Journal List > Nat Prod Sci > v.24(1) > 1060699

Kim, Kim, and Choi: Lipids in Ginseng (Panax ginseng) and Their Analysis

Abstract

Ginseng (Panax ginseng) is recognized as one of the most valuable medicinal herbs in Asia and it contains diverse phytochemicals that contribute to its pharmacological effects. Although lipids represent a major component of ginseng, ginseng lipids are still far from being fully explored. This review is focused on ginseng lipid components and methodologies of their analysis. The ginseng lipid compounds were categorized according to the structural features of each lipid class. This basic information on ginseng lipid components and the analysis methods will be applicable to authentification or quality control of ginseng products, and development of lipid-based pharmaceuticals and nutraceuticals from ginseng.

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Fig. 1.
Representative chemical structures of fatty acyls (palmitic acid, α-linolenic acid, (3R, 9R, 10S)-panaxydol, (3R, 9R, 10R)-panaxytriol, 2,4-decadienal) in ginseng.
nps-24-1f1.tif
Fig. 2.
Representative chemical structures of glycerolipids (triacylglycerol (18:2/18:2/18:2), monogalactosyldiacylglycerol (18:3/18:3), digalactosyldiacylglycerol (18:2/18:2)) in ginseng.
nps-24-1f2.tif
Fig. 3.
Representative chemical structures of glycerophospholipids (phosphatidylcholine (C16:0/18:1), phosphatidylethanolamine (C18:1/ 18:1), phosphatidylglycerol (C18:0/18:0)) in ginseng.
nps-24-1f3.tif
Fig. 4.
Representative chemical structures of sterol lipids (campesterol, β-sitosterol, stigmasterol) in ginseng.
nps-24-1f4.tif
Fig. 5.
Representative chemical structures of prenol lipids (myrcene, terpinolene, bicyclogermacrene, humulene, β-amyrin, lupeol) in ginseng.
nps-24-1f5.tif
Fig. 6.
Representative chemical structures of polyketides ((+)-catechin, formononetin, kaempferol, quercetin) in ginseng.
nps-24-1f6.tif
Table 1.
Lipid compounds of P. ginseng registered in LIPID MAPS
No. Compounds Category Main Class Sub Class LM ID Typical Class Analytical Tool a Sample
1 Hexanoic acid (C6:0) Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010006 Fatty acids GC-MS(22) Root (white ginseng)
      Conjugates [FA01] acids [FA0101]       (22)
2 Heptanoic acid Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010007 Fatty acids GC-MS(22) Root (white ginseng)
  (C7:0)   Conjugates [FA01] acids [FA0101]       (22)
3 Octanoic acid (C8:0) Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010008 Fatty acids GC-MS [22] Root (white ginseng)
      Conjugates [FA01] acids [FA0101]       (22)
4 Lauric acid (C12:0) Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010012 Fatty acids GLC-FID (23) Root (fresh and dried
      Conjugates [FA01] acids [FA0101]       ginseng) (23)
5 Myristic acid (C14:0) Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010014 Fatty acids GLC-FID (23) Root (fresh and dried
      Conjugates [FA01] acids [FA0101]       ginseng) (23)
6 Pentadecylic acid Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010015 Fatty acids GLC-FID (23) Root (fresh and dried
  (C15:0)   Conjugates [FA01] acids [FA0101]       ginseng) (23)
7 Palmitic acid (C16:0) Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010001 Fatty acids GLC-FID (23), Root (fresh and dried
      Conjugates [FA01] acids [FA0101]     GC-MS (24) ginseng) (23); Root
                (dried ginseng) (24)
8 Margaric acid Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010017 Fatty acids GLC-FID (23) Root (fresh and dried
  (C17:0)   Conjugates [FA01] acids [FA0101]       ginseng) (23)
9 Stearic acid (C18:0) Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010018 Fatty acids GLC-FID (23) Root (fresh and dried
      Conjugates [FA01] acids [FA0101]       ginseng) (23)
10 Arachidic acid Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010020 Fatty acids GLC-FID (23) Root (fresh and dried
  (C20:0)   Conjugates [FA01] acids [FA0101]       ginseng) (23)
11 Behenic acid (C22:0) Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010022 Fatty acids GLC-FID (23) Root (fresh and dried
      Conjugates [FA01] acids [FA0101]       ginseng) (23)
12 Lignoceric acid Fatty Acyls [FA] Fatty Acids and Straight chain fatty LMFA01010024 Fatty acids GLC-FID (23) Root (fresh and dried
  (C24:0)   Conjugates [FA01] acids [FA0101]       ginseng) (23)
13 Pentadecenoic acid Fatty Acyls [FA] Fatty Acids and Unsaturated fatty LMFA01030259 Fatty acids GLC-FID (23) Root (fresh and dried
  (C15:1)   Conjugates [FA01] acids [FA0103]       ginseng) (23)
14 cis-9-Palmitoleic acid Fatty Acyls [FA] Fatty Acids and Unsaturated fatty LMFA01030056 Fatty acids GLC-FID (23) Root (fresh and dried
  (C16:1)   Conjugates [FA01] acids [FA0103]       ginseng) (23)
15 Oleic acid (C18:1) Fatty Acyls [FA] Fatty Acids and Unsaturated fatty LMFA01030002 Fatty acids GLC-FID (23) Root (fresh and dried
      Conjugates [FA01] acids [FA0103]       ginseng) (23)
16 Linoleic acid (C18:2) Fatty Acyls [FA] Fatty Acids and Unsaturated fatty LMFA01030120 Fatty acids GLC-FID (23), Root (fresh and dried
      Conjugates [FA01] acids [FA0103]     GC-MS (24) ginseng) (23); Root
                (dried ginseng) (24)
17 α-Linolenic acid Fatty Acyls [FA] Fatty Acids and Unsaturated fatty LMFA01030152 Fatty acids GLC-FID (23) Root (fresh and dried
  (C18:3)   Conjugates [FA01] acids [FA0103]       ginseng) (23)
18 cis-Gondoic acid Fatty Acyls [FA] Fatty Acids and Unsaturated fatty LMFA01030085 Fatty acids GLC-FID (23) Root (fresh and dried
  (C20:1)   Conjugates [FA01] acids [FA0103]       ginseng) (23)
19 cis-Erucic acid Fatty Acyls [FA] Fatty Acids and Unsaturated fatty LMFA01030089 Fatty acids GLC-FID (23) Root (fresh and dried
  (C22:1)   Conjugates [FA01] acids [FA0103]       ginseng) (23)
20 Nervonic acid (C24:1) Fatty Acyls [FA] Fatty Acids and Conjugates [FA01] Unsaturated fatty acids [FA0103] LMFA01030092 Fatty acids GLC-FID (23) Root (fresh and dried ginseng) (23)
21 Panaxydol Fatty Acyls [FA] Fatty alcohols [FA05] LMFA05000028 Polyacetylenes HPLC-UV, NMR Root (dried ginseng)
22 Panaxynol Fatty Acyls [FA] Fatty alcohols [FA05] LMFA05000689 Polyacetylenes (27) IR, UV, NMR (26) (27) Root (dried ginseng)
23 Panaxytriol Fatty Acyls [FA] Fatty alcohols [FA05] LMFA05000027 Polyacetylenes HPLC-UV, IR, (26) Root (fresh ginseng)
24 Ginsenoyne A – K Fatty Acyls [FA] Fatty alcohols [FA05] LMFA05000661 Polyacetylenes NMR (28) UV, IR, NMR, (28) Root (white ginseng)
              HR-EIMS (30,31) (30,31)
25 10,12-Octadecadiynoic acid Fatty Acyls [FA] Fatty Acids and Conjugates [FA01] Unsaturated fatty acids [FA0103] LMFA01030542 Polyacetylenes GC-MS (24) Root (dried ginseng) (24)
26 Hexanal Fatty Acyls [FA] Fatty aldehydes [FA06]   LMFA06000109 Fatty aldehydes GC-MS (22) Root (white ginseng) (22)
27 Heptanal Fatty Acyls [FA] Fatty aldehydes [FA06]   LMFA06000001 Fatty aldehydes GC-MS (22) Root (white ginseng) (22)
28 Octanal Fatty Acyls [FA] Fatty aldehydes [FA06]   LMFA06000028 Fatty aldehydes GC-MS (22) Root (white ginseng) (22)
29 2,4-Decadienal Fatty Acyls [FA] Fatty aldehydes [FA06]   LMFA06000057 Fatty aldehydes GC-MS (22) Root (white ginseng) (22)
30 Oleamide Fatty Acyls [FA] Fatty amides [FA08] Primary amides [FA0801] LMFA08010004   GC-MS (24) Root (white ginseng) (24)
31 Monoacylglycerol s Glycerolipids [GL] Monoradylglycer-ols [GL01] Monoacylglycerols [GL0101] LMGL01010000 Neutral lipids; storage lipids TLC (23) Root (fresh and white ginseng) (23)
32 Diacylglycerols Glycerolipids [GL] Diradylglycerols [GL02] Diacylglycerols [GL0201] LMGL02010000 Neutral lipids; storage lipids TLC (23) Root (fresh and white ginseng) (23)
33 Triacylglycerols Glycerolipids [GL] Triradylglycerols [GL03] Triacylglycerols [GL0301] LMGL03010000 Neutral lipids; storage lipids TLC (23); nano-EIS-MS (35) Root (fresh and white ginseng) (23); Root, rhizome (fresh ginseng) (35)
34 Monogalactosyldia-cylglycerols (MGDG) Glycerolipids [GL] Glycosyldiradylg-lycerols [GL05] Glycosyldiacylglyc-erols [GL0501] LMGL0501AA00 Galactolipids TLC (23)nano-EIS-MS (35) Root (fresh and white ginseng) (23); Root, rhizome (fresh ginseng) (35)
35 Digalactosyldiacyl-glycerols (DGDG) Glycerolipids [GL] Glycosyldiradylg-lycerols [GL05] Glycosyldiacylglyc-erols [GL0501] LMGL0501AD00 Galactolipids TLC (23) Root (fresh and white ginseng) (23)
36 Phosphatidic acid (PA) Glycerophospholipid s [GP] Glycerophosphates [GP10] Diacylglycerophosph ates [GP1001] LMGP10010000 Phospholipids nano-ESI-MS (35) Root, rhizome (fresh ginseng) (35)
37 Phosphatidylchol (PC) line Glycerophospholipid [GP] ds Glycerophosphoc-holines [GP01] – Diacylglycerophos-phocholines LMGP01010000 Phospholipids TLC (23); nano-ESI-MS (35) Root (fresh and whit ginseng) (23); Root,
        [GP0101]       rhizome (fresh
                ginseng) (35)
38 Phosphatidyletha mine (PE) nola Glycerophospholipid [GP] ds Glycerophosphoe-thanolamines [GP – 02] Diacylglycerophos-phoethanolamines [GP0201] LMGP02010000 Phospholipids TLC (23); nano-ESI-MS (35) Root (fresh and whit ginseng) (23); Root, rhizome (fresh
                ginseng) (35)
39 Phosphatidylglyc (PG) cerol Glycerophospholipid [GP] ds Glycerophosphog-lycerols [GP04] – Diacylglycerophos-phoglycerols [GP0401] LMGP04010000 Phospholipids TLC (23); nano-ESI-MS (35) Root (fresh and whit ginseng) (23); Root, rhizome (fresh ginseng) (35)
40 Phosphatidylinos (PI) itol Glycerophospholipid [GP] ds Glycerophosphoin tols [GP06] nosi Diacylglycerophosph oinositols [GP0601] LMGP06010000 Phospholipids nano-ESI-MS (35) Root, rhizome (fresh ginseng) (35)
41 Cholesterol Sterol Lipids [ST] Sterols [ST01] Cholesterol and derivatives [ST0101] LMST01010001 Sterols TLC, GC-MS (44) Seed oil (44)
42 Campesterol Sterol Lipids [ST] Sterols [ST01] Ergosterols and C24- LMST01030097 Phytosterols TLC, GC-MS (45) Root (white ginseng
        methyl derivatives [ST0103]       (45)
43 Obtusifoliol Sterol Lipids [ST] Sterols [ST01] Ergosterols and C24- LMST01030101 4α-Methylsterols TLC, GC-MS (44) Seed oil (44)
        methyl derivatives [ST0103]        
44 β-Sitosterol Sterol Lipids [ST] Sterols [ST01] Stigmasterols and LMST01040250 Phytosterols TLC, GC-MS (45); ; Root (white ginseng
        C24-ethyl derivatives [ST0104]     GC-MS (24) (24)
45 Stigmasterol Sterol Lipids [ST] Sterols [ST01] Stigmasterols and LMST01040123 Phytosterols GC-MS (45) Root (white ginseng
        C24-ethyl derivatives [ST0104]       (45)
46 Isofucosterol Sterol Lipids [ST] Sterols [ST01] Stigmasterols and LMST01040145 Sterols TLC, GC-MS (44) Seed oil (44)
        C24-ethyl derivatives [ST0104]        
47 δ7-Avenasterol Sterol Lipids [ST] Sterols [ST01] Stigmasterols and LMST01040154 Sterols TLC, GC-MS (44) Seed oil (44)
        C24-ethyl derivatives [ST0104]        
48 Cycloartenol Sterol Lipids [ST] Sterols [ST01] Cycloartanols and LMST01100008 Triterpene alcoho ls TLC, GC-MS (44) Seed oil (44)
49 24-Methylene-cycloartanol Sterol Lipids [ST] Sterols [ST01] derivatives [ST0110] Cycloartanols and derivatives [ST0110] LMST01100001 Triterpene alcoho ls TLC, GC-MS (44) Seed oil (44)
50 Cycloeucalenol Sterol Lipids [ST] Sterols [ST01] Cycloartanols and derivatives [ST0110] LMST01100011 4α-Methylsterols TLC, GC-MS (44) Seed oil (44)
51 Myrcene Prenol Lipids [PR] Isoprenoids [PR01] C10 isoprenoids (monoterpenes) [PR0102] LMPR0102010005 5 Monoterpenes GC-MS (22) Root (white ginseng) (22)
52 Terpinolene Prenol Lipids [PR] Isoprenoids [PR01] C10 isoprenoids LMPR0102090062 2 Monoterpenes GC-MS (22) Root (white ginseng)
        (monoterpenes) [PR0102]       (22)
53 α-Pinene Prenol Lipids [PR] Isoprenoids [PR01] C10 isoprenoids LMPR0102120012 2 Monoterpenes GC-MS (22) Root (white ginseng)
        (monoterpenes) [PR0102]       (22)
54 β-Pinene Prenol Lipids [PR] Isoprenoids [PR01] C10 isoprenoids (monoterpenes) [PR0102] LMPR0102120013 3 Monoterpenes GC-MS (22) Root (white ginseng) (22)
55 Bicyclogermacre ene Prenol Lipids [PR] Isoprenoids [PR01] C15 isoprenoids (sesquiterpenes) [PR0103] LMPR0103100001 1 Sesquiterpenes GC-MS (22) Root (white ginseng) (22)
56 Humulene Prenol Lipids [PR] Isoprenoids [PR01] C15 isoprenoids (sesquiterpenes) [PR0103] LMPR0103110001 1 Sesquiterpenes GC-MS (22) Root (white ginseng) (22)
57 Nerolidol Prenol Lipids [PR] Isoprenoids [PR01] C15 isoprenoids (sesquiterpenes) [PR0103] LMPR0103010005 5 Sesquiterpenes GC-MS (22) Root (white ginseng) (22)
58 Zingiberene Prenol Lipids [PR] Isoprenoids [PR01] C15 isoprenoids (sesquiterpenes) [PR0103] LMPR0103060002 2 Sesquiterpenes GC-MS (22) Root (white ginseng) (22)
59 β-Bisabolene Prenol Lipids [PR] Isoprenoids [PR01] C15 isoprenoids (sesquiterpenes) [PR0103] LMPR0103060013 3 Sesquiterpenes GC-MS (22) Root (white ginseng) (22)
60 β-Caryophyllene e Prenol Lipids [PR] Isoprenoids [PR01] C15 isoprenoids (sesquiterpenes) [PR0103] LMPR0103120001 1 Sesquiterpenes GC-MS (22) Root (white ginseng) (22)
61 β-Selinene Prenol Lipids [PR] Isoprenoids [PR01] C15 isoprenoids (sesquiterpenes) [PR0103] LMPR0103190010 0 Sesquiterpenes GC-MS (22) Root (white ginseng) (22)
62 δ-Cadinene Prenol Lipids [PR] Isoprenoids [PR01] C15 isoprenoids (sesquiterpenes) [PR0103] LMPR0103330001 1 Sesquiterpenes GC-MS (22) Root (white ginseng) (22)
63 Squalene Prenol Lipids [PR] Isoprenoids [PR01] C30 isoprenoids (triterpenes) [PR0106] LMPR0106010002 2 Triterpenes TLC, GC-MS (44 4) Seed oil (44)
64 β-Amyrin Prenol Lipids [PR] Isoprenoids [PR01] C30 isoprenoids (triterpenes) [PR0106] LMPR0106150015 5 Triterpene alcohols TLC, GC-MS (44 4) Seed oil (44)
65 Lupeol Prenol Lipids [PR] Isoprenoids [PR01] C30 isoprenoids LMPR0106130001 1 Triterpene alcohols TLC, GC-MS (44) ) Seed oil (44)
        (triterpenes)        
        [PR0106]        
66 Catechin Polyketides [PK] Flavonoids [PK12] Flavans, Flavanols LMPK12020001 Phenolic acids UPLC-UV (48) Fruit, leaves, roots
        and       (48)
        Leucoanthocyanidi-        
        ns [PK1202]        
67 Formononetin Polyketides [PK] Flavonoids [PK12] Isoflavonoids LMPK12050037 Phenolic acids UPLC-UV (48) Fruit, leaves, roots
        [PK1205]       (48)
68 Kaempferol Polyketides [PK] Flavonoids [PK12] Flavones and LMPK12110003 Phenolic acids UPLC-UV (48) Fruit, leaves, roots
        Flavonols [PK1211]       (48)
69 Quercetin Polyketides [PK] Flavonoids [PK12] Flavones and LMPK12110004 Phenolic acids UPLC-UV [48 Fruit, leaves, roots
        Flavonols [PK1211]       (48)
70 Rutin Polyketides [PK] Flavonoids [PK12] Flavones and LMPK12112098 Phenolic acids UPLC-UV (48) Fruit, leaves, roots
        Flavonols [PK1211]       (48)
71 Hesperetin Polyketides [PK] Flavonoids [PK12] Flavanones [PK1214] LMPK12140003 Phenolic acids UPLC-UV (48) Fruit, leaves, roots
                (48)
72 Naringenin Polyketides [PK] Flavonoids [PK12] Flavanones [PK1214] LMPK12140001 Phenolic acids UPLC-UV (48) Fruit, leaves, roots
                (48)
73 Naringin Polyketides [PK] Flavonoids [PK12] Flavanones [PK1214] LMPK12140235 Phenolic acids UPLC-UV (48) Fruit, leaves, roots
                (48)
74 Resveratrol Polyketides [PK] Flavonoids [PK12] Diphenyl ethers, LMPK13090005 Phenolic acids UPLC-UV (48) Fruit, leaves, roots
        biphenyls, dibenzyls       (48)
        and stilbenes        
        [PK1309]        

a GC-FID, gas chromatography-flame ionization detection; HLPC-UV, high-performance liquid chromatography-ultra violet detector; HR-EIMS, high resolution-electron impact mass spectrometry; IR, infrared spectroscopy; GC-MS, gas chromatography-mass spectrometry; GLC-FID, gas liquid chromatography-flame ionization detection; NMR, nuclear magnetic resonance spectroscopy; TLC, thin layer chromatograph

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