30-Nor-3.beta.-methoxyserrat-14-en-21-one: first reported natural occurrence of a norserratene triterpene

Conner, Anthony H.; Haromy, T. P.; Sundaralingam, M.

doi:10.1021/jo00327a035

Cited by 23 publications

(11 citation statements)

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“…Of importance is the detection of compounds 3, 5, 10, 11, 3,21-dimethoxy-serrat-14-ene, 21-methoxy-serrat-14-en-3-ol, 3-methoxyserrat-14-ene-21,29-diol, 3-methoxy-serrat-14-en-21,29-diol, 3-methoxy-serrat-14-ene-21,30-diol and 29-nor-3-methoxy-serrat-14-en-21-one in Pinus monticola Doug. (Pinus albicaulis, Western White Pine or Douglas Pine; Rowe et al, 1972;Conner et al, 1980Conner et al, , 1981 insu-00759832, version 1 -3 Dec 2012…”

Section: Pinusmentioning

confidence: 99%

Methoxy-serratenes in a soil under conifers and their potential use as biomarkers of Pinaceae

Milbeau

Lavrieux

Jacob

et al. 2013

Organic Geochemistry

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International audienceIn the frame of a study aimed at defining new soil molecular biomarkers that could attest to former land use and that could also be screened in lake sediments for palaeoenvironmental reconstruction, we analysed the 2-4 cm depth layer of a soil developed under a conifer forest in the Lake Aydat catchment (French Massif Central). The lipid fraction of the sample contained 12 serratenoids bearing at least a methoxyl (OMe) group at C-3 or C-21 and various additional functional groups (alcohol, ketone or acetate). A survey of the literature provided indubitable evidence that these compounds are typical for Pinaceae species, in agreement with the surrounding vegetation at the sampling site. Due to the economic and ecological importance of the taxa, the presence of these highly specific compounds in soil, sediments or peat should therefore help in unravelling the timing of forestry activity

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Section: Pinusmentioning

confidence: 99%

Methoxy-serratenes in a soil under conifers and their potential use as biomarkers of Pinaceae

Milbeau

Lavrieux

Jacob

et al. 2013

Organic Geochemistry

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“…In the NOESY plot, significant NOEs were observed between the aldehyde proton and H b ÀC(16), H b ÀC(27), and Me(26), which suggested the b-position of the aldehyde group. NOEs were not observed for HÀC(3)/Me(23) and H a ÀC(5), indicating that HÀC(3) has the axial b-configuration. Finally, the EI-MS of 3 showed eight predominant fragment-ion peaks due to cleavage of the C-and D-ring at m/z 409, 231, 203, 223, 205, 154, 136, and 121.This work was supported by the NKIP Foundation of the Chinese Academy of Sciences (KSCZX-SW-301-08) and the Foundation of Key State Lab of Phytochemistry.…”

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confidence: 97%

“…Plants of the genus characteristically contain triterpenoids of the serratene group or derivatives of its biogenetic precursor, a-onocerin [4]. Serratenes constitute a group of naturally occurring pentacyclic triterpenoids possessing seven tertiary Me groups and a seven-membered ring C, usually with a CC bond between C (14) and C (15) and O-functionalities at C(3) and C(21) [5]. L. japonicum was shown to occur in the Chinese provinces Guangdong, Guangxi, Yunnan, and Guizhou [6].…”

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confidence: 99%

Three New Triterpenoids fromLycopodium japonicumThunb

Jian

Zhang

et al. 2005

HCA

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“…scattering factors (Main, 1975) based on a/I TM serratene skeleton which was previously assumed for this structure (and later shown to be incorrect) based on chemical and spectral work (Conner et aL, 1981). A total of 347 reflections with E values greater than 1.4 were used for the structure determination.…”

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confidence: 99%

“…Discussion. The final positional parameters are given in Table 1.t An ORTEP drawing (Johnson, 1976)of the title compound is given in Conner et al (1981). The + Lists of structure factors and anisotropic thermal parameters and a packing diagram of the title compound have been deposited with the British Library Lending Division as Supplementary Publication No.…”

mentioning

confidence: 99%