General Information of Natural Product (ID: NP0354)
  Natural Product Name
Linoleic Acid
  Synonyms
linoleic acid; 60-33-3; Linolic acid; (9Z,12Z)-octadeca-9,12-dienoic acid; Telfairic acid; cis,cis-Linoleic acid; Linoleate; Grape seed oil; cis,cis-9,12-Octadecadienoic acid; 9,12-Linoleic acid; Emersol 315; Unifac 6550; cis-9,cis-12-Octadecadienoic acid; 9Z,12Z-Linoleic acid; Polylin 515; (Z,Z)-9,12-Octadecadienoic acid; 9Z,12Z-octadecadienoic acid; Extra Linoleic 90; 9-cis,12-cis-Linoleic acid; Emersol 310; all-cis-9,12-Octadecadienoic acid; Polylin No. 515; 9,12-Octadecadienoic acid (9Z,12Z)-; Linoleic; acide linoleique; 9,12-Octadecadienoic acid; Linoleic acid, pure; alpha-Linoleic acid; 9,12-Octadecadienoic acid (Z,Z)-; acido linoleico; Leinoleic acid; (9Z,12Z)-Octadecadienoic acid; UNII-9KJL21T0QJ; 9-cis,12-cis-Octadecadienoic acid; 8024-22-4; acide cis-linoleique; 9,12-Octadecadienoic acid, (Z,Z)-; (9Z,12Z)-9,12-octadecadienoic acid; CHEBI:17351; cis-9, cis-12-octadecadienoic acid; cis-Delta(9,12)-octadecadienoic acid; 9KJL21T0QJ; CHEMBL267476; 9-cis,12-cis-Octadecadienoate; C18:2; Oils, grape; MFCD00064241; NSC-281243; cis,cis-linoleate; NCGC00091049-04; VESPULA PENSYLVANICA B708568K063; DSSTox_CID_5505; DSSTox_RID_77814; DSSTox_GSID_25505; Oils, grape seed; CAS-60-33-3; CCRIS 650; 14C-Linoleic acid; HSDB 5200; (14C)-Linoleic acid; SR-01000944790; cis-delta9,12-Octadecadienoic acid; UNII-7552P0K6PN; EINECS 200-470-9; NSC 281243; (14C)alpha-Linolenic acid; acidelinoleique; 7552P0K6PN; Linolate; grapeseed oil; linoleic-acid; Leinolic acid; AI3-11132; Ronacare asc 3; trans-9,trans-12-Octadecadienoic acid; 9,12-Octadecadienoic acid, (9E,12E)-; 9Z,12Z-Linoleate; Linoleic Acid 315; n-6,9 all-cis; Linoleic acid, 95%; 9Z,12Z-Octadecadienoate; 9-cis,12-cis-Linoleate; Linoleic acid, >=95%; Linoleic acid, >=99%; bmse000497; bmse000604; Epitope ID:117705; linoleic and linolenic acids; SCHEMBL7067; cis,12-Octadecadienoic acid; Pamolyn 125 (Salt/Mix); cis-D9,12-Octadecadienoate; BSPBio_001374; CCRIS 652; all-cis-9,12-Octadecadienoate; BML3-C03; cis-9,cis-12-Octadecadienoate; GTPL1052; Linoleic acid, >=95%, FG; Linoleic acid, puriss., 90%; delta9,12-Octadecadienoic acid; (Z,Z)-9,12-Octadecadienoate; DTXSID2025505; ACon1_000270; BDBM22231; C18:2, n-6,9 all-cis; cis-D9,12-Octadecadienoic acid; Linoleic acid, >=93% (GC); CHEBI:137735; 9,12-Octadecadienoic acid, (Z,Z)-, labeled with carbon-14; HMS1361E16; HMS1791E16; HMS1989E16; HMS3402E16; HMS3649F07; HMS3886F05; Linoleic acid, analytical standard; 9,12-Octadecadienoic acid (VAN); HY-N0729; ZINC4474613; 9,12-Octadecadienoic acid, (Z)-; Tox21_111067; Tox21_202171; Tox21_303080; (9Z,12Z)-9,12-Octadecadienoate; C18:2 9c; cis,cis-octadeca-9,12-dienoic acid; cis-9,cis-12-Octadecadienoic acid,; LMFA01030120; NSC281243; s5821; (Z,Z)-Octadeca-9, 12-dienoic acid; 9,12-Octadecadienoic acid, (E,E)-; 9,12-Octadecadienoic acid, cis,cis-; AKOS015951293; ACN-045515; DB14104; rans, trans-9,12-octadecadienoic acid; 9-(Z), 12-(Z)-Octadecadienoic acid; cis-.DELTA.9,12-Octadecadienoic acid; IDI1_033844; NCGC00091049-01; NCGC00091049-02; NCGC00091049-03; NCGC00091049-05; NCGC00091049-06; NCGC00091049-07; NCGC00257024-01; NCGC00259720-01; 12c omega6 todos cis-9,12-octadienoico; 80969-37-5; AC-33770; AS-12672; C18:2 (n-6); FEMA NO. 3380, LINOLEIC ACID-; Linoleic acid, technical, 60-74% (GC); Octadeca-9,12-dienoic acid, (cis,cis)-; AI3-36448; 9,Z)-; CS-0009742; L0053; L0124; C01595; 9, (Z)-; A832696; Q407426; SR-01000944790-1; SR-01000944790-3; BRD-K08973992-001-03-9; C18:2 9c, 12c omega6 todos cis-9,12-octadienoico; 5CE5E1F3-8859-4C5B-9AFE-E44A7076DF6E; UNII-0JXR8F0V1Q component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-116Z6MZN1M component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-44NH37HHP9 component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-5U9XZ261ER component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-96GS7P39SN component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-9B22238JYI component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-B6G0Y5Z616 component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-F85N2YHE4E component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-HBA528N3PW component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-ODL221H4AM component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-V1PY73ZXPE component OYHQOLUKZRVURQ-HZJYTTRNSA-N; Linoleic acid, liquid, BioReagent, suitable for cell culture; UNII-79P21R4317 component OYHQOLUKZRVURQ-HZJYTTRNSA-N; Linoleic acid, 2.0 mg/mL in ethanol, certified reference material; cis,cis-9,12-octadecadienoic acid; LINOLEATE; emersol315; Linoleic; unifac6550;; 8016-21-5; Linoleic acid, PharmaGrade, Manufactured under appropriate controls for use as a raw material in pharma or biopharmaceutical production
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  Formula C18H32O2
  Weight 280.4
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
  InChI Key OYHQOLUKZRVURQ-HZJYTTRNSA-N
  Isomeric SMILES CCCCC/C=C\\C/C=C\\CCCCCCCC(=O)O
  Canonical SMILES CCCCCC=CCC=CCCCCCCCC(=O)O
  External Links PubChem ID 5280450
CAS ID 60-33-3
NPASS ID NPC85813
HIT ID C0189
CHEMBL ID CHEMBL267476
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Aquilaria agallocha
  Factor Name: Plant Pathogen Infection [1]
              Species Info Factor Info
               Experiment Detail
Artificial inoculation of fungal isolates: The most frequently isolated fungi from infected agarwood (e.g. Chaetomium globosum and Fusarium oxysporum) were inoculated to the healthy plants by artifi cial boring on to the plants. Inoculation was made with two different fungi alone and in their combination. Observations were made at an interval of 30 days after inoculation.
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               Factor Function
This investigation showed a marked difference in the oil compositions among the treatments with regards to their quality. Valerianol (3.0%) and tetradec-anioc acid (7.1%) contents were recorded higher in the oils of naturally infected plants than in that of healthy ones (0.1% and 6.9%, respectively). Pentadecenoic acid was totally absent in the oils of healthy, whereas it was found in a greater amount (6.8%) in the oil of naturally infected plants. In contrast, dodecanoic acid (3.1%), pentadecanoic acid (6.2%), hexadecanoic acid (31.5%) and octadecanoic acid (4.1%) were found in a higher amount in the oils of healthy plants, while the oils obtained from naturally infected plants contained lower amounts of these components (2.5%, 4.8%, 20.0% and 1.0%, respectively). The oils obtained from the inoculated plants showed almost similar distribution of the components with healthy plants.
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               Factor Part Location NP Content
 
Healthy plants
Wood chips India
NP Content: 3.4 %
 
Artificial inoculation plants (Chaetomium globosum)
Wood chips India
NP Content: 3.1 %
 
Artificial inoculation plants (Fusarium oxysporum)
Wood chips India
NP Content: 3 %
 
Artificial inoculation plants (C. globosum and F. oxysporum)
Wood chips India
NP Content: 3.4 %
      Species Name: Blumea balsamifera (L.) DC.
  Factor Name: Month Variation; Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
The experiments were performed in the experimental field of the Tropical Crops Genetic Resources Institute, Chinese Academy of Tropical Agricultural Sciences (Danzhou, Hainan, China; localization 19.52° N, 109.50° E; altitude 118 m; annual average precipitation 1815 mm; annual average temperature 23.5 ℃ ;the soil characteristics are : "Organic matter (g/kg) 11.37;pH 4.94;N (g/kg) 0.51;P (mg/kg) 25.33;K (mg/kg) 33.89). The experimental B. balsamifera plants were one-year old, and were propagated by the seeds collected from B. balsamifera planted in the experimental field of the Tropical Crops Genetic Resources Institute, Chinese Academy of Tropical Agricultural Sciences. They were planted with a planting spacing of 80 cm × 80 cm. On the 20th day of each month (from September 2014 to December 2014, which is the traditional harvest time), 30 one-year old B. balsamifera plants were randomly collected. Their young leaves (leaves on young shoots), mature leaves (leaves which are mature but without yellow spots), senescent leaves (leaves with yellow spots and those with dark brown leaf tips), dead leaves (leaves that have turned dark brown), young shoots (stems from buds to 10-20 cm part without woody parts), and young stems (green stems and not completely woody) were collected. These samples were divided into three parts (replicates), dried under shade, and ground to a fine powder (20-mesh sieve), packed in zip-lock bags, and stored in the refrigerator (4 ℃ ) for oil extraction.
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               Factor Function
Time of growth and type of B. balsamifera plant organs influence the production of oil, its composition, and antioxidant activity. The essential oil level in the young leaves was the highest, followed by mature leaves and senescent leaves, and the oil content was higher in October. A total of 44 compounds were identified. In the essential oils of leaves, the main ingredient is l-borneol, and the content was the highest in senescent leaves and in December. Variations in oil yields did not show the same pattern as the percentages of l-borneol in the essential oil. In the essential oils of young shoots and young stems, the main composition was dimethoxydurene. Therefore, the time of harvest and type of plant organs should be distinguished based on the different harvesting purposes. To extract the volatile oil, the aboveground parts except stems in October should be chosen for harvest. To get a high content of l-borneol in volatile oil, it is more appropriate to select the leaves in December. The antioxidant activity was evaluated using DPPH and BCB assays in this study, and the results proved that the essential oils of B. balsamifera showed a certain antioxidant activity, and the beta-carotene bleaching activity is far stronger than the DPPH radical-scavenging capacity. The young leaves and young shoots showed stronger antioxidant activity due to the high content of dimethoxydurene, beta-caryophyllene, and alpha-caryophyllene.
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               Factor Part Location NP Content
 
Young Shoots (mean value for four months)
Young Shoots Danzhou, Hainan, China
NP Content: 0.14 %
 
Young Stems (mean value for four months)
Young Stems Danzhou, Hainan, China
NP Content: 0.96 %
 
September (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 1.33 %
 
October (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 0.4 %
 
November (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 0.93 %
 
December (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 0.53 %
      Species Name: Lagenaria siceraria
  Factor Name: Cultivar Comparison; Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
The experiment was conducted from July to November 2007 at the experimental station of the University of Abobo-Adjame (Abidjan, Ivory Coast) (latitude between 5° 17′ and 5° 31′ N, longitude between 3° 45′ and 4° 22′ W). During this period, rainfall, mean temperature and humidity varied from 5.33 to 192.28 mm, from 23.3 to 26.4 ℃ and from 86.7 to 96% respectively. Open-pollinated accessions from two edible-seeded L. siceraria (Molina) Standl. cultivars recognisable by their fruit shape (oval or round) were used. Seeds from the round fruit cultivar are characterised by the presence of a cap on the distal side, whereas those from the oval fruit cultivar lack this cap. Differences are also noted between the two cultivars in their rates of seed germination and seedling emergence, the best performances being observed for the round fruit cultivar. However, the visual changes in fruits during their growth as well as at plant whiteness are the same in the two cultivars. Both round and oval fruit cultivars were obtained from the cucurbit germplasm of the university, where they are identified by the alphanumeric codes NI354 and NI260 respectively. Each cultivar was sown on a plot of 20 m × 20 m in 12 holes. Female flowers were tagged after their closure in order to monitor the fruits until the date determined for harvesting. Fruits were harvested at three stages of maturation: (i) 30 days after fruit set (DAFS), at which stage fruits do not grow any more; (ii) 50 DAFS, at which stage the colour of fruits no longer changes; (iii) complete plant whiteness (CPW), indicating the end of plant growth. For each of the three fruit maturation times, five fruits per cultivar were selected. The seeds were extracted from each fruit, washed and dried in the sun for 1 week. After drying, the seeds of all five fruits were grouped and decorticated to obtain seed kernels that were used for analysis.
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               Factor Function
The results of this study showed that there were considerable modifications during fruit maturation in the oilseed gourd L. siceraria and that chemical characterisation of the seed kernel is important for controlling the processes of maturation. The two cultivars of L. siceraria studied should be harvested at 50 days after fruit set (DAFS) owing to their high contents of proteins, lipids, energy and minerals at this stage. At 50 DAFS the leaves of L. siceraria were still green and could serve as a source of nutrients for livestock. However, to obtain the best amino acid composition and biological values of proteins, the round and oval berry cultivars should be harvested at 30 DAFS and complete plant whiteness (CPW) respectively. At these stages their proteins could be used as a supplement. The low digestibility of the proteins at this stage could be improved by appropriate technological treatment.
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               Factor Part Location NP Content
 
Lagenaria siceraria cv. Round berry + Harvesting time: 30 days after fruit set
Seed kernels Abidjan, Cote d'lvoire
NP Content: 612.6 ± 2.8 g/kg dry matter
 
Lagenaria siceraria cv. Round berry + Harvesting time: 50 days after fruit set
Seed kernels Abidjan, Cote d'lvoire
NP Content: 621.9 ± 1.3 g/kg dry matter
 
Lagenaria siceraria cv. Round berry + Harvesting time: complete plant whiteness stage
Seed kernels Abidjan, Cote d'lvoire
NP Content: 645.7 ± 2.1 g/kg dry matter
 
Lagenaria siceraria cv. Oval berry + Harvesting time: 30 days after fruit set
Seed kernels Abidjan, Cote d'lvoire
NP Content: 665.3 ± 4.0 g/kg dry matter
 
Lagenaria siceraria cv. Oval berry + Harvesting time: 50 days after fruit set
Seed kernels Abidjan, Cote d'lvoire
NP Content: 627.1 ± 2.8 g/kg dry matter
 
Lagenaria siceraria cv. Oval berry + Harvesting time: complete plant whiteness stage
Seed kernels Abidjan, Cote d'lvoire
NP Content: 564.1 ± 1.8 g/kg dry matter
      Species Name: Phyllosticta capitalensis
  Factor Name: Rice Medium [4]
              Species Info Factor Info
               Experiment Detail
The fungus Phyllosticta capitalensis was isolated from the leaves of Loropetalum chinense var. rubrum, which collected from Nanjing, Jiangsu Province, P. R. China (31° 14′ N, 118° 22′ E), in August 2019. To prepare the seed culture, the strain was cultured on potato dextrose agar (PDA) at 28 &#8451 for 7 days. Agar plugs were cut into small pieces (approximately 0.5 × 0.5 × 0.5 cm3). Small pieces were added to ten Erlenmeyer flasks (250 mL) with 100 mL of potato dextrose liquid medium, and flasks were incubated on a rotary shaker at 28 &#8451 and 150 rpm for 5 days to prepare seed culture. Solid fermentation was carried out in 200 Erlenmeyer flasks (1 L) each containing 140 g of rice and 210 mL of distilled water with 5 mmol/L Nicotinamide, 0.1 mmol/L 5-aza-2-deoxycytidine, 0.25 mmol/L CuSO4 5H2O, 0.5 g/L MgSO4 and 0.5 g/L NaCl were sterilized at autoclave, and then, 10 mL of seed culture was added into each flask. All flasks were incubated at 28 &#8451 for 30 days.
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               Factor Part Location NP Content
 
Rice Medium (28 degrees Celsius + 30Days)
leaves Nanjing, Jiangsu Province, P. R. China
NP Content: 10 mg
References
1 Essential Oil of Eaglewood Tree: a Product of Pathogenesis
2 Variations in Essential Oil Yield, Composition, and Antioxidant Activity of Different Plant Organs from Blumea balsamifera (L.) DC. at Different Growth Times
3 Effect of harvest time on seed oil and protein contents and compositions in the oleaginous gourd Lagenaria siceraria (Molina) Standl
4 Neuroprotective Activities of Constituents from Phyllosticta capitalensis, an Endophyte Fungus of Loropetalum chinense var. rubrum