts	Extraction in Soxhlet extractor with methanol, 60°C	Artemisinin	HPLC/DAD; 214, 217, 280, and 290 nm; HPLC-positive mode ESI-MS	(i) Column: SB-C18 column (150 mm 4.6 mm i.d., 1.8 μm); (ii) Column temperature: 30°C; (iii) Elution type: gradient, 0 min, A : B 10 : 90; 36 min, A : B 70 : 30; 50 min, A : B 100 : 0; 60 min; (iv) The mobile phase: (A) methanol and (B) 0.2% formic acid; (v) Flow rate: 0.8 mL/min; (vi) Retention time: 35.2 min	[140]
A. annua L	Maceration with dichloromethane or hexane, at room temperature, for 72 hours	Artemisinin	HPLC-DAD (210 nm), HPLC-MS; (API electrospray)	(i) Column: RP-18 column (250 mm 4.6 mm i.d., 5 μm); (ii) Column temperature: 26°C; (iii) Elution type: isocratic; (iv) The mobile phase: water adjusted to pH 3.2 by formic acid (A), and acetonitrile (B) 50% A : 50% B; (v) Injection volume: 20 μL; (vi) Flow rate: 1.3 mL/min; (vii) Retention time: 15.1 min	[153]
A. annua L	Extraction with different solvents and mixtures: n-hexane, isopropyl alcohol, ethanol, toluene by maceration, percolation, or; decoction, at low temperatures and vigorous shaking	Artemisinin, arteannuin, and artemisitone	RP-HPLC/refraction index	(i) Column: RP-C18 column (100 mm 4 mm i.d., 3 μm); (ii) Column temperature: room temperature; (iii) Elution type:  isocratic; (iv) The mobile phase: methanol (80–90%), water; (v) Injection volume: 100 L; (vi) Flow rate: 0.5 mL/min; (vii) Retention time: 1.7 min (arteannuin), 2 min (artemisinin), and 5.3 min (artemisitone)	[142]