. 2024 Apr 23;9(18):19940–19955. doi: 10.1021/acsomega.3c09674

Table 3. Phenolic Compounds Tentatively Identified in the Wolffia Residue and Filtrate Samples Using LC-ESI-QTOF-MS/MS^b.

s. no.	proposed compounds	molecular formula	RT (min)	mode of ionization (ESI^–/ESI⁺)	molecular weight	observed (m/z)	mass error (ppm)	samples
Phenolic Acids
Hydroxycinnamic Acids
1	chlorogenic acid	C₁₈H₂₈O₃	7.042	[M – H]⁻	354.0961	353.0885	–2.95	CWR, CWF
2	caffeic acid	C₉H₈O₄	6.252	[M – H]⁻	180.0414	179.0341	4.91	CWR, CWF
3	isoferulic acid	C₁₀H₁₀O₄	5.768	[M – H]⁻	194.0569	193.0495	4.96	CWF
4	m-coumaric acid	C₉H₈O₃	3.418	[M – H]⁻	164.0463	163.039	6.36	CWR
5	sagecoumarin	C₂₇H₂₀O₁₂	5.595	[M – H]⁻	536.0998	581.098	–8.09	BWF
6	6-O-p-coumaroyl-d-glucose	C₁₅H₁₈O₈	4.343	[M – H]⁻	326.105	325.0973	–14.75	BWF
7	monotrans-p coumaroylmesotartaric acid	C₁₃H₁₂O₈	4.715	[M – H]⁻	296.053	295.0457	0.73	TWR, TWF
8	hordatineA	C₂₈H₃₈N₈O₄	13.707	[M – H]⁻	550.2966	549.2913	9.02	BWR
9	esculetin	C₉H₆O₄	4.313	[M – H]⁻	178.0251	177.0178	8.34	TWF
10	6-demethoxycapillarisin	C₁₅H₁₀O₆	8.046	[M – H]⁻	286.0477	285.0403	0.27	TWR
Hydroxybenzoic Acids
11	benzoic acid	C₇H₆O₂	5.504	[M – H]⁻	122.0362	121.0288	4.73	TWF, CWF
12	ellagic acid	C₁₄H₆O₈	5.623	[M – H]⁻	302.0046	300.9973	5.67	TWR, TWF, CWR, CWF
13	gallicacid3-O-(6-galloylglucoside)	C₂₀H₂₀O₁₄	5.247	^a[M – H]⁻	484.0757	483.0703	19.89	TWF
14	2,6-dihydroxybenzoic acid	C₇H₆O₄	4.131	[M – H]⁻	154.0259	153.0187	4.3	CWR, CWF
15	resorcinol	C₆H₆O₂	4.092	[M – H]⁻	110.0366	109.0293	1.9	CWR, CWF
16	4-(3,5-diphenylcyclohexyl)phenol	C₂₄H₂₄O	7.817	[M + H]⁺	328.1833	351.1722	–1.69	TWR
17	[7]-paradol	C₁₈H₂₈O₃	13.261	[M – H]⁻	292.2032	291.196	2.07	TWF
18	2,4,6-trihydroxybenzoic acid	C₇H₆O₅	1.566	[M – H]⁻	170.0198	169.0127	9.88	CWR, TWR
Flavonoids
Flavonols
19	kaempferol 3-rhamnoside 7-xyloside	C₂₆H₂₈O₁₄	5.529	^a[M – H]⁻	564.1533	563.1466	–10.27	BWR, BWF, TWR, TWF, CWR, CWF
20	kaempferol 3-O-β-d-galactoside	C₂₁H₂₀O₁₁	5.16	[M – H]⁻	448.0992	447.092	3.12	TWR, CWR
21	kaempferol 3-xylosylglucoside	C₂₆H₂₈O₁₅	4.732	[M – H]⁻	580.1405	579.1333	4.02	TWR, CWR
22	kaempferol 7-O-glucoside	C₂₁H₂₀O₁₁	5.913	[M – H]⁻	448.1008	447.0934	–0.54	CWR, CWF, TWF
23	kaempferol	C₁₅H₁₀O₆	7.673	[M – H]⁻	286.0479	285.0405	–0.43	CWF, TWF
24	quercitrin	C₂₁H₂₀O₁₁	5.23	[M – H]⁻	448.106	447.0988	–12.03	BWR, BWF, CWR, CWF
25	quercetin	C₁₅H₁₀O₇	7.654	[M – H]⁻	302.0412	301.0341	4.88	TWR
26	quercetin 3,7-dirhamnoside	C₂₇H₃₀O₁₅	4.851	[M – H]⁻	594.1585	593.1513	–0.13	TWF, TWR, CWF
27	rustoside	C₂₆H₂₈O₁₅	4.816	[M – H]⁻	580.1492	579.1413	–10.01	BWR, BWF, TWR, CWF
28	rutin	C₂₇H₃₀O₁₆	4.256	[M – H]⁻	610.1534	609.1457	0.8	TWF,TWR, CWF, CWR
29	allivicin	C₂₇H₃₀O₁₆	4.812	[M – H]⁻	610.1591	609.1519	–9.43	BWR, BWF
Flavones
30	astragalin 7-rhamnoside	C₂₇H₃₀O₁₅	4.639	[M – H]⁻	594.1558	593.1486	4.56	CWR, TWR, TWF
31	(3″-apiosyl-6″-malonyl)astragalin	C₂₉H₃₀O₁₈	6.141	[M – H]⁻	666.1307	725.144	18.72	BWF
32	apigenin 7-glucoside	C₂₁H₂₀O₁₀	5.628	^a[M – H]⁻	432.104	431.0968	3.79	TWR, TWF, CWF
33	luteolin 4′-O-glucoside	C₂₁H₂₀O₁₁	5.549	[M – H]⁻	448.1007	447.0941	–1.46	TWF, CWF
34	ephedranninA	C₃₀H₂₀O₁₁	4.802	[M – H]⁻	556.0936	615.1092	12.46	BWF, TWR
35	cynaroside	C₂₁H₂₀O₁₁	5.589	[M – H]⁻	448.1054	447.0982	–10.78	BWR
36	6-C-galactosylluteolin	C₂₁H₂₀O₁₁	5.179	^a[M – H]⁻	448.0946	447.0921	2.78	TWR, TWF, CWR
37	nicotiflorin	C₂₇H₃₀O₁₅	4.683	[M – H]⁻	594.1642	593.157	–9.67	BWR, BWF
38	maritimetin	C₁₅H₁₀O₆	7.79	[M + H]⁺	286.0438	287.0508	13.89	TWF
Flavanones
39	3,3′,5-trihydroxy-4′,7-dimethoxyflavanone	C₁₇H₁₆O₇	1.229	[M + H]⁺	332.0899	377.0899	–0.92	BWR
Flavanols
40	ent-fisetinidol-(4β→8)-catechin-(6→4β)-ent-fisetinidol	C₄₅H₃₈O₁₇	5.242	[M – H]⁻	850.1954	895.1938	18.2	TWF, BWF
Isoflavonols
41	genistein 4′,7-O-diglucuronide	C₂₇H₂₆O₁₇	5.136	[M – H]⁻	622.1104	621.1048	10.67	BWR
42	genistein 8-C-glucoside	C₂₁H₂₀O₁₀	5.658	[M – H]⁻	432.1113	431.099	–1.2	BWR, BWF, TWF, CWF
43	2-hydroxychrysophanol	C₁₅H₁₀O₅	8.549	[M – H]⁻	270.0525	269.0453	1.01	TWF
Biflavonoids
44	ent-epiafzelechin(2a→7,4a→8)epiafzelechin 3-(4-hydroxybenzoic acid)	C₃₇H₂₈O₁₂	6.561	[M – H]⁻	664.1511	709.148	12.21	BWF
45	sciadopitysin	C₃₃H₂₄O₁₀	4.813	[M + H]⁺	580.1358	581.1432	2.02	TWR, TWF
Flavans
46	kuwanonZ	C₃₄H₂₆O₁₀	4.898	[M + H]⁺	594.1511	595.1584	2.56	TWR, TWF
47	flavidulolC	C₃₄H₄₂O₄	13.489	[M + H]⁺	514.3074	537.2969	1.83	TWR, TWF
Other Polyphenols
Pigments
48	pheophorbide a	C₃₅H₃₆N₄O₅	17.592	^a[M + H]⁺	592.2613	615.2511	11.4	TWR, TWF, CWR
49	3-cis-hydroxy-b,e-caroten-3′-one	C₄₀H₅₄O	19.537	[M + H]⁺	550.4103	551.4176	12.94	TWR, TWF
50	4Z,15E-bilirubin IXa	C₃₃H₃₆N₄O₆	16.527	[M + H]⁺	584.2595	607.2477	6.83	TWR
Alkaloids
51	calycanthine	C₂₂H₂₆N₄	16.436	[M – H]⁻	346.217	327.0041	–7.34	BWR
52	ritterazine A	C₅₄H₇₆N₂O₁₀	20.154	[M – H]⁻	912.5433	971.5591	7.3	BWR
53	(−)-sparteine	C₁₅H₂₆N₂	8.427	[M + H]⁺	234.2058	235.2131	16.04	TWF
54	vinpocetine	C₂₂H₂₆N₂O₂	9.489	[M + H]⁺	350.202	351.2093	–7.39	TWF
55	cancentrine	C₃₆H₃₄N₂O₇	16.093	[M + H]⁺	606.2405	607.2476	–6.39	TWF, TWR
56	terminaline	C₂₃H₄₁NO₂	12.477	[M + H]⁺	363.3085	364.3158	14.39	TWF
57	embelin	C₁₇H₂₆O₄	10.944	[M – H]⁻	294.1826	293.175	1.8	TWR, CWR
58	thalidasine	C₂₂H₂₆N₂O₂	12.6	[M – H]⁻	652.3191	711.3352	–6.46	TWR
59	3β,6β-dihydroxynortropane	C₇H₁₃NO₂	1.09	[M + H]⁺	143.0918	144.0993	19.63	TWR, CWR
60	retronecine	C₈H₁₃NO₂	1.168	[M + H]⁺	155.0921	156.0994	16.22	TWR
61	ipecac (psychotrine)	C₂₈H₃₆N₂O₄	12.477	[M + H]⁺	462.2513	463.2617	4.6	TWR
62	cepharanthine	C₃₇H₃₈N₂O₆	19.039	[M + H]⁺	606.2768	607.2841	–6.26	TWR
63	benzosimuline	C₂₀H₁₉NO₂	2.174	[M + H]⁺	305.1452	328.1343	–11.86	TWF
Terpenoids
64	ganosporelactoneA	C₃₀H₄₀O₇	18.552	[M + H]⁺	512.2746	611.1532	5.29	TWR, TWF
65	7-O-acetylaustroinulin	C₂₂H₃₆O₄	18.642	[M + H]⁺	364.2561	387.2453	14.57	TWR, TWF
66	triterpenoid	C₃₀H₄₈O₇₅	18.245	^a[M – H]⁻	552.3066	551.3062	–0.95	BWR, CWF
67	geranylfarnesyl diphosphate	C₂₅H₄₄O₇P₂	17.514	^a[M + H]⁺	518.2563	577.2705	–0.17	CWF
68	tocopheronic acid	C₁₆H₂₂O₅	11.167	[M + H]⁺	294.143	317.1319	12.59	TWR
69	tsangane l 3-glucoside	C₁₉H₃₄O₇	12.945	[M – H]⁻	374.2279	433.2418	6.92	BWR
70	ganoderic acid F	C₃₂H₄₂O₉	17.896	[M + H]⁺	570.2791	593.2688	5.7	TWR, TWF
71	3,3′-bisanigorufone	C₃₈H₂₂O₄	5.137	[M + H]⁺	542.1587	565.1479	–12.65	TWF
Tannin
72	2,6-digalloylglucose	C₂₀H₂₀O₁₄	5.287	[M – H]⁻	484.0815	483.0765	7.15	BWF

Compounds were detected in the negative [M – H]⁻ and positive [M + H]⁺ modes of ionization, while only single mode of data was presented.

RT: retention time.

Table 3. Phenolic Compounds Tentatively Identified in the Wolffia Residue and Filtrate Samples Using LC-ESI-QTOF-MS/MSb.

Table 3. Phenolic Compounds Tentatively Identified in the Wolffia Residue and Filtrate Samples Using LC-ESI-QTOF-MS/MS^b.