Chemical profile of the volatile fraction of <i>Bauhinia forficata</i> leaves: an evaluation of commercial and <i>in natura</i> samples

JUNG, Eliane Przytyk; ALVES, Raphael Cruz; ROCHA, Werickson Fortunato de Carvalho; MONTEIRO, Sérgio da Silva; RIBEIRO, Leilson de Oliveira; MOREIRA, Ricardo Felipe Alves

doi:10.1590/fst.34122

Acessibilidade / Reportar erro

Brasil

Food Science and Technology

Español English

Brasil

Español English

sumário « anterior atual seguinte »

Sumário

Original Article • Food Sci. Technol 42 • 2022 • https://doi.org/10.1590/fst.34122 copy

Chemical profile of the volatile fraction of Bauhinia forficata leaves: an evaluation of commercial and in natura samples

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Bauhinia forficata Link is widely used in Brazilian folk medicine to treat several pathologies. Commercial and botanically identified samples were evaluated via a gas chromatography equipped with a flame ionization detector and a gas chromatography-mass spectrometer. This procedure allowed the identification of 116 compounds, representing 72% to 96% of the total content of the investigated essential oils. The five samples analyzed showed yields of essential oil ranged from 0.03 to 0.10%, being sesquiterpenes and oxygenated sesquiterpenes the major components. Hierarchical Cluster Analysis and Principal Component Analysis were used in order to demonstrate variations in the essential oils’ composition of B. forficata and were able to clusterize these samples in three groups based on relationships and chemical patterns in essential oils. In natura samples showed to be different from commercial samples and CS3 group was the most distinct group of the commercial samples. In spite of differences among samples, it is concluded that essential oils of B. forficata presented a rich composition, presenting 11 compounds in common between them, which could be possible to establish a set of compounds as chemical markers for the species, still non-existent in literature.

Keywords:
B. forficata; pata-de-vaca; essential oils; GC-MS; sesquiterpenes

COMPOUND	LRI_exp	LRI_lit	IN Area_(Avg)%	CS1 Area_(Avg)%	CS2 Area_(Avg)%	CS3 Area_(Avg)%	CS4 Area_(Avg)%
α-pinene^(M)	930	930^*	-	-	-	0.25	0.18
o-cymene^(M)	1023	1022*	-	-	-	0.14	0.09
limonene^(M)	1028	1028*	-	0.13	-	-	0.05
eucaliptol^(OM)	1032	1032*	0.06	0.03	0.04	-	-
γ-terpinene^(M)	1059	1059*	-	-	-	-	0.02
cis linalool oxide^(OM)	1072	1072^#	-	-	0.05	-	-
trans linalool oxide^(OM)	1088	1088*	-	-	0.03	-	-
linalool^(OM)	1101	1103*	-	0.13	0.15	-	-
α-tujone^(M)	1107	1106*	0.09	-	0.08	-	0.04
trans-pinocarveol^(OM)	1137	1138 *	-	0.18	0.13	-	0.01
verbenol^(OM)	1143	1143^§	-	0.14	-	0.10	0.07
camphor^(OM)	1145	1145§	0.04	-	0.02	-	0.25
α-phellandren-8-ol^(OM)	1151	1159§	-	-	-	-	0.03
pinocarvone^(OM)	1164	1164§	-	0.10	-	0.07	0.09
methyl salicilate^(E)	1170	1170§		0.20	0.11	-	0.07
4-terpineol^(OM)	1176	1177*	-	-	-	0.04	0.08
α-terpineol^(OM)	1193	1194*	0.04	0.08	-	-	-
myrtenal^(OM)	1198	1198§	-	0.27	-	0.10	0.22
verbenone^(OM)	1212	1218#	-	0.11	0.09	0.10	0.25
β-cyclocitral^(OM)	1223	1223§	-	0.154	-	-	0.07
pulegone^(OM)	1242	1243*	-	0.1	-	-	-
carvone^(OM)	1247	1248*	-	0.106	-	-	-
geraniol^(OM)	1260	1260§	-	0.03	-	-	-
anethol^(OM)	1286	1285§	-	0.21	0.04	0.04	0.07
4-vinyl guaiacol^(P)	1317	1317§	-	-	0.05	-	-
δ- elemene^(S)	1337	1337#	0.84	0.35	0.15	-	0.21
α-cubebene^(S)	1348	1349*	-	0.93	1.10	0.45	0.90
eugenol^(PP)	1360	1360*	-	-	0.10	-	0.11
ylangene^(S)	1371	1372*	-	0.12	-	-	0.19
α-copaene^(S)	1376	1376*	1.07	1.16	1.46	1.49	2.90
β-bourbonene^(S)	1384	1384*	0.76	0.62	-	0.37	0.78
β-cubebene^(S)	1389	1389#	1.19	0.18	1.22	0.51	0.51
β-elemene^(S)	1391	1391#	-	2.1	0.79	0.44	3.92
cyperene^(S)	1398	1398§	0.13	-	-	0.42	0.77
NI	1406		-	-	-	0.60	-
methyl eugenol^(PP)	1412	1412§	-	-	-	-	0.95
β-caryophyllene^(S)	1419	1419§	7.11	3.0	4.36	3.01	3.89
α-ionone^(N)	1430	1430*	-	0.27	-	-	0.73
γ-elemene^(S)	1435	1434*	0.77	-	-	0.34	-
α-guaiene^(S)	1439	1439*	0.30	0.14	-	-	-
aromadendrene^(S)	1447	1440#	-	0.67	-	0.71	2.09
α-humulene^(S)	1452	1452*	5.26	1.28	1.12	0.85	1.41
geranyl acetone^(N)	1456	1456§	-	-	0.15	-	0.24
alloaromadendrene^(S)	1458	1458*	1.41	-	0.61	1.02	0.78
aristolene^(S)	1461	1472§	-	0.33	-	-	-
γ-muurolene^(S)	1473	1475*	-	0.92	-	1.54	-
germacrene D^(S)	1483	1483*	19.68	2.59	4.52	0.71	5.75
α-curcumene^(S)	1486	1487§	-	0.12	-	-	-
β-selinene^(S)	1487	1488§	-	0.85	0.84	1.99	2.70
β-ionone^(N)	1490	1489§	-	0.17	0.54	-	0.54
α-selinene^(S)	1493	1494#	-	-	-	1.53	1.23
epi-bicyclosesquifellandrene^(S)	1493	1491§	-	0.34	-	-	-
bicyclogermacrene^(S)	1496	1498§	2.37	2.14	2.17	-	-
α-muurolene^(S)	1501	1499#	0.53	0.28	-	0.34	0.36
bicyclo[4.4.0]dec-1-ene, 2-isopropyl-5-methyl-9-methylene-^(S)	1502	1503*	-	-	0.50	-	-
β-bisabolene^(S)	1504	1505*	-	-	-	1.07	0.62
α-farnesene^(S)	1507	1507§	-	-	0.54	-	-
γ-cadinene^(S)	1513	1513#	0.56	-	0.36	0.40
α-amorphene^(S)	1516	1514§	-	0.39	-	0.86	1.25
δ-cadinene^(S)	1516	1516§	2.59	3.39	1.87	0.596	3.99
γ-selinene^(S)	1537	1544*	-	-	0.87	-	0.8
α-calacorene^(S)	1543	1543^**	-	-	-	-	3.82
eudesma-3,7(11)-diene^(S)	1545	1545*	-	0.15	1.09	-	-
cadala-1(10) 3,8 triene^(S)	1546	1548§	-	0.40	-	-	-
NI	1555	NI	-	-	0.43	0.63	-
germacrene B^(S)	1558	1558§	2.50	-	-	0.56	-
trans nerolidol^(OS)	1568	1569*	0.51		0.41	-	1.10
dodecanoic acid^(CA)	1573	1562*	-	0.10	-	-	-
spathulenol^(OS)	1582	1581.8*	2.46	13.99	2.94	5.64	14.48
caryophyllene oxide^(OS)	1585	1583*	5.42	3.07	1.52	15.25	5.68
ledol ou viridiflorol^(OS)	1598	1590#	-	1.28	0.20	-	0.42
Globulol^(OS)	1603	1604#	-	-	0.32	-	-
humulene epoxide II^(OS)	1607	1607§	1.48	1.56	0.42	3.43	1.51
aloaromadendrene oxide^(OS)	1613	1625*	-	-	0.36	-	-
NI	1618		-	1.50	-	-	-
NI	1629		-	-	0.86	-	-
τ-cadinol^(OS)	1643	1644*	-	-	0.61	-	-
τ-muurolol^(OS)	1647	1647§	-	1.54	-	-	-
selina-6-en-4-ol^(OS)	1656	1636*	-	-	0.95	-	-
NI	1658		-	-	-	-	4.97
α-cadinol^(OS)	1659	1658*	8.43	7.61	-	2.90	1.37
NI	1662		-	-	-	2.42	-
tumerone^(OS)	1671	1680*	-	-	-	-	0.84
eudesma 4(14)-1-diene^(S)	1673		-	-	0.23	-	-
NI	1675		-	-	-	3.95	-
cadalene^(S)	1676	1676§	-	-	0.41	3.45	4.55
NI	1679		-	-	-	2.82	-
NI	1680		-	-	0.10	-	-
NI	1687		-	-	0.33	-	-
α-bisabolol^(OS)	1688	1682*	-	-	-	0.69	-
cedren-8-13-ol^(OS)	1690	1690§	-	-	-	0.28	-
NI	1691		1.08	-	-	-	-
eudesma-4,11-dien-2-ol^(OS)	1693	1691*	-	1.29	-	-	-
NI	1698		-	-	-	0.35	-
NI	1707		-	-	-	-	0.22
NI	1708			-	-	1.33	-
2-tetradecen-1-ol^(A)	1714	1713*	-	-	0.20	-	-
pentadecanal^(AL)	1718	1715*	0.70	0.47	-	-	-
6-Isopropenyl-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol^(OS)	1719	1714*	-	-	0.08	0.42	0.15
NI	1722		-	-	-	0.58	-
mint sulfide^(SS)	1739	1740*	-	-	-	-	0.57
NI	1740		-	0.58	-	-	-
NI	1745		-	-	0.11	-	-
aristolone^(OS)	1751	1756#	-	-	0.06	-	-
α-cyperone^(OS)	1755	1755*	-	-	-	0.66	-
Anthracene^(HC)	1776	1770§	-	-	-	-	0.28
myristic acid (tetradecanoic acid)^(CA)	1777	1777§	-	2.15	1.48	-	0.39
6,10,14-trimethylpentadecan-2-one^(N)	1851	1849§	-	3.88	1.06	0.49	1.28
pentadecanoic acid^(CA)	1871	1878#	-	0.24	0.25	-	-
1-hexadecanol^(A)	1879	1879*	-	-	0.20	-	-
NI	1882		-	-	-	-	0.25
7,10 hexadecadienal^(AL)	1891	1816*	0.48	-	0.06	-	-
7,10,13 hexadecatrienal^(AL)	1897	1824*	0.70	-	0.12	-	-
2-heptadecanone^(K)	1905	1901*	-	-	0.06	-	-
4(H)cyclopentaphenantrene^(HC)	1912	1936§	-	0.20	-	-	-
NI	1918		-	0.08	-	-	-
farnesyl acetone^(N)	1923	1924§	0.28	-	0.79	0.17	0.53
methyl palmitate^(E)	1930	1930§	-	0.35	0.32	-	0.43
Isophytol^(OD)	1950	1950*	0.36	0.47	0.40	0.09	0.20
NI	1958		-	-	0.05	-	-
hexadecanoic (palmitic) acid ^(CA)	1972	1972*	2.05	19.90	32.13	10.96	5.15
ethyl palmitate^(E)	1998	1997§	0.21	-	-	-	0.08
NI	2024		-	0.36	-	-	-
NI	2030		-	-	0.34	-	-
NI	2033		-	-	-	-	0.10
geranyl linalool^(OD)	2033	2034*	0.22	-	-	-	-
Fluoranthene^(HC)	2055	2057§	-	0.50	-	-	-
heptadecanoic acid^(CA)	2073	2071§	-	-	0.30	-	-
9,12-octadecadienoic acid, methyl Ester^(E)	2098	2094*	-	-	0.27	-	0.19
9,12,15-octadecatrienoic acid, methyl ester^(E)	2105	2105*	-	-	0.66	-	0.23
phytol^(OD)	2123	2122*	20.09	-	10.16	3.11	10.64
9,12-octadienal^(A)	2146	2150§		-	-	2.64	-
NI	2147		0.12	-	-	-	-
9,12 octadecadienoic acid-linoleic acid^(CA)	2153	2154§	-	-	8.30	1.46	1.91
linolenic acid^(CA)	2158	2158§	-	-	7.94	-	-
ethyl linoleate^(E)	2166	2166§	0.28	-	-	-	-
ethyl linolenate^(E)	2173	2173§	0.47	-	-	-
stearic acid^(CA)	2173	2172*	-	-	0.91	0.79	0.21
NI	2188		0.15	-	-	-	-
neophytadiene^(D)	2224	2223^Φ	0.48	-	-	-	-
eicosane^(HC)	2297		-	-	0.04	-	-

NI: Not identified; LRI_exp: Linear retention index calculated for all components using a homologous series of n-alkanes analyzed in the same conditions of the sample; LRI_lit: Linear retention index from literature. Area (Avg)%: Percentage area of the compound in relation to the total area of the chromatogram (normalization technique) expressed as average value.
^*
National Institute of Standards and Technology (2019)National Institute of Standards and Technology – NIST. Office of Data and Informatics. (2019). NIST Chemistry Webbook, SRD 69. Retrieved from https://webbook.nist.gov/
https://webbook.nist.gov/... .
^#
Pherobase (2019)Pherobase. (2019). Semiochemicals-index. Retrieved from https://www.pherobase.com/database/compound/compounds-index.php
https://www.pherobase.com/database/compo... .
^§
Pubchem (2019)PubChem. U.S. National Library of Medicine. (2019). National Center for Biotechnology Information. Rockville Pike: PubChem Compound Database. Retrieved from https://pubchem.ncbi.nlm.nih.gov
https://pubchem.ncbi.nlm.nih.gov... .
^**
Jordan et al. (2002)Jordan, M. J., Margaria, C. A., Shaw, P. E., & Goodner, K. L. (2002). Aroma active components in aqueous Kiwi fruit essence and Kiwi fruit puree by GC-MS and multidimensional GC/GC-O. Journal of Agricultural and Food Chemistry, 50, 5386-5390..
ΦMedeiros et al. (2012)Medeiros, L. B. P., Rocha, M. S., Lima, S. G., Sousa Jr., G. R., Citó, A. M. G. L., Silva, D., Lopes, J. A. D., Moura, D. J., Saffi, J., Mobin, M., & Costa, J. G. M. (2012). Chemical constituents and evaluation of cytotoxic and antifungal activity of Lantana camara essential oils. Brazilian Journal Pharmacognosy, 22(6), 1259-1267. https://doi.org/10.1590/S0102-695X2012005000098.
https://doi.org/10.1590/S0102-695X201200... .
(M): Monoterpene.
(OM): Oxygenated monoterpene.
(S): Sesquiterpene.
(OS): Oxygenated sesquiterpene.
(P): Phenol.
(PP): Phenilpropanoid.
(N): Norisoprenoid.
(CA): Carboxylic acid.
(A): Alcohol.
(AL): Aldehyde.
(SS): Sulfurated sesquiterpene.
(HC): Hydrocarbon.
(E): Ester.
(K): Ketone.
(D): Diterpene.
(OD): Oxygenated diterpene.

Sociedade Brasileira de Ciência e Tecnologia de Alimentos Av. Brasil, 2880, Caixa Postal 271, 13001-970 Campinas SP - Brazil, Tel.: +55 19 3241.5793, Tel./Fax.: +55 19 3241.0527 - Campinas - SP - Brazil
E-mail: revista@sbcta.org.br

Acompanhe os números deste periódico no seu leitor de RSS

[1] *Corresponding author: leilson.oliveira@int.gov.br