Sukandar Edwin R, Mulya Fadjar, Parasuk Vudhichai, Phuwapraisirisan Preecha, Rassamee Kitiya, Siripong Pongpun, Kaennakam Sutin
Department of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkut's University of Technology North Bangkok (KMUTNB), Bangkok 10800, Thailand.
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Bandung Institute of Technology, Bandung 40132, Indonesia.
ACS Omega. 2024 Oct 16;9(43):43689-43696. doi: 10.1021/acsomega.4c06030. eCollection 2024 Oct 29.
Polyprenylated benzoylphloroglucinols (PPBPs) make up a group of complex natural products with anticancer potentials that are mainly distributed in plants. As part of our intensive exploration on new bioactive substances from this genus, we report two undescribed PPBPs, picrorhizones I () and J (), along with four known analogues (-) from the stem bark of and . The new structures were elucidated on the basis of spectroscopic analysis, particularly 1D and 2D NMR and HRESIMS, whereas the absolute configurations were determined by a combination of ECD and NMR calculations coupled with a DP4+ probability analysis. Being the least class in genus , picrorhizone I possesses a type-A structure with the position of a benzoyl moiety attaching to one of the bridgehead carbons of a bicyclo[3.3.1]nonane skeleton, which differs from its major type-B counterparts. This work also represents the first report on the occurrence of PPBPs in . The cytotoxic evaluation of the isolated compounds revealed that isogarcinol () and garciyunnanin L () significantly inhibited the growth of KB and Hela S3 cancer cells with IC values lower than 10 μM, while was also strongly active against the Hep G2 cancer cell line with an IC value of 8.02 μM. Among the B-class derivatives bearing a lavandulyl side chain, cyclization of the moiety in the bicyclic phloroglucinol skeleton enhanced the cytotoxic properties on cancer cells.
多异戊烯基化苯甲酰基间苯三酚（PPBPs）是一类具有抗癌潜力的复杂天然产物，主要分布于植物中。作为我们对该属新生物活性物质深入探索的一部分，我们报道了两种未描述的PPBPs，胡黄连酮I（）和J（），以及从和的茎皮中分离得到的四种已知类似物（-）。新结构通过光谱分析得以阐明，特别是一维和二维核磁共振以及高分辨电喷雾电离质谱，而绝对构型则通过电子圆二色谱和核磁共振计算相结合，并结合DP4 +概率分析来确定。作为属中最少见的类别，胡黄连酮I具有A型结构，其苯甲酰基部分连接在双环[3.3.1]壬烷骨架的一个桥头碳上，这与主要的B型对应物不同。这项工作也是关于PPBPs在中存在的首次报道。对分离得到的化合物进行的细胞毒性评估显示，异藤黄醇（）和藤黄云南素L（）显著抑制KB和Hela S3癌细胞的生长，IC值低于10μM，而对Hep G2癌细胞系也具有较强活性，IC值为8.02μM。在带有薰衣草基侧链的B类衍生物中，双环间苯三酚骨架中部分的环化增强了对癌细胞的细胞毒性。
