Metabolome of the Phyllidiella pustulosa Species Complex (Nudibranchia, Heterobranchia, Gastropoda) Reveals Rare Dichloroimidic Sesquiterpene Derivatives from a Phylogenetically Distinct and Undescribed Clade.,Journal of Natural Products

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Metabolome of the Phyllidiella pustulosa Species Complex (Nudibranchia, Heterobranchia, Gastropoda) Reveals Rare Dichloroimidic Sesquiterpene Derivatives from a Phylogenetically Distinct and Undescribed Clade.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-09-10 , DOI: 10.1021/acs.jnatprod.0c00783
Alexander Bogdanov _{1,

2} , Adelfia Papu _{3,

4} , Stefan Kehraus ₁ , Max Cruesemann ₁ , Heike Wägele ₃ , Gabriele M König ₁

Affiliation

Phyllidiid nudibranchs are brightly colored gastropod mollusks, frequently encountered in coral reefs of the tropical Indo-Pacific. The lack of a protective shell is suggested to be compensated by toxic secondary metabolites that are sequestered from specific prey sponges. Our ongoing reconstruction of phyllidiid phylogeny using molecular data of more than 700 specimens, based on published data and newly collected specimens in various seasons and localities around North Sulawesi (Indonesia), demonstrates that Phyllidiella pustulosa is a species complex with at least seven well-supported clades. A metabolomic analysis of 52 specimens from all seven clades of P. pustulosa was performed. Secondary metabolite profiles were found to correlate with the phylogenetic study and not the prevailing food sponges as expected. GNPS molecular networking revealed a unique chemotype in clade 6. Detailed chemical analysis of a specimen from this chemically and genetically distinct P. pustulosa clade led to the identification of seven new sesquiterpenoids with a rare dichloroimidic moiety (1 and 4) and derivatives thereof (2, 3, 5–7). Our findings suggest that P. pustulosa clades should be raised to the species level.

中文翻译：

Phyllidiella pustulosa 物种复合体（裸鳃亚目、异鳃亚目、腹足纲）的代谢组揭示了来自系统发育不同且未描述的进化枝的稀有二氯亚胺倍半萜衍生物。

Phyllidiid 裸鳃类动物是颜色鲜艳的腹足类软体动物，经常出现在热带印度洋-太平洋的珊瑚礁中。建议通过从特定猎物海绵中隔离的有毒次级代谢物来补偿缺乏保护壳。我们正在使用 700 多个标本的分子数据重建 phyllidiid 系统发育，基于已发表的数据和在北苏拉威西岛（印度尼西亚）周围不同季节和地区新收集的标本，表明Phyllidiella pustulosa是一个物种复合体，至少有七个得到充分支持的物种。进化枝。来自P. pustulosa 的所有七个进化枝的 52 个标本的代谢组学分析进行了。发现次生代谢物谱与系统发育研究相关，而不是如预期的那样与流行的食物海绵相关。GNPS 分子网络揭示了进化枝 6 中独特的化学型。对来自这种化学和遗传上不同的P. pustulosa进化枝的样本进行详细的化学分析，鉴定了七种具有稀有二氯亚胺基部分（1和4）及其衍生物（2）的新倍半萜类化合物。, 3 , 5 – 7 )。我们的研究结果表明P. pustulosa进化枝应该提升到物种水平。

更新日期：2020-09-25

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