A New Dinorspongian Diterpene with Pyridyl D-Ring from the Marine Sponge Spongia sp.

doi:10.6023/cjoc202109024

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (3): 901-904.DOI: 10.6023/cjoc202109024 Previous Articles Next Articles

NOTES

海绵Spongia sp.中一个新的D环为吡啶环的降海绵烷型二萜

梁咏倩^a^,^b, 廖小建^a, 凌珑^a, 杨雅婷^a, 赵冰心^a^,^*(), 徐石海^a^,^*()

a 暨南大学化学与材料学院广州 510632
b 广东药科大学药学院广州 510006

收稿日期:2021-09-22 修回日期:2021-10-19 发布日期:2021-11-09
通讯作者: 赵冰心, 徐石海
作者简介:
† 共同第一作者
基金资助:
国家重点研发计划(2019YFD0901905); 国家重点研发计划(2018YFC0310900); 国家自然科学基金(41876145); 国家自然科学基金(81874292); 国家自然科学基金(21672084); 广州市科技计划(202102010066); 广州市科技计划(201704030042)

A New Dinorspongian Diterpene with Pyridyl D-Ring from the Marine Sponge Spongia sp.

Yongqian Liang^a^,^b, Xiaojian Liao^a, Long Ling^a, Yating Yang^a, Bingxin Zhao^a(), Shihai Xu^a()

a College of Chemistry and Materials Science, Jinan University, Guangzhou 510632
b College of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006

Received:2021-09-22 Revised:2021-10-19 Published:2021-11-09
Contact: Bingxin Zhao, Shihai Xu
About author:
† These authors contributed equally to this work.
Supported by:
National Key Research and Development Plan of China(2019YFD0901905); National Key Research and Development Plan of China(2018YFC0310900); National Natural Science Foundation of China(41876145); National Natural Science Foundation of China(81874292); National Natural Science Foundation of China(21672084); Science and Technology Planning Project of Guangzhou(202102010066); Science and Technology Planning Project of Guangzhou(201704030042)

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Abstract

Chemical investigation of the marine sponge Spongia sp. led to a new dinorspongian diterpene dinorspongiapyridine (1) together with four known compounds 2~5. Compound 1 was the first instance of 3,4-seco-3,19-dinorspongian diterpene bearing a rare pyridyl D-ring system. The structure with absolute conﬁguration of 1 was elucidated by the methods of NMR and X-ray diffraction. In addition, the cytotoxic activities against several cancer cell lines of 1 were evaluated. The plausible biogenetic pathway of 1 was also proposed.

Key words: sponge, Spongia, dinorspongian diterpene, pyridyl ring

Cite this article

Yongqian Liang, Xiaojian Liao, Long Ling, Yating Yang, Bingxin Zhao, Shihai Xu. A New Dinorspongian Diterpene with Pyridyl D-Ring from the Marine Sponge Spongia sp.[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 901-904.

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Fig. & Tab. 6

References 12

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No.	δ_H	δ_C
1	a, 2.46	44.4
1	b, 2.33
2	—	175.6
4	—	214.1
5	3.24	56.6
6	a, 2.04~2.00 (m)	22.8
6	b, 2.00~1.84 (m)
7	a, 2.76 (dt, J=13.5, 3.3 Hz)	33.4
7	b, 1.59 (td, J=13.5, 5.1 Hz)
8	—	43.2
9	2.49 (dd, J=14.1, 3.6 Hz)	46.8
10	—	40.3
11	a, 3.10 (dd, J=18.3, 14.1 Hz)	36.1
11	b, 2.47
12	—	199.5
13	—	139.3
14	—	145.7
15	8.70 (s)	149.7
16	8.58 (d, J=2.1 Hz)	148.6
16	7.79 (d, J=2.1 Hz)	120.2
17	a, 4.00 (d, J=11.1 Hz)	65.8
17	b, 3.81 (d, J=11.1 Hz)
18	2.28 (s)	31.8
20	1.23 (s)	19.1

No.	δ_H	δ_C
1	a, 2.46	44.4
1	b, 2.33
2	—	175.6
4	—	214.1
5	3.24	56.6
6	a, 2.04~2.00 (m)	22.8
6	b, 2.00~1.84 (m)
7	a, 2.76 (dt, J=13.5, 3.3 Hz)	33.4
7	b, 1.59 (td, J=13.5, 5.1 Hz)
8	—	43.2
9	2.49 (dd, J=14.1, 3.6 Hz)	46.8
10	—	40.3
11	a, 3.10 (dd, J=18.3, 14.1 Hz)	36.1
11	b, 2.47
12	—	199.5
13	—	139.3
14	—	145.7
15	8.70 (s)	149.7
16	8.58 (d, J=2.1 Hz)	148.6
16	7.79 (d, J=2.1 Hz)	120.2
17	a, 4.00 (d, J=11.1 Hz)	65.8
17	b, 3.81 (d, J=11.1 Hz)
18	2.28 (s)	31.8
20	1.23 (s)	19.1

海绵Spongia sp.中一个新的D环为吡啶环的降海绵烷型二萜

A New Dinorspongian Diterpene with Pyridyl D-Ring from the Marine Sponge Spongia sp.

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