Sains Malaysiana 47(2)(2018):
319-322
http://dx.doi.org/10.17576/jsm-2018-4702-14
Chabrolene, a
Novel Norditerpene from the Bornean Soft Coral Nephthea sp.
(Chabrolene, Sebatian Novel Norditerpene daripada Karang Lembut Bornean Nephthea sp.)
Takahiro Ishii, Takashi
Kamada, Chin-Soon Phan & Charles S. Vairappan*
Institute
for Tropical Biology and Conservation, Universiti Malaysia Sabah
88400
Kota Kinabalu, Sabah, Malaysia
Received: 6 July 2017/Accepted: 7 September 2017
ABSTRACT
Soft corals are often the research interest
organism due to their structural diverse secondary metabolites with
wide spectrum of biological activities range from antibacterial
to anticancer potentials. The Borneo Island is rich in diversity
of marine organisms including soft coral. Therefore, a population
of Bornean soft coral belongs to genus Nephthea was collected from Mantanani Island (Sabah,
Malaysia) which led to the isolation of a novel norditerpene, chabrolene
(1) together with three known compounds (2-4). The chemical structure of 1 was determined by NMR and HREIMS data.
Compound 1 exhibited repellent activity against the
maize weevil Sitophilus zeamais.
Keywords: Nephthea sp.; norditerpene;
repellent activity; Sitophilus zeamais; soft coral
ABSTRAK
Karang lembut sering dikenali sebagai organisma yang penting
dalam penyelidikan disebabkan oleh metabolit sekunder yang pelbagai
struktur. Selain itu, ia juga mempunyai pelbagai aktiviti biologi terdiri daripada
potensi antibakteria hingga anti-kanser. Pulau Borneo kaya dengan
kepelbagaian organisma marin termasuk
karang lembut. Oleh itu, satu populasi karang lembut Bornean genus
Nephthea dikumpulkan dari Pulau
Mantanani (Sabah, Malaysia) dan mendapati satu norditerpene baru,
chabrolene (1) dan tiga sebatian yang
telah dikenal pasti (2-4). Struktur
kimia untuk keempat-empat sebatian ini dikenal pasti berdasarkan
analisis data spektroskopi NMR dan HREIMS. Sebatian 1 didapati mempunyai
aktiviti penolak terhadap kutu jagung Sitophilus zeamais.
Kata kunci: Aktiviti penolak; karang
lembut; Nephthea sp.; norditerpene; Sitophilus zeamais
REFERENCES
Amir, F., Koay, Y.C.
& Yam, W.S. 2012a. Chemical
constituents and biological properties of the marine soft coral Nephthea: A Review (Part 1). Tropical Journal of Pharmaceutical Research 11(3): 485-498.
Amir, F., Koay, Y.C.
& Yam, W.S. 2012b. Chemical
constituents and biological properties of the marine soft coral Nephthea: A Review (Part 2). Tropical Journal of Pharmaceutical Research 11(3): 499-517.
Blackman, A.J.,
Bowden, B.F., Coll, J.C., Frick, B., Mahendran, M. & Mitchell, S.J. 1982. Studies of Australian soft corals. XXIX several new cembranoid diterpenes from Nephthea brassica and related diterpenes
from a Sarcophyton species. Australian Journal of Chemistry 35(9):
1873-1880.
Bortolotto, M.,
Braekman, J.C., Daloze, D. & Tursch, B. 1977. Chemical studies of marine
invertebrates. XXIX. 4α-methyl-3β,8β-dihydroxy-5α-ergost-24(28)-en-23-one,
a novel polyoxygenated sterol
from the soft coral Litophyton viridis (Coelenterata, Octocorallia, Alcyonacea). Steroids 30(2): 159-164.
Chen, W.T., Li, Y. & Guo, Y.W. 2012. Terpenoids of Sinularia soft corals: Chemistry and bioactivity.
Acta Pharmaceutica Sinica B 2(3): 227-237.
Cheng, S.Y., Dai, C.F. & Duh, C.Y. 2007. New
4-methylated and 19-oxygenated steroids from the Formosan soft coral Nephthea erecta. Steroids 72(8): 653-659.
Cheng, S.Y., Huang, K.J., Wang, S.K., Wen, Z.H., Hsu, C.H., Dai, C.F. &
Duh, C.Y. 2009. New terpenoids from the soft corals
Sinularia capillosa and Nephthea chabroli. Organic Letters 11(21): 4830-4833.
Chu, S.S., Liu, Z.L., Du, S.S. & Deng, Z.W. 2012. Chemical composition
and insecticidal activity against Stiphilus
zeamais of the essential oils derived from Artemisia giraldii and Artemisia
subdigitata. Molecules 17(6):
7255-7265.
Handayani,
D., Edrada, R.A., Proksch, P., Wray, V., Witte, L., van Ofwegen, L. &
Kunzmann, A. 1997. New oxygenated sesquiterpenes from the
Indonesian soft coral Nephthea chabrolii. Journal of Natural Products 60(7):
716-718.
Hong,
T., Ma, Y., Sun, S. & Ma, C. 1992. Study on chemical
constituents of essential oil of Henan roasted tobacco. Journal of Instrumental Analysis 11: 64-65.
Hu, J.,
Yang, B., Lin, X., Zhou, X., Yang, X., Long, L. & Liu, Y. 2011.
Chemical and biological studies of soft corals of the Nephtheidae
family. Chemisty &
Biodiversity 8(6): 1011-1032.
Ishii, T., Matsuzawa, H. & Vairappan, C.S. 2010c. Repellent activity
of common spices against the rice weevil, Sitophilus
zeamais Motsch (Coleoptera, Curculionidae). Journal of Tropical Biology and Conservation 7: 75-80.
Ishii, T., Matsuura, H., Zhaoqi, Z. & Vairappan, C.S. 2009a. A
new 4α-methylated sterol from a Nephthea sp. (Nephtheidae) Bornean soft coral. Molecules 14(9): 3360-3366.
Ishii, T., Matsuura, H., Zhaoqi, Z. & Vairappan, C.S. 2009b. A
new norsesquiterpenoid from a Bornean soft coral genus Nephthea. Molecules 14(11): 4591-4596.
Ishii, T., Ueoka, R., Matsunaga, S. & Vairappan, C.S. 2010a. Bioactive
secondary metabolites from the Borneon soft corals of the genus
Nephthea. Malaysian Journal of Science 29(3): 262-268.
Ishii, T., Zhaoqi, Z. & Vairappan, C.S. 2010b. A new cembrane
diterpene from the Bornean soft coral Nephthea sp. Molecules 15(6): 3857-3862.
Januar,
H.I., Chasanah, E., Motti, C.A., Tapiolas, D.M., Liptrot, C.H. &
Wright, A.D. 2010. Cytotoxic cembranes from
Indonesian specimens of the soft coral Nephthea
sp. Marine Drugs 8(7): 2142-2152.
Kamada,
T., Phan, C.S., Tin, H.S., Vairappan, C.S. & Muhammad, T.S.T. 2016.
16-Hydroxycembra-1,3,7,11-tetraene, a new cembrane
diterpene from Malaysian soft coral genus Sarcophyton. Natural Product Communications 11(8):
1077-1078.
Lai,
D., Geng, Z., Deng, Z., van Ofwegen, L., Proksch, P. & Lin, W. 2013. Cembranoids from the soft coral Sinularia
rigida with antifouling activities. Journal of Agricultural and Food Chemistry 61(19): 4585-4592.
Moreira, M.D., Picanço, M.C., Barbosa, L.C.A., Guedes, R.N.C., Campos,
M.R., Silva, G.A. & Martins, J.C. 2007. Plant compounds
insecticide activity against Coleoptera pests of stored products. Pesquisa Agropecuária Brasileira 42(7):
909-915.
Núñez-Pons, L., Carbone, M., Vázquez, J., Gavagnin, M. & Avila, C.
2013. Lipophilic defenses from Alcyonium soft corals of Antarctica. Journal of Chemical Ecology 39(5): 675-685.
Schmitz,
F.J., Vanderah, D.J. & Ciereszko, L.S. 1974. Marine natural products: Nephthenol
and epoxynephthenol acetate, cembrene derivatives from a soft coral. Journal of the Chemical Society, Chemical
Communication 1974(10): 407-408.
Tello, E., Castellanos, L., Arevalo-Ferro, C. & Duque, C. 2009. Cembranoid
diterpenes from the Caribbean Sea whip Eunicea
knighti. Journal of Natural Products 72(9): 1595-1602.
Wang, S.K., Puu, S.Y. & Duh, C.Y. 2013. New steroids from the soft coral Nephthea chabrolii. Marine
Drugs 11(2): 571-580.
Zhang, J., Li, L.C., Wang, K.L., Liao, X.J., Deng, Z. & Xu, S.H. 2013. Pentacyclic hemiacetal sterol with antifouling and cytotoxic activities
from the soft coral Nephthea
sp. Bioorganic & Medicinal Chemistry Letters
23(4): 1079-1082.
Zhang,
W.H., Williams, I.D. & Che, C.T. 2001. Chabrolols A, B
and C, three new norditerpenes from the soft coral Nephthea chabroli. Tetrahedron
Letters 42(28): 4681-4685.
Zhao,
M., Yin, J., Jiang, W., Ma, M., Lei, X., Xiang, Z., Dong, J., Huang,
K. & Yan, P. 2013. Cytotoxic and antibacterial cembranoids from
a South China Sea soft coral, Lobophytum
sp. Marine Drugs 11(4): 1162-1172.
*Corresponding
author; email: csv@ums.edu.my
|