Longifolene (BioDeep_00000004306)

 

Secondary id: BioDeep_00000327975, BioDeep_00000603357, BioDeep_00001103467, BioDeep_00001883193

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0²,⁹]undecane

化学式: C15H24 (204.1878)
中文名称: 长叶烯, （+）-长叶烯
谱图信息: 最多检出来源 Homo sapiens(natural_products) 32.56%

分子结构信息

SMILES: C=C1C2CCC3C2C(C)(C)CCCC13C
InChI: InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3

描述信息

Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily Liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts .
Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts .
(+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1].
(+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1].
(+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1].

同义名列表

5 个代谢物同义名

3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0²,⁹]undecane; (+)-Longifolene; LONGIFOLENE; Longifolene; (+)-Longifolene



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

7 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(2)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

275 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 10 ALOX5, BDNF, CAMKK2, CAT, CNR2, GGPS1, IL13, NR3C1, PRKAA2, TYR
Peripheral membrane protein 1 ALOX5
Endoplasmic reticulum membrane 1 SCD
Nucleus 4 CAMKK2, NR3C1, PRKAA2, SERPINA3
cytosol 7 ALOX5, CAMKK2, CAT, GGPS1, LIPE, NR3C1, PRKAA2
dendrite 3 BDNF, CNR2, PRKAA2
centrosome 1 NR3C1
nucleoplasm 5 ALOX5, CAMKK2, GGPS1, NR3C1, PRKAA2
Cell membrane 2 LIPE, OPRD1
Multi-pass membrane protein 3 KCNA3, OPRD1, SCD
Synapse 1 NR3C1
cell surface 1 ADIPOQ
glutamatergic synapse 1 KCNA3
Golgi apparatus 1 PRKAA2
Golgi membrane 1 INS
neuronal cell body 1 PRKAA2
presynaptic membrane 2 KCNA3, OPRD1
synaptic vesicle 1 BDNF
Cytoplasm, cytosol 2 ALOX5, LIPE
Lysosome 1 TYR
plasma membrane 3 CNR2, KCNA3, OPRD1
synaptic vesicle membrane 1 OPRD1
Membrane 8 BDNF, CAT, KCNA3, LIPE, NR3C1, OPRD1, PRKAA2, SCD
axon 3 BDNF, KCNA3, PRKAA2
caveola 1 LIPE
extracellular exosome 2 CAT, SERPINA3
endoplasmic reticulum 3 ADIPOQ, CNR2, SCD
extracellular space 8 ADIPOQ, ALOX5, BDNF, IL13, IL4, IL6, INS, SERPINA3
perinuclear region of cytoplasm 5 ALOX5, BDNF, GGPS1, KCNA3, TYR
mitochondrion 2 CAT, NR3C1
protein-containing complex 2 CAT, NR3C1
intracellular membrane-bounded organelle 2 CAT, TYR
Single-pass type I membrane protein 1 TYR
Secreted 6 ADIPOQ, BDNF, IL13, IL4, IL6, INS
extracellular region 9 ADIPOQ, ALOX5, BDNF, CAT, IL13, IL4, IL6, INS, SERPINA3
mitochondrial matrix 2 CAT, NR3C1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 NR3C1
Nucleus membrane 1 ALOX5
nuclear membrane 1 ALOX5
external side of plasma membrane 1 IL13
perikaryon 1 CNR2
Z disc 1 GGPS1
nucleolus 1 SCD
Melanosome membrane 1 TYR
Golgi-associated vesicle 1 TYR
postsynaptic membrane 2 CNR2, KCNA3
Cytoplasm, perinuclear region 2 ALOX5, GGPS1
Membrane raft 1 KCNA3
Cytoplasm, cytoskeleton, spindle 1 NR3C1
focal adhesion 1 CAT
spindle 1 NR3C1
Peroxisome 1 CAT
collagen trimer 1 ADIPOQ
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 ADIPOQ, SERPINA3
nuclear speck 2 NR3C1, PRKAA2
Cell projection, neuron projection 1 CAMKK2
neuron projection 2 CAMKK2, OPRD1
chromatin 1 NR3C1
Chromosome 1 NR3C1
blood microparticle 1 SERPINA3
[Isoform 2]: Cell membrane 1 KCNA3
nuclear envelope 1 ALOX5
Nucleus envelope 1 ALOX5
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
Nucleus, nucleoplasm 1 NR3C1
Cell projection, dendrite 1 CNR2
Melanosome 1 TYR
cytoplasmic stress granule 1 PRKAA2
Cytoplasm, myofibril, sarcomere, Z line 1 GGPS1
voltage-gated potassium channel complex 1 KCNA3
ficolin-1-rich granule lumen 2 ALOX5, CAT
secretory granule lumen 4 ALOX5, CAT, INS, SERPINA3
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 BDNF, IL6, INS
nuclear matrix 1 ALOX5
platelet alpha granule lumen 1 SERPINA3
axon terminus 1 OPRD1
transport vesicle 1 INS
azurophil granule lumen 1 SERPINA3
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 1 OPRD1
neuronal dense core vesicle 1 OPRD1
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
calyx of Held 1 KCNA3
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
[Isoform 1]: Cell membrane 1 KCNA3
dendrite membrane 1 OPRD1
nucleotide-activated protein kinase complex 1 PRKAA2
[Isoform Alpha]: Cytoplasm 1 NR3C1
catalase complex 1 CAT
[Isoform Beta]: Nucleus 1 NR3C1
[Isoform Alpha-B]: Nucleus 1 NR3C1
interleukin-6 receptor complex 1 IL6
Nucleus intermembrane space 1 ALOX5
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
spine apparatus 1 OPRD1


文献列表

  • Furong Xia, Jingping Du, Kai Wang, Lu Liu, Limin Ba, Huan Liu, Yanhui Liu. Application of Multiple Strategies To Debottleneck the Biosynthesis of Longifolene by Engineered Saccharomyces cerevisiae. Journal of agricultural and food chemistry. 2022 Sep; 70(36):11336-11343. doi: 10.1021/acs.jafc.2c04405. [PMID: 36047715]
  • Madhuri Grover, Tapan Behl, Tarun Virmani, Mohit Sanduja, Hafiz A Makeen, Mohammed Albratty, Hassan A Alhazmi, Abdulkarim M Meraya, Simona Gabriela Bungau. Exploration of Cytotoxic Potential of Longifolene/Junipene Isolated from Chrysopogon zizanioides. Molecules (Basel, Switzerland). 2022 Sep; 27(18):. doi: 10.3390/molecules27185764. [PMID: 36144491]
  • Yujin Cao, Rubing Zhang, Wei Liu, Guang Zhao, Wei Niu, Jiantao Guo, Mo Xian, Huizhou Liu. Manipulation of the precursor supply for high-level production of longifolene by metabolically engineered Escherichia coli. Scientific reports. 2019 01; 9(1):95. doi: 10.1038/s41598-018-36495-w. [PMID: 30643175]
  • Rungarun Tisgratog, Chutipong Sukkanon, John P Grieco, Unchalee Sanguanpong, Kamlesh R Chauhan, Joel R Coats, Theeraphap Chareonviriyaphap. Evaluation of the Constituents of Vetiver Oil Against Anopheles minimus (Diptera: Culicidae), a Malaria Vector in Thailand. Journal of medical entomology. 2018 01; 55(1):193-199. doi: 10.1093/jme/tjx188. [PMID: 29029183]
  • Miao Wang, Dongyu Gu, Haoquan Li, Qi Wang, Jie Kang, Tingting Chu, Hong Guo, Yi Yang, Jing Tian. Rapid prediction and identification of lipase inhibitors in volatile oil from Pinus massoniana L. needles. Phytochemistry. 2017 Sep; 141(?):114-120. doi: 10.1016/j.phytochem.2017.06.002. [PMID: 28609696]
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  • Lin Yang, Lirui Qiao, Dan Xie, Jungui Dai, Shunxing Guo. [Sesquiterpenes and monoterpene from Aquilaria sinensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Jul; 37(13):1973-6. doi: . [PMID: 23019881]
  • Rafal Szmigielski, Marek Cieslak, Krzysztof J Rudziński, Barbara Maciejewska. Identification of volatiles from Pinus silvestris attractive for Monochamus galloprovincialis using a SPME-GC/MS platform. Environmental science and pollution research international. 2011 Aug; 19(7):2860-9. doi: 10.1007/s11356-012-0792-5. [PMID: 22322293]
  • Cheryl Lans, Nancy Turner. Organic parasite control for poultry and rabbits in British Columbia, Canada. Journal of ethnobiology and ethnomedicine. 2011 Jul; 7(?):21. doi: 10.1186/1746-4269-7-21. [PMID: 21756341]
  • Christopher I Keeling, Sabrina Weisshaar, Steven G Ralph, Sharon Jancsik, Britta Hamberger, Harpreet K Dullat, Jörg Bohlmann. Transcriptome mining, functional characterization, and phylogeny of a large terpene synthase gene family in spruce (Picea spp.). BMC plant biology. 2011 Mar; 11(?):43. doi: 10.1186/1471-2229-11-43. [PMID: 21385377]
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  • Frank Bedon, Claude Bomal, Sébastien Caron, Caroline Levasseur, Brian Boyle, Shawn D Mansfield, Axel Schmidt, Jonathan Gershenzon, Jacqueline Grima-Pettenati, Armand Séguin, John MacKay. Subgroup 4 R2R3-MYBs in conifer trees: gene family expansion and contribution to the isoprenoid- and flavonoid-oriented responses. Journal of experimental botany. 2010 Sep; 61(14):3847-64. doi: 10.1093/jxb/erq196. [PMID: 20732878]
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