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Ismed, Arifa, Bakhtiar, Umeda, Putra, Yonemochi, and Zaini: Ethyl Haematommate from Stereocaulon graminosum Schaer.: Isolation and Crystal Structure
Original Article

Natural Product Sciences 2018;24(2):115-118.

Published online: 20 January 2018

DOI: https://doi.org/10.20307/nps.2018.24.2.115

Ethyl Haematommate from Stereocaulon graminosum Schaer.: Isolation and Crystal Structure

Friardi Ismed1, ∗, Nurwahidatul Arifa1, Amri Bakhtiar1, Daiki Umeda2, Okky Dwichandra Putra2, 3, Etsuo Yonemochi2, ∗, Erizal Zaini1

1The Laboratory of Natural Resource of Sumatra and Faculty of Pharmacy, Andalas University, 26163 Padang, Indonesia

2School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41, Ebara, Shinagawa, Tokyo 142–8501, Japan

3Current Address: Pharmaceutical Technology and Development, AstraZeneca, Pepparedsleden 1, Mölndal S-431 83, Sweden

∗Author for correspondence Friardi Ismed, The Laboratory of Natural Resource of Sumatra and Faculty of Pharmacy, Andalas University, 26163 Padang, Indonesia. E-mail: friardi@ffarmasi.unand.ac.id

Received 13 December 2017       Revised 29 February 2018       Accepted 22 February 2018

Copyright © 2018 The Korean Society of Pharmacognosy

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

Herein, we reported the phytochemical investigation of whole thallus Sumatran lichen, Stereocaulon graminosum Schaer, and isolated a mono aromatic compound, ethyl haematommate (1). The structure of compound 1 have been established based on spectroscopic data and confirmed by single crystal X-ray structure analysis.

Keywords: Stereocaulon, Lichen, Mono aromatic, Crystal structure

References

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Fig. 1.
Chemical structure of compound 1 isolated from lichen S. graminosum.
nps-24-115f1.tif
Fig. 2.
Key HMBC correlations of compound 1.
nps-24-115f2.tif
Fig. 3.
Thermal ellipsoid structures of compound 1 with atom labelling drawn at a 50% probability level. The asymmetric unit contained one molecule of compound 1.
nps-24-115f3.tif
Fig. 4.
The π–π interactions in compound 1 create a layered architecture propagating in the (001) plane. Hydrogen atoms are omitted for clarity.
nps-24-115f4.tif
Table 1.
1H- and 13C-NMR data of ethyl haematommate (1) in CDCl3 (δ in ppm, 500 MHz for 1H and 125 MHz for 13C)a
Position Compound 1
δH δC
1 – 104.4
2 – 152.6
3 6.27 (1H, s) 112.2
4 12.39 (1H, s) 166.7
5 – 108.6
6 12.97 (1H, s) 168.5
CHO-7 10.33 (1H, s) 194.4
CH3-8 2.53 (3H, d, J = 7.15) 25.4
CO-9 – 171.7
OCH2-10 4.43(2H, bd, J = 7.10) 62.1
CH3-11 1.42 (3H, t, J = 7.1) 14.3

a J value are in parentheses and reported in Hz

Table 2.
Crystallographic data of compound 1
Chemical formula C11H12O5
Mr 224.21
Crystal system, space group Orthorhombic, P212121
Temperature (K) 93
a, b, c (Å) 6.7257 (4), 12.1568 (7), 12.3739 (8)
Tmin, Tmax 0.455, 0.905
No. of measured, independent, and observed [I > 2σ(I)] reflections 11356, 1848, 1490
Rint 0.079
(sin θ/λ)max (Å−1) 0.602
Tmin, Tmax 0.455, 0.905
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.101, 0.96
No. of reflections 1848
Table 3.
Hydrogen-bond geometry of compound 1
D−H···A D−H (Å) H···A(Å) D···A (Å) D−H···A (°)
O1−H···O4 0.98 (3) 1.63 (4) 2.509 (2) 146 (3)
O3−H···O2 0.90 (3) 1.76 (3) 2.581 (3) 151 (3)
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