Hyperfols A and B: Two Highly Modified Polycyclic Polyprenylated Acylphloroglucinols from <i>Hypericum perforatum</i>

Lou, Hua‐Yong; Li, Yanan; Yi, Ping; Jian, Jun-You; Hu, Zhan-Xing; Gu, Wei; Huang, Liejun; Li, Yanmei; Yuan, Chun‐Mao; Hao, Xiao‐Jiang

doi:10.1021/acs.orglett.0c02434

Cited by 27 publications

(20 citation statements)

References 19 publications

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“…[ 11‐15 ] Hypericum monogynum Linn was used as a traditional Chinese medicine for the treatment of hepatitis, conjunctivitis, acute laryngopharyngitis, and snake bites. [ 16 ] During our continuous research for structurally novel and biologically valuable PPAPs, [ 17‐19 ] eleven biogenetically related polyprenylated acylphloroglucinols (PPAPs) with diverse structures (Figure 1), including four novel PPAPs ( 1 — 4 ) and five new compounds ( 5 — 9 ), were isolated from the flowers of H. monogynum . Three compounds ( 5 , 6 , and 9 ) showed a stronger reversal effect than positive control verapamil in adriamycin (ADR) resistant human hepatocellular carcinoma cell line HepG2 (HepG2/ADR) and ADR resistant human breast adenocarcinoma cell line MCF‐7 (MCF‐7/ADR).…”

Section: Background and Originality Contentmentioning

confidence: 99%

Hypermonones A—I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity

Zeng

Yang

et al. 2021

Chin. J. Chem.

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Main observation and conclusion Eleven biogenetically related polyprenylated acylphloroglucinols (PPAPs), including four novel skeletons (1—4) and five new compounds (5—9), were isolated from the flowers of Hypericum monogynum. Hypermonones A—D (1—4) represented the first example of a unique dilactone structure containing carbonyl bonded single δ‐lactone and tricyclic γ‐lactone moieties. Their structures were elucidated by NMR analysis, X‐ray crystallography, and ECD calculations. Moreover, we revised the structure of hyperibrin B to hypermonone I (9) via NMR analysis, a quantum computational chemistry method, and hypothetic biosynthetic considerations. Three compounds (5, 6, and 9) with significant MDR reversal activity (RF ranging from 61 to 223) were superior to the positive control verapamil (MCF‐7/ADR, RF: 53; HepG2/ADR, RF: 124). Mechanism study for compound 5 indicated that this compound could inhibit the function of P‐gp transport rather than its expression, and the possible recognition mechanism between compound 5 and P‐gp was predicted by molecular docking.

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Section: Background and Originality Contentmentioning

confidence: 99%

Hypermonones A—I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity

Zeng

Yang

et al. 2021

Chin. J. Chem.

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“…To seek a better solution, CASE systems were used to generate a set of all possible structures based on empirical NMR chemical shift predictions. − As shown in Figure , four possible structures were generated in 1.0 s and ranked by 13 C average deviations [ d A ( 13 C), d N ( 13 C), and d N ( 13 C + 1 H)]. The top hit structure (ID = 1) might be the best-matched structure of 1 due to the lowest standard deviation values.…”

Section: Results and Discussionmentioning

confidence: 99%

Three Unusual Sesquiterpenes with Distinctive Ring Skeletons from Daphne penicillata Uncovered by Molecular Networking Strategies

Zhao

Qin

et al. 2021

J. Org. Chem.

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Daphnenoids A−C (1−3), three unusual sesquiterpenes with distinctive ring skeletons, together with a biogenetically related daphnenoid D (4) were obtained from the herb of Daphne penicillata by molecular networking strategies. Daphnenoid A (1) possesses a unique caged tetracyclo [5.3.2.0 1 , 6 .0 4 , 11 ] dodecane scaffold by unexpected cyclizations of C-1/C-11 and C-2/C-14. Daphnenoids B and C (2 and 3) were the first discovered natural sesquiterpenes with unique 5/5 spirocyclic systems in nature. Their structures were determined by NMR spectroscopic analysis, computer-assisted structure elucidation methods, quantum chemical calculations, and X-ray diffraction. A hypothetical biogenetic pathway begins with typical guaiane sesquiterpene (a), including a key intermediate (4) was proposed. Daphnenoids B and C (2 and 3) exhibited potential inhibitory activities on the production of NO against LPS-induced BV2 microglial cells.

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“…nor -BPAP derivatives are a microcommunity of PPAPs, which were considered to be biosynthesized from the common BPAPs through degradation of C-2, C-2/3, C-2/3/4, C-9/C-10, or C-11 (Figure ). − Until now, only about 40 natural products have been categorized as nor -BPAP group, and almost all of them were derived from the common [3.3.1]-type-BPAPs, such as, norascyronone A, hyphenrone F, spirohypolactone B, and so on (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Hypaluton A, an Immunosuppressive 3,4-nor-Polycyclic Polyprenylated Acylphloroglucinol from Hypericum patulum

Duan

Xie

et al. 2021

J. Org. Chem.

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Hypaluton A (1), an unprecedented nor-polycyclic polyprenylated acylphloroglucinol (PPAP) bearing a new 8/6 bicyclic architecture, along with a new congener, hypaluton B (2), was obtained from Hypericum patulum. Their structures were confirmed by spectroscopic analyses, quantum-chemical 13C NMR calculations, electronic circular dichroism comparisons, and calculations. Hypaluton A is the first PPAP possessing an unparalleled 3,4-nor-bicyclic polyprenylated acylphloroglucinol (BPAP) scaffold, which might be derived from the common [5.3.1]-type-BPAP by losing seven carbons (C-3/4 of the acylphloroglucinol core and the isoprenyl at C-3) via the breakage at C-4–C-5 and C-2–C-3 bonds in the acylphloroglucinol core, together with the benzoyl migration through the hemiketalization/retro-Claisen cascade. More significantly, compound 1 is also the first discovered [6.3.0]-PPAP, which displayed pronounced inhibitory activity against lipopolysaccharide-induced B lymphocyte proliferation.

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Hyperfols A and B: Two Highly Modified Polycyclic Polyprenylated Acylphloroglucinols from Hypericum perforatum

Cited by 27 publications

References 19 publications

Hypermonones A—I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity

Hypermonones A—I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity

Three Unusual Sesquiterpenes with Distinctive Ring Skeletons from Daphne penicillata Uncovered by Molecular Networking Strategies

Hypaluton A, an Immunosuppressive 3,4-nor-Polycyclic Polyprenylated Acylphloroglucinol from Hypericum patulum

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