Neolignan Derivatives from the Flower of Magnolia biondii Pamp. and their Effects on IL-2 expression in T-cells

Thi Tuyet Mai Nguyen; Thi Thu Nguyen; Hyun-Su Lee; Chang-Duk Jun; Byung Sun Min; Jeong Ah Kim

doi:10.20307/nps.2017.23.2.119

Journal List > Nat Prod Sci > v.23(2) > 1060653

Go to TopGo to Top Go to BottomGo to Bottom

TOOLS

Nguyen, Nguyen, Lee, Jun, Min, and Kim: Neolignan Derivatives from the Flower of Magnolia biondii Pamp. and their Effects on IL-2 expression in T-cells

Original Article

Natural Product Sciences 2017;23(2):119-124.

Published online: 20 January 2017

DOI: https://doi.org/10.20307/nps.2017.23.2.119

Neolignan Derivatives from the Flower of Magnolia biondii Pamp. and their Effects on IL-2 expression in T-cells

Thi Tuyet Mai Nguyen¹, Thi Thu Nguyen¹, Hyun-Su Lee^2,³, Chang-Duk Jun², Byung Sun Min³, Jeong Ah Kim^1,^∗

¹College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, Daegu 41566, Republic of Korea

²School of Life Sciences, Immune Synapse Research Center and Cell Dynamics Research Center, Gwangju Institute of Science and Technology, Gwangju 61005, Republic of Korea

³College of Pharmacy, Drug Research and Development Center, Catholic University of Daegu, Gyeongbuk 38430, Republic of Korea

∗Author for correspondence Jeong Ah Kim, College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, Daegu 41566, Republic of Korea Tel: +82-53-950-8574; E-mail: jkim6923@knu.ac.kr

Received 6 January 2017 Revised 3 April 2017 Accepted 3 April 2017

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The isolation of the MeOH extract from the flower bud of Magnolia biondii Pamp. using various column chromatographies and HPLC led to eleven neoglignan derivatives (1 – 11). Their structures were mainly determined by 1D and 2D NMR spectral data analysis and physiological methods. The isolated compounds (1 – 11) were tested for anti-allergic effects using IL-2 inhibitory assay in Jurkat T cells.

Go to :

Keywords: Magnolia biondii Pamp., Magnoliaceae, Neolingnan, Anti-allergy, IL-2

References

(1). Park C. S.., Kim T. B.., Lee J. Y.., Park J. Y.., Lee Y. C.., Jeong S. S.., Lee Y. D.., Cho Y. S.., Moon H. B.Korean J. Intern. Med. 2012. 27:84–90.

(2). Song Q.., Fischer N. H.Rev. Soc. Quím. Mex. 1999. 43:211–218.

(3). Marin G. H.., Mansilla E.., Ciocchini S.., Quiroga N.., Cardozo N.., Weiss M.., Gustavo H. M.., Trebucq H.Annalen der Chemischen Forschung. 2013. 1:50–55.

(4). Lee S.., Chappell J.Plant Physiol. 2008. 147:1017–1033.

(5). Haraguchi H.., Ishikawa H.., Shirataki N.., Fukuda A. J.Pharm. Pharmacol. 1997. 49:209–212.

(6). Syu W. J.., Shen C. C.., Lu J. J.., Lee G. H.., Sun C. M.Chem. Biodivers. 2004. 1:530–537.

(7). Kuo W. L.., Chung C. Y.., Hwang T. L.., Chen J. J.Phytochemistry. 2013. 85:153–160.

(8). Akber U.., Na B. R.., Ko Y. S.., Lee H. S.., Kim H. R.., Kwon M. S.., Park Z. Y.., Choi E. J.., Han W. C.., Lee S. H.., Oh H. M.., Jun C. D.Int. Immunopharmacol. 2015. 25:130–140.

(9). Hershko A. Y.., Suzuki R.., Charles N.., Alvarez-Errico D.., Sargent J. L.., Laurence A.., Rivera J.Immunity. 2011. 35:562–571.

(10). Chen C. C.., Huang Y. L.., Chen Y. P.., Hsu H. Y.., Kuo Y. H.Chem. Pharm. Bull. 1988. 36:1791–1795.

(11). Tyagi O. D.., Jensen S.., Boll P. M.., Sharma N. K.., Bisht K. S.., Parmar V. S.Phytochemistry. 1993. 32:445–448.

(12). Ponpipom M. M.., Bugianesi R. L.., Brooker D. R.., Yue B. Z.., Hwang S. B.., Shen T. Y. J.Med. Chem. 1987. 30:136–142.

(13). Wenkert E.., Gottlieb H. E.., Gottlieb O. R.., Pereira M. O. S.., Formiga M. D.Phytochemistry. 1976. 15:1547–1551.

(14). Jensen S.., Olsen C. E.., Tyagi O. D.., Boll P. M.., Hussaini F. A.., Gupta S.., Bisht K. S.., Parmar V. S.Phytochemistry. 1994. 36:789–792.

(15). Tyagi O. D.., Wengel J.., Prasad A. K.., Boll P. M.., Olsen C. E.., Pati H. N.., Bisht K. S.., Parmar V. S.Acta Chem. Scand. 1994. 48:1007–1011.

(16). El-Feraly F. S.., Cheatham S. F.., Hufford C. D.., Li W. S.Phytochemistry. 1982. 21:1133–1135.

(17). Pieters L.., de Bruyne T.., Claeys M.., Vlietinck A.., Calomme M.., vanden Berghe D. J.Nat. Prod. 1993. 56:899–906.

(18). Kuroyanagi M.., Yoshida K.., Yamamoto A.., Miwa M.Chem. Pharm. Bull. 2000. 48:832–837.

(19). Du J.., Wang M. L.., Chen R. Y.., Yu D. Q. J.Asian Nat. Prod. Res. 2001. 3:313–319.

(20). Kasperska-Zajac A.., Brzoza Z.., Rogala B.Recent Pat. Inflamm. Allergy Drug Discov. 2008. 2:72–76.

(21). Noshita T.., Funayama S.., Hirakawa T.., Kidachi Y.., Ryoyama K.Biosci. Biotechnol. Biochem. 2008. 72:2775–2778.

(22). Reddy S. D.., Siva B.., Poornima B.., Kumar D. A.., Tiwari A. K.., Ramesh U.., Babu K. S.Pharmacogn. Mag. 2015. 11:235–241.

Go to :

Fig. 1.

Chemical structures of neolignans 1 – 11 isolated from the flower of Magnolia biondii Pamp.

undefined

Fig. 2.

Inhibition of IL-2 expression and cell viability by neolignans 1–11 isolated from M. biondii. A) Jurkat T cells (1 × 10⁶) were treated with 50 µM concentrations of 1 – 11 for 30 min and stimulated with PMA (100 nM)/A23187 (1 µM) for 6 h. After incubation, cells were harvested and total RNA was isolated from harvested cells. Human IL-2 mRNA levels were detected by conventional PCR. B) Jurkat T cells (3×10⁵) were seeded in a 24 well-plate and incubated with 50 µM concentrations of 1–11 for 24 h. After incubation, cell viability was examined by MTT assay. Data was shown as percentages compared to cell viability treated with Mock control.

undefined

Table 1.

¹H NMR spectroscopic data for compounds 1 – 7 (δ values)^a

Position	1^b	2^b	3^c	4^c	5^c	6^c	7^c
2	6.81, s		6.82, d (1.5)			6.78, m	6.92, m
5	6.77, brs	6.70, m	6.78, d (8.0)	6.96, m	6.85, m	6.84, d (8.4)	6.87, d (7.9)
6	6.77, brs		6.75, dd (8.0, 1.5)			6.78, m	6.92, m
7	4.70, d (10.3)	4.24, d (3.6)	4.09, d (10.9)	5.41, d (10.1)	5.42, d (10.0)	6.14, d (5.1)	4.68, dd (17.0, 2.0)
8	2.22, dd (10.3, 6.7)	2.69, m	2.73, m	2.30, dq (9.5, 6.8)	2.30, m	2.83, dd (7.3, 5.1)	2.82, q (7.2)
9	1.07, d (6.7)	1.06, d (7.0)	0.97, d (7.0)	1.15, d (6.8)	1.17, d (6.9)	0.50, d (7.3)	1.21, d (7.2)
1'	2.74, m	2.09, m
2'	4.43, d (8.8)	4.25, s		6.42, s	5.80, s	5.84, s	5.81, s
5'		5.56, s		5.71, s	5.67, s	5.77, s	5.76, s
					2.46, dd	2.68, dd	2.23, dd
7'	2.57, m, 2.74, m	2.37, m, 2.86, m	3.12, ddd (6.7, 2.5, 1.2)	3.11, dd (6.8, 1.2), 3.16, dd (6.8, 1.2)	(13.6, 7.3), 2.68, dd	(13.5, 7.0), 2.77, dd	(13.4, 6.8), 2.35, dd
					(13.6, 7.3)	(13.5, 7.8)	(13.4, 8.0)
8'	5.90, m	5.92, m	6.54, d (1.2)	5.92, ddt (16.9, 10.1, 6.9)	5.53, ddt (17.3, 10.1, 7.3)	5.72, m	5.54, dddd (17.0, 10.2, 7.9, 6.8)
9'	5.10, dd (9.9, 1.5), 5.17, dd (17.3, 1.5)	5.05, m, 5.15, dd (17.1, 1.5)	5.14, m	5.13, m	5.04, ddd (18.8, 13.6, 1.9)	5.14, t (12.2)	5.00, dd (10.2, 2.0), 5.47, d (0.96)
–OCH₂O-	– 5.95, s	5.92, m	5.95, s		5.97, s	5.96, s	5.99, s
3-OCH₃				3.82, s
4-OCH₃
3'-OCH₃	3.21, s	3.32, s	3.19, s	3.82, s	3.14, s	3.69, s	3.67, s	3.67, s
4'-OCH₃	3.76, s	3.73, s	3.41, s

^a δ value recorded in ppm (J in Hz).

^b 1H NMR measured at 500 MHz in CDCl₃.

^c 1H NMR measured at 500 MHz in CD₃OD.

Table 2.

¹H NMR spectroscopic data for compounds 8 – 11 (δ values)^a

Position	8	9	10	11
2	6.98, d (2.0)	6.95, s	6.58, d (2.0)	6.39, s
5	6.84, d (8.2)	6.82, d (8.7)	6.79, d (8.2)
6	6.96, dd (8.2, 2.0)	6.95, s	6.66, dd (8.2, 2.1)	6.39, s
7 8	5.12, d (9.5) 3.46, m	5.55, d (7.4) 3.60, dd (12.2, 5.8)	2.46, m	2.57, d (6.1) 2.07, m
9	1.38, d (6.8)	3.90, d (4.6), 3.96, dd (10.9, 5.8)	1.07, d (6.1)	0.62, d (6.5)
2'	6.79, s	6.67, d (2.2)
3'			3.52, m	5.80, s
6'	6.77, s	6.67, d (2.2)	7.04, s	5.49, s
7'	6.36, dd (15.7, 1.6)	2.65, d (7.9)	3.12, dd (16.4, 8.6)	2.22, d (11.3), 2.39, ddd (11.3, 6.4, 1.4)
8'	6.11, dq (15.7, 6.6)	1.88, m	5.86, ddt (17.6, 10.9, 6.8)	5.05, m
9'	1.87, dd (6.6, 1.6)	3.68, d (6.3)	5.17, d (6.3), 5.20, s	1.76, dd (12.0, 11.9), 2.32, m
3-OCH₃	3.89, s	3.86, s	3.86, s	3.85, s
4-OCH₃	3.89, s	3.85, s	3.86, s	3.82, s
5-OCH₃				3.85, s
3'-OCH₃	3.89, s	3.88, s
5'-OCH₃			3.64, s	3.68, s

^a δ value recorded in ppm (J in Hz) and

¹ H NMR measured at 500 MHz in CDCl₃.

Table 3.

¹³C NMR spectroscopic data for compounds 1 – 11 (δ values)^a

Position	1^b	2^b	3^c	4^c	5^c	6^c	7^c	8^b	9^b	10^b	11^b
1	134.4	134.2	135.5	131.3	133.1	133.2	136.4	132.8	133.9	134.0	139.1
2	106.9	106.7	108.8	111.2	107.8	107.3	106.0	109.7	109.5	110.2	104.8
3	148.0	147.9	149.5	151.3	149.8	149.4	149.7	149.3	149.3	148.6	153.4
4	147.6	147.5	149.1	150.8	149.6	148.8	148.6	146.8	149.1	149.6	137.0
5	108.2	108.1	108.1	112.8	109.1	109.2	109.3	110.0	111.1	111.7	153.4
6	120.5	120.1	122.2	121.2	120.2	120.4	120.3	119.4	118.8	119.5	104.8
7	87.2	86.1	86.8	93.3	92.8	89.3	94.9	93.8	87.9	49.0	45.4
8	51.4	48.5	50.6	51.5	37.1	44.2	46.4	45.8	53.9	45.5	37.9
9	8.9	11.2	9.4	6.9	8.3	12.4	18.8	17.8	64.1	13.8	14.6
1'	52.8	54.1	144.5	143.9	53.2	55.8	55.0	132.4	135.5	140.6	50.4
2'	80.0	81.1	140.2	133.6	111.1	112.3	112.1	109.4	112.6	194.5	180.0
3'	84.7	82.3	83.3	79.3	154.3	153.8	153.7	144.3	144.3	70.0	101.5
4'	172.4	173.4	103.4	177.4	185.7	185.5	185.4	149.3	146.7	202.4	183.1
5'	105.7	103.5	44.2	102.9	102.8	102.6	102.7	133.4	127.9	89.5	153.4
6'	196.4	196.9	196.1	189.2	185.3	185.1	185.3	113.5	116.1	147.3	108.9
7'	31.3	29.2	34.5	34.6	50.9	46.5	46.7	131.1	32.1	32.9	60.9
8'	135.4	136.4	136.4	136.6	132.6	132.2	132.9	123.7	34.7	133.9	81.9
9'	117.9	117.0	117.6	117.5	122.1	120.2	118.4	18.5	62.4	118.3	43.7
–OCH₂O-	101.2	101.2	102.5	−	101.9	102.2	102.7	−	−	−	−
3-OCH₃	−	−	−	56.5	−	−	−	56.1	56.2	56.1	56.2
4-OCH₃	−	−	−	56.5	−	−	−	56.1	56.2	56.1	60.9
5-OCH₃	−	−	−	−	−	−	−	−	−	−	56.2
3'-OCH₃	51.5	53.4	47.7	51.6	55.8	56.2	55.8	56.8	56.1	−	−
4'-OCH₃	56.4	56.1	51.4	−	−	−	−	−	−	−	−
5'-OCH₃	−	−	−	−	−	−	−	−	−	54.1	55.3

^a δ value recorded in ppm.

^b 13C NMR measured at 125 MHz in CDCl₃.

^c 13C NMR measured at 125 MHz in CD₃OD.

TOOLS

Similar articles