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References (58)
-
Y. Xu, J.‐H. Lang, W.‐H. Jiao, R.‐P. Wang, Y. Peng, S.‐J. Song, B.‐H. Zhang, H.‐W. Lin (2012)
Formamido‐Diterpenes from the South China Sea Sponge Acanthella cavernosa, 10
-
G. Trimurtulu, D. J. Faulkner (1994)
Six New Diterpene Isonitriles from the Sponge Acanthella cavernosa, 57
-
N. Grimblat, M. M. Zanardi, A. M. Sarotti (2015)
Beyond DP4: an Improved Probability for the Stereochemical Assignment of Isomeric Compounds Using Quantum Chemical Calculations of NMR Shifts, 80
-
J. M. Wang, X. Y. Pang, C. M. Chen, C. H. Gao, X. F. Zhou, Y. H. Liu, X. W. Luo (2022)
Chemistry, Biosynthesis, and Biological Activity of Halogenated Compounds Produced by Marine Microorganisms, 40
-
M. Ambrogi, A. Ciogli, M. Mancinelli, S. Ranieri, A. Mazzanti (2013)
Atropisomers of Arylmaleimides: Stereodynamics and Absolute Configuration, 78
-
C. W. J. Chang, A. Patra, J. A. Baker, P. J. Scheuer (1987)
Kalihinols, Multifunctional Diterpenoid Antibiotics from Marine Sponges Acanthella spp, 109
-
Emsermann J. (2016)
16/1–16/83Mar. Drugs, 14
-
J. Emsermann, U. Kauhl, T. Opatz (2016)
Marine Isonitriles and Their Related Compounds, 14
-
Wang J. M. (2022)
1729Chin. J. Chem., 40
-
T. Okino, E. Yoshimura, H. Hirota, N. Fusetani (1996)
New Antifouling Kalihipyrans from the Marine Sponge Acanthella cavernosa, 59
-
S. Grimme, J. Antony, S. Ehrlich, H. Krieg (2010)
A Consistent and Accurate ab initio Parametrization of Density Functional Dispersion Correction (DFT‐D) for the 94 Elements H‐Pu, 132
-
A. Patra, C. W. J. Chang, P. J. Scheuer, G. D. Van Duyne, G. K. Matsumoto, J. Clardy (1984)
An Unprecedented Triisocyano Diterpenoid Antibiotic from a Sponge, 106
-
Ambrogi M. (2013)
3709J. Org. Chem., 78
-
L. H. Yang, O. O. Lee, T. Jin, X. C. Li, P. Y. Qian (2006)
Antifouling Properties of 10β‐formamidokalihinol‐A and Kalihinol A Isolated from the Marine Sponge Acanthella cavernosa, 22
-
P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. Mcmahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney, M. R. Boyd (1990)
New Colorimetric Cytotoxicity Assay for Anticancer‐Drug Screening, 82
-
Braekman J. C. (1994)
187Bull. Soc. Chim. Belg., 103
-
Skehan P. (1990)
1107J. Natl. Cancer Inst., 82
-
Xu Y. (2012)
2876Tetrahedron, 68
-
H. Miyaoka, M. Shimomura, H. Kimura, Y. Yamada (1998)
Antimalarial Activity of Kalihinol A and New Relative Diterpenoids from the Okinawan Sponge, 54
-
Wu Q. H. (2019)
56/1–56/12Mar. Drugs, 17
-
K. A. Alvi, L. Tenenbaum, P. Crews (1991)
Anthelmintic Polyfunctional Nitrogen‐Containing Terpenoids from Marine Sponges, 54
-
R. J. Clark, B. L. Stapleton, M. J. Garson (2000)
New Isocyano and Isothiocyanato Terpene Metabolites from the Tropical Marine Sponge Acanthella cavernosa, 56
-
Sun J.‐Z. (2009)
1581Arch. Pharm. Res., 32
-
M. J. Garson, J. S. Simpson (2004)
Marine Isocyanides and Related Natural Products – Structure, 21
-
Yang L. H. (2006)
23Biofouling, 22
-
Rodriguez J. (1994)
11079Tetrahedron, 50
-
Mosmann T. (1983)
55J. Immunol. Methods, 65
-
Trimurtulu G. (1994)
501J. Nat. Prod., 57
-
Clark R. J. (2000)
3071Tetrahedron, 56
-
Xu Y. (2012)
1445Mar. Drugs, 10
-
Grimblat N. (2015)
12526J. Org. Chem., 80
-
J. Rodriguez, R. M. Nieto, L. M. Hunter, M. C. Diaz, P. Crews, E. Lobkovsky, J. Clardy (1994)
Variation among Known Kalihinol and New Kalihinene Diterpenes from the Sponge Acanthella cavernosa, 50
-
Miyaoka H. (1998)
13467Acanthella sp. Tetrahedron, 54
-
S. Omar, C. Albert, T. Fanni, P. Crews (1988)
Polyfunctional Diterpene Isonitriles from Marine Sponge Acanthella carvenosa, 53
-
S. G. Smith, J. M. Goodman (2009)
Assigning the Stereochemistry of Pairs of Diastereoisomers Using GIAO NMR Shift Calculation, 74
-
Okino T. (1996)
1081J. Nat. Prod., 59
-
Grimme S. (2010)
154104J. Chem. Phys., 132
-
T. Okino, E. Yoshimura, H. Hirota, N. Fusetani (1995)
Antifouling Kalihinenes from the Marine Sponge Acanthella cavernosa, 36
-
Chang C. W. J. (1984)
4644J. Am. Chem. Soc., 106
-
Shen S.‐M. (2022)
235Chin. J. Chem., 40
-
J.‐Z. Sun, K.‐S. Chen, L.‐G. Yao, H.‐L. Liu, Y.‐W. Guo (2009)
A New Kalihinol Diterpene from the Hainan Sponge Acanthella sp, 32
-
Y. Xu, N. Li, W.‐H. Jiao, R.‐P. Wang, Y. Peng, S.‐H. Qi, S.‐J. Song, W.‐S. Chen, H.‐W. Lin (2012)
Antifouling and Cytotoxic Constituents from the South China Sea Sponge Acanthella cavernosa, 68
-
S.‐M. Shen, Z.‐Y. Zhang, L.‐G. Yao, J.‐R. Wang, Y.‐W. Guo, X.‐W. Li (2022)
Nitrogenous Sesquiterpenoids from the South China Sea Nudibranch Hexabranchus sanguineus and Its Possible Sponge‐Prey Acanthella cavernosa: Chiral Separation, Stereochemistry and Chemical Ecology, 40
-
Alvi K. A. (1991)
71J. Nat. Prod., 54
-
Garson M. J. (2004)
164Biosynthesis and Ecology. Nat. Prod. Rep., 21
-
Smith S. G. (2009)
4597J. Org. Chem., 74
-
T. Mosmann (1983)
Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays, 65
-
Becke A. D. (1993)
1372J. Chem. Phys., 98
-
Patra A. (1984)
7981J. Am. Chem. Soc., 106
-
Chang C. W. J. (1987)
6119J. Am. Chem. Soc., 109
-
C. W. J. Chang, A. Patra, D. M. Roll, P. J. Scheuer, G. K. Matsumoto, J. Clardy (1984)
Kalihinol‐A, a Highly Functionalized Diisocyano Diterpenoid Antibiotic from a Sponge, 106
-
Omar S. (1988)
5971J. Org. Chem., 53
-
Q. H. Wu, W.‐T. Chen, S.‐W. Li, J.‐Y. Ye, X.‐J. Huan, M. Gavagnin, L.‐G. Yao, H. Wang, Z.‐H. Miao, X.‐W. Li, Y.‐W. Guo (2019)
Cytotoxic Nitrogenous Terpenoids from Two South China Sea Nudibranchs Phyllidiella pustulosa, Phyllidia coelestis, and Their Sponge‐Prey Acanthella cavernosa, 17
-
N. Fusetani, K. Yasumuro, H. Kawai, T. Natori, L. Brinen, J. Clardy (1990)
Kalihinene and Isokalihinol B, Cytotoxic Diterpene Isonitriles from the Marine Sponge Acanthella klethra, 31
-
A. D. Becke (1993)
A New Mixing of Hartree‐Fock and Local‐Density‐Functional Theories, 98
-
Fusetani N. (1990)
3599Tetrahedron Lett., 31
-
Okino T. (1995)
8637Tetrahedron Lett., 36
-
J. C. Braekman, D. Daloze, F. Gregoire, S. Popov, R. Van Soest (1994)
Two New Kalihinenes from the Marine Sponge Acanthella cavernosa, 103
- Publisher
- Wiley
- Copyright
- © 2022 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH
- eISSN
- 1614-7065
- DOI
- 10.1002/cjoc.202200120
- Publisher site
- See Article on Publisher Site
Abstract
Seven new kalihinene diterpenoids, kalihioxepanes A—G (1—7) bearing a rare oxepane ring, were isolated from sponge Acanthella cavernosa collected from the South China Sea. The structures and absolute configurations were elucidated by comprehensive spectroscopic analysis, single crystal X‐ray diffraction, and quantum chemical calculation methods. Kalihioxepane A (1) displayed strong cytotoxicity against H69 and K562 tumor cells, while kalihioxepane B (2) showed moderate cytotoxicity against K562 cells.
Journal
Chinese Journal of Chemistry – Wiley
Published: Aug 1, 2022
Keywords: Acanthella cavernosa; Kalihinenes; Configuration determination; Cytotoxicity; Natural products