기본 정보
- CAS
17406-45-0- 표준 SMILES
C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C- InChIKey
REJLGAUYTKNVJM-SGXCCWNXSA-N- 분자식
- C50H83NO21
- 평균 분자량
- 1,034.2 g/mol
- 단동위원소 질량
- 1,033.54575866
개요
Tomatine is a steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose. It has a role as an antifungal agent, a phytotoxin and an immunological adjuvant. It is a glycoalkaloid, a glycoside, a steroid alkaloid, a tetrasaccharide derivative and an alkaloid antibiotic. It is functionally related to a tomatidine.
이름 및 식별자
- 우선 이름
- Tomatine
- IUPAC
- (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
- 영어명
- TOMATINE
- 분자식
- C50H83NO21
- 분자량
- 1034.19
이름 및 동의어
TomatineLycopersicinalpha-Tomatine17406-45-0TomatinA''-TomatidineTomatidine, glycosideDTXSID5040413CHEBI:9630NSC-23444031U6547O08DTXCID3020413
이름 더 보기
Tomatine [for Cholesterol assay]omatineTomatieNSC 9223a-TomatineNSC 234440LYOCPERSICIN
NSC-9223beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-xylopyranosyl-(1-3))-O-beta-D-glucopyranosyl-(1-4)-(22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1-2)-[beta-D-xylopyranosyl-(1-3)]-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranoside(22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1-2)-(beta-D-xylopyranosyl-(1-3))-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranosideRefChem:1903612-(2-(4,5-dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-piperidine)-16-yl)oxyoxan-3-yl)oxy-5-hydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol241-429-5(2S,3R,4S,5S,6R)-2-((2S,3R,4S,5R,6R)-2-((2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-((1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-piperidine)-16-yl)oxyoxan-3-yl)oxy-5-hydroxy-6-(hydroxymethyl)-4-((2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl)oxyoxan-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
데이터베이스 식별자
- CAS
17406-45-0- PubChem CID
- 28523
- DTXSID
DTXSID5040413- ChEMBL
CHEMBL525778- ChEBI
CHEBI:9630- UNII
- 31U6547O08
- EC Number
- 241-429-5
- Nikkaji
- J9.099I
물성
구조 계산 물성
- XLogP
- -0.7
- 극성 표면적
- 338 Ų
- 수소 결합 공여자 수
- 13
- 수소 결합 수용자 수
- 22
- 회전 가능 결합 수
- 11
- 무거운 원자 수
- 72
- 형식 전하
- 0
- 복잡도
- 1,840
실험 및 물리화학적 성질
Chemical ClassesBiological Agents -> Plant Toxins
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Solanidines and alkaloid derivatives [ST0115]
Color/Form
NEEDLES FROM METHANOL
WHITE CRYSTALS
SolubilitySOLUBLE IN ETHANOL, METHANOL, DIOXANE, PROPYLENE GLYCOL; PRACTICALLY INSOLUBLE IN WATER, ETHER, PETROLEUM ETHER
Melting Point263-268 °C
Optical Rotation
SPECIFIC OPTICAL ROTATION: -18 DEG @ 22 °C/D (C= 0.55 IN PYRIDINE)
SPECIFIC OPTICAL ROTATION: -30 DEG @ 20 °C/D (PYRIDINE)
Physical DescriptionWhite solid; [HSDB] Faintly beige powder; [MSDSonline]
Collision Cross Section311.78 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 300 · 300-305°C
- 끓는 점
- 806.69 °C · 806.69°C (rough estimate)
- 밀도
- 1.48 · 1.48±0.1 g/cm3 (20 ºC 760 Torr)
- 굴절률
- 1.528 · 1.5280 (estimate)
- 저장 조건
- 2 · 2-8°C
- 용해도
- DMSO(약간 용해됨), 메탄올(약간 용해됨, 가열), 피리딘(약간 용해됨)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 12.77 · 12.77±0.70(Predicted)
- 색상
- 흰색에서 황백색까지
- Merck
- 14 · 14,9545
- InChIKey
- REJLGAUYTKNVJM-GXOLHJPNNA-N
- LogP
- 2.22 · 2.220 (est)
화학적 성질
Faintly beige powder
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 1 notifications to the ECHA C&L Inventory.
유해성 정보
Regulatory Information
.beta.-D-Galactopyranoside, (3.beta.,5.alpha.,22.beta.,25S)-spirosolan-3-yl O-.beta.-D-glucopyranosyl-(1â2)-O-[.beta.-D-xylopyranosyl-(1â3)]-O-.beta.-D-glucopyranosyl-(1â4)-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryHas demonstrated growth inhibition of some fungi and bacteria; [Merck Index] Emergency treatment: Irritants; [HSDB] May cause irritation; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (100%)
독성 정보
InteractionsTOMATINE REDUCED THE GROWTH ENHANCED BY 10-4 MOLAR INDOLE-3-ACETIC ACID.
Natural Pollution SourcesOCCURS IN THE EXTRACT OF LEAVES OF WILD TOMATO PLANTS.
Non-Human Toxicity Excerpts
...IRRITANT PROPERTIES /OF TOMATINE/ HAVE BEEN EVALUATED IN RABBITS BY APPLYING A 5% OINTMENT TO THE EYE. IT PROVED TO BE IRRITATING, AND ON REPEATED APPLICATION AFFECTED PARTICULARLY THE CONJUNCTIVA OF THE LIDS, MAKING THE LIDS EDEMATOUS. HOWEVER, THE EYES RECOVERED COMPLETELY A FEW DAYS AFTER EXPOSURE WAS DISCONTINUED.
TOMATINE FORMED A COMPLEX WITH CHOLESTEROL IN VIVO IN RAT INTESTINE. TOMATINE (1% IN DIET) DECREASED THE UPTAKE OF DIETARY CHOLESTEROL BY THE LIVERS AND INCREASED THE RATES OF HEPATIC AND INTESTINAL CHOLESTEROL SYNTHESIS AND THE STEROL EXCRETION WITHOUT AFFECTING THE BILE ACID SECRETION.
AFTER ADDITION OF TOMATINE (40 MUG/ML) TO THE BEATING HEART CELL CULTURE MEDIUM, THE CELLS CEASED BEATING WITHIN A FEW MINUTES. AT A CONCENTRATION OF 20 MUG/ML, TOMATINE CAUSED A PRONOUNCED INCREASE OF THE CONTRACTION FREQUENCY, LASTING FOR AT LEAST 2 HOURS.
ALPHA-TOMATINE DID NOT INHIBIT RESPIRATION BY MITOCHONDRIA FROM ISOLATED MUNG BEAN SHOOTS, BUT GRADUALLY INHIBITED RESPIRATION BY THE SHOOTS THEMSELVES. PHOTOSYSTEM II OF SPINACH CHLOROPLASTS WAS INHIBITED BY ALPHA-TOMATINE AT A CONCENTRATION OF 10-5 MOLAR, PH 8, AND AN INCUBATION TEMPERATURE OF 25 °C.
THE STEREOISOMERIC GLYCOSIDIC ALKALOID TOMATINE IS TOXIC AT 10 AND 25 PPM TO LYMNAEA CUBENSIS AND BIOMPHALARIA GLABRATUS.
안전 데이터
- rtecs
- XW1050000
- ridadr
- 1544
- 독성
- LD orally in rats: 900-1000 mg/kg (Wilson)
- HS 번호
- 29329990
- risk_code
- 23/25-22
- hazard_code
- Xn
- safety_code
- 45-24/25-22
- 유해 물질 데이터
- 17406-45-0(Hazardous Substances Data)
화학 및 산업
약리 정보
Mechanism of Action
SIX GLYCOALKALOIDS AND ONE AGLYCONE WERE TESTED FOR CARDIOTONIC ACTIVITIES AND COMPARED WITH K-STROPHANTHOSIDE BY USE OF THE ISOLATED FROG HEART. THE DECREASING ORDER OF POTENCY WAS AS FOLLOWS: K-STROPHANTHOSIDE GREATER THAN TOMATINE GREATER THAN ALPHA-CHACONINE EQUAL TO ALPHA-SOLANINE GREATER THAN DEMISSINE EQUAL TO COMMERSONINE GREATER THAN BETA-CHACONINE GREATER THAN SOLANIDINE. CARDIOTONIC ACTIVITY WAS DIRECTLY RELATED TO THE NUMBER OF SUGARS IN THE MOLECULE IN WHICH THE GLYCOALKALOIDS HAD A COMMON AGLYCONE.
REMOVAL OF 1 OR MORE SUGAR RESIDUES FROM THE ALPHA-TOMATINE MOLECULE MARKEDLY DECREASED ITS FUNGITOXICITY. ALTHOUGH THE PARTIAL HYDROLYSIS OF ALPHA-TOMATINE DID NOT GREATLY AFFECT ITS SURFACTANT PROPERTIES, IT DID DESTROY THE ABILITY OF THE ALKALOID TO FORM A COMPLEX WITH CHOLESTEROL.
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
용도 및 제조
Uses
Extracted from leaves of wild tomato plants; [Merck Index] Used as precipitating agent for steroids, a plant fungicide, and a therapeutic antifungal and anti-infective agent; [HSDB]
Farming (Pesticides) [Category: Industry]
MEDICATION
PRECIPITATING AGENT FOR STEROIDS; PROPOSED AS AN ALTERNATE PRECIPITANT TO DIGITONIN
USED AS PLANT FUNGICIDE AND AS A SPECIFIC PRECIPITATING AGENT FOR CHOLESTEROL
Methods of ManufacturingA GLYCOSIDAL ALKALOID PREPARED FROM THE DRIED LEAVES AND STEMS OF THE TOMATO PLANT. ... THE CRUDE EXTRACT IS REFERRED TO AS TOMATIN.
General Manufacturing Information
HAS BEEN FOUND TO INHIBIT THE GROWTH OF VARIOUS FUNGI AND BACTERIA.
YIELDS ON PARTIAL HYDROLYSIS, BESIDES ALPHA-TOMATINE, THE MAIN CONSTITUENT, BETA1-, BETA2-, GAMMA-, AND DELTA-TOMATINE... ALPHA-TOMATINE CONSISTS OF ONE MOL TOMATIDINE LINKED TO A TETRASACCHARIDE COMPOSED OF 2 MOLS D-GLUCOSE, 1 MOL D-XYLOSE AND 1 MOL D-GALACTOSE...
STABLE TO STRONG ALKALI BUT HYDROLYZED BY ACIDS TO PRODUCE CRYSTALLINE TOMATIDINE AND A SOLUTION RICH IN REDUCING SUGARS.
응용 분야
개요This glycosidic alkaloid has been obtained from the dried leaves of Lycopersicum pimpinelli/olium (Syn. Solanum racemigerum) and also occurs in L. esculentum; L. hirsutum; L. peruvianum; L. peruvianum var. chutatum and L. putatum. The alkaloid forms colourless needles from MeOH and has a somewhat indefinite melting point about 270°C. It is laevorotatory with [α]20D - 30° (pyridine) and on hydrolysis with H2S04 yields tomatidine, I mole of galactose, 2 moles of glucose and 1 mole of xylose. The tetrasaccharide unit is known as lycotetraose. Partial hydrolysis with acid yields a series of products depending upon which, and how many, of the sugar residues are split off from the molecule. Those which have been isolated are: tomatidine lycotriose I (galactose-glucose-glucose); tomatidine lycotriose II (galactose-glucose-xylose); tomatidine lycobiose (galactose-glucose) and tomatidine-galactose.
용도Tomatine is used as an antiproliferatice agent used in the suppression of breast adenocarcinoma cells.
상·하류 제품 정보
하류 제품
공급사100 곳
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추가 설명
정의ChEBI: A steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galac ose.
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