UPLC/ESI/MS profiling of red algae Galaxaura rugosa extracts and its activity against malaria mosquito vector, Anopheles pharoensis, with reference to Danio rerio and Daphnia magna as bioindicators

El-Tabakh, Mohamed A. M.; Elhawary, Esraa A.; Hwihy, Hossam M.; Darweesh, Kareem F.; Shaapan, Raafat M.; Ghazala, Emad A.; Mokhtar, Mostafa M.; Waheeb, Hassan O.; Emam, Deyaa E. M.; Bakr, Nader A.; Shehata, Ahmed Z. I.

doi:10.1186/s12936-023-04795-w

Table 1 Secondary metabolites of the methanol and petroleum ether extracts of Galaxaura rugosa identified through tandem mass spectrometry (UPLC/ESI/MS)

From: UPLC/ESI/MS profiling of red algae Galaxaura rugosa extracts and its activity against malaria mosquito vector, Anopheles pharoensis, with reference to Danio rerio and Daphnia magna as bioindicators

No	Compound	Molecular formula	R_t (min.)	[M-H]⁻ (m/z)	[M + H]⁺/ [M + H + Na]⁺ (m/z)	Source (% Composition)		References
No	Compound	Molecular formula	R_t (min.)	[M-H]⁻ (m/z)	[M + H]⁺/ [M + H + Na]⁺ (m/z)	Meth	Pet. Ether	References
1	Afzelechin	C₁₅H₁₄O₅	0.69	273	275	6.39	33.56	[35]
2	3-methyl-epigallocatechin gallate	C₁₇H₃₄O₂	0.77	269	–	0.24	–	[57]
3	Fragment of urolithin A	C₁₃H₈O₄	0.90	198	–	0.35	–	[42]
4	Fragment	–	1.03	–	132	0.44	–	–
5	Fragment	–	6.74	187	–	0.11	–	–
6	Fragment of vitexin pentoside	–	11.51	293	–	0.27	8.38	[64]
7	Acetyl-O-galloyl hexose	C₁₅H₁₉O₁₁	11.66	–	373	0.61	–	[55]
8	Feruloyl-caffeoyl-quinic acid derivative	C₂₆H₂₆O₁₂	12.33	265	–	1.79	23.10	[50]
9	2′′,3′′-dihydro-3′,3′′′-biapigenin methyl ether	C₃₀H₂₀O₁₀	14.11	553	–	1.96	–	[36]
10	Tanshinone V	C₁₉H₁₈O₃	14.30	–	316	–	0.99	[59]
11	Fragment	–	14.71	–	304	8.22	–	–
12	Cinnamoyl hexose	C₁₅H₁₈O₇	15.00	309	–	–	12.15	[42]
13	Caffeoyl tartaric acid	C₁₃H₁₂O₉	15.29	311	–	11.22	-	[42]
14	Chlorogenic acid	C₁₆H₁₈O₉	15.57	351	353	–	6.60	[23]
14	Chlorogenic acid	C₁₆H₁₈O₉	15.57	351	353	–	6.60	[54]
15	Isoaloeresin D	C₂₉H₃₂O₁₁	15.60	555	557	4.52	–	[45]
16	Hc4 (dimer)	-	15.94	581	–	1.71	–	[65]
17	3-Sinapoylquinic acid	C₁₈H₂₂O₁₀	16.11	397	–	0.50	3.20	[42]
18	Kaempferol-3-O-pentoside	C₂₁H₂₀O₁₀	16.21	441	–	0.24	1.51	[37]
								[39]
								[38]
19	2,3-Didemethyl-(-)-demecolcine	C₁₉H₁₉NO₅	16.27	–	344	–	4.57	[63]
20	Menisperine	C₂₁H₂₆NO₄	16.41	–	357	0.75	–	[59]
21	Eriodictyol-7-O- hexoside	C₂₁H₂₂O₁₁	16.43	–	451	–	4.06	[40]
22	p-Coumaric acid hexoside	C₁₅H₁₈O₈	16.58	325	–	7.57	–	[23]
23	Fragment of Caffeic acid derivative	–	16.67	–	332	12.42	-	[55]
24	Kaempferol-O-pentose-O-hexouronic acid	C₂₇H₃₀O₁₇	16.82	617	–	–	1.82	[23]
25	Aloeresin B	C₂₉H₃₂O₁₁	16.84	393	–	7.24	–	[45]
26	Limocitrol-O-hexoside	C₂₄H₂₆O₁₄	17.36	537	–	6.45	–	[41]
27	p-Coumaroyl-quinic acid	C₁₆H₁₈O₈	17.95	337	–	–	3.58	[51]
28	Caffeoyl-2-hydroxyethane-1,1,2-tricarboxylic acid	–	17.98	339	360	17.72	2.25	[35]
28	Caffeoyl-2-hydroxyethane-1,1,2-tricarboxylic acid	–	17.98	339	360	17.72	2.25	[52]
29	Fragment of dimeric procyanidin B	–	18.38	407	–	1.76	–	[49]
30	Rosmarinic acid hexoside	C₂₄H₂₆O₁₃	18.94	521	–	1.75	–	[53]
31	Fragment of cis-resveratrol-3-O-β-galloyl-hexoside	C₂₇H₂₆O₁₂	19.26	425	492	1.71	–	[66]
32	Valoneic acid dilactone	C₂₁H₁₀O₁₃	19.56	469	–	0.27	–	[58]
33	Fragment of 13² –Hydroxypheophorbide-α-methyl ester	–	20.24	–	485	–	12.34	[53]
34	30 -O-Methylcatechin	C₁₆H₁₆O₆	20.37	303	305	1.56	–	[42]
35	Fragment of 13² –Hydroxypheophorbide-α-methyl ester	–	22.04	–	459	0.41	–	[55]
36	Rhmanocitrin-O-coumaroyl hexoside	C₃₁H₃₀O₁₄	22.26	–	609	2.48	–	[43]
37	Caffeic acid 3-O-hexouronide	C₁₅H₁₆O₁₀	22.34	355	–	0.49	–	[42]
38	Fragment of sterol ester	–	22.63	381	–	0.39	–	[67]
39	Fragment of Rhmanocitrin- O-coumaroyl hexoside	–	22.64	–	475	-	3.72	[43]
40	5-(30,50 -dihydroxyphenyl)- γ-valerolactone	C₁₇H₂₀O₁₀	24.90	383	413	0.23	–	[42]
41	3-Hydroxy-12-oleanene-28,29-dioic acid	C₃₀ H₄₆ O₅	26.14	486	–	0.07	–	[61]
42	Trimeric ferulic acid	C₃₀H₃₀O₁₂	26.65	685	–	0.11	–	[56]
43	Chrysoeriol-7-O-hexouronic acid	C₂₂H₂₀O₁₂	27.03	475	–	0.97	–	[45]
44	Quercetin-7-O-hexoside- 3-O-(malonyl) hexoside	C₃₀H₃₂O₂₀	27.43	711	–	0.44	–	[44]
45	Salvianolic acid B isomer	C₃₆H₃₀O₁₆	27.86	717	–	0.98	–	[53]
46	Luteolin derivative	–	28.38	–	739	–	1.28	[47]
47	Scutellarein-6-O-β-D-pentosylhexosyl 7-O-α-L pentosylhexoside	C₂₆ H₂₈ O₁₄	28.40	564	–	0.43	–	[46]
48	Glycitein 7-O-hexouronide	C₂₂H₂₀O₁₁	28.63	459	–	1.24	–	[42]
49	8,11,13-Abietatriene-3,11,12,16-tetrol-12-O-β-D-hexoside	C₂₆H₄₀O₉	28.85	597	–	1.04	–	[60]
50	Propanoic acid, 2-(3-acetoxy-4,4,14-trimethylandrost-8-en-17-yl)	C₂₇H₄₂O₄	29.35	–	431	1.38	–	[7]
51	3-Methyl-epigallocatechin gallate	C₂₃H₂₀O₁₁	29.41	471	–	2.84	–	[57]
52	Quercetin-3-O-hexouronide	C₂₁H₁₈O₁₃	29.69	477	–	0.54	–	[23]
								[39]
								[49]
53	Hexa-t-butylselenatrisiletane	C₂₄H₅₄SeSi₃	30.04	505	564	0.95	–	[6]
54	Fragment of trioleoylglycerol	–	30.37	886	888	0.78	–	[67]
55	Aglycone of bidesmosidic triterpene saponin	–	30.50	776	–	0.71	–	[62]
56	Fragment of chlorogenic acid	–	30.61	311	313	0.61	–	[23]
56	Fragment of chlorogenic acid	–	30.61	311	313	0.61	–	[54]
57	Taxifolin hexoside	C₂₁H₂₂O₁₂	31.07	465	–	–	2.85	[49]
% Identification
ESI −ve mode						88.15	99.00
ESI + ve mode						26.30	26.96

Meth. methanol extract, Pet. Ether petroleum ether extract, Rt retention time

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