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1 Supplementary Information Intraspecific Variation of the Volatile Chemical Composition of Myracrodruon urundeuva Fr. Allem. ( Aroeira-do-Sertão ): Characterization of Six Chemotypes Nayara C. de Aquino, a Renata M. Araújo b and Edilberto R. Silveira*,a a Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Fortaleza-CE, Brazil b Instituto de Química, Universidade Federal do Rio Grande do Norte, Natal-RN, Brazil Figure S1. 1 H NMR (500 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen CE-29 (chemotype: Δ 3 -carene). * edil@ufc.br
2 Figure S2. 1 H NMR (500 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen CE-3 (chemotype: Δ 3 -carene). Figure S3. 1 H NMR (500 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen RN-4 (chemotype: Δ 3 -carene).
3 Figure S4. 1 H NMR (300 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen PE-2 (chemotype: limonene). Figure S5. 1 H NMR (300 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen PE-4 (chemotype: limonene).
4 Figure S6. 1 H NMR (500 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen RN-3 (chemotype: limonene). Figure S7. 1 H NMR (300 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen BA-4 (chemotype: myrcene).
5 Figure S8. 1 H NMR (500 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen RN-2 (chemotype: myrcene). Figure S9. 1 H NMR (500 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen PE-1 (chemotype: myrcene).
6 Figure S10. 1 H NMR (500 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen CE-4 (chemotype: α-pinene). Figure S11. 1 H NMR (500 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen CE-28 (chemotype: α-pinene).
7 Figure S12. 1 H NMR (500 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen PE-3 (chemotype: α-pinene). Figure S13. 1 H NMR (300 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen CE-5 (chemotype: (Z)-β-ocimene).
8 Figure S14. 1 H NMR (300 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen CE-6 (chemotype: (E)-β-ocimene). Figure S15. 1 H NMR (300 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen BA-2 (chemotype: (Z)-β-ocimene).
9 Figure S16. 1 H NMR (300 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen CE-11 (chemotype: (E)-β-ocimene). Figure S17. 1 H NMR (300 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen CE-18 (chemotype: (E)-β-ocimene).
10 Figure S18. 1 H NMR (500 MHz, CDCl 3 ) spectrum of the crude essential oil from specimen CE-32 (chemotype: (E)-β-ocimene).
11 Figure S19. Map of the Northeast of Brazil (highlighting Ceará and Rio Grande do Norte States) detailing the collection points of leaves from wild specimens of aroeiras-do-sertão (chemotypes: myrcene (M), α-pinene (P), limonene (L), Δ 3 -carene (C), (Z)-β-ocimene ( Z O) and (E)-β-ocimene ( E O)).
12 Table S1. Experimental data of essential oils from leaves of 62 wild specimens of aroeira-do-sertão from locations at different states of Northeastern Brazil Sample Locality Geographical coordinates Date of Weight Oil volume Yield / S W collection (leaves) / g / ml (% m/v) Major constituent Ceará State CE-1 Acarape /02/ (Z)-β-ocimene 04/12/ (Z)-β-ocimene CE-2 Acarape /02/ (Z)-β-ocimene CE-3 Acarape /02/ Δ 3 -carene 04/12/ Δ 3 -carene CE-4 Russas /26/ α-pinene 01/29/ α-pinene 02/10/ α-pinene CE-5 Acarape /04/ (Z)-β-ocimene CE-6 Acarape /04/ (Z)-β-ocimene CE-7 Tabuleiro do Norte /04/ limonene CE-8 Crateús /11/ Δ 3 -carene 05/21/ Δ 3 -carene CE-9 Crateús /11/ (Z)-β-ocimene 05/21/ (Z)-β-ocimene CE-10 highway BR /25/ α-pinene CE-11 highway BR /25/ (E)-β-ocimene CE-12 highway BR /25/ Δ 3 -carene CE-13 highway BR /26/ α-pinene CE-14 highway BR /26/ Δ 3 -carene CE-15 highway BR /22/ Δ 3 -carene CE-16 highway BR /22/ Δ 3 -carene CE-17 highway BR /22/ α-pinene CE-18 highway BR /26/ (E)-β-ocimene CE-19 highway BR /26/ Δ 3 -carene CE-20 highway BR /26/ limonene CE-21 highway BR /26/ Δ 3 -carene CE-22 highway BR /26/ Δ 3 -carene CE-23 Cajueiro Jaburuna /28/ Δ 3 -carene CE-24 Cajueiro Jaburuna /28/ limonene CE-25 Paramoti /19/ Δ 3 -carene CE-26 Paramoti /19/ Δ 3 -carene CE-27 Paramoti /19/ Δ 3 -carene CE-28 Paramoti /19/ α-pinene CE-29 Paramoti /19/ Δ 3 -carene CE-30 Paramoti /19/ Δ 3 -carene CE-31 Sobral /26/ (Z)-β-ocimene CE-32 Acarape /19/ (E)-β-ocimene
13 Table S2. Experimental data of essential oils from leaves of 62 wild specimens of aroeira-do-sertão from locations at different states of Northeastern Brazil (cont.) Sample Locality Geographical coordinates Date of Weight Oil volume Yield / S W collection (leaves) / g / ml (% m/v) Major constituent Rio Grande do Norte State RN-1 Baraúna /29/ limonene RN-2 Baraúna /29/ myrcene 05/04/ myrcene 01/26/ myrcene 02/10/ myrcene RN-3 São José de Mipibu /29/ limonene RN-4 São José de Mipibu /29/ Δ 3 -carene RN-5 São José de Mipibu /29/ Δ 3 -carene RN-6 Apodi /05/ limonene RN-7 Baraúna /05/ Δ 3 -carene 01/27/ Δ 3 -carene RN-8 Baraúna /04/ limonene 01/27/ limonene RN-9 Baraúna /22/ myrcene RN-10 Baraúna /21/ limonene RN-11 Mossoró /08/ Δ 3 -carene RN-12 Mossoró /08/ Δ 3 -carene RN-13 Baraúna /08/ limonene RN-14 Baraúna /30/ α-pinene RN-15 Baraúna /30/ α-pinene RN-16 Baraúna /30/ limonene RN-17 Baraúna /30/ α-pinene Bahia State BA-1 highway BR /25/ Δ 3 -carene BA-2 highway BR /25/ (Z)-β-ocimene BA-3 highway BR /25/ myrcene BA-4 highway BR /25/ limonene Pernambuco State PE-1 highway BR /25/ myrcene PE-2 highway BR /26/ limonene PE-3 highway BR /26/ α-pinene PE-4 highway BR /26/ limonene Piauí State PI-1 highway BR /26/ (E)-β-ocimene PI-2 highway BR /26/ α-pinene PI-3 Piripiri /23/ (E)-β-ocimene PI-4 Piracuruca /23/ (E)-β-ocimene PI-5 Piracuruca /23/ (E)-β-ocimene
14 Table S2. 13 C NMR data (ppm, 125 MHz, CDCl 3 ) representative of the major constituents of the essential oils from the whole fresh leaves of M. urundeuva, and comparison with literature data 1,2 C OEFA CE-3 Δ 3 -Carene OEFA RN-8 Limonene OEFA RN-2 Myrcene OEFA CE-4 α-pinene OEFA CE-2 (Z)-β- Ocimene OEFA CE- 32 a C C C C C C C C C C a13 C NMR data for (E)-β-ocimene has not been reported previously. References 1. Chang, C. W. J.; Flament, I.; Matson, J. A.; Nishida, T.; Ohloff, G.; Wehrli, F. W.; Weinheimer, A. J.; Progress in the Chemistry of Organic Natural Products, vol. 36; Herz, W.; Grisebach, H.; Kirby, G. W., eds.; Springer-Verlag: New York, USA, Pouchert, C. J.; Behnke, J.; The Aldrich Library of 13 C and 1 H FT-NMR Spectra, vol. 1, 1 st ed.; Aldrich Chemical Co.: Milwaukee, 1983.
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