Research Progress of Ferula ferulaeoides: A Review
Abstract
:1. Introduction
2. Chemical Constituents of F. ferulaeoides
3. Pharmacological Effects of F. ferulaeoides
3.1. Antimicrobial Activity
3.2. Antitumor Effect
3.3. Anti-Inflammatory Effect
3.4. Insecticidal Activity
3.5. Toxic Effect
4. Research on Quality Control
4.1. Traits and Microstructure
4.2. Studies on Fingerprint
4.3. Content Determination
5. Prospect: Application of F. ferulaeoides in Food Industry
6. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Type | No. | Compound | Formula | Molecular Weight | References |
---|---|---|---|---|---|
Sesquiterpene–coumarins | 1 | Badrakemin | C24H30O4 | 382 | [13] |
2 | Badrakemin acetate | C26H32O5 | 424 | [13] | |
3 | Conferol acetates | C26H32O5 | 424 | [13] | |
4 | Ferulin A | C25H33O5 | 413 | [14] | |
5 | Ferulin B | C24H32O5 | 400 | [15] | |
6 | Ferulin C | C25H34O5 | 414 | [14] | |
7 | 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-3-[4,8-dimethyl-3(E),7-nonadienyl]-furo [3,2-c] coumarin | C24H30O4 | 382 | [14] | |
8 | 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-3-[4,8-dimethyl-3(E),7-nonadienyl]-furo [3,2-c] coumarin | C24H30O4 | 382 | [14,16] | |
9 | 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-3-[4-methyl-5-(4-methyl-2-furyl)-3(E)-pentenyl]-furo [3,2-c] coumarin | C24H26O5 | 394 | [14] | |
10 | 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-3-[4,8-dimethyl-3(E),7-nonadienyl]-furo [3,2-c] coumarin | C25H32O4 | 396 | [15] | |
11 | 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo [3,2-c] coumarin | C24H30O4 | 382 | [15] | |
12 | 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo [3,2-c] coumarin | C24H30O4 | 382 | [15] | |
13 | 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo [3,2-c] coumarin | C25H32O4 | 396 | [15] | |
14 | 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E)-pentenyl]-furo [3,2-c] coumarin | C24H26O5 | 394 | [14] | |
15 | 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E)-pentenyl]-furo [3,2-c] coumarin | C24H26O5 | 394 | [14] | |
16 | 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo [3,2-c] coumarin | C25H32O4 | 396 | [15] | |
17 | 2,3-dihydro-7-methoxy-2R*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo [3,2-c] coumarin | C25H32O4 | 396 | [15] | |
18 | 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo [3,2-c] coumarin | C25H30O5 | 410 | [15] | |
19 | 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E)-pentenyl]-furo [3,2-c] coumarin | C25H28O5 | 408 | [15] | |
20 | (trans)-2,3-dimethyl-3-[9-hydroxymethyl-4-methyl-3E,7Z-nonadienyl]-7-hydroxy-2(3H)-furo [3,2-c] coumarin | C24H31O5 | 399 | [15] | |
21 | 7-hydroxy-2-[1-hydroxy-1,5,9-trimethyl-4E,8-decadienyl]-2(3H)-furo [3,2-c] coumarin | C24H31O5 | 399 | [15] | |
22 | 2-[1-hydroxy-1,5,9-trimethyl-4E,8-decadienyl]-7-methoxy-2(3H)-furo [3,2-c] coumarin | C25H33O5 | 408 | [15] | |
23 | 4,7-dihydroxy-3-[3,7,11-trimethyl-2(E),6(E),10-dodecatrienyl] coumarin | C24H30O4 | 382 | [14] | |
Sesquiterpene–heteroketone compounds | 24 | Ferulin D | C25H32O4 | 396 | [15] |
25 | Ferulin E | C24H31O4 | 383 | [14] | |
26 | 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo [3,2-b] chromone | C24H30O4 | 382 | [14] | |
27 | 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E),7-pentenyl]-furo [2,3-b] chromone | C24H26O5 | 394 | [15] | |
28 | 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E),7-pentenyl]-furo [2,3-b] chromone | C24H26O5 | 394 | [15] | |
29 | 4-hydro-7-hydroxy-2-methyl-2-[4,8-dimethyl-3E,7-nonadienyl]-2(3H)-pyro [2,3-b] chromone | C24H31O4 | 383 | [14] | |
30 | 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo [3,2-b] chromone | C24H30O4 | 382 | [15] | |
31 | 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo[3,2-b] chromone | C24H30O4 | 382 | [15] | |
Sesquiterpene–phenolic compounds | 32 | Dshamirone (secoammoresinol) | C23H33O3 | 356 | [15] |
33 | (4E,8E)-1-(2,4-dihydroxyphenyl)-5,9,13-trimethyl-tetradeca-4,8,12-trien-1-one | C23H32O3 | 356 | [14] | |
34 | (4E,8E)-1-(2,4-dihydroxyphenyl)-2-methoxycar-bonyl-5,9,13-trimethyltetradeca-4,8,12-trien-1-one | C25H34O5 | 414 | [14] | |
35 | 1-(2,4-dihydroxyphenyl)-3,7,11-trimethyl-3-vinyl-6(E),10-dodecadiene-1-one | C23H32O3 | 356 | [15] | |
36 | 8,9-oxoisopropanyldshami-rone | C22H30O5 | 374 | [17] | |
37 | Ferulaeolactone A | C24H34O6 | 418 | [17] | |
38 | 8-acetoxy-9-hydroxydshmirone | C24H34O5 | 402 | [17] | |
39 | Ferulaeone A | C25H33O5 | 413 | [15] | |
40 | Ferulaeone B | C25H37O6 | 433 | [15] | |
41 | Ferulaeone C | C23H31O3 | 355 | [15] | |
42 | Ferulaeone D | C23H28O4 | 369 | [15] | |
43 | Ferulaeone E | C33H49O4 | 509 | [15] | |
44 | Ferulaeone F | C33H49O4 | 509 | [15] | |
45 | Ferulaeone G | C33H43O5 | 519 | [15] | |
46 | Ferulaeone H | C38H55O5 | 591 | [15] | |
47 | 3-(2,4-dihydroxybenzoyl)-4S*,5R*-dimethyl-5-[4,8-dimethyl-3(E),7(E)-nonadien-1-yl] tetrahydro-2-furanone | C24H32O5 | 400 | [15] | |
48 | 3-(2-hydroxyl-4-methoxybenzoyl)-4S*,5R*-dimethyl-5-[4,8-dimethyl-3(E),7(E)-nonadien-1-yl] tetrahydro-2-furanone | C25H34O5 | 414 | [15] | |
49 | 3-(2,4-dihydroxybenzoyl)-4R*,5R*-dimethyl-5-[4,8-dimethyl-3(E),7(E)-nonadien-1-yl] tetra-hydro-2-furanone | C24H32O5 | 400 | [15] | |
50 | Ferulactone A | C24H32O9 | 463 | [18] | |
51 | Ferulactone B | C24H30O7 | 429 | [18] | |
52 | 3S*-(2,4-dihydroxybenzoyl)-4R*,5R*-dimethyl-5-(4,8-dimethyl-3(E),7(E)-nonadien-1-yl) tetrahydro-2-furanone | C24H32O5 | 400 | [19] | |
53 | 1-(2,4-dihydroxyphenyl)-2-hydroxy-5,9,13-trimethy1-4(E),8(E),12-tetradecatrien-1-one | C23H32O4 | 372 | [19] | |
54 | 1-(2,4-dihydroxyphenyl)-3,7,11-trimethyl-3-vinyl-6(E),10-dodecadiene-1,9-dione | C23H30O4 | 370 | [19] | |
55 | 1-(2,4-dihydroxyphenyl)-3,7-dimethyl-3-vinyl-8-(4-methyl-2-furyl)-6(E)-octen-l-one | C23H28O4 | 368 | [15] | |
56 | 3S*-(2,4-dihydroxybenzoyl)-4R*,5R*-dimethyl-5-[4-methyl-5-(4-methyl-2-furyl)-3(E)-penten-1-yl] tetrahydro-2-furanone | C24H28O6 | 412 | [15] | |
57 | 3S*-(2,4-dihydroxybenzoyl)-4R*,5S*-dimethyl-5-[4-methyl-5-(4-methyl-2-furyl)-3(E)-penten-l-yl] tetrahydro-2-furanone | C24H28O6 | 421 | [15] |
Type | Compound | References |
---|---|---|
Monoterpenoids | α-pinene, β-pinene, camphene, δ-3-carene, limonene, D-limonene, L-limonene, α-phellandrene, β-thujene, γ-terpinene, ocimene, β-ocimene, terpinolene, α-terpinolene, myrcene, β-myrcene, sabinene, fenchene, fenchol, borneol, (R)-camphor, citronellol, P-cymen-8-ol, α-terpined, 1,7,7-trimethyl-exo-bicyclo[2.2.1]heptan-2-ol, tanacetone, Z-3-pnen-2-ol, isogeraniol), 3-methoxy-p-cymene, dihydrocarvyl aetate, thymylether methyl, 2-camphanol acetate, exobornyl acetate, α-fenchyl acetate, [1,3,6-octatriene,3,7-dimethyl-,(Z)-], 3-isopropylidene-5-methyl-hex-4-en-2-one) | [8] |
Sesquiterpene | Farnesene, α-guaiene, α-farnesene, β-farnesene, α-curcumene, β-curcumene, α-elemene, β-elemene, valencene, (−)-alloaromadendrene, trans-caryophyllene, aristolene, α-gurjunene, α-cedrene, β-cedrene, hujopsenet, α-himachalene, β-himachalene, α-bulnesene, isoledene, (Z,E)-α-farnesene, 1.2,3,4,4A,5,6,8A-octa-hydro-naphthalene, bergamotene, γ-selinene, α-bergamotene, zingiberene, isocaryophyllene, ledene, β-bisabolene, τ-guaiene, guaiol, α-guaiol, δ-guaiol, bulnesol, 10-O-γ-eudesmol, α-eudesmol, τ-eudesmol, β-eudesmol, elemiol, cedrol, hinesol, agarospirol, ginsenol, calareneexoide, eudesm-7(11)-en-4-ol, β-bisabolol, nerolidol, trans-nerolidol, 1,2- propanediol,3-methoxy-, 2,6,6-trimethyl-1- methylen-cyclohex-2-ene, 5,9-undecadien- 2-one,6,10-dimethyl-,(Z)-, 1,1-dimethyl-2,4-di(1-propenyl)cyclohexane, (Z)-2,6,10- trimethyl-1,5,9-undecatriee, 5-β-H,7-β, 10-α-selina-4(19),11-diethy, 4-(1E)-1,3-butadien-1-yl-3,5,5-trimethyl] | [8] |
Aromatic | Toluene, resorcinol, O-cymene, benzene, 2-methoxy-4-vinylphenol, 1-methyl-4-(1-methylethyl) benzene, 4-(1-methylethyl)-benzene-methanol, 1-1,5-dimethyl-4- hexenyl-4-methyl benzene | [8] |
Alcohol esters | cyclopentanol,2-methyl acetate, neryl acetate, butane-2,3-diol, (2S,3S)-(+)-2,3-butane diol, 4,8-dimethyl-3,7-nonadien-2-ol, 4-terpinyl acetate, α-terpinyl acetate, ethyl palmitate, ethyl linoleate | [8] |
Type | No. | Compound | Formula | Molecular Weight | References |
---|---|---|---|---|---|
Phenylpropanoids | 1 | myristicin | C11H12O3 | 192 | [19] |
Phenols, phenolic acids | 2 | 2,4-dihydroxyacetophenone | C8H8O3 | 152 | [19] |
3 | 2-hydroxy-4-methoxyacetophenone | C9H10O3 | 166 | [19] | |
4 | 2,4-dihydroxybenzoic acid | C7H6O4 | 154 | [19] | |
5 | 2,4-dihydroxy-α-oxobenzeneacetic acid | C8H8O4 | 168 | [19] | |
6 | β-resorcylic acid | C7H6O4 | 154 | [19] | |
7 | Methoxyresorcylic acid | C8H8O4 | 168 | [19] | |
8 | Umbelliferone | C9H6O3 | 162 | [6] | |
9 | Lehmannmlone | C24H30O4 | 382 | [6] | |
10 | methyl 2,4-dihydroxybenzoate | C8H8O4 | 168 | [6] | |
11 | ethyl 2,4-dihydroxybenzoate | C9H10O4 | 182 | [6] | |
Steroids | 12 | β-sitosterol | C29H50O | 414 | [19] |
13 | Daucossterol | C35H60O6 | 576 | [6] |
Ferula Plants | Antibacterial Ingredients | Microorganism | References |
---|---|---|---|
F. lycia | essential oil | Haemophilus influenza T | [23] |
F. glauca | essential oil | Streptococcus mutans, Enterococcus faecalis, Escherichia coli | [23] |
F. heuffelii | essential oil | Micrococcus luteus, Staphylococcus epidermidis, B. subtilis,Micrococcus flavus | [23] |
F. assafoetida | organic extractswater extracts | coli, S. aureus, E. faecalis, Shigella flexneri, Klebsiella pneumonia | [21,23] |
F. gummosa | oleo-resin | E. coli, P. aeruginosa, S. aureus, Salmonella enteritidis, Listeria monocytogenes | [23] |
essential oil | C. albicans, S. epidermidis, S. aureus, E. coli, B. cereus, E. faecalis, P. aeruginosa | ||
F. communis | petroleum ether extract | S. aureus, B. subtilis, Streptococcus durans, E. faecalis | [23] |
F. szovitsiana | essential oil | B. subtilis | [23] |
F. hermonis | essential oil | S. typhi, P. aeruginosa, E. coli, S. aureus, S. fecalis | [23] |
F. vesceritensis | essential oil | E. coli, K. pneumonia, S. aureus, P. aeruginosa | [23] |
F. kuhistanica | essential oil | S. aureus | [23] |
F. ferulaeoides | sesquiterpene derivatives | Drug-resistant S. aureus | [14] [22] |
alcohol extract | S. aureus, B. subtilis, Sarcina | ||
F. elaeochytris | essential oil | S. aureus | [24] |
F.pseudalliacea | sesquiterpene coumarins | S. aureus, Enterococcus faecium, B. cereus, E. coli, P. aeruginosa | [23] |
F. tunetana | essential oil | Salmonella typhimurium, S. epidermidis, Micrococcus luteus, B. Cereus, B. subtilis | [25] |
F. tingitana L. | essential oil | Bacillus subtilis, Neisseria gonorrhoeae | [26] |
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Chen, Z.; Zhou, G.; Ma, S. Research Progress of Ferula ferulaeoides: A Review. Molecules 2023, 28, 3579. https://doi.org/10.3390/molecules28083579
Chen Z, Zhou G, Ma S. Research Progress of Ferula ferulaeoides: A Review. Molecules. 2023; 28(8):3579. https://doi.org/10.3390/molecules28083579
Chicago/Turabian StyleChen, Zhengqiong, Gang Zhou, and Shengjun Ma. 2023. "Research Progress of Ferula ferulaeoides: A Review" Molecules 28, no. 8: 3579. https://doi.org/10.3390/molecules28083579