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Kim, Cha, Kim, Lee, and Lee: A New Steroidal Glycoside from Allium macrostemon Bunge
Original Article

Natural Product Sciences 2018;24(1):54-58.

Published online: 20 January 2018

DOI: https://doi.org/10.20307/nps.2018.24.1.54

A New Steroidal Glycoside from Allium macrostemon Bunge

Yun Sik Kim, Joon Min Cha, Dong Hyun Kim, Tae Hyun Lee, Kang Ro Lee∗

Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon 16419, Korea

∗Author for correspondence Kang Ro Lee, Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon 16419, Korea Tel: +82-31-290-7710; E-mail: krlee@skku.edu

Received 17 August 2017       Revised 30 October 2017       Accepted 31 October 2017

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

A phytochemical investigation of Allium macrostemon Bunge (Liliaceae) afforded the new pregnane steroidal glycoside, named allimacroside F (1), along with three known glycosides, benzyl-O-α-L-rhamnopy-ranosyl-(1 → 6)-β-D-glucopyranoside (2), phenylethyl-O-α-L-rhamnopyranosyl-(1 → 6)-β-D-glucopyranoside (3), (Z)-3-hexenyl-O-α-L-rhamnopyranosyl-(1 →6)-β-D-glucopyranoside (4). The identification and structural elucidation of a new compound (1) was carried out based on spectral data analyses (1H-NMR,13C-NMR,1H–1H COSY, HSQC, HMBC, and NOESY) and HR-FAB-MS.

Keywords: Allium macrostemon, Liliaceae, Steroidal glycoside, Allimacroside F.

References

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Fig. 1.
The structures of 1 – 4 isolated from A. macrostemon.
nps-24-54f1.tif
Fig. 2.
Key HMBC (HC), 1H-1H COSY (—) correlations 1 (A), and NOESY () correlations of 1 (B).
nps-24-54f2.tif
Table 1.
1H and 13C NMR data of 1 in Pyridine-d5. (δ in ppm, 700 MHz for 1H and 175 MHz for 13C)a
Position 1 Position 1
δH δC 1 δH δC
1 1.59 m, 0.90 m 38.6 Gal 1' 4.87 d (7.7) 104.0
2 2.06 m, 1.66 m 31.4 2' 4.41 m 74.5
3 3.85 m 79.4 3' 4.07 m 76.4
4 2.65 dd (13.3, 2.4), 2.40 t-like (12.2) 40.5 4' 4.57 m 81.4
5 – 142.8 5' 3.94 m 76.6
6 5.29 br d (5.2) 122.6 6' 4.65 m, 4.15 m 61.8
7 1.83 m, 1.52 m 33.0 Glc 1'' 5.12 d (7.8) 106.4
8 1.49 m 31.6 2'' 4.37 m 82.7
9 0.89 m 52.0 3'' 4.13 m 89.2
10 – 38.3 4'' 3.77 m 72.0
11 1.45 m, 1.45 m 22.2 5'' 3.82 m 78.8
12 2.58 m, 1.34 m 36.4 6'' 4.45 m, 3.98 m 64.3
13 – 47.5 Glc 1''' 5.55 d (7.7) 106.2
14 1.26 m 57.7 2''' 4.03 m 77.5
15 2.12 ddd (16.9, 6.5, 3.3) 1.85 m 33.6 3''' 4.18 m 79.5
16 6.58 dd (2.9, 1.8) 146.0 4''' 4.13 m 72.9
17 – 156.5 5''' 3.82 m 79.8
18 0.90 s 17.2 6''' 4.55 m, 4.27 m 63.8
19 0.86 s 20.5 Glc 1'''' 5.25 d (7.7) 105.3
20 – 197.6 2'''' 4.02 m 76.0
21 2.23 s 28.4 3'''' 4.18 m 78.0
      4'''' 4.21 m 82.7
      5'''' 3.99 m 77.9
      6'''' 4.51 m, 4.22 m 63.0
      Glc 1''''' 5.11 d, (7.5) 106.3
      2''''' 4.04 m 76.1
      3''''' 3.89 m 80.0
      4''''' 4.22 m 72.2
      5''''' 4.10 m 79.1
      6''''' 4.55 m, 4.36 m 63.7

a J values are in parentheses and reported in Hz; the assignments were based on1H-1H COSY, HMQC, and HMBC experiments.

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