Loliolide (BioDeep_00000227318)

Secondary id: BioDeep_00000404892, BioDeep_00000405173

human metabolite PANOMIX_OTCML-2023

代谢物信息卡片

(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

化学式: C11H16O3 (196.1099386)
中文名称: 地芰普内酯
谱图信息: 最多检出来源 Viridiplantae(plant) 0.85%

分子结构信息

SMILES: CC1(C)C[C@@H](C[C@]2(C)C1=CC(=O)O2)O
InChI: InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m0/s1

描述信息

Loliolide, also known as (3s5r)-loliolide, is a member of the class of compounds known as benzofurans. Benzofurans are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Loliolide is soluble (in water) and an extremely weak acidic compound (based on its pKa). Loliolide can be found in sunflower, tea, and wakame, which makes loliolide a potential biomarker for the consumption of these food products.

同义名列表

11 个代谢物同义名

(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one; (6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one; 1,3-Dihydroxy-3,5,5-trimethylcyclohexylidene-4-acetic acid lactone; (6S,7alphaR)-Loliolide; (3S5R)-Loliolide; Digiprolactone; (-)-Loliolide; loliolide; Caulilide; Calendin; Loliolid

数据库引用编号

9 个数据库交叉引用编号

ChEBI: CHEBI:69774
PubChem: 100332
HMDB: HMDB0302428
ChEMBL: CHEMBL227113
KNApSAcK: C00019144
foodb: FDB004536
chemspider: 90666
CAS: 5989-02-6
RefMet: Loliolide

分类词条

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

105 个相关的物种来源信息

2067288 Lessingianthus mollissimus: 10.1021/NP50044A031
2855421 Mikania haenkeana: 10.1016/0031-9422(92)83720-J
1279044 Melilotus messanensis: 10.1016/S0031-9422(98)00453-1
29818 Plantago major:
263974 Bacopa monnieri: 10.1007/S10600-007-0133-Y
318062 Euphorbia hirta:
138560 Veronica persica: 10.1016/S0305-1978(99)00122-2
65704 Athyrium yokoscense: 10.1080/10575639808048868
237933 Viburnum dilatatum: 10.1016/0031-9422(95)00790-3
1826188 Rosa taiwanensis: 10.1002/JCCS.199500076
13129 Lythrum salicaria: 10.1515/ZNC-2001-1-203
137693 Polygonum aviculare: 10.2307/3754908
2816892 Heteroplexis microcephala: 10.1021/NP900213W
139772 Triadica sebifera: 10.1021/NP50057A037
183589 Pseudo-nitzschia multistriata: 10.3390/MD18060313
568080 Erythrophleum fordii: 10.1016/J.BMC.2008.09.021
66392 Morus australis: 10.1002/PTR.4803
248361 Morus indica: 10.1002/PTR.4803
3498 Morus alba: 10.1002/PTR.4803
66393 Morus bombycis: 10.1002/PTR.4803
109851 Macaranga triloba: 10.1016/J.PHYTOCHEM.2003.10.026
1053410 Xanthium spinosum: 10.1016/S0031-9422(00)90847-1
28513 Salvia divinorum:
3316 Thuja plicata: 10.1016/S0305-1978(00)00047-8
137893 Saussurea medusa: 10.1016/S0031-9422(01)00429-0
1933756 Salvia sahendica: 10.1021/NP1002516
115466 Euterpe oleracea: 10.1021/JF801792N
65003 Cheirolophus uliginosus: 10.1016/S0031-9422(00)89537-0
145819 Mantisalca salmantica: 10.1016/0031-9422(93)85349-V
40340 Pellia epiphylla: 10.1016/S0031-9422(97)00414-7
554381 Hydrocotyle leucocephala: 10.1016/J.PHYTOCHEM.2006.03.004
172644 Broussonetia papyrifera: 10.1021/NP010288L
52497 Prangos pabularia: 10.1016/S0031-9422(02)00023-7
75943 Lactuca serriola: 10.1016/0031-9422(92)83321-O
41496 Calendula officinalis:
1892689 Gentiana pedicellata: 10.1055/S-2007-969859
3397 Cycas circinalis: 10.1055/S-0029-1240743
1284457 Rhaponticum centauroides: 10.1016/0031-9422(94)00688-P
362629 Rhaponticum canariense: 10.1016/0031-9422(94)00688-P
145817 Rhaponticum coniferum: 10.1016/0031-9422(94)00688-P
41507 Centaurea aspera: 10.1016/J.PHYTOCHEM.2005.06.004
124929 Centaurea diffusa: 10.1016/S0305-1978(01)00115-6
53717 Calyptocarpus vialis: 10.1016/0031-9422(95)00942-6
2045269 Peperomia heyneana: 10.1021/NP070089N
119188 Pulicaria incisa: 10.1016/0031-9422(92)80452-K
318066 Tridax procumbens: 10.1139/V08-097
405319 Piper sarmentosum: 10.1021/JF071963L
247689 Piper lolot: 10.1021/JF071963L
557628 Carpesium macrocephalum: 10.1007/BF02975426
53809 Oxalis pes-caprae: 10.1080/14786410902809286
4232 Helianthus annuus:
167911 Ajuga decumbens: 10.1021/NP990033W
28525 Menyanthes trifoliata: 10.1086/325638
13427 Cichorium intybus: 10.1016/S0031-9422(01)00072-3
86312 Artemisia ludoviciana: 10.1016/0031-9422(91)84211-A
154990 Euphorbia helioscopia:
746341 Pimelea simplex: 10.1071/CH9792495
182999 Acanthospermum hispidum: 10.1021/NP9905057
668396 Sinularia capillosa: 10.1021/NP9008078
112817 Casearia sylvestris: 10.1248/CPB.57.636
1205701 Brachystemma calycinum: 10.1021/NP200048U
1548649 Pterocaulon polystachyum: 10.1055/S-2001-17365
133239 Otanthus maritimus: 10.1016/0031-9422(88)80289-9
174463 Helminthotheca echioides: 10.1016/0031-9422(92)80390-Z
76276 Senecio vulgaris: 10.3184/030823410X12830855365409
108357 Sida acuta: 10.1007/BF02976704
2861340 Pontederia africana: 10.1002/JCCS.200400035
1209451 Anaphalis busua: 10.1016/S0031-9422(00)81462-4
2876 Dictyota dichotoma: 10.1080/1057563031000072523
318068 Xanthium strumarium: 10.1016/0031-9422(90)83040-8
1979456 Xanthium pungens: 10.1016/0031-9422(90)83040-8
1548666 Sphaeranthus suaveolens: 10.1055/S-0029-1186031
74381 Undaria pinnatifida:
176579 Schkuhria pinnata: 10.1016/0031-9422(90)85113-T
156996 Dictyopteris divaricata: 10.1021/NP040099D
189238 Jacobaea erucifolia: 10.1248/CPB.58.991
186967 Jacobaea argunensis: 10.1248/CPB.58.991
362630 Rhaponticum carthamoides: 10.1007/BF02494759
362645 Rhaponticum serratuloides: 10.1007/BF02494759
167923 Vitex quinata: 10.1016/J.PHYTOL.2011.03.007
159976 Viscum coloratum:
1284450 Volutaria tubuliflora: 10.1016/0031-9422(90)85370-U
4164 Digitalis purpurea:
221052 Codium subtubulosum: 10.1016/J.FITOTE.2010.07.011
552636 Xanthium strumarium var. canadense: 10.1016/S0031-9422(00)86900-9
53861 Securigera varia: 10.1016/0031-9422(73)85133-7
1718265 Acanthosyris paulo-alvinii: 10.1016/S0031-9422(97)00363-4
589831 Cota palaestina: 10.1002/HLCA.200790012
155640 Melia azedarach: 10.1248/CPB.36.609
1111689 Padina tetrastromatica: 10.1002/CHIN.199631171
659328 Padina antillarum: 10.1002/CHIN.199631171
4392 Eucommia ulmoides: 10.1016/0031-9422(94)85042-9
358661 Bunias orientalis: 10.1016/0031-9422(96)00020-9
82756 Linzia glabra: 10.1055/S-2007-969524
74652 Rosa laevigata: 10.1002/JCCS.199100050
198361 Canscora alata: 10.1016/S0031-9422(00)84400-3
259861 Arctotis fastuosa: 10.1055/S-2000-8608
3972 Viscum album: 10.1002/PTR.2464
548576 Sargassum aquifolium: 10.1515/BOTM.1985.28.11.501
681511 Zanthoxylum setulosum: 10.1021/NP50039A020
4522 Lolium perenne: 10.1039/J39700001091
282203 Anacyclus monanthos: 10.1055/S-0031-1282578
268113 Urospermum picroides: 10.1016/S0031-9422(00)89805-2
122557 Urospermum dalechampii: 10.1016/S0031-9422(00)89805-2
9606 Homo sapiens: -

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。

文献列表

Lei-Lei Li, Zheng Li, Yonggen Lou, Scott J Meiners, Chui-Hua Kong. (-)-Loliolide is a general signal of plant stress that activates jasmonate-related responses. The New phytologist. 2023 06; 238(5):2099-2112. doi: 10.1111/nph.18644. [PMID: 36444519]
Feng-Li Li, Xin Chen, Hui-Min Luo, Scott J Meiners, Chui-Hua Kong. Root-secreted (-)-loliolide modulates both belowground defense and aboveground flowering in Arabidopsis and tobacco. Journal of experimental botany. 2023 02; 74(3):964-975. doi: 10.1093/jxb/erac439. [PMID: 36342376]
Lei Wang, Hyun-Soo Kim, Jun-Geon Je, Xiaoting Fu, Caoxing Huang, Ginnae Ahn, Jae-Young Oh, K K Asanka Sanjeewa, Jiachao Xu, Xin Gao, In-Kyu Yeo, You-Jin Jeon. In Vitro and In Vivo Photoprotective Effects of (-)-Loliode Isolated from the Brown Seaweed, Sargassum horneri. Molecules (Basel, Switzerland). 2021 Nov; 26(22):. doi: 10.3390/molecules26226898. [PMID: 34833989]
Hao Chi, Xia Qi, Xiaohui Wang, Ying Wang, Xihong Han, Jiao Wang, Hongwei Wang. Preparative separation and purification of loliolide and epiloliolide from Ascophyllum nodosum using amine-based microporous organic polymer for solid phase extraction coupled with macroporous resin and prep-HPLC. Analytical methods : advancing methods and applications. 2021 Apr; 13(16):1939-1944. doi: 10.1039/d1ay00186h. [PMID: 33913944]
Jun Gu Kim, Jin Woo Lee, Thi Phuong Linh Le, Jae Sang Han, Yong Beom Cho, Haeun Kwon, Dongho Lee, Mi Kyeong Lee, Bang Yeon Hwang. Sesquiterpenoids from Chrysanthemum indicum with Inhibitory Effects on NO Production. Journal of natural products. 2021 03; 84(3):562-569. doi: 10.1021/acs.jnatprod.0c01121. [PMID: 33667099]
Hyo-Geun Lee, Hyun-Soo Kim, Jun-Geon Je, Jin Hwang, K K Asanka Sanjeewa, Dae-Sung Lee, Kyung-Mo Song, Yun-Sang Choi, Min-Cheol Kang, You-Jin Jeon. Lipid Inhibitory Effect of (-)-loliolide Isolated from Sargassum horneri in 3T3-L1 Adipocytes: Inhibitory Mechanism of Adipose-Specific Proteins. Marine drugs. 2021 Feb; 19(2):. doi: 10.3390/md19020096. [PMID: 33567534]
Abdul Rahim, Yohei Saito, Shuichi Fukuyoshi, Katsunori Miyake, Masuo Goto, Chin-Ho Chen, Gemini Alam, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto. Paliasanines A-E, 3,4-Methylenedioxyquinoline Alkaloids Fused with a Phenyl-14-oxabicyclo[3.2.1]octane Unit from Melochia umbellata var. deglabrata. Journal of natural products. 2020 10; 83(10):2931-2939. doi: 10.1021/acs.jnatprod.0c00454. [PMID: 32946697]
Lei-Lei Li, Huan-Huan Zhao, Chui-Hua Kong. (-)-Loliolide, the most ubiquitous lactone, is involved in barnyardgrass-induced rice allelopathy. Journal of experimental botany. 2020 02; 71(4):1540-1550. doi: 10.1093/jxb/erz497. [PMID: 31677347]
Sun Young Kim, Joo Young Lee, Changho Jhin, Ji Min Shin, Myungsuk Kim, Hong Ruyl Ahn, Gyhye Yoo, Yang-Ju Son, Sang Hoon Jung, Chu Won Nho. Reduction of Hepatic Lipogenesis by Loliolide and Pinoresinol from Lysimachia vulgaris via Degrading Liver X Receptors. Journal of agricultural and food chemistry. 2019 Nov; 67(45):12419-12427. doi: 10.1021/acs.jafc.9b01488. [PMID: 31610126]
Mika Murata, Yusuke Nakai, Kei Kawazu, Masumi Ishizaka, Hideyuki Kajiwara, Hiroshi Abe, Kasumi Takeuchi, Yuki Ichinose, Ichiro Mitsuhara, Atsushi Mochizuki, Shigemi Seo. Loliolide, a Carotenoid Metabolite, Is a Potential Endogenous Inducer of Herbivore Resistance. Plant physiology. 2019 04; 179(4):1822-1833. doi: 10.1104/pp.18.00837. [PMID: 30700538]
Yulin Ren, Gerardo D Anaya-Eugenio, Austin A Czarnecki, Tran Ngoc Ninh, Chunhua Yuan, Hee-Byung Chai, Djaja D Soejarto, Joanna E Burdette, Esperanza J Carcache de Blanco, A Douglas Kinghorn. Cytotoxic and NF-κB and mitochondrial transmembrane potential inhibitory pentacyclic triterpenoids from Syzygium corticosum and their semi-synthetic derivatives. Bioorganic & medicinal chemistry. 2018 08; 26(15):4452-4460. doi: 10.1016/j.bmc.2018.07.025. [PMID: 30057155]
Janggyoo Choi, Kee Dong Yoon, Jinwoong Kim. Chemical constituents from Taraxacum officinale and their α-glucosidase inhibitory activities. Bioorganic & medicinal chemistry letters. 2018 02; 28(3):476-481. doi: 10.1016/j.bmcl.2017.12.014. [PMID: 29254644]
Chueh-Yao Chung, Ching-Hsuan Liu, Thierry Burnouf, Guey-Horng Wang, Shun-Pang Chang, Alagie Jassey, Chen-Jei Tai, Cheng-Jeng Tai, Ching-Jang Huang, Christopher D Richardson, Ming-Hong Yen, Chun-Ching Lin, Liang-Tzung Lin. Activity-based and fraction-guided analysis of Phyllanthus urinaria identifies loliolide as a potent inhibitor of hepatitis C virus entry. Antiviral research. 2016 06; 130(?):58-68. doi: 10.1016/j.antiviral.2016.03.012. [PMID: 27012176]
Lin Ni, Xing Zhou, Jie Ma, Xiao-Mei Zhang, Chuang-Jun Li, Li Li, Da-Jian Yang, Yang-Yang Shao, Si-Bai Zhou, Tian-Tai Zhang, Dong-Ming Zhang. Wilfordonols A-D: four new norsesquiterpenes from the leaves of Tripterygium wilfordii. Journal of Asian natural products research. 2015; 17(6):615-24. doi: 10.1080/10286020.2015.1054380. [PMID: 26096035]
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Nina Corlay, Leen Delang, Emmanuelle Girard-Valenciennes, Johan Neyts, Patricia Clerc, Jacqueline Smadja, Françoise Guéritte, Pieter Leyssen, Marc Litaudon. Tigliane diterpenes from Croton mauritianus as inhibitors of chikungunya virus replication. Fitoterapia. 2014 Sep; 97(?):87-91. doi: 10.1016/j.fitote.2014.05.015. [PMID: 24879904]
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Catherine Argyropoulou, Anastasia Karioti, Helen Skaltsa. Minor labdane diterpenes from Marrubium thessalum. Chemistry & biodiversity. 2011 Oct; 8(10):1880-90. doi: 10.1002/cbdv.201000215. [PMID: 22006716]
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