Antinociceptive grayanane-derived diterpenoids from flowers of Rhododendron molle

Li, Yong; Zhu, Yuxun; Zhang, Zhaoxin; Li, Li; Liu, Yun‐Bao; Qu, Jing; Ma, Shuang‐Gang; Yu, Shi‐Shan

doi:10.1016/j.apsb.2019.10.013

Cited by 26 publications

(20 citation statements)

References 18 publications

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“…Among them, birhodomolleins A—E were isolated from the flowers of R. molle collected at Jinxiu, Guangxi, China, and the fruits of R. pumilum at Aba, Sichuan, China, [ 9,27 ] respectively, by Ye's group. Rhodomollein XLIII [ 29 ] was isolated from the flowers of R. molle collected at Xing'an, Guangxi, China by Yu's group. While, bimollfoliagein A was isolated from the leaves of R. molle collected at Qichun, Hubei, China by our group.…”

Section: Resultsmentioning

confidence: 99%

“…[ 25 ] Dimeric grayanane diterpenoids are very rare, although over 300 grayanane diterpenoids have been reported. [ 25‐26 ] To date, only seven dimeric grayanane diterpenoids, birhodomolleins A—E, [ 9,27 ] bimollfoliagein A, [ 28 ] and rhodomollein XLIII, [ 29 ] were isolated. However, neither their relative configurations nor their absolute configurations were assigned by more solid evidences such as quantum chemical calculations and single‐crystal X‐ray diffraction.…”

Section: Background and Originality Contentmentioning

confidence: 99%

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Highly Oxygenated Dimeric Grayanane Diterpenoids as Analgesics: TRPV1 and TRPA1 Dual Antagonists from Rhododendron molle

et al. 2022

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Six highly oxygenated dimeric grayanane diterpenoids (1-6) including three new ones, bismollethers A-C (1-3), were isolated from the flowers of Rhododendron molle collected at Qichun, Hubei, China. The structures and relative configurations of 1-6 were determined by comprehensive spectroscopic data analysis and 13 C NMR calculation with DP4+ analysis. The absolute configurations of bismollethers A-C (1-3) and birhodomollein B (5) were indubitably assigned by single-crystal X-ray diffraction analysis, revealing the head-to-tail linking manner of diterpenoid monomers. Bismollether A (1) is a caged dimeric grayanane diterpenoid linked through two oxygen-bridges of C-2−O−C-14ʹ and C-14−O−C-2ʹ, featuring a unique 1,8-dioxacyclotetradecane motif. The plausible biosynthesis pathways of 1-6 are proposed. All the isolates displayed significant analgesic activities and their structure-activity relationships were discussed. Grayanane diterpenoid dimers were found to be TRPV1 and TRPA1 dual antagonists, and docking studies provide a structural basis to design potent analgesics.

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Section: Resultsmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

Highly Oxygenated Dimeric Grayanane Diterpenoids as Analgesics: TRPV1 and TRPA1 Dual Antagonists from Rhododendron molle

et al. 2022

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“…Kalmane diterpenoids featuring a 5/8/5/5 tetracyclic carbon skeleton are very rare in nature, and exclusively exist in the Ericaceae plants having a great renown for their beautiful flowers and structurally intriguing diterpenoids. [ 10‐11 ] Since the first kalmane diterpenoid, kalmanol, was isolated from Kalmia angustifolia (Ericaceae) in 1989, [ 12 ] heretofore, only eight kalmane diterpenoids, kalmanol, rhodomolleins XIV, XV, XXIII, XXIV, and XLII, 16 α ‐acetoxy rhodomollein XXIII and 8 α ‐ O ‐acetylrhodomollein XXIII, have been reported from K. angustifolia , [ 12 ] Rhododendron molle , [ 13‐16 ] and R. micranthum , [ 9,17 ] respectively.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Discovery of Kalmane Diterpenoids as Potent Analgesics from the Flowers of Rhododendron dauricum

et al. 2022

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Kalmane diterpenoids, featuring a 5/8/5/5 tetracyclic carbon skeleton, are very rare in nature. The flowers of Rhododendron dauricum L. (Ericaceae) were phytochemically investigated for the first time, leading to the isolation of eight kalmane diterpenoids (1-8) including four new ones, named rhodokalmanols A-D (1-4). The structures of 1-8 were elucidated by comprehensive spectroscopic methods and 13 C NMR-DP4+ analysis, and the absolute configurations of 1, 2, 4, and 5 were defined by single-crystal X-ray diffraction analysis with Cu Kα radiation. Rhodokalmanol A (1) represents the first 5,8-epoxykalmane diterpenoid and also the first kalm-15(16)-ene diterpenoid. Rhodokalmanols B-D (2-4) are the first examples of kalm-7(8)-ene, kalm-16( 17)-ene, and 8α-methoxykalmane diterpenoids, respectively. All the isolated kalmane diterpenoids 1-8 exhibited significant analgesic effects, and rhodokalmanol C (3) and kalmanol (8) expressed more potent analgesic activity than morphine at doses of 0.2 and 0.04 mg/kg. The preliminary structure-activity relationships of kalmane diterpenoids as potent analgesics are discussed.

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“…Many kinds of plants such as wheat , pea and maize have been sent into space and investigated in laboratories after returning to the ground. Among them, rice was the most common plant model used to study the relationship between physiological responses and the space environment.…”

Section: Introductionmentioning

confidence: 99%

Photosynthetic Performance of Rice Seedlings Originated from Seeds Exposed to Spaceflight Conditions

Cui

Xia

Wei

et al. 2019

Photochem & Photobiology

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The mechanism of the regulation on photosynthesis after spaceflight has not been fully understood. To learn more information about this, we conducted a series of experiments of photosystem, including photosynthetic physiological characteristics (fluorescence parameters, pigment contents), gene expression and proteomic change. We want to examine the response of rice (Oryza sativaDN416), whose seeds were placed in Bio‐Radiation Box on the ShiJian‐10(SJ‐10) recoverable satellite. Our results demonstrated that the photosynthesis capacity of plants after spaceflight declined, compared to ground control plants. Specifically, Fv/Fm is significantly reduced for 7.5%. Chlorophyll content decreased in the three growth stages of rice, trefoil, tillering and mature stages. To further analyze changes under spaceflight environment, quantitative real‐time PCR technology and isobaric tags for relative and absolute quantization (iTRAQ) labeling technology were deployed. We found that the gene expression of important subunits of key enzymes and important structures had been decreased after spaceflight. As for the results of changes in proteins, we discovered that the content of proteins related to electron transport and photosynthesis key enzyme declined. Our experiments can provide reference for further research to learn more about the effects of spaceflight on photosynthesis.

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Antinociceptive grayanane-derived diterpenoids from flowers of Rhododendron molle

Cited by 26 publications

References 18 publications

Highly Oxygenated Dimeric Grayanane Diterpenoids as Analgesics: TRPV1 and TRPA1 Dual Antagonists from Rhododendron molle

Highly Oxygenated Dimeric Grayanane Diterpenoids as Analgesics: TRPV1 and TRPA1 Dual Antagonists from Rhododendron molle

Discovery of Kalmane Diterpenoids as Potent Analgesics from the Flowers of Rhododendron dauricum

Photosynthetic Performance of Rice Seedlings Originated from Seeds Exposed to Spaceflight Conditions

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