Table 4. Identified compounds in GMMG fraction through LCMS analysis

No Name Formula m/z Mass Group Activity Related compound(s) Activity
1 4-(2-hydroxypropoxy)-3,5-dimethyl-phenol C11H16 O3 197.12 196.11 Alcohol • No record
2 Dioscoretine C13 H23NO3 242.17 241.17 Fatty acid • No record
3 2-Phenylethyl 3-methylbutanoate C13 H18O2 207.14 206.13 Carboxylic acid • No record
4 ML-236C C18H26O3 291.20 290.19 Carbobicylic compound • Anticholesteremic (Endo et al., 1976)
5 C16 Sphinganine C16H35NO2 274.27 273.27 Lipid: Phospholipid • Antibacteria (Reid et al., 2019)
• Anticancer (Bagheri et al., 2018)
6 2,6-Nonadien-1-ol C9H16O 158.15 140.12 Fatty alcohol • Flavour compound (Kemp et al., 1974; Flath et al., 1983; McGinty et al., 2010; Api et al., 2015, 2019)
7 (–)-trans-C75 C14H22O4 272.19 254.15 Carboxylic acid • No record
8 Cyrneine A* C20H28O3 317.21 316.20 Terpene: Diterpene • Neurite outgrowth (Marcotullio et al., 2006; Obara et al., 2007) Cyathane diterpene group • Anti-oxidant (Marcotullio et al., 2008)
• Anti-nitric oxide (Wang et al., 2014)
• Neurite outgrowth (Cao et al., 2018)
• Anti-bacterial (Nitthithanasilp et al., 2018)
9 7beta-Hydroxy-lathyrol C20H30O4 335.22 334.21 Lipid: Diterpene • No record
10 Graveolinine* C17H13NO3 297.12 279.09 Quinonline Anti-angiogenesis (An et al., 2010)
Anti-tumor and anti-platelet aggregation (Wu et al., 2003)
Anti-AChE and anti-β amyloid (Luo et al., 2020)
11 3α-Hydroxy-4,4-bisnor-8,11,13-podocarpatriene C15H20O 217.16 216.15 Phenol • No record
12 Militarinone A* C26H37NO6 460.27 459.26 Pyridine alkaloid • Neurite outgrowth (Schmidt et al., 2002; Riese et al., 2004; Küenzi et al., 2008) 4-hydroxy-2-pyridone • Neurite outgrowth (Schröder et al., 2015)
(+)-N-Deoxymilitarinone A • Neurite outgrowth (Cheng et al., 2006)
13 Eplerenone* C24H30O6 432.24 414.21 Lactone • Anti-inflammation (Suzuki et al., 2006; Xiao et al., 2009; Bayorh et al., 2012; Chen et al., 2013, 2018; Łabuzek et al., 2014; Wada et al., 2017; Vecchiola et al., 2020)
• Neuroprotective (Dong et al., 2012; Wang et al., 2020)
14 Curcumenol* C15H22O2 235.17 234.16 Curcumin • Anti-neuroinflammation (Tanaka et al., 2008; Lo et al., 2015; Hsiao et al., 2020; Pintatum et al., 2020) Oxycurcuminol • Anti-stroke (Chen et al., 2018)
• Antioxidant
• Neuroprotective (Hamdi et al., 2015)
15 (+–)-Trihydroxy-decipiadiene C20H32O3 321.24 320.23 Lipid: Isoprenoid • No record
16 alhpa-Tocopheronolactone C16H22O4 301.14 278.15 Lipid: Isoprenoid • No record
17 N-cis-Tetradec-9Z-enoyl-L-Homoserine lactone C18H31NO3 310.24 309.23 Lactone • No record
18 Stigmatellin Y C29H40O6 502.32 484.28 Phenol • No record
19 Anandamide (20:l, n-9) C22H43NO2 376.32 353.33 Fatty amide • No record
20 2-Amino-14,16-dimethyloctadecan-3-ol C20H43NO 336.32 313.33 Amino alcohol • No record
21 2-Ethyl-dodecanoic acid C14H28O2 229.22 228.21 Fatty acid • No record
22 (–)-Isoamijiol C20H32O2 322.27 304.24 Lipid: Isoprenoid • No record
23 Palmitic amide C16H33NO 256.26 255.26 Fatty amide • No record
24 Coproporphyrin IV C36H38N4O8 655.28 654.27 Porphyrin • No record
25 Cassaidine C24H41NO4 408.31 407.30 Tricylic diterpenoids • No record
26 Haplophytine C37H40N4O7 653.30 652.29 Indole alkaloid • No record
27 24,25-Epoxy-cholesterol C27H44O2 401.34 400.33 Desmosterol • No record
28 MGDG(18:1(9Z)/18:1(9Z)) C45H82O10 805.58 782.59 Glycosyldiradylglycerols • No record
Compound marked with asterisk symbol indicates compound with previously identified neuroprotective properties.
GMMG, fraction G; LCMS, liquid chromatography-mass spectrometry; AChE, acetylcholinesterase.