sorgoleone: Sorgoleone refers to a group of benzoquinones from Sorghum bicolor having 2-hydroxy and 5-methoxy substitutions and either a 15- or 17-carbon chain with one, two, or three double bonds at position 3; The name sorgoleone was first given to 5-methoxy-3-(8'Z,11'Z)-pentadeca-8'11'14'-trienylbenzene-1,2,4-triol but this is unstable and is easily oxidized to the quinone, sorgoleone-358, which is the major constituent of the root exudate; binds at PLASTOQUINONE site of PSII [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
sorgoleone : A member of the family of benzoquinones, sorgoleone is 2-hydroxy-5-methoxy-1,4-benzoquinone in which the hydrogen at position 3 is substituted by a (4Z,7Z)-pentadeca-1,4,7-trien-15-yl group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Sorghum | genus | A plant genus of the family POACEAE. The grain is used for FOOD and for ANIMAL FEED. This should not be confused with KAFFIR LIME or with KEFIR milk product.[MeSH] | Poaceae | A large family of narrow-leaved herbaceous grasses of the order Cyperales, subclass Commelinidae, class Liliopsida (monocotyledons). Food grains (EDIBLE GRAIN) come from members of this family. RHINITIS, ALLERGIC, SEASONAL can be induced by POLLEN of many of the grasses.[MeSH] |
| Sorghum bicolor | species | [no description available] | Poaceae | A large family of narrow-leaved herbaceous grasses of the order Cyperales, subclass Commelinidae, class Liliopsida (monocotyledons). Food grains (EDIBLE GRAIN) come from members of this family. RHINITIS, ALLERGIC, SEASONAL can be induced by POLLEN of many of the grasses.[MeSH] |
| ID Source | ID |
|---|---|
| PubMed CID | 6475682 |
| CHEMBL ID | 463021 |
| CHEBI ID | 61117 |
| SCHEMBL ID | 16174036 |
| MeSH ID | M0293602 |
| Synonym |
|---|
| 2-hydroxy-5-methoxy-3-[(8z,11z)-pentadeca-8,11,14-trien-1-yl]cyclohexa-2,5-diene-1,4-dione |
| 2-hydroxy-5-methoxy-3-(8'z,11'z)-pentadeca-8',11',14'-trienyl-p-benzoquinone |
| 2-hydroxy-5-methoxy-3-(8'z,11'z)-pentadeca-8',11',14'-trienyl-1,4-benzoquinone |
| 2-hydroxy-5-methoxy-3-[(z,z)-8',11',14'- pentadecatriene]-p-benzoquinone |
| sorgoleone |
| CHEMBL463021 |
| chebi:61117 , |
| 2-hydroxy-5-methoxy-3-[(8z,11z)-pentadeca-8,11,14-trienyl]cyclohexa-2,5-diene-1,4-dione |
| SCHEMBL16174036 |
| 2-hydroxy-5-methoxy-3-(8z,11z,14z-pentadecatrien-1-yl)-1,4-benzoquinone |
| LMPK15050001 |
| Q27130824 |
Sorgoleone-358 is an important allelochemical of the oily droplets exuded from root hairs of various species in the Sorghum genus. It is a highly hydrophobic compound, presenting a log Kow of 6.1.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Sorgoleone-358 is an important allelochemical of the oily droplets exuded from root hairs of various species in the Sorghum genus. " | ( Conservation and divergence in sorgoleone production of sorghum species. Besançon, TE; Dayan, FE; Everman, WJ; Gannon, TW, 2020) | 2.29 |
| "Sorgoleone is a major component of the hydrophobic root exudate of Sorghum bicolor and is of particular interest to plant chemical ecology as well as agriculture. " | ( Effects of auxins on sorgoleone accumulation and genes for sorgoleone biosynthesis in sorghum roots. Kim, YK; Park, SU; Park, WT; Pyon, JY; Uddin, MR, 2011) | 2.13 |
| "Sorgoleone is a highly hydrophobic compound, presenting a log Kow of 6.1." | ( Sorptive behavior of sorgoleone in ultisol in two solvent systems and determination of its lipophilicity. Dick, DP; Kruse, ND; Peralba, MC; Trezzi, MM; Vidal, RA, 2006) | 1.37 |
| Class | Description |
|---|---|
| monohydroxy-1,4-benzoquinones | Any 1,4-benzoquinone carrying a single hydroxy substituent. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Photosystem II protein D1 | Spinacia oleracea (spinach) | IC50 (µMol) | 0.0650 | 0.0650 | 0.4849 | 1.9000 | AID1102575 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1081439 | Phytotoxic activity against Agrostis stolonifera var. Penncross seedlings assessed as growth inhibition at 1 mM | 2010 | Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7 | Phytotoxic activity of quinones and resorcinolic lipid derivatives. |
| AID401435 | Phytotoxicity against lettuce seedlings assessed as inhibition of seed germination at 0.1 mM after 4 days | 1998 | Journal of natural products, Jul, Volume: 61, Issue:7 | A new photosystem II electron transfer inhibitor from Sorghum bicolor. |
| AID1081437 | Phytotoxic activity against Lactuca sativa cv. Iceberg A (lettuce) seedlings assessed as growth inhibition at 0.03 mM | 2010 | Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7 | Phytotoxic activity of quinones and resorcinolic lipid derivatives. |
| AID401437 | Inhibition of photosystem 2 in spinach thylakoid membranes assessed as oxygen evolution | 1998 | Journal of natural products, Jul, Volume: 61, Issue:7 | A new photosystem II electron transfer inhibitor from Sorghum bicolor. |
| AID401438 | Reduction in light-induced chlorophyll fluorescence half-life in spinach thylakoids membrane at 0.3 to 1 uM | 1998 | Journal of natural products, Jul, Volume: 61, Issue:7 | A new photosystem II electron transfer inhibitor from Sorghum bicolor. |
| AID334171 | Inhibition of Photosystem 2 in spinach thylakoid membrane assessed as inhibition of photosynthetic oxygen evolution | 2003 | Journal of natural products, Jan, Volume: 66, Issue:1 | PSII inhibitory activity of resorcinolic lipids from Sorghum bicolor. |
| AID1081441 | Phytotoxic activity against Agrostis stolonifera var. Penncross seedlings assessed as growth inhibition at 0.1 mM | 2010 | Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7 | Phytotoxic activity of quinones and resorcinolic lipid derivatives. |
| AID1081433 | Phytotoxic activity against Agrostis stolonifera var. Penncross seedlings assessed as growth inhibition at 0.01 mM | 2010 | Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7 | Phytotoxic activity of quinones and resorcinolic lipid derivatives. |
| AID1102575 | Inhibition of photosystem II mediated oxygen evolution in Spinacia oleracea (spinach) thylakoid measured for 25 sec | 2003 | Journal of agricultural and food chemistry, Dec-17, Volume: 51, Issue:26 | Chromatographic separation and in vitro activity of sorgoleone congeners from the roots of sorghum bicolor. |
| AID1081440 | Phytotoxic activity against Agrostis stolonifera var. Penncross seedlings assessed as growth inhibition at 0.3 mM | 2010 | Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7 | Phytotoxic activity of quinones and resorcinolic lipid derivatives. |
| AID401436 | Phytotoxicity against lettuce seedlings assessed as inhibition of seed germination at >0.3 mM after 4 days | 1998 | Journal of natural products, Jul, Volume: 61, Issue:7 | A new photosystem II electron transfer inhibitor from Sorghum bicolor. |
| AID1081438 | Phytotoxic activity against Lactuca sativa cv. Iceberg A (lettuce) seedlings assessed as growth inhibition at 0.01 mM | 2010 | Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7 | Phytotoxic activity of quinones and resorcinolic lipid derivatives. |
| AID334169 | Phytotoxicity against Lactuca sativa assessed as inhibition of seedlings germination at 3.33 mM after 4 days | 2003 | Journal of natural products, Jan, Volume: 66, Issue:1 | PSII inhibitory activity of resorcinolic lipids from Sorghum bicolor. |
| AID1081432 | Phytotoxic activity against Agrostis stolonifera var. Penncross seedlings assessed as growth inhibition at 0.03 mM | 2010 | Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7 | Phytotoxic activity of quinones and resorcinolic lipid derivatives. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 1 (3.33) | 18.2507 |
| 2000's | 14 (46.67) | 29.6817 |
| 2010's | 10 (33.33) | 24.3611 |
| 2020's | 5 (16.67) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (33.51) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (3.33%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 29 (96.67%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||