Surup Frank, Kuhnert Eric, Liscinskij Elena, Stadler Marc
Department Microbial Drugs, Helmholtz Centre for Infection Research GmbH, Inhoffenstraße 7, 38124, Braunschweig, Germany.
Nat Prod Bioprospect. 2015 Jun;5(3):167-73. doi: 10.1007/s13659-015-0065-3. Epub 2015 Jun 16.
A culture isolated from ascospores of Hypoxylon rickii, a xylariaceous ascomycete collected in Martinique, had yielded botryane, noreremophilane and abietane-type terpenoids in a preceding study, but additional metabolites were detected by extensive HPLC-MS analysis in other fractions. Herein we report the further isolation of four new sesquiterpenoids with a silphiperfol-6-ene skeleton from extracts of H. rickii. The planar structures were elucidated by NMR and HRMS data as 13-hydroxysilphiperfol-6-ene (1), 9-hydroxysilphiperfol-6-en-13-oic acid (2), 2-hydroxysilphiperfol-6-en-13-oic acid (3) and 15-hydroxysilphiperfol-6-en-13-oic acid (4). For compounds 2-4 we propose the trivial names rickinic acids A-C. Their stereochemistry was assigned by ROESY correlations as well as by the specific optical rotation. Additionally, the known compounds, botryenanol, dehydrobotrydienol, cyclo(Phe-Pro), cyclo(Pro-Leu), (+)-ramulosin and α-eleostearic acid were isolated. The antimicrobial and cytotoxic activities of the new compounds are also reported.
从采集于马提尼克岛的炭角菌科子囊菌里克拟炭角菌（Hypoxylon rickii）的子囊孢子中分离出的一种培养物，在之前的一项研究中产生了葡萄烷型、降瑞香烷型和枞酸型萜类化合物，但通过广泛的高效液相色谱 - 质谱分析在其他馏分中检测到了额外的代谢产物。在此，我们报告从里克拟炭角菌提取物中进一步分离出四种具有半日花-6-烯骨架的新倍半萜类化合物。通过核磁共振（NMR）和高分辨质谱（HRMS）数据确定平面结构为13-羟基半日花-6-烯（1）、9-羟基半日花-6-烯-13-酸（2）、2-羟基半日花-6-烯-13-酸（3）和15-羟基半日花-6-烯-13-酸（4）。对于化合物2 - 4，我们提出俗名里克拟炭角菌酸A - C。它们的立体化学通过旋转相关光谱（ROESY）相关性以及比旋光度确定。此外，还分离出了已知化合物葡萄烯醇、脱氢葡萄二烯醇、环（苯丙 - 脯）二肽、环（脯 - 亮）二肽、（+）-拉穆洛辛和α-桐酸。还报道了新化合物的抗菌和细胞毒性活性。
