Anti-Hepatitis B Virus and Cytotoxic Diterpenoids from Isodon lophanthoides var. gerardianus

Yang, Ling; Li, Lin; Huang, Sheng‐Xiong; Pu, Jian‐Xin; Zhao, Yong; Ma, Yun‐Bao; Chen, Ji‐Jun; Leng, Chun-hong; Tao, Zheng-Ming; Sun, Han‐Dong

doi:10.1248/cpb.59.1102

Cited by 32 publications

(21 citation statements)

References 17 publications

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“…In this study, twenty-two compounds were isolated from the roots of C. megalocarpoides including twelve new ent-clerodane diterpenoids (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12), a new abietane diterpenoid (13), the known crotocorylifuran (4 a) [7] (l " Fig. 1), the two known abietane diterpenoids, isolophanthin A [8] and abietic acid [9], four known ent-trachylobane diterpenoids, ent-3α,18-dihydroxytrachylobane [10], ent-trachyloban-18-ol [10], ent-trachyloban-18-oic acid [10,11], ent-3α-hydroxytrachyloban-18-al [12] and the triterpenoids, lupeol [13] and acetyl aleurotolic acid [14,15]. Compound 1 was isolated as a colourless oil and was determined to have a molecular formula of C 21 H 28 O 5 from HR-ESI-MS.…”

Section: Resultsmentioning

confidence: 99%

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New ent-Clerodane and Abietane Diterpenoids from the Roots of Kenyan Croton megalocarpoides Friis & M. G. Gilbert

et al. 2016

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The roots of the endangered medicinal plant Croton megalocarpoides collected in Kenya were investigated and twenty-two compounds isolated. Among them were twelve new ent-clerodane (1-12) and a new abietane (13) diterpenoids, alongside the known crotocorylifuran (4 a), two known abietane and four known ent-trachylobane diterpenoids, and the triterpenoids, lupeol and acetyl aleurotolic acid. The structures of the compounds were determined using NMR, HRMS and ECD. The isolated compounds were evaluated against a series of microorganisms (fungal and bacteria) and also against Plasmodium falciparum, however no activity was observed.

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Section: Resultsmentioning

confidence: 99%

“…H NMR chemical shifts for compound(7)(8)(9)(10)(11)(12)(13) isolated from C. megalocarpoides.5.78 br d W 1/2 = 11.4 -5.75 br d, W 1/2 = 11.4 -5.77 br d, W 1/2 = 11.0 -5.65 br d W 1/2 = 13.6 -Ndunda B et al New ent-Clerodane and … Planta Med…”

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New ent-Clerodane and Abietane Diterpenoids from the Roots of Kenyan Croton megalocarpoides Friis & M. G. Gilbert

et al. 2016

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“…gerardianus and I. lophanthoides var. micranthus [6, 8–10, 19], none of them showed identical molecular weight and possible fragmentation pathways to the peaks in this study. However, the calculated formulae and MS/MS fragments –C 3 H 4 (−40 Da), –C 3 H 6 (−42 Da) and –C 5 H 8 (−68 Da) (removal of side chain from C ring) indicated that most of the peaks could be attributed to abietane-type diterpenoids.…”

Section: Resultsmentioning

confidence: 69%

Rapid differentiation of Xihuangcao from the three Isodon species by UPLC-ESI-QTOF-MS/MS and chemometrics analysis

et al. 2016

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Background Isodon lophanthoides, I. lophanthoides var. graciliflorus and I. serra are the three botanical sources of Xihuangcao, which are often used indiscriminately in herbal products. The aim of this study was to develop a rapid and accurate analytical method to identify the three different botanical sources of Xihuangcao by combining UPLC-ESI-QTOF-MS with chemometrics analysis.MethodsFifteen batches of plants were collected as reference materials and their chemical profiles were analyzed by UPLC-ESI-QTOF-MS. These data were subsequently processed by statistical methods, including principal component analysis (PCA), hierarchical cluster analysis (HCA) and orthogonal partial least squared discriminant analysis (OPLS-DA). An automated sample class prediction model was also built using Naive Bayes as a class prediction algorithm to rapidly determine the source species of twenty-seven batches of commercial Xihuangcao samples.ResultsThe base peak chromatograms of the three authenticated species showed different patterns and twenty-seven peaks were chosen, including six diterpenoids, one phenolic acid and two glycosides to distinguish among these three species. The results showed good differentiation among the three species by PCA, HCA and OPLS-DA. Isodon lophanthoides var. graciliflorus was found to be the major botanical source of the commercial samples.ConclusionUPLC-ESI-QTOF-MS and subsequent chemometrics analysis were demonstrated effective to differentiate among the three different species of plants used as Xihuangcao.Electronic supplementary materialThe online version of this article (doi:10.1186/s13020-016-0120-y) contains supplementary material, which is available to authorized users.

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“…A search for NMR data provided partial assignment of the 1 H signals of 4 to 6, 20 while total 13 C NMR data assignment for 3, 22 4, and 6 21 was available. However, data of C-5, C-7, C-8, and the acetoxy carbonyl at C-7 assigned 21 13 C NMR data are wrongly assigned. The discrepancies between the reported and our values made as mandatory to confirm the absolute configuration (AC) of 3 to 6 using vibrational circular dichroism (VCD) spectroscopy.…”

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“…Royleanones 1 to 3 and 7 have been isolated from different genera of the Lamiaceae family, [4][5][6] while 2 has also been described from species of the Taxodiaceae family. 7,8 Some of these compounds exhibit antibacterial, [9][10][11] cytotoxic, 12 antiviral, 13 gastroprotective, 14 and antiparasitic 15,16 activities.…”

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Configurational Study of Diastereoisomeric Royleanone Diterpenoids FromSalvia concolor

Díaz-Fernández

Salazar

Joseph‐Nathan

et al. 2019

Natural Product Communications

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The known diterpenoids horminone (1) and taxoquinone (2) as a mixture, and pure 6,7-dehydroroyleanone (7) were isolated from the aerial parts of not yet studied Salvia concolor Lamb. Although 1 and 2 are known, the 1H Nuclear Magnetic Resonance (NMR) data of their acetyl derivatives 4 to 6 are only partially described. Moreover, the 13C NMR data assignments for 4 and 6 show some inconsistencies and reveal better agreement with those we obtained for diastereoisomeric 3 and 5. Since stereochemical aspects were in doubt, it was considered as mandatory to unambiguously determine the absolute configuration of 3 to 6 using vibrational circular dichroism spectroscopy, which then allowed the complete 1H and 13C NMR chemical shift assignments of 4 to 6.

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Anti-Hepatitis B Virus and Cytotoxic Diterpenoids from Isodon lophanthoides var. gerardianus

Cited by 32 publications

References 17 publications

New ent-Clerodane and Abietane Diterpenoids from the Roots of Kenyan Croton megalocarpoides Friis & M. G. Gilbert

New ent-Clerodane and Abietane Diterpenoids from the Roots of Kenyan Croton megalocarpoides Friis & M. G. Gilbert

Rapid differentiation of Xihuangcao from the three Isodon species by UPLC-ESI-QTOF-MS/MS and chemometrics analysis

Configurational Study of Diastereoisomeric Royleanone Diterpenoids FromSalvia concolor

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