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Isolation of the diterpenoids, ent-kauran-16alpha-ol and ent-atisan-16alpha-ol, from sunflowers, as oviposition stimulants for the banded sunflower moth, Cochylis hospes.从向日葵中分离出二萜类化合物对映贝壳杉烷-16α-醇和对映阿替生烷-16α-醇,作为条带向日葵螟(Cochylis hospes)的产卵刺激剂。
J Chem Ecol. 2005 Jan;31(1):89-102. doi: 10.1007/s10886-005-0976-2.
4
Total syntheses of (-)-methyl atis-16-en-19-oate, (-)-methyl kaur-16-en-19-oate, and (-)-methyl trachyloban-19-oate by a combination of palladium-catalyzed cycloalkenylation and homoallyl-homoallyl radical rearrangement.通过钯催化环烯基化和高烯丙基-高烯丙基自由基重排相结合的方法全合成(-)-atis-16-烯-19-酸甲酯、(-)-kaur-16-烯-19-酸甲酯和(-)-trachyloban-19-酸甲酯。
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Identification of ent-16 beta, 17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa.从番荔枝中鉴定出对映-16β,17-二羟基贝壳杉烷-19-酸作为抗HIV成分并分离出新的二萜类化合物番荔枝鳞叶素A和B。
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Isolation and identification of trachyloban-19-oic and (-)-kaur-16-en-19-oic acids as antimicrobial agents from the prairie sunflower, Helianthus annuus.从草原向日葵(向日葵)中分离并鉴定出trachyloban - 19 - 酸和(-)- 贝壳杉 - 16 - 烯 - 19 - 酸作为抗菌剂。
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从向日葵中分离出三种二萜酸,作为条带向日葵螟(Cochylis hospes)的产卵刺激剂。

Isolation of three diterpenoid acids from sunflowers, as oviposition stimulants for the banded sunflower moth, Cochylis hospes.

作者信息

Morris Bruce D, Charlet Laurence D, Foster Stephen P

机构信息

Department of Entomology, North Dakota State University, Fargo, 58105, USA.

出版信息

J Chem Ecol. 2009 Jan;35(1):50-7. doi: 10.1007/s10886-008-9567-3. Epub 2008 Dec 18.

DOI:10.1007/s10886-008-9567-3
PMID:19093152
Abstract

The banded sunflower moth (BSFM), Cochylis hospes Walshingham (Lepidoptera: Cochylidae) is a specialist insect, the larvae of which feed on sunflowers, Helianthus spp., and a few other species of Compositae. It is one of the most important pests of sunflower in the USA. Previous work on H. annuus, the cultivated sunflower, revealed two diterpenoids that function as oviposition stimulants for female BSFM, and that other, more polar compounds also stimulated oviposition. Using a bioassay-guided approach, we isolated three additional diterpenoids, grandifloric acid (1), 15beta-hydroxy-ent-trachyloban-19-oic acid (2), and 17-hydroxy-16alpha-ent-kauran-19-oic acid (3), from polar fractions of pre-bloom sunflower head extracts. In laboratory bioassays, purified natural samples of each of these compounds stimulated oviposition by female BSFM. Structure-activity relationships of the five diterpenoids known to stimulate oviposition by female BSFM are discussed.

摘要

带状向日葵螟(BSFM),即向日葵曲茎螟(Cochylis hospes Walshingham,鳞翅目:曲茎螟科),是一种专食性昆虫,其幼虫以向日葵属植物向日葵以及其他几种菊科植物为食。它是美国向日葵最重要的害虫之一。此前对栽培向日葵向日葵的研究发现了两种二萜类化合物,它们是雌性带状向日葵螟产卵的刺激物,并且其他极性更强的化合物也能刺激产卵。我们采用生物测定导向的方法,从开花前向日葵花盘提取物的极性部分中分离出了另外三种二萜类化合物,大花酸(1)、15β-羟基-对映-刺槐烷-19-酸(2)和17-羟基-16α-对映-贝壳杉烷-19-酸(3)。在实验室生物测定中,这些化合物的纯化天然样品均能刺激雌性带状向日葵螟产卵。本文讨论了已知能刺激雌性带状向日葵螟产卵的五种二萜类化合物的构效关系。