Lupenone (BioDeep_00000000090)

PANOMIX_OTCML-2023 Antitumor activity natural product Volatile Flavor Compounds

代谢物信息卡片

(1S,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,3a,4,5,5a,5b,6,7,7a,8,11a,11b,12,13,13a,13b-octadecahydro-9H-cyclopenta[a]chrysen-9-one

化学式: C30H48O (424.3704958)
中文名称: 羽扇烯酮
谱图信息: 最多检出来源 Viridiplantae(otcml) 29.73%

Reviewed

Last reviewed on 2024-10-23.

Cite this Page

Lupenone. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/lupenone (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000000090). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C=C(C)C1CCC2(C)CCC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC43C)C12
InChI: InChI=1S/C30H48O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-23,25H,1,9-18H2,2-8H3

描述信息

Lupenone is a triterpenoid. It has a role as a metabolite. It derives from a hydride of a lupane.
Lupenone is a natural product found in Liatris acidota, Euphorbia larica, and other organisms with data available.
A natural product found in Cupania cinerea.
Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2].
Lupenone is an orally active lupine-type triterpenoid that can be isolated from Musa basjoo. Lupenone Lupenone plays a role through the PI3K/Akt/mTOR and NF-κB signaling pathways. Lupenone has anti-inflammatory, antiviral, antidiabetic and anticancer activities[1][2][3].
Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2].

同义名列表

9 个代谢物同义名

(1S,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,3a,4,5,5a,5b,6,7,7a,8,11a,11b,12,13,13a,13b-octadecahydro-9H-cyclopenta[a]chrysen-9-one; (1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one; (1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one; (1R,3aR,4S,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-one; Lup-20(29)-en-3-one; Lup-20(30)-en-3-one; Lupenone; lupeone; Lupenone

数据库引用编号

16 个数据库交叉引用编号

ChEBI: CHEBI:67823
KEGG: C16990
PubChem: 92158
Metlin: METLIN71486
ChEMBL: CHEMBL486393
MeSH: lupenone
ChemIDplus: 0001617705
KNApSAcK: C00019220
chemspider: 83203
CAS: 1617-70-5
medchemexpress: HY-N2590
PMhub: MS000025534
MetaboLights: MTBLC67823
NIKKAJI: J82.270A
PubChem: 96023476
KNApSAcK: 67823

分类词条

三萜类

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)

166 个相关的物种来源信息

205042 - Acacia dealbata: 10.1080/10575639608043247
1641247 - Achyranthemum paniculatum: 10.1016/0031-9422(89)80195-5
1392102 - Adenophora capillaris: 10.1016/0305-1978(95)00082-8
1392103 - Adenophora coelestis: 10.1016/0305-1978(95)00082-8
187270 - Adenophora hunanensis: 10.1016/0305-1978(95)00082-8
1049772 - Adenophora lamarckii: 10.1016/0305-1978(95)00082-8
361368 - Adenophora liliifolia: 10.1016/0305-1978(95)00082-8
226229 - Adenophora pereskiifolia: 10.1016/0305-1978(95)00082-8
82277 - Adenophora potaninii: 10.1016/0305-1978(95)00082-8
226228 - Adenophora stenophylla: 10.1016/0305-1978(95)00082-8
82279 - Adenophora stricta: 10.1016/0305-1978(95)00082-8
82280 - Adenophora wawreana: 10.4268/CJCMM20111611
306504 - Aglaia forbesii: 10.1016/J.PHYTOCHEM.2007.06.016
1475121 - Aglaia rubiginosa: 10.1016/J.PHYMED.2009.10.015
1561840 - Albizia gummifera: 10.1016/S0367-326X(00)00276-8
210371 - Albizia schimperiana: 10.1016/S0367-326X(00)00259-8
138525 - Albizia versicolor: 10.1016/S0367-326X(00)00259-8
148671 - Anadenanthera colubrina: 10.1055/S-2004-818920
3702 - Arabidopsis thaliana: 10.1021/OL800389Q
259859 - Arctotheca calendula: 10.1016/0031-9422(90)89036-9
467254 - Arctotheca populifolia: 10.1016/0031-9422(90)89036-9
259893 - Artemisia argyi: 10.1248/CPB.32.723
259893 - Artemisia argyi Lévl.et Vant.: -
119829 - Astragalus mongholicus: 10.1055/S-2006-960221
1128101 - Balanophora indica: 10.1016/0031-9422(88)80772-6
3806 - Bauhinia purpurea: 10.1002/JCCS.199700056
21017 - Betula alleghaniensis: 10.1016/S0031-9422(00)97169-3
216994 - Betula lenta:
1745020 - Bishopiella elegans: 10.1016/0031-9422(91)83025-G
1205696 - Blainvillea acmella: 10.1016/S0031-9422(00)83115-5
173701 - Boswellia sacra: 10.1248/CPB.58.1541
106616 - Bruguiera cylindrica: 10.1071/CH05010
106618 - Bruguiera parviflora:
56060 - Butea monosperma: 10.4038/JNSFSR.V18I2.8195
667327 - Calophyllum gracilipes: 10.1016/S0040-4039(97)01032-0
1321791 - Campylospermum flavum: 10.1016/S0305-1978(02)00083-2
85180 - Celastrus: 10.1248/CPB.48.1079
489979 - Celastrus hindsii: 10.1248/CPB.48.1079
172013 - Ceriops decandra: 10.1071/CH05087
13422 - Chrysanthemum: 10.1016/S0305-1978(98)00070-2
171767 - Chuquiraga ulicina: 10.1016/S0031-9422(99)00362-3
114282 - Cichorium spinosum: 10.1021/JF025848G
165298 - Cissus quadrangularis: 10.1016/0031-9422(91)85270-A
1392584 - Codonopsis benthamii: 10.1016/0305-1978(95)00082-8
1392586 - Codonopsis bulleyana: 10.1016/0305-1978(95)00082-8
1392587 - Codonopsis canescens: 10.1016/0305-1978(95)00082-8
1392589 - Codonopsis chlorocodon: 10.1016/0305-1978(95)00082-8
942849 - Codonopsis clematidea: 10.1016/0305-1978(95)00082-8
103999 - Codonopsis lanceolata: 10.1016/0305-1978(95)00082-8
1678352 - Codonopsis macrocalyx: 10.1016/0305-1978(95)00082-8
1392599 - Codonopsis meleagris: 10.1016/0305-1978(95)00082-8
86864 - Codonopsis pilosula: 10.1016/0305-1978(95)00082-8
1392605 - Codonopsis subglobosa: 10.1016/0305-1978(95)00082-8
1392606 - Codonopsis subscaposa: 10.1016/0305-1978(95)00082-8
1049783 - Codonopsis ussuriensis: 10.1016/0305-1978(95)00082-8
504179 - Croton arboreus: 10.1021/NP030485F
3656 - Cucumis melo: 10.1016/0031-9422(82)85222-9
405131 - Curio talinoides:
2918710 - Daphne aurantiaca: 10.1021/NP9005053
1954552 - Deguelia amazonica: 10.1016/S0031-9422(00)98664-3
1954552 - Deguelia amazonica: 10.3987/COM-92-6288
1225674 - Derris cuneifolia:
413758 - Diospyros maritima:
268842 - Diospyros mollis: 10.1016/S0031-9422(97)01020-0
268843 - Diospyros rhodocalyx: 10.1055/S-2006-958085
589132 - Diospyros wallichii: 10.1139/V10-084
54988 - Dipteryx alata: 10.3390/MOLECULES15118193
48244 - Discaria chacaye: 10.1016/0031-9422(73)80719-8
693047 - Dysoxylum malabaricum:
274428 - Echinops niveus: 10.1016/0031-9422(90)85217-4
1569394 - Eremanthus capitatus: 10.1016/0031-9422(81)85163-1
1548342 - Eremanthus glomerulatus:
568080 - Erythrophleum fordii: 10.1016/J.BMC.2008.09.021
1136744 - Esenbeckia berlandieri: 10.1016/S0305-1978(01)00138-7
154986 - Euphorbia aphylla: 10.1515/ZNC-1988-1-206
3991 - Euphorbia characias: 10.1515/ZNC-1988-11-1202
38844 - Euphorbia cyparissias:
212879 - Euphorbia drupifera: 10.1016/J.FITOTE.2007.02.002
1031526 - Euphorbia larica: 10.1351/PAC198153061101
1087772 - Euphorbia nicaeensis: 10.1515/ZNC-1988-11-1202
38846 - Euphorbia peplus: 10.1515/ZNC-1988-11-1202
38847 - Euphorbia segetalis:
38847 - Euphorbia segetalis: 10.1016/S0031-9422(03)00007-4
154997 - Euphorbia stygiana: 10.1016/S0031-9422(03)00007-4
154997 - Euphorbia stygiana: 10.1016/S0031-9422(97)01011-X
464037 - Festuca argentina: 10.1016/0305-1978(96)00011-7
1504337 - Festuca hieronymi: 10.1016/0305-1978(96)00011-7
1233750 - Gardenia saxatilis: 10.1016/S0378-8741(03)00261-7
268092 - Gelasia cretica: 10.1021/NP0103665
107362 - Geoffroea decorticans: 10.1016/S0031-9422(98)00277-5
283122 - Glochidion puberum: 10.1016/S0031-9422(00)89705-8
271535 - Glochidion zeylanicum: 10.1016/S0031-9422(00)85232-2
280743 - Haploclathra paniculata: 10.1016/S0031-9422(00)84543-4
1442637 - Helichrysum anomalum: 10.1016/0031-9422(89)80195-5
261799 - Helichrysum retortum: 10.1016/0031-9422(89)80195-5
434666 - Hilliardiella aristata: 10.1016/0031-9422(82)85189-3
268978 - Hypericum balearicum: 10.1515/ZNC-1994-5-617
318058 - Ixeris chinensis: 10.1248/CPB.44.509
179690 - Joannesia princeps: 10.1016/S0031-9422(96)00777-7
317279 - Kleinia galpinii: 10.1016/0031-9422(82)85252-7
189219 - Kleinia neriifolia: 10.1515/ZNC-1995-5-617
2067306 - Lepidaploa myriocephala: 10.1016/S0305-1978(02)00079-0
1911708 - Leucheria hahnii: 10.1016/0031-9422(89)85056-3
496634 - Leucheria thermarum: 10.1016/0031-9422(89)85056-3
102783 - Liatris acidota: 10.1016/0031-9422(83)83036-2
3983 - Manihot esculenta: 10.1055/S-2003-38488
1048568 - Metalasia capitata: 10.1016/0031-9422(90)83033-W
1081520 - Monteverdia ilicifolia: 10.1590/S0103-50531999000600017
1825850 - Monteverdia truncata: 10.1590/S0103-50531999000600017
45164 - Muntingia calabura: 10.1016/S0031-9422(03)00112-2
171746 - Mutisia acerosa: 10.1016/S0031-9422(00)89799-X
482584 - Nassauvia pyramidalis: 10.1016/S0031-9422(00)89799-X
2306952 - Nassauvia uniflora: 10.1016/S0031-9422(00)89799-X
2306984 - Neolitsea parvigemma: 10.1002/JCCS.199800018
500429 - Notholaena neglecta: 10.1021/NP50050A009
705300 - Ormosia henryi: 10.1016/J.FITOTE.2011.10.007
540062 - Oxyphyllum ulicinum: 10.1016/0031-9422(88)80118-3
943304 - Pachira glabra: 10.1590/S0103-50532002000200022
34243 - Packera streptanthifolia: 10.1016/S0031-9422(00)84168-0
460347 - Perezia pilifera: 10.1016/S0031-9422(00)97880-4
68554 - Phellodendron amurense:
68554 - Phellodendron amurense: 10.1248/CPB.53.1118
697203 - Phellodendron amurense var. wilsonii: 10.1021/NP030034V
354509 - Phellodendron chinense var. glabriusculum: 10.1021/NP030034V
212690 - Picris hieracioides: 10.1248/CPB.43.1634
1548366 - Piptolepis ericoides: 10.1016/0031-9422(81)85163-1
33090 - Plants: -
115002 - Platypodium elegans: 10.1016/S0367-326X(00)00279-3
76149 - Plumbago zeylanica: 10.1016/J.FITOTE.2004.03.009
1504338 - Poa huecu: 10.1021/NP50052A040
56065 - Pongamia pinnata:
2651278 - Pongamia pinnata var. pinnata: 10.1021/NP030207G
1227256 - Proteopsis argentea: 10.1016/0031-9422(81)85165-5
1392590 - Pseudocodon convolvulaceus: 10.1016/0305-1978(95)00082-8
1071199 - Pterocarpus santalinus: 10.1016/S0031-9422(00)97131-0
58331 - Quercus suber: 10.1021/NP50034A017
1225085 - Salacia beddomei: 10.1016/0031-9422(95)00424-6
1685714 - Salvia multicaulis: 10.1016/S0031-9422(97)00540-2
1200507 - Salvia recognita: 10.1016/S0031-9422(97)01056-X
2650239 - Sapium stylare: 10.1016/0031-9422(93)85112-5
48872 - Sarmienta scandens: 10.1016/S0031-9422(00)97239-X
254911 - Saussurea japonica: 10.1021/NP9603941
197987 - Scaevola spinescens: 10.1055/S-2006-957961
18794 - Senecio: 10.1016/S0031-9422(00)81571-X
405109 - Senecio crassissimus: 10.1016/S0031-9422(00)84168-0
370702 - Senegalia gaumeri: 10.1515/ZNC-2002-9-1002
381101 - Senegalia mellifera: 10.1016/J.PHYTOCHEM.2004.03.002
346999 - Senna siamea: 10.1016/S0031-9422(01)00025-5
354518 - Skimmia laureola: 10.1016/0031-9422(88)80473-4
161271 - Stauntonia obovatifoliola: 10.1016/J.PHYTOCHEM.2008.03.004
336154 - Stenocereus beneckei: 10.1021/NP50085A017
189254 - Synotis nagensium: 10.1021/NP049831Z
3743 - Synsepalum dulcificum: 10.1007/S10600-010-9658-6
131536 - Taraxacum japonicum: 10.1248/BPB.22.606
1534674 - Tephroseris helenitis: 10.1016/S0031-9422(00)86705-9
1534677 - Tephroseris longifolia: 10.1016/S0031-9422(00)86705-9
62125 - Tephrosia villosa: 10.1016/S0031-9422(00)95025-8
62125 - Tephrosia villosa: 10.1021/NP0302100
1924228 - Terminalia glabrescens: 10.1590/S0103-50532003000300021
54894 - Tipuana tipu: 10.1515/ZNC-2003-3-411
1289396 - Vellozia declinans: 10.1016/0031-9422(92)80451-J
159071 - Zanthoxylum ailanthoides:
549434 - Zanthoxylum rhoifolium: 10.1016/0305-1978(92)90104-L
354530 - Zanthoxylum schinifolium: 10.5012/BKCS.2010.31.04.1081
33090 - 南沙参: -
33090 - 蒲公英: -

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

Xiangpei Wang, Mei Liu, Xiaofen Li, Mei Zhang, Feng Xu, Hongyun Liu, Hongmei Wu. Utilizing molecular docking and cell validation to explore the potential mechanisms of lupenone attenuating the inflammatory response via NF-κB pathway. Scientific reports. 2024 01; 14(1):625. doi: 10.1038/s41598-024-51150-3. [PMID: 38182871]
Hongmei Wu, Feng Xu, Xulong Huang, Xiaofen Li, Piao Yu, Lingling Zhang, Xiaosong Yang, Juan Kong, Cheng Zhen, Xiangpei Wang. Lupenone improves type 2 diabetic nephropathy by regulating NF-κB pathway-mediated inflammation and TGF-β1/Smad/CTGF-associated fibrosis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Sep; 118(?):154959. doi: 10.1016/j.phymed.2023.154959. [PMID: 37478684]
Sandip Debnath, Taha Alqahtani, Ali Alqahtani, Hanan M Alharbi, Shopnil Akash. Lupenone, a wonder chemical obtained from Euphorbia segetalis to boost affinity for the transcriptional factor escalating drought-tolerance in Solanum Lycopersicum: A cutting-edge computational biology approach. PloS one. 2023; 18(11):e0281293. doi: 10.1371/journal.pone.0281293. [PMID: 37939107]
Feng Xu, Mei Zhang, Hongmei Wu, Yuanmin Wang, Ye Yang, Xiangpei Wang. Study on the mechanism of lupenone for treating type 2 diabetes by integrating pharmacological evaluation and network pharmacology. Pharmaceutical biology. 2022 Dec; 60(1):997-1010. doi: 10.1080/13880209.2022.2067568. [PMID: 35635284]
Emanuelle M B M da Silva Landim, Ana Lúcia T G Ruiz, João E de Carvalho, Armando M Pomini, Lindamir H Pastorini, Silvana M Oliveira Santin. Antiproliferative activity and chemical constituents of Lonchocarpus cultratus (Fabaceae). Natural product research. 2021 Jun; 35(12):2056-2059. doi: 10.1080/14786419.2019.1647427. [PMID: 31401870]
Ashish Kumar, Vijai K Agnihotri. Phytochemical studies of Jurinea macrocephala roots from Western Himalaya. Natural product research. 2020 Feb; 34(3):421-424. doi: 10.1080/14786419.2018.1530233. [PMID: 30499332]
Lía S Valencia-Chan, Isabel García-Cámara, Luis W Torres-Tapia, Rosa E Moo-Puc, Sergio R Peraza-Sánchez. Lupane-Type Triterpenes of Phoradendron vernicosum. Journal of natural products. 2017 11; 80(11):3038-3042. doi: 10.1021/acs.jnatprod.7b00177. [PMID: 29120172]
Feng Xu, Hongmei Wu, Yuanmin Wang, Ye Yang, Yuan Gao, Xiangpei Wang. Determination of lupenone and β-sitosterol in Rhizoma Musae by UPLC with DAD and ELSD. Journal of chromatographic science. 2015 Nov; 53(10):1714-9. doi: 10.1093/chromsci/bmv079. [PMID: 26126840]
Oliver Callies, Luis M Bedoya, Manuela Beltrán, Alejandro Muñoz, Patricia Obregón Calderón, Alex A Osorio, Ignacio A Jiménez, José Alcamí, Isabel L Bazzocchi. Isolation, Structural Modification, and HIV Inhibition of Pentacyclic Lupane-Type Triterpenoids from Cassine xylocarpa and Maytenus cuzcoina. Journal of natural products. 2015 May; 78(5):1045-55. doi: 10.1021/np501025r. [PMID: 25927586]
Panawan Suttiarporn, Watcharapong Chumpolsri, Sugunya Mahatheeranont, Suwaporn Luangkamin, Somsuda Teepsawang, Vijittra Leardkamolkarn. Structures of phytosterols and triterpenoids with potential anti-cancer activity in bran of black non-glutinous rice. Nutrients. 2015 Mar; 7(3):1672-87. doi: 10.3390/nu7031672. [PMID: 25756784]
M Punnam Chander, K Vinod Kumar, A N Shriram, P Vijayachari. Anti-leptospiral activities of an endemic plant Glyptopetalum calocarpum (Kurz.) Prain used as a medicinal plant by Nicobarese of Andaman and Nicobar Islands. Natural product research. 2015; 29(16):1575-7. doi: 10.1080/14786419.2014.985679. [PMID: 25482276]
Feng Xu, Hongmei Wu, Xiangpei Wang, Ye Yang, Yuanmin Wang, Haibing Qian, Yanyan Zhang. RP-HPLC characterization of lupenone and β-sitosterol in rhizoma musae and evaluation of the anti-diabetic activity of lupenone in diabetic Sprague-Dawley rats. Molecules (Basel, Switzerland). 2014 Sep; 19(9):14114-27. doi: 10.3390/molecules190914114. [PMID: 25207716]
L M Ramadhan Al Muqarrabun, Norizan Ahmat, S Ruzaina S Aris, Nurdiana Shamsulrijal, Syarul N Baharum, Rafidah Ahmad, A Rifki Rosandy, M Nazip Suratman, H Takayama. A new sesquiterpenoid from Scaphium macropodum (Miq.) Beumee. Natural product research. 2014; 28(9):597-605. doi: 10.1080/14786419.2014.886211. [PMID: 24568340]
Eun-Kyung Ahn, Joa Sub Oh. Lupenone isolated from Adenophora triphylla var. japonica extract inhibits adipogenic differentiation through the downregulation of PPARγ in 3T3-L1 cells. Phytotherapy research : PTR. 2013 May; 27(5):761-6. doi: 10.1002/ptr.4779. [PMID: 22848028]
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