- A New Lupane-Type Triterpenoid Saponin from Lonicera macranthoides
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A new lupane-type triterpenoid saponin, named lonimacranthoside A 1, was isolated from the flower buds of Lonicera macranthoides. The structure of lonimacranthoside A1 was elucidated as 3β-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl-23- hydroxy-lup-20(29)-en-28-oic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (1) on the basis of spectral data and chemical evidence. This is the first reported occurrence of a lupane-type saponin in the plant.
- Chen, Yu,Zhao, Youyi,Wang, Ming,Wang, Qizhi,Shan, Yu,Guan, Fuqin,Feng, Xu
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- Triterpenoid saponins from the buds of Lonicera similis
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Four new lupane triterpenoid saponins, along with one known lupane and eight hederagenin saponins, were isolated from the EtOH extract of the buds of Lonicera similis Hemsl. The structures of the new compounds were established as 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl 23-hydroxybetulinic acid 28-O-β-D-glucopyranosyl ester (lonisimilioside A, 1), 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl 23-hydroxybetulinic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (lonisimilioside B, 2), 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl betulinic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (lonisimilioside C, 3) and 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl betulinic acid 28-O-β-D-glucopyranosyl ester (lonisimilioside D, 4), respectively. The cytotoxic activities of the isolates against human cancer cell lines HepG2, MCF-7 and A-549 were evaluated. Only the monodesmosidic saponin with a free carboxyl group at C-28 (12) exhibited significant cytotoxicities against HepG2, MCF-7 and A-549 cell lines with the IC50 values of 8.98?±?0.19, 12.48?±?0.45 and 11.62?±?0.54?μM, respectively. Furthermore, Hoechst fluorescence 33342 staining was used to demonstrate that 12 could induce HepG2 and A-549 cells apoptosis significantly.
- Zhang, Xiao,Zou, Li-Hua,He, Yu-Lin,Peng, Cheng,Guo, Li,Xiong, Liang
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p. 2282 - 2290
(2017/12/06)
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- Improving Physical Properties via C-H Oxidation: Chemical and Enzymatic Approaches
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Physicochemical properties constitute a key factor for the success of a drug candidate. Whereas many strategies to improve the physicochemical properties of small heterocycle-type leads exist, complex hydrocarbon skeletons are more challenging to derivatize because of the absence of functional groups. A variety of C-H oxidation methods have been explored on the betulin skeleton to improve the solubility of this very bioactive, yet poorly water-soluble, natural product. Capitalizing on the innate reactivity of the molecule, as well as the few molecular handles present on the core, allowed oxidations at different positions across the pentacyclic structure. Enzymatic oxidations afforded several orthogonal oxidations to chemical methods. Solubility measurements showed an enhancement for many of the synthesized compounds. A handle on [O]: A variety of C-H oxidation methods were explored on the betulin skeleton to improve the solubility of this bioactive, yet poorly water-soluble, natural product. The innate reactivity of the molecule, as well as the molecular handles present on the core, allowed oxidations at different positions. Solubility enhancement was observed for many of the synthesized compounds.
- Michaudel, Quentin,Journot, Guillaume,Regueiro-Ren, Alicia,Goswami, Animesh,Guo, Zhiwei,Tully, Thomas P.,Zou, Lufeng,Ramabhadran, Raghunath O.,Houk, Kendall N.,Baran, Phil S.
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supporting information
p. 12091 - 12096
(2016/02/23)
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- A partial synthesis of 23-hydroxybetulonic acid and 23-hydroxybetulinic acid starting from betulinic acid
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A partial syntheses of the biologically active 23-hydroxybetulonic acid and 23-hydroxybetulinic acid starting from the naturally abundant betulinic acid has been developed in which the key step was the Baldwin's cyclopalladation of the 23-methyl group from a 3-one oxime of betulinic acid, an important drug in Chinese medicine.
- Sun, Fei,Zhu, Peiqing,Yao, Hequan,Wu, Xiaoming,Xu, Jinyi
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p. 254 - 257
(2012/10/08)
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- 23-Substituted Derivatives of Lupane-type Pentacyclic Triterpenoids
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The present invention comprises small molecule inhibitors of cell proliferative conditions, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprises pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.
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Page/Page column 25-26
(2010/06/19)
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- NMDA AND MC RECEPTOR ANTAGONISTS EXHIBITING NEUROPROTECTIVE AND MEMORY ENHANCING ACTIVITIES
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The present invention provides therapeutically active compounds and compositions as NMDA and MC receptor antagonists, which are useful in preventing and treating central nervous system disorders by inhibiting over-activation of NMDA and/or MC receptors. In one aspect, the present invention provides methods of treating and/or preventing neurodegenerative diseases and neuropathological disorders, methods of providing neuroprotection under stress conditions such as a stroke, methods of enhancing the brain's cognitive functions and methods of treating depression, anxiety and cachexia induced by a chronic disease in mammals and humans.
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Page/Page column 37
(2009/01/20)
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- Triterpene glycosides from Pulsatilla chinensis
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Four triterpene glycosides were isolated from the roots of Pulsatilla chinensis (Bunge) Regel (Ranunculaceae). Two new glycosides, chinensiosides A (1a) and B (2), were identified as 3-O-[α-L-rhamnopyranosyl-(1→ 2)-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→4) -β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]-3β, 23-dihydroxylup-20(29)-en-28-oic acid and 3-O-{α -L-rhamnopyranosyl-(1→-2)-[β-D-glucopyranosyl-(1→4)] -α-L-arabinopyranosyl}-28-O-[α-L-rhamnopyranosyl-(1→4) -β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]-3β, 23-dihydroxylup-20(29)-en-28-oic acid. The other two glycosides were identified as previously known hederasaponin C (3) from Hedera helix and glycoside III (4) from Pulsatilla cernua.
- Glebko,Krasovskaj,Strigina,Ulanova,Denisenko,Dmitrenok
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p. 1945 - 1950
(2007/10/03)
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- Triterpenoids from Pulsatilla chinensis
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A new lupane type triterpenic acid, pulsatillic acid, and two new lupane type triterpenoid glycosides, pulsatilloside A and B, along with the known 23-hydroxybetulinic acid were isolated from the roots of Pulsatilla chinensis. Their structures were characterized as 3-oxo-23-hydroxy-lup- 20(29)-en-28-oic acid, 3β, 23-dihydroxy-lup-20(29)-en-28-oic acid 3-O-α-L- arabinopyranoside and 3β, 23-dibydroxy-lup-20(29)-en-28-oic acid 28-O-β-D- glucopyranosyl-(1→6)-β-D-glucopyranoside on the basis of hydrolysis and spectral evidence including two-dimensional relay HOHAHA, one-dimensional multiple relay COSY and ROESY NMR techniques. Pulsatillic acid exhibited cytotoxic activities against P-388, Lewis lung carcinoma and human large- cell lung carcinoma.
- Ye, Wen-Cai,Ji, Nine-Ning,Zhao, Shou-Xun,Liu, Jing-Han,Ye, Tao,McKervey,Stevenson
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p. 799 - 802
(2007/10/03)
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