Tricalysiamides A−D, Diterpenoid Alkaloids from <i>Tricalysia dubia</i>

Nishimura, Koichi; Hitotsuyanagi, Yukio; Sugeta, Noriko; Fukaya, Haruhiko; Aoyagi, Yutaka; Hasuda, Tomoyo; Kinoshita, Takeshi; Takeya, Koichi

doi:10.1021/np0680681

Cited by 11 publications

(9 citation statements)

References 6 publications

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“…16-Demethoxydelavaine (218a and 218b) is a mixture of two regioisomers of lycoctonine-type alkaloids. 139 Four alkaloids in this group (222)(223)(224)(225) have alkoxy substituents at C-8. 135,142,143 Five new lycoctonine-type alkaloids 226-230 with an N-C-19-O-C-1 mixed acetal unit were isolated from the genera Consolida and Delphinium.…”

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confidence: 99%

“…10 Tricalysiamides. From the wood of Tricalysia dubia collected in Okinawa, Japan, four rearranged veatchine-type C 20 -diterpenoid alkaloids with a cafestol-type diterpene framework, tricalysiamides A-D(348)(349)(350)(351), were isolated recently 222. These novel compounds are designated, after the first example, as tricalysiamide-type diterpenoids, which are characterized by the nitrogen atom being between C-3 and C-19.…”

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confidence: 99%

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Diterpenoid alkaloids

2010

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The lasting attention that researchers have devoted to diterpenoid alkaloids is due to their various bioactivities and toxicities, structural complexity, and intriguing chemistry. From 1998 to the end of 2008, more than 300 new diterpenoid alkaloids were isolated from Nature. This review focuses on their structural relationships, and investigations into their chemical reactions, synthesis, and biological activities. A table that lists the names, plant sources, and structural types is given along with 363 references.

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Diterpenoid alkaloids

2010

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“…Ohwi (Rubiaceae) in 2007. 16 Cafemide A (1) was isolated as white amorphous powder, whose molecular formula was determined to be C 36 H 57 NO 4 at m/z 568.4369 [M + H] + (calcd for C 36 H 57 NO 4 + H + , 568.4360) in the HRESIMS. 1 H NMR spectrum showed the presence of one singlet methyl (δ H 0.90, s, H 3 -20), one triplet methyl (δ H 0.85, t, J = 7.0 Hz, H 3 -16′), one secondary amide (δ H 10.86, s, R−NH−CO−R′), and two olefinic methine (δ H 5.96, s, H-18 and δ H 5.47, m, H-2).…”

Section: Resultsmentioning

confidence: 99%

Lactam ent-Kaurane Diterpene: A New Class of Diterpenoids Present in Roasted Beans of Coffea arabica

Gao

Peng

et al. 2020

J. Agric. Food Chem.

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Seven new lactam ent-kaurane diterpenoids, cafemides A–G (1–7), were isolated from roasted beans of Coffea arabica. Their structures were elucidated by extensive spectroscopic analysis including 1D, 2D NMR (heteronuclear single quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC), 1H–1H correlation spectroscopy (COSY), and rotating frame Overhauser effect spectroscopy (ROESY)), high-resolution electrospray ionization mass spectrometry (HRESIMS), and IR spectra. They were divided into subtype I–III according to the structure. Further, with the aid of liquid chromatography–tandem mass spectrometry (LC–MS/MS) based molecular network, seven (8–14) subtype II diterpenoids were successfully identified. In addition, a variety of other subtypes of N-containing diterpenoids have been proven in roasted coffee. Compounds 1, 2, 3, 5, and 7 showed a moderate inhibitory effect on α-glucosidase with an IC50 value of 8.28 ± 0.62 μM, 38.23 ± 8.87 μM, 28.94 ± 1.42 μM, 12.44 ± 1.37 μM, and 22.2 ± 5.34 μM, respectively. To the best of our knowledge, this is the first time that N-containing diterpenoids have been reported in coffee.

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“…This plant species is used in traditional medicine as sedative and emetic, and for the treatment of malaria, jaundice, and skin diseases . Previous phytochemical studies of some plant species of the genus Tricalysia have reported the isolation of steroids, terpenoids, [ ] diterpenoid alkaloids, fatty acid esters, and glycosides . However, to the best of our knowledge, T .…”

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confidence: 99%

Tricalycoside, a New Cerebroside from Tricalysia coriacea (Rubiaceae)

Awouafack

Tane

Morita

2017

Chemistry & Biodiversity

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A new cerebroside, named as tricalycoside (1), was isolated from the CH 2 Cl 2 /MeOH (1:1) extract of twigs and leaves of Tricalysia coriacea using repeated silica gel open column chromatography followed by preparative TLC and Sephadex LH-20, together with six known compounds (2 -7). The structure of the new compound was determined by analysis of 1D-and 2D-NMR, MS data, chemical conversion, and by comparison of these data with those from the literature. Tricalycoside (1) possessed a weak antibacterial activity against Klebsiella pneumoniae (MIC = 75 lg/mL).

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Tricalysiamides A−D, Diterpenoid Alkaloids from Tricalysia dubia

Cited by 11 publications

References 6 publications

Diterpenoid alkaloids

Diterpenoid alkaloids

Lactam ent-Kaurane Diterpene: A New Class of Diterpenoids Present in Roasted Beans of Coffea arabica

Tricalycoside, a New Cerebroside from Tricalysia coriacea (Rubiaceae)

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