Chemical composition profile of the essential oil from hymenocrater bituminous and its health functionality

Figures & data

Table 1. Chemical composition of aerial parts of Hymenocrater bituminous essential oil.

No.	Compound ^a	Percentage^b	RI^c	RI lit^d	Identification Method ^e
1	α-Thujene	0.7	920	924	RI,MS
2	α-Pinene	18.2	926	932	RI, MS, Co-I
3	Camphene	0.1	939	946	RI, MS, Co-I
4	Thuja-2,4(10)-diene	0.1	945	953	RI,MS
5	Benzaldehyde	0.1	953	952	RI, MS, Co-I
6	Sabinene	0.7	965	969	RI, MS, Co-I
7	β-Pinene	11.3	967	974	RI, MS, Co-I
8	Myrcene	0.1	989	988	RI, MS, Co-I
9	p-Cymene	0.4	1021	1020	RI, MS, Co-I
10	Limonene	0.7	1025	1024	RI, MS, Co-I
11	1,8-Cineole	4.1	1026	1026	RI, MS, Co-I
12	Linalool	0.4	1100	1095	RI, MS, Co-I
13	α-Campholenal	1.6	1122	1122	RI,MS
14	trans-Pinocarveol	1.0	1132	1135	RI, MS, Co-I
15	cis-Verbenol	0.2	1137	1137	RI,MS
16	trans-Verbenol	2.5	1140	1140	RI,MS
17	Pinocarvone	0.5	1157	1160	RI,MS
18	Terpinen-4-ol	0.2	1173	1174	RI, MS, Co-I
19	p-Cymen-8-ol	0.1	1183	1179	RI,MS
20	α-Terpineol	0.2	1187	1186	RI, MS, Co-I
21	(3Z)-Hexenyl butanoate	0.4	1188	1184	RI,MS
22	Myrtenal	0.8	1191	1195	RI, MS, Co-I
23	Myrtenol	0.8	1193	1194	RI, MS, Co-I
24	(3Z)-Hexenyl 3-methyl butanoate	0.6	1238	1232	RI,MS
25	n-Tridecane	0.4	1300	1300	RI, MS, Co-I
26	α-Copaene	0.2	1368	1374	RI,MS
27	β-Bourbonene	2.4	1375	1387	RI,MS
28	4aα,7α,7aβ-Nepetalactone	1.1	1380	1386	RI,MS
29	α-Humulene	0.3	1443	1452	RI, MS, Co-I
30	Germacrene D	1.8	1471	1484	RI,MS
31	(E)-β-Ionone	0.8	1481	1487	RI, MS, Co-I
32	n-Pentadecane	0.5	1500	1500	RI, MS, Co-I
33	trans-Calamenene	1.9	1514	1521	RI,MS
34	Myristicin	1.8	1517	1517	RI, MS, Co-I
35	α-Calacorene	0.2	1534	1544	RI,MS
36	Spathulenol	8.5	1567	1576	RI,MS
37	Caryophyllene oxide	0.3	1571	1582	RI, MS, Co-I
38	Salvial-4(14)-en-1-one	0.3	1582	1594	RI,MS
39	Humulene epoxide II	0.9	1597	1608	RI,MS
40	epi-α-Cadinol	0.9	1632	1638	RI,MS
41	α-Cadinol	0.4	1646	1652	RI,MS
42	Eudesma-4(15),7-dien-1β-ol	1.0	1675	1687	RI,MS
43	Hexahydrofarnesyl acetone	0.7	1844	1845	RI,MS
44	n-Hexadecanoic acid	1.7	1966	1959	RI, MS, Co-I
45	Abietatriene	1.0	2036	2055	RI,MS
46	Abietadiene	1.2	2057	2087	RI,MS
47	trans-Phytol	11.0	2105	2104	RI, MS, Co-I
48	n-Tricosane	0.3	2306	2300	RI, MS, Co-I
49	n-Pentacosane	2.4	2500	2500	RI, MS, Co-I
50	n-Heptacosane	3.3	2700	2700	RI, MS, Co-I
51	n-Nonacosane	3.0	2900	2900	RI, MS, Co-I
Monoterpene hydrocarbons		32.3
Oxygenated monoterpenes		13.5
Sesquiterpene hydrocarbons		6.8
Oxygenated sesquiterpenes		13.0
Diterpenes		13.2
Alkanes		9.9
Others		5.4
Total		94.1

^aCompounds are listed in order of their elution from a HP-5MS column. ^bRelative percentage values are means of three determinations with a RSD% in all cases below 10%. ^cLinear retention index on HP-5MS column, experimentally determined using homologous series of C₈–C₃₀ alkanes. ^dLinear retention index taken from Adams (2007) and/or NIST 08 (2008). ^eIdentification methods: Co-I, based on comparison with authentic compounds; MS, based on comparison with WILEY, ADAMS, FFNSC2 and NIST 08 MS databases; RI, based on comparison of calculated RI with those reported in ADAMS, FFNSC 2 and NIST 08.

Figure 1. Chemical structures of the major components of Hymenocrater bituminous essential oil.

Table 2. Radical scavenging activity of Hymenocrater bituminous.

	Radical scavenging activity
Samples	DPPH radical (mmol TEs/g extract)^a	ABTS radical cation (mmol TEs/g extract)^a
EO	Na	na
DCM	0.14 ± 0.01^*a	0.57 ± 0.02^a
MeOH	1.78 ± 0.01^b	4.29 ± 0.13^b

^aTEs: trolox equivalents. na: not active. *Values expressed are means ± S.D. of three parallel measurements. Data marked with different letters indicate significant difference (p < 0.05).

Table 3. Reducing power and metal chelating activity of Hymenocrater bituminous.

Samples	Reducing power activity		Metal chelating activity
	CUPRAC (mmol TEs/g oil or extract)^a	FRAP (mmol TEs/g oil or extract)^a	Chelating effect (mg EDTAEs/g oil or extract)^b
EO	0.25 ± 0.01^*a	0.19 ± 0.01^a	40.52 ± 1.30^a
DCM	0.46 ± 0.04^b	0.31 ± 0.01^b	20.26 ± 0.90^b
MeOH	2.78 ± 0.05^c	1.93 ± 0.03^c	2.19 ± 0.29^c

^aTEs: trolox equivalents. ^bEDTAEs: EDTA equivalents. *Values expressed are means ± S.D. of three parallel measurements. Data marked with different letters indicate significant difference (p < 0.05).

Table 4. Total bioactive components and total antioxidant activity of Hymenocrater bituminous.

	Total bioactive compounds		Total antioxidant activity
Samples	Total phenolic (mg GAEs/g extract)^a	Total flavonoid (mg REs/g extract)^b	Phosphomolybdenum (mmol TEs/g oil or extract)^c
EO	–	–	3.84 ± 0.12^a
DCM	29.90 ± 0.66^*a	14.31 ± 0.01^a	1.82 ± 0.05^b
MeOH	120.88 ± 0.82^b	22.01 ± 0.14^b	2.67 ± 0.18^c

^aGAEs: gallic acid equivalents. ^bREs: rutin equivalents. ^cTEs: trolox equivalents. * Values expressed are means ± S.D. of three parallel measurements. Data marked with different letters indicate significant difference (p < 0.05).

Table 5. Therapeutic target enzyme inhibitory activity of Hymenocrater bituminous.

	Anti-Alzheimer’s disease effects		Anti-diabetic effects		Skin-care effects	Anti-obesity effects
Samples	AChE Inhibition (mg GEs/g oil or extract)^a	BChE Inhibition (mg GEs/g oil or extract)^a	α-amylase inhibition (mmol ACEs/g oil or extract)^b	α-glucosidase inhibition (mmol ACEs/g oil or extract)^b	Tyrosinase inhibition (mg KAEs/g oil or extract)^c	Lipase Inhibition (mmol OEs/g oil or extract)^d
EO	3.83 ± 0.01^*a	4.71 ± 0.01^a	0.91 ± 0.09^a	40.17 ± 1.40^a	45.41 ± 4.27^a	1.51 ± 0.01^a
DCM	2.08 ± 0.01^b	1.78 ± 0.01^b	0.57 ± 0.01^b	4.32 ± 0.15^b	26.01 ± 2.57^b	0.57 ± 0.01^b
MeOH	1.49 ± 0.04^c	0.71 ± 0.06^c	0.28 ± 0.04^c	11.45 ± 0.18^c	4.96 ± 0.45^c	0.08 ± 0.01^c

^aGEs: galantamine equivalents. ^bACEs: Acarbose equivalents. ^cKAEs: kojic acid equivalents. ^dOEs: orlistat equivalents. *Values expressed are means ± S.D. of three parallel measurements. Data marked with different letters indicate significant difference (p < 0.05).