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ソラニダ-5-エン-3β-イル2-O,4-O-ジ(6-デオキシ-α-L-マンノピラノシル)-β-D-グルコピラノシド

Alpha-Chaconine

HCID 442971
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
20562-03-2
標準SMILES
C[C@H]1CC[C@@H]2[C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)CC[C@]6(C)[C@H]5CC[C@]34C)N2C1
InChIKey
TYNQWWGVEGFKRU-AJDPQWBVSA-N
分子式
C45H73NO14
平均分子量
852.1 g/mol
単同位体質量
851.503106

概要

Alpha-Chaconine is a glycoalkaloid and a steroid saponin.

名称と識別子

優先名称
Alpha-Chaconine
IUPAC
(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
現地名
ソラニダ-5-エン-3β-イル2-O,4-O-ジ(6-デオキシ-α-L-マンノピラノシル)-β-D-グルコピラノシド
英語名
α-Chaconine
分子式
C45H73NO14
分子量
852.06

名称と別名

alpha-Chaconine20562-03-25QOL0LIM81DTXSID501016601(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol(2S,3R,4R,5R,6S)-2-((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triolRefChem:111118DTXCID301474794(2S,3R,4R,5R,6S)-2-((2R,3R,4S,5S,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol

物性

構造計算による物性

XLogP
1.8
極性表面積
220 Ų
水素結合供与体数
8
水素結合受容体数
15
回転可能結合数
7
重原子数
60
形式電荷
0
複雑度
1,570

実験および物理化学的性質

LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Solanidines and alkaloid derivatives [ST0115]

物理化学的性質

融点
228 · 228-236 °C
比重(密度)
1.37 · 1.37±0.1 g/cm3(Predicted)
貯蔵温度
20 °C · −20°C
溶解性
10 mg/mL、透明、微黄色 · ピリジン: 10 mg/mL、透明、微黄色
外見
個体
酸解離定数(Pka)
12 · 12+-.0.70(Predicted)
色
ホワイトからオフホワイト
安定性
吸湿性
LogP
8.5 · 8.500 (est)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Warning

H361 (95.2%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazard Classes and CategoriesRepr. 2 (95.2%)

毒性情報

Toxicity Summary · 2 件

The European Commission asked EFSA for a scientific opinion on the risks for animal and human health related to the presence of glycoalkaloids (GAs) in feed and food. Their risk assessment covers edible parts of potato plants and other food plants containing GAs, in particular, tomato and aubergine. The acute toxic effects of potato GAs (α-solanine and α-chaconine) in humans include gastrointestinal symptoms such as nausea, vomiting and diarrhoea. In humans, no evidence of health problems associated with repeated or long-term intake of GAs via potatoes has been identified. For tomato and aubergine GAs, the risk to human health could not be characterised due to the lack of occurrence data and the limited toxicity data. For horses, farm and companion animals, no risk characterisation for potato GAs could be performed due to insufficient data on occurrence in feed and on potential adverse effects of GAs in these species.

Alpha-Chaconine has inhibitory effect on lung adenocarcinoma cell metastasis in vitro. Alpha-chaconine could inhibit phosphorylation of c-Jun N-terminal kinase (JNK) and Akt, whereas it did not affected phosphorylation of extracellular signal regulating kinase (ERK) and p38. In addition, alpha-chaconine significantly decreased the nuclear level of nuclear factor kappa B (NF-_B) and the binding ability of NF-_B. Therefore, alpha-chaconine inhibited A549 cell metastasis by a reduction of matrix metalloproteinase-2 (MMP-2) and matrix metalloproteinase-9 (MMP-9) activities involving suppression of phosphoinositide 3-kinase/Akt/NF-_B (PI3K/Akt/NF-_B) signaling pathway. Alpha-chaconine has exhibited its antiproliferative and apoptotic effects on the growth of cancer cells originating from human skin, liver, prostate, breast, and colon. In addition to the cytotoxicity in various cancer cells, R-chaconine induces significant cytotoxicity in Chang, normal human liver cells. (A15417)

化学と産業

薬理情報

Mechanism of Action · 1 件

The adverse effects of glycoalkaloids (GAs) may be due to their ability to complex with membrane 3β‐hydroxy sterols, thereby causing disruption and loss of integrity of cell membranes. After oral exposure, these effects may affect the mucosa of the gastrointestinal tract and cause the symptoms observed in intoxicated humans such as nausea, vomiting and diarrhoea. GAs inhibit acetylcholinesterase (AChE) and serum butyrylcholinesterase (BuChE) by a reversible, competitive mode of action. The relative potency of inhibition of α‐solanine and α‐chaconine appears to be similar. The aglycones exert weak or no inhibitory effects. The excess of acetylcholine at the neuronal and neuromuscular junctions upon inhibition of the enzymes might also contribute to the symptoms shown for intoxications with GAs.

Absorption, Distribution and Excretion · 2 件

Chaconine was poorly absorbed from the gastrointestinal tract and rapidly excreted in feces when administered orally to rats. Intraperitoneal administration of low doses resulted in urinary and fecal excretion of metabolites, and probably involved biliary excretion. High intraperitoneal doses depressed fecal and urinary elimination, and resulted in accumulation in various tissues. The major metabolite appeared to be the aglycone, solanidine. Alpha-chaconine is very similar to alpha-solanine in its elimination and distribution in rats.

The potato glycoalkaloids (GAs), α‐solanine and α‐chaconine, show a relatively low oral bioavailability, with differences between species. Hamsters exhibit higher absorption and slower excretion rates for both substances compared to rats. The metabolic profiles of potato GAs in experimental animals could not be characterised due to the limited information. In humans, α‐solanine and α‐chaconine are systemically absorbed following ingestion, and relatively long serum half‐lives were reported. The blood clearance of the respective aglycone solanidine appears to be slow, and levels of solanidine were regularly detected in the blood of human volunteers. This suggests hydrolysis of GAs. No further information is available on metabolism and excretion of potato GAs in humans.

用途と製造

Uses · 2 件

関連反応

0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
2-((4-hydroxy-2-(hydroxymethyl)-6-((10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)oxan-3-yl)oxy)-6-methyloxane-3,4,5-triol
633-788-5
Conine
名称をさらに表示
α-カコニン[ソラニダ-5-エン-3β-イル]2-O-(6-デオキシ-α-L-マンノピラノシル)-4-O-(6-デオキシ-α-L-マンノピラノシル)-β-D-グルコピラノシドソラニダ-5-エン-3β-イル2-O,4-O-ジ(6-デオキシ-α-L-マンノピラノシル)-β-D-グルコピラノシドα-チャコニンカコニンΑ‐チャコニンカコニン, Α-(2S,3R,4R,5R,6S)-2-{[(2R,3S,4S,5R,6R)-4-ヒドロキシ-2-(ヒドロキシメチル)-6-{[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-テトラメチル-22-アザヘキサシクロ[12.10.0.02,11.05,10.015,23.017,22]テトラコサ-4-エン-7-イル]オキシ}-5-{[(2S,3R,4R,5R,6S)-3,4,5-トリヒドロキシ-6-メチルオキサン-2-イル]オキシ}オキサン-3-イル]オキシ}-6-メチルオキサン-3,4,5-トリオールα-ChaconineCHACONINE, A-ALPA-CHACONINEalpha-Chaconinα-Chaconine-RMALPHA-CHACOCINECHACONINE, ALPHA-
Chaconinea-Chaconinealpha-?ChaconineMFCD09039102.alpha.-Chaconine(3b)-Solanid-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1-2)-O-(6-deoxy-a-L-mannopyranosyl-(1-4))-b-D-glucopyranosideUNII-5QOL0LIM81CCRIS 6509

データベース識別子

CAS
20562-03-2
PubChem CID
442971
DTXSID
DTXSID501016601
ChEMBL
CHEMBL2288884
ChEBI
CHEBI:10219
UNII
5QOL0LIM81
EC Number
633-788-5
Nikkaji
J15.746E
EFSA Substance CharacterizationOpenFoodTox Output ID 3680
Human Toxicity Excerpts · 1 件

Seventy-eight schoolboys became ill after eating potato at lunch, and seventeen required admission to hospital. The gastrointestinal, circulatory, neurological and dermatological findings and the results of laboratory investigations were consistent with solanine poisoning. Junior boys and all the monitors were affected; however, no senior boys or staff were affected. This pattern was compatible with the consumption of a relatively small number of toxic potatoes believed to have come from a single bag. The amount of solanine in potato waste recovered after the meal was excessive as assessed by its anticholinesterase activity. The amount of alpha-solanine and alpha-chaconine in the flesh and peel of potatoes from another bag known to have been left from the previous school term was high. The narrow margin between the solanidine content for normal and toxic potatoes might esult from an excessive synthesis by the latter of additional related steroids that might enhance the toxicity of solanidine.

Environmental BiodegradationThe potato glycoalkaloids alpha-chaconine and alpha-solanine are produced in high amounts in potato plants. Degradation of the compounds in groundwater was primarily microbial and the glycoalkaloids were degraded within 21-42 days.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

F
10
wgk
3
rtecs
FL6700000
ridadr
1544
risk_code
63
hazard_code
Xn
safety_code
22-36/37
hazard_class
6.1(b)
packing_group
III

Solanacea plants, which include tomatoes, potatoes, and eggplants, contain natural glycoalkaloid toxins called solanines and chaconine. While the glycoalkaloid levels are generally low, higher concentrations are found in potato sprouts and bitter-tasting peel and green parts, and in green tomatoes. The plants produce these toxins in response to stresses like bruising, UV light, microorganisms and attacks from insect pests and herbivores. To reduce the production of solanines and chaconine it is important to store potatoes in a dark, cool and dry place, and not to eat green or sprouting parts.

alpha-Chaconine is found in potato.

Use ClassificationFood Contaminant -> NATURALLY_OCCURRING_TOXICANT -> JECFA Functional Classes

応用分野

使用α-Chaconine is a glycoalkaloid displaying nerve toxin activity. Potential antifungal activity.

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