Cytotoxic sesquiterpene lactones from the aerial parts of Inula aucheriana.

Gohari, Ahmad Reza; Mosaddegh, Mahmoud; Naghibi, Farzaneh; Eslami-Tehrani, Bahara; Pirani, Atefeh; Hamzeloo-Moghadam, Maryam; Read, Roger W.

doi:10.1590/0001-3765201520140063

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Biological Sciences • An. Acad. Bras. Ciênc. 87 (2) • Apr-Jun 2015 • https://doi.org/10.1590/0001-3765201520140063 copy

Cytotoxic sesquiterpene lactones from the aerial parts of Inula aucheriana.

Authorship SCIMAGO INSTITUTIONS RANKINGS

Inula aucheriana DC is a member of the family Asteraceae which is known to produce cytotoxic secondary metabolites noted as sesquiterpene lactones. In the present study, sesquiterpene lactones inuchinenolide B, 6-deoxychamissonolide (stevin) and 14-acetoxy-1β,5α,7αH-4β-hydroxy-guai-9(10),11(13)-dien-12,8α-olide were isolated from I. aucheriana. Inuchinenolide B and 14-acetoxy-1β,5α,7αH-4β-hydroxy-guai-9(10),11(13)-dien-12,8α-olide were further evaluated by the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay to demonstrate cytotoxic activity with IC₅₀ values of (56.6, 19.0), (39.0, 11.8), and (55.7, 15.3) μg/mL against HepG-2, MCF-7 and A-549 cells, respectively. The cytotoxic activity of the two evaluated sesquiterpene lactones partly explains the cytotoxic activity that was previously observed for the extracts of Inula aucheriana. The isolated compounds could be further investigated in cancer research studies.

cytotoxicity; Inula aucheriana; MTT assay; sesquiterpene lactones

No.	A				C
	δ_H (mult, J/Hz)	δ_C	COSY	HMBC	δ_H (mult, J/Hz)	δ_C	COSY	HMBC
1	-	135.8	-	-	1.86 (m)	52.8	H-2	C-2, 15
2	5.46 (t, 7.6)	72	H-3a, b	C-1, 10, 17	4.93 (tw, 7.8)	74.9	H-1	C-4, 5, 17
3a	1.72 (dd, 7.8, e12.6)	46.9	H-2	C-2, 4, 14	1.84	38.4	H-2, 4	C-4, 7, 9
3b	2.48 (dd, 7.6, 12.6)		H-2	C-1, 4, 5, 14	2.06		H-2, 4	C-2, 4,
4	-	77	-	-	4.04	80.6	H-3	C-6, 15
5	2.70 (brd, 11.5)	52.2	H-6	-	-	27.1	-	-
6a	1.48 (m)	25	H-5, 7	C-1, 5, 7	1.41	38.0	H-7	C-1, 15
6b	2.26 (m)		H-7	C-5, 7	2.33		H-7	C-7, 8, 15
7	3.3 (m)	41.9	H-8	-	2.82	45.1	H-8, 13	-
8	4.88 (m)	78.7	H-9a, b	-	4.24	81.4	H-7, 9	-
9a	2.26 (m)	36.6	H-8	C-1, 7, 8, 10, 15	1.40	44.0	H-8	C-7, 8, 9, 11, 14
9b	2.56 (m)		H-8	-	2.37		H-8	-
10	-	131.8	-	-	1.97	29.1	H-1, 9, 14	-
11	-	138.3	-	-	-	140.4	-	-
12	-	169.9	-	-	-	169.5	-	-
13a	5.64 (d, 3.0)	122	H-7	C-7, 12	5.46	119.8	H-7	C-7, 12
13b	6.32 (d, 3.0)		H-7	C-7, 11, 12	6.18		H-7	C-7, 11, 12
14	1.05 (s)	22.7	-	C-3, 4, 5	0.97	19.9	-	C-1, 9, 10
15	1.66 (s)	21.6	-	C-1, 9, 10	0.93	18.7	-	C-1, 4, 6, 7
16	-	170.7	-	-	-	170.5	-	-
17	2.06 (s)	20.9	C-16	-	2.04	21.3	-	C-17

No.	B
	δ_H (mult, J/Hz)	δ_C	COSY	HMBC
1	2.58^* (m)	45.0	H-5	C-5, 9, 10/11
2a	1.78 (m)	23.7	H-1, 3	C-1/7, 4, 5
2b	1.88 (m)		H-1, 3	C1/7, 3, 4, 10
3a	1.67 (m)	41.5	H-2	C-1, 2, 4, 5
3b	1.80 (m)		Ha-3	C-1, 2, 4
4	-	79.5	-	-
5	1.63 (m)	52.5	H-1, 6	C-1/7, 4, 10
6a	1.43 (m)	31.0	H-5,7	C-5, 1/7, 8
6b	2.50 (m)		Ha-6	C-1/7
7	2.58^* (m)	45.2	H-8, Hb-13	C-5, 9, 10/11
8	4.76 (d, 9.3)	81.7	H-9	C-1/7, 6,9, 10/11
9	6.15 (brs)	129.9	H-8, 14	C-1/7, 14
10	-	138.6	-	-
11	-	139.0	-	-
12	-	169.9	-	-
13a	5.53 (d, 2.8)	119.7	H-7	C1/7, 12
13b	6.21 (d, 2.8)		H-7	C-1/7, 11, 12
14	4.63 (s)	65.5	H-9	C-1/7, 9, 10, 16
15	1.24 (s)	31.4	-	C-3, 4, 5
16	-	170.5	-	-
17	2.10 (s)	20.9	-	C-14, 16

	IC₅₀ µg/mL
	HepG-2	A-549	MCF-7
inuchinenolide B	56.6	55.7	39.0
aucherinolide	19.0	15.3	11.8

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[1] Correspondence to: Maryam Hamzeloo-Moghadam E-mail: mhmoghadam@itmrc.org