Diterpenoids from the fruits of Rhododendron molle , potent analgesics for acute pain

Li, Yong; Zhu, Yuxun; Zhang, Zhao-Xin; Liu, Yang-Lan; Liu, Yun‐Bao; Qu, Jing; Ma, Shuang‐Gang; Wang, Xiaojing; Yu, Shi‐Shan

doi:10.1016/j.tet.2017.12.017

Cited by 24 publications

(9 citation statements)

References 12 publications

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“…Kalmane diterpenoids possessing a unique 5/8/5/5 tetracyclic diterpene carbon skeleton are very rare in nature. Up to date, only eight kalmane diterpenoids, kalmanol, [ 12 ] rhodomolleins XIV, XV, XXIII, XXIV, and XLII, [ 13‐16 ] 16 α ‐acetoxy rhodomollein XXIII and 8 α ‐ O ‐acetylrhodomollein XXIII, [ 9,17 ] have been reported from K. angustifolia , Rhododendron molle , and R. micranthum , respectively. It is the first time to report the presence of kalmane diterpenoids in the flowers of R. dauricum .…”

Section: Resultsmentioning

confidence: 99%

“…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%

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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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Section: Resultsmentioning

confidence: 99%

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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“…The grayananes are the major type of Ericaceae diterpenoids, while epoxygenated grayanane diterpenoids are relatively rare. To date, approximately 55 epoxygrayanane diterpenoids have been reported, including 28 2,3-epoxygrayananes, ,, a 2,3:11,16-diepoxygrayanane, 11 5,9-epoxygrayananes, ,,, five 6,10-epoxygrayananes, ,, a 9,10-epoxygrayanane, a 1,7-epoxygrayanane, a 2,10-epoxygrayanane, a 15,16-epoxygrayanane, an 11,16-epoxygrayanane, and five 10,14-epoxygrayananes . However, there is no report of 5,20-epoxygrayanane diterpenoids.…”

Section: Resultsmentioning

confidence: 99%

“…To date, only two 3α-oxygrayanane diterpenoids, pierisformosid E from Pieris formosa and 3- epi -grayanoside B from Rhododendron micranthum , have been reported. Auriculatol B ( 2 ) and 3- epi -grayanotoxin XVIII ( 3 ) are the third and fourth 3α-oxygrayanane diterpenoids.…”

Section: Resultsmentioning

confidence: 99%

Grayanane Diterpenoids from the Leaves of Rhododendron auriculatum and Their Analgesic Activities

Sun

Zheng

et al. 2019

J. Nat. Prod.

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Twenty-four grayanane diterpenoids (1–24) including 12 new ones (1–12) were isolated from Rhododendron auriculatum. The structures of the new grayanane diterpenoids (1–12) were defined via extensive spectroscopic data analysis. The absolute configurations of compounds 2–4, 10–12, 14, and 16 were established by single-crystal X-ray diffraction analysis, and electronic circular dichroism data were used to define the absolute configurations of auriculatols D (8) and E (9). Auriculatol A (1) is the first example of a 5,20-epoxygrayanane diterpenoid bearing a 7-oxabicyclo[4.2.1]nonane motif and a trans/cis/cis/cis-fused 5/5/7/6/5 pentacyclic ring system. Auriculatol B (2) is the first example of a 3α,5α-dihydroxy-1-βH-grayanane diterpenoid. 19-Hydroxy-3-epi-auriculatol B (6) and auriculatol C (7) represent the first examples of 19-hydroxygrayanane and grayan-5(6)-ene diterpenoids, respectively. Diterpenoids 1–24 showed analgesic activities in the writhing test induced by HOAc, and 2, 6, 10, 13, 19, and 24 at a dose of 5.0 mg/kg exhibited significant analgesic effects (inhibition rates >50%). Grayanane diterpenoids grayanotoxins I (19) and IV (24) at doses of 0.2 and 0.04 mg/kg showed more potent analgesic activities than morphine.

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“…A gathering of the fruits of this plant from Guangxi Province, China, led to the discovery of three new chlorinated diterpenoids rhodomollein XXXI -XXXIII (163 -165) in a group of 12 new compounds isolated in this study (Figure 33). 79 All three metabolites show significant antinociceptive activity, especially 164 and 165 at a very low dose (2 mg/kg). In contrast to chlorinated terpenoids (vide supra), chlorinated plant alkaloids are exceedingly rare.…”

Section: Figure 31 Structures Of New Chlorinated Phenolic Glycosides From Terrestrial Plantsmentioning

confidence: 95%

Newly discovered naturally occurring organohalogens

Gribble¹

2018

Arkivoc

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Last year more than 200 naturally occurring organohalogens were described for the first time. These natural products were isolated and characterized from marine algae, sponges, corals, tunicates, bryozoans, marine and terrestrial fungi and bacteria, cyanobacteria, terrestrial plants, slime molds, red ants, and interstellar space. The following examples are illustrative of the extraordinary synthetic virtuosity of nature.

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Diterpenoids from the fruits of Rhododendron molle , potent analgesics for acute pain

Cited by 24 publications

References 12 publications

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

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

Grayanane Diterpenoids from the Leaves of Rhododendron auriculatum and Their Analgesic Activities

Newly discovered naturally occurring organohalogens

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