gamma-倒捻子素 | 31271-07-5

• 物质功能分类: 天然产物 - 氧杂蒽酮
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: gamma-倒捻子素
• 中文别名: R-倒捻子素；GAMMA-倒捻子；γ-倒捻子素；Γ-倒捻子；1,3,6,7-四羟基-2,8-双(3-甲基-2-丁烯基)-9H-占顿-9-酮；Gamma-倒捻子素
• 英文名称: γ-mangostin
• 英文别名: gamma-mangostin；normangostin；1,3,6,7-tetrahydroxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one；1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
• CAS: 31271-07-5
• 化学式: C₂₃H₂₄O₆
• 分子量: 396.44
• InChiKey: VEZXFTKZUMARDU-UHFFFAOYSA-N

物化性质

• 熔点：
  206-208 °C
• 沸点：
  648.4±55.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇：溶解度为为1mg/mL，无色至黄色
• LogP：
  5.744 (est)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2932999099
• 储存条件：
  2-8°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : gamma-Mangostin
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 31271-07-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C23H24O6
Molecular Weight : 396,43 g/mol
CAS-No. : 31271-07-5
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
gamma-Mangostin from Garcinia mangostana (mangosteen)
CAS-No. 31271-07-5 Acute Tox. 4; H302 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
gamma-Mangostin from Garcinia mangostana (mangosteen)
CAS-No. 31271-07-5 Xn, R22 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
Colour: yellow
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 207 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: ZD6122330
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H302 Harmful if swallowed.
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

生物活性

Gamma-Mangostin 是一种新颖的竞争性 5-HT2A 受体拮抗剂，从药用植物 Garcinia mangostana 的果壳中提纯。它也是一种运甲状腺素蛋白 (TTR) 原纤维化抑制剂，与甲状腺素 (T4) 结合位点结合并稳定了 TTR 四聚体。Gamma-Mangostin 可以抑制 [3H]-spiperone 与培养的大鼠主动脉心肌细胞的结合（IC50 = 3.5 nM），并且降低大鼠冠状动脉对 5-HT2A 的灌注压力反应（IC50 = 0.32 µM）。

靶点

• 5-羟色胺 2A (5-HT2A) 受体

化学性质

Gamma-Mangostin 可溶于甲醇、乙醇和 DMSO 等有机溶剂，来源于山竹壳。

用途

γ-倒捻子素具有抗炎、抗氧化、抗过敏和杀菌的作用。它可用于含量测定、鉴定以及药理实验等。

反应信息

• 作为反应物：
  描述：

  gamma-倒捻子素 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以96%的产率得到1,3,6,7-tetrahydroxy-2,8-bis(3-methyl-2-butyl)-9-xanthone
  参考文献：
  名称：

  山竹素类似物作为细胞毒剂的设计、合成和构效关系†

  摘要：

  为了更好地了解山竹素的构效关系，设计合成了一系列基于α-山竹素的呫吨酮衍生物。使用 MTT 分析评估了所有化合物对一组五种人类癌细胞系（HL-60、SMMC-7721、A-549、MCF-7 和 SW480）的细胞毒性。它们中的大多数显示出细胞毒性，最重要的是，化合物1a和2h对HL-60癌细胞系显示出最高的细胞毒性效力，IC 50值分别为5.96 μM和6.90 μM；化合物3e对SMMC-7221癌细胞系表现出最高的细胞毒效力，IC 50值为3.98 μM；化合物2e和2m分别对 HL-60 和 SMMC-7221 癌细胞系表现出比 α-mangostin 更低的细胞毒性但更高的选择性。构效关系分析表明，异戊烯基团在 C-8 上的维持对细胞毒活性至关重要。

  DOI：

  10.1039/c8ra08409b
• 作为产物：
  描述：

  α-倒捻子素 在 sodium hydride 、 乙硫醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以54%的产率得到gamma-倒捻子素
  参考文献：
  名称：

  作为磷酸甘油酸变位酶 1 抑制剂的 1,3,6,7-四羟基呫吨酮衍生物的设计、合成和生物学评价

  摘要：

  磷酸甘油酸变位酶 1 (PGAM1) 是癌症治疗的一个有希望的目标。在此，我们发现 α-mangostin 和 γ-mangostin 表现出中等的 PGAM1 抑制活性，IC 50 分别为 7.2 μM 和 1.2 μM。基于 α-芒果苷，设计、合成了一系列 1,3,6,7-四羟基呫吨酮衍生物，并在体外评估了其对 PGAM1 的抑制作用。还清楚地描述了这种新化合物的显着构效关系（SAR）和新的结合模式。该研究为进一步优化具有 1,3,6,7-四羟基呫吨酮骨架的 PGAM1 抑制剂或新型抑制剂的从头设计提供了有价值的信息。

  DOI：

  10.1016/j.bmcl.2021.127820

文献信息

• Synthesis and Antitumor Activities of &amp;#945;-,&amp;#947;-mangostin Derivatives
  作者：Kai Cheng、Gui-lin Zhang、Sheng-xiang Qiu、Yan-qing Liu、Yan-fei Wang、Song Liu、Yan Shan、Bo Yu、Yu Lu

  DOI：10.2174/1570180811666131217003216

  日期：2013.12.16

  isolated from Garcinia Mangostana L. as representative Xanthone's natural products of plant origin, revealed high activity of antitumor, antioxidation and other diverse pharmacological activities. A series of α, γ-Mangostin derivatives LT-1~17 has been synthesized, and confirmed by 1H NMR, 13C NMR, MS(supplement file). Compounds LT-2~17, as novel Xanthone, have been reported for the first time. Their antitumor

  α？-Mangostin和？-Mangostin主要从藤黄（Garcinia Mangostana L.）中分离出来，作为代表Xanthone的植物来源天然产物，具有很高的抗肿瘤，抗氧化和其他多种药理活性。合成了一系列α，γ，Mangostin衍生物LT-1〜17，并通过1 H NMR，13 C NMR，MS（补充文件）进行了确认。化合物LT-2〜17作为新型的黄酮，已被首次报道。已经通过MTT方法在细胞系：A549，K562，CNE，KB-3-1，MCF-7和HepG2中研究了它们的抗肿瘤活性。许多化合物显示出有效的抗肿瘤活性，在某些情况下甚至比Mangostins更高（更有效）。具有IC 50的化合物3A549细胞系中的1.73 µM值是两倍，比ADM（阿霉素）和α？，γ？-Mangostin活性更高，并且具有最强的抗肿瘤活性（IC 50 = 2.15 µM）。所有合成衍生物中的MCF
• 倒捻子素的全合成方法
  申请人：中国药科大学

  公开号：CN103864747B

  公开（公告）日：2016-06-22

  天然有效成分倒捻子素(mangostin)具有良好抗肿瘤活性、心血管活性、抗氧化、抗炎、抗菌等药理活性，本发明属于化学合成领域，具体涉及式(I)所示的倒捻子素的一种新合成方法。本发明以1，7-二羟基-3，6-二烷氧基-9H-呫吨酮为原料，通过亲核取代，克莱森重排，烃化，脱保护基等反应步骤制备α-mangostin、β-mangostin、β-mangostin-OMe和γ-mangostin，步骤简洁，适合工业化生产。
• 一种倒捻子素及其类似物的制备方法和用途
  申请人：南京美竹医药科技有限公司

  公开号：CN106554341B

  公开（公告）日：2019-05-21

  本发明属于创新药物和化妆品领域，具体涉及一种式(I)所示的倒捻子素(mangostin)以及式(II)所示的倒捻子素类似物的制备方法及其用途。本发明通过烯化反应及控制条件脱保护基，分别得到α‑，β‑和γ‑倒捻子素及其类似物。本方法制备产品纯度高，操作简便，产率高，成本低，适合大规模生产。β‑倒捻子素，γ‑倒捻子素，β‑甲氧基‑倒捻子素及其类似物，一方面具有紫外吸收能力和抗紫外线辐射作用，可单独作为防晒剂或者与其他防晒剂复配应用到化妆品中；另一方面，具有酸性鞘磷脂酶抑制活性，可作为酸性鞘磷脂酶抑制剂应用于制备预防和治疗与酸性鞘磷脂酶相关疾病的药物，主要涉及心脑血管疾病、神经系统疾病、肝疾病、肺疾病、自身免疫病、感染性疾病等。
• 一种磷酸甘油酸变位酶1抑制剂及其在相关疾病中的应用
  申请人：中国药科大学

  公开号：CN109053670A

  公开（公告）日：2018-12-21

  本发明属于药物化学领域，具体涉及磷酸甘油变位酶1。本发明提供了磷酸甘油变位酶1的抑制剂，具体结构为式I所示。本发明还提供了式I所示的合成方法及其在与细胞凋亡和肿瘤相关疾病中的应用，包括胃癌、肝癌、骨髓瘤、膀胱癌、前列腺癌、乳腺癌、直肠癌、头颈癌、肺癌、黑色素瘤、卵巢癌、宫颈癌、食道癌等各类癌症。
• Synthesis of xanthone derivatives based on α-mangostin and their biological evaluation for anti-cancer agents
  作者：Xiang Fei、Minmi Jo、Bit Lee、Sang-Bae Han、Kiho Lee、Jae-Kyung Jung、Seung-Yong Seo、Young-Shin Kwak

  DOI：10.1016/j.bmcl.2014.03.047

  日期：2014.5

  various parts of the mangosteen, Garcinia mangostana L. (Clusiaceae), a well-known tropical fruit. Novel xanthone derivatives based on α-mangostin were synthesized and evaluated as anti-cancer agents by cytotoxicity activity screening using 5 human cancer cell lines. Some of these analogs had potent to moderate inhibitory activities. The structure–activity relationship studies revealed that phenol groups

  呫吨酮衍生的天然产物，α倒捻子素从山竹的各个部分隔离，莽吉柿L.（藤黄科），公知的热带水果。合成了基于α-Mangostin的新型黄酮衍生物，并通过使用5种人类癌细胞系的细胞毒性活性筛选将其作为抗癌药进行了评估。这些类似物中的一些具有强至中等的抑制活性。结构与活性之间的关系研究表明，C3和C6上的酚基对于抗增殖活性至关重要，而C4修饰能够提高抗癌活性和类似药物的性能。我们的发现为进一步探索以提高效力提供了新的可能性。