Germacrene B
(Synonyms: 大根香叶烯B) 目录号 : GC49405A sesquiterpene
Cas No.:15423-57-1
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >90.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Germacrene B is a sesquiterpene that has been found in P. cablin (patchouli).1
1.Hasegawa, Y., Tajima, K., Toi, N., et al.An additional constituent occurring in the oil from a patchouli cultivarFlavour Fragr. J.7333-335(1992)
| Cas No. | 15423-57-1 | SDF | |
| 别名 | 大根香叶烯B | ||
| Canonical SMILES | C/C(C)=C1CC/C(C)=C/CC/C(C)=C/C/1 | ||
| 分子式 | C15H24 | 分子量 | 204.4 |
| 溶解度 | Chloroform: slightly soluble,Methanol: slightly soluble | 储存条件 | -20°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 4.8924 mL | 24.4618 mL | 48.9237 mL |
| 5 mM | 0.9785 mL | 4.8924 mL | 9.7847 mL |
| 10 mM | 0.4892 mL | 2.4462 mL | 4.8924 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Germacrene B - a central intermediate in sesquiterpene biosynthesis
Beilstein J Org Chem 2023 Feb 20;19:186-203.PMID:36865023DOI:10.3762/bjoc.19.18.
Germacranes are important intermediates in the biosynthesis of eudesmane and guaiane sesquiterpenes. After their initial formation from farnesyl diphosphate, these neutral intermediates can become reprotonated for a second cyclisation to reach the bicyclic eudesmane and guaiane skeletons. This review summarises the accumulated knowledge on eudesmane and guaiane sesquiterpene hydrocarbons and alcohols that potentially arise from the achiral sesquiterpene hydrocarbon Germacrene B. Not only compounds isolated from natural sources, but also synthetic compounds are dicussed, with the aim to give a rationale for the structural assignment for each compound. A total number of 64 compounds is presented, with 131 cited references.
Germacrene Analogs are Anti-androgenic on Androgen-dependent Cells
Nat Prod Commun 2016 Sep;11(9):1225-1228.PMID:30807005doi
Anti-androgenic drugs are treatments for androgen-related disorders such as benign prostatic hyperplasia, acne, hirsutism, and androgenic alopecia. Germacrone (1), a sesquiterpene isolated from hexane extracts of Curcuma aeruginosa Roxb. rhizome, is an androgen inhibitor of steroid 5-alpha reductase in- vitro. Here, we used the similarity of germacrone's ,t,B-unsaturated carbonyl to testosterone's α,β-unsaturated carbonyl to find germacrene analogs obtained from this plant and by semi-synthesis that might be more potent steroid 5-alpha reductase inhibitors. 8-Hydroxy Germacrene B (4) was -13-fold more potent than its parent, I and the most potent (ICso, 0.15 ± 0.022 mM) among 9 compounds tested. The conformation of its cyclodecadiene ring and the α,β-unsaturated ketone/hydroxy in the germacrene molecule might be crucial role for its anti-androgen activity. Moreover, I and 4 showed mild cytotoxic effect on prostate cancer cells. Neither compound was cytotoxic towards human dermal papilla cells at 100 μg/mL. We show that this SAR strategy created promising anti-androgenics for androgen dependent disorders and may create further analogues with further improvements in selectivity and clinical efficacy.
About the Chiral Stability of Germacrene B and the Biomimetic Synthesis of Guaiane Sesquiterpenes
J Org Chem 1997 Oct 17;62(21):7346-7350.PMID:11671850DOI:10.1021/jo970902r.
The planar chirality of 15-hydroxygermacrene B (2) has been examined by means of the asymmetric Sharpless epoxidation, performed as a kinetic resolution. (1)H NMR experiments with Eu(hfc)(3) demonstrate that the recovered 2 is racemic. Consequently, 2 and most likely also Germacrene B (1) are not enantiomerically stable at room temperature. The formation of the optically active cis-fused guaiane 4 of high ee with limited Sharpless reagent shows that the asymmetric epoxidation of 2 proceeds highly enantioselectively. The Sharpless epoxidation methodology applied on the (E,Z)-germacrane 3 results in the formation of the stable optically active epoxide 5. Acid-induced cyclization of 5, leading to a mixture of guaianes, probably proceeds via the trans-fused carbocationic intermediate A.
Germacrene C synthase from Lycopersicon esculentum cv. VFNT cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase
Proc Natl Acad Sci U S A 1998 Mar 3;95(5):2216-21.PMID:9482865DOI:10.1073/pnas.95.5.2216.
Germacrene C was found by GC-MS and NMR analysis to be the most abundant sesquiterpene in the leaf oil of Lycopersicon esculentum cv. VFNT Cherry, with lesser amounts of germacrene A, guaia-6,9-diene, Germacrene B, beta-caryophyllene, alpha-humulene, and germacrene D. Soluble enzyme preparations from leaves catalyzed the divalent metal ion-dependent cyclization of [1-3H]farnesyl diphosphate to these same sesquiterpene olefins, as determined by radio-GC. To obtain a germacrene synthase cDNA, a set of degenerate primers was constructed based on conserved amino acid sequences of related terpenoid cyclases. With cDNA prepared from leaf epidermis-enriched mRNA, these primers amplified a 767-bp fragment that was used as a hybridization probe to screen the cDNA library. Thirty-one clones were evaluated for functional expression of terpenoid cyclase activity in Escherichia coli by using labeled geranyl, farnesyl, and geranylgeranyl diphosphates as substrates. Nine cDNA isolates expressed sesquiterpene synthase activity, and GC-MS analysis of the products identified germacrene C with smaller amounts of germacrene A, B, and D. None of the expressed proteins was active with geranylgeranyl diphosphate; however, one truncated protein converted geranyl diphosphate to the monoterpene limonene. The cDNA inserts specify a deduced polypeptide of 548 amino acids (Mr = 64,114), and sequence comparison with other plant sesquiterpene cyclases indicates that germacrene C synthase most closely resembles cotton delta-cadinene synthase (50% identity).
Cloning, expression, purification and characterization of recombinant (+)-germacrene D synthase from Zingiber officinale
Arch Biochem Biophys 2006 Aug 1;452(1):17-28.PMID:16839518DOI:10.1016/j.abb.2006.06.007.
A cDNA clone encoding a sesquiterpene synthase, (+)-germacrene D synthase, has been isolated from ginger (Zingiber officinale). The full-length cDNA (AY860846) contains a 1650-bp open reading frame coding for 550 amino acids (63.8kDa) with a theoretical pI=5.59. The deduced amino acid sequence is 30-46% identical with sequences of other sesquiterpene synthases from angiosperms. The recombinant enzyme, produced in Escherichia coli, catalyzed the formation of a major product, (+)-germacrene D (50.2% of total sesquiterpenoids produced) and a co-product, Germacrene B (17.1%) and a number of minor by-products. The optimal pH for the recombinant enzyme is around 7.5. Substantial (+)-germacrene D synthase activity is observed in the presence of Mg2+, Mn2+, Ni2+ or Co2+, while the enzyme is inactive when Cu2+ or Zn2+ is used. The Km- and kcat-values are 0.88 microM and 3.34 x 10(-3) s(-1), respectively. A reaction mechanism involving a double 1,2-hydride shift has been established using deuterium labeled substrates in combination with GC-MS analysis.