nach oben

Journal of Natural Medicines

Erschienen in:

01.01.2019 | Original Paper

Caryopincaolide M, a rearranged abietane diterpenoid with new skeleton and a new iridoid from Caryopteris incana

verfasst von: Cheng-Gang Zhang, Ting Chen, Xu-Dong Mao, Sen-Miao Zhao, Gui-Xin Chou

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2019

Einloggen, um Zugang zu erhalten

Abstract

Caryopincaolide M (1), a new rearranged abietane diterpenoid with an unusual pent-4-enoic acid group on a 6/6/5 tricyclic ring system, and 7-epi-8-dehydroxypatriscabrol (3), a new iridoid, together with 17 known compounds, have been isolated from the whole plant of Caryopteris incana (Thunb.) Miq. Their structures were elucidated on the basis of 1-D and 2-D NMR, IR, and mass spectroscopic data. Compounds 1–5 were evaluated for their inhibitory activities against enzyme α-glucosidase, and the results showed that only 1 has moderate inhibitory activity against enzyme α-glucosidase with IC₅₀ at 528.3 ± 12.37 mg/L.

Nur mit Berechtigung zugänglich

Zhao SM, Chou GX, Yang QS, Wang W, Zhou JL (2016) Abietane diterpenoids from Caryopteris incana (Thunb.) Miq. Org Biomol Chem 14:3510–3520CrossRef

Luo G, Ye Q, Du B, Wang F, Zhang GL, Luo Y (2016) Iridoid glucosides and diterpenoids from Caryopteris glutinosa. J Nat Prod 79:886–893CrossRef

Saruul E, Murata T, Selenge E, Sasaki K, Yoshizaki F, Batkhuu J (2015) An antibacterial ortho-quinone diterpenoid and its derivatives from Caryopteris mongolica. Bioorg Med Chem Lett 25:2555–2558CrossRef

Murata T, Ishikawa Y, Saruul E, Selenge E, Sasaki K, Umehara K, Batkhuu J (2016) Abietane-type diterpenoids from the roots of Caryopteris mongolica and their cholinesterase inhibitory activities. Phytochemistry 130:152–158CrossRef

Zhang YH, Wang YL, Wei QY, Cai YJ, Wang Q, Liu ZL (2005) Diterpenoids from the Chinese herb Caryopteris terniflora and their antibacterial and antitumor activity. Pharmazie 60:551–553PubMed

Yu DJ, Wu ZY, Cui HB (1982) Flora of China, vol 65. Science Press, Beijing, p 198

Xu C, Chou GX, Wang CH, Wang ZT (2012) Rare noriridoids from the roots of Andrographis paniculata. Phytochemistry 77:275–279CrossRef

Zheng W, Tan XQ, Guo LJ, Kong FF, Lu P, Ni DJ, Wang P (2012) Chemical constituents from Monochasma savatieri. Chin J Nat Med 10:102–104CrossRef

Cocker W, Crowley KJ, Srinivasan K (1972) The chemistry of terpenes. Part XV. Some oxygenated derivatives of p-menthane. J Chem Soc 1972:1971–1980

10.

Matsunami K, Otsuka H, Takeda Y (2011) Myrseguinosides A–E, five new glycosides from the fruits of Myrsine seguinii. Chem Pharm Bull 59:1274–1280CrossRef

11.

Mahmoud AA, Ahmed AA (2006) α-Pinene-type monoterpenes and other constituents from Artemisia suksdorfii. Phytochemistry 67:2103–2109CrossRef

12.

Miyazawa M, Miyamoto Y (2004) Biotransformation of (+)-(1R, 2S)-fenchol by the larvae of common cutworm (Spodoptera litura). Tetrahedron 60:3091–3096CrossRef

13.

Kuo YH, Chen WC, Lee CK (2000) Four new terpenes from the percarp of Platycladus orientalis. Chem Pharm Bull 48:766–768CrossRef

14.

Heymann H, Tezuka Y, Kikuchi T, Supriyatna S (1994) Constituents of Sindora sumatrana MIQ. I. Isolation and NMR spectral analysis of sesquiterpenes from the dried pods. Chem Pharm Bull 42:138–146CrossRef

15.

Tsui WY, Brown GD (1996) Sesquiterpenes from Baeckea frutescens. J Nat Prod 59:1084–1086CrossRef

16.

Kitajima J, Suzuki N, Satoh M, Watanabe M (2002) Sesquiterpenoids of Torilis japonica fruit. Phytochemistry 59:811–815CrossRef

17.

Macías FA, Lacret R, Varela RM, Nogueiras C, Molinillo JM (2008) Bioactive apocarotenoids from Tectona grandis. Phytochemistry 69:2708–2715CrossRef

18.

Li HB, Yu Y, Wang ZZ, Xiao W, Yao XS (2014) Research on antiviral constituents in Re-Du-Ning injection. China Tradit Herb Drugs 12:1682–1687

19.

Wang DD, Liu SQ, Chen YJ, Wu LJ, Sun JY, Zhu TR (1982) Study on the active constituents of Syringa oblata. Acta Pharm Sinica 12:11

20.

Ma CY, Musoke SF, Tan GT, Sydara K, Bouamanivong S, Southavong B, Soejarto DD, Fong HHS, Zhang HJ (2008) Study of antimalarial activity of chemical constituents from Diospyros quaesita. Chem Biodivers 11:2442–2448CrossRef

21.

Wang RP, Lin HW, Li LZ, Gao PY, Xu Y, Song SJ (2012) Monoindole alkaloids from a marine sponge Mycale fibrexilis. Biochem Syst Ecol 43:210–213CrossRef

22.

Nakamura Y, Miyatake R, Inomata S, Ueda M (2008) Synthesis and bioactivity of potassium β-d-glucopyranosyl 12-hydroxy jasmonate and related compounds. Biosci Biotech Bioch 72:2867–2876CrossRef

23.

Chen T, Kan YJ, Chou GX, Zhang CG. (2017) A new highly oxygenated pregnane and two new 5-hydroxymethylfurfural derivatives from the water decoction of Poria cocos. J Asian Nat Prod Res 1–7

Titel: Caryopincaolide M, a rearranged abietane diterpenoid with new skeleton and a new iridoid from Caryopteris incana
verfasst von: Cheng-Gang Zhang
Ting Chen
Xu-Dong Mao
Sen-Miao Zhao
Gui-Xin Chou
Publikationsdatum: 01.01.2019
Verlag: Springer Singapore
Erschienen in: Journal of Natural Medicines / Ausgabe 1/2019
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-018-1268-9

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Weitere Artikel der Ausgabe 1/2019

Preventive agents for neurodegenerative diseases from resin of Dracaena cochinchinensis attenuate LPS-induced microglia over-activation

The analgesic effect and possible mechanisms by which koumine alters type II collagen-induced arthritis in rats

Two new oleanane derivatives from the fruits of Leonurus japonicus and their cytotoxic activities

Comprehensive evaluation of antioxidant effects of Japanese Kampo medicines led to identification of Tsudosan formulation as a potent antioxidant agent

A review of the ethnopharmacology, phytochemistry, and pharmacology of Changium smyrnioides Wolff

Seven new resin glycosides from the seeds of Quamoclit × multifida