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Home > A new indole-type alkaloid from the roots of Clematis florida var. plena
A new indole-type alkaloid from the roots of Clematis florida var. plena
Kai-Hui Sun, Xin-Hua Ma, Xian-Ming Zeng, Zhong-Yue Lin, Yu-Mei Cai, Hai-Tao
Zhang, Xiao-Yan Lin, Shi-Biao Feng, Tian-Hua Zhong & Yong-Hong Zhang
To cite this article: Kai-Hui Sun, Xin-Hua Ma, Xian-Ming Zeng, Zhong-Yue Lin, Yu-Mei Cai, HaiTao Zhang, Xiao-Yan Lin, Shi-Biao Feng, Tian-Hua Zhong & Yong-Hong Zhang (2019) A new
indole-type alkaloid from the roots of Clematisfloridavar.plena, Natural Product Research, 33:20,
2925-2931, DOI: 10.1080/14786419.2018.1510396
To link to this article: https://doi.org/10.1080/14786419.2018.1510396
1. Introduction
Clematis florida Thunb. var. plena D. Don is a perennial herbal plant belonging to the family Ranunculaceae and the genus Clematis and is a variety of Clematis florida Thunb. (Editorial Committee of Flora of China 1980). This variety has long been used as a folk remedy named Shiershichen in She Ethnopharmacy, and is widely distributed in southeast China. The roots and rhizomes of C. florida var. plena were popularly used as an anti-inflammatory, anti-rheumatism and analgesic agent in She Ethnopharmacy in Fujian Province, China (Huang et al. 2013). Chemical investigations of this genus afforded triterpene saponins (Zhao et al. 2016), alkaloids (Li et al. 2013), flavonoids (Chang et al. 2017), lignans (Xiong et al. 2014), coumarins (Xiong et al. 2014), macrocyclic compounds (Qiu et al. 2017), and phenolic glycosides (Zhang et al. 2015). In order to search for anti-inflammatory active ingredients, we have performed systematically chemical and pharmacological investigations of C. florida var. plena. Here we
report the isolation and structural elucidation of one new indole alkaliod (1), together with three known analogues (2–4), one aromatic acid (5) and five known triterpene saponins (6–10) given in Figure 1, as well as the anti-inflammatory activities of the extracted fraction and isolated compounds.
2. Results and discussion
Compound 1 was obtained as a light brown gummy material. The positive-ion HRESIMS (Figure S1, supplementary material) showed the molecular ion [M þ Na]þ at m/z 522.1576, corresponding to the formula C22H29NO12. Its IR spectrum showed the absorption of ester carbonyl group at 1695 cm1 and aromatic ring absorptions at 1529 cm1. The 1 H NMR spectrum (Figure S2, supplementary material) indicated the presence of an ABX system of protons at dH 7.86 (1 H, d, J ¼ 8.8 Hz), 6.76 (1 H, dd, J ¼ 2.2, 8.8 Hz), 6.87 (1 H, d, J ¼ 2.2 Hz), a singlet aromatic proton at dH 7.87 (1 H, s) and a methoxy group at dH 3.73 (3 H, s) (Table S1, supplementary material). Its 13C NMR spectrum exhibited eight aromatic carbons and an ester carbonyl carbon (dC 165.5) (Figure S3 and Table S1, supplementary material). All investigations suggested that compound 1 had a similar indole molecular skeleton to compound 4, however, an ester methoxy group in 4 was found to be replaced by two hexoses in 1. The two anomeric protons arising from the sugar moieties appeared at dH 5.60 (1 H, d, J ¼ 7. 8 Hz) and 4.63 (1 H, d, J ¼ 1.6 Hz), which correlated respectively with signals at dC 95.2 and 102.2 ppm in the 1 H-13C HSQC spectrum (Figure S4, supplementary material). The spin systems associated with monosaccharides were identified by a 1 H-13C HSQC experiment with the aid of 1 H-1 H COSY spectra (Figure S6, supplementary material). In the 1 H-13C HMBC spectrum (Figure S5, supplementary material), the anomeric proton at dH 5.60 showed long-range correlation with the carbon at dC 165.5 (C-10), suggesting the attachment of the glucosyl moiety at C-10. The anomeric proton at dH 4.63 indicated interaction with the carbon at dC 67.8 (C-6 of the glucose) confirming that the rhamnosyl unit was linked to C-6 of the glucosyl unit. The 1 H-13C HMBC and 1 H-1 H COSY correlations are shown in Figure S7, supplementary material. The sugars were confirmed by acid hydrolysis and comparison with authentic sugars on TLC.
Consequently, the structure of 1 was elucidated as a-L-rhamnopyranosyl-(1!6)-b-Dglucopyranosyl 6-methoxy-3-indolecarbonate. By comparing the physical and spectral data with the literature data, 9 known compounds (2–10) were identified as: a-L-rhamnopyranosyl-(1!6)-b-D- glucopyranosyl- 3-indolecarbonate (2) (Shi et al. 2006), methyl 6-O-a-L- rhamnopyranosyl -(1!6)-a-Dglucopyranosyl 3 indolecarbonate (3) (Shi et al. 2006), methyl 6-methoxy-3-indolecarbonate (4) (Shi et al. 2006), Trans-isoferulic acid (5) (Prachayasittikul et al. 2009), 3-O-b-D-ribopyranosyl-(1!3)-a-L-rhamnopyranosyl - (1!2) -[b-D-glucopyranosyl-(1!4)]-a-L-arabinopyranosyl oleanolic acid 28-O-a-L-rhamnopyranosyl-(1!4)-b-D-glucopyranosyl-(1!6)-b-D-glucopyranoside (6) (Zhao et al. 2014), Tomentoside A (7) (Wang et al. 2013), Huzhangoside C (8) (Kizu et al. 1995), Clematangoticoside B (9) (Zhao et al. 2016), Huzhangoside B (10) (Kizu et al. 1995), respectively. All compounds were isolated from C. florida var. plena for the first time. The 1H and 13C spectral data of the isolated compounds (1–10) are given in Table S1 and Table S2.
In order to identify the biological activity, an in vivo anti-inflammatory model was used, the results showed that the n-butanol extract of the plant exhibited potent anti-inflammatory activity against ear edema in vivo, with inhibition rate of 48.7% at a dose of 800 mg/kg (as shown in Table S3). The n-butanol subfraction (Fr. B4) exhibited potent anti-inflammatory activity with inhibition rate of 47.6% at a dose of 600 mg/kg. Furthermore, the results showed that compounds 8–9 (triterpene saponins) obtained from the n-butanol subfractions (Fr. B4) displayed significant anti-inflammatory activity with inhibition rate of 50.9% and 54.7% at a dose of 200 mg/kg. However, compound 1 (alkaloid) exhibited weak anti-inflammatory activity with inhibition rate of 27.0% at a dose of 200 mg/kg.
3. Experimental
3.1. General experimental procedures
Column chromatography (CC): silica gel 60 (SiO2, 100–200 mesh and 200–300 mesh; Qingdao Marine Chemical Factory), Sephadex LH-20 gel (40–70 lm; GE Healthcare, Sweden). TLC: silica gel G (Qingdao Marine Chemical Factory). Prep. HPLC (with SPD-20A detector): ODS columns (25 cm 10 mm i.d.) at r.t. on a Pegasil ODS-II 5 lm column (Waters Scientific Co., Ltd., USA).Optical rotation: TU-1901 spectrometer. UV Spectra: UV-210A spectrometer; kmax in nm. IR spectra: Nicolet 170 SX FT-IR spectrometer; KBr pellets; in cm1. NMR spectra: Bruker NMR spectrometer; at 400 (1 H) and 100 MHz (13C);
d in ppm, J in Hz. HR-ESI-MS: Bruker APEX II mass spectrometer, ESI-MS: LCMS-2020 mass spectrometer, in m/z.
3.2. Plant material
The roots of Clematis florida Thunb. var. plena D. Don were purchased from Ningde, Fujian Province of China in May 2016 and identified by Prof. Yonghong Zhang, Fujian Medical University. Clematis florida Thunb. var. plena D. Don is a variety of Clematis florida Thunb., and there are obvious difference in the shape of stamens between them. The stamens in C. florida var. plena are petal-like, while wide linear in C. florida (Editorial Committee of Flora of China 1980). A voucher specimen (No. zyh 20160502) has been deposited in the Laboratory of the Natural Products, Fujian Medical University.
3.3. Preparation of the methanol extract and the fractions
Dried roots of C. florida var. plena (25 kg) were ground and extracted with methanol at room temperature. The solvent was evaporated under vacuum to afford 1100 g crude extract (yield, 4.4%). The methanol extract of C. florida var. plena (MCF) was then suspended in water and partitioned successively with petroleum ether, ethyl acetate and n-butanol. Each fraction was evaporated in vacuo to yield the residues of petroleum ether 85.5 g (7.8%), ethyl acetate 93.1 (8.5%), n-butanol 391.7 g (35.6%), respectively.
3.4. Evaluation of anti-inflammatory activity
3.4.1. Animals
Male ICR mice (approximately 20 g each) were obtained from the Laboratory Animal Center, Fujian Medical University and housed in temperature-controlled rooms (22–23 C). The food and water were supplied ad libitum and each experimental group contained 10 animals. Animals required adaptive feeding for a week, and fasting for 12 h before the experiment. All experimental protocols were conducted in accordance with the National Institutes of Health Guide for Care and Use of Laboratory Animals (Publication No. 85-23, revised 1985) and were approved by Committee of Ethics of Fujian Medical University, China.
3.4.2. Ear edema induced by xylene
MCF and the fractions were suspended in a 0.5% (w/v) sodium carboxyl methylcellulose (CMC-Na). The doses employed were expressed as mg of the dried extract per kg body weight. All the treatments involved intragastric administration (i.g.) to the animals in weight-based dosages. Aspirin was used as the standard anti-inflammatory 2928 K.-H. SUN ET AL. drug. After the administration of extracts or standard drug for 1 h, each mouse was externally treated with a test substance at 40 lL xylene solvent on surface of the right ear, and the left ear served as the control. After 1 h of xylene application, the mice were sacrificed by cervical dislocation. Circular sections (diameter: 6 mm) of both ears of each mouse were removed and weighted using an electronic analytical balance with 0.1 mg precision to calculate the inhibition of ear edema. The difference in weight between the two plugs was taken as a measure of edematous response. The percentage of protection was calculated using the following ratio:
ð Þ control mean treated mean 100%=control mean
3.4.3. Statistical analysis
The data represent the means ± SD (n ¼ 10). Differences between experimental groups and control group were tested using student’s t test; P < 0.01 were considered significant.
3.5. Purification
A portion of ethyl acetate extract (93.1 g) was isolated by silica gel (100–200 mesh) column chromatography (8 50 cm, 750 g) and eluted with petroleum ether/EtOAc in gradient mode (from 100:0 to 0:100, v/v) to afford eighteen fractions (Fr. A1-Fr. A18); Fr. A11 (8.3 g) was subjected to C-18ODS (solvent: MeOH/H2O, 5:95-100:0, v/v) to give six subfractions (Fr. A11-1 - Fr. A11-6); the subfraction Fr. A11-4 (60% MeOH, 1.9 g) was seperated by Sephadex LH-20 (CH3Cl/MeOH 1:1) and purified by semi-PHPLC (CH3CN/H2O 33:67, 2.0 mLmin1) to yield compound 4 (12.1 mg) and compound 5 (37.4 mg).
The n-butanol extract (391.7 g) was fractionated by MCI gel column and eluted with H2O (Fr. B1), 20% MeOH (Fr. B2), 50% MeOH (Fr. B3), 70% MeOH (Fr. B4), 90% MeOH (Fr. B5) and MeOH (Fr. B6). The Fr. B2 (27.3 g) was further subjected to Sephadex LH-20 eluted with CH3Cl/MeOH (1:1) and purified by semi-PHPLC (CH3CN/H2O 15:85, 3.0 mLmin1) to yield compounds 1 (55.2 mg), 2 (35.7 mg), 3 (33.4 mg). The Fr. B4(60.2 g) was subjected to C-18ODS (solvent: MeOH/H2O, 5:95-100:0, v/v) to give six subfractions (Fr. B4-1 - Fr. B4-6); the subfraction Fr. B4-4 (60% MeOH, 19.2 g) was purified by semi-PHPLC (CH3CN/H2O 29:71, 3.0 mLmin1) to afford compounds 6 (79.5 mg), 7 (77.3 mg), 8 (1131.6 mg) and 9 (1193.2 mg). The Fr. B5 (33.0 g) was seperated using a semi-PHPLC (MeOH/H2O 55:45-100:0, 3.0 mLmin1) to yield compound 10 (161.7 mg).
3.6. Acid hydrolysis of compound 1
Compound 1 and the authentic sugars were dissolved in methanol and spotted on a silica gel plate, then the plate was fumigated by the steam of hydrochloric acid for 30 min, after this period, the plate was expanded by n-butanol/EtOAc/2-propanol/HOAc/H2O (7:20:12:7:6). D-Glc and L-Rha were detected from compound 1 by comparing with the authentic sugars. The Rf of the D-Glc and L-Rha were 0.53 and 0.70, respectively. NATURAL PRODUCT RESEARCH 2929 a-L-rhamnopyranosyl-(1!6)-b-D-glucopyranosyl 6-methoxy-3-indolecarbonate (1): light brown gum; [a] 20D-121.5 (c 2.0, MeOH), UV (MeOH): kmax 286, 232, 211 nm; IR (KBr): max 3357, 2926, 1695, 1529, 1433, 1170, 1068, 980 cm1; HRESI-MS m/z: 522.1576 [M þ Na]þ (calcd for C22H29NO12Na, 522.1582); 1H and 13C NMR data, see Table S1.
4. Conclusion
The result of xylene ear inflammation in mice showed that n-butanol extract and its subfractions of powdered root of Clematis florida var. plena exerted anti-inflammatory activity in vivo against ear edema. Bioactivity-guided isolation of the n-butanol yielded one new alkaloid 1, together with three known analogues 2–4, one aromatic acid 5 and five known triterpene saponins 6–10. The n-butanol fraction exhibited significant anti-inflammatory activity between 600 and 800 mg/kg, in a dose-dependent manner.
At 200 mg/kg dose, the anti-inflammatory activity of triterpene saponins (8, 9) was superior to that of alkaloid (1) (50.9%, 54.7% vs 27.0%) and the content of triterpene saponins was high in the plant, indicating that the triterpene saponins might be the anti-inflammatory constituents. The triterpene saponins isolated from the genus Clematis have been reported for their anti-inflammatory activity (Fu et al. 2010). C. florida var. plena was recognized to be a good source for anti-inflammatory activity may be attributed to these constituents. The results demonstrate the anti-inflammatory properties of C. florida var. plena which might justify the use of this plant for the treatment of inflammatory disease in Chinese, folk and herbal medicine.
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
This work was financially supported by the Natural Science Foundation of Fujian Province [grant number 2016J01369], [grant number 2018J01847]; the Open Project of National Marine Bureau Key Laboratory of Marine Biogenetic Resources [grant number HY201807], [grant number HY201604]; the Science and technology innovation platform project of Fujian Province [grant number 2018Y2001].
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CAS No. 101976-49-210H-Phenothiazine, 3-methoxy-10-[(1-methyl-4-piperidinyl)methyl]- Catalog No.:AG000659 MDL No.: MF:C20H24N2OS MW:340.4824 |
CAS No. 101976-53-810H-Phenothiazine, 10-(1-methyl-3-piperidinyl)- Catalog No.:AG000658 MDL No.: MF:C18H20N2S MW:296.4298 |
CAS No. 101976-94-72-Pentenoic acid, 5-[2-[bis(4-chlorophenyl)methoxy]cyclohexyl]-, methyl ester, [1α(E),2β]- (9CI) Catalog No.:AG000657 MDL No.: MF:C25H28Cl2O3 MW:447.3940 |
CAS No. 101976-96-92-Pentenoic acid, 5-[2-[(4-bromophenyl)methoxy]cyclohexyl]-, methyl ester, [1α(E),2β]- (9CI) Catalog No.:AG000656 MDL No.: MF: MW: |
CAS No. 1019767-63-5Pyridine, 3-bromo-4-(phenylmethoxy)- Catalog No.:AG000652 MDL No.:MFCD11226996 MF:C12H10BrNO MW:264.1179 |
CAS No. 101977-74-63-Pyridinecarboxylic acid, carboxyphenylmethyl ester Catalog No.:AG000655 MDL No.:MFCD06804522 MF:C14H11NO4 MW:257.2414 |
CAS No. 1019770-99-02-Benzoxazolecarboxylic acid, sodium salt (1:1) Catalog No.:AG000651 MDL No.:MFCD17676126 MF:C8H4NNaO3 MW:185.1120 |
CAS No. 1019771-90-42H-Indol-2-one, 1,3-dihydro-3-(6-hydroxy-1,3-benzodioxol-5-yl)- Catalog No.:AG000650 MDL No.:MFCD16659827 MF:C15H11NO4 MW:269.2521 |
CAS No. 1019779-04-4Catalog No.:AG00064Z MDL No.:MFCD22689439 MF:C20H26Cl2F2N4O MW:447.3494 |
CAS No. 101979-26-42-Propenoic acid, 2-[(1-oxodecyl)amino]-, methyl ester Catalog No.:AG000654 MDL No.: MF:C14H25NO3 MW:255.3532 |
CAS No. 101979-45-7Ethanone, 1-[(4S)-4-(1-methylethyl)-2-thioxo-3-thiazolidinyl]- Catalog No.:AG000653 MDL No.:MFCD10570251 MF:C8H13NOS2 MW:203.3249 |
CAS No. 10198-28-4Benzofuran, 2,3,4,5,6,7-hexahydro- Catalog No.:AG00065N MDL No.: MF:C8H12O MW:124.1803 |
CAS No. 10198-31-9Benzofuran, 2,3,4,5,6,7-hexahydro-2-methyl- Catalog No.:AG00065M MDL No.: MF:C9H14O MW:138.2069 |
CAS No. 10198-74-04(3H)-Pyrimidinone, 6-hydroxy-2-(2-pyridinyl)- Catalog No.:AG00065L MDL No.:MFCD11109859 MF:C9H7N3O2 MW:189.1708 |
CAS No. 10198-77-3Pyrimidine, 4,6-dichloro-5-methyl-2-(2-pyridinyl)- Catalog No.:AG00066C MDL No.:MFCD18844051 MF:C10H7Cl2N3 MW:240.0887 |
CAS No. 10198-78-4Pyrimidine, 4,6-dichloro-5-phenyl-2-(2-pyridinyl)- Catalog No.:AG00066B MDL No.: MF:C15H9Cl2N3 MW:302.1581 |
CAS No. 10198-79-5Pyrimidine, 5-methyl-2-(2-pyridinyl)- Catalog No.:AG00066A MDL No.: MF:C10H9N3 MW:171.1986 |
CAS No. 10198-83-1Catalog No.:AG000669 MDL No.: MF:C9H7N3 MW:157.1720 |
CAS No. 10198-89-71,3-Propanedione, 1,3-di-2-pyridinyl- Catalog No.:AG000668 MDL No.:MFCD01321157 MF:C13H10N2O2 MW:226.2307 |
CAS No. 10198-96-6Catalog No.:AG000667 MDL No.:MFCD08275257 MF:C8H6N4 MW:158.1600 |
CAS No. 101980-41-0Benzene, 2-bromo-1-(1-methylethyl)-4-nitro- Catalog No.:AG000663 MDL No.:MFCD12024309 MF:C9H10BrNO2 MW:244.0852 |
CAS No. 101981-89-91,4-Benzenediol, 2-chloro-, monoacetate (9CI) Catalog No.:AG000662 MDL No.: MF:C8H9ClO4 MW:204.6077 |
CAS No. 1019842-24-0Cyclobutanepropanoic acid, 3-oxo-, methyl ester Catalog No.:AG00065T MDL No.:MFCD19441111 MF:C8H12O3 MW:156.1791 |
CAS No. 1019842-26-2Cyclobutanepentanoic acid, 3-oxo-, ethyl ester Catalog No.:AG00065S MDL No.:MFCD23135412 MF:C11H18O3 MW:198.2588 |
CAS No. 1019852-03-9Methanone, (4-methyl-1-piperazinyl)-4-piperidinyl-, hydrochloride (1:2) Catalog No.:AG00065R MDL No.:MFCD05864745 MF:C11H23Cl2N3O MW:284.2258 |
CAS No. 1019852-04-03-Piperidinecarboxamide, hydrochloride (1:1) Catalog No.:AG00065Q MDL No.: MF:C6H13ClN2O MW:164.6332 |
CAS No. 1019855-82-3Cyclopropanesulfonamide, N-[(4-nitrophenyl)methyl]- Catalog No.:AG00065P MDL No.:MFCD22493432 MF:C10H12N2O4S MW:256.2783 |
CAS No. 1019855-83-4Cyclopropanesulfonamide, N-[(4-aminophenyl)methyl]- Catalog No.:AG00065O MDL No.:MFCD20352157 MF:C10H14N2O2S MW:226.2954 |
CAS No. 101986-32-73-Oxazolidineacetonitrile, 4-phenyl-, (4R)- Catalog No.:AG000661 MDL No.: MF:C11H12N2O MW:188.2258 |
CAS No. 101986-68-9Acetamide, N-[4-(2-pyrazinyl)phenyl]- Catalog No.:AG000660 MDL No.: MF:C12H11N3O MW:213.2352 |
CAS No. 101986-69-0Acetamide, N-[4-(4-oxido-2-pyrazinyl)phenyl]- Catalog No.:AG00065Z MDL No.: MF:C12H11N3O2 MW:229.2346 |
CAS No. 101987-45-52-Pyrimidinamine, N-methyl-N-phenyl-4-(4-pyridinyl)- Catalog No.:AG00065Y MDL No.: MF:C16H14N4 MW:262.3092 |
CAS No. 101987-76-2Catalog No.:AG00065X MDL No.: MF:C18H19ClFN3O3 MW:379.8132 |
CAS No. 101987-86-4Benzenepropanoic acid, 3-chloro-2,4,5-trifluoro-β-oxo-, ethyl ester Catalog No.:AG00065W MDL No.:MFCD09037898 MF:C11H8ClF3O3 MW:280.6276 |
CAS No. 101987-89-73-Quinolinecarboxylic acid, 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo- Catalog No.:AG00065V MDL No.:MFCD08706388 MF:C13H8ClF2NO3 MW:299.6573 |
CAS No. 101988-70-91,3,5-Triazine-2,4-diamine, N2-methyl-6-(2,2,2-trifluoroethoxy)- Catalog No.:AG00065U MDL No.:MFCD00452913 MF:C6H8F3N5O MW:223.1558 |
CAS No. 10199-00-5Catalog No.:AG000666 MDL No.:MFCD00010288 MF:C8H6N4 MW:158.1600 |
CAS No. 10199-50-51H-Pyrazol-5-amine, 1-methyl-3-phenyl- Catalog No.:AG000665 MDL No.:MFCD00067874 MF:C10H11N3 MW:173.2144 |
CAS No. 10199-51-61H-Pyrazole-3-carboxylic acid, 1-methyl-5-phenyl-, ethyl ester Catalog No.:AG000664 MDL No.:MFCD08060533 MF:C13H14N2O2 MW:230.2625 |
CAS No. 10199-53-81H-Pyrazole-3-carboxylic acid, 1-methyl-5-phenyl- Catalog No.:AG000671 MDL No.:MFCD08271933 MF:C11H10N2O2 MW:202.2093 |
CAS No. 10199-57-21H-Pyrazole-3-carboxylic acid, 5-methyl-1-phenyl- Catalog No.:AG000670 MDL No.:MFCD00124910 MF:C11H10N2O2 MW:202.2093 |
CAS No. 10199-59-41H-Pyrazole-1-carboxylic acid, ethyl ester Catalog No.:AG00066Z MDL No.: MF:C6H8N2O2 MW:140.1399 |
CAS No. 10199-61-81H-Pyrazole-1-acetic acid, ethyl ester Catalog No.:AG00066Y MDL No.:MFCD00159620 MF:C7H10N2O2 MW:154.1665 |
CAS No. 10199-63-0Ethanone, 1-(3,5-dimethyl-1H-pyrazol-1-yl)- Catalog No.:AG00066X MDL No.: MF:C7H10N2O MW:138.1671 |
CAS No. 10199-64-1Ethanone, 1-(1H-pyrazol-1-yl)- Catalog No.:AG00066W MDL No.: MF:C5H6N2O MW:110.1139 |
CAS No. 10199-66-3Methanone, phenyl-1H-pyrazol-1-yl- Catalog No.:AG00066V MDL No.: MF:C10H8N2O MW:172.1833 |
CAS No. 10199-67-41H-Pyrazole, 1-(phenylmethyl)- Catalog No.:AG00066U MDL No.:MFCD00462231 MF:C10H10N2 MW:158.1998 |
CAS No. 10199-68-5Catalog No.:AG00066T MDL No.:MFCD00462204 MF:C9H8N2 MW:144.1732 |
CAS No. 10199-69-61H-Pyrazole, 1-methyl-4-phenyl- Catalog No.:AG00066S MDL No.:MFCD12964229 MF:C10H10N2 MW:158.1998 |
CAS No. 10199-85-6Benzene, 1,3-dichloro-2,4-dinitro- Catalog No.:AG00066R MDL No.:MFCD00823272 MF:C6H2Cl2N2O4 MW:236.9971 |
CAS No. 10199-87-81,3-Benzenediamine, 2,4-dinitro- Catalog No.:AG00066Q MDL No.: MF:C6H6N4O4 MW:198.1362 |
CAS No. 10199-89-02,1,3-Benzoxadiazole, 4-chloro-7-nitro- Catalog No.:AG00066P MDL No.:MFCD00005808 MF:C6H2ClN3O3 MW:199.5514 |
CAS No. 10199-90-32,1,3-Benzoxadiazole, 4-azido-7-nitro- Catalog No.:AG00066O MDL No.: MF:C6H2N6O3 MW:206.1185 |
CAS No. 101990-17-4Pyridine, 2-fluoro-5-[[2-(nitromethylene)-1-imidazolidinyl]methyl]- Catalog No.:AG00066N MDL No.: MF:C10H11FN4O2 MW:238.2183 |
CAS No. 101990-45-8Pyridine, 2-bromo-5-(bromomethyl)- Catalog No.:AG00066M MDL No.:MFCD11656267 MF:C6H5Br2N MW:250.9186 |
CAS No. 101990-64-13-Pyridinecarbonyl chloride, 6-(methylthio)- Catalog No.:AG00066L MDL No.: MF:C7H6ClNOS MW:187.6466 |
CAS No. 101990-68-53-Pyridinemethanol, 6-phenoxy- Catalog No.:AG00066K MDL No.:MFCD02682069 MF:C12H11NO2 MW:201.2212 |
CAS No. 101990-69-64-Pyridinemethanol, 2,6-dichloro- Catalog No.:AG00066J MDL No.:MFCD00052638 MF:C6H5Cl2NO MW:178.0160 |
CAS No. 101990-70-9Pyridine, 5-(chloromethyl)-2-methoxy- Catalog No.:AG00066I MDL No.:MFCD10697570 MF:C7H8ClNO MW:157.5975 |
CAS No. 101990-72-1Pyridine, 2,6-dichloro-4-(chloromethyl)- Catalog No.:AG00066H MDL No.:MFCD03783562 MF:C6H4Cl3N MW:196.4617 |
CAS No. 101990-73-2Pyridine, 2-chloro-4-(chloromethyl)- Catalog No.:AG00066G MDL No.:MFCD09991655 MF:C6H5Cl2N MW:162.0166 |
CAS No. 101991-76-81-Propanone, 2-(2,4-dichlorophenoxy)-1-(1-piperidinyl)- Catalog No.:AG00066F MDL No.:MFCD01339369 MF:C14H17Cl2NO2 MW:302.1963 |
CAS No. 1019918-39-8Pyridine, 4-bromo-2-hydrazinyl- Catalog No.:AG00066E MDL No.:MFCD00234091 MF:C5H6BrN3 MW:188.0252 |
CAS No. 1019918-41-21,2,4-Triazolo[4,3-a]pyridin-3-amine, 7-bromo- Catalog No.:AG00066D MDL No.: MF:C6H5BrN4 MW:213.0347 |
CAS No. 1019918-43-41,2,4-Triazolo[4,3-a]pyridine, 7-bromo-3-(2-fluorophenyl)- Catalog No.:AG000679 MDL No.: MF:C12H7BrFN3 MW:292.1065 |
CAS No. 1019918-45-61,2,4-Triazolo[4,3-a]pyridine, 7-chloro-3-(2-fluorophenyl)- Catalog No.:AG000678 MDL No.: MF:C12H7ClFN3 MW:247.6555 |
CAS No. 1019918-47-81,2,4-Triazolo[4,3-a]pyridine, 7-bromo-3-(2-chlorophenyl)- Catalog No.:AG000677 MDL No.: MF:C12H7BrClN3 MW:308.5611 |
CAS No. 1019918-60-51,2,4-Triazolo[4,3-a]pyridine, 7-chloro-3-(2-chlorophenyl)-5-methyl- Catalog No.:AG000676 MDL No.: MF:C13H9Cl2N3 MW:278.1367 |
CAS No. 1019918-88-71,2,4-Triazolo[4,3-a]pyridine, 7-chloro-3-(2-chlorophenyl)- Catalog No.:AG000675 MDL No.: MF:C12H7Cl2N3 MW:264.1101 |
CAS No. 101992-41-0Ethanedione, 1,1'-[1,6-hexanediylbis(oxy-4,1-phenylene)]bis[2-phenyl- (9CI) Catalog No.:AG00067P MDL No.: MF:C34H30O6 MW:534.5984 |
CAS No. 101992-47-6Ethanedione, 1,1'-[1,3-propanediylbis(oxy-4,1-phenylene)]bis[2-phenyl- (9CI) Catalog No.:AG00067O MDL No.: MF:C31H24O6 MW:492.5187 |
CAS No. 101992-89-61-Butanol, 4-(methoxymethoxy)- Catalog No.:AG00067N MDL No.: MF:C6H14O3 MW:134.1736 |
CAS No. 1019929-89-5Pyridine, 4,6-dichloro-3-methoxy-2-methyl- Catalog No.:AG000674 MDL No.:MFCD11847534 MF:C7H7Cl2NO MW:192.0426 |
CAS No. 101993-02-62-Oxazolamine, 4,5-dihydro-5-(methoxymethyl)- Catalog No.:AG00067M MDL No.: MF:C5H10N2O2 MW:130.1451 |
CAS No. 1019930-14-32-Pyridinecarboxylic acid, 4-chloro-3-methoxy-6-phenyl- Catalog No.:AG000673 MDL No.: MF:C13H10ClNO3 MW:263.6764 |
CAS No. 101994-23-42H-1-Benzopyran-6-carbonitrile, 7-hydroxy-4,8-dimethyl-2-oxo- Catalog No.:AG00067L MDL No.: MF:C12H9NO3 MW:215.2048 |
CAS No. 101996-52-52H-Pyran, 3-chlorotetrahydro-2-(1-methylethyl)-, cis- (9CI) Catalog No.:AG00067K MDL No.: MF:C8H15ClO MW:162.6571 |
CAS No. 101997-49-3Ethanone, 2-[[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]amino]-1-(1-piperidinyl)- Catalog No.:AG00067J MDL No.: MF:C16H22N2O3 MW:290.3575 |
CAS No. 101998-53-22-Propanone, 1-(1-methyl-2-imidazolidinylidene)-, (1E)- Catalog No.:AG00067I MDL No.: MF:C7H12N2O MW:140.1830 |
CAS No. 101999-40-02(3H)-Furanone, dihydro-3-(phenylmethoxy)- Catalog No.:AG00067H MDL No.: MF:C11H12O3 MW:192.2112 |
CAS No. 101999-44-42H-1-Benzopyran-2-one, 7-ethyl-4-methyl- Catalog No.:AG00067G MDL No.: MF:C12H12O2 MW:188.2225 |
CAS No. 101999-45-52H-1-Benzopyran-4-acetamide, 7-hydroxy-2-oxo- Catalog No.:AG00067F MDL No.:MFCD06001840 MF:C11H9NO4 MW:219.1935 |
CAS No. 101999-46-62H-Naphtho[1,2-b]pyran-4-acetic acid, 2-oxo- Catalog No.:AG00067E MDL No.:MFCD00434035 MF:C15H10O4 MW:254.2375 |
CAS No. 101999-59-1Catalog No.:AG00067D MDL No.: MF:C10H17IO MW:280.1459 |
CAS No. 101999-65-91,6-Tetradecadien-3-one, 14-iodo-, (6E)- Catalog No.:AG00067C MDL No.: MF:C14H23IO MW:334.2363 |
CAS No. 101999-70-64-Cyclotetradecen-1-one, (4E)- Catalog No.:AG00067B MDL No.: MF:C14H24O MW:208.3398 |
CAS No. 101999-73-9Bicyclo[7.2.2]tridec-9(13)-ene Catalog No.:AG00067A MDL No.: MF:C13H22 MW:178.3138 |
CAS No. 1019995-16-43-Pyridinecarboxylic acid, 4-[(4-ethoxy-1,4-dioxobutyl)amino]-, ethyl ester Catalog No.:AG000672 MDL No.: MF:C14H18N2O5 MW:294.3031 |
CAS No. 1019995-18-61H-Pyrido[4,3-b]azepine-4-carboxylic acid, 2,3-dihydro-5-hydroxy-2-oxo-, ethyl ester Catalog No.:AG00067R MDL No.: MF:C12H12N2O4 MW:248.2347 |
CAS No. 1019996-86-11,1'-Biphenyl, 4-nitro-4'-(trifluoromethoxy)- Catalog No.:AG00067Q MDL No.:MFCD21609608 MF:C13H8F3NO3 MW:283.2027 |
CAS No. 102-02-3Imidodicarbonimidic diamide, N-phenyl- Catalog No.:AG00068B MDL No.:MFCD00179077 MF:C8H11N5 MW:177.2064 |
CAS No. 102-03-4Acetamide, N-[(phenylamino)carbonyl]- Catalog No.:AG00068A MDL No.:MFCD00026166 MF:C9H10N2O2 MW:178.1879 |
CAS No. 102-04-5Catalog No.:AG000689 MDL No.:MFCD00004795 MF:C15H14O MW:210.2711 |
CAS No. 102-05-6Benzenemethanamine, N-methyl-N-(phenylmethyl)- Catalog No.:AG000688 MDL No.:MFCD00022018 MF:C15H17N MW:211.3022 |
CAS No. 102-07-8Catalog No.:AG000687 MDL No.:MFCD00003017 MF:C13H12N2O MW:212.2472 |
CAS No. 102-08-9Catalog No.:AG000686 MDL No.:MFCD00004921 MF:C13H12N2S MW:228.3128 |
CAS No. 102-09-0Catalog No.:AG000685 MDL No.:MFCD00003037 MF:C13H10O3 MW:214.2167 |
CAS No. 102-10-3Phosphorous acid, diphenyl ester Catalog No.:AG000684 MDL No.: MF:C12H10O3P- MW:233.1798 |
CAS No. 102-11-41,2-Ethanediamine, N1,N2-dimethyl-N1-(phenylmethyl)- Catalog No.:AG000683 MDL No.:MFCD00014856 MF:C11H18N2 MW:178.2740 |
CAS No. 102-13-6Benzeneacetic acid, 2-methylpropyl ester Catalog No.:AG000682 MDL No.:MFCD00026482 MF:C12H16O2 MW:192.2542 |
CAS No. 102-14-7Butanoic acid, 4-oxo-4-(phenylamino)- Catalog No.:AG000681 MDL No.:MFCD00029825 MF:C10H11NO3 MW:193.1992 |
CAS No. 102-16-9Benzeneacetic acid, phenylmethyl ester Catalog No.:AG000680 MDL No.:MFCD00022045 MF:C15H14O2 MW:226.2705 |
CAS No. 102-17-0Benzeneacetic acid, (4-methoxyphenyl)methyl ester Catalog No.:AG00067Z MDL No.: MF:C16H16O3 MW:256.2964 |
CAS No. 102-19-2Benzeneacetic acid, 3-methylbutyl ester Catalog No.:AG00067Y MDL No.:MFCD00026517 MF:C13H18O2 MW:206.2808 |
CAS No. 102-20-5Benzeneacetic acid, 2-phenylethyl ester Catalog No.:AG00067X MDL No.:MFCD00022049 MF:C16H16O2 MW:240.2970 |
CAS No. 102-22-7Benzeneacetic acid, (2E)-3,7-dimethyl-2,6-octadien-1-yl ester Catalog No.:AG00067W MDL No.:MFCD00072225 MF:C18H24O2 MW:272.3820 |
CAS No. 102-23-8Benzenesulfonic acid, 3-[2-(4-aminophenyl)diazenyl]- Catalog No.:AG00067V MDL No.: MF:C12H11N3O3S MW:277.2990 |
CAS No. 102-24-9Catalog No.:AG00067U MDL No.:MFCD00005946 MF:C3H9B3O6 MW:173.5330 |
CAS No. 102-25-0Catalog No.:AG00067T MDL No.:MFCD00009261 MF:C12H18 MW:162.2713 |
CAS No. 102-26-11,3,5-Triazine, 2,4,6-triethylhexahydro- Catalog No.:AG00067S MDL No.: MF:C9H21N3 MW:171.2831 |
CAS No. 102-28-3Catalog No.:AG00068Y MDL No.:MFCD00025229 MF:C8H10N2O MW:150.1778 |
CAS No. 102-29-4Catalog No.:AG00068X MDL No.:MFCD00002266 MF:C8H8O3 MW:152.1473 |
CAS No. 102-32-9Benzeneacetic acid, 3,4-dihydroxy- Catalog No.:AG00068W MDL No.:MFCD00004338 MF:C8H8O4 MW:168.1467 |
CAS No. 102-37-42-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl ester Catalog No.:AG00068U MDL No.:MFCD00045754 MF:C11H12O4 MW:208.2106 |
CAS No. 102-38-5Catalog No.:AG00068T MDL No.:MFCD00017014 MF:C7H6N2O3 MW:166.1341 |
CAS No. 102-39-6Acetic acid, 2,2'-[1,3-phenylenebis(oxy)]bis- Catalog No.:AG00068S MDL No.:MFCD00016696 MF:C10H10O6 MW:226.1828 |
CAS No. 102-41-0Ethanol, 2-[(3-methylphenyl)amino]- Catalog No.:AG00068R MDL No.:MFCD00045970 MF:C9H13NO MW:151.2056 |
CAS No. 102-45-4Cyclopentaneethanamine, N,α-dimethyl- Catalog No.:AG00068Q MDL No.:MFCD00864151 MF:C9H19N MW:141.2539 |
CAS No. 102-46-5Benzene, 4-(chloromethyl)-1,2-dimethyl- Catalog No.:AG00068P MDL No.:MFCD00000910 MF:C9H11Cl MW:154.6366 |
CAS No. 102-48-7Benzenemethanamine, 3,4-dimethyl- Catalog No.:AG00068N MDL No.:MFCD00025577 MF:C9H13N MW:135.2062 |
CAS No. 102-49-8Benzenemethanamine, 3,4-dichloro- Catalog No.:AG00068M MDL No.:MFCD00008114 MF:C7H7Cl2N MW:176.0432 |
CAS No. 102-50-1Benzenamine, 4-methoxy-2-methyl- Catalog No.:AG00068L MDL No.:MFCD00007735 MF:C8H11NO MW:137.1790 |
CAS No. 102-51-21,2-Benzenediamine, 4-methoxy- Catalog No.:AG00068K MDL No.:MFCD00047837 MF:C7H10N2O MW:138.1671 |
CAS No. 102-52-3Propane, 1,1,3,3-tetramethoxy- Catalog No.:AG00068J MDL No.:MFCD00008488 MF:C7H16O4 MW:164.1995 |
CAS No. 102-53-4Methanediamine, N,N,N',N'-tetraethyl- Catalog No.:AG00068I MDL No.:MFCD00015115 MF:C9H22N2 MW:158.2844 |
CAS No. 102-54-5Catalog No.:AG00068H MDL No.:MFCD00001427 MF:C10H10Fe MW:186.0314 |
CAS No. 102-56-7Catalog No.:AG00068G MDL No.:MFCD00008368 MF:C8H11NO2 MW:153.1784 |
CAS No. 102-58-95-Octen-4-ol, 2,7-dimethyl-, 4-acetate Catalog No.:AG00068F MDL No.: MF:C12H22O2 MW:198.3019 |
CAS No. 102-62-51,2,3-Propanetriol, 1,2-diacetate Catalog No.:AG00068E MDL No.:MFCD00040498 MF:C7H12O5 MW:176.1672 |
CAS No. 102-63-6Benzenamine, 4-[2-(2,4-dimethylphenyl)diazenyl]-2-methyl- Catalog No.:AG00068D MDL No.: MF:C15H17N3 MW:239.3156 |
CAS No. 102-65-8Benzenesulfonamide, 4-amino-N-(6-chloro-2-pyrazinyl)- Catalog No.:AG00069L MDL No.:MFCD28954637 MF:C10H9ClN4O2S MW:284.7221 |
CAS No. 102-76-11,2,3-Propanetriol, 1,2,3-triacetate Catalog No.:AG00069I MDL No.:MFCD00008716 MF:C9H14O6 MW:218.2039 |
CAS No. 102-83-01,3-Propanediamine, N1,N1-dibutyl- Catalog No.:AG00069F MDL No.:MFCD00008219 MF:C11H26N2 MW:186.3375 |
CAS No. 102-84-1Phosphorous acid, tri-2-propen-1-yl ester Catalog No.:AG00069E MDL No.:MFCD00014948 MF:C9H15O3P MW:202.1874 |
CAS No. 102-85-2Phosphorous acid, tributyl ester Catalog No.:AG00069D MDL No.:MFCD00009437 MF:C12H27O3P MW:250.3147 |
CAS No. 102-86-3Catalog No.:AG00069C MDL No.:MFCD00009523 MF:C18H39N MW:269.5090 |
CAS No. 102-87-41-Dodecanamine, N,N-didodecyl- Catalog No.:AG00069B MDL No.:MFCD00008971 MF:C36H75N MW:521.9874 |
CAS No. 102-88-51-Octadecanamine, N,N-dioctadecyl- Catalog No.:AG00069A MDL No.: MF:C54H111N MW:774.4658 |
CAS No. 102-92-12-Propenoyl chloride, 3-phenyl- Catalog No.:AG000699 MDL No.:MFCD00000732 MF:C9H7ClO MW:166.6043 |
CAS No. 102-93-2Catalog No.:AG000698 MDL No.:MFCD00025535 MF:C9H11NO MW:149.1897 |
CAS No. 102-94-32-Propenoic acid, 3-phenyl-, (2Z)- Catalog No.:AG000697 MDL No.:MFCD00466869 MF:C9H8O2 MW:148.1586 |
CAS No. 102-96-5Catalog No.:AG000696 MDL No.:MFCD00007402 MF:C8H7NO2 MW:149.1467 |
CAS No. 102-97-6Benzenemethanamine, N-(1-methylethyl)- Catalog No.:AG000695 MDL No.:MFCD00008863 MF:C10H15N MW:149.2328 |
CAS No. 102-98-7Mercurate(2-), [orthoborato(3-)-κO]phenyl-, hydrogen (1:2) Catalog No.:AG000694 MDL No.:MFCD00019938 MF: MW: |
CAS No. 1020-16-21-Propanone, 3-(4-morpholinyl)-1-phenyl-, hydrochloride (1:1) Catalog No.:AG000693 MDL No.: MF:C13H18ClNO2 MW:255.7405 |
CAS No. 1020-31-11,2-Benzenediol, 3,5-bis(1,1-dimethylethyl)- Catalog No.:AG000692 MDL No.:MFCD00008819 MF:C14H22O2 MW:222.3233 |
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CAS No. 1020-39-9Benzamide, N-(2-chlorophenyl)- Catalog No.:AG000690 MDL No.: MF:C13H10ClNO MW:231.6776 |
CAS No. 1020-40-2Benzamide, N-(2-mercaptophenyl)- Catalog No.:AG0006AA MDL No.: MF:C13H11NOS MW:229.2975 |
CAS No. 1020-67-32-Butenoic acid, 3-[(phenylmethyl)amino]-, ethyl ester Catalog No.:AG0006A9 MDL No.: MF:C13H17NO2 MW:219.2796 |
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CAS No. 10200-31-4Catalog No.:AG0006A0 MDL No.: MF:C8H14O4 MW:174.1944 |
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CAS No. 10200-59-6Catalog No.:AG00069X MDL No.:MFCD00142924 MF:C4H3NOS MW:113.1377 |
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CAS No. 10200-72-3Catalog No.:AG00069V MDL No.: MF:C7H5NSSe MW:214.1463 |
CAS No. 10200-74-5Catalog No.:AG00069U MDL No.: MF:C7H5NOSe MW:198.0807 |
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CAS No. 102000-59-9Catalog No.:AG00069R MDL No.:MFCD01661065 MF:C7H8N2O2 MW:152.1506 |
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CAS No. 102001-19-4Methanone, (3,4-dimethylphenyl)-2-pyridinyl- Catalog No.:AG00069N MDL No.: MF:C14H13NO MW:211.2591 |
CAS No. 102001-21-8Catalog No.:AG00069M MDL No.: MF:C14H13NO MW:211.2591 |
CAS No. 102001-75-2Phenol, 4,4'-(3(2H)-benzofuranylidene)bis- (9CI) Catalog No.:AG0006AZ MDL No.: MF:C20H16O3 MW:304.3392 |
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CAS No. 1020056-33-01H-Pyrrolo[3,2-b]pyridine-6-carboxaldehyde Catalog No.:AG0006AN MDL No.:MFCD09859114 MF:C8H6N2O MW:146.1460 |
CAS No. 1020056-56-71H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-methyl- Catalog No.:AG0006AM MDL No.:MFCD09965882 MF:C8H7ClN2 MW:166.6076 |
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CAS No. 1020056-77-21H-Pyrrolo[2,3-b]pyridine, 5-chloro-4-iodo- Catalog No.:AG0006AK MDL No.:MFCD09965892 MF:C7H4ClIN2 MW:278.4775 |
CAS No. 1020056-82-91H-Pyrrolo[2,3-b]pyridin-5-ol, 4-chloro- Catalog No.:AG0006AJ MDL No.:MFCD09965894 MF:C7H5ClN2O MW:168.5804 |
CAS No. 1020056-87-41H-Pyrrolo[2,3-b]pyridine, 5-chloro-4-methyl- Catalog No.:AG0006AI MDL No.:MFCD09965896 MF:C8H7ClN2 MW:166.6076 |
CAS No. 1020056-98-74-Pyridinecarboxylic acid, 2,3-dibromo- Catalog No.:AG0006AH MDL No.:MFCD09997708 MF:C6H3Br2NO2 MW:280.9015 |
CAS No. 1020057-82-21H-Pyrazole-3-carbonitrile, 5-amino-1-[4-(trifluoromethyl)phenyl]- Catalog No.:AG0006AG MDL No.: MF:C11H7F3N4 MW:252.1953 |
CAS No. 1020057-84-41H-Pyrazole-3-carbonitrile, 5-amino-1-[3-(trifluoromethyl)phenyl]- Catalog No.:AG0006AF MDL No.: MF:C11H7F3N4 MW:252.1953 |
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CAS No. 1020058-12-11H-Pyrazole-4-carbonitrile, 5-amino-3-methyl-1-(4-methylphenyl)- Catalog No.:AG0006AC MDL No.: MF:C12H12N4 MW:212.2505 |
CAS No. 1020058-21-21H-Pyrazole-3-carbonitrile, 5-amino-1-(4-methylphenyl)- Catalog No.:AG0006AB MDL No.: MF:C11H10N4 MW:198.2239 |
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CAS No. 1020058-47-2Benzenepropanoic acid, 5-bromo-2-fluoro-β-oxo-, ethyl ester Catalog No.:AG0006B5 MDL No.: MF:C11H10BrFO3 MW:289.0977 |
CAS No. 1020058-49-4Benzenepropanoic acid, 2-bromo-5-fluoro-β-oxo-, ethyl ester Catalog No.:AG0006B4 MDL No.: MF:C11H10BrFO3 MW:289.0977 |
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CAS No. 1020101-33-02-Quinolinecarboxylic acid, 4-chloro-8-methyl-, methyl ester Catalog No.:AG0006B0 MDL No.:MFCD12913953 MF:C12H10ClNO2 MW:235.6663 |
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