Okinawan Subtropical Plants as a Promising Resource for Novel Chemical Treasury

Matsunami, Katsuyoshi; Otsuka, Hideaki

doi:10.1248/cpb.c17-00831

Cited by 5 publications

(5 citation statements)

References 34 publications

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“…In particular, the glandular trichome of M. tanarius contains the highest level of total prenylflavonoids in the plant (Kumazawa et al . 2014, Matsunami & Otsuka 2018). The main prenylflavonoids that have been isolated from Okinawan propolis include nymphaeol B (NB; propolin D), isonymphaeol B (INB; propolin F), nymphaeol A (NA; propolin C), 3'‐geranyl‐naringenin (GN, propolin H) and nymphaeol C (NC; propolin G) (Kumazawa et al .…”

Section: Introductionmentioning

confidence: 98%

Prenylflavonoids isolated from Macaranga tanarius stimulate odontoblast differentiation of human dental pulp stem cells and tooth root formation via the mitogen‐activated protein kinase and protein kinase B pathways

et al. 2021

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Aim To identify odontogenesis‐promoting compounds and examine the molecular mechanism underlying enhanced odontoblast differentiation and tooth formation. Methodology Five different nymphaeols, nymphaeol B (NB), isonymphaeol B (INB), nymphaeol A (NA), 3’‐geranyl‐naringenin (GN) and nymphaeol C (NC) were isolated from the fruit of Macaranga tanarius. The cytotoxic effect of nymphaeols on human DPSCs was observed using a 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) assay. The effect of nymphaeols on odontoblast differentiation was analysed with Alizarin Red S staining and odontoblast marker expression was assessed using real‐time polymerase chain reaction and Western blot analysis. The molecular mechanism was investigated with Western blot analysis. In order to examine the effect of INB on dentine formation in the developing tooth germ, INB‐soaked beads were placed under the tooth bud explants in the collagen gel; thereafter, the tooth bud explant‐bead complexes were implanted into the sub‐renal capsules for 3 weeks. Tooth root formation was analysed using micro‐computed tomography and histological analysis. Data are presented as mean ± standard error (SEM) values of three independent experiments, and results are compared using a two‐tailed Student's t‐test. The data were considered to have statistical significance when the P‐value was less than 0.05. Results Three of the compounds, NB, INB, and GN, did not exert a cytotoxic effect on human DPSCs. However, INB was most effective in promoting the deposition of calcium minerals in vitro (P < 0.001) and induced the expression of odontogenic marker genes (P < 0.05). Moreover, this compound strongly induced the phosphorylation of mitogen‐activated protein (MAP) kinases and protein kinase B (AKT) (P < 0.05). The inhibition of p38 MAP, c‐Jun N‐terminal kinase (JNK), and AKT substantially suppressed the INB‐induced odontoblast differentiation (P < 0.001). In addition, isonymphaeol B significantly induced the formation of dentine and elongation of the tooth root in vivo (P < 0.05). Conclusions Prenylflavonoids, including INB, exerted stimulatory effects on odontoblast differentiation and tooth root and dentine formation via the MAP kinase and AKT signalling pathways. These results suggest that nymphaeols could stimulate the repair processes for dentine defects or injuries.

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Section: Introductionmentioning

confidence: 98%

Prenylflavonoids isolated from Macaranga tanarius stimulate odontoblast differentiation of human dental pulp stem cells and tooth root formation via the mitogen‐activated protein kinase and protein kinase B pathways

et al. 2021

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“…Some stilbenes were identified from this species including mappain, methyl-mappain, schweinfurthins (E, F, G, L, M, N, and O), and vedelianin (Péresse et al 2017). Matsunami and Otsuka (2018) recently summarized the chemical compounds of this species, adding to the work of Magadula (2014). The bark contains tannin and many varieties of it.…”

Section: Phytochemistrymentioning

confidence: 99%

Macaranga tanarius (L.) Müll.Arg. Euphorbiaceae

Mustaqim¹

2020

Ethnobotany of Mountain Regions

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Local NamesIndonesia: binunga (Sangir in Sulawesi); dahan (Alf. Minahasa); hanuwa (Ambon and Seram); hinan, lama (Ambon); karahan, tutup, tutup ancur, waru laut (Javanese); kayu mata putih (Atinggola in Gorontalo); kemahang putih (Bengkalis in Riau); lapi (Kolaka Timur and Buton in Sulawesi); mara (Sundanese); madau (Lampung); mapu (Batak); mombeti (Sigi in Sulawesi); ndenu (East Luwu in Sulawesi); rebak (Manggarai in Flores); same (Lako Akediri in Halmahera); sapat (Serampas in Jambi); seribu guna (Pidie in Aceh); surok (Krui in Lampung); totop lakèk (Madura); tubi tahak (Tetun in West Timor); tutup (Kerinci in Central Sumatra); umera (Wungkolo in Wawonii, Southeast Sulawesi). Malaysia: inchong, jebat musang, kundoh, mahang puteh, tampu, tampu hitam, tampu puteh; daun bayangan (Murut, Sabah); mahang putih (Ulu, Sarawak).

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“…Okinawan subtropical plants are known to produce a variety of compounds which possess unique biological activities. 1) For example, isonymphaeol B (INB) and 3′-geranyl naringenin, isolated from Macaranga tanarius fruits, increased glucose uptake in muscle cells by activating the AMP-activated protein kinase (AMPK) pathway. 2) INB also has been reported to induce the formation of dentine and elongation of the tooth root in vivo.…”

Section: Introductionmentioning

confidence: 99%

“…1 H-(600 MHz) and13 C-(150 MHz) NMR Spectral Data for 11Me-pavetannin B5, 11Me-(+)-cinnamtannin B 1 , and 11Me-aesculitannin B in CD 3 OD…”

mentioning

confidence: 99%

Studies on the Catechin Constituents of Bark of <i>Cinnamomum sieboldii</i>

Hirose

Ozaki

Saito

et al. 2023

CHEMICAL & PHARMACEUTICAL BULLETIN

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Screening for bioactivity related to anti-infective, anti-methicillin-resistantStaphylococcus aureus (MRSA) and anti-viral activity, led us to identify active compounds from a methanol extract of Litsea japonica (Thub.) Juss. and the hot water extract of bark of Cinnamomum sieboldii Meisn (also known as Karaki or Okinawa cinnamon). The two main components in these extracts were identified as the catechin trimers ( )-cinnamtannin B 1 and pavetannin B5. Moreover, these extracts exhibited anti-severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) activity. The structures of these catechin trimers were previously determined by chemical and spectroscopic methods. Pavetanin B5 has never been reported to be isolated as a pure form and has been obtained as a mixture with another component. Although other groups have reported the putative structure of pavetannin B5, preparation of the methylated derivative of pavetannin B5 in this study allowed us to obtain the pure form for the first time as the undecamethyl derivative and confirm its exact structure. Commercially available ( )-cinnamtannin B 1 and aesculitannin B (C2′-epimer of cinnamtannin B 1 ) both of which contained pavetannin B5 as a minor component, and C. sieboldii bark extract (approx. 5/2 mixture of ( )-cinnamtannin B 1 /pavetannin B5) were assessed for anti-SARS-CoV-2 activity. Both C. sieboldii bark extract and commercially available aesculitannin B showed viral growth inhibitory activity.

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Okinawan Subtropical Plants as a Promising Resource for Novel Chemical Treasury

Cited by 5 publications

References 34 publications

Prenylflavonoids isolated from Macaranga tanarius stimulate odontoblast differentiation of human dental pulp stem cells and tooth root formation via the mitogen‐activated protein kinase and protein kinase B pathways

Prenylflavonoids isolated from Macaranga tanarius stimulate odontoblast differentiation of human dental pulp stem cells and tooth root formation via the mitogen‐activated protein kinase and protein kinase B pathways

Macaranga tanarius (L.) Müll.Arg. Euphorbiaceae

Studies on the Catechin Constituents of Bark of <i>Cinnamomum sieboldii</i>

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