Top

Published in:

01-01-2019 | Original Paper

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

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

Published in: Journal of Natural Medicines | Issue 1/2019

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.

Available only for authorised users

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

Title: Caryopincaolide M, a rearranged abietane diterpenoid with new skeleton and a new iridoid from Caryopteris incana
Authors: Cheng-Gang Zhang
Ting Chen
Xu-Dong Mao
Sen-Miao Zhao
Gui-Xin Chou
Publication date: 01-01-2019
Publisher: Springer Singapore
Published in: Journal of Natural Medicines / Issue 1/2019
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-018-1268-9

At a glance: The STEP trials

Springer Medicine

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

Abstract

At a glance: The STEP trials

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 1/2019

Two new xanthones and cytotoxicity from the bark of Garcinia schomburgkiana

Structure of constituents isolated from the bark of Cassipourea malosana and their cytotoxicity against a human ovarian cell line

Betulinic acid attenuates liver fibrosis by inducing autophagy via the mitogen-activated protein kinase/extracellular signal-regulated kinase pathway

Cycloartane triterpenoid (23R, 24E)-23-acetoxymangiferonic acid inhibited proliferation and migration in B16-F10 melanoma via MITF downregulation caused by inhibition of both β-catenin and c-Raf–MEK1–ERK signaling axis

Polydatin protects against acute myocardial infarction-induced cardiac damage by activation of Nrf2/HO-1 signaling

Identification of β-carboline and canthinone alkaloids as anti-inflammatory agents but with different inhibitory profile on the expression of iNOS and COX-2 in lipopolysaccharide-activated RAW 264.7 macrophages