Preliminary prospection of phytotherapic compounds from the essential oils from barks and leaves of Umburana (<i>Commiphora Leptophloeos</i>)

Pinto, Keyla Bessa; Santos, Pedro Henrique Batista dos; Krause, Laiza Canielas; Caramão, Elina Bastos; Bjerk, Thiago Rodrigues

doi:10.1590/s2175-97902022e21609

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Brazilian Journal of Pharmaceutical Sciences

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Article • Braz. J. Pharm. Sci. 58 • 2022 • https://doi.org/10.1590/s2175-97902022e21609 copy

Preliminary prospection of phytotherapic compounds from the essential oils from barks and leaves of Umburana (Commiphora Leptophloeos)

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

The potential of the biome caatinga (exclusive from northeastern Brazil) has been evaluated in recent research for application in the pharmaceutical industry. Among the species of medicinal plants from caatinga, one can highlight the Commiphora leptophloeos (umburana), which has been used as infusions and syrups by the regional population for inflammatory and infectious diseases. Essential oils from umburana leaves and barks were obtained in a Clevenger apparatus and analyzed by gas chromatography/mass spectrometry, and total phenolic and flavonoids were determined by spectrophotometric analysis. It was observed that a large part of the major compounds present in the essential oil is described as having antitumor activity, enabling research in investigational oncology with umburana (C. leptophloeos). In addition, some little explored components have been identified, such as cadinene, alpha-selinene, and elemenone. Despite being easily found in several plants, there are no clinical trials involving their biological activity in a well-defined isolated form, which could make exploring new studies possible. Furthermore, the presence of phenolic compounds and flavonoids allows future studies about the potential antimicrobial and antioxidant activity.

Keywords:
Commiphora leptophloeos; Medicinal plant; Gas chromatography; Essential oil

Compound name	Chemical Classes	R.T.	Area %		LTPRI			Reference (NIST WEB BOOK)
Compound name	Chemical Classes	R.T.	Barks	Leaves	Exp	Lit.	Diff
1-Hexanol, 3,5,5-trimethyl	Alcohol	20.57	0.04	0.00	1039	1049	-10	Begnaud, Pérès, et al., 2003
Geraniol (2,6-Octadien-1-ol, 3,7-dimethyl)	Alcohol	28.85	0.07	0.00	1252	1260	-8	Cao, Li, et al., 2011
Isophytol	Alcohol	49.53	0.00	0.07	1947	1947	0	Todua, 2011
Phytol	Alcohol	53.47	0.00	1.84	2114	2114	0	Skaltsa, Mavrommati, et al., 2001
alcohols			0.11	1.91
Benzoic acid, octyl ester	Esters	44.54	0.13	0.00	1754	1757	-3	Korhonen, 1986,
abd-7,13(E)-dien-15-yl acetate	Esters	59.32	1.16	0.00	2387	2393	-6	Anastasaki, Demetzos, et al., 1999
Kolavenol acetate	Esters	59.88	0.72	0.00	2415	2412	3	Andriamaharavo, 2014
Octacosyl acetate	Esters	76.09	0.00	1.08	3215	3215	0	Zheng and White, 2008
esteres			2.02	1.08
Octanoic acid	Fatty acid	25.87	0.81	0.00	1172	1170	2	Andriamaharavo, 2014
Geranic acid	Fatty acid	32.27	0.02	0.30	1350	1355	-5	Andriamaharavo, 2014
Decanoic acid	Fatty acid	32.72	0.36	0.00	1363	1373	-10	Engel and Ratel, 2007
Tetradecanoic acid	Fatty acid	44.69	1.24	0.19	1760	1759	1	Lalel, Singh, et al., 2003
Pentadecanoic acid	Fatty acid	47.28	0.50	0.00	1858	1867	-9	Tret'yakov, 2008
9-Hexadecenoic acid	Fatty acid	49.35	0.25	0.00	1949	1957	-8	Tret'yakov, 2007
Hexadecanoic acid	Fatty acid	49.97	8.54	4.46	1966	1963	3	Yu, Liao, et al., 2007
Linolenic acid, methyl ester	Fatty acid	53.35	0.06	0.00	2109	2108	1	Rout, Rao, et al., 2007
9,12-Octadecadienoic acid	Fatty acid	53.92	1.27	0.00	2134	2133	1	Radulovic, Dordevic, et al., 2010
Linoleic acid	Fatty acid	54.17	0.00	0.72	2145	2144	1	Saroglou, Dorizas, et al., 2006
Octadecanoic acid	Fatty acid	54.62	0.00	0.59	2165	2166	-1	bin Jantan, Yalvema, et al., 2005
Palmitic acid β-monoglyceride	Fatty acid	61.93	0.00	0.54	2520	2519	1	Andriamaharavo, 2014
fatty acids			13.05	6.80
1-Hexacosanol	Fatty Alcohol	68.97	0.00	0.26	2907	2906	1	Andriamaharavo, 2014
Octacosanol	Fatty Alcohol	73.38	0.00	2.80	3113	3110	3	Andriamaharavo, 2014
fatty alcohols			0.00	3.05
Pentadecanal	Fatty Aldehyde	43.49	0.80	0.00	1715	1717	-2	Flamini, Tebano, et al., 2006
Heptadecanal	Fatty Aldehyde	48.92	0.00	0.18	1922	1922	0	Tkachev, Dobrotvorsky, et al., 2000
Tetradec-(7Z)-enal	Fatty Aldehyde	54.05	2.27	0.00	2140	2141	-1	Radulovic, Blagojevic, et al., 2009
fatty aldehydes			3.07	0.18
Hexadecanoic acid, methyl ester	Fatty Esters	49.14	0.19	0.00	1931	1926	5	Quijano, Salamanca, et al., 2007
Hexadecanoic acid, ethyl ester	Fatty Esters	50.63	0.00	0.06	1992	1992	0	Rout, Rao, et al., 2007
fatty esters			0.19	0.06
Decane, 4- methyl-	branched-alkane	21.17	0.05	0.00	1052	1054	-2	Oruna-Concha, Ames, et al., 2002
Decane, 5- methyl-	branched-alkane	21.27	0.15	0.00	1054	1057	-3	Rembold, Wallner, et al., 1989
Decane, 3- methyl-	branched-alkane	21.64	0.19	0.00	1068	1069	-1	Zaikin and Borisov, 2002
Decane, 2- methyl-	branched-alkane	22.13	0.13	0.00	1075	1076	-1	Saroglou, Marin, et al., 2007
Undecane, 5- methyl-	branched-alkane	25.46	0.08	0.00	1161	1159	2	Kallio, Jussila, et al., 2006
Undecane, 2- methyl-	branched-alkane	25.65	0.08	0.00	1166	1164	2	Kallio, Jussila, et al., 2006
branched alkanes			0.69	0.00
Undecane	n-alkane	23.06	0.11	0.00	1099	1100	-1	Standard
Dodecane	n-alkane	26.89	0.04	0.00	1200	1200	0	Standard
Tetracosane	n-alkane	59.58	0.00	0.10	2400	2400	0	Standard
Heptacosane	n-alkane	65.29	0.00	2.71	2700	2700	0	Standard
Octacosane	n-alkane	67.02	0.00	0.25	2799	2800	-1	Standard
Nonacosane	n-alkane	68.85	0.00	4.93	2901	2900	1	Standard
Triacontane	n-alkane	70.80	0.00	0.91	2999	3000	-1	Standard
Hentriacontane	n-alkane	73.14	0.00	10.55	3104	3100	4	Standard
Dotriacontane	n-alkane	75.69	0.00	1.31	3202	3200	2	Standard
Tritriacontane	n-alkane	78.85	0.00	6.38	3304	3300	4	Standard
Hexatriacontane	n-alkane	92.67	0.00	0.91	3607	3600	7	Standard
n-alkanes			0.14	28.04
6-Methyl-2-heptene-5-one	Ketone	18.47	0.06	0.00	985	982	3	Bastos, Ishimoto, et al., 2006
5,9-Undecadien-2-one, 6,10-dimethyl-, (Z)-	Ketone	35.55	0.05	0.00	1449	1456	-7	Xian Q., Chen H., et al., 2006
Phytone	Ketone	46.90	0.10	0.11	1843	1842	1	Bendiabdellah, El Amine Dib, et al., 2012
Farnesyl acetone	Ketone	48.72	0.10	0.75	1915	1913	2	Mondello, 2012
ketones			0.30	0.86
Hinokinin	Lignan	73.63	0.00	1.28	3103	3096	7	Andriamaharavo, 2014
Loliolide	ketone	45.57	0.00	0.22	1792	1784	8	Andriamaharavo, 2014
Eugenol	Phenols	32.66	0.00	0.03	1361	1365	-4	Mondello, Sciarrone, et al., 2007
others			0.00	1.54
Myrcene	Monoterpene	18.65	0.05	0.00	989	989	0	Dharmawan, Kasapis, et al., 2007
Ocimene (1,3,6-Octatriene, 3,7-dimethyl)	Monoterpene	20.98	0.05	0.00	1047	1048	-1	Dob, Dahmane, et al., 2006,
Linalool	Monoterpene	23.13	0.29	0.00	1100	1100	0	Cho, Namgung, et al., 2008
Linalool oxide <trans->	Monoterpene	26.21	0.00	0.03	1180	1176	4	Adams, 2017
Terpineol, cis-ß-	Monoterpene	27.03	0.11	0.00	1202	1207	-5	Cho, Namgung, et al., 2008
Myrtenyl acetate	Monoterpene	31.45	0.11	0.00	1326	1326	0	Houël., 2015
8-Hydroxylinalool	Monoterpene	32.84	0.00	0.04	1367	1367	0	Andriamaharavo, 2014
Isogermacrene D	Monoterpene	35.11	0.00	0.09	1435	1439	-4	Radulovic, Lazarevic, et al., 2007
monoterpenes			0.59	0.17
4,8,12,16-Tetramethylheptadecan-4-olide	Diterpenes	58.75	0.00	0.13	2359	2364	-5	Andriamaharavo, 2014
Methyl kolavenate	Diterpenes	59.16	0.50	0.00	2379	2372	7	Andriamaharavo, 2014
diterpenes			0.50	0.13
Supraene	Triterpene	67.40	0.00	0.80	2820	2822	-2	Steiner, Steidle, et al., 2005
Lup-20(29)-en-3-one	Triterpene	82.01	0.00	0.36	3390	3384	6	Andriamaharavo, 2014
Cycloartenol	Triterpene	84.59	0.00	2.32	3454	3466	-12	Andriamaharavo, 2014
Lupeol	Triterpene	85.04	0.00	9.24	3459	3450	9	Leite, 2018
Friedelan-3-one	Triterpene	87.36	0.00	1.47	3510	3511	-1	Andriamaharavo, 2014
triterpenes			0.00	14.19
Bicycloelemene	Sesquiterpene	32.06	0.23	0.00	1344	1338	6	Houël., 2015
α -Cubebene	Sesquiterpene	32.49	0.18	0.00	1357	1356	1	Cardeal, da Silva, et al., 2006
α -Copaene	Sesquiterpene	33.61	2.02	0.06	1389	1393	-4	Carasek and Pawliszyn, 2006
β -Elemene	Sesquiterpene	33.97	2.60	0.34	1400	1396	4	Gauvin-Bialecki and Marodon, 2009
β - Caryophyllene	Sesquiterpene	34.74	5.10	0.58	1424	1423	1	Houël., 2015
γ-Elemene	Sesquiterpene	34.97	0.53	0.00	1431	1432	-1	Houël., 2015
β -Ylangene	Sesquiterpene	35.03	0.21	0.04	1433	1431	2	Mosayebi, Amin, et al., 2008
Caryophyllene	Sesquiterpene	35.18	0.83	0.62	1438	1440	-3	Cardeal, da Silva, et al., 2006
trans- α -Bergamotene	Sesquiterpene	35.31	10.77	1.18	1442	1441	1	Benkaci-Ali, Baaliouamer, et al., 2007
β -Copaene	Sesquiterpene	35.46	0.34	0.11	1447	1437	10	Andriamaharavo, 2014
α -Guaiene	Sesquiterpene	35.50	0.04	0.00	1448	1446	2	Cardeal, da Silva, et al., 2006
β -Farmesene	Sesquiterpene	35.70	0.34	0.00	1454	1459	-5	Flamini, Cioni, et al., 2007
Aromandendrene	Sesquiterpene	35.77	1.50	0.00	1456	1447	9	Elias, Simoneit, et al., 1997
epi-β-Caryophylleno	Sesquiterpene	35.83	0.00	0.03	1458	1463	-5	Yu, Liao, et al., 2007
Valerena-4,7(11)-diene	Sesquiterpene	35.97	0.40	0.04	1462	1465	-3	Andriamaharavo, 2014
Cadina-3,5-diene	Sesquiterpene	36.05	0.06	0.00	1465	1457	8	Dickschat, Martens, et al., 2005
Alloaromadendrene	Sesquiterpene	36.22	0.37	0.00	1470	1464	6	Houël., 2015
Humulene < α ->	Sesquiterpene	36.34	0.48	0.25	1474	1467	7	Dharmawan, Kasapis, et al., 2007
Selina-4,11-diene	Sesquiterpene	36.51	3.11	0.45	1479	1476	3	Houël., 2015
ε-Cadinene -	Sesquiterpene	36.60	0.27	0.00	1482	1482	0	Houël., 2015
Germacrene D	Sesquiterpene	36.70	0.32	0.00	1485	1484	1	Houël., 2015
δ-Selinene -	Sesquiterpene	36.82	2.86	0.12	1489	1489	0	Houël., 2015
β-Selinene	Sesquiterpene	36.93	0.32	0.00	1492	1493	-1	Houël., 2015
Curzerene	Sesquiterpene	37.14	0.56	0.17	1499	1497	2	Houël., 2015
α-Selinene	Sesquiterpene	37.43	4.36	1.91	1508	1499	9	Houël., 2015
α -Muurolene	Sesquiterpene	37.54	1.19	0.11	1512	1517	-5	Jalali-Heravi, Zekavat, et al., 2006
Germacrene A -	Sesquiterpene	37.59	0.45	0.00	1513	1510	3	Houël., 2015
β -Bisabolene	Sesquiterpene	37.64	2.06	0.79	1515	1514	1	Andriamaharavo, 2014
γ-Cadinene	Sesquiterpene	37.78	0.32	0.03	1520	1515	5	Houël., 2015
δ-Cadinene	Sesquiterpene	38.06	0.67	0.09	1529	1519	10	Houël., 2015
Cadinene <delta->	Sesquiterpene	38.15	3.62	0.19	1532	1534	-2	Houël., 2015
Calamenene <trans->	Sesquiterpene	38.27	1.19	0.00	1536	1524	12	Houël., 2015
ο-Cadinene -	Sesquiterpene	38.38	1.06	0.30	1540	1538	2	Houël., 2015
Elemol	Sesquiterpene	38.73	0.62	0.27	1551	1549	2	Houël., 2015
Germacrene B	Sesquiterpene	38.86	2.60	0.00	1555	1557	-2	Oliveira, Leitao, et al., 2006
α -Calacorene	Sesquiterpene	38.91	0.26	0.00	1557	1547	10	Andriamaharavo, 2014
Selina-3,7(11)-diene	Sesquiterpene	39.02	2.39	0.00	1561	1562	-1	Facey, Porter, et al., 2005
Palustrol	Sesquiterpene	39.94	0.81	0.00	1591	1581	10	Courtois, Paine, et al., 2009
Spathulenol	Sesquiterpene	40.06	3.27	0.12	1595	1594	1	Sabulal, Dan, et al., 2007
Ledol (Globulol)	Sesquiterpene	40.19	0.17	2.12	1600	1608	-9	Shivashankar, Roy, et al., 2012
Caryophyllene oxide	Sesquiterpene	40.36	0.24	0.31	1605	1612	-7	Eyres, Marriott, et al., 2007
Epiglobulol	Sesquiterpene	40.44	1.37	0.88	1608	1608	0	Skaltsa, Mavrommati, et al., 2001
Elemenone<trans-beta->	Sesquiterpene	40.64	5.22	6.28	1615	1607	8	Andriamaharavo, 2014
Viridiflorol	Sesquiterpene	40.71	1.62	0.09	1618	1609	9	Andriamaharavo, 2014
Isospathulenol	Sesquiterpene	41.03	1.88	0.26	1612	1608	4	Dehghan, Solaimanian, et al., 2007
Humulene epoxide II	Sesquiterpene	41.18	0.31	0.12	1634	1635	-1	Cardeal, da Silva, et al., 2006
Germacrone	Sesquiterpene	41.38	0.15	0.00	1649	1658	-9	Marongiu, Piras, et al., 2005
Di-epi-1,10-cubenol	Sesquiterpene	41.54	1.16	0.46	1647	1640	7	Bertoli, Lepnardi, et al., 2011
β -Acorenol	Sesquiterpene	41.74	0.11	0.00	1643	1639	6	Rout, Naik, et al., 2006
Pogostol	Sesquiterpene	41.77	0.32	0.00	1654	1651	3	Adams, 2017
Bulnesol	Sesquiterpene	41.96	0.04	0.00	1661	1670	-9	Adams, 2017
tau-Muurolol	Sesquiterpene	41.99	2.31	0.08	1652	1641	11	Radulovic, Blagojevic, et al., 2010
α -Muurolol	Sesquiterpene	42.01	0.24	0.00	1663	1654	9	Radulovic, Blagojevic, et al., 2010
Intermedeol	Sesquiterpene	42.08	0.00	0.10	1665	1667	-2	Andriamaharavo, 2014
Aristol-1(10)-en-9-ol	Sesquiterpene	42.29	0.24	0.00	1672	1680	-8	Andriamaharavo, 2014
α -Cadinol	Sesquiterpene	42.34	1.15	0.17	1674	1668	6	Kim, Lee, et al., 2003
7-epi-α-Eudesmol	Sesquiterpene	42.43	0.45	0.36	1668	1659	9	Simoniatto, Bonani, et al., 2007
tau-Cadinol	Sesquiterpene	42.53	0.26	0.27	1681	1679	2	Phutdhawong, Kawaree, et al., 2007
Bisabolol <alpha->	Sesquiterpene	42.60	0.40	0.00	1683	1682	1	Benkaci-Ali, Baaliouamer, et al., 2007
α -Bisabolol	Sesquiterpene	42.89	1.12	0.15	1694	1697	-4	Sabulal, Dan, et al., 2007
Longifolol	Sesquiterpene	43.28	0.00	0.20	1707	1713	-6	Adams, 2017
(1R,7S)-Germacra-4(15),5,10(14)-trien-1β-ol	Sesquiterpene	43.36	0.00	0.09	1701	1695	6	Andriamaharavo, 2014
Nootkatol	Sesquiterpene	43.52	0.17	0.00	1717	1715	2	Adams, Habte, et al., 2004
Germacrone	Sesquiterpene	43.62	0.00	0.20	1716	1708	8	Andriamaharavo, 2014
Juniper camphor	Sesquiterpene	43.65	1.35	0.00	1719	1709	10	Andriamaharavo, 2014
Bisabolone	Sesquiterpene	44.58	0.33	0.00	1755	1755	0	Tuberoso, Kowalczyk, et al., 2005
Isovalencenol	Sesquiterpene	45.43	0.40	0.13	1787	1793	-6	Adams, 2017
Neophytadiene	Sesquiterpene	46.71	0.05	0.55	1836	1841	-6	Andriamaharavo, 2014
Curcumenone	Sesquiterpene	47.11	0.00	0.17	1851	1844	7	Andriamaharavo, 2014
sesquiterpenes			79.35	20.80
Ergost-5-en-3-ol, (3β.)-	Sterols	77.93	0.00	1.19	3275	-		n.i.
gamma-Sitosterol	Sterols	81.04	0.00	7.25	3359	3351	8	Andriamaharavo, 2014
5α-Stigmasta-7,16-dien-3β-ol	Sterols	82.94	0.00	10.62	3412	3401	11	Radulovic and Dordevic, 2011
sterols			0.00	19.06
gamma-Tocopherol	Tocopherols	72.42	0.00	0.89	3072	3074	-2	Andriamaharavo, 2014
DL - α -Tocopherol	Tocopherols	74.40	0.00	1.23	3152	3150	3	Andriamaharavo, 2014
tocopherols			0.00	2.12

Universidade de São Paulo, Faculdade de Ciências Farmacêuticas Av. Prof. Lineu Prestes, n. 580, 05508-000 S. Paulo/SP Brasil, Tel.: (55 11) 3091-3824 - São Paulo - SP - Brazil
E-mail: bjps@usp.br

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[1] *Correspondence: T. R. Bjerk^.Programa de Pós-Graduação em Biotecnologia Industrial. Universidade Tiradentes, Aracaju, SE, Brasil. Av. Murilo Dantas 300, CEP: 49032-490. Aracaju, Sergipe, Brasil. E-mail: thiagobjerk@gmail.com. ORCID: https://orcid.org/0000-0003-0067-6804