Two new prenylated phloroglucinol derivatives from <i>Hypericum scabrum</i>

Yang, Jian‐Bo; Liu, Rangdong; Ren, Jin; Qian, Wei; Wang, Aiguo; Su, Ya‐Lun

doi:10.1080/10286020.2015.1123693

Cited by 13 publications

(7 citation statements)

References 12 publications

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“…Accordingly, the reported structures of garcinielliptones L and M (4 and 5) should also be revised to 4a and 5a, respectively, given their coisolation with 3. Their C-1−C-10 chemical shifts (Table 4) matched those of furoadhyperforin isomer 2b (8) (Figure 3), 31 a known PPAP with the same core carbon skeleton as was established by X-ray diffraction data (CCDC 1473752, Figure 4). The consistency also supported the correctness of the revised structures 4a and 5a.…”

Section: ■ Results and Discussionsupporting

confidence: 58%

“…Two structurally well-defined PPAPs, hyperibrin C ( 7 ) and sampsonione M ( 11 ), , were used to confirm the structures of 3a and 6a , respectively. In addition, furoadhyperforin isomer 2b ( 8 ), a PPAP whose structure was confirmed by X-ray diffraction data, isolated from Hypericum cohaerens , was utilized to further support the carbon skeletons of 4a and 5a .…”

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confidence: 99%

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Skeleton Reassignment of Type C Polycyclic Polyprenylated Acylphloroglucinols

Yang

2016

J. Nat. Prod.

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The previous assignment of the type C skeleton of polycyclic polyprenylated acylphloroglucinols (PPAPs) was controversial and proved to be incorrect in this study. The structures of the type C PPAPs (3-6) were revised to corresponding type A structures (3a-6a) via C NMR spectroscopic analysis and a quantum computational chemistry method. Therefore, only types A and B PPAPs are likely present in plants of the family Clusiaceae.

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Section: ■ Results and Discussionsupporting

confidence: 58%

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confidence: 99%

Skeleton Reassignment of Type C Polycyclic Polyprenylated Acylphloroglucinols

Yang

2016

J. Nat. Prod.

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“…In order to see whether we could formulate a rule that would allow us to quickly discern whether a new furan-fused PPAP was type A or B, we tabulated certain 1 H and 13 C chemical shifts of 27 furan-fused type A PPAPs and seven furan-fused type B PPAPs that had been reported previously (Table , in CDCl 3 ). ,,− The chemical shifts of C-4 in the furan-fused type A PPAPs ranged from 188.1 to 191.2, whereas they ranged from 193.9 to 196.6 ppm in the type B analogs. Furthermore, the difference in chemical shifts of the two H-17 protons (Δδ-H-17) ranged from 0.00 to 0.26 in the type A structures, whereas it ranged from 0.53 to 0.75 ppm in the type B analogs.…”

Section: Resultsmentioning

confidence: 99%

Structure Revision of Type B Polycyclic Polyprenylated Acylphloroglucinols Fused to a Partly Reduced Furan Ring

Qiu,

Grossman,

Yang

2023

J. Nat. Prod.

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Four previous papers reported the isolation and structural determination of 10 polycyclic polyprenylated acylphloroglucinols (PPAPs), uraliones F, G, K, and O, attenuatumiones E and F, and scabrumiones A−D, from Hypericum species. Their structures were identified as type B PPAPs that featured not only the characteristic acyl group at C-3 of the bicyclo[3.3.1]nonane core but also a partly reduced furan ring fused to the C-1−C-2−O-2 atoms of the core. However, the 1D and 2D NMR data of these compounds were more consistent with type A PPAPs that featured not only the acyl group at C-1 but also a partially reduced furan ring fused to the C-3−C-2−O-2 atoms of the core. Now we revise these 10 previously proposed structures to the corresponding type A PPAPs via NMR analysis. Additionally, we propose a rule that uses NMR data to determine whether a particular PPAP that is fused to a partly reduced furan ring at C-3−C-2−O-2 or C-1−C-2−O-2 is type A or type B, respectively. We also propose a rule to assign the relative configurations of corresponding type A PPAPs at C-18 and revise the configurations of sampsonione N, hypericumoxides A−C, and hyperscabin G.

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“…As shown in Table , this subclass includes 114 BPAPs in which the acyl group is located at the C-1 position. Interestingly, the majority of the type A BPAPs (102 members) are obtained from the genus Hypericum . ,,,,,,, The vast majority, compounds 1 – 112 , share a common bicyclo[3.3.1]nonane-2,4,9-trione core. By contrast, hypercohin A ( 113 ) possesses an unusual bicyclo[5.3.1]hendecane core.…”

Section: Classification Of Diverse Ppapsmentioning

confidence: 99%

Research Progress of Polycyclic Polyprenylated Acylphloroglucinols

2018

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Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of hybrid natural products sharing the mevalonate/methylerythritol phosphate and polyketide biosynthetic pathways and showing considerable structure and bioactivity diversity. This review discusses the progress of research into the chemistry and biological activity of 421 natural PPAPs in the past 11 years as well as in-depth studies of biological activities and total synthesis of some PPAPs isolated before 2006. We created an online database of all PPAPs known to date at http://www.chem.uky.edu/research/grossman/PPAPs . Two subclasses of biosynthetically related metabolites, spirocyclic PPAPs with octahydrospiro[cyclohexan-1,5'-indene]-2,4,6-trione core and complicated PPAPs produced by intramolecular [4 + 2] cycloadditions of MPAPs, are brought into the PPAP family. Some PPAPs' relative or absolute configurations are reassigned or critically discussed, and the confusing trivial names in PPAPs investigations are clarified. Pharmacologic studies have revealed a new molecular mechanism whereby hyperforin and its derivatives regulate neurotransmitter levels by activating TRPC6 as well as the antitumor mechanism of garcinol and its analogues. The antineoplastic potential of some type B PPAPs such as oblongifolin C and guttiferone K has increased significantly. As a result of the recent appearances of innovative synthetic methods and strategies, the total syntheses of 22 natural PPAPs including hyperforin, garcinol, and plukenetione A have been accomplished.

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Two new prenylated phloroglucinol derivatives from Hypericum scabrum

Abstract: Two new prenylated phloroglucinol derivatives (1-2), and a known compound furohyperforim isomer 2 (3), were isolated from the aerial parts of Hypericum scabrum. Their structures were elucidated by various spectroscopic methods, including MS, IR, UV, and NMR.

Cited by 13 publications

References 12 publications

Skeleton Reassignment of Type C Polycyclic Polyprenylated Acylphloroglucinols

Skeleton Reassignment of Type C Polycyclic Polyprenylated Acylphloroglucinols

Structure Revision of Type B Polycyclic Polyprenylated Acylphloroglucinols Fused to a Partly Reduced Furan Ring

Research Progress of Polycyclic Polyprenylated Acylphloroglucinols

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