2D Structure

3D Structure

Sitosterol


Properties
PID PID00137
Mol. Weight 414.718 g/mol
LogP 7.84
Water solubility 10 mg/mL
Hydrogen Bond Donor 1
Hydrogen Bond Acceptor 1
Rotatable Bonds 6
XLogP3-AA 9.3

Sitosterol

Identifiers
Formula C29H50O
PubChem CID 222284
FEMA -
Flavor Profile None
Smiles CC[C@@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C
InChl Key KZJWDPNRJALLNS-VJSFXXLFSA-N
InChl InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
CAS Registry Number 68555-08-8, 83-46-5
IUPAC Systematic Name (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets


Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)


Related Pungent TCM

English Name Pinyin Name (Chinese Name) Latin Name Properties in TCM merdians View Graph
Paniculate SwallowwortXu Chang Qing(徐长卿)Cynanchi Paniculati Radix Et RhizomaWarm, PungentLung, Spleen, StomachView Graph
Artemisia argyiAi Ye(艾叶)Argy Wormwood Leaf Equivalent plant: Artemisia monWarm,Pungent,BitterLung,Spleen,LiverView Graph
Croton tigliumBa Dou(巴豆)Pu rging CrotonHot,PungentLarge Intestine, StomachView Graph
Medicinal IndianmulberryBa Ji Tian(巴戟天)Morindae Officinalis RadixWarm, Pungent, SweetLung, Bladder, HeartView Graph
Rhizoma TyphoniiBai Fu Zi(白附子)rhizome of Giant TyphoniumWarm,Pungent,SweetSpleen,Liver,HeartView Graph
Cynanchum rootBai Qian(白前)Cynanchi Stauntonii Rhizoma Et RadixWarm, Pungent, BitterSpleen, LiverView Graph
Dahurian AngelicaBai Zhi(白芷)Angelicae Dahuricae RadixWarm, PungentLung, Spleen, StomachView Graph
Ternate PinelliaBan Xia(半夏)Pinellia ternataWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Barbed SkullcapBan Zhi Lian(半枝莲)Scutellariae Barbatae HerbaCold, Bitter, PungentBladder, Spleen, Liver,StomachView Graph
Piper cubebaBi Cheng Qie(荜澄茄)Cubeba PepperWarm, PungentLung, Spleen, StomachView Graph
Fructus Xanthii sibiriciCang Er Zi(苍耳子)fruit of Siberian CockleblurWarm,Pungent,BitterLung,Spleen,LiverView Graph
Chinese Angelica Equivalent plant: PhlojodicarpusDang Gui (当归)Angelicae Sinensis RadixWarm,Pungent,SweetSpleen,Liver,HeartView Graph
Clove TreeDing Xiang (丁香)Caryophylli FlosWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Doubleteeth Pubescent Angelica Equivalent plant: HDu Huo (独活)Angelicae Pubescentis RadixWarm, Pungent, BitterSpleen, LiverView Graph
Centipeda minimaE Bu Shi Cao(鹅不食草)Small CentipedaWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Divaricate SaposhnikoviaFang Feng (防风)Saposhnikoviae RadixWarm, Pungent, SweetLung, Bladder, HeartView Graph
Lemna minorFu Ping(浮萍)Common DuckwoodCold,PungentLung,BladderView Graph
Common Ginger Dried RhizomeGan Jiang (干姜)Zingiberis RhizomaHot, PungentLung, Spleen, Stomach, Heart, KidneyView Graph
Lesser GalangalGao Liang Jiang (高良姜)Alpiniae Officinarum RhizomaHot,PungentLarge Intestine, StomachView Graph
Cassiabarktree TwigGui Zhi (桂枝)Cinnamomi RamulusWarm, Pungent, SweetLung, Bladder, HeartView Graph
SafflowerHong Hua (红花)Carthami FlosWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Bunge Pricklyash Equivalent plant: Zanthoxylum schHua Jiao (花椒)Zanthoxyli PericarpiumWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Exocarpium Citri grandisHua Ju Hong(化橘红)Pummelo PeelMild,BitterLiverView Graph
Impatiens balsaminaJi Xing Zi(急性子)Garden Balsam SeedPungent,BitterLiver,HeartView Graph
Odoriferous RosewoodJiang Xiang (降香)Dalbergiae odoriferae LignumWarm, PungentLung, Spleen, StomachView Graph
Inula japonicaJin Fei Cao(金沸草)Japanese Inula Equivalent plant: Inula britannicaWarm,SaltyLung,Large Intestine,LiverView Graph
Wild Buckwheat RhizomeJin Qiao Mai(金荞麦)Fagopyri Dibotryis RhizomaCool, Pungent, AstringentLungView Graph
Fineleaf SchizonepetaJing Jie (荆芥)Schizonepetae HerbaMinor Warm, PungentLung, LiverView Graph
Tuber Onion SeedJiu Cai Zi (韭菜子)Allii Tuberosi SemenWarm, Sweet, PungentLiver, KidneyView Graph
Exocarpium Citri RubrumJu Hong (橘红)Citri Exocarpium RubrumWarm, Pungent, BitterSpleen, LiverView Graph
Common ColtsfootKuan Dong Hua(款冬花)Farfarae FlosWarm, Bitter, PungentLarge Intestine, StomachView Graph
Herba GlechomaeLian Qian Cao(连钱草)Longtube Ground Ivy HerbCold, Bitter, PungentBladder, Spleen, Liver,StomachView Graph
Radix ZanthoxyliLiang Mian Zhen(两面针)Shinyleaf Pricklyash RootMild,Pungent,BitterSpleen,HeartView Graph
Chinese Ephedra Equivalent plant: Ephedra equisetiMa Huang (麻黄)Ephedrae HerbaWarm, Pungent, Slightly BitterLung, BladderView Graph
Lasiosphaera fenzliiMa Bo(马勃)Bark-less Puff-ball Equivalent plant: Lycoperdon pMild,PungentLarge Intestine,LiverView Graph
Dahurian RhododendronMan Shan Hong (满山红)Rhododendri Daurici FoliumCold, Pungent, BitterLiver, Heart, LungView Graph
Catclaw Buttercup RootMao Zhua Cao (猫爪草)Ranunculi Ternati RadixWarm, Pungent, SweetLung, Bladder, HeartView Graph
MyrrhMo Yao (没药)MyrrhaNeutral, Pungent, BitterSpleen, Liver, Heart, KidneyView Graph
Great Burdock FruitNiu Bang Zi(牛蒡子)Arctii FructusCold, Bitter, PungentBladder, Spleen, Liver,StomachView Graph
Euphorbia lathyrisQian Jin Zi(千金子)Caper Euphorbia SeedWarm,PungentSpleen, Stomach, Kidney, LungView Graph
rhizome of Obscured HomalomenaQian Nian Jian(千年健)Homalomenae RhizomaWarm, Bitter, PungentSpleen, Large Intestine, Stomach, Gallbladder, Three EndView Graph
Common Hogfennel Equivalent plant: Peucedanum praQian Hu (前胡)Peucedani RadixCold, Bitter, PungentBladder, Spleen, Liver,StomachView Graph
Incised Notopterygium Equivalent plant: NotopteryQiang Huo(羌活)Notopterygii Rhizoma Et RadixWarm, Bitter, PungentSpleen, Large Intestine, Stomach, Gallbladder, Three EndView Graph
Gentiana macrophyllaQin Jiao(秦艽)Largeleaf Gentian Equivalent plant: Gentiana crasMinor cold,Pungent,BitterLung,Spleen,HeartView Graph
Sinomenium acutumQing Feng Teng(青风藤)OrientvineWarm,Pungent,BitterLung,Spleen,LiverView Graph
Common NutmegRou Dou Kou(肉豆蔻)Myristicae SemenWarm, PungentLung, Spleen, StomachView Graph
Sparganium stoloniferumSan Leng(三棱)Common BurreedMild,BitterLiverView Graph
Villous Amomum Equivalent plant: Amomum xanthioideSha Ren (砂仁)Amomi FructusWarm, PungentLung, Spleen, StomachView Graph
Asarum sagittarioidesShan Ci Gu(山慈菇)Arrowhead-like WildgingerNeural,Bitter,PungentLungView Graph
Cnidium monnieriShe Chuang Zi(蛇床子)Common CnidiumWarm,Pungent,BitterLung,Spleen,LiverView Graph
Fresh Common GingerSheng Jiang (生姜)Zingiber Rhizoma RecensWarm, PungentLung, Spleen, StomachView Graph
Arisaema consanguineumTian Nan Xing(天南星)Reddish Jackinthepulpit Equivalent plant: PinelliWarm,Pungent,BitterLung,Spleen,LiverView Graph
Lepidium apetalum [Syn. Lepidium micranthum ]Ting Li Zi(葶苈子)Pepperweed Seed Equivalent plant: Descurainia sopExtreme Cold,Pungent,BitterLung,BladderView Graph
Pseudolarix amabilisTu Jing Pi(土荆皮)Chinese Golden LarchWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Semen Cuseutae;Semen CuseutaeTu Si Zi(菟丝子)Dodder SeedMild,Pungent,SweetLung,Stomach,HeartView Graph
Chinese ClematisWei Ling Xian (威灵仙)Clematidis Radix Et RhizomaWarm, Pungent, SaltyBladderView Graph
Combined SpicebushWu Yao(乌药)Linderae RadixWarm, PungentLung, Spleen, StomachView Graph
Evodia rutaecarpaWu Zhu Yu(吴茱萸)Medicinal Evodia Equivalent plant: Evodia rutaecarPungent, bitter, hotLiver, spleen,stomachView Graph
Cacumen TamaricisXi He Liu(西河柳)Chinese Tamarisk TwigMild,Pungent,SweetLung,Stomach,HeartView Graph
Siegesbeckia orientalis L.Xi Lian Cao(豨莶草)SIEGESBECKIAE HERBACold, Bitter, PungentBladder, Spleen, Liver,StomachView Graph
Common SelfhealXia Ku Cao(夏枯草)Prunellae SpicaCold, Pungent, BitterLiver, Heart, LungView Graph
Curculigo orchioidesXian Mao(仙茅)Common CruculigoHot,PungentLarge Intestine, StomachView Graph
Nutgrass GalingaleXiang Fu (香附)Cyperi RhizomaNeutral, Pungent, Slightly Sweet, Slightly BitterSpleen, Liver, Three EndView Graph
Periploca sepiumXiang Jia Pi(香加皮)Chinese Silkvine Root-barkMinor Warm,Pungent,BitterLiver,Heart,KidneyView Graph
Haichow ElsholtziaXiang Ru (香薷)Moslae HerbaMinor Warm,PungentLung, Spleen, StomachView Graph
Wilson CitronXiang Yuan(香橼)Citri FructusWarm, Pungent, Sour, Slightly BitterLung, Spleen, LiverView Graph
Fennel FruitXiao Hui Xiang (小茴香)Foeniculi FructusWarm, PungentLung, Spleen, StomachView Graph
Allium macrostemonXie Bai(薤白)Longstamen Onion Equivalent plant: Allium chinenseWarm,Pungent,BitterLung,Spleen,LiverView Graph
Dipsacus japonicusXu Duan(续断)Japanese TeaselMinor Warm,Pungent,Sweet,BitterLiver,KidneyView Graph
Flos InulaeXuan Fu Hua(旋覆花)Inula FlowerMinor Warm,Pungent,Bitter,SaltyLung,StomachView Graph
Chrysanthemum indicumYe Ju Hua(野菊花)Indian Wild Chrysanthemum FlowerMinor cold,Pungent,BitterLung,Spleen,HeartView Graph
Virgate Wormwood HerbYin Chen(茵陈)Artemisiae Scopariae HerbaCold, Bitter, pungentBladder, Spleen, Liver,StomachView Graph
Aromatic TurmericYu Jin (郁金)Curcumae RadixCold, Pungent, BitterLiver, Heart, LungView Graph
Lycopus lucidusZe Lan(泽兰)Shiny BugleweedBitter, pungent,slightly warmLiver,spleenView Graph
Seville Ora nge Unripe Fruit Equivalent plant: PoZhi Ke(枳壳)Aurantii FructusCold, Sour, Bitter, PungentSpleen, StomachView Graph
Herba SarcatidraeZhong Jie Feng(肿节风)all-grass of Glabrous sarcandraNeural, Bitter, PungentLungView Graph
Radix Angelicae DecursivaeZi Hua Qian Hu(紫花前胡)Peucedani Decursivi RadixCold, Pungent, BitterLiver, Heart, LungView Graph
Perilia FruitZi Su Zi (紫苏子)Perillae FructusWarm, PungentLung, Spleen, StomachView Graph
Aster tataricusZi Wan(紫菀)Tatarion AsterWarm,Pungent,Sweet,BitterLungView Graph
Pueraria lobataGe Gen(葛根)Lobed Kudzuvine Root Equivalent plant: Pueraria thCool,Pungent,SweetSpleen,StomachView Graph

Pharmacological action

Beta-Sitosterol is one of several phytosterols (plant sterols) with chemical structures similar to that of cholesterol. Sitosterols are

white, waxy powders with a characteristic odor, and are one of the ingredients for E number E499. They are hydrophobic and soluble in alcohols.

Beta-Sitosterol is the major phytosterol while cholesteryl palmitate (CP) is the major CE in human diets in addition to free cholesterol.

Beta-Sitosterol, a plant sterol or phytosterol, has commercial uses in the nutraceutical and pharmaceutical industries.

Beta-Sitosterol (beta-sitosterol) is one of several phytosterols (plant sterols) with chemical structures similar to that of cholesterol.

Beta-Sitosterol is two major phytosterols generally present in plant cell membranes. Sitosterols are white, waxy powders with a characteristic odor, and are

one of the ingredients for E number E499. They are hydrophobic and soluble in alcohols.

Beta-sitosterol (SITO) is one of the most common dietary phytosterols in the blood. Beta-Sitosterol (BS) is the plant sterol that is most abundantly present in

plants and structurally similar to cholesterol, except in the addition of ethyl group. Beta-sitosterol is a cholesterol-like phytosterol, which widely

distributed in the plant kingdom. In addition, Beta-sitosterol was identified as the major principle compound responsible for the anticancer action of the plant.

Beta-Sitosterol (BS), a major bioactive constituent present in plants and vegetables has shown potent anticancer effect against many human cancer cells, but

the underlying mechanism remain elusive on NSCLC cancers.



Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.

References

1. https://en.wikipedia.org/wiki/Beta-Sitosterol

2. Ikeda I, Sugano M. Some aspects of mechanism of inhibition of cholesterol absorption by β-sitosterol[J]. Biochimica et Biophysica Acta (BBA)-Biomembranes, 1983, 732(3): 651-658.

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28. Awad, A. B., Chan, K. C., Downie, A. C., Fink, C. S. Peanuts as a source of β-sitosterol, a sterol with anticancer properties[J]. Nutrition and cancer, 2000, 36(2): 238-241.

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34. Cole, C., Burgoyne, T., Lee, A., Stehno-Bittel, L., Zaid, G. Arum Palaestinum with isovanillin, linolenic acid and β-sitosterol inhibits prostate cancer spheroids and reduces the growth rate of prostate tumors in mice[J]. BMC complementary and alternative medicine, 2015, 15(1): 264.

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36. Salen, G., Von Bergmann, K., Lütjohann, D. T., Kwiterovich, P., Kane, J., Patel, S. B., Multicenter Sitosterolemia Study Group Ezetimibe effectively reduces plasma plant sterols in patients with sitosterolemia[J]. Circulation, 2004, 109(8): 966-971.

37. Yamaguchi, J., Kawada-Watanabe, E., Koyanagi, R., Arashi, H., Sekiguchi, H., Nakao, K., Saito, K. Baseline serum sitosterol level as predictor of adverse clinical events in acute coronary syndrome patients with dyslipidaemia: a sub-analysis of HIJ-PROPER[J]. Atherosclerosis, 2018, 274: 139-145.

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39. Pradhan, M., Suri, C., Choudhary, S., Naik, P. K., Lopus, M. Elucidation of the anticancer potential and tubulin isotype-specific interactions of β-sitosterol[J]. Journal of Biomolecular Structure and Dynamics, 2018, 36(1): 195-208.

40. Rajavel, T., Mohankumar, R., Archunan, G., Ruckmani, K., Devi, K. P. Beta sitosterol and Daucosterol (phytosterols identified in Grewia tiliaefolia) perturbs cell cycle and induces apoptotic cell death in A549 cells[J]. Scientific reports, 2017, 7(1): 3418.

41. Moon, D. O., Kim, M. O., Choi, Y. H., Kim, G. Y. β-Sitosterol induces G2/M arrest, endoreduplication, and apoptosis through the Bcl-2 and PI3K/Akt signaling pathways[J]. Cancer letters, 2008, 264(2): 181-191.

42. Berges, R. R., Windeler, J., Trampisch, H. J., Senge, T. H., β-Sitosterol Study Group. Randomised, placebo-controlled, double-blind clinical trial of β-sitosterol in patients with benign prostatic hyperplasia[J]. The Lancet, 1995, 345(8964): 1529-1532.

43. Berges R R, Kassen A, Senge T. Treatment of symptomatic benign prostatic hyperplasia with β‐sitosterol: an 18‐month follow‐up[J]. BJU international, 2000, 85(7): 842-846.

44. Bouic, P. J. D., Etsebeth, S., Liebenberg, R. W., Albrecht, C. F., Pegel, K., Van Jaarsveld, P. P. Beta-sitosterol and beta-sitosterol glucoside stimulate human peripheral blood lymphocyte proliferation: Implications for their use as an immunomodulatory vitamin combination[J]. International journal of immunopharmacology, 1996, 18(12): 693-700.

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