Seco B-Type Oligomers from Pinus massoniana Expand the Procyanidin Chemical Space and Exhibit Dental Bioactivity
文献类型：期刊论文
| 作者 | Zhou, Bin1,2,3; Alania, Yvette4,5; Reis, Mariana4,5; Jing, Shu-Xi1,2; McAlpine, James B.1,2; Bedran-Russo, Ana K.4,5; Chen, Shao-Nong1,2; Ferreira, Daneel6,7; Pauli, Guido F.1,2 |
| 刊名 | JOURNAL OF NATURAL PRODUCTS
 |
| 出版日期 | 2022-11-16 |
| 页码 | 16 |
| ISSN号 | 0163-3864 |
| DOI | 10.1021/acs.jnatprod.2c00664 |
| 通讯作者 | Pauli, Guido F.(gfp@uic.edu) |
| 英文摘要 | Investigation of a pine bark extract for bioactive proanthocyanidin oligomers resulted in the isolation of structurally related dimeric seco B-type procyanidin derivatives, 1-5. This includes scalemic mixtures of gambiriin A1 (1a) and A2 (2a) and their newly described optical antipodes, ent-gambiriin A1 (1b) and ent-gambiriin A2 (2b), respectively, as well as a racemic mixture of the newly described (ent-)gambiriin A5 (3a/3b). Furthermore, the study now fully characterizes the previously reported optically pure dimers gambiriin B1 (4) and gambirflavan D1 (5), and characterized the novel seco B-type procyanidin trimer, 6 (gambirifuran C1). Thermal conversion of catechin in aqueous solution provided further evidence for the structures of 1-6 and led to the purification of semisynthetic 1a and 2a as well as additional dimers 7-10. Elucidating the structures of the natural dimers, 1-5, from comprehensive NMR and ECD data and synthetic evidence provided crucial reference points for establishing the structure of the seco B-type procyanidin trimer, 6. Serving as assigned building blocks, data from the dimers supported the 3D structural assignment of 6 based on NMR substituent chemical shift differences (s.c.s., syn. Delta delta C) and component-based empirical ECD calculations. Within the newly characterized series of PAC related molecules, 5 exhibited high dentin biomodification potential. In addition, considering the nomenclature issues and plausible biosynthetic pathways of this group of compounds led to a consolidated nomenclature of all currently known seco B-type procyanidins. These findings, thereby, expand the chemical space of bioactive catechin oligomers, which have promise as agents for the natural enhancement of dental biomaterials. Finally, the current knowledge of the chemical space of seco B-type procyanidin derivatives was compiled to the level of absolute configuration. |
| WOS关键词 | CHALCAN-FLAVAN DIMERS ; ABSOLUTE-CONFIGURATION ; PROANTHOCYANIDINS ; GAMBIR ; TANNINS |
| 资助项目 | NIDCR/NIH[R01 DE021040] ; NIGMS[P41 GM068944] |
| WOS研究方向 | Plant Sciences ; Pharmacology & Pharmacy |
| 语种 | 英语 |
| 出版者 | AMER CHEMICAL SOC |
| WOS记录号 | WOS:000890478300001 |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/304542]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Pauli, Guido F. |
| 作者单位 | 1.Univ Illinois, Pharmacognosy Inst, Coll Pharm, Chicago 60612, IL USA 2.Univ Illinois, Coll Pharm, Dept Pharmaceut Sci, Chicago, IL 60612 USA 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China 4.Univ Illinois, Coll Dent, Dept Restorat Dent, Chicago, IL 60612 USA 5.Marquette Univ, Sch Dent, Dept Gen Dent Sci, Milwaukee, WI 53233 USA 6.Univ Mississippi, Natl Ctr Nat Prod Res, Sch Pharm, University, MS 38677 USA 7.Univ Mississippi, Sch Pharm, Dept Biomol Sci, Div Pharmacognosy, University, MS 38677 USA |
| 推荐引用方式 GB/T 7714 | Zhou, Bin,Alania, Yvette,Reis, Mariana,et al. Seco B-Type Oligomers from Pinus massoniana Expand the Procyanidin Chemical Space and Exhibit Dental Bioactivity[J]. JOURNAL OF NATURAL PRODUCTS,2022:16. |
| APA | Zhou, Bin.,Alania, Yvette.,Reis, Mariana.,Jing, Shu-Xi.,McAlpine, James B..,...&Pauli, Guido F..(2022).Seco B-Type Oligomers from Pinus massoniana Expand the Procyanidin Chemical Space and Exhibit Dental Bioactivity.JOURNAL OF NATURAL PRODUCTS,16. |
| MLA | Zhou, Bin,et al."Seco B-Type Oligomers from Pinus massoniana Expand the Procyanidin Chemical Space and Exhibit Dental Bioactivity".JOURNAL OF NATURAL PRODUCTS (2022):16. |
入库方式： OAI收割
来源：上海药物研究所
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