Characterization of hepatoprotective metabolites from <i>Artemisia annua</i> and <i>Cleome droserifolia</i> using HPLC/PDA/ESI/MS–MS

El-Askary, Hesham; Handoussa, Heba; Badria, Farid; El-Khatib, Ahmed H.; Alsayari, Abdulrhman; Linscheid, Michael W.; Abdel Motaal, Amira

doi:10.1016/j.bjp.2018.10.001

Hesham El-Askary

Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Cairo, Egypt

http://orcid.org/0000-0001-7764-6588

Heba Handoussa

Department of Pharmaceutical Biology, Faculty of Pharmacy and Biotechnology, German University in Cairo (GUC), Cairo, Egypt

http://orcid.org/0000-0001-5552-1725

Farid Badria

Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt

http://orcid.org/0000-0001-8596-5589

Ahmed H. El-Khatib

Department of Chemistry, Humboldt-Universität zu Berlin, Berlin, Germany

Pharmaceutical Analytical Chemistry Department, Faculty of Pharmacy, Ain Shams University, Cairo, Egypt

http://orcid.org/0000-0002-2012-5893

Abdulrhman Alsayari

Department of Pharmacognosy, College of Pharmacy, King Khalid University, Abha, Saudi Arabia

http://orcid.org/0000-0002-5479-9319

Michael W. Linscheid

Department of Chemistry, Humboldt-Universität zu Berlin, Berlin, Germany

http://orcid.org/0000-0002-8902-1734

Amira Abdel Motaal ^** Corresponding author. E-mail:aabdulmtaal@kku.edu.sa (A. Abdel Motaal).

Department of Pharmacognosy, College of Pharmacy, King Khalid University, Abha, Saudi Arabia

Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Cairo, Egypt

http://orcid.org/0000-0002-1020-9954

* Corresponding author. E-mail:aabdulmtaal@kku.edu.sa (A. Abdel Motaal).

Authors' contributions

HE and AAM contributed in collecting plant samples and extract preparation. AHE and MWL performed qualitative chemical profiling of the phytoconstituents. HH and AA carried out the data analysis. FB carried out the in vitro assays. HE and AAM designed the study and contributed to the critical reading of the manuscript. All authors read and approved the final manuscript.

Conflicts of interest

The authors declare no conflicts of interest.

Groups	Treatment	% HepG-2 viability
1	Control (untreated)	100
2	CCl₄	35.23 ± 0.24
3	CCl₄ + Cl-AQ	86.43 ± 0.40
4	CCl₄ + ART-CQ	79.32 ± 1.54
5	CCl₄ + FEN-SaP	63.22 ± 2.1
6	CCl₄ + RO-MC	58.31 ± 0.73
7	CCl₄ + Lin-LRF	42.82 ± 1.15

Groups	Treatment	AST (IU/dl)	ALT (IU/dl)	Protein (g/dl)
1	Control (untreated)	36.8 ± 4.25	14.5 ± 3.36	7.12 ± 0.45
2	CCl₄	87.5 ± 4.34	34.1 ± 8.12	2.62 ± 4.14
3	CCl₄ + Cl-AQ	39.6 ± 5.41	20.4 ± 6.91	6.4 ± 0.22
4	CCl₄ + ART-CQ	40.8 ± 2.14	24.5 ± 3.11	5.18 ± 0.24
5	CCl₄ + FEN-SaP	52.8 ± 1.82	34.7 ± 2.33	4.15 ± 0.71
6	CCl₄ + RO-MC	65.3 ± 1.41	40.2 ± 1.41	4.01 ± 1.52
7	CCl₄ + Lin-LRF	69.3 ± 2.11	45.1 ± 2.12	3.51 ± 0.45

Peak (compound)	Identified compounds	Retention time (min)	UV-Vis (λ_max)	[M-H]^- (m/z)	Error (ppm)	Molecular formula	Fragment ions (m/z)	Peak area%	Reference
Cd1	Caffeoyl-hexuronic acid	2.05	245, 318	355.0883	-3.38	C₁₂H₁₉O₁₂	311, 194, 195, 179, 175, 113,	3.1	Catarino et al. (2015)Catarino, M.D., Silva, A.M., Saraiva, S.C., Sobral, A.J., Cardoso, S.M., 2015. Characterization of phenolic constituents and evaluation of antioxidant properties of leaves and stems of Eriocephalus africanus. Arab. J. Chem., http://dx.doi.org/10.1016/j.arabjc.2015.04.018. http://dx.doi.org/10.1016/j.arabjc.2015....
Cd2	Caffeoyl-hexuronide derv.	2.86	240, 320	339.0935	-4.13	C₁₂H₂₀O₁₁	355, 311, 179, 175, 113	0.9	Catarino et al. (2015)Catarino, M.D., Silva, A.M., Saraiva, S.C., Sobral, A.J., Cardoso, S.M., 2015. Characterization of phenolic constituents and evaluation of antioxidant properties of leaves and stems of Eriocephalus africanus. Arab. J. Chem., http://dx.doi.org/10.1016/j.arabjc.2015.04.018. http://dx.doi.org/10.1016/j.arabjc.2015....
Cd3	(Iso) pentyl dihexose	10.17	258	411.1506	-2.43	C₁₆H₂₈O₁₂	249, 205	0.15	Barros et al. (2012)Barros, L., Dueñas, M., Carvalho, A., Ferreira, I., Santos-Buelga, C., 2012. Characterization of phenolic compounds in flowers of wild medicinal plants from Northeastern Portugal. Food Chem. Toxicol. 50, 1576-1582.
Cd4	Caffeoyl ferulic acid derivative	17.70	240, 330	408.0429	-3.19	C₂₈H₉O₄	315, 303, 179	0.2	El Sayed et al. (2016)El Sayed, A., Ezzat, S., El Naggar, M., El Hawary, S., 2016. In vivo diabetic wound healing effect and HPLC–DAD–ESI–MS/MS profiling of the methanol extracts of eight Aloe species. Rev. Bras. Farmacogn. 26, 352-362.
Cd5	Caffeoyl ferulic acid derivative	19.05	240, 330	408.0430	-3.19	C₂₈H₉O₄	315, 303, 269, 252, 179	0.35	El Sayed et al. (2016)El Sayed, A., Ezzat, S., El Naggar, M., El Hawary, S., 2016. In vivo diabetic wound healing effect and HPLC–DAD–ESI–MS/MS profiling of the methanol extracts of eight Aloe species. Rev. Bras. Farmacogn. 26, 352-362.
Cd6	(Epi) catechin derivative	23.05	264, 320	388.0742	-3.09	C₂₆H₁₃O₄	261, 221, 219, 179	0.4	Tentative
Cd7	5-Caffeoylquinic acid	33.99	326	353.0879	-3.40	C₁₆H₁₈O₉	191, 179, 161	0.28	Clifford et al. (2003)Clifford, M.N., Johnston, K.L., Knight, S., Kuhnert, N., 2003. Hierarchical scheme for LC–MSn identification of chlorogenic acids. J. Agric. Food Chem. 51, 2900-2911.
Cd8	(Iso) rhamnetin hexoside derv.	40.61	250, 352	655.1476	2.5	C₂₂H₂₁O₁₅	315, 301, 179	0.27	Tentative
Cd9	(Iso) rhamnetin	42.44	250, 352	315.2178	-3.81	C₁₆H₁₂O₇	217, 300	0.23	Abu-Reidah et al. (2015)Abu-Reidah, I.M., Ali-Shtayeh, M.S., Jamous, R., Arráez-Román, D., Segura-Carretero, A., 2015. HPLC–DAD–ESI-MS/MS screening of bioactive components from Rhus coriaria L. (Sumac) fruits. Food Chem. 166, 179-191.
Cd10	Rutin	45.05	282, 355	609.1464	-1.64	C₂₇H₃₀O₁₆	463, 447, 301, 299	1.5	Handoussa et al. (2013)Handoussa, H., Hanafi, R., Eddiasty, I., El-Gendy, M., El Khatib, A., Linscheid, M., Mahran, L., Ayoub, N., 2013. Anti-inflammatory and cytotoxic activities of dietary phenolics isolated from Corchorus olitorius and Vitis vinifera. J. Funct. Food 5, 1204-1216.
Cd11	Yunnaneic acid F	47.3	297, 330	597.1828	-0.87	C₂₉H₂₆O₁₄	579, 359, 295, 179	0.72	Barros et al. (2012)Barros, L., Dueñas, M., Carvalho, A., Ferreira, I., Santos-Buelga, C., 2012. Characterization of phenolic compounds in flowers of wild medicinal plants from Northeastern Portugal. Food Chem. Toxicol. 50, 1576-1582.
Cd12	Kaempferol 3-O-glucoside 7-O-rhamnoside	49.63	254, 366	593.1514	-2.36	C₂₇H₃₀O₁₅	431, 269	0.58	Farag et al. (2016)Farag, M.A., Handoussa, H., Fekry, M.I., Wessjohann, L., 2016. Metabolites profiling in 18 Saudi date palm fruit cultivars and their antioxidant potential via UPLC–qTOF-MS and multivariate data analyses. Food Funct. 7, 1077-1086.
Cd13	(Iso) rhamnetin rhamnosyl hexoside	50.48	250, 352	623.1619	-1.60	C₂₈H₃₁O₁₆	477, 315, 300	0.38	Farag et al. (2016)Farag, M.A., Handoussa, H., Fekry, M.I., Wessjohann, L., 2016. Metabolites profiling in 18 Saudi date palm fruit cultivars and their antioxidant potential via UPLC–qTOF-MS and multivariate data analyses. Food Funct. 7, 1077-1086.
Cd14	Quercetin dimethyl ether rutinose	55.61	282, 357	637.1775	-1.57	C₂₉H₃₄O₁₆	491, 329, 179, 151	0.6	Simirgiotis (2013)Simirgiotis, M.J., 2013. Antioxidant capacity and HPLC-DAD–MS profiling of Chilean Peumo (Cryptocarya alba) fruits and comparison with German Peumo (Crataegus monogyna) from Southern Chile. Molecules 18, 2061-2080.
Cd15	Gallocatechin	60.08	274	305.0667	-3.28	C₁₅H₁₄O₇	261, 221, 219, 179, 167, and 165	0.72	Dou et al. (2007)Dou, I., Lee, V.S., Tzen, J., Lee, M., 2007. Identification and comparison of phenolic compounds in the preparation of Oolong tea manufactured by semifermentation and drying processes. J. Agric. Food Chem. 55, 7462-7468.
Cd16	Acetyl di-caffeoylquinic acid	65.76	245, 317	557.2607	-0.77	C₂₇H₂₅O₁₃	515, 353, 179	0.53	Lin and Harnly (2010)Lin, L., Harnly, J.M., 2010. Identification of the phenolic components of Chrysanthemum flower (Chrysanthemum morifolium Ramat). Food Chem. 120, 319-326.
Cd17	Flavonoid derivative	67.79	255, 354	523.2918	-3.25	C₂₈H₄₃O₉	179, 1047	1.35	Zou et al. (2011)Zou, Y., Chang, S.K., Gu, Y., Qian, S., 2011. Antioxidant activity and phenolic compositions of lentil (Lens culinaris var. morton) extract and its fractions. J. Agric. Food Chem. 59, 2268-2276.
Cd18	Di-flavonoid derivative	68.77	255, 355	1047.5877	-2.77	C₄₈H₅₆O₂₆	523, 179	2.7	Żuchowski et al. (2014)Żuchowski, J., Pecio, L., Stochmal, A., 2014. Novel flavonol glycosides from the aerial parts of lentil (Lens culinaris). Molecules 19, 18152-18178.
Cd19	(Iso) rhamnetin-glu-malonate	68.85	270, 360	563.3024	-2.55	C₂₅H₂₄O₁₅	315, 301, 179	2.9	Abu-Reidah et al. (2015)Abu-Reidah, I.M., Ali-Shtayeh, M.S., Jamous, R., Arráez-Román, D., Segura-Carretero, A., 2015. HPLC–DAD–ESI-MS/MS screening of bioactive components from Rhus coriaria L. (Sumac) fruits. Food Chem. 166, 179-191.
Cd20	Digalloyl deoxyhexose	72.65	274	465.2870	3.01	C₂₀H₁₈O₁₃	313, 301, 179, 169	1.98	Abdel-Hameed et al. (2013)Abdel-Hameed, E.S., Bazaid, S.A., Salman, M.S., 2013. Characterization of the phytochemical constituents of Taif rose and its antioxidant and anticancer activities. BioMed. Res. Int., http://dx.doi.org/10.1155/2013/345465. http://dx.doi.org/10.1155/2013/345465...

Peak (compound)	Identified compounds	Retention time (min)	UV-Vis (λ_max)	[M-H]^- (m/z)	Error (ppm)	Formula	Fragment ions (m/z)	peak area%	Reference
Aa1	Caftaric acid	2.02	240, 320	311.0620	-3.86	C₁₀H₁₅O₁₁	179, 149	0.32	Handoussa et al. (2013)Handoussa, H., Hanafi, R., Eddiasty, I., El-Gendy, M., El Khatib, A., Linscheid, M., Mahran, L., Ayoub, N., 2013. Anti-inflammatory and cytotoxic activities of dietary phenolics isolated from Corchorus olitorius and Vitis vinifera. J. Funct. Food 5, 1204-1216.
Aa2	Caffeoylquinic acid derivative	2.22	244, 326	461.2029	1.8	C₁₆H₁₈O₉	281, 239, 191, 179, 137	0.75	El Sayed et al. (2016)El Sayed, A., Ezzat, S., El Naggar, M., El Hawary, S., 2016. In vivo diabetic wound healing effect and HPLC–DAD–ESI–MS/MS profiling of the methanol extracts of eight Aloe species. Rev. Bras. Farmacogn. 26, 352-362.
Aa3	3-Caffeoylquinic acid	4.32	244, 326	353.0878	-3.12	C₁₆H₁₈O₉	191, 179	0.12	Clifford et al. (2005)Clifford, M., Knight, S., Kuhnert, N., 2005. Discriminating between the six isomers of dicaffeoylquinic acid by LC–MSn. J. Agric. Food Chem. 53, 3821-3832.
Aa4	5-Caffeoylquinic acid	21.10	244, 326	353.0881	-3.97	C₁₆H₁₈O₉	191, 179	0.47	Clifford et al. (2005)Clifford, M., Knight, S., Kuhnert, N., 2005. Discriminating between the six isomers of dicaffeoylquinic acid by LC–MSn. J. Agric. Food Chem. 53, 3821-3832.
Aa5	Apigenin-7-β-O-glucuronide	22.36	267, 355	445.2082	-3.14	C₂₁H₁₈O₁₁	431, 335, 269	0.52	Pereira et al. (2013)Pereira, O.R., Peres, A.M., Silva, A.M., Domingues, M.R., Cardoso, S.M., 2013. Simultaneous characterization and quantification of phenolic compounds in Thymus citriodorus using a validated HPLC–UV and ESI-MS combined method. Food Res. Int. 54, 1773-1780.
Aa6	4-Caffeoylquinic acid	23.42	244, 326	353.0901	1.25	C₁₆H₁₈O₉	173, 179	0.2	Clifford et al. (2005)Clifford, M., Knight, S., Kuhnert, N., 2005. Discriminating between the six isomers of dicaffeoylquinic acid by LC–MSn. J. Agric. Food Chem. 53, 3821-3832.
Aa7	Digallic acid	27.18	nd	321.0242	-0.31	C₁₄H₁₀O₉	169, 125	0.17	Abu-Reidah et al. (2015)Abu-Reidah, I.M., Ali-Shtayeh, M.S., Jamous, R., Arráez-Román, D., Segura-Carretero, A., 2015. HPLC–DAD–ESI-MS/MS screening of bioactive components from Rhus coriaria L. (Sumac) fruits. Food Chem. 166, 179-191.
Aa8	5-Feruloylquinic acid	29.36	240, 360	367.1036	-3.54	C₁₇H₂₀O₉	190, 172	0.18	Lin and Harnly (2010)Lin, L., Harnly, J.M., 2010. Identification of the phenolic components of Chrysanthemum flower (Chrysanthemum morifolium Ramat). Food Chem. 120, 319-326.
Aa9	3-Feruloylquinic acid	30.83	240, 360	367.1037	-3.81	C₁₇H₂₀O₉	192, 179	0.3	Lin and Harnly (2010)Lin, L., Harnly, J.M., 2010. Identification of the phenolic components of Chrysanthemum flower (Chrysanthemum morifolium Ramat). Food Chem. 120, 319-326.
Aa10	Caffeoyl coumaryl glucaric acid	34.48	241, 265	535.1672	2.5	C₂₆H₃₁O₁₂	355, 209, 179, 163	0.45	Lin and Harnly (2010)Lin, L., Harnly, J.M., 2010. Identification of the phenolic components of Chrysanthemum flower (Chrysanthemum morifolium Ramat). Food Chem. 120, 319-326.
Aa11	Feruloylquinic acid	35.21	240, 360	367.1037	-3.81	C₁₇H₂₀O₉	192, 179	0.4	Lin and Harnly (2010)Lin, L., Harnly, J.M., 2010. Identification of the phenolic components of Chrysanthemum flower (Chrysanthemum morifolium Ramat). Food Chem. 120, 319-326.
Aa12	Caffeic acid derivative	43.03	220, 316	381.1194	2.46	C₂₆H₅O₄	353, 337, 179	2.45	Gouveia and Castilho (2011)Gouveia, S., Castilho, P.C., 2011. Characterisation of phenolic acid derivatives and flavonoids from different morphological parts of Helichrysum obconicum by a RP-HPLC–DAD–ESI-MSn method. Food Chem. 129, 333-344.
Aa13	Vitexin (apigenin 8-C-hexoside)	43.48	336	431.0987	-3.48	C₂₁H₂₀O₁₀	311, 270, 179	2.5	Barros et al. (2012)Barros, L., Dueñas, M., Carvalho, A., Ferreira, I., Santos-Buelga, C., 2012. Characterization of phenolic compounds in flowers of wild medicinal plants from Northeastern Portugal. Food Chem. Toxicol. 50, 1576-1582.
Aa14	Apigenin-7-hexoside	46.41	336	431.0988	-3.48	C₂₁H₂₀O₁₀	270, 179	0.28	Barros et al. (2012)Barros, L., Dueñas, M., Carvalho, A., Ferreira, I., Santos-Buelga, C., 2012. Characterization of phenolic compounds in flowers of wild medicinal plants from Northeastern Portugal. Food Chem. Toxicol. 50, 1576-1582.
Aa15	4,5-Dicaffeoylquinic acid dimer	48.11	220, 330	1031.2443	0.78	C₅₀H₄₇O₂₄	515, 191, 179	2.75	Clifford et al. (2005)Clifford, M., Knight, S., Kuhnert, N., 2005. Discriminating between the six isomers of dicaffeoylquinic acid by LC–MSn. J. Agric. Food Chem. 53, 3821-3832.
Aa16	4,5-Dicaffeoylquinic acid	49.64	220, 330	515.1200	-3.11	C₂₅H₂₄O₁₂	191, 179	2.34	Clifford et al. (2005)Clifford, M., Knight, S., Kuhnert, N., 2005. Discriminating between the six isomers of dicaffeoylquinic acid by LC–MSn. J. Agric. Food Chem. 53, 3821-3832.
Aa17	Caffeoyl-feruloylquinic acid isomer	51.54	243, 366	529.1353	-2.46	C₂₆H₂₆O₁₂	367, 353, 191, 179	1.2	Lin and Harnly (2010)Lin, L., Harnly, J.M., 2010. Identification of the phenolic components of Chrysanthemum flower (Chrysanthemum morifolium Ramat). Food Chem. 120, 319-326.
Aa18	3,5-Dicaffeoylquinic acid dimer	53.59	220, 330	1031.2438	1.26	C₅₀H₄₇O₂₄	515, 191, 179	3.2	Clifford et al. (2005)Clifford, M., Knight, S., Kuhnert, N., 2005. Discriminating between the six isomers of dicaffeoylquinic acid by LC–MSn. J. Agric. Food Chem. 53, 3821-3832.
Aa19	Caffeoyl-feruloylquinic acid isomer	54.46	243, 366	529.1355	-2.83	C₂₆H₂₆O₁₂	367, 353, 191, 179	2.97	Lin and Harnly (2010)Lin, L., Harnly, J.M., 2010. Identification of the phenolic components of Chrysanthemum flower (Chrysanthemum morifolium Ramat). Food Chem. 120, 319-326.
Aa20	Caffeoyl-feruloylquinic acid isomer	55.57	244, 365	529.1357	-3.21	C₂₆H₂₆O₁₂	367, 353, 191, 179	1.25	Lin and Harnly (2010)Lin, L., Harnly, J.M., 2010. Identification of the phenolic components of Chrysanthemum flower (Chrysanthemum morifolium Ramat). Food Chem. 120, 319-326.
Aa21	3,4-Di-feruloylquinic acid	56.58	254, 367	543.1510	-0.37	C₂₇H₂₈O₁₂	349, 299, 193	0.72	Clifford et al. (2005)Clifford, M., Knight, S., Kuhnert, N., 2005. Discriminating between the six isomers of dicaffeoylquinic acid by LC–MSn. J. Agric. Food Chem. 53, 3821-3832.
Aa22	3,5-Di-feruloylquinic acid	57.01	254, 367	543.1512	-2.21	C₂₇H₂₈O₁₂	367, 349	0.79	Clifford et al. (2005)Clifford, M., Knight, S., Kuhnert, N., 2005. Discriminating between the six isomers of dicaffeoylquinic acid by LC–MSn. J. Agric. Food Chem. 53, 3821-3832.
Aa23	Caffeoyl-feruloylquinic acid isomer	59.82	243, 366	529.1355	-2.83	C₂₆H₂₆O₁₂	367, 353, 191, 179	3.5	Lin and Harnly (2010)Lin, L., Harnly, J.M., 2010. Identification of the phenolic components of Chrysanthemum flower (Chrysanthemum morifolium Ramat). Food Chem. 120, 319-326.
Aa24	(Iso) rhamnetin-O-hexoside sulphate	64.35	225, 340	557.1669	3.41	C₂₂H₂₁O₁₅S	316, 301, 179	1.3	Kargbo et al. (2015)Kargbo, M., Gbago, O., Song, Y., 2015. In vitro anti-diabetic activity and phenolic compound profile of ethanol extracts of Anisophyllea laurina R. Br. ex Sabine leaves and stem bark. Euro Acad. Res. 2, 16089-16106.
Aa25	Di-feruloylquinic acid	64.65	254, 367	543.1512	-2.76	C₂₇H₂₈O₁₂	367, 349	2.1	Clifford et al. (2005)Clifford, M., Knight, S., Kuhnert, N., 2005. Discriminating between the six isomers of dicaffeoylquinic acid by LC–MSn. J. Agric. Food Chem. 53, 3821-3832.
Aa26	3,4,5-Tricaffeoylquinic acid	65.38	220, 330	677.1516	-1.48	C₃₄H₃₀O₁₅	515, 179	1.6	Gouveia and Castilho (2011)Gouveia, S., Castilho, P.C., 2011. Characterisation of phenolic acid derivatives and flavonoids from different morphological parts of Helichrysum obconicum by a RP-HPLC–DAD–ESI-MSn method. Food Chem. 129, 333-344.
Aa27	(Iso) rhamnetin-O-hexoside sulphate	66.67	225, 340	557.1669	3.41	C₂₂H₂₁O₁₅S	316, 301, 179	1.25	Abu-Reidah et al. (2015)Abu-Reidah, I.M., Ali-Shtayeh, M.S., Jamous, R., Arráez-Román, D., Segura-Carretero, A., 2015. HPLC–DAD–ESI-MS/MS screening of bioactive components from Rhus coriaria L. (Sumac) fruits. Food Chem. 166, 179-191.
Aa28	Feruloyl dicaffeoylquinic acid	67.06	250, 368	691.1668	2.89	C₃₄H₂₇O₁₆	515, 335, 179	3.15	Johnson et al. (2014)Johnson, C.E., Lin, L.Z., Harnly, J.M., Oladeinde, F.O., Kinyua, A.M., Michelin, R., Bronner, Y., 2014. Identification of the phenolic components of Vernonia amygdalina and Russelia equisetiformi. J. Nat. Prod. 4, 57-64.
Aa29	Di-feruloyl caffeoylquinic acid	68.79	250, 368	719.1990	-1.39	C₃₆H₃₁O₁₆	515, 335, 191, 179	0.7	Johnson et al. (2014)Johnson, C.E., Lin, L.Z., Harnly, J.M., Oladeinde, F.O., Kinyua, A.M., Michelin, R., Bronner, Y., 2014. Identification of the phenolic components of Vernonia amygdalina and Russelia equisetiformi. J. Nat. Prod. 4, 57-64.
Aa30	Dicaffeoyl ferulic acid derivative	69.65	243, 366	671.4020	-1.46	C₂₈H₂₂O₁₀	529, 179	1.3	Tentative

[1] * Corresponding author. E-mail:aabdulmtaal@kku.edu.sa (A. Abdel Motaal).

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Characterization of hepatoprotective metabolites from Artemisia annua and Cleome droserifolia using HPLC/PDA/ESI/MS–MS

ABSTRACT