Unveiling the Bacterial Sesquiterpenome of <i>Streptomyces</i> sp. CBMAI 2042 Discloses Cyclases with Versatile Performances

Sachito, Douglas C.; Oliveira, Luciana G. de

doi:10.21577/0103-5053.20220013

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Article • J. Braz. Chem. Soc. 33 (07) • 2022 • https://doi.org/10.21577/0103-5053.20220013 copy

Unveiling the Bacterial Sesquiterpenome of Streptomyces sp. CBMAI 2042 Discloses Cyclases with Versatile Performances

Authorship SCIMAGO INSTITUTIONS RANKINGS

Terpenes are the most abundant class of natural product that exist in nature. They possess a myriad of industrial applications including pharmaceutical, perfumery and flavors, bulk chemicals, and fuel. Intriguingly, until today, the vast majority of characterized terpenoids have been isolated from plants and fungi, and only in recent years bacteria were found to generate a representative reservoir of terpenoids molecules. Mining Streptomyces sp. CBMAI 2042 genome data has revealed the presence of five terpene cyclase genes. Chemical analysis of mycelium extract of this bacteria strain has unveiled at least 28 volatile terpenes molecules, where three encoding sesquiterpene cyclase (STC) genes are apparently responsible for their biosynthesis. The cyclic products obtained by incubation of these three purified recombinant STCs with farnesyl diphosphate (FPP) were analyzed by gas chromatography-mass spectrometry (GC-MS) and identified using the Van den Dool and Kratz equation.

Keywords:
bacterial terpenome; genome mining; terpene cyclase; sesquiterpenes

No.^a a Compounds numbers were assigned in ascending order of retention time;	Compound³¹31 Adams, R. P.; Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry; 4th ed.; Allured Publishing: Carol Stream, 2007.	A medium		ISP2 medium		TSBY medium		AI lit.^d d arithmetic index in literature;
		t_R^b b retention time; / min	AI exp^c c experimental arithmetic index;	t_R / min	AI exp.	t_R / min	AI exp.	AI lit.^d d arithmetic index in literature;
1	(+)-trans-limonene-1,2-epoxide^e e internal standard;	11.66	1135	11.67	1135	11.73	1136	1137
2	8,10-dimethyl-1-octalin³²32 Nawrath, T.; Dickschat, J. S.; Müller, R.; Jiang, J.; Cane, D. E.; Schulz, S.; J. Am. Chem. Soc. 2008, 130, 430.	15.17	1222	15.18	1222	-	-	-
3	8,10-dimethyl-1(9)-octalin³²32 Nawrath, T.; Dickschat, J. S.; Müller, R.; Jiang, J.; Cane, D. E.; Schulz, S.; J. Am. Chem. Soc. 2008, 130, 430.	15.53	1230	15.54	1231	-	-	-
4	unidentified	16.26	1248	-	-	-	-	-
5	α-copaene	21.46	1373	21.46	1373	21.52	1374	1373
6	β-elemene^f f generated from germacrene A by Cope rearrangement in the injection port of the GC apparatus.	22.16	1389	22.15	1389	-	-	1389
7	geosmin	22.46	1397	22.46	1397	-	-	1399
8	α-gurjunene	22.85	1406	22.84	1406	-	-	1409
9	unidentified	22.99	1410	22.99	1410	-	-	-
10	β-caryophyllene	23.22	1415	23.22	1415	23.26	1416	1417
11	unidentified	23.36	1419	23.35	1419	23.41	1420	-
12	β-gurjunene	23.77	1429	23.72	1428	23.77	1429	1431
13	humulene	24.60	1450	-	-	-	-	1452
14	unidentified	24.72	1453	24.72	1453	-	-	-
15	alloaromadendrene	24.89	1457	-	-	-	-	1458
16	unidentified	25.05	1461	-	-	-	-	-
17	germacrene D	25.72	1477	25.71	1477	-	-	1480
18	unidentified	25.90	1482	-	-	-	-	-
19	unidentified	26.01	1485	26.02	1485	-	-	-
20	α-muurolene	26.51	1497	26.51	1497	26.56	1498	1500
21	germacrene A	26.65	1501	26.65	1501	-	-	1508
22	unidentified	27.08	1512	-	-	-	-	-
23	δ-cadinene	27.41	1520	27.4	1520	27.46	1522	1522
24	trans-cadina-1,4-diene	27.74	1529	27.73	1529	27.79	1530	1533
25	caryophyllenyl alcohol	29.13	1565	29.13	1565	29.19	1567	1570
26	germacrene D-4-ol	29.38	1572	-	-	-	-	1574
27	4-epi-cubedol	29.85	1584	29.84	1583	29.90	1585	1576
28	1-epi-cubenol	31.38	1625	31.36	1624	31.42	1626	1627
29	1(10)E,5E-germacradien-11-ol	31.77	1635	31.74	1634	-	-	1633

Compound³²32 Nawrath, T.; Dickschat, J. S.; Müller, R.; Jiang, J.; Cane, D. E.; Schulz, S.; J. Am. Chem. Soc. 2008, 130, 430.	AI exp^a a Experimental arithmetic index;			AI lit.^c c arithmetic index in literature;
	enzTS-1^b b terpene cyclase recombinant enzyme;	enzTS-2^b b terpene cyclase recombinant enzyme;	enzTS-3^b b terpene cyclase recombinant enzyme;	AI lit.^c c arithmetic index in literature;
8,10-Dimethyl-1-octalin³¹31 Adams, R. P.; Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry; 4th ed.; Allured Publishing: Carol Stream, 2007. (2)	1221	-	-	-
8,10-Dimethyl-1(9)-octalin³¹31 Adams, R. P.; Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry; 4th ed.; Allured Publishing: Carol Stream, 2007. (3)	1230	-	-	-
α-Copaene (5)	-	1371	-	1372
β-Elemene^d d generated from germacrene A by Cope rearrangement in the injection port of the GC apparatus. (6)	-	1388	-	1389
Geosmin (7)	1395	-	-	1399
β-Caryophyllene (10)	-	-	1433	1417
β-Gurjunene (12)	-	1425	-	1431
Germacrene D (17)	1475	1475	-	1480
Unidentified (18)	1481	-	-	-
Unidentified (19)	-	1490	-	-
α-Muurolene (20)	-	1495	-	1500
δ-Cadinene (23)	-	1519	-	1522
trans-Cadina-1,4-diene (24)	-	1527	-	1533
Germacrene D-4-ol (26)	-	1569	-	1574
1-Epi-cubenol (28)	-	1621	-	1627
1(10)E,5E-Germacradien-11-ol (29)	1632	-	-	1633
δ-Elemene^d d generated from germacrene A by Cope rearrangement in the injection port of the GC apparatus. (30)	-	1333	-	1335
Unidentified (31)	-	1580	-	-

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