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从 Roxb. 心材精油中分离出的 - 贝叶 -15- 烯 -19- 醛的自动氧化：15,16- 环氧 - - 贝叶烷 -19- 酸及其他产物的形成。

Auto-oxidation of -beyer-15-en-19-al isolated from the essential oil of the heartwood of Roxb.: formation of 15,16-epoxy--beyeran-19-oic acid and other products.

作者信息

Tennakoon T M Samantha Gome, Gunaherath G M Kamal Bandara, De Silva K Tuley Dayananda, Padumadasa Chayanika, Wijesundara D Siril Abeywickrama, Abeysekera Ajita Mahendra

机构信息

Research and Development Laboratory, Link Natural Products Pvt. Ltd. Malinda, Kapugoda, Sri Lanka.

2Department of Chemistry, Open University of Sri Lanka, P. O. Box 21, Nugegoda, Sri Lanka.

出版信息

BMC Chem. 2020 Mar 13;14(1):18. doi: 10.1186/s13065-020-00671-9. eCollection 2020 Dec.

DOI:10.1186/s13065-020-00671-9
PMID:32190844
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7071572/
Abstract

Chemical investigation of the essential oil obtained from the heartwood of Roxb. yielded three beyerene type diterpenoids -beyer-15-ene (), -beyer-15-en-19-ol (erythroxylol A) () and -beyer-15-en-19-al (). -beyer-15-en-19-al () was found to be unstable at room temperature, giving rise to hitherto unknown 15,16-epoxy--beyeran-19-oic acid (). This conversion involves the auto-oxidation of a C-4 axial aldehyde group of an -beyer-15-ene diterpenoid with the concurrent epoxidation of the C-15 double bond. This is the first report of the auto-oxidation of an aldehyde group to a carboxylic acid group with the concurrent epoxidation of a double bond in the same compound. Further investigation of this observation under controlled conditions resulted in the isolation and identification of -beyer-15-en-19-oic acid (), two new epoxy hydroperoxides, 15,16-epoxy-19---beyeran-4-hydroperoxide (), 15,16-epoxy-18---beyeran-4-hydroperoxide (), and two new hydroperoxides, -beyer-19--15-en-4-hydroperoxide (), -beyer-18--15-en-4-hydroperoxide () and -beyer-18--15-en-4-ol (). Identification of these compounds was carried out by the extensive usage of spectroscopic data including 1D and 2D NMR. The acid and the alcohol have been reported previously as natural products from and . The mechanistic basis of this auto-oxidation reaction is discussed.

摘要

对从 Roxb. 心材中提取的精油进行化学研究，得到了三种贝壳杉烯型二萜类化合物——贝壳杉-15-烯（）、贝壳杉-15-烯-19-醇（赤藓醇 A）（）和贝壳杉-15-烯-19-醛（）。发现贝壳杉-15-烯-19-醛（）在室温下不稳定，会生成迄今未知的 15,16-环氧-贝壳杉烷-19-酸（）。这种转化涉及贝壳杉-15-烯二萜类化合物 C-4 轴向醛基的自动氧化，同时 C-15 双键发生环氧化。这是同一化合物中醛基自动氧化为羧基并同时双键环氧化的首次报道。在可控条件下对这一现象进行进一步研究，分离并鉴定出贝壳杉-15-烯-19-酸（）、两种新的环氧氢过氧化物，15,16-环氧-19-贝壳杉烷-4-氢过氧化物（）、15,16-环氧-18-贝壳杉烷-4-氢过氧化物（），以及两种新的氢过氧化物，贝壳杉-19-贝壳杉-15-烯-4-氢过氧化物（）、贝壳杉-18-贝壳杉-15-烯-4-氢过氧化物（）和贝壳杉-18-贝壳杉-15-烯-4-醇（）。这些化合物的鉴定通过广泛使用包括一维和二维核磁共振在内的光谱数据进行。酸（）和醇（）此前已作为从 和 中分离得到的天然产物被报道过。本文讨论了这种自动氧化反应的机理基础。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/5c4524cb2bd0/13065_2020_671_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/3a4230090b42/13065_2020_671_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/66416974dea0/13065_2020_671_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/31d5f3d12d0f/13065_2020_671_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/ed4275afdcaa/13065_2020_671_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/e602b7efb533/13065_2020_671_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/d63a6b45ddce/13065_2020_671_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/49d34e1d9636/13065_2020_671_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/5c4524cb2bd0/13065_2020_671_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/3a4230090b42/13065_2020_671_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/66416974dea0/13065_2020_671_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/31d5f3d12d0f/13065_2020_671_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/ed4275afdcaa/13065_2020_671_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/e602b7efb533/13065_2020_671_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/d63a6b45ddce/13065_2020_671_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/49d34e1d9636/13065_2020_671_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b763/7071572/5c4524cb2bd0/13065_2020_671_Sch2_HTML.jpg

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Geopyxins A-E, ent-kaurane diterpenoids from endolichenic fungal strains Geopyxis aff. majalis and Geopyxis sp. AZ0066: structure-activity relationships of geopyxins and their analogues.地椒菌素 A-E，内生真菌 Geopyxis aff. majalis 和 Geopyxis sp. AZ0066 来源的贝壳杉烷二萜：地椒菌素及其类似物的结构-活性关系。
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