A Conformational Isomer of Soulattrolide from the Stem Bark of Calophyllum symingtonianum and Its Antibacterial Activity

Deny Susanti; Nissad Attoumani; Muhammad Taher; Mohd Fazlin Rezali; Md. Hossain Sohrab; Choudhury Mahmood Hasan; Zainul Amiruddin Zakaria

doi:10.20307/nps.2018.24.1.47

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Susanti, Attoumani, Taher, Rezali, Sohrab, Hasan, and Zakaria: A Conformational Isomer of Soulattrolide from the Stem Bark of Calophyllum symingtonianum and Its Antibacterial Activity

Original Article

Natural Product Sciences 2018;24(1):47-53.

Published online: 20 January 2018

DOI: https://doi.org/10.20307/nps.2018.24.1.47

A Conformational Isomer of Soulattrolide from the Stem Bark of Calophyllum symingtonianum and Its Antibacterial Activity

Deny Susanti¹, Nissad Attoumani², Muhammad Taher^3,^∗, Mohd Fazlin Rezali⁴, Md. Hossain Sohrab⁵, Choudhury Mahmood Hasan⁶, Zainul Amiruddin Zakaria⁷

¹Department of Chemistry, Faculty of Science, International Islamic University Malaysia, Jalan Sultan Ahmad Shah, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia

²Department of Biotechnology, Faculty of Science, International Islamic University Malaysia, Jalan Sultan Ahmad Shah, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia

³Department of Pharmaceutical Technology, Faculty of Pharmacy, International Islamic University Malaysia, Jalan Sultan Ahmad Shah, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia

⁴SIRIM Berhad (National Metrology Laboratory), Lot PT 4803, Bandar Baru Salak Tinggi, 43900 Sepang, Selangor, Malaysia

⁵Pharmaceutical Sciences Research Division, BCSIR Laboratories Dhaka, Dr. Qudrat-I-Khuda Road, Dhanmondi, Dhaka-1205, Bangladesh

⁶Manarat International University, Road No. 106, Gulshan-2, Dhaka, Bangladesh

⁷Department of Biomedical Sciences, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia

∗Author for correspondence Muhammad Taher, Department of Pharmaceutical Technology, Faculty of Pharmacy, International Islamic University Malaysia, Jalan Sultan Ahmad Shah, Bandar Indera Mahkota, 25200 Kuantan, Pah-ang, Malaysia Tel: +60-95704807; E-mail: mtaher@iium.edu.my

Received 2 August 2017 Revised 16 November 2017 Accepted 1 December 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

Callophylum symingtonianum (Guttiferae), an evergreen broad-leaved tree that usually grows in hill forests, can be found distributed in the Malay Peninsula. The barks, leaves, flowers and seeds is often used medicinally to treat diarrhea and rheumatism. In the present study, we isolated two inophyllum type coumarins, 12-O-ethylinophyllum D (1) and iso-soulattrolide (2) from the stembarks of C. symingtonianum together with their antibacterial activity. The compounds were isolated by chromatographic methods on a silica gel. The structures were established by spectroscopic methods including UV, IR, (1D and 2D) NMR and mass spectrometry as well as by comparison with several literature sources. The antibacterial activity of those compounds was tested using a disc-diffusion assay against Staphylococcus aureus, Bacillus cereus, Escherichia coli and Pseudomonas aeruginosa. Both compound exhibited mild inhibition against P. aeruginosa with both 111 µg/ml MIC value. Compound 2 also inhibits S. aureus with 25 µg/ml MIC value.

Keywords: Calophyllum symingtonianum, Guttiferae, Coumarins, Antibacterial.

References

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Fig. 1.

Structures of compounds 1 and 2 isolated from Calophyllum symingtonianum.

Fig. 2.

Structures of reported inophyllums 3 – 7.

Fig. 3.

Some probable structures of the compound

Fig. 4.

Chromanol ring conformational structures of reported inophyllums 3 – 7 and probable structures of the compound 2 (2, 8 – 10).

Table 1.

¹H NMR (60, 100 & 400 MHz) spectroscopic data of compounds 1 – 7 (CDCl₃, δ, ppm, J/Hz)

Proton	1^∗	2^∗	Soulattrolide (3)^∗∗ ⁶	Inophyllum A (4)^∗∗∗⁶	Inophyllum B (5)^∗ ⁸	Inophyllum D (6)^∗⁵	Inophyllum P (7)^∗ ⁸
3	5.96 (1H, s)	5.94 (1H, s)	5.94 (1H, s)	5.96 (1H, s)	5.97 (1H, s)	5.98 (1H, s)	5.97 (1H, s)
7	5.33 (1H, d, J=10.0)	5.30 (1H, d, J = 10.0)	5.35 (1H, d, J = 10.0)	5.37 (1H, d, J = 10.0)	5.37 (1H, d, J = 10.0)	5.36 (1H, d, J = 10.0)	5.37 (1H, d, J = 10.0)
8	6.54 (1H, d, J = 10.0)	6.51 (1H, d, J = 10.0)	6.53 (1H, d, J = 10.0)	6.55 (1H, d, J = 10.0)	6.53 (1H, d, J = 10.0)	5.66 (1H, d, J = 10.0)	6.54 (1H, d, J = 10.0)
10	4.56 (1H, dq, J = 6.4, 1.6)	4.63 (1H, dq, J = 6.4, 1.6)	4.31 (1H, m, J = 7.0, 10.0)	4.43 (1H, m, J = 7.0, 3.3)	) 3.96 (1H, dq, J = 6.4, 9.1)	4.56 (1H, dq, J = 6.7, 2.0)	4.29 (1H, dq, J = 6.3, 10.6)
11	2.07 (1H, ddq, J = 7.2, 2.0, 2.0)	, 3.01 (1H, ddq, J = 7.2, 2.0, 2.0)	1.78 (1H, m, J = 3.2, 10.0)	2.27 (1H, m)	1.97 (1H, ddq, J = 6.8, 9.1 7.8)	, 1.99 (1H, ddq, J = 7.2, 2.0, 2.0)	1.79 (1H, ddq, J = 3.3, 7.0, 10.6)
12	4.54 (1H, d, J = 2.0)	4.88 (1H, d, J = 1.4)	5.04 (1H, d, J = 3.2)	5.17 (1H, d, J = 5.4)	4.79 (1H, d, J = 7.8)	4.95 (1H, d, J = 2.0)	5.04 (1H, d, J = 3.3)
14	7.22 (1H, m)	7.23 (1H, m)				7.31–7.33 (1H, m)
15	7.35 (1H, m)	7.35 (1H, m)				7.29–7.30 (1H, m)
16	7.35 (1H, m)	7.35 (1H, m)	7.30 (5H, m)	7.30 (5H, m)	7.41, 7.31 (5H, m)	7.31–7.33 (1H, m)	7.42, 7.30 (5H, m)
17	7.35 (1H, m)	7.35 (1H, m)				7.29–7.30 (1H, m)
18	7.22 (1H, m)	7.23 (1H, m)				7.31–7.33 (1H, m)
19 20	0.90 (3H, s) 0.93 (3H, s)	0.89 (6H, s)	0.93 (6H, s)	0.94 (6H, s)	0.97 (3H, s) 0.91 (3H, s)	0.95 (6H, s)	0.93 (6H, s)
21	1.42 (3H, d, J = 6.8)	1.56 (3H, d, J = 6.4)	1.44 (3H, d, J = 7.0)	1.43 (3H, d, J = 7.0)	1.47 (3H, d, J = 6.4)	1.45 (3H, d, J = 6.7)	1.44 (3H, d, J = 6.3)
22	0.79 (3H, d, J = 7.2)	0.90 (3H, d, J = 7.6)	1.16 (3H, d, J = 7.2)	1.17 (3H, d, J = 7.2)	1.18 (3H, d, J = 6.8)	0.83 (3H, d, J = 7.2)	1.17 (3H, d, J = 7.0)
23	3.85 (2H, q, J = 7.2)	—	—	—	—	—	—
24	1.28 (3H, t, J = 6.8)	—	—	—	—	—	—

^∗ at 400 MHz;

^∗∗ 100 MHz;

^∗∗∗ at 60 MHz

Table 2.

¹³C NMR (100 MHz) spectroscopic data of compounds 1, 2, 4 – 7 (CDCl₃, δ, ppm)

Carbon	1	2	Inophyllum A (4)⁸	Inophyllum B (5)⁸	Inophyllum D (6)⁵	Inophyllum P (7)⁸
2	160.6	160.7	160.3	160.6	160.5	160.1
3	112.1	111.6	111.4	111.7	111.9	111.5
4	156.1	156.4	156.2	156.3	156.3	156.4
4a	103.5	103.2	103.1	103.1	103.4	103.6
4b	151.2	151.3	150.9	151.1	151.1	150.9
6	77.0	77.0	76.8	76.7	77.1	77.2
7	127.1	127.0	127.1	127.1	127.2	127.6
8	116.1	116.1	115.9	116.0	115.9	115.9
8a	105.9	106.0	106.3	106.0	106.0	106.3
8b	154.9	154.7	152.5	153.7	153.9	153.7
10	71.0	69.2	75.7	73.0	71.2	76.9
11	34.5	31.9	35.5	38.2	37.2	40.4
12	71.9	71.7	62.6	61.8	64.6	67.1
12a	102.0	101.6	105.5	106.1	103.9	106.1
12b	154.0	154.6	154.0	153.6	154.6	154.1
13	140.2	140.2	139.9	140.0	139.9	139.9
14	127.1	127.0	127.2	127.3	127.3	127.3
15	127.4	127.4	127.2	127.3	127.4	127.3
16	127.6	127.5	127.5	127.6	127.6	127.4
17	127.4	127.4	127.2	127.3	127.4	127.3
18	127.1	127.0	127.2	127.3	127.3	127.3
19	26.7	27.0	26.7	26.9	27.0	26.5
20	27.0	26.9	26.7	26.8	27.0	26.9
21	17.9	17.5	16.0	18.8	17.1	18.9
22	9.1	9.5	9.7	12.5	9.1	15.0
23	64.8	—	—	—	—	—
24	15.9	—	—	—	—	—

Table 3.

Epimers and diastereomers of the known inophyllums 4 – 7^∗

Known Inophyllums	10-Epimer	11-Epimer	12-Epimer	10,11-Diastereomer	11,12-Diastereomer	10,12-Diastereomer	10,11,12-Diastereomer
InophyllumA (4)	Inophyllum 2	Inophyllum B (5)	Inophyllum D (6)	Inophyllum 10	Inophyllum P (7)	Inophyllum 8	Inophyllum 9
Inophyllum B (5)	Inophyllum 10	Inophyllum A (4)	Inophyllum P (7)	Inophyllum 2	Inophyllum D (6)	Inophyllum 9	Inophyllum 8
Inophyllum D (6)	Inophyllum 8	Inophyllum P (7)	Inophyllum A (4)	Inophyllum 10	Inophyllum B (5)	Inophyllum 2	Inophyllum 10
Inophyllum P (7)	Inophyllum 9	Inophyllum D (6)	Inophyllum B (5)	Inophyllum 8	Inophyllum A (4)	Inophyllum 10	Inophyllum 2

^∗ Bolded inophyllums are new

Table 4.

Antibacterial activity of the isolated compounds

Microorganisms	Compound 1		Compound 2		Chloramphenicol
	Inhibition zone (cm)	MIC (µg/mL)	Inhibition zone (cm)	MIC (µg/mL)	Inhibition (cm)
Staphylococcus aureus	–	–	1.30 ± 0.57	52.5 ± 0.28	2.8 ± 0.50
Bacillus cereus	–	–	–	–	2.7 ± 0.76
Escherichia coli					3.8 ± 0.50
Pseudomonas aeruginosa	0.70 ± 0.28	1.11 ± 0.50	51.0 ± 0.50	1.11 ± 0.50	2.4 ± 0.57

-: No activity; ±: Standard deviation

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